Better Together: If at first you don’t succeed – GREAT!

A bi-weekly column exploring the intersection of entrepreneurship and community by Sam Davidson

If you want to succeed, you have to fail.

I don’t mean you have to be willing to fail. I mean you have to actually fail. At least, that’s what the research shows.

Check it out: “Among the founders of billion-dollar startups, almost 60% were not first-time founders.” (link to Medium)

But failure matters not just because you might create a unicorn the next go-round (that’s supremely rare no matter what). It matters because without failure an entrepreneur may not build the resistance they need to put up with all the other obstacles inherent in entrepreneurship: rejection, competition, learning curves and pivots. 

In fact, those four things can cause failure in themselves. Fail once, shame on them; fail twice, shame on you. Fail three times? Well, let’s make that difficult to do. 

That’s because failures “generate systemic learning about where opportunities are (and are not) and how to address them, and they quickly free up people, capital, and ideas for more-promising projects.” (link to Harvard Business Review)

And we’ve heard it first hand. Recently, we’ve shared the stories of those who have tried, failed, and tried, tried again. For example:

1. Entrepreneurs’ Hall of Fame inductee, Jim Ayers, shared at the 2023 NEXT Awards, ‘If you don’t have some failures, you’re not gonna be an entrepreneur. It’s just part of it. On your losers, don’t be afraid to cut ’em short and get out. And you let the winners run.” Listen to his full Circle Back podcast story. (link to podcast)

2. Serial entrepreneur Josh Mundy says, “Entrepreneurship is so hard man, it’s just so hard. And so there was a lot of times where I second-guessed my intuition, and your intuition speaks loud to you. It talks to you very loudly, and you can choose to ignore it, or you can follow your gut.” Watch his full interview. (link to video)

3. Serial entrepreneur Chris Thomas shares, “If you are constantly thinking about your fallback system, I don’t know that you’re in the best mental place in order to try to make the headway you need to make. So I was convinced I was never going back to that life.” Watch his full interview. (link to video)

Next up on our storytelling hotseat will be Sherry Deutschmann, a serial entrepreneur, author, and passionate advocate for entrepreneurship, will be sharing her serial entrepreneur journey over cereal on March 7. It’s a free event and you won’t want to miss it. Register here. 

There’s power in getting back up. And it’s best done with a helping hand. Proving once again that entrepreneurs are, in fact, better together.