tag:humbledmba.com,2013:/posts humbledMBA 2019-08-07T13:56:03Z Jason Freedman tag:humbledmba.com,2013:Post/699744 2014-06-03T19:04:28Z 2019-08-07T13:56:03Z You’re only getting the nice feedback

When we pitched VCs for FlightCaster, we received 52 rejections before we got our first term sheet.   Every time I got a rejection, I asked for feedback.  Here’s what I heard:

Some VCs said our market was too small.  But I found that odd in that travel was a global 500 billion dollar market and lots of other travel startups were receiving VC backing and presumably those VCs cared about market size as well.

Some VCs told us they weren’t experts in the travel sector and so they wouldn’t be a good match for us.  But I found that odd because they are invested in all sorts of esoteric industries that they didn’t seem to be experts in either.  And now years later, I’ve seen those same VCs invest in other travel startups.

Some VCs said, “We like you, but we need to do some more due diligence on the space.”  Then they asked us for a bunch of hard-to-get stuff – market research, traction metrics, and better proof of growth. But even when we got them this information they still didn’t say yes.

Over the course of 52 rejections, I got tons of feedback on our startup.

I spent incredible amounts of time responding to that feedback.  I’d like to think that all this work responding to feedback and iterating on our pitch made us better, but Sunil, the VC that we got our first term sheet from didn’t care about any of that.  In fact, he didn’t even request it. As we were proceeding past the third meeting and I asked him if he wanted our due diligence pack that was filled with juicy market research data, growth metrics and industry overviews, Sunil responded quite easily, “I don’t need any of that. I’m betting on you.”  We signed the term sheet and he became our lead investor.




I’ve been thinking about that raise recently.  The big difference between Sunil and those other investors wasn’t that I had magically found a VC that was willing to take a bet on me instead of getting preoccupied with all these other due diligence items.  The real insight is that all of those other VCs wanted to make a bet on me as well, they just decided not to. To say that another way, they didn’t invest in me because they didn’t believe in me.  No other reason.

All of that concrete feedback about market size and traction and metrics.  All of that was simply the nice feedback. It was so much easier to blame it on market size then to tell me to my face that I don’t have what it takes to be a successful founder.  I’m actually quite sure that this is the case because several of those investors that rejected me for FlightCaster are now investors in 42floors. And now that I have talked to them about this, they’re willing to be frank with me.

Several of these investors put money into 42floors when we hadn’t figured out our product vision. I hadn’t done any of the market research yet and our deck still didn’t look any good.  Several of them don’t even know that much about commercial real estate.  There were tons of reasons not to invest in 42Floors.  But they had seen me grow as a founder and they were now willing to bet on me as a founder.  I do wish they had been more frank when they rejected me during FlightCaster because I wouldn’t have gone off on so many wild goose chases. But I can give them a pass on that because it’s incredibly hard to tell someone you don’t believe in them.

Paul Graham talks about this in his epic fundraising how to guide. He says, “if you’re getting a bunch of no’s it may just be investors don’t think you’re formidable.”

Here are a few tips to check yourself on whether you’re getting real feedback or the nice feedback.


How to Ignore the Nice Feedback


Get a great advisor

As I’ve said before, find a great startup advisor which specifically means a peer of yours that is twelve to eighteen months ahead of you.  This is not an industry veteran. It’s not someone who sold their company for hundreds of millions of dollars.  It is specifically someone who is good at playing the game that you’re playing, and they’re just a little bit ahead of you. Because they are the ones most likely to tell you frankly what’s going on.


Trust the feedback that repeats consistently

If you truly have some problems whether it be product vision or market size or whatever, it should be that really smart VCs will continue to see it. If your feedback feels contradictory, then you may be able to pass it off as noise and realize that you haven’t found a true signal.


Just because you ask for frank feedback, doesn’t mean you’ll get it

Some people are really good at requesting frank feedback and they ask for it specifically.  And while that will sometimes works, often it still doesn’t.  For most investors it is simply not worth the time and emotional effort to try to give really frank feedback. Realize that they say no 99% of the time, and so they consciously or subconsciously try to minimize the amount of effort it takes to say no.


Access a good back channel

If you’ve done your networking right, you hopefully know people in common with the investors you’re pitching.  Hopefully one of them gave you your initial introduction maybe as either a peer in the startup community or better yet a personal friend.  That’s the person you want to go to, to try and figure out what went wrong.  Most investors will chat with whomever your reference was and all the true nuanced color about their decision will come out.  You still may fall victim to getting nice feedback if your friend feels bad for you, but at least you have a better shot of getting it than trying to get it from the investor directly.



Finally, if you’re reading this and you have this sinking feeling in your gut that it applied to you, I can also say with great confidence that your career as an entrepreneur is not over. You simply need to become more formidable.  I wish I had an answer on how you do that, but plenty before you have figured it out – and so can you.


Discuss on Hacker News.

Jason Freedman
tag:humbledmba.com,2013:Post/697180 2014-05-28T17:38:49Z 2015-09-15T20:39:01Z Investors don’t want to meet you. They wanted to be introduced to you.

I remember when I first started fundraising for my first company, my investor network was pretty weak.  Not only did I not know many investors, I also didn’t really know how to pitch them.

I‘d basically take any meeting I could with any investor at any time.   I went to conferences, meet-ups, pitch competitions.  Every investor was an opportunity for an elevator pitch.  I was doing whatever I could, trying everything to succeed.  I figured this it what it took.  This was hustle.

It was also stupid.



One day, I met a prominent VC at a conference.  I started my elevator pitch.  But in a rare moment of candidness, he told me that he doesn’t go to conferences to meet new startups.  He told me, “By the time they get here, they’re already picked over.”

Here I had thought this man with deep pockets of other people’s money was evaluating me and my pitch. But empirically he knew that he wasn’t going to find his next investment that way.  He was there to build relationships with the most successful founders so that they would introduce them to startups they liked.  I’d been wasting my time.


Investors don’t want to meet you.  They wanted to be introduced to you.


It’s a huge difference.  Another top tier VC once told me that out of the thousands of business pitches he receives in his office every year, his firm has never funded one that came in completely cold.  In other words, the only way to get their investment was through an introduction.

It makes sense.  The job of a venture capitalist is finding a needle in the haystack.  And it’s just not functionally possible to do that by evaluating every single one.  So investors rely on their network to do the first round of vetting.

This little insight should dramatically change how you raise money.  Instead of trying to build a network of investors, you should be building a network of introducers.  And not all introducers are created equal.  Here’s a guide to help you.



How to Get Warms Introductions


Get Intros to Your Friends’ Investors

If you’re working in any startup hub, you almost certainly have friends that are working on their own startups.  Ask them to help you. The first question should be, “Am I ready to fundraise?”  You need to ask this not only for the answer, but also to see just how warm your friend’s introduction will be.  If they like you, but they don’t believe in your startup yet, then it will be impossible for them to hide that perspective from their own investors.  But once you get the go-ahead, you should absolutely ask them for introductions. And not to get too bogged down in logistics, but here’s how you should do it:

Send them a fresh email requesting an introduction to a specific investor with enough information that it can be forwarded by your friend without further editing and short enough that the investor can read it on their mobile phone.  Assume that no attachments will be opened and that no links will be clicked.


Get Introductions from Entrepreneurs That Are Not Yet Your Friends

If you are not yet friends with everyone in the PayPal mafia or the YC alumni crew, you’re friend’s list may not reach as far as you need to go.  That’s not a problem because most founders are willing to help out other founders when approached in the right way.  I regularly introduce other startups to my own investors, and it’s a win win for both sides.

When you are approaching another entrepreneur for an intro, you need to actually sell them on your startup because an entrepreneur will only make an introduction to her investors if they believe there is high likelihood that that introduction will result in an investment; it affects their own credibility when it doesn’t.   And secondly, they want to spend very little time getting involved because their job is their startup – not helping you raise money.

But with that said, it’s much easier to get a meeting with another founder than it is to get a meeting with a prominent venture capitalist.  The trick is you have to ask first for fund-raising advice, and not for introductions.  When you go to another founder for advice, especially if you approach a non-famous founder who doesn’t get this request too often, they’ll love playing the role of teacher and giving you helpful feedback.  And if they get excited about what you’re doing, they will offer to make that introduction for you.


Get Intros from Your Early Investors

The second that wire comes through, you need to turn your early investors into evangelists.  They are now your best source of warm introductions.  But you have to help them be helpful. They don’t know who you’ve already talked to and where you need help.

When I was seed-stage fundraising, I liked to keep an investor wish-list on a Google doc.  It was a list of twenty investors I wanted to meet in order of general priority.  Whenever I would get a new Angel on board, I would show them that list and they would respond back with who it is they knew.  Immediately I would send them a fresh email for each new intro. BOOM! Three to five more investors in the pipeline.


Stay organized

You need a well organized investor pipeline.  This is where you keep track of each investor that you’ve approached as well as those that you would like to approach. A good fundraising process will involve 40 to 60 meetings, so it’s impossible to do this just in email.  This document should not only keep track of your status with each one, but also who you have in common with each person.  I like to go through this list methodically checking each investor name on both LinkedIn and Facebook to see what possible introduction I have available to me.  I then try to balance each potential introducer out so that the people who can provide the best introductions are evenly distributed.  Asking for three introductions is  totally fine, and five is probably pushing it, unless she is either close friend or already an investor.



Your goal by the end is to have 40 to 60 introductions.  Our travel startup took about 60 meetings, as did our office space startup.   If you raise your round in the first 10 meetings, then kudos to you.  And when you do get your round done, be generous with your time and pay it forward to other entrepreneurs.

And, if I personally can be helpful to you.  Ping me on Twitter.  I’ll do whatever I can.



Discuss on Hacker News.

Jason Freedman
tag:humbledmba.com,2013:Post/694987 2014-05-22T19:44:03Z 2015-09-15T20:39:11Z The Year of Operations Startups

When we started 42Floors, I didn’t know it was going to be an operations startup.  Naively, I thought it was going to be an office space marketplace centered around a great product – one of these places where supply and demand come together, one pulling the other and vice versa.

And the way we built our company reflected this.  Our first ten hires, including the founding team, were all great product people.   Before we had a single listing secured in our database, we had already iterated many times over the interface.  It’s a preference that many of us in the startup world have.  Our talent is for making beautiful, simple products.  And so that’s how we choose to attack each problem.

Six months ago, we knew we knew we had a problem at our company.  We were attacking every operations challenge with a product solution and it was getting us into trouble.  It was Chris Dixon who really opened my eyes.  After he invested in 42Floors, we walked through our plans for automating the acquisition of listings.  And he told me plainly that I needed to scale a manual process. There may be a day when brokerages and landlords have all of their listings automatically exported into 42Floors, but that’s not happening anytime soon.

Today, we have a tremendous operation that collects commercial real estate data twenty different ways so that our users can view available office spaces on a simple app.  We manually process email blasts. We manually check for website updates.  We make thousands of phone calls.  We have photographers in every city.  We upload each individual photo and use our own team to categorize each amenity.  And that’s just to name a few.  And once someone starts looking for office space on our site that kicks off a whole additional stream of individual manual activities we have to perform to help them find their space.




This year is going to be the year of the operation startup.  It’s already abundantly clear to me.  The seeds were definitely sown in 2013, but we really have only just seen the beginning.  Uber is definitely one of the leaders with a very simple mobile product on the front end and a very sophisticated operations engine on the backend.  We have startups like Instacart with a wonderfully simple mobile app attached to a tremendously complicated supply chain machine.  You can throw in the whole wave of delivery apps in here:  Postmates, GrubHub, Bloom That, and more.  This list could go on and on and there’s going to be so many more in 2014.

The prevalence of smartphones is definitely a catalyst for this new wave of startups.  Cheap ubiquitous smartphones means that everyone interacting in your operations has access to custom built apps.

But perhaps the real motivating factor is simply that we entrepreneurs became less afraid.  I’m willing to admit it. I spent the first year at 42Floors afraid that it would become some boring operations company.  Our competitors rely on updated manual process, so I figured we should be focused on building true technology.

But now I get that a technology company can become really good at scaling simple operations.  Along the way we’ve learned a few things about what it means to be an operations company.  Hopefully, some of this will be helpful to you.


How to Build an Operations Startup

Don’t be afraid of manual processes

This actually goes for all companies.  Early on, whenever you can replace code with a manual process, you should; if for no other reason than it can help you to iterate faster.  We do it religiously at 42Floors.  Everything starts manually.  Save your precious engineering cycles for the times when you actually need it.


Fix what’s broken and not until then

The inevitable complaint you will receive from everyone on your team is some manual operation could be done better, and they’ll be intent on building out the scalable version.  You’ve got to resist this as much as you possibly can.  Focus on the bottlenecks, the things that are most broken in your company, and fix those first.


Become a power Google spreadsheets user

Google spreadsheets can get you so incredibly far that it’s worth thinking of it not simply as a quick temporary measure but actually as your short and medium term strategy.  Because every time you use Google spreadsheets, you’re starting with a piece of software that everyone understands how to use and is pretty scalable.  Sure you’re always going to be missing the features of a full feature solution for whatever you’re doing. But the hassle of, say, moving your sales team to Salesforce is simply not worth it early on.  It’s also worth learning how to use the Google spreadsheets API so you can both read and write from your database to your spreadsheets.


Hire specifically for biz ops

I don’t know if that’s a word that’s going to stick, but I’ve seen it mentioned a few times and it feels like it’s the most relevant term for this emerging function of a company.  Biz ops people always have a little bit of sales to them in that they like tracking throughput and conversion rates.  They’re accustomed to monitoring pipelines and judging themselves purely on results.  The big key is you want biz ops people that come from the startup world.  The last thing in the world you want is a big company perspective too early. When in doubt choose the scrappy operator who can duct tape anything together over the sophisticated guy with credentials.


Measure your operations

We’re all really good at measuring user acquisition funnels, performance, SEM campaigns, and we have a bundle of out-of-the-box SaaS tools that help us with measuring all of these standard startup metrics.  But your company’s business operations is going to be much more challenging to use an out-of-the-box tool for.  But it’s even more important that you get those metrics up on your dashboards.  We use Chart.io in our office which allows us to draw custom graphs based on anything we have in our database. Even still, it’s challenging. But if your company is going to become good at operations you have to be analytics oriented.


Hire people who can figure shit out

You’re going to have this tension in hiring your various operators. You need people who are able to do stuff, and often a lot of those things are repetitive.  If your company were to never grow or change, you would simply want someone who could adequately do the job and be comfortable doing it for many years.  But your company is going to grow and scaling the operations is going to be one of your ongoing challenges that never go away.  When in doubt, hire the person who will help you figure out to change things, even if they’ll be bored with the job earlier than you would prefer.



I’d love to hear your thoughts.  This is going to be big year for operations startups. Don’t be afraid to put a little elbow grease into your vision.



Discuss on Hacker News.

Jason Freedman
tag:humbledmba.com,2013:Post/693266 2014-05-19T19:21:02Z 2015-09-15T20:40:27Z I want to get into startups, but I don't know where to start

I just chatted with this great guy, Alex, out of Boston who wants to get into startups. He graduated from a good college a couple of years ago. He’s bounced around a couple of times in corporately jobs that aren’t the right match and he is ready to take the leap.  He took a couple of classes in computer science, so he’s familiar with code but he’s clearly not an engineer.  He doesn’t have (at least not yet) that founder’s spark that propels him to build something on his own.  Alex wants to join a startup. He just doesn’t know where to start. 

I should mention that Alex is awesome – super, super smart, with both natural analytical abilities and good social skills on the phone. Even from my brief conversation with him, I can tell he is ambitious and passionate. He’s the type of guy lots of startups would like to have. Clearly he was low on experience, but he seems to be a fast learner so whatever he decides to do, I bet he’ll pick it up quickly.

I realized after hanging up the phone with him that the startup community needs more people like him. For years when startups weren’t cool, most top graduates went into finance, consulting and other big company jobs.  Finally, our sector is on top and these young people that want to come and join us. That’s awesome!

