CrossFit training with… Okta CEO Todd McKinnon

Okta CEO Todd McKinnon
Courtesy of Okta

In a converted warehouse gym, for a brief moment, the stereo blasting Limp Bizkit cuts out. Todd McKinnon reaches down and frowning a bit, picks up a frayed loose wire next to his foot.

“Sorry about your cord, man,” he says apologetically. Focused on grabbing a barbell, he must’ve stepped on the cable. Chris LaLanne, the gym’s namesake owner, shrugs. “It’s okay, there’s a RadioShack on Market Street,” he says. McKinnon fiddles with the wire for a few seconds before the room fills with sound again. This time it’s Naughty By Nature. Problem solved.

We’re at McKinnon’s regular CrossFit class, which he attends five or six mornings a week. (Technically, we’re at the 7 a.m. workout, an hour later than his normal 6 a.m. start time, a gracious gesture to this night owl reporter.) Unsurprisingly, he knows most of his classmates. CrossFit athletes often talk about the camaraderie that forms during the partner-based workouts and because of the online scoreboards where you can track your results against those of thousands of other like-minded fitness buffs. “Once you know the people and the jargon, CrossFit is addictive,” he says.

McKinnon is also well known in Silicon Valley. In 2009, he co-founded Okta, a company that’s become a major player in the identity-as-a-service space. But he didn’t start out an entrepreneur. He had been head of engineering at Salesforce for six years before leaving the cloud computing giant to build Okta. This week, Okta announced it closed another $75 million round for a total of $230 million in venture funding to date.

Well before there were CrossFit facilities in every major city, McKinnon discovered CrossFit routines and tutorials online. LaLanne, a grandnephew of the “Godfather of Fitness” and juicing evangelist Jack LaLanne, spotted McKinnon performing the signature drills when the former was a trainer at Equinox, a Financial District gym housed in the old Pacific Coast Stock Exchange. The two became instant friends, even if it took a while for the workouts to catch on. “I didn’t know it would be so popular because it’s so hard,” says McKinnon.

McKinnon acknowledges that people think his training regimen can be cultish. But the intense workouts also keep him grounded and focused—so much so that he invested in LaLanne’s gym. “I just wanted a place to work out,” he explains. He likes that CrossFit members quantify every workout, and that there’s always that virtual scoreboard tracking your progress, both individually and against the larger group. Some of his buddies are in later classes. Mid-afternoon, he’ll start getting texts from a few, bragging about how they bested his morning stats.

Okta is often described as an identity and mobility management platform. As CEO, McKinnon envisions it becoming something much larger and more important: a universal layer that will eventually be part of the security foundation at most major corporations. What Facebook did for the social web and Microsoft did for personal computer software, McKinnon believes Okta can do for identity and single sign-on.

With major financial backing—$230 million in total venture capital, and the first investment Andreessen Horowitz made when the then-fledgling firm opened its doors in 2009—and a sky-high evaluation, Okta continues to inch toward an IPO. In late August, the company added a prominent advisor, former Amazon general counsel and senior vice president Michelle Wilson, as a board member.

McKinnon always planned for the company to gain major momentum. “In tech, the good companies get big,” he says. Size equals greater impact in the long term. In the same way, he notes, his workout is also scalable, explaining that the fittest person can enjoy the benefit of a tough CrossFit regime while a beginner can walk in and find sequences that are approachable yet effective.

At one point, McKinnon switches out his sneakers, lacing up Olympic weightlifting shoes that have a thicker heel and thus offer more support for squatting. LaLanne yells encouragingly from across the room, “Todd, keep your heels down!” McKinnon finishes a set, empties an energy gel into his mouth, and when I’m not looking, switches back to his other shoes. Then he begins deadlifting 125 pounds over his head. I count eight reps.

“I was surprised by how much I enjoyed the small company,” says McKinnon of starting Okta directly out of Salesforce, where he had led a team of 400. As Okta’s CEO, leading the company from a team of 15 to now more than 550 staffers, he’s had the benefit of being on another winning team.

“If the company is growing, you can manage through anything,” he says. “Once that stops, it gets challenging.” He pauses to note that once Okta grew to over 250 people, it required some executive agility to get back to managing such a large team. The muscle memory was there, but it took a bit of practice to get back into the routine.

LaLanne announces it’s time to pair up for some drills. “You can be my partner, and I’ll do all the work,” McKinnon offers gamely. Before I can object or agree, LaLanne walks over and offers to be his buddy’s partner instead. He grabs two 35-pound weights and takes off running, McKinnon right beside him. I turn on my heel to tag along, and we three jog out the door and down Natoma, the alley behind the gym.

I look over and see McKinnon grinning knowingly. “Chris is so psyched right now that he gets to work out.” When LaLanne sees me keeping pace and passes me on the turnaround, he cheers, “Atta girl! I love it!”

It’s nearing 8 a.m. and San Francisco is slowly waking up. A guy in a hoodie ambles past our pack of runners, and two neighbors and their dogs meet for a friendly chat and sniff. The next class begins to arrive, including a 20-something guy on a matte black Ducati that he rides right through the gym’s raised garage door.

Class is technically over, but McKinnon isn’t finished training. Instead of heading for the door, he walks back to an orange bucket full of chalk, pats his hands together, and leaps up and grabs two gymnast rings 18 inches above his head to complete one more set of muscle-ups. If he doesn’t keep ahead of his own personal best, his competitors just might catch up.

Subscribe to Well Adjusted, our newsletter full of simple strategies to work smarter and live better, from the Fortune Well team. Sign up today.

Read More

Artificial IntelligenceCryptocurrencyMetaverseCybersecurityTech Forward