Success and Failure: Two Sides of the Same Coin

I’ve spent the better part of the last two months oscillating between two extremes -

  1. Take my ball, go home, and never play this game again
  2. Figure out something bigger and riskier to do in order to prove to people that I’m smart

Neither of these are the right decision or even healthy for that matter, but it’s hard to control the inner dialogue. When I set out to take my most recent at bat as an entrepreneur, several choices were made.

First, the choice of B2C vs B2B. I’ve spent my entire career in B2B marketing software and services. To be honest, I was bored. I feel like I could have chosen an easier path by building something I was familiar with, pitching it to investors that invested in that space, and selling it to a network I had already established. But again, I was bored.

Second, was the choice to raise outside capital. With every other business I’ve started, I used my own money and bootstrapped. Taking on other people’s money was challenging on multiple fronts. Not only did I have to paint the vision and get them to believe, I also had to live under the pressure of every decision made potentially resulting in a 100% loss of their capital. That’s not for the faint of heart.

Sugarcoating Failure

I’m not one that likes to sugarcoat anything. At the end of the day, my startup failed, and that sucks. However, along the way, I learned so many lessons of what I would and wouldn’t do the next time the opportunity presents itself. I talked about a few of those already and will be writing more as time goes on. What is really important to me now is that we acknowledge the role failure plays in building something from scratch. Let’s not sugarcoat it. Accept that our attempt failed — own it and learn from it.

Mark Suster wrote about this, saying, “It seems plausible to me that a scientific community built on the principles of trial-and-error (emphasis on the latter), measurement, refinement, discovery and then scaling around the very few ideas that actually worked would breed a strong culture of tolerance for things that didn’t work but for which strong effort and rational thinking went into the failure. If you were a science man and you failed by proving a hypothesis was incorrect — that was ok! And if you had the right credentials to lead people to believe that your next idea was more likely to be right than other people’s ideas then you were certainly backable.”

The Man in the Arena

I used to be overly critical of what I considered the “dumb” mistakes entrepreneurs made. I’ve realized now though that being in the game and grinding day-to-day is a hell of a lot harder than sitting on the sidelines and watching, or even being an employee of the company and thinking the founders were idiots. I’ve gained a lot of empathy for those willing to quit talking and actually put in the work.

Several people much smarter than me have pointed to the Teddy Roosevelt speech from “Citizenship in a Republic”:

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.

What’s Next?

As I had conversations with my investors after the business failed, we talked through a lot of the things that were learned. I was constantly asked “what’s next?” I didn’t have an answer, but was shocked to have over half of them say, “well, whatever it is, let me know and I’ll write you another check.” WHAT? This made no sense to me.

That’s when one of them said, “Jim, how old are you?” After replying I was 33, he said, “let me tell you a story. When I was 34, I was bankrupt and had lost a lot of people a lot more money than you did. My next company was ExactTarget.”

That definitely put a lot of things into perspective.

Common Sense

This experience and ultimately, failure, has allowed me to grow in ways I never anticipated. The wisdom I’ve gained taking the rollercoaster ride, combined with the collection of lessons learned throughout my career (and life) now seem like common sense. I hate the expense of what it took to get the education, but I’m extremely grateful to be surrounded by people who believe in me.


About Jim Brown — Experienced Marketing and Sales Leader

After attaining the rank of Sergeant in only four years of service in the United States Marine Corps, I’ve spent my entire professional career in sales and marketing. I’ve had the fortune to consult companies like FedEx, 3M, Sears, Claire’s, ADT, HHGregg, Cummins, and Ingersoll Rand on how to increase their revenue on the internet.

Most recently, I raised over $1MM to help start Haven, a company built on combining public and collected data to anticipate the needs of homeowners and help them manage their largest asset — their home. Without significant traction or the ability to raise additional capital, Haven was shut down in August.

Let’s connect on LinkedIn or Twitter.

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