But we startups are collectively are still really bad at helping them break into our tight-knit community. Compare Alex’s experience on his college campus a couple of years ago. Throughout the year, there were career fairs and on-campus interviews.  While a few tech companies show up at the career fairs, mostly those are really big companies like Google or Microsoft or Yahoo.  Virtually, no startups showed up unless it was a large startup and the founder herself had gone to that school.

It’s no surprise that Alex mistakenly chose a big company over a startup straight out of school even though he was already interested in startups. There were literally hundreds of other companies ahead of us pitching careers in consulting and banking, or whatever. And those companies all have workshops where they teach you about their industry and what it’s like to be a first time employee. There are career help books written about each industry.

The schools have learned all of this and repackaged it into career centers that give tailored advice. It’s this whole machine that makes it easy to know exactly what you’re doing as a new entrant into the job market.  And when they do get that job, these big companies have expansive training programs to help their newest employees hit the ground running.

And we have nothing.  Startups are nowhere to be found on campus colleges, maybe with the exception of Stanford and MIT.

If you’re a recent or soon-to-be college grad, this post is for you. I thought it would be helpful, to show exactly what roles are available in a web startup and what you should do to prepare yourself.


Startup Roles

The Engineer

The largest gap between supply and demand is for engineers.  Specifically, hackers that like to build stuff. Hopefully within your computer science courses you’re learning the right principles, but make sure you’re building stuff in modern languages and frameworks outside of class.  The biggest thing we look for at 42floors is evidence of side projects. Side projects are when young hackers build things the way they want to build them. We love to see that people have gravitated towards the best tools for the job and are naturally creative.  In most cases the people we like to hire can’t help but build things for themselves in their spare time.

Out of all startup jobs, getting a job as an engineer has probably the most clarity. Spend your time honing your craft and you’ll do just fine.


The Product Person

This is often called the product manager or PM for short, but you should probably omit the word management for the time being. If you’re looking to break into startups for the first time you’re not going to be managing anyone no matter how experienced you were in other jobs.

A product person loves building stuff and analyzing traffic. Often times they’re also engineers or have some level of coding abilities but may lack an extensive background/interest in computer science.  Product managers can usually do a little bit of each of these tasks: designing in Photoshop, customer development, working with engineers, rapid prototyping, analyzing conversion metrics and project management.  And usually you’ll be really, really good at at least one of those.

If you’re interested in being a product person, you should just look at that list and fill in your own gaps. Focus specifically on the concrete skills like Photoshop or prototyping. Photoshop is an essential skill and you should just have it.  And by rapid prototyping I mean the ability to build mockups of whatever idea you have in your head, either through writing your own code or by using any of the various SaaS products that make rapid prototyping easy.  Being really good at using lots of different  SaaS products to get stuff done is in itself a totally awesome skill to have.


The Salesperson

Sales people are non-stop hustlers. When you’re entry level sales at a startup, you’re picking up the phone 70 to 100 times a day.  I find a lot of ex-athletes are both interested and good at this type of job (sorry to generalize, but it’s true).  They love the thrill of working hard and seeing a result. They’re not afraid of repetitive tasks and they’re fundamentally competitive with other sales person, which is intrinsic to a good sales culture.  If you want to break into sales, think about joining a slightly larger startup because it’s really helpful to have learned inside of a really good sales operation. There is no need to go really big like Salesforce or Oracle.  Those will teach you bad habits.  But doing sales at a reasonably sized late-stage startup, like Box.net, will teach you all the right skills that you can then take anywhere.

Regardless of where you decide to go, the single best preparation is to get good at getting the job itself. Sales people must be persistent. So demonstrate that in your job search process.  Learn how to find that balance of respectful persistence.  The very best junior salespeople get their start simply by not accepting rejections.

If this you, you should contact us—we want you on our team.


Business Development

While often lumped together, business development is slightly different than sales. These are for people that love networking, building relationships. They have a sense that they can nab a meeting with anyone, but they wouldn’t last if they were expected to make a hundred phone calls a day.  A few courses in business are super helpful because fundamentally business development people need to be making deals.  If you take any one course to prepare you for this type of job it would be negotiations, and if your school doesn’t have negotiations, there are plenty good books out there.  I’ve never met a good biz dev person who doesn’t consider themselves awesome at poker, monopoly, settlers, etc.

This is a harder job to get for an entry level candidate, unless you’re working at a really early stage company and have a personal relationship with the founders.  Most people get into higher level business development by proving their skills at basic sales first.



There is still a little bit of traditional marketing left in startups, but not much.  The stuff where you talk about brand and marketing messages and whatnot – those jobs have mostly gone away already.  It still happens, but not by one dedicated person.  If you want traditional brand marketing, stick to bigger companies.

Every good startup I know is currently hiring a growth hacker, which is really just a marketing position for a technical or mostly technical person.  This could be a good role for you if you’re super analytical about metrics and the first time you used a spreadsheet it became second nature. You want to be practiced in SEO and SEM.  But more than anything, you need to be naturally good at pulling off shenanigans. I don’t mean doing unethical stuff, I mean being able to hack together experiments quickly to see if they’ll work.  The best prep for this type of role is generally side projects as well.  Do something that generates tons of adoption. In the course of it you’ll learn all the tips and tricks.


Account Management/Customer Service

These can be great entry level roles.  The two big skills you have to bring to the table are empathy and organization.  Empathy can’t really be taught, so if you don’t have it, don’t go down this road. But if you do have it you’ll naturally be good at working with clients and helping understand their needs.  And then organization is essential because in any good role, you’ll have to do it at increasingly high volumes.

So really good account manager/customer service types are a little OCD about organization – they love experimenting with various CRM ticketing products like Zendesk, Streak, etc.

By the way, our little commercial real estate startup would love to have you join us.


Office Managers

This can be a super-fun job that can grow into a substantial career. The startup office manager, especially if he joins early on, gets to do a thousand different things.  It’s part office design, meal provider, HR exec, accountant, and more. Even more than the account manager, the office manager needs to be obsessed with organization.  I also find that this particular position seems to almost always get filled by personal connections. There is something about having the right personality fit for that particular startup that is especially important. So, if you are interested in doing this, the most important thing is that you spend time around lots of startups.




There is a lot more we in the startup community need to do to make easier to join a startup, but hopefully this post at least helps get you started.



One last note!  Entrepreneur friends: feel free to post your best how-to-get-a-startup-job advice below.  And if you do, you’re also welcome to post a job ad for your startup as well.


Discuss on Hacker News.

Jason Freedman
tag:humbledmba.com,2013:Post/691889 2014-05-16T02:10:25Z 2015-09-15T20:40:47Z I don't know

I wanted to share an interesting conversation I had with Kiran Divvela back when he was still interviewing.

Kiran runs all of our data supply chain activities. He’s one of those rare types that communicates well, has solid management skills, is fluent technically, and was a perfect startup culture fit.  We knew we had to have him.

But Kiran was one of our toughest hires.  We knew he had options.  We thought that we were in the lead for him culture-fit wise.  The big question left for Kiran was learning enough about our industry since commercial real estate was new to him. He needed to truly believe he was going to be part of building a big company.

After we made him the offer, I made myself available to talk through any questions he had.  It was like fundraising due diligence all over again. We went through the deck, and I showed him our short, medium and long terms plans. We went on long walks where we talked about each piece of our strategic plan.

One moment has stuck in my mind.  He was asking me how we were going to keep our data updated once we were at scale.  It was an important question. If you fail at it, users have the worst experience possible, calling on listings that actually aren’t available.  If you’re great at it, you become known as the best source of information anywhere and everyone flocks to you.

Kiran would be leading our data efforts and that would include not only acquiring the data but keeping it updated.  At this point, in the young life of our startup, simply getting commercial real estate listings was the most important activity.  Keeping them updated was a challenge I knew was on the horizon but we hadn’t had to deal with it too much yet.  With our small scale at the time, we had been able to solve this problem manually. That wouldn’t really work at scale.  As we walked down the street, doing yet another lap around South Park, I shared a few of my ideas with him.

But they weren’t great ideas.  More like trying to write with a crayon when the rest of our conversation had been written in pen.

Finally I cut myself off and told him flatly, “Look, I don’t really know.”

It was the truth.

Every commercial real estate listings company – actually every real estate tech company, commercial or residential – has struggled to figure out how to keep listings updated. While there are lots of tactics, there is no one true silver bullet. I had lots of ideas I wanted to try. One of the reasons I was so excited to have Kiran on board was that he would be the one who would actually get to try them, as well as come up with tons of new ideas.  But at this moment, the most truthful answer I could give him was, I don’t know.

And he smiled and responded back, “I was waiting for that. I like it when people say I don’t know.”

I burst out laughing.

Kiran explained that he likes it when people say I don’t know because it lends credibility to everything else that they’ve said.  He was already pretty close to making up his mind that he was coming to 42Floors, he just wanted an honest accounting of what we had answers to and what remained as questions.




Ever since that encounter, I’ve tried to pay attention a lot more when people say I don’t know.  We did a whole bunch of Y Combinator mock interviews during the last session. The YC alumni in our company try to offer some time before each batch to work with the people that are preparing.

I found that very few of the startups were willing to use the words I don’t know.  A couple of times a founder was in such a salesy mode that we both knew he was bullshitting his answers, but he refused to show anything other than total confidence.  I just saw it as foolishly naïve.

One startup that got in actually used the words ‘I don’t know’ several times.  The founder was super confident in her product, super confident in her team but had some uncertainties about how she was going to acquire users and didn’t really know how big her market was, both of which were problems she said she would address.  But it was so refreshing to hear her honesty.

I don’t have enough data points to generalize yet, but it seems promising.  If you have the confidence and honesty to say I don’t know, you’re probably going to win over a lot of people.




One place I’ve always struggled to say I don’t know is when talking with engineers about technical stuff beyond my knowledge.  No one wants to look stupid so it’s easier to nod your head when you don’t know what someone is talking about. I realize now it creates the opposite effect.  Every time I appear to understand something I don’t, it just makes me look foolish.

I try now to just simply say that I don’t know and ask people to explain things to me.  Fairly regularly, one of our engineers, Aaron O’Connell, will take time to explain what it is he’s working on. He’s got a Ph.D. in physics and he’s a gifted coder, but he never seems to mind taking the time to explain it to me in a way that I can understand.

See, no big deal.

I also say I don’t know a ton to my board.  We have super smart guys on our board and nothing gets past them.  Saying I don’t know with them turns a question into a homework assignment.  As long as I follow up with the answer later, they never mind.  And it’s 1000x better than bullshitting a half answer.




Thank you Kiran for inspiring this post.



Discuss on Hacker News

Jason Freedman
tag:humbledmba.com,2013:Post/689965 2014-05-12T16:34:44Z 2019-08-07T13:52:56Z Thirty Percent Feedback

I remember showing school essays to my dad growing up. He’s a really good writer and so getting his feedback before I turned a paper in usually helped me make some improvements.  But whenever I’d watch him reading over the pages, I would secretly be hoping he’d read it and say that everything is perfect.  I obviously thought it was already perfect, otherwise I wouldn’t have shown it to him.

The truth is I didn’t really want any critical feedback.  As a teenager trying to finish his homework, my only goal was to do the minimal amount of effort necessary to get a good grade and be done with it.

It was such a harmful way to think.  And I’ve noticed that I have let it carry into my startup life as well.  Often times, when I seek feedback on a project, it’s not actually constructive feedback that I want; it’s simply approval.  I want a pat on the back and a “job well done.”  Of course, that doesn’t push me to work harder.  It doesn’t provide me new perspectives.  And it certainly doesn’t yield the best product.

I’ve noticed that most people have difficulty seeking constructive feedback.  If you’re pretty good you can at least accept constructive feedback, but rarely will you actively seek it out.  Often times you’ll still be plagued by that teenage desire to simply seek approval.

But when you meet someone who is hungry for tough feedback, the effect is powerful.  You can just tell that they’re going to be successful because they are so hungry for information.  Their pace of learning is so much quicker than anyone else who toils alone.  They don’t take criticism of their work personally, and because of this, they exude a deep sense of confidence.  I’m always inspired when I see that in its purest form.




But, if you’re someone that struggles with seeking out tough feedback here’s a little trick we use at 42Floors.

We call it Thirty Percent Feedback.  It’s a trick I learned from our investor, Seth Lieberman.  It came about because I once asked him for feedback on a product mockup, and he asked if I felt like I was ninety percent done or thirty percent done. If I was ninety percent done, he would try to correct me on every little detail possible because otherwise a typo might make it into production. But if I had told him I was only thirty percent done, he would gloss over the tiny mistakes, knowing that I would correct them later.  He would engage in broader conversations about what the product should be.

In this particular case, I was indeed ninety percent done and so we debated a few details, I got my pat on the back, and I moved on.

As he was leaving, he said:

“Next time come to me when you’re only thirty percent done and I’ll give you thirty percent feedback.”

So a few months later on a different project, I came to him with some questions on a project that was still in its early stages and we wrestled with the direction together.  I didn’t polish anything and he made sure not to critique things he knew I would fix later.  It was really freeing. I knew I wasn’t putting my best foot forward and he didn’t care.  He was able to help me shift course without the sunk cost of throwing away a ton of work.  Really awesome.



We try to do a Thirty Percent Feedback sessions whenever we can  in our office.  It’s not easy though. Most people I find still want to wait until they’re ninety percent done.  But that’s rarely optimal and usually involves painful rewrites.

If you want to get your team on board with Thirty Percent Feedback, it won’t be easy.  Here are a few suggestions to help you get there:


How to Build 30 Percent Feedback into the Culture of Your Startup



Lead by example


Don’t worry about anything else below if you can’t there.

Ask for it explicitly

You have to be deliberate because you’re fighting against an innate fear most people have: fear of rejection.   Some of your best people are accustomed to being good at everything they do, so they may be the toughest to get on board.

You have to explicitly ask people to be on board with this concept.


Reward People with great feedback

Whenever someone comes to you for early feedback you have to reward it.  If, even just once, you reject someone’s draft because it’s not polished enough for you, you’ll teach everyone else in the organization to always be 100% done before approaching you.

Execs at big companies may want everything perfect before it gets to them, but that’s no way to run a startup.

Praise Speed

When someone takes way too long to get a first draft out because they’re being perfectionists and you praise them for their quality craftsmanship, it teaches everyone to do the same.  You should, instead, praise people that move incredibly fast.  We always strive for one week.  Even for the most complex projects, we try to see what can come out as a first draft within one week.  From that point on, they can get feedback and start iterating.


Demo Regularly

Set up the company for everyone to demo at your weekly meetings, regardless of what stage their project is in.  It’s more of a show us whatever you have.  PG would do this to us at YC, making us demo every week.  It was both daunting and humbling.  But once we got used to it, we actually got addicted to the immediate feedback.  That’s the culture you want.



One final note.  Every once in awhile you’ll still have to give someone  tough feedback when they thought they were 90% or 100% done.  It always feel shitty to have throw away work.  But hopefully with this system, it will happen much less.  And the result will not only be better products, but happier people.



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Jason Freedman
tag:humbledmba.com,2013:Post/688581 2014-05-08T21:54:51Z 2015-09-15T20:41:29Z I can rest easy. We’re finally home.

I wrote this post stream of conscious the night we moved into our new office.  Instead of editing it down into my usual bite-size blog post style, I thought I’d share it as is.  It covers a lot of the emotions and thoughts I had, which I hope will be helpful in some way to you.


We just moved into our new office at 501 Folsom Street.  We’re finally home.

In the end we toured fifty spaces.  That’s right. 5-0.

As a company that makes it easy to search for commercial real estate, I can tell you that finding this office space wasn’t easy.  Of course we had the benefit of knowing our market really well and it was really fun to eat our own proverbial dog food. But it was still hard.

We started by searching for 5000 sqft and ended up with 15,000 sqft.

When we started searching, we were thirteen people so I was looking for a space that would hold fifty.   But when we finally actually moved, we were twenty-four so I wanted a place that would hold eighty.  Our square footage requirement was as low as 5,000 sq. ft. and as high as 20,000.  It changed so often because neither our optimism of our own future nor value in the market ever remained constant.  In general though, it went up.

