Unlike Me

Today’s guest is Jaclyn Johnson, a serial entrepreneur, investor, and the founder of Cherub, a new platform reimagining how early-stage founders and investors connect. Before Cherub, Jaclyn built and exited Create & Cultivate, leading her to over $25M of exits and cementing her as one of the most influential builders in modern women’s business culture.In this conversation, we get into the real stuff behind the highlight reel, from navigating divorce and dating in the middle of a very public career, to the unsexy realities of selling a company, starting again, and figuring out what you really want your life to look like on the other side. We also talk about how she thinks about modern entrepreneurship, where the creator and founder worlds are colliding, and why building a brand that actually means something has never been more important.

In this episode, I sit down with Mallory Edens, founder of Little Ray Media, a production company focused on elevating stories by and about women in film and television. We discuss her passion for reshaping which stories get told in Hollywood and who gets to tell them. Mallory also opens up about a traumatic accident that changed her trajectory and strengthened her resilience and clarity of purpose. We talk about coming from an NBA family, acknowledging the privilege that comes with that, while still intentionally carving out her own lane and building something that is distinctly hers.

In this episode, I sit down with Josh Cohen, CEO of Pinpoint - one of my portfolio companies that just raised a $2.5 million seed round from top investors, as well as KSI with his Sidemen Fund. We talk about how Pinpoint is helping brands convert their social audiences into paying customers and why I think it’s one of the most underrated tools out there right now. Josh and I dive into what efficient growth looks like in today’s digital-first world and how smart brands are simplifying their funnel to drive real results. If you’re a founder of an online brand, or just a lover of great businesses and sharp founders, this one’s for you.

In this solo episode, I sit down for an unfiltered Q&A from my work at the intersection of venture capital and the creator economy. I talk about what I’ve learned from building on my own, the importance of failing quickly, and how those failures have shaped the way I think about business, ownership, and growth. If you’re a founder, creator, or just curious about what it’s really like behind the scenes, this one’s for you.

In this episode, I sit down with Megan Lightcap, partner at Slow Ventures, which recently raised its $64 million creator fund to back creator-led businesses. While both Megan and I operate at the intersection of venture capital and the creator economy, we approach it from very different angles, which made for a dynamic and thought-provoking conversation. We unpack the structure of Slow Ventures, explore what ownership looks like in the digitally native age, and discuss the evolving relationship between creators and capital.

n this episode, I sit down with John Sutton, CEO and founder of Journey—a company rethinking loyalty from the ground up. We talk about why the traditional points-based model is outdated, and how Journey is introducing a smarter, more personalized system designed for independent and boutique hotels. John shares his path from helping scale Red Ventures into a digital powerhouse to now building a platform that gives hotels the tools to drive real guest loyalty—without relying on legacy tactics.We get into the psychology of what actually makes people come back, how personalization plays a role in the modern travel experience, and why Journey is building a network that puts both operators and guests first. Plus, we go deeper into John’s perspective as a founder, a builder, and a father—and what it really takes to challenge an industry as entrenched as hospitality.

In this episode I sit down with Sophia Kianni to discuss Phia, the comparison-shopping platform she’s building with her best friend, Phoebe Gates that helps Gen Z save money—think Google Flights for fashion. We dig into how she stays grounded despite nonstop media attention, the pressure of being in the spotlight, and her lifelong hustler mindset. Sophia also shares how she juggles dating while building the next $1B business.

Jeremiah Brown isn’t holding anything back. In this episode, he opens up about the friendships that fell apart after leaving the Villa, including whether things are really over with the boys who voted him out. He reflects on the intense relationship that defined his time in the villa, what he learned from it, and the connection that surprised him most. We also get into how he’s adjusting to life post-show and whether he’s truly done with reality TV.

In this episode, top recruiter and founder of her company the Linchpin Co., Colleen Pelly breaks down exactly what it takes to stand out in today’s competitive job market — from resume red flags to the subtle signals that make hiring managers say yes. We dive into the art of salary negotiation, why certain demographics consistently undersell themselves, and how to approach job searching with strategy and confidence. Colleen also shares the story of how she built and scaled her recruiting business from the ground up — all while on maternity leave.

Ashwinn Krishnaswamy is the co-founder of Oklahoma Smokes and Sunpowder, and one of the most thoughtful brand minds in the game. In this episode, we talk about what it actually takes to build a brand that lasts, why most early-stage founders waste money on paid ads, and how a run-in with the cops turned into a story worth telling.He breaks down why identity matters more than aesthetics, why performance marketing is often a trap, and how to build cultural relevance from day one. If you care about brand, distribution, or just want to hear how a wellness founder ended up in handcuffs, this one’s for you.