Stephen Ellsworth, co-founder of Poppi, joins Due To My Role to break down what actually goes into building — and exiting — a modern consumer brand.

Poppi started as a scrappy apple-cider-vinegar drink sold at farmers markets, became a breakout Shark Tank success story, and ultimately sold to Pepsi for $1.95 billion. But the real story isn’t the TV moment — it’s the decade-long grind between launch and liquidity.

Stephen walks through the realities founders don’t post on LinkedIn: maxed-out credit cards, Medicaid coverage, payroll panic, and watching friends live comfortably while you bet everything on belief. He explains why the beverage category is one of the hardest in consumer, how branding only works when it carries founder DNA, and why distribution—not hype—is what finally breaks a brand open.

They dig into what life looks like after the exit: confidence earned (not imagined), choosing what to work on next, and why creative problem-solving is the real addiction founders never quit.

This episode is for founders, operators, and investors who want the truth behind consumer exits, Shark Tank mythology, and what it actually takes to sell a brand at scale.

Subscribe for substantial founders, comedians, and interesting people on the internet with decent stories and substantial exits.

Billy McFarland joins Due To My Role to walk through his most aggressive idea yet... a live-streamed jet-ski expedition from Utila, Honduras to Venezuela, departing shortly after the Super Bowl and expected to take 17 days coast-to-coast.

The plan is simple and insane: beat Wall Street to Margarita Island by jet ski, acquire beachfront land before institutional capital arrives, host a high-profile “freedom concert,” drive attention and value, then sell the land at a premium. Three seats are offered at $250,000 each, with a 58-foot chase boat, medical crew, and film team following the entire journey, all streamed live.

PE Guy presses McFarland on the obvious questions: risk, legality, safety, and whether this is vision or repetition. McFarland doesn’t dodge it. He openly acknowledges pirates, narcos, rogue governments, and the fact that his safety “is not guaranteed” — arguing that risk is the leverage.

Beyond Venezuela, the conversation goes deeper. McFarland talks candidly about serving four years in prison, joking that parts of it felt like a “forced vacation”, a rare pause from work while also explaining how incarceration reshaped his tolerance for fear, reputation damage, and public opinion.

Most importantly, he outlines a clear pivot away from nightlife and one-off festivals. Festivals, he says, are marketing tools not the endgame. The real ambition is hospitality: permanent hotels in places like Utila or Venezuela, smaller curated groups, and productizing his ability to connect brands with talent at scale. He also discusses efforts to buy back the Fyre brand and reframe it around owned assets instead of spectacle.

This episode isn’t about rewriting history. It’s about what happens after the penalty box — when reputation is damaged, capital is skeptical, and the only way forward is risk, attention, and relentless motion.

Subscribe for substantial founders, comedians, and interesting people on the internet with decent stories and substantial exits.

Wonton Don didn’t follow a plan — he followed curiosity.

In Episode 008 of Due To My Role, Johnny Hilbrant sits down with Barstool Sports’ Foreign Correspondent, Wonton Don, to break down how 8 years living in China, a willingness to lean into weird ideas, and zero interest in a traditional career turned into one of the most durable roles in modern media.

They unpack how Barstool actually works behind the scenes, why creative freedom only exists if you earn it, and how Don built multiple travel and culture franchises without chasing trends or permission. From Drop A Pin to Bald Stool, this conversation explores what it really takes to stay relevant when algorithms shift, audiences fragment, and most creators burn out.

This episode is about leverage, trust, and building formats that compound — not viral moments that disappear.

Subscribe for substantial founders, comedians, and interesting people on the internet with decent stories and substantial exits.

What happens when the narrative is dead, and the press isn’t? In this episode of Due To My Role, Johnny Hilbrant (PE Guy) sits down with Anna Delvey for a conversation most interviews refuse to have—not about the past everyone already litigated, but about control, silence, and why refusing to perform remorse can actually be leverage. Anna breaks down what it’s like to exist as a public figure, people think they understand, while deliberately giving them nothing. Unpacking reputation versus reality, why most “journalism” is humiliation disguised as accountability, how editing power shapes narratives, and why flying under the radar is often the most strategic move in a click-driven economy.

