Why We Invested In Mosaic

Mosaic is a tech enabled home builder that partners with top-tier home developers and runs their operations, literally building the homes from foundation to move-in ready. 

But my first conversation with Sep and Salman, co-founders of Mosaic, had nothing to do with home building whatsoever. The subject didn't even come up. We talked exclusively about how teams work together, different styles, different formats of collaboration, autonomy, authority. For Sep and Salman, how people work together and, importantly, how they work with technology is the subject that originally brought the two of them together at Stanford, where they studied human computer interaction.

It's amazing that the two of them found residential home building as the medium upon which to write their novel. Human-technology interaction in home building is virtually non-existent. The world builds homes today almost exactly the same as they did 20 years ago. And that's not a way of saying the industry is filled with Luddites. In fact, it's saying the opposite. The industry is filled with hard-working people who learned their craft through the process of apprenticeship. Plumbers care about plumbing, electricians care about electrical circuits, framers care about framing.  Salman describes it through this quote:


“There is one timeless way of building. It is a thousand years old, and the same today as it has ever been.  The great traditional buildings of the past, the villages and tents and temples in which man feels at home, have always been made by people who were very close to the center of this way.”

 - Christopher Alexander, The Timeless Way of Building (1979)


If building a home didn't involve a craftsperson, it would be easy. But the reality is, even with perfect specs, each home is a little different. The environment is a little different. The people who worked on it are a little different. And these differences matter. When a framer needs to change the positioning of a two by four by a few inches, that will change the positioning of an electrical outlet, which will alter where a pipe goes, which the drywall will have to be custom fit to.

These change orders add up, each one potentially creating errors in the process, each one driving up the cost of real estate. And residential home building is one of the few industries in the world that has never seen increasing efficiencies over time either to technological advances or economies of scale. Each home still takes a certain number of people working a certain number of hours and certain number of materials to succeed.

Most innovation in the sector has until recently been in moving construction offsite and standardizing it.  But that doesn’t serve the other 99.99% of homes that are still customized to the buyer and built on site.  No one has figured out a way to change that equation until Sep and Salman started Mosaic, and the magic of why Mosaic works is they care just as much about why people work together as the homes that get built.

I saw the magic when I visited their site in Prescott, Arizona. In Prescott, Mosaic has hundreds of homes already built, hundreds more in development, and thousands in the pipeline.  Each home has a digital twin. All of their specs, cut sheets, change orders, plans digitized. The process is managed through the workflow apps that they've created. They measure things like percentage of days where 100% of materials are available on site so that the craftspeople can start work immediately. They excessively track number of warranty tickets. They track speed, quality, throughput, and efficiency.

And although those all those metrics are the numbers that exist on their dashboards, it's not what they want to talk about.  For Sep and Salman, the winner of the home building game is the company that treats the tradespeople the best. Full stop.

Whoever convinces the best electricians and plumbers and framers to switch over to their shop is the one that will win. The best people will build the best homes the fastest. Even with all their technology, it's all about the people, and thus their technology stack is beautifully written to help these craftspeople do their best work.

And anytime you talk to a true craftsperson in any industry, they want a few simple things. They want to be paid fairly and timely, for sure, but they want to be respected, valued, and empowered to do their best work.

And as I walked the sites talking to random construction crews, this was the subject that came up.  They enjoyed working for Mosaic because they felt like their time is valued, their opinions respected, their compensation fair and fast, and most importantly, they were proud of the homes they were building.

When I talk to the home building partners that have entrusted Mosaic to take over their entire operations, this was the subject they kept returning to, "Mosaic treats my people well and so we trust them."

In just a few short years, mark my words, people will be writing analyses of the growth, market size, margins, defensibility of the Mosaic business model, and for us, at Peak State, all those numbers pencil out. It's a huge business. But our thesis today in leading their Series B is that Sep and Salman and their team have figured out how to help the best people work together to build homes that people love.

Or as Salman more eloquently puts it:


"Our mission is to make places people love and make them widely available."


We are holding true to the timeless way of building and evolving it through technology.  In a thousand years when people look back to the great traditional buildings of this millennium, we want them to be beautiful and resilient. We recognize it is an ambitious vision, but we are inspired by and committed to delivering on it every day..

Go Mosaic! We're excited to be on this journey together!

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.

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.

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.

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.

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.



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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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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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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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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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