Going Deep with Aaron Watson · Aaron Watson

260 Anthony Vennare, Building a Fitness Media & Technology Company the Right Way

April 10, 2025·35 min·3 clips

Anthony Vennare built a fitness media company that just raised $1 million, starting from door-to-door gym promotions in Pittsburgh.

The premise is blunt. Unlike law, medicine, or teaching, building a business does not come with a fixed credential path, so Anthony talks about entrepreneurship as something learned by doing, but not by betting the whole house every time. Aaron sets it up with patience. Fit starts as a Pittsburgh-based content platform aimed at helping people find fitness experiences and events, with plans to move into major U.S. cities and then cities abroad. The local read is the best part. Anthony saw Pittsburgh's food culture, chefs, farm dinners, and discovery habits, and noticed fitness moving toward that same lifestyle slot. The comparison lands because people already used Thrillist, Eater, and Yelp to decide where to eat or go out. Fitness, in his view, needed its own way to surface gyms, events, farmers markets, and juice bars. December 2015 is the hinge. Anthony describes spotting the opening, launching around health and fitness in Pittsburgh, and then checking the market instead of waiting for certainty to arrive. UPMC signed on as an advertiser, races paid, shirts sold, and the audience gave the company real feedback. Aaron keeps pulling the conversation back to mechanics. Growth is not treated like a miracle. It comes from timing, local knowledge, brand work, and a stomach for risk. Anthony is clear about failure, too. He failed many times, but tried to avoid risks that would knock him out completely, which makes his version of risk sound measured rather than romantic. The Joe contrast helps. Anthony is the action side; Joe brings planning. Together, they give the business a bit of speed and a bit of structure. The end gets personal without drifting too far. Anthony talks about visualization, writing down goals, keeping them visible, and choosing one concrete monthly move when bills and responsibilities limit daily progress. Even the Big Shaq detour fits, with a vision-board story about turning a written aim into proof you can point at.

As heard by us

A patient founder interview about turning fitness discovery into something people can actually use.

Aaron Watson and Anthony make the episode work by treating fitness like a real discovery problem, not a slogan. The conversation lands best when it compares the business to how people already look for food and events; that makes the company feel rooted in culture, not just…

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Why you'd press play

How Fit borrows the logic of Yelp and Eater to help people find fitness experiences.

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