Handling the ups and downs of startup life


Being an entrepreneur is hard.  The ups and down of startup life are far larger and stronger than most jobs.  Working with entrepreneurs isn’t much better, as the empathy is almost are wary.

We’ve worked with dozens upon dozens of entrepreneurs at Fledge and most handle these stresses in stride.  Sure, they have some sleepless nights and exhaustion, but that is what “stride” looks like for successful entrepreneurs when the downs hit.

The ups are all the same.  Cake and/or drinks.  Sometimes a nice celebratory dinner.  Then back to work for the next up or down.

The downs are all different, and unfortunately there isn’t a way to know how anyone is going to handle those before they arrive.  Here are a few patterns we’ve seen:

A- Continued optimism.  Entrepreneurs tend to be optimists.  They tend to have a vision and expect it to happen.  So when the downer arrives, they brush it aside and keep moving forward.

B- Visible frustration.  We had a fledgling once working with a new venture capitalist on some follow-on funding.  Every two weeks the VC would ask for one more thing.  Or they would go silent for two weeks while traveling.  Months went by with repeated assurances the deal would imminently close.  Nine months went by consoling this clearly frustrated fledgling, who just wanted to get going and build a bigger business.  Down after down until finally the VC sent the final email, bailing on the deal altogether.  Luckily one of the Fledge funds was the planned co-investor, so we were able to get past that huge downer with some immediate capital and a new lesson in venture capitalists.

C- Dogged persistence.  A few fledglings have dealt with issue after issue after issue.  Issues like broken machinery, employees not doing their job, customers not paying on time, landlords selling the building and not renewing leases.  We’ve counseled fledglings who have taken their persistence to the brink, who have told us their wife is threatening to leave, who we have told family is more important than business.  More often we counsel fledglings who keep finding a way to move forward, overcoming the issues, dogged in their persistence until the down turns around.

Then there are the most destructive patterns:

D- The world is wrong.  One fledgling didn’t believe us when we explained the Realities of Funding.  We got him far enough through that process to find an investor, then didn’t believe us when we explained the importance of having a good relationship with your investors.  When any issue arose, the entrepreneur always thought he was right, never bothering to look at the issue from another perspective, often banging his head against the proverbial wall demanding the world was out to get him.

E- Internal ups and downs.  We had a fledgling who we discovered was bipolar.  Diagnosed and medicated.  We met the entrepreneur on a high and he stayed there throughout the whole program.  He was wonderful.  Then soon after the program ended came the low.  Internally generated, not from any outside issue.  No one wanted to be around him, let alone work with him.  The team fell apart and the startup abandoned.

F- Self destruction.  We had another fledgling who took destruction to the next level.  Not only did he see the world as wrong, but mistook our advice for threats.  All optimism gone, all persistence used up, he decided to send angry emails, break contracts, and head down a path where all chances of success truly are lost.

The world is complex and thus there are probably yet-more patterns to be seen in the future.  Meanwhile, startup life will continue with its ups and downs.  We’ll continue to try and help entrepreneurs avoid those down, and worst case we’ll keep looking for ways to help entrepreneurs keep their cool when the path heads downward.

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