What would you do if you had a six-figure salary? Perhaps you’d never cook another meal or indulge in a monthly Thai massage and a Soho House membership to unwind from the stress that comes with being on your A-game.
Here at The Good Life you don’t have to imagine what life at the top looks like anymore: Get real-life inspiration for how the most successful live their lives.
Today Fortune meets 44-year-old Howard Lerman, an entrepreneur whose first company, Yext, has an over $800 million market cap.
While an undergrad at Duke University, Lerman founded his first-ever company with two classmates, a website called JustATip.com that lets users send anonymous comments to each other—positive or negative. Before they’d graduated, Lerman and his cofounders had sold the company for $150,000 to Traffix, a publicly traded marketing service.
After Duke, Lerman co-founded Yext, a SaaS company focused on lead generation, in 2006. He ran the firm as its CEO for 15 years—five of which were when the company had gone public.
$800,000,000
Yext market cap.
Throughout his tenure, Yext was three times named one of Fortune’s Best Places to Work, hired its 1,200th employee, and after ten years in business, notched $89 million in revenue. Only after he handed off the reins to his board chairman did Lerman move into a new category of virtual office work and launch Roam.
The idea for Roam was born of Lerman’s experiences at Yext, which, as he tells it, began with “five people in a room, then we were 50, and suddenly we were 1,500 around the world.” As the team swelled, the productivity and culture from the early days began to falter. “When we got big, my calendar became jammed up with back-to-back Zooms all day,” Lerman said. The issue led the entrepreneurial-minded leader to Roam, which he defines as “an office inside a computer.”
Here’s how Lerman lives his Good Life.
The finances
Fortune: What’s been the best investment you’ve ever bought?
Yext stock at $0.01, founding par shares.
Roam stock at $0.01, founding par shares.
And the worst?
The vast majority of my angel investments have returned nothing.
What are your living arrangements like: Swanky apartment in the city or suburban sprawling?
Miami Beach in Florida.
How do you commute to work?
People working for a Company of Tomorrow (in a Roam Virtual Office) can teleport in from anywhere. There’s no commute.
Do you carry a wallet?
I have a Flex credit card.
What personal finance advice would you give your 20-year-old self?
It is riskier to hold cash than stocks.
What’s the one subscription you can’t live without?
I buy books constantly, I try to read 30 minutes a day.
Where’s your go-to wristwatch from?
I’d lose a watch in a day.
The necessities
How do you get your daily coffee fix?
I have a Nespresso machine at home, one at my office and drink 4-5 per day. If a hotel doesn’t have a Nespresso machine in the room—I’m pissed.
What about eating on the go?
I don’t like to eat during the day. I never eat breakfast and very often skip lunch. If I do eat lunch, it’s usually at 2-3 pm and always protein, like a piece of fish.
Where do you buy groceries?
Trader Joes, Whole Foods, and Publix.
How often in a week do you dine out versus cook at home?
5x at home per week
Where do you shop for your work wardrobe?
My wardrobe is a system:
- 100 Black Turtlenecks from Lands End
- 25 pairs of black slacks from John Varvatos
- 10 pairs of Onrunning Cloud Monsters
- Gymshark Shorts & Pants
- Louboutin Boots
- Tom Ford Leather Jacket (the same as Jensen, incidentally!)
I’ve had this precise system for 15 years. It makes travel a snap.
The treats
Are you the proud owner of any futuristic gadgets?
My Apple Vision Pro have been relegated to “the drawer”.
How do you unwind from the top job?
Everyday I try to do something for my mind and something for my body before starting work. When I was running Yext, this manifested in a daily Mandarin Chinese lesson. Chinese requires exceptional focus. So if I could make it through that, everything else throughout the day was downstream. Now running Roam, I read something challenging upon waking. Think textbook level physics or neurology. After that, I train for an hour at my favorite gym.
What’s the best bonus treat you’ve bought yourself?
I bought myself a Rolls Royce convertible for my 40th birthday. I love EVs and believe in the future of energy but the styling and detailing on this toy are unsurpassed. Plus Tesla doesn’t have a convertible yet, so I suppose my hands were tied.
Take us on holiday with you, what’s next on your vacation list?
When I was running Yext, my idea of a vacation was Tuesday in a conference room at the Palo Alto Four Seasons. I traveled all the time but never took a vacation. I had some catching up to do, so when I founded Roam I promised my wife we’d do family trips to Europe each summer. It’s been fun to explore Italy, Greece, Scotland, France etc.
Here at The Good Life you don’t have to imagine what life at the top looks like anymore: Get real-life inspiration for how the most successful live life.
Fortune wants to hear from European leaders on what their “Good Life” looks like. Get in touch: orianna.royle@fortune.com
