Gerry Powell’s Second Act Still Has a Business Plan.

A satellite-dish business is an unglamorous place to begin a story about purpose. It has customers, equipment and the stubborn requirement that the thing on the roof should work. Gerry Powell tried that business early in his career. It failed. He tried telemarketing next, sold the company, and took a job in Australia. Long before Costa Rica, before the books and the speaking engagements, there was a young salesman discovering that a fresh start could be an ordinary business decision.

The contrast matters because Powell’s later life is often presented as a dramatic departure. The founder and CEO of Rythmia now talks about truth, service and becoming useful to other people. His earlier vocabulary included sales, property and company valuations. But follow the work itself and a familiar character keeps appearing: someone who finds an idea, figures out how to sell it, and tries to build an organization around it.

Powell has changed what he wants that organization to accomplish. He has kept a surprising amount of the machinery. Even a second act needs somebody to look at the bills.

Before Costa Rica, there was the telephone

Gerard Armond Powell was born in Scranton, Pennsylvania. His early working life ran through the vacation-home market in the Poconos, where he sold timeshares. His education was interrupted: he was expelled from one school and left another before graduating. Direct sales became the place where he learned to work.

It was an education with unusually prompt grading. A customer either bought or did not. A pitch either survived a conversation or disappeared somewhere between the greeting and the goodbye. There were no academic honors to wait for, only the next prospect. The practical appeal of that arrangement is easy to understand for someone already outside the usual school-to-career procession.

His 1987 telemarketing venture took him from Philadelphia to a position at Capri Waters Club in Melbourne, Australia. He returned to the United States in 1990 after his work visa expired. The itinerary gives his early biography a restless quality: Pennsylvania, a telephone business, Australia, then home again. Opportunity supplied the route; immigration paperwork supplied the return ticket.

In 1991 he founded Y-Rent, a development business built around helping renters become homeowners. Later came ThatLook.com and a turn toward the internet economy. The underlying commercial interest remained recognizable. Powell was working on the distance between something people wanted and the arrangements that would let them buy it.

There is a salesman’s continuity here. Changing industries does not necessarily mean beginning from zero. The customer changes, the purchase changes, the brochure gets redesigned. The questions about demand, access and persuasion can follow an entrepreneur from one venture to the next.

A fortune with a follow-up question

Going public did not settle Powell’s career. The technology-market collapse disrupted ThatLook.com, and he lost his position as chief executive in 2001. He and his former management team started again. The sequence is less tidy than the familiar entrepreneur’s ascent: build, float, lose control, rebuild. The upward arrow had acquired a few inconvenient bends.

Powell says he became a millionaire in his twenties and bought his first airplane in his thirties. Those are the details that make a business biography easy to picture. An aircraft is a wonderfully legible achievement. Nobody needs a footnote explaining that its owner has acquired options.

His own account of business success, however, has become increasingly concerned with what follows the acquisition of those options. In a 2023 conversation, he described two substantial deals, one in his thirties and another in his forties. He also described a conviction that persistence and continuing to create value matter more than waiting for luck.

That sounds like a founder still willing to make a case for work. Powell has not turned his later career into a campaign against enterprise. His question is what enterprise is supposed to deliver, and what a person does after the conventional rewards have arrived.

The distinction gives his story some friction. Advice about money can be rather comfortable when delivered by someone who has already made it. Powell brings that complication with him. His perspective comes from having pursued financial success, encountered reversals, and returned to the business of building. The question of value follows him into the next venture.

A retreat still needs a balance sheet

Rythmia opened in 2016 in Guanacaste, on Costa Rica’s Pacific side. Powell and co-founder Jeff McNairy had searched the country for a property before buying in Hacienda Pinilla. The result was a destination business with accommodation, meals, classes and a weeklong schedule. Whatever else a guest hoped to find there, somebody still had to prepare the room.

Powell has described the all-inclusive approach in terms of Club Med. It is a revealing comparison. A familiar hospitality format makes a complicated trip easier to understand: travel to one place, stay there, follow a program, have the practical arrangements bundled together. The proposition is organized around a stay rather than a collection of separate purchases.

