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.