John Andrew Entwistle’s father only learned that his 13-year-old son was running a six-figure video game server business when an unexpected email caught his eye. Entwistle had cc’d his dad—a New York-based attorney—on an email thread with several lawyers working for Microsoft. They were alleging that the teenaged entrepreneur had attempted to trademark a name already claimed by the tech giant—and were threatening a lawsuit.
“That's when [my dad] was, like, ‘Hey son, what exactly are you doing online?’” Entwistle recalls fourteen years later. After dealing with the trademark problem, his father asked if he had paid the company’s taxes.
Young John confessed that he hadn’t. “I remember going to the accountant in the city with him,” Entwistle says, “and I think I spent more in accounting fees than revenue I had—but it was all great lessons as a young founder.”
After launching a series of moderately successful tech companies (all based around Minecraft, his favorite game at the time), Entwistle decided to get serious about his future. At 18 he took a pass on college to found Coder in 2015, a cloud development startup that raised $85 million in capital from Peter Thiel’s Founders Fund and California-based Notable Capital. Coder made collaboration between engineers easier and more productive by moving workflow from a local computer to the cloud—effectively creating Google Docs for coders. The company landed Entwistle and his cofounders on Forbes’ 30 Under 30 list in 2020.
But just a year later, Entwistle made an unexpected turn. He left Coder to found Austin-based Wander, a short-term luxury rental startup aimed at guaranteeing perfect vacation experiences using automation. Entwistle secured about $100 million in venture funding from firms such as Redpoint Ventures and QED Investors and four years after its founding, Wander is projected to bring in some $70 million in gross sales this year.
As with all rental companies, clients can find homes on Wander, ranging from a $370-per-night mountain-view condo in Winter Park, Colorado, to a decadent mansion in South Lake Tahoe, California for $3,600 a night. Taking advantage of consumers’ steady demand for luxury travel, Wander has impressed investors with its AI-powered software that grants the company complete control over every facet of home rental, from security to pest control. Unlike on Airbnb, Wander has a store where hosts can procure items like smart locks to make the property compatible with the company’s software (about 40% of Wander homes use this service, other properties tend to already have compatible vendors and equipment). Wander charges an 8 to 12% host fee—by comparison, Airbnb has a 15.5% host fee—and its gross margins are between 70 to 80%. Wander attributes this to the fact that none of their properties go unused or waste money: “If we had a bunch of bad units with this type of more intensive involved structure, then our margins wouldn't be as good as they are,” Entwistle says.
Wander closed on a $50 million Series B round last May, capitalizing on the boom in luxury travel. Spending in the category has increased globally from $4.2 billion in 2019 to $5.2 billion in 2024, according to Boston Consulting Group. The industry has always been supported by a reliable base of rich folks willing to spend on leisure travel. But Mike Gallinari, a travel analyst for London-based research firm Mintel, says more middle-class travelers are now choosing to spend on higher-end stays: “We’ve seen that a lot of people are willing to say, ‘Well, I want to have a better, fancier, more bragworthy experience.’”
And in an economy rife with instability, it’s becoming risky for venture capital firms to fund businesses producing manufactured goods that might be affected by volatile tariffs. One solution? Experience-based companies, which are “more indirectly affected by tariffs than consumer packaged goods or any of these other sectors,” says Gallinari.
Some of Wander’s much larger competitors point the way—Airbnb’s revenue grew 11% from $9.9 billion in 2023 to more than $11 billion in 2024. Booking.com is also booming, growing 12% from $21.4 billion to almost $24 billion over the same time.
Entwistle believes the industry’s durability is simple. “If you look at travel historically, even in macroeconomic depressions, it’s stayed relatively strong because people want to get away during those times,” he says. “You're looking at an industry that is a part of human nature.”
Travel is certainly a significant part of Entwistle’s nature. Raised by a single dad in Bedford, New York, he developed an interest in software after watching his father work from home at the computer.
School was more of distraction than anything else for Entwistle. He tested out of middle school and despite getting several full scholarships to private high school, he convinced his father to let him finish his education online.
“I ultimately just wanted to build stuff online and not go to school,” Entwistle says. “I put together this big pitch deck [for my dad] on the wasted time that I might have throughout the day by going to class or homeroom—and he ended up accepting it.”
Entwistle joined his father on business trips around the world, eventually leading to a stint at the Bondurant Racing School in Arizona. At 16, he ended up Formula racing in open-level categories for teams in Texas and Indiana and once finished second at a Formula Mazda National Championship in 2016.
