Jesse Schoberg began plotting his escape from Elkhorn, Wisconsin, where he was born and raised, when he was a teenager. "It's your typical small town in the Midwest: small, quiet, not too much adventure," he tells CNBC Make It. "I always knew that I wanted to get out and explore the world."
The 41-year-old entrepreneur has now been living abroad for 14 years, splitting his time among more than 40 countries — and he has no plans to return to the U.S. anytime soon.
Schoberg bucked the traditional path of attending college and securing a 9-to-5 job, instead choosing to move to Madison when he was 19, sharpening his coding skills and helping businesses with their website design and development.
By the time he turned 27, however, Schoberg began to feel restless. He decided to move to a new city and researched apartments in Austin and Denver, but his mind kept drifting to Panama City, the capital of Panama, where he had "one of the best vacations of his life," as he recalls.
He moved to Panama City in 2008 and lived there for six years before packing his bags to travel the world full time as a digital nomad, a movement he had learned about, and was inspired to try, during a work retreat in Curaçao.
In between his travels, Schoberg now calls Bangkok home. He relocated to Thailand in December 2021 and shares a one-bedroom apartment with his fiancée, Janine.
"The quality of life in Thailand compared to the United States, is much better for 90% of things and more stress-free," he says. "It's also a lot easier to afford a luxurious lifestyle."
Schoberg has built a formidable career as an entrepreneur and web developer, earning a six-figure salary each year — but his success didn't happen overnight.
When he first moved to Panama, Schoberg brought the web design and development firm he established in the U.S. — and his list of clients — with him.
In 2013, Schoberg and two of his friends who had worked with him on previous projects for the firm, Jason Mayfield and Laura Lee, created DropInBlog, a software start-up that helps website owners add an SEO-optimized blog to almost any platform in minutes.
Today, DropInBlog has an all-remote staff of 12 employees, with Schoberg at the helm as CEO.
Becoming his own boss gave Schoberg a more flexible schedule, and he used his newfound free time to travel: After visiting several countries in Central and South America, including Colombia and Costa Rica, he decided to check out Asia, living for short stints in Taiwan, Japan and the Philippines (where he met his fiancée on a Tinder date).
In 2015, Schoberg stopped in Thailand — and he immediately knew he found his new home. "When I got to Bangkok for the first time, it just had that pulse that felt familiar to Panama City … there's just this incredible energy on the street and with the people," he says. "I knew right away that Bangkok was going to be my Panama City 2.0."
Schoberg and his fiancée have been splitting their time between Mexico City and Bangkok as he waits for his Thai Elite Visa, a 5-year renewable visa that costs about $18,000 and gives you unlimited access to Thailand as well as entry and exit privileges.
Since moving to Bangkok, Schoberg has been able to spend more on travel, dining and other hobbies as well as boost his savings. "While I can afford a pretty nice life in the U.S., I live a lot better here than I did in the U.S.," he says. "The level of services that you get here — fancier movie theaters, nice cars — completely blow away what you get in the U.S."
As an entrepreneur and CEO, Schoberg earns about $230,000 per year. His biggest expenses are his rent and utilities, which together are about $2,710 each month. Schoberg and his fiancée live in a one-bedroom apartment in a building with a private gym, pool, co-working space, restaurant and daily cleaning service.
He and Janine spend about $1,900 each month on takeout and dining out, often ordering food from local restaurants on a popular app called Food Panda. Schoberg's go-to meals are khao soi, a coconut curry noodle soup with braised chicken, and pad krapow, a spicy basil chicken dish. Both meals usually cost $2-$3, Schoberg says, and local restaurants will often give long-term customers discounts.
The food scene, he says, is a "huge plus" to living in Thailand, and one of the main reasons he chose to move to Bangkok. "Bangkok has an amazing culinary scene, you have pretty much every type of food in the world here," Schoberg says. "Just around the corner from my apartment, there's a Belgian sandwich shop and a Korean barbeque joint."
Here's a monthly breakdown of Schoberg's spending (as of June 2022):
Rent and utilities: $2,709.52
Health insurance: $280.39
The Thai culture and people are "much friendlier and more relaxed" than in the U.S., Schoberg adds, and while English is spoken in the more popular tourist regions, like Bangkok, learning Thai has given Schoberg "a huge advantage" as a foreigner.
He attends two Thai classes per week, which costs $269.44 a month, and stresses that "you can really engage in the culture and have a better life" in Bangkok if you're able to understand Thai.
As a new resident, Schoberg is still exploring Bangkok and all that it has to offer, including its many malls, parks, restaurants and concert venues — one of the magical aspects of living in Bangkok, he adds, is that it can feel like you're living in two different cities at once.
"You've got the street-level city, which is your food vendors, people running to work, taxis and motorbikes," he says. "And then there's this sky city that's happening in the skyscrapers, with fancy rooftop bars, working spaces and malls … here, you have the contrast of the Chanel store to the 20-cent pork skewer being grilled on the street."
Schoberg is planning to live in Thailand for the foreseeable future, and keep Mexico City as his second home base as he and Janine continue to cross places off of their travel bucket list.
He doesn't see any reason to return to the U.S. "It's fascinating to learn about different cultures and have authentic foods around the world, as well as just interact with different people with different ideas" he says. "I enjoy those aspects of living abroad as well as a bit of the simplicity and lack of conflict that I'm seeing so often in the U.S."
Eventually, Schoberg's goal is to set up several home bases on different continents throughout the world — but he hasn't planned too far ahead.
"That's the beauty of exploring the earth, right? It could be Mexico, Europe and Dubai, who knows … but I like to keep my options open," he says.