We ended up with a 15,000 sq. ft. lease that we’re subleasing half of for the next 18 months.  The ability to get a bigger space and sublease out one of the floors made it so we could stay here longer without overpaying so much up front.




We fell in love with three spaces over the course of our search, but this is the one that was right for us. At the point that we came to terms on the offer we still had five weeks of negotiating to hammer out the details of the lease;  during which time almost nothing substantive changed.  And then we had another six weeks to prepare for the move-in, but that was because there was almost no building involved.  We had a little bit of light demo work and we got to keep a lot of the furniture from the previous tenant.

All in all, 7 months from the date we went on our first tour until our moving date.




It was a surreal day walking into our new office. Emily was bouncing up and down in excitement. She was excited about it all weekend. She said it was like waiting for the first day of school.  Funny, I remember feeling very differently about the first day of school, but I know what she meant.  It’s so surreal to walk into a new home.

It’s an incredible space.  Alison did such a good job putting it together.  In the end, we didn’t spend much – a few plants here and there, a bunch of couches to make it feel homey, a dedicated bug-house table taking center stage.

I had a really hard time focusing today. I spent a good chunk of it walking around. Again, just feeling surreal.  I found that I simultaneously just wanted to step back and soak it in yet, also had a need to understand each detail of the space.

Alison and I worked on making sure each desk was perfectly aligned and that the office maintained a sense of symmetry throughout.  Darren is of course happy in his new cave, protected from distraction just as he wanted to be.  We managed to have a nice balance between open space for those that want open space and cave-like space for those that want cave-like space.

In fact, we have a room called the W.F.H.F.O which stands for ‘Work from Home from the Office’.  It’s for people who want total isolation from the rest of the company.  It’s a small room with good light and two desks.  If you want to tune out the rest of the company and plug in for awhile, it’s always available.




For a founder, picking a new office is one of the most concrete measurements of your own faith in your company’s future.  We went from 5,000 sq. ft. to 15,000 sq. ft.  Is it too big? Is it not big enough? We moved five times in 25 months which to me is proof that each time we weren’t optimistic enough.  But the truth is it’s hard to envision your company doubling and doubling again.

When we were four people living in the house in Redwood City with $80,000 in our bank account, it was hard enough to imagine the company doubling in size so we picked a small place that could hold eight.  Months later we were eight people and we had to quickly move so I picked a place that would hold sixteen.  But after six months there, we’d already reached sixteen so we started looking for a new office.

And that’s when it took seven months to find 501 Folsom.  By the time we left, our space designed for sixteen people had desks jammed in everywhere.  Twenty-four desks in 2,500 sqft.  Cozy to say the least.

So is 15,000 sq. ft. too big for us? We figure we can fit up to a hundred people in there. That means that we would have to double and then double again.  FlightCaster, my last company, at its biggest point had thirteen people in it.  So it’s hard for me to imagine what a hundred feels like.  What if our growth slows? What if this is the biggest we get and our monthly rent becomes a drain on the company?  These are the concerns I have.  They probably won’t go away.  It’s just the reality of being a founder.  I don’t think as much about what if we grew too much. That seems like a good problem to have.




I’m writing this post late in the evening on our first day in this new space.  After all this back and forth and searching and concern, I guess the biggest feeling I have is relief.  Everyone is happy here.  They’re going to do their best work. We’re going to succeed big here, or we’re going to fail here.  I don’t miss any of the places we’ve worked at before; they were all truly special. But, those chapters are closed.  This next chapter is the most exciting yet because it’s the one we’re in right now.

It’s moments like this that remind me why we started 42Floors.  If you’ve ever looked at any other commercial real estate website (though I don’t recommend it), you’ll find that they treat commercial real estate like an asset class.  The buildings all have measurements and specifications, short descriptions, typically with a stock photo of the outside of the building.  It made sense because real estate investors care about this stuff and they were the primary users of the data.  But I always knew that a search for an office space was something far more personal. It wasn’t just finding the space that fits at the right price.  It’s not even really the purchase of a product.

The people at 42Floors are my family, and I spend all of my time trying to support them and help them achieve great things.  They’ve chosen to make their job a significant part of their life.  So I don’t want this to be an office.  I want this to be a home.

At 9:00 p.m. tonight the office is still 3/4 full, leftover Thai food in the kitchen, a few people still working at their desks, and others playing board games, friends and girlfriends coming over.  I can  rest easy. We’re finally home.


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Jason Freedman
tag:humbledmba.com,2013:Post/686434 2014-05-04T19:29:42Z 2015-09-15T20:41:49Z Still Traumatized By Classrooms

I spent this past week in Colorado studying for the Colorado Broker’s Exam. One of the little fun facts about running a commercial real estate website is that we have to be licensed in every state in order to receive referral fees.   So here I am in Colorado, studying away. 

I signed up for one of these exam prep courses where a teacher goes through the material. Back in the classroom.  It seemed like the best way to prepare.

Forty five minutes into the class, I packed up my stuff and walked out.

I felt bad. I knew it was rude, but I just couldn't help it. Being in a classroom brought back so many terrible memories. And I’m not 16 years old anymore; I don’t have to sit in class trying to learn in a way that doesn't work for me.  So I apologized profusely, took the course materials I had already paid for and went to Panera Bread where I camped out at a table for the next four days straight.

I opened the text book to start working my way through the material, but again I felt all of this pain. I just couldn't stay focused on a book full of materials. I learn through application. I have to be doing something.


So I went scouring the internet and found a bunch of websites that claim to teach the Colorado broker exam material.

One was video based – this was really just like an online version of the classroom. Though it did have the nice advantage that I could speed up the pace of the video and fast forward through parts I already knew.

One of the nicer ones involved an adaptive curriculum. It had me take a pretest to determine my weaknesses and then tailored the content I should work on based on plugging my biggest holes.   It gave me the option of jumping right into tests or studying the text of the material first.  I found that I usually would take the text outright even if I’d never seen the material before.  There is something engaging about seeing the outcome firsthand even if I was struggling.  It made the hours of preparation that followed far more focused.

One site had a really well done community feature. Whenever I got stuck, I could search for other people that had the same questions.  I realized that the act of acting questions is one of the many things that had pissed me off about being in a classroom setting.  Why should I have to listen to every single person’s question?  On an internet course, I can search for only the questions that are pertinent to me and skip the rest.

Another great aspect of this was that I got to study at my own pace.  Because I wasn't in a classroom environment I didn't have to go the speed of the lowest common denominator.  I found the math part really intuitive and skipped a lot of the extra examples and explanations.  But the vocab was initially really demanding, so I slowed everything down so that I could understand each piece.

I feel a little guilty saying this – but, I love not having to deal with a teacher.  While I have had some truly great teachers in my life, far too many of them have been consumed by control issues.  Without the need to impress a teacher by doing as he says, I was freed to just engage with the material directly.  I don’t really know what to make about that part.  I definitely missed out on something by not having access to a great teacher, but I don’t regret at all being able to avoid interacting with a simply average teacher.  Maybe the take-away is I loved not having obedience being a part of my learning experience.

The same should also be said for not having a relationship with my classmates. I did all of the studying alone. There is definitely something I missed by not being able to engage and share with them other than through the forums.  But for a single educational goal like this, it made sense to focus on doing what would be most effective.




I bring all of this up because I've been thinking a lot about our broken education system and what we as a tech community are doing about it. I’m pre-occupied by commercial real estate right now.  But I’d be willing to bet that the negative experience I just shared about traditional classroom settings struck a chord with many of you.  A good number of us just don’t do well in these traditional settings.

Over the past few years, we've had a new wave of education-oriented startups.  A bunch of them have focused on coding. It makes sense. Entrepreneurs are building the teaching methods the way they would have wanted it: CodeacademyUdemyTreehouse,Code.orgTynker, etc. – tons of innovation going on there with adaptive software, games, leaderboards, collaborative forums.

Higher education is also seeing the earliest signs of embracing technology.  My good friend Chuck Eesley runs Stanford’s Intro to Entrepreneurship program which has a massive online following.

And perhaps the most interesting example I’ve heard of recently is an online school created by The University of Southern New Hampshire called College for America. My old cofounder from OpenVote, Colin Van Ostern, just joined the team as their head of marketing. They’re making it easy for workers to receive certification in various job skills, like for instance, the  McDonald’s cashier who wants to study to become a manager.  And they’re doing it online with the principles of meritocracy not obedience at the center so students can progress at any speed that they want and are measured purely on their mastery of the material.

I’ll almost make a plug for Imagine K12 which is kind of like YCombinator but for education oriented startups. In fact, the YC partners helped ImagineK12 get off the ground.

If I were doing a startup in the educational space, I would start there.

Finally, a broad ‘Thank You’ to all of you who are doing interesting things in education. I don’t think the negative experiences that many of us had in the classroom setting are inevitable. Like anything we do, we have the ability to change the world into something that’s simpler, more user-friendly.  And nothing needs it more than our educational system.

If you’re doing something cool in education, please let me know.  I’ll do anything I can to help.




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Jason Freedman
tag:humbledmba.com,2013:Post/685127 2014-05-01T15:58:16Z 2015-09-15T20:42:07Z Sleeping with Your Gadgets On

I have severe insomnia. Specifically, delayed sleep phase syndrome.   Which basically means that, like a teenager, my body actually prefers to stay up really late and wake up really late.  I saw a number of sleep doctors several years ago, and they told me the only way I would be able to consistently go to sleep at a normal time would be to live like a hermit at night: nothing but a candle after sundown.

I tried it for a month.

It was tortuous.  To be fair, it did work.  Removing the light around me at night did help me go to sleep much earlier.  I would read or write–those were my two options.  If I found a good book, I’d just end up reading the book all night long though.  So I tried reading boring books, but that was soooo boring. The routine was just not sustainable.




Fast forward to today.

Every night I might read a little while on my Kindle or sneak in a game of Settlers on my iPad. When I actually go to sleep, I like to watch re-runs of old television shows on my laptop; I think I’m on my eighth trip through The Office.    Usually, in the middle of the second episode, I doze off.  Usually before midnight.

This is my routine and it works for me.

Being able to fall asleep early has massively improved my quality of life.  I’m able to get up early without an alarm and actually be productive in the morning.  Perhaps more importantly, I don’t spend hours trying to fall asleep. It generally takes 30 to 40 minutes.

For me falling asleep takes a cooling down period where my mind slowly disengages.  That’s why watching old TV shows is so effective; it gives me something to focus on without letting me really engage.

I am able to do all this without letting the blue light of my devices keep me awake.  If you remember, I once wrote a post called “Become a Morning Person. How to End Insomnia for $520.99” and in it I talk extensively how important light regulation is to beating insomnia.  In short, I need really bright lights in the morning, and I need to avoid almost all blue light at night.  Even a little bit of blue light is enough to keep me awake, and backlit screens are one of the worse sources of blue light for your eyes.  But after much iteration, I have found ways to block almost all of the blue light, and it has allowed me to use my devices at night without any sleep penalty.

Here’s how you can do it as well.


How to block all blue light from your devices


F.lux on your computer screen

Obviously, anyone who is reading a post like this already has f.lux.  It’s a no brainer. Download it for free here.  It will change the color temperature of your screen so that it emits less blue light.  But most people wrongly assume that f.lux blocks all the blue light.  In fact, it blocks a pretty small percentage; you have to go much further, especially if you have severe insomnia like I do.


Screenshade on your computer

This is a little free download for Macs that basically puts a transparent PNG in front of your screen. Toggle it whenever you’re ready to turn it on. Obviously you’ve already turned your dimmer down as far as it will go.  Screenshade effectively makes it so that your screen is twice as dim. But trust me; once your eyes adjust to a dark room, it will still be plenty bright.  So, even this is not enough.


Plastic filters

I use a blue light screen filter from LowBlueLights.com which I attach to my laptop screen.  With f.lux on, the dimmer down, and  Screenshade turned on,  this plastic filter then removes any remaining blue light. The screen is now so dark that you can barely tell if it’s on during the day.  But at night, with 2 to 3 minute for your eyes to adjust, you’ll still be able to watch videos.


F.lux for your iPad

Yes, you can get f.lux for your iPad, but you have to jailbreak it.  It’s actually the only reason I bother to jailbreak.


Plastic filters for your iPad

You can also get stick-on plastic filters from LowblueLights.com as well.  This plus f.lux plus turning the brightness well down makes your ipad totally safe to use at night.  The challenge is these filters are stickers, so they don’t come on and off very easily.  I've had to designate this iPad for using at night time only, since the filter blocks out too much light for it to be usable during the day.



There you go, just a few little gadgets to help you use your gadgets.   Happy sleeping.


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Jason Freedman
tag:humbledmba.com,2013:Post/679859 2014-04-21T16:35:37Z 2016-09-20T07:52:37Z Five Paragraph Essays

In my freshman college class, I had to do a peer review of another student’s essay.  It was on King Lear and the prompt was:  What was King Lear’s fatal flaw?

I was a good writer in high school, and I had studied King Lear in my AP English class.  As I read through my partner’s essay, I was astounded at how awful it was.  He was a smart guy.  Not just book smart but also clearly intelligent and persuasive as a contributor in class.  But this essay lacked so many of the fundamentals. 

In my review, I commented how he needed to better define the thesis statement out front so that the reader would know the purpose of the essay.  Likewise, he needed to have clear topic sentences to each paragraph so that each of his examples would be tied together. I noted that the concluding paragraph needed to tie the thesis back together and link to his initial introduction in order to leave the essay whole.

It was surprising to me how he could be missing such simple fundamentals. I told him to work on the basic structure before we tackled the actual content.


A couple of days later Professor Wheaton called me into his office.

“Jason, I read your review of your partner’s essay. It was a thoughtful attempt, but it was not what I’m looking for.”

I was a little stunned at first.  He continued.

“What was the name of your high school English teacher?”

“Mrs. Streeter,” I replied.

“AP English?”


“5 on the exam?”


“Okay. So this is going to sting a little, but I need to help you un-learn high school writing. I don’t want to demonize Mrs. Streeter, because it’s in fact not her fault. You learned how to write the perfect five paragraph essay, didn't you? Because that’s what the AP exams test for.”

“Yeah,” I replied cautiously. “Is that not what you wanted?”

“Jason, I asked you to dissect King Lear. I've read this play 25 times, and I still can’t make up my mind about King Lear.  I have a Ph.D. in English literature and I teach Shakespeare for a living, and I can’t for the life of me make up mind what to think about King Lear. It’s his complexity that makes him so timeless. So in short, no, I did not think you could explain King Lear in a five paragraph essay. What I wanted you and your partner to do was put some real thought into the character of King Lear and write me an essay that helps unpack all of that. It could take you 5 paragraphs; it could take you 14 paragraphs.  The structure is unimportant.  Your writing should simply reflect the depth and clarity of your thought.

Fast forward to today. It’s time to leave Mrs. Streeter’s five paragraph essay behind.

The medium I use to write is now the blog post. There is no format that is perfect for a good blog post.  Sometimes an interesting post will start with a story or maybe a question I’m trying to answer. Some blog posts will get straight to the point.  Often I’ll try to include a set of tips at the bottom, but only if that makes sense for that particular post.

I bring this up because I talk to a lot of people who would like to do more blogging.  But when I read their drafts, I’m shocked to be looking at five paragraph essays again – smart people writing in overly formulated ways.  Locked into a high school level of writing.

So I wanted to share my one trick for helping people become better writers.  It’s really simple:


To become a better writer you have to stop writing and start speaking.


For a lot of people (obviously not all), it’s much easier to get  thoughts across naturally by talking about a subject instead of formally writing. I started doing this a few years ago, and I now dictate one hundred percent of my blog posts.  I’ll go on a long walk with my phone in my pocket, the voice memo turned on, and I’ll simply talk through a subject that I've been thinking about.  I then email the audio file to have it transcribed by a virtual assistant and Booyah!  I have my first draft.

And while editing and rewriting will occur from there, I’m far better at getting to a decent draft using this method than if I were to sit down at a coffee shop and try to write it out from scratch.  I encourage you to give it a shot.