“I always thought that I was going to run businesses, but I was just having so much fun,” he says. “I knew I wasn't going to become a professional race car driver—I was good, but I wasn’t great.”
Entwistle hit the brakes on racing in 2017 when, at 18, he broke his back in a car crash at the Indianapolis Motor Speedway. During his recovery, he spent time working Coder with fellow tech whiz kids Ammar Bandukwala and Kyle Carberry—who had worked with Entwistle to build Minecraft servers when they were all still teenagers. The trio moved to Austin soon after to start the business.
“I still had my back brace on from my accident while we were putting together the desk setups and hiding our age when we were interviewing employees,” Entwistle says. “It was the Forbes Under 30 article that spotlighted that we were like 22, and our people were, like, ‘Wait, you're not 35?’”
While Entwistle was CEO, he received a Thiel Fellowship, awarded to promising young entrepreneurs who forego college, and raised an additional $50 million. Coder, now worth more than an estimated $200 million, powers more than a million software engineers at companies such as Vanguard, Goldman Sachs, Palantir and Netflix. Entwistle ran Coder until he was 23, through the company’s Series B funding round.
“At that point I'd been running the company for five-plus years and felt it was time to move on and do something else,” he says.
Entwistle says his stake, spilt equally among his cofounders and diluted after raising capital, was worth more than $10 million when he stepped down from Coder.
He knew he was going to start another company, but he didn’t have any direction. “So, I rented this cabin in Colorado to get away and think about the world—sort of an early-twenties midlife crisis,” he jokes. “When I got there, it was just a classic bad Airbnb experience. The place didn't look like the photos, the beds weren't comfortable, and the heat didn't work. But I was happy because I was just trying to get away and to think.”
That’s when the idea for Wander came to him. His guiding question was inspired by the decade he had spent optimizing software for other people: “Could you create the operating system for the hosts to better run their properties and services?”
Investors from Coder were keen to work with him again, although several were skeptical of funding his new travel-based venture. “I had a lot of VCs reaching out to me offering $10 and $15 million investments in any type of B2B software idea,” he says. “But I wanted to build a company I could build for the rest of my life and that would bring happiness to people rather than slightly improve the KPIs of some B2B company.”
Entwistle launched Wander in 2021. RedPoint Ventures—which led Coder’s Series A—ended up leading Wander’s pre-seed and Series A round, which totaled nearly $30 million. After nine months, the startup had just five homes in its portfolio, including properties in Lake Tahoe and Joshua Tree. Still, Wander raised another $20 million and surpassed 30,000 users on its waitlist.
Wander took in around $4 million in gross revenue in its first full year, increasing to about $8 million by the next year. By 2024, it had surpassed 1,000 properties across the United States and had about $25 million in gross sales.
With more than 2,000 homes in is roster now, Wander is microscopic compared to Airbnb (8 million listings) or VRBO (2 million). While Entwistle is focused on scaling up, there is a methodology to adding new properties. Wander’s operating system starts by sifting through millions of listings and analyzing factors like safety data and satellite imagery of homes with the help of AI. Then it screens the host or property manager before that home becomes a listing. Once it’s a part of Wander’s network, the software manages every detail of property management for the host and guest.
“I want know exactly what each home is doing from a performance perspective, and then I want the system to automatically flag anything to me on a per-home basis,” Entwistle says. “On Airbnb, that level of integration just doesn't exist.”
The alternative is measuring guest experiences in a portfolio-wide basis like Airbnb. “That’s when you get a lot of things that cover up bad experiences,” Entwistle says.
Part of Airbnb’s genius, of course, is that it puts the onus of hospitality on the host. But that has also been the bane of Airbnb’s reputation. The traditional way to prevent horror-story rental experiences is classic hospitality: a concierge service, for instance. Other luxury rental platforms, such as OneFineStay, which is owned the French hospitality chain Accor, achieve more consistently good guest experiences this way.
Wander will also expand globally this year and is targeting 10,000 locations by the end of 2026. Entwistle, who is the largest individual shareholder, with 20% of the company says he’s ready for the challenge of translating his business into new cultures.
As for Entwistle, he now lives in a light-filled apartment in Sausalito, California—about 10 miles away from the nearest Wander rental. And though is home is not available on the platform, he can’t help but be a gracious host, gesturing past tasteful white furniture toward his ivy-filled balcony with a perfect view of the Golden Gate Bridge.