Where CEOs Find Time for Triathlon Training and Motorcycle Racing
Leaders with epic hobbies seem to squeeze more hours out of the day than the rest of us
Leaders with epic hobbies seem to squeeze more hours out of the day than the rest of us
Many of us can barely keep up with our jobs, never mind hobbies. Yet some top executives run marathons, wineries or music-recording studios on the side. How can they have bigger responsibilities and more fun than we do?
It can seem like ultrahigh achievers find extra hours in the day. They say they’ve just figured out how to manage their 24 better than the rest of us.
They also admit they take full advantage of the privileges of being a boss—the power to delegate and the means to do things like jetting to Denmark for a long weekend of windsurfing.
Dan Streetman trains as many as 20 hours a week for Ironman triathlons in addition to his job as CEO of cybersecurity firm Tanium. It’s a big commitment for anyone, never mind a corporate leader who travels to meet with customers every week. He pulls it off by sleeping fewer than seven hours a night and waking around 5 a.m., planning his exercise sessions months in advance, and switching his brain from work mode to sport mode almost as fast as he transitions from swimming to cycling during a competition.
“I tend to work right up until the day of the race,” says Streetman, 56 years old. “I remember being on a board call on a Friday night, and Saturday morning was an Ironman. That’s just part of it.”
Ahead of business trips, he maps running routes in unfamiliar cities and scouts nearby pools, often at YMCAs. He rides stationary bikes in hotel gyms and, if they’re subpar, makes a note to book somewhere else next time he’s in town.
Leaders who eat, breathe and sleep business can appear out of touch at a time when employees crave work-life balance and expect their bosses to model it. Today’s prototypical CEO has a full life outside of work, or at least the appearance of one.
Their tactics include waking up early, multitasking and scheduling fun as if it were any other appointment. When you’re a top executive, hobbies tend to disappear unless they’re on the calendar. One CEO told me he disguises “me time” as important meetings. Only his assistant knows which calendar blocks are fake.
Ben Betts calls himself a “spreadsheet guy,” which is a bit like saying Michelangelo was a paint guy. With Excel as his canvas, Betts creates cell-by-cell checklists for just about everything he does, from cooking Christmas dinner to building a coop for newly hatched ducklings.
Betts, 41, is CEO of Learning Pool, a professional-development software maker. The duck home is part of his ambitious effort to restore an 18th-century farmhouse in England. He’s been renovating for about five years and aims to finish this fall.
On a recent Saturday, Betts’s spreadsheet called for stripping overhead beams by 5 p.m. so he could refinish them. Otherwise, the task would have to wait until the following weekend, throwing off his whole timeline. His vision of the home as a cozy enclave—completed in time for the holidays—can only come true if he sticks to a precise plan.
“Sometimes I stand in the doorway, and my wife probably wonders what I’m staring at,” he says. “I’m picturing us on a corner sofa with our two kids and the dog, watching a film in front of the fireplace I installed.”
John Sicard , president and CEO of supply-chain manager Kinaxis , got back into drumming many years after he let go of his dream to become a professional musician. He practices almost every day, but his sessions sometimes last only 20 minutes. He rehearses with bandmates two or three times a month. That’s enough to prepare Sicard, 61, to play Foo Fighters and Led Zeppelin covers at occasional charity gigs.
He also built a studio in his house, where he records up-and-coming artists. He finds time by sticking to this management philosophy: “The most successful CEOs do the least amount of work.”
For Sicard, that means letting his lieutenants take charge of—and responsibility for—their divisions. Many corporate leaders work harder than they need to because they micromanage or hire poorly and pick up the slack, he says.
Thomas Hansen , president of software maker Amplitude, is back to windsurfing, a sport he competed in as a teenager. He lives near the ocean in California but gets out on the water only about once a month, when the waves are just right. Hobbies don’t need to be daily activities to be fulfilling, he says, especially if they require training regimens.
To stay in shape for windsurfing, he rises at 4:30 a.m., seven days a week, for an hour of exercise. Hansen, 54, also guards his Saturdays and Sundays like the crown jewels of Denmark, his native country, limiting himself to two working weekends a year. Things that feel urgent can almost always wait till Monday, he contends.
When Christine Yen isn’t calling the shots at work, she’s circling a racetrack at 80 mph on her Honda CB300F motorcycle. The co-founder and CEO of Honeycomb, which helps engineers diagnose problems in their software, took up racing a few years ago.
Prepandemic, her motorcycle was strictly for commuting in San Francisco—and making an impression. She loved pulling up to investor meetings in her hornet-yellow helmet and leather riding suit.
“It fits me like a glove, and it makes me feel like a badass,” says Yen, 36.
The keys to spending full days at the track are planning and being willing to work at odd hours, Yen discovered. Her favorite track publishes racing schedules in 10-week batches. As soon as a slate is released, she circles the dates when she expects her workload will be lightest, aiming to participate in roughly half of the events.
“I have also been known to bring my laptop to the motel and get some work done in the evenings,” she says. “It sounds boring to say hobbies can be scheduled, but that’s how I protect my time.”
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Artificial intelligence is making it easier than ever to build a business without building a team. As AI takes over coding, customer support, marketing, administration, and other day-to-day tasks, a growing number of solo founders are scaling startups to millions in revenue with few—or even no—employees. While the trend is lowering barriers to entrepreneurship, it is also reshaping hiring, raising questions about the future of work and how businesses will grow in the AI era.
