What boxing has taught me about business

Ryan Sheffer
3 min readApr 23, 2015

Take punches. Chin down. Move forward. Wait for the opening.

by Ryan Sheffer, Co-Founder Momunt

3 years ago I walked into a boxing gym and couldn’t jump rope. One of the coaches at the gym called me the most awkward boxer he had ever seen. My first sparring session was with a woman and I unintelligently assumed I would have to go easy on her. She beat me up.

Today I am comfortable in the ring. I don’t compete, but I know I could. I spar when I have time, and I box as many days per week as I can.

Here’s the key to boxing — when you get into the ring, you have to do the exact opposite of what your instincts tell you to do. Your brain tells you to lift your chin up and push the opponent away. To move away from the fight at all costs. What you have to do is take a few punches, put your chin down, move forward, and wait for the opening.

You have to go towards the fight — when it’s scary, when you don’t know if you’ll win.

The point here is this: you don’t win the first time. Maybe — just MAYBE — you do. But then you’re a lucky fuck. Or a genius. Very few of us are either.

Rather, the majority of us will take punches. We will fail repeatedly. Most of us will quit.

But the people who smile after the punch; who get back up, learn from their mistakes, and move forward with their chins down, will succeed.

I have yet to succeed to the degree I intend to. But my own boxing experience coupled with what I see around me in business leads me to believe these concepts are true.

Chris Sacca discusses his investments with Jason Calacanis on TWIST

Take Chris Sacca — he was famously a 20-something in debt to the tune of four million dollars because of some problematic investments in the stock market. Today, after many very successful tech ventures, he is rightfully looked upon as one of the most successful investors in the world.

I’m not sure there’s a bigger punch to take in business than being in debt for multiple millions before you hit 30. But I do know this: if he hadn’t gotten back up, lowered his chin, moved forward, and waited for the opening, there’s no chance he’d be where he is today. You can check the whole story in Sacca’s episode of This Week In Startups with Jason Calacanis.

Or what about Elon Musk? After a very successful exit with PayPal, he put his sizable personal fortune into Tesla. Today, Tesla is a massive success, but only a handful of years ago Musk and the company had zeroed their bank accounts.

Just a couple of the characters created by this man who “lacks imagination and creativity”

My personal favorite story of failure before success is Walt Disney, who was fired from a newspaper for lacking imagination and creativity. I don’t need to tell the rest of that story.

When times are tough for myself or anyone else at Momunt, we try to remember that we’re just taking punches. We’re constantly pushing forward with our chins down. Waiting for the opening.

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