Rich Swier was 20 years old and about to leave Florida for the West Coast when his parents' worry about staying in touch pushed him toward an unlikely business. With no real internet access available in the Sarasota area in 1994, Swier built his own dial-up internet service provider so his family could email him, and word spread through his father's veterans meetings until the business exploded overnight into thousands of customers. Within about eighteen months, Comcast bought the company, less for its customer base than for the provisioning software Swier had written, in a deal he says paid out eight figures and funded a house on Siesta Key's famously nicknamed Cocaine Row.
Swier stayed on through a three-year earnout at what became Comcast At Home, doing everything he could think of to get fired, including showing up to the office in shorts and golf clothes, before quitting to chase the next idea. What followed was a run of ventures that ranged from a short-lived attempt at building an offshore sports betting platform in Costa Rica, derailed after a funder demanded a cut for organized crime, to a website he built and sold within six weeks for half a million dollars under the alias Pete Salansky, hosted, he admits now, on leftover Comcast servers as a parting shot at his old employer.
From the Hub to Postgame Back in Sarasota for good, Swier founded the Hub, an early coworking space and incubator in the Rosemary District, out of which came Offers.com, a predictive-analytics real estate data company he eventually sold to Constellation Software, and Postgame, an app connecting college athletes to brands like Adidas and Crocs under Name, Image and Likeness rules, built with his college friend Bill a year before the legislation passed. He also traces Sarasota's Pineapple Drop back to his earlier New Year's Eve music festival, Vinyl, describing how he pitched local restaurants on hiring DJs and eventually took over marketing for the downtown celebration when the city could no longer fund it.
Swier is candid that his newest venture, an AI platform he calls Rehea, has taken nearly a decade longer than expected to catch up to the technology, a pattern he says defines real entrepreneurship: being years ahead of what the market is ready to buy. The hosts put him through an unusually loose Rapid Fire Gauntlet, in which Swier picks flying as a childhood ambition he'd trade for being a shepherd and names Mini Wheats over Frosted Flakes, before the show closes out with its usual roundabout check-in on how Sarasota's growth looks to a lifelong local who has watched the city evolve since before its tech scene existed.
What you'll take away
- Swier built one of Sarasota's first internet service providers at age 20 and sold it to Comcast within about eighteen months for an eight-figure deal
- He later built and sold a search-engine business in six weeks under an alias, hosted ironically on leftover Comcast servers
- His coworking space, the Hub, incubated Offers.com, later sold to Constellation Software, and Postgame, an NIL platform working with brands including Adidas and Crocs
- Swier traces the roots of Sarasota's Pineapple Drop to a music festival he founded called Vinyl
- He describes his AI venture, Rehea, as roughly a decade ahead of the market when he first started building it
“I like to think that I invented work from home.”
“You have to continue to change, and the more rapid you change and the more flexible you are, the more successful you'll be.”
Places mentioned: Siesta Key, Rosemary District, Fruitville