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.

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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.

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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.

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