Entrepreneurship, Personal

In the Trough

What comes next? You’ve been freed. Do you know how hard it is to lead? You’re on your own. Awesome. Wow.  Do you have a clue what happens now?

– King George, Hamilton

Last month, I reflected on my experience in the UChicago New Venture Challenge.  Hopefully that gave you a deep cut into what people actually do in accelerators, and what kind of programming can help fuel a business startup.

But something I am grappling with now is different: what comes next? After all the cameras are put away, the free food eaten, and the coffee meetings taken, you have to get back to the business of building a business. So, what do you do?

Here are some things that I’ve done in the last month (in no particular order):

  • Ordered chairs and monitors
  • Hired accountants
  • Printed and signed more documents than I can count
  • Seen Hamilton with my wife
  • Gotten a haircut

It sounds silly to enumerate it, but I think it’s a really important topic that no one blogs about.  There are literally oh so many blog posts about the joys of fundraising and #StartupWinning that it’s easy to feel like the path to success is always up and to the right.  But did we all forget this?

Hopefully the Crash of Ineptitude is Not Literal

The period of time after the New Venture Challenge is what a lot of people have called “the trough of sorrow” or “the trough of disillusionment”.  Am I sad? Am I disillusioned?  Not really.  I’m very fortunate that I have a loving family and supportive peers.  But, I am definitely in a trough.  There is no way to sustain the breakneck excitement and pace of an accelerator like NVC.  In fact, you wouldn’t want to.  The point of accelerators is to temporarily accelerate development.  You make a trade-off, sacrificing things like technical debt and incomplete financial models for current growth or capital.

So after your TechCrunch moment, it’s important to realize when you may have entered the trough.  Being in the trough feels like checking emails multiple times an hour but your inbox doesn’t update.  Being in the trough feels like sending colleagues emails that they don’t respond to until they return from vacation.  Being in the trough feels like missing spontaneous phone calls that supportive peers and mentors might have made before.

Personally, I am dealing with this by reminding myself of things I have to be grateful for (not surprising, given the psychological research showing this is a vital part of wellness).  But another important part of this experience is to admit that you’re in a trough and just roll with it.  It does such a disservice to entrepreneurs nowadays that we expect everything to be #disruption, YCombinator, and massive massive massive fundraising rounds.

Building a business should, in my opinion, be about building long-term value for people for whom you want to change the world.  That often comes with periods of intense dedication and sacrifice to get your startup where it needs to be.  But the investor and entrepreneurial communities should present the situation with a little more balance.  Instead of expecting breakneck awesomeness that never stops (which can only lead to inevitable disappointment and schadenfreude), we should expect businesses to be punctuated by intense periods of deceleration to complement hard work. Acknowledging that reality is the first step.



New Year’s Redirections

Now that the New Year is here, it’s time to set our resolutions.  I’ve got mine – stop biting my nails for the love of – and I think that’s good.  New Year’s Resolutions count toward the first half of my inaugural post: self-improvement. These are the things we look forward to trying and trying and trying (and hopefully one day succeeding) at.

But I think there’s a problem if we only focus on self-improvement.  What about the other half of my original discussion: self-acceptance? When do we stop trying to improve, and start trying to accept? And how do we know what to accept and what to reject?

For me, I’m looking forward to the second half of my New Year, what I am calling “New Year’s Redirections”.  The concept is simple: see where you can redirect your time or money that would be spent on marginal self-improvements into high-return self-acceptances.  For example, there is a lot of time I could spend on getting in shape.  It’s a noble goal, and New Year’s Resolvers set out year after year to do it.  However, I think my professional Javelin days are long behind me.  My odds of making USATF, sadly, are about as high as the odds of me giving up Honey Butter Chicken (mmmmm) for an entire year.  So, in light of the fact that I’ll never be a professional athlete, what if I took a little bit of the energy I would spend fretting about diet and exercise and worry about appreciating my loving wife and my adorable dog? It’s trite, sure, but it helps to redirect energy into things that make you feel good about yourself, and the place you’re at in life.

I think this is related to a concept that was popularized by Newt Gingrich during his time as a U.S. Congressman.  In the parable Gingrich tells, a lion goes hunting and catching field mice all day long.  However, because the lion burns more calories killing the field mice than the meals provide, she slowly starves to death.  If only the lion had realized that the antelopes, despite requiring a little more cumulative effort and skill to kill, provided far more energy than they took to hunt, she would have thrived and grown strong.

The other day I was in class and started to space out during lecture.  Stressed about my internship, my startup and my classes, I started to get dizzy.  But, I took a second to redirect myself and realized something amazing: the wireless headphones I have are super dope.  This sounds stupid I know, but let me explain.  Before my in-laws gave me an awesome Christmas gift (these insanely awesome LG/Harman Kardon headphones), my old school headphones would constantly get bumped out of the socket when I walked around Chicago.  I would then have to reach into my phone, reconnect them, find the correct spot (or fumble with bulky gloves in a narrow pocket) and resume my listening. Now, thanks to my wonderful in-laws, I don’t have to worry about that crap.

It’s hard to admit that we have it good in life.  Sitting around talking about how privileged we are (to be born in America with opportunity, let alone to be at great universities or well-paying jobs), can make us feel terrible about our inner ambitions.  I don’t think there should be this conflict.  We can still feel that life requires us to fight and strive, while being able to redirect what would be wasted energy toward the things in life that make us happy, grateful, and whole.

My life got a little bit easier due to something wonderful in my life: a great, supportive family that knows how to buy a great holiday gift. For that I’m grateful.  My hope is that this New Year’s season, you can redirect wasted energy toward appreciating the things, even a pair of headphones, that make your life better as well.