Leaders with epic hobbies seem to squeeze more hours out of the day than the rest of us
4 min
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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AI-powered travel agents are challenging online booking platforms, but Airbnb’s exclusive listings and direct customer relationships could give it an edge. Its next challenge: turning repeat guests into loyal customers through stronger rewards and innovation.
3 min
AI agents like Muse can already find you the cheapest hotel room in Paris. But they can’t locate a cheaper version of that Catskills cabin you’ve been eyeing, because it might only be available on Airbnb ABNB -1.43%decrease.
Investors should pay attention to that distinction. When Meta Platforms META 3.38%increase launched its Muse agent last month, travel stocks including Booking Holdings BKNG -1.19%decrease, Expedia and Airbnb all fell sharply.
Airbnb, though, has a real chance to emerge as a winner from the upheaval. The catch: Its stock already reflects above-industry growth. To justify its valuation, Airbnb will need to turn repeat customers into loyal ones.
Online travel companies make much of their money by simplifying search and collecting fees on bookings. AI agents threaten that model.
But not all travel marketplaces are equally exposed. Booking and Expedia largely sell hotel rooms that travelers can also book directly or through competing sites. If an agent can find the same room elsewhere, it has little reason to favor either Booking or Expedia.
Booking and Expedia also sell sponsored listings that steer travelers toward particular properties. Wells Fargo estimates those will account for about 8% of Expedia’s revenue and a much higher percentage of profit next year.
Airbnb has more ways to adapt. More than half its listings are available only on its platform, and more than 90% of its traffic comes directly to its app or website.
The customer relationship doesn’t end after booking, either. Bernstein analyst Richard Clarke notes that 90% of Airbnb guests go on to message their hosts about arrival times, keys or local taxes, giving Airbnb a connection to both sides of the transaction.
How the companies have responded to the possible agentic future is telling.
Expedia quickly signed on as a Muse partner. Airbnb hasn’t, and Chief Executive Brian Chesky says AI chatbots have so far been a boon, sending customers to Airbnb’s website.
Chatbots might work for buying paper towels, he quipped at a Skift conference last month, but people enjoy planning trips. He argued that browsing dozens of homes isn’t something a text-based chatbot is well suited for.
Still, the AI jitters arrived just as Airbnb was persuading investors it deserved its pricey multiple. For years after its 2020 initial public offering, the stock—which trades around 25 to 30 times forward earnings—went nowhere. Investors saw a mature operator trading at a growth premium.
This year, Airbnb growth seems to be accelerating. The stock jumped in August after the company raised its full-year revenue-growth guidance with its second-quarter results. Wells Fargo analyst Ken Gawrelski credits a run of product improvements under a revamped leadership team.
Among the changes: letting guests reserve now and pay later, adding hotels, and a redesigned home page and app. Investors were also betting on what comes next, including thousands more hotels, car rentals and, eventually, advertising.
The irony is that some of those growth drivers push Airbnb closer to the kind of business Booking and Expedia run—the kind of business AI agents could threaten. Even if AI agents capture a large share of travel planning and booking, Airbnb would capture the demand. But it and others would slowly lose control over how customers find and choose properties.
That would undermine the advertising opportunity investors are counting on. The bigger point for Airbnb and other marketplaces is that losing control of customer acquisition could mean surrendering some of their pricing power and margins.
To bulletproof itself, Airbnb might look to another e-commerce giant that has so far kept AI agents at arm’s length: Amazon.
Like Amazon, Airbnb has a loyal customer base and hard-to-match supply. But it has nothing like Prime membership to make customers think twice before taking their business elsewhere.
That is where loyalty comes in. Business travelers stick with Hilton or Marriott because enough nights earn them perks. Leisure travelers rarely accumulate stays with one chain. Airbnb has millions of listings and plenty of repeat customers, but no broad rewards program. It has begun experimenting with credits on hotel stays, but it should make loyalty a priority, not just a promotion.
Airbnb also plans to launch its own AI agent next year. But travelers using an agent might still want it to search Airbnb, Vrbo, Booking and hotel websites alike, rather than limit itself to one company’s inventory.
Eventually, Airbnb might have to strike deals with agent makers, using its unique homes as leverage to negotiate favorable terms, says Gawrelski. Such deals, along with rewards for loyal guests, could over the long term eat into the company’s roughly 13% take rate, he adds. But if they bring in enough additional bookings, the trade-off could be worthwhile.
History offers a reason not to panic. The shift from desktop to mobile unsettled investors in Alphabet and Amazon, but both emerged as major beneficiaries. Companies with valuable assets can come out of a platform shift stronger, if they adapt quickly enough.
Airbnb has homes the bots can’t easily replace. Now it needs to give guests a reason to insist on booking them there.
