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.

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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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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.

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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.

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?


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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.



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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.

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.

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.

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.