The #1 defining characteristic of entrepreneurs


They bounce back.


It's THE defining characteristic of being an entrepreneur.  Some

entrepreneurs are creative, some aren't. Some are tech-focused, some

aren't. Some are business savvy, some aren't.  But bouncing back.

Yeah, that's what makes an entrepreneur.


I'm working with some business school students right now on an

entrepreneurship project.  They're putting together a pitch deck as

part of their spring semester, and I'm advising them.  After 4 weeks

of work, they were still 'concepting' the investor deck and hadn't yet

produced a reasonable first draft.  I was growing concerned with their

progress.  They were doing typical MBA things that may have worked

well in, say, consulting, but were a poor match with entrepreneurship.

I was most concerned with their slow rate of adapting to the

entrepreneur's mindset.


Finally, after another week of too little progress, I emailed the group's

leader this message:


"I think it's wake-up call time for both you and the team.


I have significant concerns that this project will come to fruition

with any level of acceptable quality and depth, both in terms of

normal school standards and my standards, which are considerably

higher.  I'm not saying you won't get there, but as of yet, I've seen

no evidence that this team, as currently led, will make it.


I doubt there are many things in your life that you have done poorly.

I fully expect you to take a tough round of feedback in stride and

respond with gusto.  As always, I am on your side and available to be

helpful in any way that I can."


It was a pretty tough message to send and to receive (I assume, far

tougher to receive).  I do like being a nice guy, supporting people

with positive encouragement.  I come from a summer camp background and

believe in helping build people up.  


Except when that doesn't work.


And positive encouragement doesn't work with certain kinds of

smart people.  Some smart people (and lots of them go to business

school) have had too little failure in their lives.  They're so

successful in everything that they do, that they are not accustomed to

tough feedback, disappointment, gut-wrenching failure.  These smarties

develop an unhealthy fear of failure.


In my follow-up conversation with this student, we talked a lot about

the concept of iteration.  He had led his team through 4 weeks of

planning and discussion with no real output yet.  I told him to get

the team together and come up with a version in the next 3 days.

Whatever it is, at least then we could start iterating.  It made total

sense to me--enough planning, let's get to a minimum viable product!


His response took my breath away.  He said:


"If my team burns the midnight oil for 3 days, producing a deck and it

turns out to be no good, their morale will be crushed.  I can't do

that to them."


And that right there is fear of failure.  Five uber-smart,

accomplished people can't handle a tough round of feedback?  I highly

doubt that.  Actually, it's not fear of failure, it's fear of the

possibility of failure.


There are two massive implications to protecting yourself from

failure.  The first is that you limit yourself by choosing challenges

that are guaranteed wins.  You lose out on all sorts of experiences

that would've been incredible learning opportunities because you didn't want to risk failing.  


The second implication, which is far more dangerous, is that you actually believe

that your skills are limited.  When forced into new, tough situations,

you give up before trying.  Just think of how many times you've given up on

yourself without really testing your own limits.



I've failed at many, many things in my life.  I've become quite good at it actually.


I remember so vividly how I felt when my first company failed.

It wasn't just that the company had failed, it was that I had failed.

And in my mind, it was even more than that.  I had failed because I was

a failure.  I remember the regret I felt for skipping those traditional

business school job opportunities. Working at a consulting firm,

making a stable salary, and not failing.  In that moment, consulting felt like it would

have been the best thing in the world.  Instead, I was stuck in a very

lonely depression, unsure of what to do.


Funny thing though.  That only really lasted like 3 days.


Failure is like swimming in the deep end.  As long as you don't drown,

it's not as scary as you thought.  After 3 days, I called up my co-founders and we

agreed to do another start-up together--whatever that would be.  Four

weeks later, we started FlightCaster.


Entrepreneurs bounce back.




I had a really good talk with the MBA student leader a few days ago.  I

reiterated that I believed in him and that I am on his side, available

to help.  With half a semester left, he has plenty of time to bounce

back.  He had no plans to be an entrepreneur.  In fact, he picked this

project because he wanted to step outside of his comfort zone and

learn something new.  I am confident that he's going to blow

away all expectations, including his own.


This conversation just happened.  I've written this post before I

actually know if he is going to make it.  The team's final project

isn't due until the end of May.  I've asked his permission to

publish this post now, and I'll update you all in a few weeks with

their progress.



Find discussion of this post on Hacker News 

I'm Jason Freedman.  I co-founded FlightCaster.  
You can find me on Twitter: @JasonFreedman.
You can send me a Linkedin request or become my bff on Facebook
10 responses
well said, jason.

also, personal growth happens orders of magnitude faster in situations where failure is a real possibility.

similar theme in another field: the class i teach in the spring semester is the biology capstone course. the students are majority pre-med, and we make them research, design, execute and writeup a real ecology experiment in a semester. 95% aren't funded on the first round of proposal submission, and lots genuinely freak out about it. at some point they realize there is a real possibility that their experiment has already been done and they missed it, or that their organism won't grow in their conditions, or that the experiment won't elucidate what they thought it would. most of them hate the class, i think for the requirement of self-propulsion and direction as much as the critical feedback and workload. but, at least for the students who really engage, we see tremendous growth -- as scientists, as writers, and as people -- over the course of four months. in a traditional class, where the direction is given by the instructor and success is more-or-less guaranteed by effort, there's no way we'd see the same development.

> I remember the regret I felt for skipping those traditional
> business school job opportunities.

Thank you for posting this. I REALLY had to read something like that these days. I believe it is one of the coolest texts I have read all year from blogs. Exactly what was needed. I am going to check back soon!

Best, E.

So what happened? Did they make it?
So, where's the update? Curious how it worked out.
6 visitors upvoted this post.