If you want to get into blogging and your first few posts are coming out like five paragraph essays, try dictating a few.  You won’t necessarily get it right on the first try, but you may find that “writing” actually becomes enjoyable.

Discuss on Hacker News.

Jason Freedman
tag:humbledmba.com,2013:Post/678334 2014-04-16T23:33:49Z 2015-09-15T20:42:40Z Email Introduction Etiquette

If You Are Requesting An Introduction To Someone


Let’s use this scenario:  Joe the Founder is asking Mark the Advisor to give him an introduction to Suzanne the Investor. 

Mark just agreed to make the introduction on your behalf.  Joe should make it super easy for Mark to send the intro:


Thanks Mark. I’ll send you a fresh email now that you can forward on.


And then Joe should send a brand new email which includes everything he wants Suzanne to see:



Thanks so much for offering to introduce me to Suzanne the Investor. 

I want to tell her about my new startup Instacolor. It’s Instagram meets Color but for videos.  We have amazing traction growing 20 percent month over month for the past four months. We are currently doing 50,000 uploads a day and we’re raising a seed round.


Joe the Founder

Recent Press: Techcrunch, PandoDaily, The Next Web


The reason you send a fresh email is that you want Mark the Advisor to be able to forward it from his mobile phone without having to delete all the content from your previous conversation.  This also gives you a chance to succinctly describe your startup exactly the way you want it to be heard. As always, you should obey the Emailing Busy People rules and make sure that your email is super short, very clear and makes a specific ask.


If You’re Requesting An Introduction On Behalf Of Someone


So now, Mark the Advisor will introduce Joe the Founder to Suzanne the Investor.

Should he just cc them both?

No!!!  That’s rude to Suzanne because it traps her into the conversation. Instead, Mark should forward the email from Joe with an intro request on top. It could be something like this:



Would you like to be introduced to Joe the Founder who runs Instacolor? I promise you it will be worth your time.  See below for more details.


Mark the Advisor


If Suzanne receives this email, and she trusts Mark, she’ll almost certainly say yes. But she still has the opportunity to say no.

Often times Mark The Advisor won’t be so enthusiastic though. Instead he might say something like



Joe the Founder asked for an introduction.  See below.



Now Suzanne the Investor gets to make her own decision. And if she decides it’s not worth her time, she gets to allow Mark to make the pass.

If she is willing to take the meeting, then…


Once The Introduction Is Made


Mark The Advisor will send a short email to both Suzanne the Investor and Joe the Founder and say:


Suzanne, please meet Joe and vice versa. You guys will enjoy chatting.


At which point, Joe should respond and move Mark the Advisor to BCC and say:


Thanks Mark (moved to bcc).  

Suzanne, great to meet you.  Are you available to meet…




That, my friends, is proper email etiquette for requesting introductions.  Whether you’re interested in commercial real estate, startups, or anything else…please use it.


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Jason Freedman
tag:humbledmba.com,2013:Post/675935 2014-04-10T20:31:08Z 2015-09-15T20:43:23Z Absurdly High Valuations

Things certainly are warm in the startup world these days.  We have multi-billion dollar financing rounds, or rumored financing rounds, for Uber, Snapchat, Pinterest, Spotify and Dropbox.  All told, those five companies are worth over 20 billion dollars.

Actually, I didn’t quite say that correctly.   And it’s worth a bit of a discussion why.

The only time a company is technically worth a certain amount of money is when a hundred percent of its shares is purchased in a private transaction like a merger or an acquisition, or a percentage of their shares are floated on public markets, as in an IPO.  In both of those scenarios, each share of the company is worth the same as the next.

If I buy a share of Facebook stock (or any public stock) and you buy a share of Facebook stock, both of us retain the same value even as Facebook stock changes.

That’s a big difference between a true exit like an IPO or an acquisition and what we’ve seen recently with these high valuation financings. Because in a private financing, the valuation that is reported represents the price that investors were willing to pay for the most recently issued series of stock.  And the shares from that particular series of stock are different from the rest of the shares in the company.

In addition to various voting rights and restrictions, each series of stock usually comes with its own liquidation preference. For the uninitiated, liquidation preference  means that when a company is sold for less than the most recent valuation, those with a more senior liquidation preference get their money out first.

When you look at the rumored Snapchat valuations of over 3 billion dollars, it’s difficult to understand how an investor can think that Snapchat is worth that much.  Because the truth is, it’s not. Those rumors, even if true, don’t actually value Snapchat at 3 billion dollars.  To be precise, they are bidding on a price per share of a specific series of stock.  As matter of common discourse, we multiply that number by the total number of shares outstanding and call that a valuation.  But the difference still exists and it’s important.

Regardless of what we call the valuation, who’s to say whether the investors setting these valuations are correct in placing their bet?  It is worth taking the time to understand what risks these late stage investors actually face.  It may just explain why they’re able to stomach such high prices.




If I put a hundred million dollars into Snapchat today at a 3 billion dollar valuation, three things can happen:


Scenario A – BIG WIN

At some point in the future, Snapchat IPOs or gets purchased for more than 3 billion dollars. I reap the rewards through an appreciation of my stock price.  That’s what happened to everyone who invested during Facebook’s long run up.


Scenario B – SMALL WIN

Snapchat gets bought or IPOs for less than 3 billion dollars, but more than I invested in the company.  I’d actually do just fine. It’s not the result I was hoping for, but it’s actually not bad.  I get a hundred percent of my money back (assuming I’m the most senior investor) plus I also earned interest on my money every year.  While the interest rates vary, often they are as high as 8%.  So basically, my investment in Snapchat looks more like an interest bearing bond than anything else.


Scenario C – LOSS

It goes bankrupt or sells for less than the amount I invested in the company.  I lose my money along with everyone else.




And now things start to look a lot more sane from an investment perspective.  With acquisition offers already rumored around 3 billion dollars from Facebook, it’s hard to imagine a world in which Snapchat dies so dramatically such that that the acquisition value dropped below a hundred million dollars.   I won’t say it can’t happen – but that’s effectively the bet I’m making as a late stage investor.

So now you can see why these valuations get so high.  It’s because the risk profile of the last money in is actually pretty low.  They can afford to get into these bidding wars because they have the confidence that they are likely to at least get their money back, and yet they still get upside exposure if things go extremely well.




I bring all of this up because I feel like our tech world is under the microscope again. The rest of the economy is struggling to find its momentum.  These people, watching from a far, have a strange mixture of envy, fear and disbelief.  They applaud our innovation.  They invest in our IPOs.  They worry that we’re in a bubble and that it will pop.

The way bubbles actually occur is not simply based on high valuations.  Fundamentally, bubbles need the mechanics of a ponzi scheme in order to exist.  A bubble can occur when speculators invest with the belief that a sucker will come along after them to buy the stock at a higher price.   The bubble pops when those suckers get tricked one too many times and then an incredibly painful game of hot potato takes place as everyone realizes they’re holding worthless stock.

All of the firms making investments into the Snapchats and Ubers of the world are sophisticated private equity funds with capital pools so large they can afford to take large risks.  After our little discussion, you can now see that their bets are actually not quite as high risk as commonly thought.

No, the real danger still comes later when the public markets get involved. When those retail investors with their mixture of envy and disbelief try to cash in on something they don’t understand.  That’s when we should be nervous.

Our friends at Mattermark recently pointed out that current tech IPOs are no where near where they were at the height of the bubble:


So for the time being, root for our friends and their absurdly high valuations.  Their continued success is good for all of us.  And while it’s fun to go back and forth about whether Snapchat is “worth” $3 billion or not, I wouldn’t lose too much sleep over it.  As long as we keep pumping out good IPOs, we’ll be fine.

Discuss on Hacker News

Jason Freedman
tag:humbledmba.com,2013:Post/615685 2013-11-04T15:13:46Z 2015-09-15T20:43:41Z Hacking Public Education

This post will be a bit of a departure from what you guys are used to seeing from me, but it’s super-important to me personally, and I wanted to share it with you. 
I’ve watched in admiration as my brother Andrew Freedman has worked in politics the last few years.  My brother is a campaign director of Colorado Commits to Kids, which is an amendment in Colorado that fixes Colorado’s educational system. If you are at all interested in fixing public schools, not just in Colorado specifically, but throughout the country, I think it will be worth your time to read this post.
The public education has some truly massive underlying problems. Hopefully most of you by now have seen Waiting for Superman. This clip below really got to me:


What Waiting for Superman did is it helped bring into the public sphere of debate that fixing education is not just a monetary issue.  It’s not just a try harder issue.  You can’t address public education unless you address the fundamental problems with how we hire, pay, promote, and fire the teachers that teach our kids.  The problems just feel so intractable.  And no state ever seems to make enough progress to prove their model is better. 
For maybe the first time ever, one state has taken a swing at hacking public education in a truly comprehensive way.  It’s Colorado.  It’s Amendment 66, and they’re calling it “The Grand Bargain” because for the first time, anywhere, they got both the reforms right:

— PAYS for school reforms including a revised teacher-tenure framework
— COUNTS students throughout the year, instead of on a single day, so head-counts for funding are more accurate.

And the funding right:

— INCREASES state school funding by about $1 billion a year. 
That is virtually what all of Waiting for Superman was requesting. So how did Colorado get it done?  Well, they deployed a really unique mechanism that hacks their own system. They got the legislature to approve a bill that puts all the reforms into place, but it only goes into effect if it’s funded.  And then they put the funding mechanism in the hands of the voters.  
If Amendment 66 passes, it will become the blue print for solving education problems in every other state. It’s that big of a deal.  The NY Times just made that point:
Arne Duncan, the nation’s education secretary, has said that the success of Amendment 66, which is what voters will weigh in on, would make Colorado “the educational model for every other state to follow.”
The vote is Tuesday, November 5.  The referendum right now is polling 50/50.  Those that are against the referendum generally cite the tax increase as their biggest complaint.  Not a single income tax increase has passed in Colorado in over 20 years.
Proponents generally fall into two different camps:  those that are pro-funding public education and see Colorado’s 40th position as something that needs to be improved no matter what, and those that are philosophically in favor of the types of reforms spelled out in Waiting for Superman
I fall into that latter camp. I think there is a real chance the Colorado’s system could change everything. So really what is at stake is not just Colorado’s educational system, but potentially decades of reforms in every other state. 
And that’s why this is such a good hack. It’s a chance for all of us in our own states to see a truly grand experiment in education take place. And if there is anything we need nationwide, it’s more big swings at fixing a system that has been broken for way too long.


We need to make sure that people we know in Colorado go out and vote. It’s a mid-term election year so the voter turnout is predicted to be low and generally in mid-term cycles the youth count is especially low.
This is one those times when liking something on Facebook actually could matter. So at the very least, go like the Amendment 66 page on Facebook, as well as share a bunch of their videos with your Colorado Facebook followers.  With the election tomorrow, we can actually play our part and reach out to our friends directly – like right now, and remind them to make sure they got out and vote YES on 66 tomorrow.
Let’s do this.

Jason Freedman
tag:humbledmba.com,2013:Post/615565 2013-11-03T17:04:14Z 2015-09-15T20:44:09Z A simple, no brainer approach to patent trolls

Patent trolls are back in the news.  Apple and friends just declared war on Google/Android.  Yuck.  I wish those guys acted like role models.  I guess that’s too much to ask.  But as much as I hate all of that, I really hate what patent trolling does to startups like mine.

All of the work we’ve put into our company has come from our own heads.  We’ve done our best not to infringe on anyone else’s idea, and fortunately we haven’t been patent trolled yet.  I mentioned this to a startup friend of mine recently and he said, “Sadly it’s only a matter of time.” And it has nothing to do with how careful you are to avoid infringing on other people’s IP. Patent trolls only look for companies that are doing well, and they want a piece of it.  It’s not if, it’s when.

This whole patent shit show just sucks.




Here is what I dream will eventually happen:

I want the US Congress to reform the way patents work in our system so that patent trolls don’t exist.  Currently, this is our best shot.

But I’m not holding my breath.




In the meantime, here is what I want right now:

I want patent troll insurance.


This is a no brainer.  In a world that’s gone crazy, I want some protection.  If an insurance company came in and charged me a monthly premium for patent troll litigation protection, I would happily pay it.  And I bet so would many others. And I would want them to put into the policy that the insurance does not cover settling. And then I would want them to give me a little badge I could put on my website that says, “Protected against patent troll litigation,” so that any patent troll that comes after us will know that they are guaranteed to face significant legal battles with no chance of settling.


I’m not the best one to pull this off (I am a little preoccupied with commercial real estate). But I bet if we, the startup community, show enough interest, some of our friends in the insurance industry will jump on this.  I would feel much better knowing that for a fee, my startup is not fundamentally at risk.

What do you think?


Discuss on Hacker News.

Jason Freedman
tag:humbledmba.com,2013:Post/615564 2013-11-03T17:02:39Z 2015-09-15T20:44:57Z Winter is coming

I struggled last winter.

A few months past raising my Series B, 42Floors felt stalled.  I felt stalled.  This wasn’t how it was supposed to feel.  Even with an awesome team, plenty of money in the bank, and the commercial real estate industry welcoming us…everything just felt impossible.

But now we’re rocking.  The site is super fast.  Features are shipping incredibly fast.  Team is uber motivated.  And users are responding.  The metrics are up.   It’s  a joy to update investors with so much good news.

What a difference a few months makes.




This isn’t a post about a miraculous startup turnaround.  In fact, there was no turnaround.  All that happened is the normal ebb and flow of startup growth. Sometimes you get stuff right, sometimes you get stuff wrong.  Iterate and continue.

This is a post about our shift in mindset.  Or at least mine.

The San Francisco Indian summer is coming to an end.  The days have been long.  We’ve had several months of warm weather and sunny days.  And I see optimism and hope everywhere.  I feel optimism and hope.  It doesn’t surprise me at all.  I make the same observation every year.




I first found out about my seasonal affective disorder during high school.  In both my junior and senior years, I was shocked at how nothing seemed to be going my way during the months of November through April.  I remember how purposeless it all was.  Those were the months when my grades suffered.  Those were the months when I fought with my parents.  Those were the months in which I lacked passion to be the person I wanted to be.

But the most amazing thing would happen each year.  As summer came around, the fog would lift, my mood would brighten and almost magically life would get better.




I’ll step back for a second for those of you who are not familiar with seasonal affective disorder and give you the briefest of overviews.


Seasonal affective disorder (also called SAD) is a type of depression that occurs at the same time every year. If you’re like most people with seasonal affective disorder, your symptoms start in the fall and may continue into the winter months, sapping your energy and making you feel moody.


I urge you not to be too afraid of the words disorder or depression.  In fact, just think of it as the winter blues, which affect us all.  And all seasonal affective disorder is, is a bit more of the winter blues.

I’ve been waiting to write this post for several months now because I wanted to write it when everyone was really clear in their heads, including me.  I feel like last year’s winter was really tough on the startup community.  We lost a couple of our own to suicide.  I don’t know either of them close enough to comment on them specifically. But I do know that many of my friends were fighting with winter depression last year.  And only a few them knew how to deal with it.




For anyone that knows me personally or has read my posts on sleep, you know that I wake up to extremely bright lights every morning. I’m not talking about a simple sunrise alarm clock. My lights are so bright that they actually alter the chemistry of my body.  With only 30 minutes of exposure in the morning, my uber-bright lights stimulate serotonin within my body and that, along with some vitamin D3 supplements, is my antidote to seasonal depression.

We do so much damage to our bodies by being inside most of the time, and that damage is compounded in critical ways during the winter months.  The light your body receives through office lighting is not nearly bright enough to replace the rays of direct sunshine.  It only actually takes about 30 minutes of bright direct sunlight to stimulate serotonin.

If you think back to last winter, how many days in a row did you go without getting at least half-an-hour of direct bright sunlight?  I would love to recommend that everyone just make sure that they spend time outside in direct sunlight, but what I found is that while you’re in the midst of seasonal affective depression, you are less motivated to try to make it better.  The haziness in your eyes is simply too blinding.  So that’s why I waited until now to post this because if this is resonating with you, now is the exact time to act.  With the memories fresh in your mind, prepare yourself for the upcoming winter.


