Inside Medium Rare's Celebrity Events Business | Entrepreneur

The first time I spoke with Adam Richman and Joe Silberzweig, the co-founders of live events company Medium Rare, they were figuring out how their business could survive in a world shut down by the pandemic.

In the five years that followed, they did more than just figure it out — they absolutely blew up. Medium Rare has become a powerhouse in the events space, creating festivals for some of the biggest names in sports and entertainment: Rob Gronkowski‘s Gronk Beach, Travis Kelce‘s Kelce Jam, Shaquille O’Neal‘s Shaq’s Fun House and Guy Fieri‘s Flavortown Tailgate, to name a few.

I caught up with them as they were firing up the ovens for Dave Portnoy‘s One Bite Pizza Festival and prepping for John Summit’s upcoming Experts Only dance music festival (to be held September 20-21 on New York City’s Randall’s Island).

The duo shared their insights and tips for building, growing and problem-solving that any entrepreneur looking to build momentum and scale can apply to their service-based business.

Momentum breeds momentum

When Richman and Silberzweig first launched Medium Rare just before the Covid-19 pandemic, “no one gave a crap about us,” Richman recalls. “No one would take our call.” But after landing their first big celebrity collaborations, everything changed. “It is a domino effect — each event serves as its own sort of engine to the next one,” Richman explains. “The visibility of working with Shaq led to deals with Guy Fieri, who attended a previous event, which then led to Travis Kelce, and so on.” The guys treat every festival and event as an advertisement for what they can do.

Takeaway: Make your work your marketing. Focus on delivering standout results for current clients, and let word-of-mouth build curiosity and opportunity for future partnerships.

Be strategic, not desperate

Richman and Silberzweig have learned not to say “yes” to every opportunity. “We’ve had MVP-caliber athletes reach out to us, but Adam and I just kind of banged our heads against the wall and couldn’t figure out anything for this guy that we absolutely loved,” Silberzweig says. They turned down the offer, which shocked the athlete’s rep. “They said, ‘You’re the first person who has ever said no to us!'” he recalls.

The pair says that in the early days, they would have jumped at the chance, but time and experience taught them not to force it. “There are only so many weeks in the year to plan these events, so we’ve learned to be a little bit more selective and strategic about throwing our energy into the ones we can really elevate,” Silberzweig says.

Takeaway: Protect your time, energy and brand by learning to say “no.” Select partners and projects that align with your values and inspire you to do great work.

Credit: Medium Rare

Creative problem-solving under pressure

Executing Portnoy’s One Bite Pizza Festival had enormous logistical challenges. “Everyone told us we were crazy. All of our peers in the industry were like, ‘There’s no way you can do a pizza festival,'” Richman recalls.

Each participating pizzeria required its own specialized oven — none of which could be rented in quantity. Their solution? “We bought the ovens from restaurant supply companies new, we’ll use them for seven hours, then sell them back as used. It’s a creative rental,” Richman explains. The initial outlay topped $1 million, but they calculate that they’ll recover about 70% through equipment resale.

Takeaway: Take “impossible” as a challenge, not a verdict. Keep pushing for creative solutions — sometimes this means reimagining industry norms or business models, or laying out capital to take a calculated risk.

Stay cool — and collaborative — when chaos hits

The founders say what separates top live event producers from the rest is “how they deal with the curveballs.” Whether it’s a lightning storm, missed flights or city permits, they emphasize splitting duties and making fast, collective decisions: “We know how to put our thinking caps on and react in those situations,” Richman says.

When Jalen Brunson and Josh Hart‘s Roommates Fest event was threatened by storms, they “got on our hands and knees” with city officials to negotiate a later start time. After securing that, they rewrote the run-of-show, coordinated with celebrity guests and informed attendees — all in under 30 minutes.

Takeaway: Build a culture of problem-solving. Success depends not just on planning but also on reacting to the unexpected with focus and clear communication.