Obliterate Startup Depression

One of my favorite parts of the startup community is that we generally all acknowledge that we're not playing a zero sum game.    We create value by creating new markets and disrupting old, inefficient markets.  Sure, we compete against each other as well, but in general, the communal spirit of entrepreneurship is a rising tide that lifts all boats.

We need to do an even better job of supporting each other though.  And more so than just with introductions, helpful blog posts, advisorships.  We need to support each other on a personal level.  We need to acknowledge that almost every entrepreneur goes through startup depression at some point.  And most of us go through startup depression quite regularly.  

I go through it all the time.  During FlightCaster, it hit me several times.  The worst of it was 12 months into the company.  As a team, we were struggling on lots of fronts.   Our business development was going slowly, our complex prediction system kept breaking, and our team was starting to argue.  We weren't getting enough users to our site.  Paul Graham warns all YC companies that this period will come.  He calls it the Trough of Sorrow:

Oh man, it was the worst.  I fought with my cofounders, who also happen to be some of my closest friends.  We had heated meetings with our investors, trying to explain why things were not going smoothly.  Not only could I not fix everything, many of the problems were my own fault.  I could feel my team starting to doubt my leadership.  I couldn't blame them, I was too.

On the inside, I didn't just feel bad or sad or stressed.  Worse, I felt empty.  Startup depression is like running an ultra marathon on no sleep.  It's the lack of energy that is so tough to overcome.  It sucks.  I didn't approach each day with creativity and endless passion.  It was just hard.  And it was so so tempting to give up.

And I would give up.  I remember those mornings  when I came into work late.  I would wake up at normal time and just not get out of bed.  Maybe I'd watch reruns of the Office or mindlessly browse Reddit.  I'd mope around my apartment wanting anything but to go to work.

This is startup depression.  It happens.  It happens to all of us.  We get it and deal with it in different ways, but we all get it.  There's no way to avoid it in this line of work.  Entrepreneurs choose this life and the rollercoasters are very real.

I have emerged from every one of my startup depressions just fine.  Sometimes, it lasts days and sometimes it lasts just a few hours.  I always come away stronger and I've learned a lot in the process.  I want to share a few of the things I've learned.  

How to Obliterate Startup Depression

Get help from your cofounder
Max Levchin of Paypal and Slide fame just spoke at Y Combinator's Startup School.  He talked fondly of the time Peter Thiel, his cofounder at Pay Pal, told him straight up that everything would be fine.  They were in the midst of a funding round going south and Max was losing faith.  With a few timely comments and rock solid confidence, Peter put Max on his shoulders that day.  That's what cofounders do.  I would never have made it through FlightCaster without my cofounders' support.  Cofounders need to support each other during the down times.  It's perhaps the single most important task your cofounder can do for you.

Get a startup advisor
In a previous post, I talked about the difference between a strategic advisor that helps you raise money by lending credibility and a startup advisor that helps you navigate all the small shit.  A startup advisor that is only 12-18 months in front of you on the path will know exactly how you feel.  He'll be able to tell you honestly whether everything will be alright.  Sometimes it will be, sometimes it won't.  But you need an outside perspective to help you see the difference. Want to know whether you have a great startup advisor?  If you haven't gone to them during your down moments, than you don't have one.  Get one.

Invest in your own health
The single greatest perk of the company that bought FlightCaster was the health program. They had a nutritionist on staff that bought all healthy foods and an on-site gym that had an incredible communal workout program.  Check out the video I made for them while there.  You may not be able to afford an on-site gym for your startup, but you can still invest in health. Create good habits when things are going well and stick to them when things go south.  Right now, I go climbing every Tuesday and Thursday morning with an old friend.  No meeting is ever scheduled during that time.  It's perhaps the most important standing commitment on my schedule.

Be open with your community
Too many of us fall victim to startup bravado.  We always portray our startups as unstoppable successes.  I hear it all the time when I talk to people.  The first 10 minutes of a conversation are about how great everything is going.  If I stick around long enough, we finally let our guards down and admit just how much we're struggling.  Communities like Hacker News and Y Combinator can be daunting because we witness such success from our peers.  It is intimidating.  However, if you're honest within a community like this, you will always be impressed by the response.  Check here, here, and here for great examples.

Be conservative in other parts of your life
With a startup, you tie up most of your net worth in a single, illiquid stock.  That stock is heavily correlated with the stability of your salary, your availability of healthcare, and your mental state.  For this reason, you should not have any risk in the rest of your finances.  I keep all my money in an FDIC-insured bank account.  Sure, I would like to make a better return, but I can't take the risk of compounding my losses if the markets tank.  Startup life is hard enough already, don't lose your money with optimistic investments.  Money troubles is an incredibly efficient way to trigger depression.

Create company rituals
You need some way to break free as a company when you hit the seemingly endless Trough of Sorrow.  One of our traditions at 42Floors is winning or losing each day.  Some days we lose.  We're open about it.  A few weeks ago, we got chewed up by a potential investor.  We were all down on it.  As we were moping around the office, I sent everyone home.  We lost that day.  Tomorrow is a new day.  And we celebrate the fuck out of the days we win.  During my first company, I never celebrated our first term sheet because I didn't want to count my chickens.  That was stupid.  A term sheet was a huge fucking accomplishment!  And by the time we signed definitive documents on that round, we were so chiseled that we felt beaten up.   At 42Floors, we celebrate every day that we win.  Right away.  Whether it be a term sheet, a code push, or a happy user — wins should be cherished.  You never know how long it will take to get another one.

Get your house in order
During FlightCaster, I moved apartments during our funding round.  Wow, that was horrible.  In the midst of gut-wrenching highs and lows, I also didn't have a stable place to live.  Fight the startup battle at full strength.  There's nothing better than going home to great roommates, caring friends, and a loving significant other.  I joined a communal ski house when I moved out to the Bay Area.  My favorite part about my ski house is that no one there cares about technology or startups.  We don't compare investors, we don't talk user traction.  It's awesome.

Talk openly about depression
Don't be afraid of the word.  Depression is not some word to be whispered under your breath or handled with kid gloves.  Getting depressed doesn't make a person weak.  It doesn't mean that someone will be unsuccessful.  We all have depression at some points.  We also all have jubilation at some points.  The high and lows come as a package.  You rarely get one without the other.  I talked extensively with an old colleague about the ways we each dealt with depression.  It's much easier to battle it when you're not hiding it.  And if you need professional help, go get it.   Whatever you do, don't bottle everything up inside.


Of course, you can't really obliterate startup depression.  But you need to have the mindset that  it's beatable.  You should treat it just like you would any user acquisition problem or business model challenge.  Create processes to solve it.  If you don't treat it as a tangible problem that needs solving, you'll be like a toy boat floundering in rough waters: helpless to control your own fate.  And with startups, rough waters are always on the horizon.

We're getting closer and closer to the launch of 42Floors.  I can't tell you how excited I am to share what we're doing with all of you.  I really think we have a chance at fixing commercial real estate. I'm also nervous.  I call the period we're in now Delusional Optimism.  All of our ideas look gorgeous in Photoshop.  No customers have left us.  We haven't run out of money.  We haven't faced bad press.  We haven't had users choose the back button over the sign-up button.  No depression, no problems.  Delusional Optimism is the best.  And it can't last. 

Shit's about to get real.  Things will get tough.   Bring it on.  We're ready.




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We're fixing commercial real estate.  Forever.

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I'm Jason Freedman.  
I've got a sweet-ass new company: 42Floors.  
Previously, I did FlightCaster.
I welcome connections on Linkedin,  FacebookAngel List and Twitter.