How to Beat The Winter Blues


Read up

If any of this post has been new to you so far, you have a duty to yourself to do your own research.  I would recommend starting herehere and here.  If you start to feel like this stuff is too clinical, read about it from your entrepreneur peers like Brad FeldSteli Efti, and Allie Brosch.


Buy some lights

You want to get lights that are at least 5,000 lux and preferably 10,000 lux.  I recommend checking out Biobrite – that’s your first stop with the Per3 and the Philips light products as secondary options.  Anything that doesn’t explicitly say it is either 5,000 or 10,000 lux is not going to do the job of stimulating serotonin.


Check your D3 levels

Most Americans are chronically deficient of vitamin D3 and there is very little harm to taking a supplement.  You can buy them at any grocery store or Amazon.  Getting in the habit of taking one every day, especially if you’re someone that’s prone to any type of depression.  You can also check your actual levels with your doctor.


Make your exercise routine dependable

Did you exercise straight through your winter depression or did it fall away?  I’ve always found that the only exercise routines that work while I’m also feeling lethargic are the ones that involve some sort of social commitment – team sports or group workouts.  Those are the type of exercise routines you want on your side.  Anything that relies on individual motivation can fail on you.   At 42Floors, our job is fixing commercial real estate search.  But maybe the best part is that we offer group workouts everyday.


Plan a beach vacation

If you know that the winter always gets to you, plan a vacation from it.  A simple one week vacation to somewhere warm (and more importantly, bright) will often be enough to snap you out of it.  And once you get a little reprieve, you’ll be able to gain some perspective and start on all these other things that will help get you back on track.


Beware of fights with family, friends and coworkers

In each of my high school depressive episodes, I fought with lots of people around me.  At the time, I didn’t feel depressed.  Because nothing was ever my fault.  I felt oppressed by all these people who just didn’t get it.  Now, I can see though that all that was really going on is the days were short and I wasn’t getting enough D3. So let this be a little trigger that says if you’re fighting with the people around you and it’s winter time, the entire problem may simply be not enough sunlight.


Don’t suffer in isolation 

My therapy is blogging.  I’ve learned to share my thoughts openly and it has released tremendous pressure.  It’s not for everyone.  I can tell you now that writing this post wasn’t easy.  For most, simply talking to a friend will help.  But here’s the real trick.  If you’re the friend of someone that you can see is suffering–you have to be the one that approaches them.  Go for it.  It will be a little awkward, but I promise they’ll appreciate it.


By the way, now is the time.  Not three months from now when you won’t be motivated enough to do something about it.  Build the habit now.  Winter is coming.



Discuss on Hacker News

Jason Freedman
tag:humbledmba.com,2013:Post/615562 2013-11-03T16:57:13Z 2015-09-15T20:46:02Z Learn on someone else’s dime

I remember being a senior in college and thinking about my possible career choices. After 16 years of school, I was just so excited to be working and out on my own.

But as I looked at all the jobs offered to me, none of them seemed glamorous enough.  I wanted to change the world, not be on the ground floor of some massive corporate ladder.  I’d worked way too hard filling myself with all this knowledge and experience to be working for the man.  I also kind of wanted to get into startups.  Not just into startups, I wanted to be running the startups.  But I really didn’t have a clue how, nor did I have an idea.  I felt lost.

And that’s when my dad gave me this little tidbit of wisdom:

Learn on someone else’s dime.


That was just the little nudge I needed to go look for an entry level startup job.  I found an incredible one—as an intern for a site called MocoSpace in Boston. At the time it was the largest social network focused exclusively on mobile, and I joined the company right after it had received its first round of investment from General Catalyst.

I pretty much did whatever the founders or the head of product needed me to do.  At one point, I was needed to go check out every competitor in the space and screengrab everything that happened on their site.  It was so mundane. I didn’t yet have the product expertise to design my own products, so the best I could really do was gather all the information so that the rest of the team could use it.




But while working for MocoSpace, I soaked up all the goodness of being in a startup.  I was there as we brainstormed new product ideas and got to watch all the different pieces of the team put them together.  Ideas spiked out, engineers working on them, feedback from customer service – the whole little machine of a startup was taking shape in my head.

I was there as we celebrated small wins like a conversion uptick on our login page.  Something I had never even thought people cared about.

I was there as our customer service team grew from 1 person to 5 people and Gmail started to fail them.  And then just as quickly resolved by installing a ticketing system.

And what made all of this so interesting was that the company was going through hyper growth.  The whole social networking industry was in its infancy, so every little decision mattered.  Because the company was growing so quickly, the problems we encountered changed day by day.  After a few short months the entire company had changed before my eyes.  It literally doubled in size.  And finally, feeling that I had learned enough, I decided it was time to leave and start my own startup. A few months later, we founded OpenVote.




Throughout each of my last three startups, little bits of wisdom gained during my entry level MocoSpace experience have been important.   MocoSpace was a really good company, so I didn’t learn a whole bunch of things not to do. And although they didn’t grow to the size of Facebook, they’re still a really strong company and I proudly copy as much as I can from how they built their team.  I’m so glad I had the opportunity to learn from them before going out on my own.

So if this resonated with you, here are a few tips for deciding which entry level job will be best suited for you.


Tips for Picking an Entry Level Startup Job

Pick a rocket ship

The single most important factor on whether you’ll have a good experience is whether the company you join is exploding with growth or not. Because when companies explode with growth, everyone who is entry level today will be experienced leadership three months from now.  There will simply be so many opportunities to get things done that you will have the ability to grab hold of whatever experience you want.  When a company is stale or declining, the inverse is true.  So irrespective of everything else, pick the company most likely to succeed.


Get in early

The best learning is when you get to see the company grow around you.  If the company already has a hundred or two hundred people, it may still be a startup, but it is really a late stage startup, and all of the tremendous learning opportunities are already gone.  When you join a company that size, you’ll get the benefits of a really good training program and you’ll surely work with outstanding people, but you won’t be a huge part of helping the company grow.  When there are just 25 people or less, nothing will be created for you and half your time will be spent building the company itself.  The risk goes up, but it’s certainly worth it.


Teach yourself a new industry

All too often I see young job seekers limiting themselves to products they’ve used themselves.  If you’re fresh out of college or even a few years into your career, don’t expect that you’ve already had your most important work experiences.  Just because you’ve done an internship here or a job there doesn’t mean you are already pigeon-holed into one industry.  At 42floors, almost all of us knew nothing about commercial real estate before we started, but each person that joins has to learn the industry quickly.  It’s actually a great way to start a job because you approach each problem with a fresh set of eyes.


Work with fabulous people

The actual job that you do may or may not be the perfect fit in the long run. A lot of our entry level jobs at 42floors are account management, which means spending a bunch of time on the phone. While you clearly need to be able to do that job, it doesn’t mean that is what you’re going to do the rest of your life.  Most of what you’re going to learn is through osmosis of the people around you.  So if you’re not blown away by everyone you meet during the hiring process, look elsewhere.  You don’t want to be learning bad habits, especially because you might not know at the time that they’re that bad.


Do one hour of research before you apply

Not only do you need to use the product and the competitor’s product, but you need to research the company itself – who the founders are, follow their Twitter accounts, read everything in the media. For one, it will help make you much more likely to get the job. But two, you want to really have a sense of who the company is because their story is going to become part of your story.  It only takes an hour.




And now a shameless plug.

42floors, my startup, is now hiring for a bunch of non-technical entry level positions (we’re always hiring hackers).  Our site is blowing up right now with massive demand that we simply can’t keep up with. We’re hiring as many account management specialists and sales people as we can – all entry level positions.  For those of you who don’t know our site, it makes it easy to search for commercial real estate.   And over the next year we need to reach out to virtually every landlord and broker in the U.S.  We’re going to build a really big team of people to do it, but right now the account management team has just a single person.  It’s going to be an incredible experience for whoever joins the team right now.  Not in 3 months, not in 6 months, but right now because right now is when you get to be there as part of the foundation.  The whole system doesn’t really work yet.   You’ll have to figure out everything as you go along. Not just like how to do the job, but also how to build up the team around you.

Megan started just last week and she is already busy interviewing and hiring for people to work with her.  You’d be doing the same thing. And all of a sudden just days into an entry level position you need to become good at interviewing because whomever you hire may work with you for the next several years.

Right now everything is run off a collection of inconsistent Google docs.  We just signed up for Salesforce but haven’t installed yet.  So just days into your job, you’re going to have to help us figure out how to make everything organized and efficient.

This team is going to grow to 20-30 people and we need your help to support that.  Right now our office is way too many desks jammed into a 2,500 square-foot unit (which by the way is still stunningly awesome – see the pictures here).  But we just signed a lease for a 7,500 square-foot kick-ass office in Soma, and we’re going to need your help to build it out for your team.

Startups are usually run totally flat and ours is an extreme example of that.   There will definitely be people to support you, but you have to be someone that is not only capable of figuring things out, but prefers it that way. And you have to be good at the job itself; you need to be able to pick up the phone 75 times a day and convert 90% of the time.  While you’re trying to master that, you need to be good at helping train the next person, and once you realize that that doesn’t scale, you also have to be good at developing a training program – and very quickly your job has changed three times.

It doesn’t matter whether you know about commercial real estate or not. We’ll teach you that part.  And it doesn’t matter whether you have experience in sales or account management. We can help you with that part as well.  But you need to love all things startups. You need to be super motivated.  And if you are those things, you should totally apply for a job here.



Discuss on Hacker News.

Jason Freedman
tag:humbledmba.com,2013:Post/615561 2013-11-03T16:52:31Z 2015-09-15T20:47:05Z How about less blogging and more work on your company?

In one of my recent posts, I got this little snarky comment on Hacker News:


Hey hotshot.  How about less blogging and more work on your darn company?


Oh, trolls.

They used to really get to me. I used to try to think ahead about how I might get trolled so as to avoid it – as if that were possible.  It’s not.  Trolling is just a reality of an internet where anyone is allowed to post anything.  If you want to push your message out to many people, there will inevitably be some whose sole intention seems to be to get a rise out of you.   It’s like trying to avoid getting honked at while driving in rush hour in New York.

But this one actually made me smile.  First and foremost, I responded courteously to the troll.  It’s the most effective way to disarm them.  But it also got me thinking, is it really in the best interest of my company for me to be blogging? I know I love doing it, but is that enough?

We made the decision here at 42floors that anyone can post on our official blog if they write something that’s valuable to our users and it doesn’t have to be directly related to commercial real estate.  Our users are in large part startups looking for office space.  I don’t write about commercial real estate here because frankly not a lot of people want to read about commercial real estate.  We have an extensive educational center with well-written posts about  commercial real estate, but the primary driver of traffic there is SEO.

This blog is mostly about startups.  That’s what I know and that’s what I like to write about.   It’s not work for me and I don’t hire people to help.  I love writing and startups are the subject (right now) that I’m best at writing about.

But if I were to be totally objective about this:  What is the actual value of our blogging to 42Floors?

So here we go…


How blogging helps my startup


Blogging drives traffic

My posts get anywhere from 10,000 to 50,000 views with some duds and some homeruns.  While the conversion rate of people who read my blog, and then search for commercial real estate on our site is admittedly pretty low, it’s definitely not zero.  Most of our users in the first 12 months were tech companies searching for office space.  And for our company, which has a high value per transaction, getting tens of thousands of users at the top of the funnel is actually pretty helpful.  We also noticed for a long time that a huge number of our first time users searched for “42Floors” on Google.  That means they already knew about our company, most likely from a combination of good PR and blogging.


Blogging got us our initial users

I separate it out because getting the first users is both incredibly hard and incredibly valuable.  I was blogging about 42floors as a startup before we even launched the product.  After our YC demo day, I drew a graph of our tour requests (our primary metric) that went up into the right, and I made it my personal mission to make sure that our actual metrics matched that graph. And because we didn’t have money to spend on marketing, my best tool was writing blog posts.  For those of you who remember my public job offer to Dan Shipper, it should come as no surprise that it happened during a time when every user counted.  And that post generated 100,000+ views.  Which generated enough tour requests to drive our metrics that month. Big win.


Blogging got us our initial investors

When we were getting 42floors off the ground, a few investors reached out to me after learning about our startup through the blog.  Several told me that they used the blog as part of their due diligence effort on me.  Because there’s so little data in the early days, they had to bet on me.  And having already read my blog, they had formed opinions on our potential.


Blogging helps us hire

I write about hiring quite a bit.  It’s one of my most important responsibilities in the company and I’m able to talk about our approaches to hiring in a way that reaches the very people that I would like to someday hire.  Most of the people who have joined us in the past year already knew me through my blog.  They had followed the 42floors story long before we met.

It even provides a great filtering mechanism because the people that reach out to us, having read this blog, generally already want to work with us; and those that don’t like it will obviously never apply for a job here.  We’re not for everyone, and it’s nice that people self-select.


My team likes to blog

I encourage, but never require that people write their own posts on the 42floors blog.  Darren Nix wrote an incredible piece on a sneaky tool being used to steal people’s information.  It got 700 points on Hacker News.  Because we don’t restrict our blog to just product updates, it gives everyone on the team an outlet for their own creative efforts.  Ben’s post on his design process was his first ever blog post that engaged the startup community and it was incredibly well received.  It was an added pat on the back for him after he had worked so hard designing our mobile app.


My board members like the blog

I am incredibly candid in my writing.  When shit’s not going well, I don’t try to hide it.  My investors called me up after I wrote that post wanting to know how they could be helpful and applauded me for my efforts to fix the problems we were facing.  They like backing an entrepreneur that is engaged in the startup community because they know that networking, hiring, serendipity, and so much more flows through.  We often discuss noteworthy posts and they encourage me to keep writing.


Blogging rocks for SEO

As Darren always tells me, a link is a link is a link.  Our blog posts have been syndicated on Inc MagazinePandoDailyBusiness InsiderLifeHacker, and many more.  We’ve had 10 of our posts go viral, where they inspired follow-on stories, all of which linked back to 42Floors.  Our overall SEO results are far better off  because we have so many high quality links from high PageRank sites.




But more than anything, I blog because it brings me joy.  When I don’t enjoy it anymore, I’ll stop.  Here’s my response to the latest troll on Hacker News:

I blog because I love writing.  Writing startup stuff for the HN community gives me purpose to that writing.  It’s a sweet bonus that many of our users are on HN, but that’s not actually my top motivations.  It’s just because I like doing it.



And I wanted to thank all of you for reading what I write.   Please keep reading. Please keep commenting.  And yes, please keep trolling…


Discuss on Hacker News.

Jason Freedman
tag:humbledmba.com,2013:Post/608032 2013-10-11T16:17:51Z 2015-09-15T20:50:16Z 100 day goals

People usually don’t believe me when I tell them how fast it took to build the first version of Flightcaster.  Remember, Flightcaster was not a trivial piece of technology. We were one of the first production applications to use Clojure.  And, we launched (insanely I might add) with a research infrastructure, website, iPhone app and Blackberry app simultaneously.  And all of this was done in just over three months, from first line of code to launch.

At the time, it was the most productive any of us had ever been in our lives.  It was awesome.

We were in the summer 2009 Y Combinator batch.  One of the truly powerful aspects of being in Y Combinator is that the date of demo day is set for you.  Paul Graham doesn’t go around asking each startup when would be a convenient time for them to be ready.  The date is set and every company has to do what it takes to be ready in time.

This concept of setting the time limit first and adjusting the scope second is really powerful.




I don’t know why we ever stopped doing it.

Nothing was really accomplished in the hundred days after demo day.  Oh, yes, we were absolutely dealing with all the technical debt we had cost ourselves, but the reality is we didn’t accomplish very much the hundred days after that either.  I don’t care how much technical debt there was, it was not enough to justify a drop of productivity lasting six months.

Without any clear ambitious goals, we simply drifted towards a less productive state – scope would be added way too easily, design iterated on too many times, code perhaps more polished than it needed be.  The result was we went from a sprinter’s pace to a jogger’s pace, and when our product ran into trouble we were simply too slow to react.




When we got into Y Combinator for 42Floors, we had no code written.

