Modern CTO – Episode Summary

Episode Title: From Inventing a Microprocessor to Full-Time Tech Comedian with Don McMillan
Release Date: March 9, 2026
Host: Joel Beasley (ProSeries Media)
Guest: Don McMillan – Engineer turned full-time tech comedian

Episode Overview

In this entertaining and insightful episode, comedian and former microprocessor engineer Don McMillan joins host Joel Beasley to share his unique journey from the world of Silicon Valley and computer chip design to becoming a full-time stand-up comic specializing in tech and engineering humor. Don discusses the challenges and rewards of following one’s passion, the evolution of his comedy (notably his pioneering use of PowerPoint), and the intersection of engineering thinking and stand-up performance. The conversation covers career pivots, family balance, adapting to technology-driven comedy, and anecdotes from the road and raising a techie son.

Key Discussion Points & Insights

1. Don’s Unplanned Career Pivot (00:32 - 05:06)

• Don describes his start as a math-and-science-loving student who became a chip designer at Bell Labs, highlighting the research culture and pressure of Silicon Valley in the 1980s.

  • “I was good at engineering... but I wasn't fulfilled.” (00:32)
  • Burnout and lack of fulfillment led him to experiment with stand-up comedy.

• Joel and Don trade stories of pivot points—moments of introspection about where true passion lies.

  • “Wouldn't it be better if I had a job that I had passion for? Wouldn't I be better at it and be a happier person?” – Don (06:11)

2. Early Encounters with Comedy (07:08 - 12:30)

• Don reflects on formative comedy experiences, including sneaking in to see Steve Martin as a teenager and trying open mics in Silicon Valley.

  • “When I was 16, I snuck in to see Steve Martin... and I just went, wow.” (08:45)

• The impact of being recognized by a radio show listener, which validated his connection to audiences.

  • “Somebody called in and said, ‘when's that Don McMillan coming back on your show again?’... that changed my life.” (07:40)

• Engineering approach to joke-crafting: "A/B testing" material and persistently iterating sets.

3. Breaking into Full-Time Comedy (12:55 - 17:53)

• Don describes performing 323 nights in a single year while balancing a day job, eventually entering the San Francisco Comedy Competition, and booking a national commercial that enabled him to quit engineering.

  • “If there’s no better time to quit now, I’m getting notoriety and I booked a national commercial...” (13:35)
  • “I didn’t lose money my first year, which is a victory, but it’s because I’m an engineer, and I went into cheap mode.” (17:53)

• Supportive boss and ongoing heckling from former colleagues.

  • “I can’t get away from my old job...they heckle me. ‘Did you ever finish the test program?’” (14:48)

4. The PowerPoint Revolution & Corporate Comedy (20:48 - 26:52)

• Don’s signature PowerPoint comedy was born at a 1999 corporate event after mocking a colleague’s painfully technical presentation.

  • “I go, I’m gonna show what not to do in PowerPoint and I’m gonna make it funny.” (20:54)

• The PowerPoint format became central to his act in the corporate world, later adapting to clubs with his own projector equipment.

• Visual punchlines and "clicker timing" as an evolved comedic device.

  • “This hand is a comedy genius.” (25:48)

• The science and structure behind mixing verbal and visual setups for sustained audience surprise and engagement.

5. Customizing Comedy and Comedy as a Service (29:32 - 32:44)

• Don explains his heavily customized sets for corporate clients, incorporating company-specific terminology, culture, and inside jokes.

  • “About 50% of my corporate sets are custom... The more specific a joke is, the better it’s going to be.” (30:33)
  • “Comedy is a service, I’m providing a laugh service to relieve the stress and humdrum of technology jobs.” (32:44)

• Strategies include research, pre-show calls, joke libraries, and real-time corporate jargon humor.

6. Family, Fatherhood, and Work-Life Balance (33:43 - 38:49)

• Don shares how working primarily as a corporate comic allowed him to be present for his son’s upbringing.
  • “I was home a lot... doing corporates allowed me to earn money, do comedy, and be there for my son.” (35:32)
• Reflections on being a comic versus engineer dad, and observations about his son’s tech-savvy and empathetic nature.

7. The Modern Tech Comedy Landscape and AI (28:26 - 29:32)

• Don discusses his current AI-themed tour (“Don McMillan 2.0”), in which he pits his stand-up skills against AI-generated jokes—evaluating which is funnier onstage using Venn diagrams.

8. Community & Closing Highlights (41:26 - 43:51)

• Don invites listeners to see his live shows, noting the surprising nerdiness of audiences across the country—especially in places like Arkansas due to local industry (“I could not get nerdy enough!”) (42:41).
• Final thoughts on the evolving nature of career and family, and the joy of sharing comedy.

Memorable Quotes & Moments

• On Silicon Valley culture:
  “It was the most amazing incubator of technology in the 80s... you had no life. It was very stressful.” – Don (01:44)

• On discovering comedy’s impact:
  “I have a relationship that I'm building with the audience. And I went, this is what I didn't have in engineering.” – Don (07:56)

• Don’s PowerPoint humor explained:
  “Apparently, I'm the world's number one Venn diagram comedian. The MasterCard logo is a Venn diagram... in the middle, that's your monthly salary.” (23:24)

• On timing in PowerPoint comedy:
  “My clicker hand has mechanically learned comedy timing because I need to push the button exactly when the punchline is going to come up.” (25:12)

• On customizing corporate sets:
  “About 50% of my corporate sets are custom... If I can learn about their world, they're going to love it.” (30:33)

• On raising a techy son:
  “He comes to me at 10 and he goes, ‘Dad, I hope you don’t mind, I reconfigured the server...’ I love you, son.” (37:32)

• On the future:
  “I'm trying to figure out what to do with this part of my life. It's another part. So it never stops.” (38:58)

Notable Segments & Timestamps

• Don’s engineering to comedy transition: 00:32 – 02:52
• Burnout and lack of fulfillment: 01:44 – 05:06
• First comedy experiences & validation: 07:08 – 08:34
• Early open mic years and the grind: 12:55 – 14:16
• Quitting engineering for comedy: 13:35 – 17:53
• Birth of PowerPoint comedy: 20:48 – 23:17
• Sample Venn diagram bit: 23:27 – 24:45
• Visual punchlines & timing: 25:11 – 26:02
• Customization and comedy as a service: 29:32 – 32:44
• Family, fatherhood, and home life: 33:43 – 38:49
• Touring and surprising nerd hubs: 41:36 – 43:51

Where to Find Don McMillan

• Website: donmcmillan.com / technicallyfunny.com
• Current tour: “Don McMillan 2.0 – Powered by AI”
• Online: Links to Don’s top bits are mentioned as available in the episode’s show notes.

Summary prepared for listeners seeking a comprehensive, engaging recap of the episode’s conversation and themes.