There’s PE Guy energy throughout—satirical, dismissive, and intentional—before Johnny takes over for a real conversation about identity, leverage, and what it actually means to outlive your scandal in this substantial interview with the one and only, Anna Delvey.

This isn’t a redemption arc. It’s a case study in not needing one. Subscribe for substantial founders, comedians, and interesting people on the internet with decent stories and substantial exits.

Johnny Hilbrant (aka PE Guy) sits down with Heather McMahan for a conversation that starts funny, gets real fast, and ends somewhere most business or comedy interviews never go.

What begins as a conversation about comedy quickly becomes a look at how Heather actually runs her career — treating stand-up, touring, podcasting, and specials as a real operating system, not just creative output. She talks candidly about building multiple income streams in an oversaturated creator economy, why she chooses to self-produce her specials before selling them to platforms like Netflix and Hulu, and how owning your audience gives you leverage that no algorithm ever will.

But the heart of the episode is the part you can’t plan for. Heather opens up about losing her father and how sharing grief publicly — before it was “content” — reshaped both her life and her relationship with fans. Johnny shares his own experience losing his sister, and the two unpack how loss rewires ambition, sharpens empathy, and changes what success actually means when you’ve been through something that big.

Along the way, PE Guy still shows up — real estate plays, spending many coins at the Masters merch tent, red carpet moments with E!, and the tension between money, ego, and freedom when creative work starts to scale.

This episode is for anyone building something unconventional — creators, founders, operators — who want the truth about turning personality into product, pain into perspective, and momentum into something that actually lasts.

Subscribe for substantial founders, comedians, and interesting people on the internet with real stories, real leverage, and real exits.

In Episode 005 of Due To My Role, Johnny Hilbrant (aka PE Guy) sits down with Joe Fenti — Boston comedian and former consulting / M&A guy — to talk about the reality of leaving a “serious” corporate career to build a comedy business from scratch.

Joe breaks down what it actually looks like to go full-time comedy: writing every day, turning jokes into sketches, touring the country (35 cities), and self-funding a 60-minute stand-up special with real production (multiple cameras, audio, lighting) — then deciding whether to sell it to a platform or bet on YouTube to build long-term leverage.

They get into the operator side of being a comedian today — how Joe turns internet noise into real demand, protects his material while still feeding the content machine, and runs the entire business behind the scenes (booking, contracts, invoicing, brand) while keeping the creative output consistent.

If you’re into creator economy, stand-up comedy, or the operator side of building an audience-led business, this episode is the truth behind it.

Subscribe for substantial founders, comedians, and the most interesting people on the internet with real stories and substantial exits.

Johnny Hilbrant (aka PE Guy) sits down with Jim Acosta, former CNN Chief White House Correspondent, to unpack what power actually looks like when permission is no longer required.

Jim reflects on his career inside legacy media, covering two presidential administrations, and the moment that put press freedom, access, and authority at the center of the national conversation. From there, the discussion turns to what’s happening behind the scenes in journalism today — the decline of corporate media, the rise of independent platforms like podcasts, Substack, and YouTube, and why audience ownership has become the new leverage.

The episode contrasts the worlds of private equity and legacy media, examines the PE Guy persona as a commentary on power and excess, and explores how journalists, creators, and operators are navigating a system where gatekeepers matter less than direct relationships. It’s a candid conversation about relevance, independence, and building a second act when the old rules stop working.

Subscribe for substantial founders, comedians, and the most interesting people on the internet with real stories and substantial exits.

In Episode 003 of Due To My Role, Johnny Hilbrant (aka PE Guy) sits down with former professional tennis players John Isner and Sam Querrey to talk about what actually happens after elite sports — when the career ends, the prime earning window closes, and identity has to be rebuilt from scratch.

They break down John’s historic 11-hour Wimbledon match that changed the rules of tennis forever, Sam’s blunt take on being priced out of the US Open as a spectator, and how corporate money and influencer culture have reshaped live sports. It’s a candid look at the truth behind money, lifestyle, and what happens when an athletic career ends sooner than most people expect.

This episode dives into retirement shock, staying relevant after the spotlight fades, and the second act through broadcasting, podcasting, and new ventures. If you’re interested in competition, ego, reinvention, and the reality behind high-performance careers — this one hits.

Subscribe for substantial founders, comedians, and the most interesting people on the internet with real stories and substantial exits.