The entire first version of 42Floors was built in that three-month period.   We built a complete platform for commercial real estate in under 10 weeks.   Once again, we achieved a level of productivity that had seemed impossible at the beginning.

Setting deadlines first and then choosing ambitious goals is the key.  The deadline becomes a forcing function that wipes away distractions.  There’s simply no time for extraneous features.  Failed experiments end much earlier.  Hacked together solutions get tested much faster because there’s no time to build the scalable version.




After Demo Day this time, I bought a 100-Day Goal calendar.  And it worked.  It worked incredibly well then and still does.  We’re now on our 6th consecutive 100 day countdown books.

So, if you find yourself suffering from not enough direction, I highly recommend you give this a try.  Here are a few suggestions for doing it the first time:



Tips for Creating a 100 Day Goals


Set the deadline first

This is seriously the most important step.  If you think about scope and then try to predict a deadline, you are always going to be in this mindset of time estimation.  But when you pick the deadline first and then try to pick the goal, you begin to see how ambitious you can really get.


Tell everyone

Once we decided that the New York launch was our hundred day goal, we told our investors and partners about the launch date.  We didn’t mention that it was part of some hundred day goal program; we just told them with certainty when the date of the launch would be so that they could count on it, which in turn put even more pressure on us to make sure that we hit that deadline.  When you talk about the efficiency of a team working together, it really helps when everyone believes the deadline will hold – and nothing like external pressure to help with that.


Make it front and center

Deadlines don’t work unless people can see the days.  What I love about this countdown booklet is that we have this morning ritual of ripping another day off.  It’s not buried in a monitor with all our other metrics.  It  serves as this conversation piece for anyone who walks in the office – people want to know what is happening in 27 days, and we tell them.  And in doing so, we remind ourselves that we have a goal to accomplish; we need to get to work.


Delay the wouldn’t-it-be-cool-ifs

We are never short on good ideas.  But good ideas are not what we need; more important is having the discipline  to stay focused.  With our hundred day goal method, we have a real easy process for dealing with “wouldn’t-it-be-cool-if” conversations.  We simply push them to our next hundred day planning session.

And in doing so, this raises the bar on what it takes to introduce a change to the middle of the hundred days.  It’s not that we won’t deviate from our plan – we deviate from plans all the time – it’s that we will only do so when it is actually really important and not just interesting.



When we hit our hundred day mark, it feels awesome.  Alison, our Director of Vibe, plans something big to celebrate; we all go out and take stock of the accomplishment.  The last 20 days of a 100 day segment are really stressful.  Nothing wrong with working hard.  It’s immediately followed by some much needed rest.



We’re in our 6th 100 day countdown book.  I have enough data to say that this system has worked without burning us out.  Give it a try.  Let me know how it works for you.


Discuss on Hacker News.

Jason Freedman
tag:humbledmba.com,2013:Post/605665 2013-10-03T15:23:27Z 2015-09-15T20:54:28Z How to Pull a Jennifer Dewalt


For those of you who don’t know, Jennifer Dewalt just taught herself to code by building 180 websites in 180 days.  The fanfare is coming in from all sides right now from her initial epic Hacker News debut to all the articles and speaking opportunities that are now rolling in.  It’s a regular circus.  It’s the best kind of circus when an awesome person does something awesome and everyone applauds them. 

And it’s not just applause, it’s inspiration.  So many people want to teach themselves how to code and seeing her do this has increased their motivation.  But they get hung up.  They don’t necessarily have 180 days to spend.  And more importantly, it seems impossible to muster up the discipline to do something 10 hours a day every day. 

I can relate to all of you who feel that way.  I’ve been “trying” to teach myself how to code for years.  I’ve read a couple of books.  I’ve built a couple of websites.  I’ve taken a class.  Basically, I’m stumbling along slowly while Jen is whizzing right by. 

So with all that in mind, I thought I’d share a few observations I’ve had while watching her pull this off.  The hope is not necessarily that anyone else will try to do 180 websites in 180 days, but that you may find yourself at least able to accomplish something you did not think was possible. 

So here we go…


How to Pull A Jennifer DeWalt


Brand your goal

Jen didn’t decide to learn how to code.  She didn’t take a few months off to work on a skill.  From the very beginning, she defined the project with its snappy little phrase, 180 Websites in 180 Days. I don’t actually know where she came up with that (Jen, can you pipe in?), but it had such a nice ring to it that it stuck.  Everyone who heard about it understood immediately what she was going to accomplish. It gave the whole endeavor a sense of importance. 


Pursue small accomplishments

One of the really nice things about the way that Jen designed her project is that every day had a beginning, middle, and end.  She had to come up with an idea, research how to build it, and then get it coded.  It meant that at the end of each day she could point to something that was accomplished. 

A tweet went out, a blog post was written, user feedback came in.  These bite-sized segments of work had all this positive reinforcement.  I remember when I was working on Michael Hartl’s Rails book, I would get stuck on a chapter and just give up for a little while.  Eventually, I’d find my way back and persevere through it, but it was a struggle.  I like Jen’s way much better.  She focuses on getting one concrete accomplishment done and then releases it to the world.


Tell lots of people

Having just watched Jen for the last six months, I’ve come to realize how important it is to be public with a project like this.  Just like I get consumed with commercial real estate, Jen got consumed with her project.  And every time she’d come around to the office, we would ask her about it.  We wanted to know what she was building next.  We wanted to figure out what she learned.  We had feedback for her on past websites.  Not only was there all this positive reinforcement, there was also a sense of accountability because she had laid her goals out to us publicly.  When she wrote her epic blog post on day 115, that effectively cemented her resolve to finish her project because she had literally 2 million + people were rooting for her. 


Build stuff you love building

Jen is a natural student of art, always has been.  Whenever I think of websites, I think of functional sites that solve a problem.  But Jen sees an artistic canvas.  I bet if she’d been forced to code a bunch of twitter clones like most ruby on rails textbooks focus on she would’ve gotten bored early. Instead, Jen coded the things she loved which always involves some interesting interplay between colors or movement.  Later, when she already had momentum, she started working on the skills that were harder for her to develop.  I often hear this question when people say they want to start coding, they want to know which language they should start with.  The lesson to learn from Jen is to start with the tool that will help you make something you enjoy making. 


Make For the Sake of Making

One of things Jen has proven with this project is she loves making stuff.  At 42floors we actually look for this quality specifically when we’re hiring.  The best people we hire, regardless of what position, are relentlessly making things – at work, in their spare time, side projects, it doesn’t matter.   Jen didn’t make something that had some specific goal of making money or enhancing her career.  But I would bet any amount of money that this project will help her accomplish both.  She is getting flooded with people that are trying to hire her right now (You should recruit her too!).  This world is always craving for people who make stuff.  So for today, Jen is making artistic one day website with colors that blink on and off.   But tomorrow, don’t be surprised to find her working on the internet’s next big success story. 



And, finally, a quick reminder that every marathoner knows:  you’ll never get to that finish line unless you can get yourself to the starting line.  The hardest part of any project that involves discipline and perseverance is simply getting started. So if you’re looking for a project that will teach you how to code, try this: 


Build one website in one day. 


 Discuss on Hacker News.


Jason Freedman
tag:humbledmba.com,2013:Post/603614 2013-09-23T16:04:49Z 2015-09-15T20:55:10Z How to fake courage

I’m not the most courageous guy. It’s been one of those little hidden truths that has always both haunted me and motivated me.

I remember playing a tennis match for my high school team.   It was overall rather insignificant, but I still remember it.  The rest of the team had split their matches, and I was the last one to finish so it was on me to help the team win.   I remember everyone gathering around my court, cheering me on.   We had tied the set, and we were going into the tie-breaker.

I won’t bore you with the melodramatic details of a 15-year-old’s quest for greatness in JV tennis.  But I still remember the feeling I had as I prepared to receive his serve.  All of my intensity, all my focus, all of my training led me to this one thought:  I wanted him to double fault.   I didn’t see myself successfully beating him on my own—I needed him to fail on his own.

Of course he didn’t.  We played some points – I won some, he won some.  In the end he took the match.

It bothered me then and it bothers me now.  I don’t like the way I stepped up for the challenge.  I was just waiting for him to make unforced errors.  It didn’t feel good at all.




I’ve been that same 15-year-old playing tennis many times in my various startups.  During each investment round at both OpenVote and Flightcaster (my last companies), I negotiated  poorly because I was so afraid of losing the deal.  The acquisition of FlightCaster was the same story.  I had the chance to walk away with a small win and so I took it.  It wasn’t some grand triumph; it was just avoiding failure.

I bring all this up because I haven’t made the same mistakes at 42Floors.  I don’t mean to say that I finally have found courage.  I really haven’t.  At every step along the way for 42Floors, I have been terrified about screwing it up.   But yet, I haven’t made the same mistakes this time around (at least not yet!).   Somehow I have found a way to not be as consumed by fear.

I wish I could say I’ve harnessed some deeper courage to take risks, believe in myself, yada yada yada.

But I don’t actually believe it be true.  I think I just hacked my brain a bit.  I knew a lack of courage was going to be a weakness going into 42Floors.  So I tried a few things to address it head-on.   Hopefully you find a few of these mind hacks helpful.



How to Fake Courage


Define your goal early and stay true to it

Early on, my cofounders and I agreed we would not stop short of fixing commercial real estate search world wide.  We would be singularly focused on building a big, successful company—even if that meant increasing our overall odds of failure.  That may sound trite, but I can tell you it has already impacted dozens of decisions.  My mindset during FlightCaster was to simply not fail.  Every time I could have rolled the dice, I took the risk-minimizing option.

At 42Floors, we’re okay with the prospect of failure. We’ll roll the dice every time to keep our full dream intact.  Investors/employees/customers can smell the difference.  We’ve said this from the beginning.  And in the beginning it’s really easy to say because you have nothing to lose anyway.  Now that our company is off the ground, we’ve simply gotten used to saying it.

Set a really big goal, go after it and ignore everything else.


Avoid isolation

What was so miserable about being on that tennis court as a 15 year old was that it was just me out there alone.

I’ve struggled at everything I have ever done.  It took me years to see this, but I finally see that every other entrepreneur has had the same problems I’ve had.  I did a YC a second time mostly because I wanted that community of peers again.  As I’ve mentioned before, if you can’t get into a YC, make your own.


Believe that you can change

Paul Graham once said the hardest part about being an early stage investor is thatfounders can change.  I was nervous when I applied to YC with 42Floors because I was afraid of repeating the same mistakes again.  But fuck that!  Those types of thoughts are worthless.  Focus on the opportunity you have right now and become the person that can get it done.

I am vastly different founder in this company than ever before.  I refuse to let my old weaknesses haunt me further.


Get a win under your belt

I have to include the acknowledgement here that this post is total bullshit.  I didn’t gain this mindset until we had already sold FlightCaster.  That win gave me a ton of confidence to swing bigger this time.


Don’t ever say you’re crushing it

Every time I hear an early stage entrepreneur talk about crushing it, I know they are fighting demons within themselves.  There’s nothing worse than pretending to the world that you’re doing better than you actually are.  All it does is isolate you even further. One of the most powerful parts of my blogging in the last few years is I’ve been able to share openly how hard things have been.  It’s taken an immense stress off of me personally.




So, to all you founders out there thinking that other everyone else possess some genetic gift of unending courage that you lack.  It’s not true.  They’ve just faked it better.  So can you.



Discuss on Hacker News

Jason Freedman
tag:humbledmba.com,2013:Post/603601 2013-09-23T15:39:29Z 2015-09-15T20:56:43Z How startups should die


When we did OpenVote, a web 2.0 Facebook app company, back in 2007, we were enabling college students to debate issues on their campus.  And in the unfortunate theme of that era, we had lots of people using it but nothing resembling a business model.  And as our cash dwindled down and our traction didn’t explode, I personally faced a crisis.

One of my cofounders had left for an awesome opportunity. I couldn’t blame him.  Our investors had declined to put more money into the company.  I couldn’t blame them either.

I would sit alone everyday working feverishly to try to find any way to save the company.  Amongst a bunch of failed pivot attempts, one opportunity kept creeping back onto the table…

We had our users’ data.

We had over a million confirmed email addresses for a fairly targeted demographic. I had companies calling me interested in purchasing it.  I remember rationalizing with myself why it would be okay to sell the list.  My credit card debt was out of control.  It was a period of my life when every dollar counted and I had this asset.

Would it really be so bad?  Would anyone ever need to know?  Don’t companies do this sort thing all of the time?




We shut down the company a few months later and I moved on. I never sold that list.  I had been close though. I think back on that time every now and again.  What would have happened if it had been ten million email addresses?  What would have happened if the price had been higher? Would I have taken it?

My ethical discipline had been vulnerable.  I know right from wrong, but it hadn’t felt as clear then as it usually does.

But if there’s one thing I am grateful about our OpenVote experience – it is that we decided to let the startup die elegantly.  We paid all of our service providers, which was tough because I had long since run out of investor money.  So to rephrase that – I paid our service providers with my credit card debt.  We closed down all our paperwork thoroughly and correctly.  And I didn’t get tempted into last second shenanigans that I would’ve later regretted.




Fast forward to today.   The deadpool is getting more crowded every day.  That’s part of a healthy startup ecosystem.

I just talked to an entrepreneur who is running a company that is on its last leg (though he is only fifty percent willing to admit it).  He’s raised a couple million dollars, has built a reasonable product, but his efforts at raising another round have just failed and he’s looking for options.

I just found out that he is selling enterprise contracts for software he knows he won’t be able to deliver.

Not only is he going to screw over some customer when they find out that he can’t fulfill his promises, but he is also ruining it for the rest of us.  Additionally, he is screwing his investors who will never back him again when they find out.  I had a phone call with him and I begged him not to do it.  I don’t know.  Maybe I got through, maybe I didn’t.  But all I wanted to convey to him is, “I believe in you. I think you’ll be back with another idea. But for now, die elegantly.”  I hope he does.


Tips to make sure you die elegantly


Share your finances openly with your team

It takes so much pressure off of you individually when everyone is on your team. And, yes, the less committed of your people will leave you when your cash reserves get low.  But the reality is you couldn’t afford to keep them anyway, so at least now you’re not stuck living a lie everyday to people that work around you.


Communicate more to your investors, not less

When you’re dying is the time to communicate the most.  Not only because they might be able to help you with last minute acqui-hire attempts or guidance on how to proceed, but also they might fund you next time if they appreciated your efforts during the tough times.  I remember sitting down with Paul Graham as our startup was failing. I remember how unbelievable difficult it was to get myself to that meeting.  The last thing in the world I wanted to do was to tell him my startup was failing.   It took him 30 seconds to process the failure and then he moved on.  He was so unbelievably supportive and so excited for whatever it was I was going to do next.


Pass the Hacker News test

It used to be called the Wall Street Journal test, but that was more about managing the ethics of bankers.  For us it’s the Hacker News test.  Will you be okay with your every action posted and commented on in Hacker News?  Assume there is no way what you do will be kept secret.


Pay everyone in full

Don’t push your mismanagement onto other people – employees get paid, service providers get paid, lawyers get paid, accountants get paid. Hell, even the IRS gets paid!  There will be many people who tell you that you don’t need to save money for the lawyers.  Screw that. I’m working with the same lawyer on my third startup now, and he’s the best in Silicon Valley.  I shudder to think if I had screwed him over two startups ago.


Pursue interesting acqui-hires

I have already written on how to get an acqui-hire done.  Google and Facebook have set this precedent that acqui-hires can be this awesome cash out opportunity.  That works with a very, very small number of companies. What about the rest of us?  What if you could turn your failure into an acqui-hire with a company that you actually would love to work for?  You won’t make a million per engineer, but you’ll keep your team together.  I will humbly throw my company 42Floors out as an example.  We’re solvingcommercial real estate and we love working with entrepreneurs.  Our entire team is made up of entrepreneurs that have at some point failed their own startup.  There are hundreds of companies like us that are always looking to hire awesome entrepreneurs.



Finally, one last note.  Same thing I say to every entrepreneur that comes to me for advice as they’re on their very last legs.  Welcome to the club! We are a culture that celebrates risk takers.  We all fail at some point.   So while you may feel your startup career is over, you actually just passed your entrance exam.

