Down to Business

As the founder and CEO of multiple successful Internet ventures, Jesse Stein proves he knows a thing or two about business…just don’t expect him to follow all the rules!
Text by Luisana Suegart Photos by jose amigo | July 10, 2018 | People

Internet entrepreneur Jesse J. Stein has dreamed of building businesses for as long as he can remember. At 39, the Northern California native and current Key Biscayne resident is the co-founder and operator of a range of Web-based businesses, while sitting on creative experience that dates back to his early elementary school days.
“I knew early on I wanted to go into business. My grandfather, Yudy, was a self-made entrepreneur and my personal hero,” he says. “Trying to assume his persona, I carried around a little briefcase when I was 6 years old.”
Consequently, a 10-year-old Stein started collecting tips for serving drinks to party guests, and began cold-calling for stockbrokers at 15, all the while selling luggage and dreaming about someday going to The Wharton School. But before his dreams of Wharton materialized, Stein earned a degree in Asian Studies and Sociology from the UC Santa Barbara and Tokyo’s Sophia University.
“Right after graduating from college, I spent five more years living in Tokyo,” says Stein, who took up a job in door-to-door sales speaking Japanese. He was one of only nine foreigners in a company of 2,000. “Nothing could prepare me for the morning chorei, in which the entire office lined up and shouted corporate slogans while bowing repeatedly,” he laughs. “I was a fish out of water!”
For the next four years, Stein took up a Tokyo-based financial journalist position, while having fun on the side co-authoring The Tokyo Nightlife Guide.
Hoping for a soft landing back to the U.S., Stein decided to apply to MBA schools. “The Wharton Admissions Director must have been drunk the day he read my application, because miraculously I was accepted,” he laughs.
Though he wouldn’t trade his years at Wharton for anything in the world, Stein says the experience taught him what not to do in business. “The school taught us to be perfectionists — to perform mountains of analysis before making a business decision of any consequence,” he admits. “Fresh out of Wharton, I naively thought I’d take this ethic, combine it with theories and concepts from the classroom, and somehow take the business world by storm.”
In retrospect, he understands he couldn’t have been more wrong. His first real business, an online retailer of apparel, which he started with his two best friends, is what he calls a classic dot bomb, with too much time spent in “analysis paralysis” and too little time devoted to execution. “Trying to learn from this setback, I realized I was at my best when I ignored the business school obsession with precision.”
Meanwhile, he noticed that the entrepreneurs he admired most — from Andrew Carnegie to Richard Branson to his grandfather — were known for pulling the trigger quickly in the absence of perfect information. And so he pulled his own proverbial trigger and decided to live by a kind of mentality he best describes as, “Screw it — Just do it!”
“I found that in most areas, good is enough and making it perfect takes way too long. As a result, I began to seize opportunities faster, get more done in a day and strike gold more often.” Together with his partners, Paul and Wayne, Stein founded, grew and sold a Manhattan-based online advertising agency that was headquartered just two blocks from where his grandfather had worked for 50 years. “Indeed, even after my grandfather passed, it seems I remained magnetically drawn to him,” he says.
Since then, Stein and partner Paul have run several Internet companies. Their core business creates and markets — exclusively via the Internet — a range of health and beauty products. One of their other ventures,, is a leading online retailer of sports collectibles.
With their companies headquartered on Lincoln Road and with a warehouse in the Design District, Stein and his partner currently employ 55 people in Miami with 40 others scattered around Pennsylvania, India and the Philippines. “It might sound cliché, but none of what we achieve would be remotely possible without the incredible talent and effort of our team.”
How he landed on the Key, however, is a whole other story, though not surprisingly one that also involves the Internet. Three years ago, Stein and his wife Jimena posted a simple ad for a one-week apartment swap, and as luck would have it, a family living in the Ocean Club responded. “We realized this place was almost too good to be true: a bi-cultural, bi-lingual paradise filled with laid-back, interesting people — all within striking distance of a vibrant city,” says Stein. “Plus we had a backyard where we could swim, run, kiteboard — or just relax on the beach.” The end result: Stein & Co. — his wife and three children: Jack, 6; Alec, 3; and 2-month-old Diego — have officially put down their roots in Key Biscayne.
As he reflects on what he calls his good fortune, Stein says he is standing on the shoulders of giants, including his wonderful family, friends, colleagues and mentors. “I’m particularly grateful to my beautiful wife and children who make it all worth it,” he says. “And, of course, special thanks to Craigslist and the Campiani family who responded to our posting — without them, we wouldn’t be here!”