Passion Struck with John R. Miles

Episode 670: Joel Beasley on Starting Over, Stand-Up, and Self-Discovery

Date: September 30, 2025
Guest: Joel Beasley (Modern CTO podcast host, entrepreneur, new stand-up comedian)
Host: John R. Miles

Episode Overview

This episode marks a powerful close to the “Decoding Humanity” series with a candid, in-depth conversation between John R. Miles and Joel Beasley. The focus is on reinvention, starting over after major success, and the radical courage it takes to embrace being a beginner again. Joel Beasley, known for building the #1 global tech leadership podcast Modern CTO, dives into his leap from technology entrepreneur to aspiring stand-up comedian, revealing lessons about persistence, risk-taking, and the mindset necessary to matter—and keep mattering—throughout life.

Key Discussion Points & Insights

Joel’s Early Journey: From Coding to Entrepreneurship

• Learning Coding Young
  • Joel’s father, an Air Force engineer, exposed him to hardware and software projects as a child, creating formative foundations for Joel’s career.

    “As an adult now with three kids, I realized he was just trying to keep me busy so he could get his work done. But it turns out I like doing these small tasks and that went into software engineering for me, man.” (06:42, Joel)

• First Exits Before 25
  • By age 25, Joel had succeeded in multiple software ventures—real estate, fitness, finance—leading to significant financial wins.

Building Modern CTO: From DIY to Global Influence

• From Side Project to Industry Platform

  • The podcast began as a way for Joel to provide advice beyond repetitive one-on-one mentoring. Encouraged by his wife, he started recording conversations, evolving into a full-scale podcast.
  • His goal was networking for a tech leadership job, not realizing the show itself would become the “thing.”

    “I thought the relationships from the podcast would help me achieve that. I didn’t realize the podcast itself would become the thing.” (15:20, Joel)

• Breakthrough Moments & Booking Big Guests

  • Initial growth was slow, grinding through cold emails and 5 episodes a week, which led to personal burnout.
  • The game changed when high-profile CTOs (e.g., Microsoft’s Kevin Scott and T-Mobile’s CIO) proactively came on. Bookings flipped from him looking for guests to being flooded with requests.

    “Within two or three weeks, we were booked up six months in advance because everybody heard those guys, and they're like, now I want to come on.” (11:47, Joel)

• Persistence as DNA

  • Joel attributes much of his success to not giving up, a trait he considers core to his personality.

    “The thing that stayed the same, or maybe it's even... just the ability not to give up, like, the persistence. I've always been pretty steady on persistence, and I think that came from early childhood, slash DNA.” (14:47, Joel)

Surprises and Lessons from Interviewing 1,000+ Leaders

• Most Surprising Guest

  • Oxford AI Professor and Christian apologist John Lennox.

    “Halfway through the conversation, he mentioned something about God... we ended up having this interesting conversation about the intersection of faith and AI... I had no idea he had this background.” (18:38, Joel)

• Biggest Takeaways from Podcasting

  • All guests, no matter how high-profile, are fundamentally just people, sharing human hopes and insecurities.

    “Even if they're the CIO of MasterCard... he has kids, he woke up and he ate breakfast. There's actually so much more in common that we have as just people than anything.” (20:16, Joel)

  • The universal core: “Humanity is generally good.” (20:51, Joel, recounting multiple Uber drivers’ experiences)

Creating Ancillary Businesses and Pivoting through Crisis

• Business Offshoots from the Podcast

  • Originated from requests to clip advice for guest’s teams, morphing into leadership content software—until COVID-19 forced a 90% revenue collapse.
  • Pivoted to show sponsorships for business continuity, and even started a bitcoin mining venture using waste ethane for extremely low energy costs.

    “They’re like, sweet, you’re going to pay us for our trash?... with tax credits and using this wasted energy, our cost was negative 4 cents a kilowatt hour.” (25:42, Joel)

• Candid Perspective on “Green” Industry

  • Joel and John discuss uncomfortable truths about consumer recycling and energy, drawing on personal experiences—underscoring how often reality runs counter to public perception.

The Leap to Stand-Up Comedy: Embracing Reinvention

• The Decision to Start Over—Again

  • After podcasting success, a sense of restlessness and early dreams led Joel to try stand-up, supported by his wife and feedback from old friends.

    “I have to do it because I need very difficult things, otherwise I spiral into depression. So if I’m not trying to solve some incredibly difficult problem... I’m uninterested in life itself.” (34:32, Joel)

  • He aims huge: “The biggest goal I could come up with is to sell out a stadium.” (34:32, Joel)
  • Comedy pursuit is consciously “slow and steady” to avoid burnout, balancing family and prior business obligations—building from open mics to regular club spots in 7+ months.

• Testing Material & Bombing on Stage

  • Systematically records, reviews, and notes every set, following the Steve Martin and Jerry Seinfeld method. About 90% of written material gets cut.