Jason Freedman
tag:humbledmba.com,2013:Post/601102 2013-09-12T18:51:48Z 2015-09-15T20:57:04Z Startup Common Sense


I had a really interesting conversation with an entrepreneur last week. He is the brother of a friend who wanted to talk about his world-changing idea.  It was so world-changing in fact that he didn’t want to tell it to me without me first signing an NDA.  I gave him myusual spiel about what type of advice startups in stealth mode really need.  Usually at this point I would just politely decline to engage further.

There’s nothing I can offer to someone who is so antiquated in their thinking that they still hold onto the misguided belief that an NDA will protect them. As I said, usually I just politely pass them on, but this time I was dealing with the brother of a close friend.  There was no way for me to easily extricate myself.

He’s a lawyer by trade, so he was more argumentative than most and forced me to defend my opinion on why he should be sharing his ideas freely instead of requiring NDAs.  And the conversation on NDAs turned into he and I disputing other startup philosophies I hold dear.

We talked about launching fast; but he believed in taking his time and making sure he got it right.  We talked about forgetting about scaling until product market fit had been validated; but he knew it was the right product and wanted to scale from the beginning.

And so this conversation went on and on.  And I started to actually enjoy it because this guy was forcing me to find the words to explain these beliefs that most of us in the HN community hold as unquestioned truisms in 2013.  And as the conversation developed, it was also interesting that in almost every case his intuition was leading him towards the exact opposite approach.




There is something about how to do a startup in 2013 that is 180 degrees different from what an intelligent, thoughtful outside observer will intuitively do using their own common sense.  And so, given that I was speaking to a trained lawyer, we started to get fairly abstract.  Here was our little exchange:


Me:  What is the basis by which you are forming your opinions?

Him:  What do you mean the basis?

Me:  I mean, you have very strong opinions about each of these activities even though you’ve never done a startup before.

Him:  I’m using my common sense.  I think through each problem and come up with a solution that makes the most sense to me.

Me:  What if I could prove to you that your startup common sense was categorically wrong?


And then, finally, for the first time in 45 minutes, there was silence on the phone.   For me to prove to him that his common sense in this particular subject was categorically wrong would mean that he couldn’t trust his own mind.  It would mean that his most relied upon tool would be of no use to him.  It’s a terrifying thought.




I know this terror.  In my first startup, my trusted common sense failed me miserably.  I look back on that time and can finally laugh about how awful I performed.  I was so sure of myself.  And yet, I was always so wrong.  I didn’t just come up short, I did everything as if failure was actually my goal.  How could I be so naive?  Or more accurately, how could my intuition be so backwards?

After that failure, I fortunately got into Y Combinator.  And man, YC will get you turned around quickly.  They tore my previously held beliefs to shreds.  It was really tough.




Our lawyer friend here was only reacting to the world of startups that he knew.  He only knew about them after they had been successful.  And when you’re reading about successful startups in Forbes or BusinessWeek, you have a very different conception of what it takes to get one started – a conception so flawed that it will actually lead you to have perfectly incorrect common sense.  That is how I emerged from business school, having only learned about startups through case examples that suffered from a bit too much hindsight.

If you do indeed find that your common sense needs some adjusting, I’ve got a few suggestions.



Tips to reprogram your common sense


Get a great advisor

The very best advisor you could have is someone who has successfully done what you are trying to do and is only 18 months ahead of you.  Not some industry superstar.  Not a famously successful entrepreneur.  Not an investor.  The best pure advisor is a fellow entrepreneur who is just a little bit farther down the road because they are the ones who have only recently gone through the epiphanies that you are currently in search of.


Read up

You not only need to read a few books, you need to make sure you read the right ones. I have six specific books that I recommend every entrepreneur read before they get too deep into their startup.  These books are not only helpful, they are also paradigm shifting and you can read them quickly and know that you are on the right path.


Read Hacker News

Originally, I put here “stay current with blogs,” but the problem with blogs in general is that you don’t know which ones are good and which ones aren’t.  Hacker News is the best community out there for getting a daily curated reading list.  And if you’re not technical, read it anyway; there will be plenty of posts that are relevant to you and can help guide your personal startup education.


Get into an accelerator

Whether it’s YCombinator or 500 Startups or Tech Stars, accelerators are right now the single best way to get your startup started on the right foot.  Not only will you benefit from the advice, you’ll also feel the pressure of keeping up with your peers.  If you can’t get into a top tier accelerator, act as if you did anyways.


Launch your product and talk to users

I probably should have put this sequentially number one because launching is the single best educator.  But I also know that many of you will choose to do absolutely everything possible to avoid launching your product. I know how scary it is to launch your product.  In fact, you should launch your product as early as possible to the point that you are thoroughly embarrassed by its quality so that you can start learning from your users much, much earlier.


Stop taking bad advice

If you’re getting the wrong type of advice, you need to stop it.   The worst advice is never maliciously wrong.  That’s would be easy to spot and avoid.  The worst advice is the advice that is outdated.  Successful people and big company people are especially prone to outdated advice.  What worked in 1998 will not be relevant to your 2 person startup in 2013.



The first step to recovery is admitting you have a problem.  As a fellow confident, stubborn asshole that thinks he’s always right, I know this won’t be easy.  My advisors ripped apart many of my strongest held beliefs.  And I can’t thank them enough.
Discuss on Hacker News.

Jason Freedman
tag:humbledmba.com,2013:Post/600223 2013-09-09T16:08:50Z 2015-09-15T20:57:37Z If you’ve ever wanted to do a startup there is simply no better time than right now.


Enough with the excuses.  Either start your company or don’t, but at least don’t lie to yourself.

There has never been a better time to start a company.  All the software you need is now open source.  It wasn’t like that ten years ago.  Fortunately, the entire technology world has created this incredible software stack that you get to use for free.  It didn’t use to be that way.

The Cloud has abstracted away the need to build your own infrastructure.  To put it bluntly, you don’t need to know anything about servers anymore, at least not in the beginning.  If you can get code that works, you can pay Heroku or some other platform as a service to host it for you.  It didn’t use to be that way.

Social media has created the potential for viral distribution.  It used to be that you couldn’t get anywhere without raising tens of millions of dollars in venture capital in order to help you strike a deal with AOL or Yahoo! so you could acquire your initial users, and even then you would use expensive offline marketing. It’s really true that you can now build an incredible product and people will find out about it through word of mouth.  It didn’t use to be that way.

There are now built-in business models. If you want to charge for your product, you previously had to setup a complicated billing structure.  Now, you can sell your app on the app store for a $99 developer fee, or you can use Stripe to implement payment right into your web app with almost no hassle.  Never before has it been so easy to sell your products world-wide.  It didn’t use to be that way.

So, I ask you, again. What the hell are you waiting for?


See this moment for how precious it is.  The world has basically gotten together and made it so that anyone who wants to be an entrepreneur can.  There really is no excuse left.  If you are one of those people who say you want to start a company, do it.  Do it right now.  Make it happen.  Now is the perfect time.  There are no excuses left.


Faulty Excuse Number One:  “I don’t have a technical cofounder.” 

This is just bullshit.  And, hopefully, by now you know it.  Just get started.  Whatever you do, please don’t ask me to help you find one.  But, I can say with no uncertainty that it is possible to start your company right now, just you.  If you can make some progress on your own and validate your product, you will be able to find a technical founder in due time.


Faulty excuse Number Two:  “I don’t have any technical expertise.”

Yes, it may be true, you don’t.  But that doesn’t have to stop you.  You could teach yourself how to code using Code Academy, General Assembly or any other number of emerging platforms.  Sure, you might not be that good at first, but it doesn’t have to stop you from getting a startup off the ground.  And, if your idea is simply too complicated, here’s a very real startup lesson you can take hold of right now— Make it less complicated.


Faulty Excuse Number Three:  “I can’t quit my job.”

Well, it’s not that you can’t, it’s that you won’t.  And that’s okay, but it’s also never going to change.  Startups involve risk.  The fact that this is the least risky time ever can’t help you take that next step, you have to do that yourself.  Go all in.


Faulty Excuse Number Four:  “I don’t know how to raise money.”

That has fortunately been solved for you.  You can apply to a bajillion incubators that will teach you how and provide the intros and necessary hype for you to execute.  And, with Angelist as an emerging alternative, you can hustle your way some investor demand and raise your seed round without any preexisting connections.



A quick footnote since I just know I’m going to get hammered on this post.  No, you can’t build a successful company having just 10 weeks of hobby-like technical ability.  No, you can’t just assume Heroku will solve your scaling problems.  Growing a company is really, really hard for hundreds of reasons.  But relentlessly resourceful founders figure out ways to solve these problems when growth is actually occurring.  You’ll never get there if you don’t at least start.


Discuss on Hacker News

Jason Freedman
tag:humbledmba.com,2013:Post/597994 2013-08-30T05:28:43Z 2015-09-16T20:42:34Z You can't teach passion

I just had a really frustrating meeting with a friend that just moved to the Bay Area.  He had the ever-so common request of wanting help finding a great job, working with awesome people in disruptive technologies blah, blah, blah…

This guy knew the right things to say, was clearly very smart and was networking in an honest attempt to find a great fit.  I was having a really hard time because I wanted to help him but I couldn’t get around my gut feeling that he just sounded uninteresting.

He was doing that thing that lots of people do where they talk abstractly about what it is they want.  So he was saying things like, “I really want to get into digital media and specifically data-based analytics.”

And all I’m thinking is what the hell does that mean?  I mean, literally, what the hell is he talking about?  And the funniest part is he used the word “specifically” as if one abstraction layered on top of another abstraction was a route to being more understandable. I’m thinking about what it would be like if I introduced him to someone at another startup.  Would they really want to hire a guy that talks like this?  And the answer is clearly no.  I mean, maybe he would work really well at a large company where it seems like this sort of businessy speak is more welcome, but I know startups don’t like it.

And finally in the midst of going back and forth where he was trying to describe what it is he actually wanted to do and I was continuing to struggle to understand him, I finally said, “Dude, you just don’t sound passionate about anything and no one around here likes to hire people that aren’t passionate.”


And that hit him like a ton of bricks.


Was he interested in digital media? Yeah, probably.  Was he interested in data?  Yeah, probably.  Was he passionate about it? That’s probably a stretch.  And at large companies, it’s probably okay to be really interested in something, really good at it and receive a paycheck.  But startups don’t work that way.




My company, 42Floors, is trying to solve the way people search forcommercial real estate.  My cofounders and I have risked everything to do this.  Two years ago we had no money, massive credit card debt, no one believed in us, and yet we kept building because we knew this was possible. And now we have a site that looks good, we have investors, we have users, we’re growing.  We need people on our team who could push us forward.  We’re looking for people that are just as passionate as we are.

And I think that’s what every founder wants.  Every founder I know has taken unbelievable risks and made incredible sacrifices in order to get their startup off the ground; and they want people that are just as passionate as they are.




And so my friend, though incredibly intelligent and well educated, simply wasn’t passionate enough to even get to the first interview.  So our conversation kind of ended in a weird way because he was sitting there knowing that my observation had struck true and not knowing what to do about it, and I similarly felt bad because I felt like I was leaving him hanging without a rope.

But I’ve now had some time to reflect upon it and I’m going to go back to him with a few pieces of advice because the reality is, I still think it’s true that you can’t teach passion but you can certainly help them search for it.


So here you go, 6 tips for finding your passion:


Hang out with passionate people

Passion is by its very nature contagious and when you’re with passionate, you get inspired.  You start to see what it’s like to truly be engaged in something.  In a way, this is what accelerators like YCombinator provide.  It’s a community of unbelievably passionate people and it is unbelievably motivating to be around them.


Stop generalizing

It’s really, really hard to be passionate about something in the abstract.  Passionate people are always obsessed with details.  At 42Floors, we’re crazy obsessed with the angle at which we take photos of an office.  If you shoot an office from the corner, slightly high, using a wide-angle lens, the picture just comes to life.  We love people who care about details.


Be a maker

It’s really hard to be truly passionate about something when all you’re doing is critically analyzing it.  All of my friends that went into consulting – virtually all of them – have complained about how, in the end, they were frustrated that their end product was a PowerPoint deck.  Several of them have now gone into entrepreneurship and they have been amazed themselves about how passionate they are about building something real.  Making stuff is liberating.  It taps at your creative potential.


Experiment with different niches

One of the common things I hear whenever I encourage someone to take a really deep dive into one thing specifically is that they don’t want to close off their options. But doing a deep dive into one specific job track doesn’t preclude you from also doing deep dives into other areas.  Think of your job search as an in-depth survey course in startups where each week you spend time diving really deep into one type of startup so that you emerge from that week passionate or not passionate.


Be patient with your time

It’s really hard to find something deeply engaging so you have to give yourself the opportunity to search for it.  If all you are looking for is a job as quickly as possible you’ll be less likely to find it. And probably less likely to find a job that’s right for you anyway.


Be willing to learn

What I found with my friend is that he had learned a particular set of skills at business school and needed a place to apply those specific skills.  As if the learning process had ended.  But every super passionate person I know is constantly learning, so if you want to find your passion you should assume that it will involve learning new things.




And finally, don’t settle.  Just flat out don’t settle.  And that’s kind of, in the end, what it felt like this guy was doing.  He was just looking for a job and was kind of willing to settle for anything that wasn’t miserable.   In the end, if he had a startup that paid him a salary, was located in the Bay Area, and had reasonable people around him he was going to be content.

Aspire for much more. In fact, demand much more.  It’s okay if you’re not feeling the passion right now.  Just go out and find it.

Jason Freedman
tag:humbledmba.com,2013:Post/597636 2013-08-28T16:29:47Z 2015-09-15T20:58:24Z Cargo Cults

So let me tell you a little story about Papua New Guinea.  Located in the southwest Pacific, Papua New Guinea had been, for most of its existence, isolated from the rest of the world.  That is until its location played a role in WWII.  From the perspective of a native inhabitant of Papua New Guinea, it must have been fairly shocking to see massive metal birds flying across the sky.  No less interesting were the giant metal whales that floated in the sea.  And you can imagine how confusing it must have been the first time one of these giant metal birds or one of these giant metal whales broke apart and came crashing down onto their island.

And if that weren’t crazy enough, their bellies always seemed to include wondrous riches, themselves almost unfathomable.  Wooden cubes filled with food and drink and all sorts of rare treasures.  And without too much of a stretch of an imagination, you can envision natives of Papua New Guinea beginning to think that these gifts that came out of the bellies of these metal birds and metal whales were actually gifts directly from the gods.  What else could explain such craziness?  And then these metal birds started landing and out of their bellies came people.

They looked different though and they spoke their own ancient language and wore their own ancient robes.  And these creatures prayed to their own gods in their unique ways.  They built these temples specifically designed to attract more of these wondrous metal birds with such riches inside their bellies.  These temples were long, flat rectangles that they arranged on the ground like an oversized nest for the metal birds.  And to get the metal birds to come out of the heavens, the aliens would wave bright orange ritualistic objects in long rehearsed dance.

And the long rectangular temples and the orange baton ceremonial dance worked!  For in fact, they did bring forth more of these metal birds from the sky.  And for years, there were riches coming from their bellies.

But then one day, for no reason at all, the aliens left.  The metal birds no longer came.  The metal whales no longer sailed in the seas.  And there were no more riches.

Clearly, the aliens had not prayed enough.  Had not built enough temples.  So the natives took up the cause and built their own rectangular temples.  They performed their own ceremonial orange baton dance, just as the aliens had done.  And for decades, hearing stories of great riches, the Cargo Cults on the island of Papua New Guinea continue to pray to the gods of the metal birds, awaiting their inevitable return.




I think about Cargo Cults whenever I hear founders spouting buzzwords.

Is it really so strange to believe that the words mobilecloud,crowdsource could be part of an elaborate ceremony.  As if saying the works will bring forth millions of dollars from our venture capital enriched heavens? Is it really that crazy to believe that uttering the words agile or lean or customer development would produce holy engineering teams blessed by the startup gods?