Ben Broca launched a company last December that offers AI tools to entrepreneurs. He’s already added 10,000 paying customers and is on track to bring in $10 million in revenue this year.
One thing he hasn’t added: any other employees.
The 40-year-old is part of a class of entrepreneurs who are launching, and then often running, new companies on their own. Artificial intelligence tools answer Broca’s emails, help write and debug code, field requests from customers, sign up new subscribers and grant refunds when issues arise.
Broca relishes his ability to make whatever decisions he wants on his own, often from his sun-drenched Sausalito, Calif., living room. “I think compromises make lukewarm results,” he said.
Once upon a time, running a business of a certain size required a team. AI is turning that assumption upside down, and more aspiring entrepreneurs are going it alone.
An analysis by the payments company Stripe shows there are thousands of solo operators on the company’s platform that are generating over $1 million in revenue, with their ranks doubling between 2023 and 2025. The number of solo operators crossing the $10 million threshold nearly tripled in that same span.
In the past, people without business contacts or particular savvy might not have known how to get their ideas off the ground, said Ernie Tedeschi, Stripe’s chief economist. “Now, AI can be a built-in business partner,” he said.
AI’s ability to handle various administrative tasks makes it potentially useful for launching solo businesses in many fields. But the technology’s ability to also handle key tasks in tech, like coding, make that field a particular hot spot.
Analyzing Census Bureau data, Bank of America Institute economist Taylor Bowley found that among all industries, new business applications in the information sector have seen the biggest percentage increase—nearly 45%—over the past year. At the same time, the rate of information-sector applicants saying they plan to hire workers has experienced the sharpest decline of any measured industry.
This Census dataset doesn’t track solo-operated businesses. But the numbers broadly show—in tech and beyond—that applications are flat among businesses likely to hire workers, but generally rising elsewhere. Economists say that’s a strong sign that solo operators are on the upswing.
“The bar for getting started has never been lower,” said Julian Weisser, who runs a San Francisco-based accelerator for solo founders working in tech. The accelerator—which offers founders seed money and mentorship in exchange for an equity stake—attracted 4,500 applicants for 10 slots made available in its most recent cycle, nearly five times the number it drew when it launched last May.
Going it alone with AI can still be surprisingly expensive. Broca said he was losing money on many customers’ accounts while paying to access Anthropic’s Claude to run his clients’ requests—that AI company, as well as others, charges based on usage. He has since switched to free open-source AI models from China.
Broca said he has raised $30 million from investors and, at the same time, has saved millions in salary since he hasn’t needed a team of software engineers.
Another risk: If it’s easy for one entrepreneur to launch an AI-assisted business, copying them can be easy, too. This creates anxiety for founders like Troy Johnston, who runs an AI-assisted business alone in Orlando, Fla.
“Everybody has the sword and we all have the ability to unsheathe Excalibur now,” said Johnston, 40, who used AI to code an app that helps people get the most out of credit card benefits. The company makes around $3,000 a month in profit, with no employees, and is continuing to grow.
What one-person businesses will mean for the labor market remains to be seen. Polling has shown Americans are worried that AI will replace jobs, and top economists are wrestling with that possibility, too. But AI is also creating lots of new jobs, and the go-it-alone entrepreneurs show how the technology can both open doors and limit employment opportunities.
“If everyone’s hiring less, but you get four times more firms, what does that do to head count?” said Rembrand Koning, an associate professor at Harvard Business School who studies entrepreneurship. He co-authored a recent study that found that among 50,000 startups the researchers examined, those focused on AI tended to operate with 25% fewer employees.
Koning also believes a soft hiring environment that’s left some people mired in long job searches has encouraged more to try their hand at launching businesses.
Some founders cite different motives. “It’s a perfect storm of post-pandemic burnout and a re-evaluation of one’s priorities, and also booming AI and a sense of what’s possible,” said Samir Ahmad, 39, who lives in Breinigsville, Pa.
Two years ago, Ahmad decided to leave the corporate job he had worked at Verizon for almost two decades to start a solo coaching and consulting business. He had been seeing social-media posts touting the ease and virtues of AI, which he used to chart a business plan and help with marketing. “It was like my chief of staff, a second in command,” he said.
The business ultimately petered out within months, though, and Ahmad is now back to a full-time corporate role with a utility company.
For Claire Vo, 41, AI helped her turn a passing impulse into a business. She was working full-time as a tech executive when she tapped AI in late 2023 to help code an app that would help her manage documentation and design for new products, with customers ranging from financial services to healthcare firms.
“I was copying and pasting from ChatGPT,” said Vo, who lives in San Francisco.
She put the app online for $1 a month, and within weeks people downloaded it thousands of times. Nearly three years later, Vo’s company—which she ran solo for nine months before hiring an engineer—now has 100,000 users and is on track to make seven figures in profit this year. AI handles the company’s marketing, sales and customer support.
While AI is a shortcut, Vo said her network and credibility in the industry were key. “I think people over-index on how easy AI is and under-index on how much I did to get to this point,” she said.
A divide has opened in the tech job market between those with artificial-intelligence skills and everyone else.
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