Entrepreneurs

Unwound: One Founder's Story of Finding Success in Failure

Three things all entrepreneurs need to know to cope with big wins and big losses in the business world
Unwound: One Founder's Story of Finding Success in Failure
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Head of Alternative Lending at Marqeta
5 min read
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As an entrepreneur and writer, it is much easier to share my successes. Stories of overcoming obstacles, closing big deals and winning the gig always seem to be more interesting than episodes in which I’ve failed or lost. But as I look back on my life, the moments that taught me the most are consistently those that were the most painful.

I have started three companies (so far), of which two were minor successes and one was a huge failure. I recently found myself reflecting on that failure with a good friend and former colleague, Ethan Senturia. Senturia was a founding member of one successful startup, Ampush Media, and a founding CEO of one failed startup, Dealstruck. Fresh off defeat, he recently published a book, Unwound: Real-time Reflections from a Stumbling Entrepreneur, in which he explores success in the entrepreneurial life through the lens of its opposite.

I found Senturia’s perspective refreshing. Rather than lamenting or avoiding failure, he tackles it head-on with honesty, accountability and optimism.

“Trying again after winding down a company isn’t nearly as intimidating as facing failure and learning from it in the first place,” Senturia explains. “After closing the doors at Dealstruck, I spent six months asking myself, ‘What happened? What did I learn? What should I do the same in the future? What needs to change?’ That was the hardest part, but it allowed me to look at the experience objectively.”

“I wrote Unwound to create a more open, honest, vulnerable and transparent dialogue about failure. Most entrepreneurs have a story like mine. But, too often, they’re left untold.”

After speaking with Senturia and reading Unwound, I walked away with three tips that can help entrepreneurs live, learn and repeat:

1.  You are not your company.

We often hear the tired cliché that an entrepreneur’s company is their baby. But, this perspective can hamper you in some important ways. 

When raising money, for instance, the vast majority of investors won’t like your idea. Even the most successful entrepreneurs deal with this. When you tie yourself too closely to your company, you risk confusing their rejection of your business with a rejection of you and miss a valuable learning opportunity by doing so.

Identifying too closely with your company when things are going well also has its consequences. “I remember a time when I’d received an acquisition offer, closed a big fundraise, landed a world-class executive, and hit record numbers all within the period of a few months, and I thought to myself, This isn’t so hard!” Senturia continued, “But, right after that, things went sideways.” Startup success takes as much (if not more) luck as skill. Forgetting this can breed unwarranted overconfidence or comfort with the status quo.

On the flip side, when things are going downhill, it is critical to recognize that just because your company is failing does not mean you are, too. Realizing this will allow you to continue leading with poise and compassion when your team needs it most. “I had many employees who had a lot more on the line than their reputation. Worrying about myself would have deprived them of the support and comfort they deserved from their leader.” Your people need to know that you are willing to submerge your ego to help them land softly.

2. Nothing is ever as good or as bad as it seems.

The entrepreneurial existence is, by its nature, a bipolar one. Elon Musk described this best when he tweeted, "The reality is great highs, terrible lows and unrelenting stress."  

Senturia sees things differently. “After living this volatility during my five years at Dealstruck, I’ve realized that the high highs and low lows are constructs of our imaginations. Governing the size of our emotional swings is not only within our control, but also it is critical to staying focused, conserving energy and making well-thought decisions.”

3. Transparency is a double-edged sword.

Nothing can motivate startup employees more than bringing them close to the action. But, when things get hardest, sharing everything you are experiencing and feeling with your teammates can work against you. “It becomes a challenging acting role where, in your head, everything is going wrong, the burn rate is too high, the product is not resonating -- but then your sales person walks in after closing a big deal with an ear-to-ear smile. I had to learn to mirror that excitement even when it wasn’t real.”

Sharing bad news is one thing, but sharing really bad news is another. Do your best not to compound your problem by pushing unnecessary stress onto your faithful supporters.

When Senturia thinks about the entrepreneurial life now, he doesn’t see Ampush or Dealstruck as their own isolated instances. “You have wins and losses. That is a certainty. But if you can frame each adventure as a chapter in your larger novel, you will always be able to swing again.”

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