How to Fake Courage
Define your goal early and stay true to it
Early on, my cofounders and I agreed we would not stop short of fixing commercial real estate search world wide. We would be singularly focused on building a big, successful company—even if that meant increasing our overall odds of failure. That may sound trite, but I can tell you it has already impacted dozens of decisions. My mindset during FlightCaster was to simply not fail. Every time I could have rolled the dice, I took the risk-minimizing option.
At 42Floors, we’re okay with the prospect of failure. We’ll roll the dice every time to keep our full dream intact. Investors/employees/customers can smell the difference. We’ve said this from the beginning. And in the beginning it’s really easy to say because you have nothing to lose anyway. Now that our company is off the ground, we’ve simply gotten used to saying it.
Set a really big goal, go after it and ignore everything else.
Avoid isolation
What was so miserable about being on that tennis court as a 15 year old was that it was just me out there alone.
I’ve struggled at everything I have ever done. It took me years to see this, but I finally see that every other entrepreneur has had the same problems I’ve had. I did a YC a second time mostly because I wanted that community of peers again. As I’ve mentioned before, if you can’t get into a YC, make your own.
Believe that you can change
Paul Graham once said the hardest part about being an early stage investor is thatfounders can change. I was nervous when I applied to YC with 42Floors because I was afraid of repeating the same mistakes again. But fuck that! Those types of thoughts are worthless. Focus on the opportunity you have right now and become the person that can get it done.
I am vastly different founder in this company than ever before. I refuse to let my old weaknesses haunt me further.
Get a win under your belt
I have to include the acknowledgement here that this post is total bullshit. I didn’t gain this mindset until we had already sold FlightCaster. That win gave me a ton of confidence to swing bigger this time.
Don’t ever say you’re crushing it
Every time I hear an early stage entrepreneur talk about crushing it, I know they are fighting demons within themselves. There’s nothing worse than pretending to the world that you’re doing better than you actually are. All it does is isolate you even further. One of the most powerful parts of my blogging in the last few years is I’ve been able to share openly how hard things have been. It’s taken an immense stress off of me personally.
So, to all you founders out there thinking that other everyone else possess some genetic gift of unending courage that you lack. It’s not true. They’ve just faked it better. So can you.
– Jason Freedman
Wandering Wandering Star 