Behind that familiar format lay a less comfortable funding problem. In an early interview, Powell said his initial expectation of investing a couple of million dollars had turned into $11 million of his own money. At that stage, the business needed continued support from its founder. An expansive mission had produced a very specific cash requirement.

“This is the single point of failure thing.”

Gerry Powell, discussing the venture’s early dependence on his funding

The phrase is an unusually practical admission in a story about reinvention. Powell wanted the operation to become financially viable so it could outlast his willingness, or ability, to keep contributing money. His ambition included a model other businesspeople could adopt. He imagined competition bringing more choice and lower prices.

That remains an aspiration rather than a map of an existing chain. Rythmia’s current description identifies one location in Costa Rica. The interesting part of Powell’s early argument is the problem he recognized: a founder’s personal commitment can launch an organization, while also becoming its most fragile dependency. He was asking how to move beyond that arrangement.

A boardroom with an unusual guest list

The people around Powell make another part of the story visible. Rythmia’s board includes figures from business, sport, entertainment and spiritual teaching. The current roster names surfer Kelly Slater, NYX Cosmetics founder Toni Ko, author Jack Canfield and Michael Bernard Beckwith, among others.

Cesar Millan’s appointment was announced in September 2022. Comedian Ron White joined in December 2023. Their presence makes for a board list that reads less like a single industry’s directory than several dinner parties accidentally given the same reservation.

The appointments are concrete connections, with different careers attached. They do not, on their own, tell us how decisions are made inside the company. They do show the breadth of the public circle Powell has assembled around a destination in Costa Rica. A business with an international audience has drawn supporters whose audiences extend well beyond hospitality.

Powell’s own public manner fits that mixture. He can move between commercial detail and spiritual vocabulary without making much of the crossing. His interviews are blunt, sometimes profane, and frequently self-critical. The executive who discusses viability is also willing to question the ambitions that made him an executive in the first place.

Putting honesty on the balance sheet

In 2022 Powell published Truthenomics: The Science of Allowing Abundance Through Honesty. The title joins two subjects that usually occupy different shelves: the pursuit of money and the difficulty of telling oneself the truth. At 112 pages, the paperback makes its case without demanding that the reader clear an entire season.

The book’s premise connects personal truth with personal finance. It asks readers to consider what they want and why, alongside their efforts to accumulate wealth. That is a natural extension of Powell’s public story. He has spent years describing the distance between a financially successful life and one whose purpose he could explain to himself.

Writing also changes the terms of that conversation. A founder speaking at his own destination has an audience gathered around him. A book has to travel without its author. The argument must survive an ordinary afternoon, a distracted reader and the absence of a tropical setting. Ideas acquire a different sort of independence when somebody can close the cover.

Powell’s videos offer another format for the same continuing discussion. In his 2023 The Road Less Taken series, he emphasized becoming a “beneficial presence.” It is a modest phrase beside the language of valuations and exits. Its unit of account is what other people receive from having you around.

The builder is still at work

MoonWorks, founded in 2023, carries Powell’s business activity into an investment and holding-company structure. He is identified as its founder and CEO. Its stated activities include destination experiences, residential development in Guanacaste, and a travel sales and digital marketing agency. Property, sales and promotion have returned to the picture, now gathered around his later interests.

The structure makes his continuity especially clear. A founder who began with direct selling is still concerned with reaching customers. Someone who worked in development is again involved with property. The geographical setting and the purpose have changed; the available tools look familiar. Reinvention has given those skills another set of uses.

Powell continued discussing participation and service in a public interview in June 2026. These are recurring themes rather than a finished declaration. They leave him with an assignment that cannot be completed by a transaction alone. Selling a business can establish a date and a price. Being useful requires another day of doing something useful.

His second act is therefore still full of work: a destination to operate, organizations to build, ideas to put into words. The young salesman once moved across the world for a job. The older founder has made a place people travel to. Between those journeys, Powell has kept asking what he can build. He now spends rather more time asking what it is for.