What actually breaks businesses when markets change? In this episode of the Turning Pro Podcast, Ben Sharf sits down with Roman Khan, founder of Peak21, for one of the most practical and in-depth conversations we’ve had on operating and scaling businesses through volatility. Roman shares the hard-earned lessons that reshaped how he thinks about growth, cash flow, and discipline, including the mistakes that nearly cost him a business.

Jason Levin is the founder of MemeLord.com, the meme marketing software that’s turning internet jokes into serious business.

Jason’s been making memes since middle school, but what started as a way to make friends laugh has evolved into a multi-million-dollar media and software empire. From ghostwriting viral posts for founders to running brand accounts for Fortune 500s, Jason has built a playbook for using humor as a growth engine.

In this episode, Jason shares how he turned silliness into a career, why “cringe” is actually a moat, and the power of showing up online as your unfiltered self. He breaks down the real economics of the meme business, the tools that give him a competitive edge, and why most brands completely miss the mark when trying to be funny.

JT Barnett is the founder and CEO of Creator X, the content agency helping brands think like creators and act like media companies.

JT’s path is anything but traditional. He started out as a professional hockey player, then pivoted into content, building viral platforms like Honey House and helping breakout brands like Poppi win on social by going all in on community and authenticity.

In this episode, JT shares why most brands fail at content, how to actually build emotional connection at scale, and why the future of marketing will be led by creators who deeply understand their audience. He also opens up about quitting hockey with zero dollars, building from scratch, and the exact playbook his wife used to grow her wellness company, Form, into a community-powered rocket ship.

London Glorfield is the co-founder and CEO of Kickback, the cult-favorite consumer tech brand designing retro-inspired products that help Gen Z unplug from their phones and reclaim their time.

London’s story is wild. He started out in the music industry as a teenager, signed with RCA Records at 17, and built a fanbase touring across Asia. After stepping away from music, he turned his focus to building companies that blend creativity with cultural insight.

In this episode, London opens up about what it really takes to build something meaningful in a noisy world. He shares how a 145 percent tariff hike nearly broke the company, why most people misunderstand creative discipline, and how Kickback is building the anti-iPhone for a generation craving real connection.

Katie Hunt is the co-founder and CEO of Oh Norman!, the wellness brand redefining pet care and built from scratch with actress and animal activist Kaley Cuoco.

Katie’s story is anything but linear. She went from being an extra on Gossip Girl and answering customer calls at Warby Parker to co-founding Everywhere Ventures and relaunching Hinge from the ground up. But after the pandemic forced her to move home at 36, she started over this time building a company on her own terms.

In this episode, Katie opens up about what it really takes to build a business sustainably. She shares the burnout that broke her, the lessons she brought from Warby and Hinge, and why her all-women team runs a multimillion dollar brand without a single Slack channel.

Tom Shea is the founder and CEO of Adgile, the company turning last-mile delivery trucks into mobile billboards and proving real ROI for every brand on the road.

Five years ago, Tom was ready to walk away. The company had burned $1.8 million, his Series A deal collapsed at the finish line, and his co-founders left. But instead of giving up, he stayed in the game and quietly turned Adgile into one of the most exciting businesses in out-of-home advertising.

In this episode, Tom breaks down how he built a profitable, scalable company by thinking differently about physical space. He explains how their attribution tech works, shares the early moments that almost killed the business, and opens up about walking away from a $7 million deal to stay independent.

Chad Cohen is the founder of Fortem Media, a creative agency helping brands land at the center of culture, and the co-founder of Unofficial Run Club, one of the fastest-growing running communities in the world.

Two years ago, Chad hit a wall. Burnt out and mentally exhausted, he turned to therapy and was given a challenge that would change everything: run the New York City Marathon.

Since then, he’s built a thriving agency, scaled a global community, and brought on a full-time videographer to document every step.

In this episode, Chad opens up about how movement helped rebuild his mindset. He talks about the highs and lows of agency life, building a personal brand with intention, learning to manage a team while always on the move, and why he doesn't believe in turning pro.

Sydney Karmes-Wainer is the founder of French Squirrel, a cult-favorite snack brand built on hormone health, gut-friendly ingredients, and showing up authentically both online and off.

She started by posting recipes on Instagram. Five years later, she’s running a fast-growing CPG company, educating her audience on wellness, and selling out her products at launch.

In this episode, Sydney gets candid about what it actually takes to build in public. She opens up about pricing psychology, walking away from conventional advice, the loneliness of solo entrepreneurship, and how one conversation with Andrew Huberman reminded her she’s on the right path.

Chris Hladczuk is the co-founder and CEO of Hanover Park, an AI-native fund admin helping top venture firms run smarter and faster.

Before starting Hanover, Chris scaled Meow to $1.5 billion in assets as Chief Revenue Officer, built a strong online audience, and learned how to win through founder-led sales.

In this episode, he shares his full playbook. He breaks down how to pitch high-trust clients, what it takes to build a sticky product in fintech, why SaaS is losing its edge, and how he closed a $25 million deal after 26 follow-ups.

This is a conversation about selling with obsession, building with urgency, and staying relentless in a crowded market.

At just 16, Shirah Benarde had a dream that sparked one of the most innovative drink safety products on the market: NightCap.

Fast forward to today, and she's a Shark Tank alum, public speaker, and Gen Z founder making legislative change in California and beyond. In this episode, Shirah joins us to talk through everything: dropping out of college, navigating imposter syndrome, leading a company while still figuring it all out herself, and passing a bill to mandate drink covers in every California bar.

This is a story about building from scratch, trusting your gut, and staying grounded when the mission gets bigger than you.