humble pie.

Thank you to everyone who has been supportive of me with this blog since I started it last year.  Many of you have voiced your appreciation for posts that you've found helpful.  It's been a really fun experience and a nice way to pay it forward as so many people have mentored me on my own path.  The fact that FlightCaster got acquired halfway through my first year of blogging just made the whole thing easier.  The acquisition gave me a credibility bump and empowered me with confidence.  I generally find that my best posts (based on my feelings for them, not just reader counts) have a nice balance of me as a person and suggestions for other entrepreneurs.  I have tremendous pride in what I do and I love doing it.


But I feel like a sham.


I'd like for this blog to be more honest, so I have a few things to share with you.  I'm not nearly as proud of my actions at FlightCaster as I make myself out to be.  To be 100% clear, I'm incredibly proud of my team, my cofounders, and all the awesomeness that we created together.  Working with my best friend to create our dream was a pure honor and I'm fortunate to have been a part of it.

But I'm not proud of how I did it, and I feel like I get more credit for our outcome than I deserve.  Part of the reason for that credit is that I actively promote it myself.  But inside, I know that I mostly just got lucky.  And I got lucky in spite of myself. 

I'm sorry.  This isn't coming out very well.  Let me try to be more clear.


From day one, I feared failure and it affected every decision I made.


There, that's mostly what I wanted to say.  I was not really a courageous founder; I mostly wanted to not fail.  My first company failed and I ran out of money (both my company and me personally).  When we started FlightCaster, I felt that I was lucky to get another opportunity at startup life.  For the first few months, we worked our asses off and it was awesome.  But soon, I started feeling stressed about the possibility of failure.  With one failure under my belt, I felt that another failure would put an end to my startup dreams.  By this time, we'd gotten into Y Combinator, one of the greatest startup handicaps ever created. If I couldn't succeed with YC's help, than I was truly incapable.

My fear of failure caused me to make several stupid decisions.  First, I built our team up too big, too quickly.  Then, because I was so nervous about not having enough momentum, we built out our product faster than our customer development process dictated.  Before launch, we'd created our flight delay prediction back-end with a working website, iPhone app, and Blackberry app.  That's insane!  Three front-ends before launch!  Each with 1-2 people building it.  And I know why I did all that.  I was so fucking scared of failing to raise money post-Demo Day, that I felt like I needed to show we were further along than we really were.

I'm incredibly proud of the investor crew we put together.  But the truth is that, again, my fear drove my decision-making during the raise.  We took on too much money, too early.  Pretty much against everyone's advice, including that of our investors.  And it was my call.  If I'd had more confidence, we could have gone 6-12 months longer with a smaller team and on less money.  We could have validated our product and built our company before giving up too much equity.  But I equated 'not raising enough money' with 'failure.'  I look at some of our batch-mates who waited a year after YC to raise money and they now have the foundations of really sustainable businesses.  I'm so proud of them.

Even our acquisition was driven by fear.  We had another round of funding on the table, but I so wanted to call FlightCaster a win and didn't want to risk walking away with nothing.  Yeah, we were stoked about the company that was acquiring us, and it looked like a good opportunity for us, for our employees, and for our investors.  But I love working for myself. Was this what I really set out to do—to sell my company only two years after starting it?

The truth, again, is yes.  Everything I did with Flightcaster, I did consciously or unconsciously with an eye towards selling the company quickly, getting out, and getting my win. 

Am I glad we sold?  Absolutely.  At the time, it was the best possible conclusion to a series of decisions that had led us there. But it's time for me to be more honest with all of you and to tell you that I'm going to do a better job next time.  I'm not going to let my fear of failure drive my decisions next time around.  If we fail, we fail.  A startup failure won't affect how my family sees me, how my friends see me, or how my girlfriend sees me.  And I'm never again going to let the possibility of failure affect how I see myself.




So, with all of that now said, I want to tell you that I'm starting a new company.  It's called 42Floors.  We're going to fix commercial real estate.  For some reason, commercial real estate never adopted the internet.  That will soon change.  I'll have a lot more to say about the company in future posts but for now, just know that I'm giving it my all this time.  I want to build a company that I can someday tell my children about.  I have visited my grandfather's company, and I know what courage it took him to build it.  I have dreams that my grandchildren will someday walk the halls of a company I created, and they'll be proud of the impact I made on the world.

I also plan to hold on to the truly honest posts like this one so that my children and grandchildren can know that I got scared too. The fact is, I'm still scared that I'm going to fail.  I can't completely get rid of the feeling.  I am simply choosing to no longer be bound by that fear.  We may make it, we may not.  But I'm determined to be more open and more courageous in the process. 

I would love it if you'd help keep me honest.  While I appreciate your support, I most appreciate the skeptics out there who push me to do better. From here out, please consider your 'unsolicited' advice...very much solicited and appreciated.

I thank you in advance.

Please come check us out.

Sign-up to learn more at,

and like us on Facebook.

and follow us on Angel List,

and follow us on Twitter.



Sign-up now to among the first to participate when we launch.  It's cool shit.  Don't miss out.

I would also greatly appreciate introductions to potential advisors.  We're not fundraising until the spring, but I'm happy to 'get coffee' with people who are interested in getting to know us.


Find discussion of this post on Hacker News.


I'm Jason Freedman.  
I've got a sweet-ass new company: 42Floors.  Find it on Angel List.
Previously, I did FlightCaster.
I welcome connections on Linkedin,  Facebook, and Twitter.
10 responses
Thanks for this. 'Twas something I truly needed to hear today and it leaves me feeling a slight bit more normal.
Such a great message! Appreciate the candor, but you've got nothing to apologize for.
What refreshing honesty.

I can't wait to see what the new startup is about...Commercial RE is a huge opportunity area, lots of potential.

Excellent post. I truly respect the courage you displayed in admitting that fear, rather than the sense of changing the world, influenced your decision making.

Best of luck for 42floors. I am sure you are going to do well - people really like working with someone who is driven and incredibly candor/honest in his conduct.

Very few people are like you. You make the world a better place to live in. I hope you sustain this quality.

I don't know... Seems to me you needed a win, so you did everything you could to maximize the probability of that, which was appropriate given the definition of success as a win. Fear can be a powerful motivating force.
Your honesty is refreshing... thanks for talking about the process of creating and selling FlightCaster. I'd say fear is pretty much part of any risk... small or large. So give yourself a break moving forward with 42floors. There will be times of fear which will undoubtedly motivate you. Love what you're doing and find some level of "I'd do this anyway... even if I failed!" Your process is great to read for others. Think of the folks you're mentoring!
Great post Jason, very proud of you for being so honest!
Great post Jason!

That's why I always come back to your blog, the unvarnished truth with a good dose of humility.

I think the important thing in life (and creating a start-up becomes a huge part of your life) is making the best decisions you can at the time, recognizing mistakes when they happen (and they will happen, again and again) and learning something from every mistake you made. That's something you can't do without being humble.

Keep up the good work!


All credit to you for 'opening up'. I've been involved in a few startups and I've been surprised at how 'truth' and 'honesty' gets trashed. How can we learn if we don't face up to the facts of our experiences? You'll be all the better for your efforts to value honesty and truth.
Wow, this must have been a tough post to write. Partly because finding the right words is always tough, but mostly because it takes being honest with yourself first.

I always appreciate your blog and this kind of self-awareness is the reason I keep coming back. Thanks.