In the first posting of this series, a sixth-grader showed us how the mind of an entrepreneur works–imaginative, customer-oriented, and opportunistic (in a good way).

In the second posting, we saw how one Millenial uses his resourcefulness, curiosity, and team-oriented leadership style to shake up the music industry's way of finding up and coming bands.    

Much has been written about the joy of being an entrepreneur, the glory and positive impact when successful.  But I'm curious about the flip side.  What happens when things get difficult? Photo by alaina.buzas

In this third and final posting of this series on the different faces of entrepreneurs, we explore the messy side of entrepreneurship–when things go wrong.   It's a big topic, one that all entrepreneurs face, and one that I've been living with over the last few months.

The more I talk to entrepreneurs, the more I admire anyone who tries their hand at starting a business.  Often, things get messy when assumptions (spoken and unspoken) are proven wrong. This creates situations where there are no easy answers and all the choices are unappealing.  I've used pseudonyms below to protect the privacy of entrepreneurs who were willing to share their stories.

"Joanna" assumed that building a business could fit into the life of a mother raising three children under the age of 7 and the role of a supportive spouse to a serial entrepreneur, who hasn't taken a salary in years.  Her assumption was wrong.  She wonders when it will be her turn again, when she'll have enough financial and mental runway to get something off the ground. In the meantime, she's looking to return to a previous employer, on a part-time basis. 

Returning to work for someone else is one that Mike knows all too well. He spent nearly three years trying to get traction on a bootstrapped startup that he described as a "Open Table Meets Yelp" for the XYZ industry.  His spouse worked in the startup, while holding down a full-time job, and eventually, both lost the juice to continue.  Mike now works at a thriving Silicon Valley Internet company. 

This option–dropping out for period of time in exchange for steady paycheck–is one of the little talked about paths for entrepreneurs. Photo by bradleyolin.

And then there's "Louise", who found out that assumptions about the adoption rate of her recommendation sharing service and the ability to sell sponsorships were both wrong. Louise needs a new business model and she needs to prove it out, quickly.  Funding this business on her own, she's run out of time.  Like many entrepreneurs, Louise has plenty of experience in the corporate world, working inside established companies, where unprofitable projects go on for far too long.   In the start-up world, trial and error must proceed at a much quicker pace.

"Dan" also knows the value of time in a start-up.  He's been working on a software start-up for over four years, aimed at serving university students.  His wrong assumption?  The adoption rate of free software that helps to recover lost laptops.  He recently remarked, "If you looked at my website, you'd think I was driving around in a BMW.  Instead, I've got a car that has 160,000 miles on it where the door doesn't open without a good jiggling."  He's emotionally drained, trying to figure out how to make his start-up profitable, with less time invested and better results. He's a serial entrepreneur, using his first company, established decades ago, to fund his start-up and now on the lookout for external funding.  

Neither Dan nor Louise have lost their optimism for what might be around the corner, with the right packaging, a strategic trade show, or a different market. In a ten-round boxing match, they are willing to come back for rounds two and three, after getting punched in the stomach in round one.  They are smarter, and hopeful that learning from their experiences will make the difference in the long run.  Photo by _Fidelio_

"Patty" took a different route, having built a thriving company over seven years, one where venture capitalists were willing to invest.  And then she burned out. Her personal life with her family had suffered considerably.  She took a year and a half off to rejuvenate.  Now, she helps other small business owners avoid unnecessary struggle and depletion. 

In each of these stories, the way that entrepreneurs respond to the messiness is familiar and yet, uniquely their own.  They take a job, continue with another trial and error, or in extreme cases, drop out completely.  One option is not better than the other, but rather a response to the circumstances at the time and what's best for an individual, personally and professionally. Photo by Noobins.

To hear these stories, one might want to quit before even trying.  Yet, my friend, "John", a seasoned serial entrepreneur, provides another perspective.  John is working on his sixth business, and is known for being meticulous about measuring the right things.  He lives close to reality.  He's gone more than a few rounds in the boxing ring and could tell me ten more stories for every one that I've relayed here. He also found success right out of the chute, with his first company, started in college and sold in his thirties.  

What intrigues me is that John has also had his share of failures, when things got difficult, and the only choice was to move on.  Success is no insurance against failure.  And failure isn't a pre-requisite for success. 

A few of John's perspectives that I found fascinating:

• On the need to prove something: "All entrepreneurs have something to prove.  It's part of what makes them an entrepreneur."

• On not having control and humility:  "Expect that things can blow up at any time."

• On the lifecycle of companies: "Companies go through a cycle, starting with the excitement and thrill of starting up and growing.  Then it matures and at some point, chaos comes.  During the chaos, which is really no fun but it always comes, we remember the excitement of starting up and growing.  That's what keeps us going.  And finally, something dies–some part of the company or the company itself. Until something else is born.  Then the cycle starts again."

• On persistence and failure: "Each time we go into the ring, we know there's a chance of getting beat up.  And each time we get beat up, it's not as bad.  But we still get beat up. We all experience failure in our lives, but failure as an entrepreneur is a lot more visible."  Photo by bolhav
  

What I've learned from John and others is that those who endure failure best are the ones who win.   They are able to see failure not as a personal indictment, but as a sign that something needs to change in the equation.  They are able to cut bait, when they've sunk time, energy and money into something that isn't working.  No small feat.  Emotional attachment is both a blessing and a curse for entrepreneurs.

Seth Godin's newest book, Poke the Box, underscores the importance of failing.  A few choice quotes:

"The person who fails the most usually wins. If you fail once, and big, you don't fail the most. If you never fail, either you're really lucky or you haven't shipped anything. But if you succeed often enough to be given the privilege of failing next time, then you're on the road to a series of failures.  Fail, succeed, fail, fail, fail, succeed–you get the idea." 

"Talk to any successful person.  He'll be happy to fill you in on his long string of failures."

"I started a record label, and failed.  I started a fundraising business based on light bulbs, and failed.  Launched the first aquarium on a VHS tape and failed.  Published many books and failed. The winning part?  I learned from each of these failures."

This is the essence of entrepreneurship–trial and error.  Being keenly observant, willing to face reality, humble enough to know that even smart people get hammered, creatively resourceful, and adapting quickly.

Why do it?  Why go through the pain?  I can think of no better reason that this one, from Pam Slim:  

"Entrepreneurship, at its heart, is aligning your purpose for being on earth with a business idea that is so compelling that you must do it, despite the fears that hold you back."

 Photo by @boetter.