THIS ADVENTURER AND SERIAL ENTREPRENEUR IS NEVER SATISFIED.
BY MATT CROSSMAN
Entrepreneur Steve MacDonald inched his way up Cotopaxi, a 20,000-foot tall volcano in Ecuador. He was tied in to his fellow climbers, and at best, they covered 50 feet per minute, one halting, shuffled step at a time.
Darkness engulfed him on the slow and treacherous climb. He looked up toward a peak he couldn’t see. He looked down at the edge of an ice shelf, and couldn’t see that either. Exhaustion swallowed him, taunted him, told him to give up. “You look down and say, I can go back down. But you also realize, if I [mess] this up, I’m literally going to slide off this mountain, and you’ll never see me again.”
This is the dilemma every entrepreneur, solopreneur or side-hustler faces. To succeed requires a fight into the unknown. Giving up is equally perilous. MacDonald turned his thoughts from quitting to pushing for the summit.
Some 400 feet before reaching the top, the climbing team accepted that they would run out of daylight before they could reach the summit. This personal apex would have to do, and it was no less breathtaking. The clouds cleared. Getting to this point had been miserable, cold, arduous, dangerous… and awe-inspiring. MacDonald looked at the world below him and thought, If I can persevere through this climb, I can do anything. “Although it’s just one day in your life, it’s something you always reflect back on,” he says.
Indeed, the fortitude MacDonald built on the ice-slicked side of Cotopaxi helps him weather tough times in business. But the opposite is also true: MacDonald has withstood being fifired from a company he founded while simultaneously going through a divorce, and that experience has increased his mental strength. He credits it with helping him complete marathons, ascend high peaks and withstand frigid temperatures. “Each of those things is like building blocks,” he says. “They prepare you for the next thing.”
Perseverance is a unique trait in that the only way you find out you have enough of it is the exact moment your career, if not your life, requires it. MacDonald says he first showed such grit as a young boy, when a bigger kid wanted to beat him up every day. He responded first by trying to outrun the bully and then by lifting weights to get stronger.
He wasn’t tested again until he was in his late 20s. In 1999 MacDonald quit a good-paying job to start TechHealth, an online community for people with catastrophic injuries. Eventually he lost leverage on the company’s board and was forced out. He woke up every day not knowing what to do. He sometimes wanted to give up and go back to the safe corporate job he had left behind.
He resisted that urge. He saw himself like a bird on its first flight—there was no way to go back to the nest. “Pivoting my life away from what I thought I was doing and finding the next new thing—perseverance is what got me through that,” he says.
He started another company, myMatrixx, a pharmacy benefits firm, in 2001 and sold it in 2017, exiting with $250 million. After navigating a career packed with outdoor adventures and business variety, he now runs MacDonald Ventures, where he pursues his passion for startups as an angel investor. He speaks often on investing, entrepreneurship and the startup mentality.
When times are tough, MacDonald repeats to himself a mantra he learned on slopes and in boardrooms, mountain sides and conference calls: Enjoy the ride. “I know this is going to be hard,” he says. “But I’m going to look back on it and say, this is the best ride ever.”
That’s why he can say being fired was the best thing that ever happened to him and describe an adventure like Cotopaxi as physically and mentally excruciating while also making clear he loved it.
“The suffering is what makes life beautiful,” he says. “A lot of people don’t have any desire to appreciate life like that. They’d rather sit in a chair and watch TV. People who really aspire to suck as much life out of life as they can are people that in the end are ultimately happy. Adversity creates the best memories.”