And if you were to see someone praying to these gods, using their ceremonial words, so devout in their religious devotion, do you really think you could convince them otherwise?  After they had seen such proof to the contrary, do you think you could convince them that merely uttering these words is not enough – that the ceremony doesn’t actually matter at all?



Discuss on Hacker News

Jason Freedman
tag:humbledmba.com,2013:Post/597308 2013-08-26T21:49:18Z 2015-09-15T20:59:03Z The one HR benefit every startup should add

I just did a review of all of our benefits programs. Like other startups, 42Floors offers a great health, vision and dental package  and life insurance coverage.  We pay 100% for both employees and dependants. It’s expensive, but it’s worth it.

Having recently gotten married, I’ve been spending a bunch of time thinking about these sorts of things in my personal life as well.  And one of the things my dad brought up with me is just how important it is to have a good long term disability insurance plan in place.  I had never actually heard about it.  Long term disability is a policy that can pay out 60% of your salary for the rest of your life if you have an occupation-ending injury.

If something should happen to me and I can no longer do my job, a long term disability program could fundamentally preserve the standard of living in my family.  But they’re not cheap.  The premiums I was looking at for a middle of the road plan were around $2,500-$3,000 a year.  That’s a lot of cash to pay year after year.




Back to startups.

Our company benefits provider explained that individual long term disability insurance is much more expensive than a group policy.  To get all of 42Floors covered on a long term disability policy from a reputable firm will cost about $2,500 a year.  That’s incredible.  It’s almost identical to buy a group policy that covers everyone as it is to buy an individual policy that would only cover just me.

But there is so much more than just cost savings. I asked everyone in our company if they had long term disability policies in place.  Big surprise—no one did.  It’s just not something most of us think about.

I’m sitting here envisioning in my head what I would do if one of our employees was no longer able to do their job – what a horrible ethical position to be in.

For a fairly nominal sum, you could cover them with a policy that could make an enormous difference in their entire life.  And if at that horrible moment when you’re hearing the devastating news that one of your employees has been severely injured, you’ll at least know that because you took the time to set up this policy, they are going to receive a majority of their current paycheck for (nearly) the rest of their life.




Sometimes we get caught up with thinking of our various compensation packages and benefits as recruiting tools.  This one won’t really register as a recruiting tool. But, as the founder of a startup you should take the well-being of your employees as your single most important responsibility.  Spend five minutes today.  Do it right now.  Call your broker and get a good long term disability insurance policy in place.  And hope you never have to use it.

Jason Freedman
tag:humbledmba.com,2013:Post/584045 2013-06-14T03:05:23Z 2015-09-15T20:59:14Z 3rd Annual NFTE Launch: Mentor Aspiring Teen Entrepreneurs in SF

For the 3rd year in a row, I'm running NFTE Launch later this month.  NFTE is the Network for Teaching Entrepreneurship.  It connects mentors with aspiring teen entrepreneurs from underserved high schools in the Bay Area

We'll have 15-20 teens that all have ideas and want to build something.  You donate your time for one 3 hour spot.  Show up and you'll find yourself immediatley helpful.  No preparation needed, no follow up required.  It's one of the best ways to give back to the community doing what you love: helping people make something people want.

In the past we've helped set up Weebly sites, fill out Etsy profiles, and start Shopify stores.  This program is less about finding the next big innovation and more about making a connection with a kid.  

This year's program runs June 24-28th and is hosted by Rackspace on Folsom St.

Sign up here for one 3 hour mentorship session.

The week's mentorship session culminate with a Demo Day: Thursday 6/27, 5-7pm at Rackspace.  Everyone is welcome to attend.  More details here.

I would love to once again have lots of startup people there.  Please also forward this to others in your company and to others in the startup community.  Anyone versed in startups and interested in helping kids is welcome to sign up.

Here's an easy snippet to tweet:

In SF and want to mentor aspiring teen entrepreneurs?  Volunteer for 3 hours and make an impact.  6/24-6/28 http://bit.ly/1bCtUgJ
Jason Freedman
tag:humbledmba.com,2013:Post/577504 2013-05-06T03:28:17Z 2015-09-15T20:59:28Z YC without being in YC

Back in 2010, my startup FlightCaster had hit some serious obstacles and we needed to pivot.  We had set a deadline for ourselves for some metrics and we failed to meet them.  It was a bruising time.  We had to let half the team go.  I had to tell my investors what had gone wrong.  They asked that we consider just giving back the remainder of their money.  It sucked.

We had set this deadline early enough that we still had some money in the bank and still had plenty of enthusiasm.  What seemed insurmountable was starting over with a new idea.  To get us through this tough time, we played a little trick on ourselves.  We pretended that we had just gotten into Y Combinator again.  We had about the same amount of money left as YC+Start Fund.  Our runway was similar.  Why not just pretend we were in the program.  When you’re in YC, going from zero product to a launched product in 10 weeks is the name of the game.  When you’re not in YC, building something that fast feels overwhelming.

For the next 10 weeks, we tried to mimic each step.  We wrote up our various ideas as if they were YC applications.  I re-read a bunch of Paul Graham essays and got myself back in the mindset.  Once we landed on an idea (it was an enterprise travel product), we gave ourselves 4 weeks to get to Prototype day, just like YC.  We demoed weekly–to each other, other entrepreneurs, and our investors.  It wasn’t as good as Tuesday night dinners, but it worked–our productivity shot up as we wanted to make significant progress each week.  After that, the pressure was on to launch something.  We held off working on a business deck stuff until our Demo Day approached.

I was amazed how simply adding some YC-like structure to those several months made everything we were doing feel better.  Before that, we had been pretty lost.   But once we pretended to be in YC, we were motivated because we had a schedule to hit.

Effectively, our Demo Day turned out to be presentations of the new product to large travel agencies.  And they were interested.  Which then brought new term sheets from our investors.  Which also brought interest from a larger company, who wanted to have acquisition talks.  Eventually, we took the acquisition.




I’m hearing from fellow entrepreneurs right now that didn’t get into Y Combinator.  The very  best of them have already moved forward and are working on their startup at full speed.  Love that.  YC is helpful but certainly not required.

While there are definitely a lot of advantages to being in the YC program, the fact is you don’t need them to succeed.  You can get a huge chunk of the value of YC without actually being in the program.  That what this post is about.    Go out and grab it.


 What you can get from YC without being in YC


Advice from Paul Graham and the YC partners

Fortunately, Paul Graham writes down most of advice right in hisessays.  There is no set of  YC secrets that he hides from the rest of the startup world.  In fact, much of what he says in person simply reinforces the advice that he has already doled out through his essays.  Having watched him for several years now, I also find that if he starts to give out new advice within a YC batch, you will soon find that idea better articulated in an essay a couple of months later.  The same goes for many of the other YC partners who give their advice out for free in their blogs.


Advice from speakers

Every Tuesday night in YC, famous founders give advice to the group. Fortunately, a substantially similar experience is available to you every year.  YC runs startup school each year in October.  Many of the speakers that come to YC on Tuesday night dinners also present at startup school.  And if you miss it, their videos are posted up in the startup school archives.  When I did my first startup (which we did not do YC for) I sat down and watched two years worth of startup school videos as part of my preparation.


A set launch date

One of the most overlooked values YC provides is the date of demo day itself.  When you get into YC, the date at which you will have to show your product and traction to investors has already been set.  When you have a demo day approaching and you desperately want to show 4 or 5 weeks of traction, the pressure is really on to launch quickly.  And launching quickly is one of the single best pieces of advice you can get out of YC.  So, if you’re not in YC, simply continue to accept the date of demo day and force yourself to launch before then.


Feedback from other founders

One of the most intimidating parts of being in YC is that we demo our progress to each other every Tuesday night.  There is nothing formal about it; you’re just around a lot of people who are working non-stop and everyone is interested in what each other’s building.  And when you demo that often you inherently want to show progress so that you’re not showing the same thing two weeks in a row.  Just like taking a class in college provides some social motivation and structure, YC provides a really nice social cadence.  Find a community of startups in your city, and start demo’ing each week.  Make weekly feedback a heartbeat that powers your startup.


The cash

I don’t want to be dismissive of the $15,000 you get from YC.  For three of my startups, I was dead broke (and significantly negative) during the building phase of the company.  But I can still look back and honestly say that $15,000 was not a make or break number.  There are other ways to make it work.  Now of course, YC also gets you start fund now, and it is certainly nice to have $80,000.  However, it’s rarely a number that fundamentally makes the difference.


The mantras

YC has a bunch of mantras.  For the most part, they are simply concise versions of advice that has n0w been given hundreds of times.  Ignore them at your own peril.

“Make Something People Want”

“Write Code, Talk to Users”

“Be a cockroach, impossible to kill”

“Do stuff that doesn’t scale”

“Launch early”


Demo Day

No doubt, demo day is an incredible opportunity for a startup.  The amazing thing though is just how far each of the startups have gotten in such a short time.  Most of the startups have traction graphs that go steeply up and to the right.  If you make the same progress in your own startup, you won’t need a demo day to raise money.  With extra networking and AngeList effort, you’ll do just fine raising money.  No traction?  Well then, demo day wouldn’t have helped you anyways.


The Network

The network of YC alumni is quite awesome.  Everyone’s willing to help each other out.  It’s the second most helpful community I’ve ever been a part of.  The first?  Hacker News.  Ask for feedback and you’ll get it.  Ask for help and you’ll get it.  Give back to the Hacker News community whenever you can.  Treat it as your community, full of people conspiring to help you with your startups.  The comments can often be overly critical.  Don’t let that distract you from the immense value this community overall still provides you.  Use it.



Go to it everyone!    And if we here at 42Floors can help you in any way at all—please let us know.




Discussion on Hacker News

Jason Freedman
tag:humbledmba.com,2013:Post/498267 2013-04-26T16:39:16Z 2015-09-15T20:59:46Z Is this what it’s supposed to feel like?

I couldn’t sleep last night because I’m concerned about how we’re going to get more high quality photos up onto 42Floors.  We’re a site that makes it easy to search for commercial real estate.  But it’s not a good search experience unless you have great photos.

We have increased the number of listings on our site.  Awesome!  But so much so that the performance on our site slowed to a crawl.   We had tried to avoid premature optimization.  But now we have too many new listings to load at once.  No caching.  No intelligent API calls.  Big surprise that our site is painfully slow.

I just got an email from an engineering prospect who has decided to turn down our offer.  We put so much time and effort and passion into recruiting him.  He decided he wants to go off and start his own company right now.  I can’t hold that against him.  But we’ve got like a gazillion open positions, and I need to get them filled.  My team is depending on me.  I hate letting them down.

We’ve been doing tons of user testing in the last few weeks.  People complain that it’s difficult to go back and forth between our map view and our listings view.  I can’t blame them. I’ve wanted to fix that for months, along with 100 other things I’ve wanted to do.  But to see users, right in front of me, trying to use our product and getting visibly frustrated – Ughh! It’s like they’re calling my baby ugly, and I have no other choice but to agree.

We just had an investor ask why we still don’t have email alerts setup for new spaces that come online.  It’s the most simple of features.  We should’ve done it nine months ago, and we still haven’t gotten around to it.  Oy! Should I just say what I said nine months ago?  “Yep, it’s in our pipeline.  We’re about to get to it.”

I’m not even going to go into all the challenges with traction, user acquisition, business model… nor will I mention the team issues, the tough conversations with investors, and everything else.

I keep reading on Techcrunch of these startups that are crushing it.  Do they also feel this way?




Startups are just plain hard.

All too often we startups market ourselves on Hacker News as fairy tales.  But this is no Potemkin village.    Startups are hard. They are always hard.  Every step of the way.  I’ve never met a single successful founder who has said otherwise.




We are hiring right now at 42Floors – we have a ton of job openings.  I wish I could say that everything is perfect here.   But if you join our team, we’ll be open with each other.  We’ll face every challenge head on.

And maybe someday we’ll look back on all the struggles and tough times and realize we were crushing it.

Comments on Hacker News

Jason Freedman
tag:humbledmba.com,2013:Post/483579 2013-04-24T15:24:22Z 2015-09-15T21:00:10Z My strange aversion to vacations

Vacations have always been hard for me.  It’s a weird thing to say, but it’s true.  They just don’t come naturally to me.

I remember when I was in business school, all of my classmates were taking these epic vacations seemingly all the time.  Spring breaks in Costa Rica, pre-internship trips to South America… I saw the pictures and they did look like fun, but yet each time I stayed home to work on my startup.

This was back in 2007 when I was running OpenVote, which was a web 2.0 Facebook app company.   That went nowhere.  After two years of making no money for the company, spending all of my investor’s money, and wasting away what little cash I personally had, those pictures of everyone else’s vacations were painful to look at.

But when we finally turned the servers off for OpenVote, I didn’t make up for lost time and go on some sweet vacation. Hell, I didn’t even relax for a few days.  I was so in debt and so frustrated with failure that I got right to work filling as many hours of the day as I could with random consulting jobs.

And, wouldn’t you know, less than three weeks later, we had stumbled upon Flightcaster and off I was starting another startup.  The time for vacations had passed once again.



I always thought my issue with vacations was just some internal restlessness. That is until I started 42Floors and my good friend Dana told me his version of the exact same story.  There is something about vacations and startups that just don’t work well together.

Forgive me for generalizing…but at a big company, you are trading your time and passion for compensation.  Vacation is time off. It’s paying for 11 scoops and getting the 12th for free.

But startups are different.  Startups are a mission; a belief that something impossible is actually possible.  It’s being part of a team that is working toward some distant horizon.  It’s this competing against the impossible that makes it so much fun.  Your coworkers are your friends.  It’s so much closer to a life style than a job that taking a vacation from your startup doesn’t have the same connotation.

But that doesn’t mean startup people don’t need vacations – we clearly do.  If for no other reason than our best ideas come when we’ve been able to disengage from the problem in front of us.  Vacations are a change of scenery.  They’re a chance for perspective.  They’re quality time with our friends, family and significant others.  They’re a chance to see the world, to waste away the day reading books, playing chess, trying new things.  Vacations are 100% essential.



At 42floors, we created an unlimited paid time-off policy.  Everyone takes as much as they want whenever they want.  Because we’re smart, motivated, responsible people, we don’t have to worry about this policy being abused.


But here’s the kicker:  unlimited time-off doesn’t work.


While the unlimited paid time-off policy works for some of the people some of the time; it still feels too hard to get away.  It’s not the social pressure part. We’ve worked really hard to promote vacation-taking in the company.  It just comes back to the fundamental issue that vacations for startup people are hard.

So we have been searching for ways within the company to address it, and we’ve come up with a really good one that I thought I’d share.


Everyone Needs a Pre’cation


At 42floors, we heavily, heavily recommend that all new people take two weeks of vacation starting exactly on their first official day.  What this means is that when you get a job offer from us, you’ll pick a start date.  And that’s the day we start your payroll.  And that’s the day you leave for vacation.

And you get to take that time to transition from one chapter of your life to the next.  If your startup just failed or you hated your last job, you get a couple weeks of mental and physical recovery.  If you have a significant other that’s been dying to get away with you, you can go away someplace nice knowing that your first paycheck will be waiting for you when you return.

You’re mentally free to completely let go.  Vacations when you’re searching for a job don’t work great because you feel the pressure to find a new job.  Vacations in the middle of a job are tough because you have the urge to check in.  But vacations between jobs with a signed offer letter in your hand, those are the absolute best.  The only thing that holds people back from taking advantage of this perfect time is that it feels akward to ask.

And so that is why we had to make precation a policy in our company (we would make it actually mandatory, but we have this thing against telling people what to do in our company). Thus far there has been 100% adoption.




Precation doesn’t solve everything, but it’s at least a way to start off on the right foot.  If you’re a founder of your own company, think seriously about implementing this.  You won’t regret it. If you’re an employee in a company, chat about this on Hacker News and, hopefully, enough founders will see it that it could become a thing in the startup world just like free lunch and no start times.  And if you’re looking around for a new gig, well then obviously come check us out at 42floors.  We’ve got like a gazillion roles open and we’d love your help.

Jason Freedman