    “I record every set that I do and I watch back and I note the laughs... then I adjust my set accordingly.” (41:09, Joel)

• Clean Comedy as a Niche

  • Chooses family-friendly, “subjectively clean” material that he’d want his own kids to watch—seeing an underserved audience for smart but non-explicit comedy.

Risk, Resistance & Redefining Success

• Why Most People Stay Comfortable

  • John frames Joel’s journey as the opposite of the “hero’s journey complete”—he’s back in the trenches, a beginner again.
  • Joel shares his personal commitment formula for big pursuits:

    “Decide that you’re going to do it whether you’re successful or not until you die... When I went into it with the podcast, I said, I’m going to do this until I die, whether or not I’m successful. And that’s just who I am now.” (46:32, Joel)

• On Imposter Syndrome and Identity

  • Both John and Joel joke about the awkwardness of telling people they’re “professional podcasters” or comedians after years in traditional, respected tech roles.

    “I have to tell you, I’m unemployed twice. I’m a podcaster and a comedian. And I just let them think that. Whatever they think.” (50:34, Joel)

• Handling Failure Publicly

  • Joel’s first bomb stories: from performing to near-empty rooms to awkward audience moments.

    “She goes, I have one son, and he died last week. And I was like, why are you raising your hand at a comedy show?” (51:17, Joel)

Lightning Round (55:07–56:57)

• First Live Stand-Up, Favorite Joke, Essential Gadget, and More
  • First Stand-up Show: At McCurdy’s Comedy, Sarasota, FL (doesn’t recall the comic).
  • Favorite Joke: A life insurance bit about his wife (findable on Instagram).
  • Gadget: “Fitbit, baby. Without a doubt, the best, most positive impact any technology has ever had on my life.” (55:33, Joel)
  • Parenthood Surprise: “How you can love the kids so much and simultaneously wish they would just go to bed.” (55:45, Joel)
  • Comedy’s Leadership Lesson: “Nervous or not, when it’s time to do the thing, you just got to do the thing.” (56:04, Joel)
  • Ultimate Martian Principle: “I would build a stadium and do a set and then die.” (56:49, Joel)

Notable Quotes & Memorable Moments

• On Choosing New Challenges:

  “Becoming Passion Struck isn’t a one time event. It’s a lifelong practice of saying yes to the next thing that scares you, stretches you and forces you to grow.” (03:26, John Miles)

• On Self-Validation & Support:

  “I went and talked to people who were my friends in elementary school and middle school... they all said the same thing. They're like, because you're funny.” (32:32, Joel)

• On Comedy & Persistence:

  “It takes a lot of work to come up with one solid minute of stage timed comedy... the unsexy truth about doing anything great is you need some really solid systems in place that are consistent and stable, and then you just have to wake up and manufacture the desire to operate the systems consistently over time.” (42:49, Joel)

• On Transitioning Identities:

  “If you said ‘software engineer’ before that, like, a lot of clout came along with that... then when you say podcaster, they have all these ideas in their head that aren’t as positive as software engineer. But I just—I don’t care anymore.” (50:34, Joel)

• On Facing Failure:

  “Bombing is essentially when whatever content you're doing is not working with the crowd... and I'm comfortable with the silence when you're getting started, you're trying stuff.” (51:17, Joel)

• On Choosing to Keep Climbing:

  “Growth isn’t about reaching the top of one mountain. It’s about having the courage to climb the next one... Passion Struck is a process, not a destination.” (57:22, John Miles)

Timestamps for Major Segments

• Joel’s Early Influences and Coding Origins — 06:42
• Initial Growth of Modern CTO Podcast — 09:43–12:22
• Breakthrough Big-Name Guests — 11:47
• Persistence as a Core Value — 14:47
• Podcast as Career Catalyst, Not Just Content — 15:20
• Most Surprising Podcast Guests — 18:38
• Biggest Lessons from 1,000+ Interviews — 20:16–21:30
• Ancillary Businesses & Bitcoin Mining — 23:06–25:42
• The Harsh Realities of Recycling — 27:25–29:49
• Commitment to Comedy, Goal of Selling Out a Stadium — 34:32
• Feedback Loops, Material Writing, and Bombing — 41:09–42:49
• Comedy and Clean Material for Family Audiences — 44:01–45:49
• Forming an Unbreakable Commitment — 46:32
• Imposter Syndrome as Podcaster/Comedian — 50:34
• Bomb Stories & Audience Engagement Fails — 51:17
• Lightning Round: Jokes, Gadgets, Leadership Lessons — 54:46–56:57
• Episode Wrap-Up: The Courage to Begin (Again) — 57:22

Final Takeaway

This conversation is not just a chronicle of career pivots and creative hustle; it’s a blueprint for continual personal reinvention. Joel Beasley’s story highlights that “mattering” is always a choice, not a finish line. The courage to start over—and persist until mastery—reveals the real recipe for purposeful growth.

For more about Joel’s journey into comedy and beyond, visit joelcomedy.com.

Listen & share if you’re ready to pause, reflect, and reimagine your own next chapter.