Best Brett Trainor Podcasts (2025)

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17 Ways (Plus 2 Bonus) to Monetize Your Corporate Experience w/Brett Trainor 22:05

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12d ago22:05

22:05

About this episode In this solo “CliffsNotes” episode, Brett breaks down how to actually make money from your corporate experience — not theory, not startup fantasy — just 17 real ways GenXers are doing it (plus 2 bonus options if you’ve got some capital to invest). Whether you’re still in corporate wondering if there’s a way out, or already on the…

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Healthcare for a Company of One: A Real Alternative for Solopreneurs w/Tom Morrissey 33:11

4d ago33:11

33:11

Healthcare is the #1 concern from wannabe escapees DM Brett about. Today, benefits veteran and fellow escapee Tom Morrissey breaks down a solo-friendly health plan designed for one-person companies: Solo Health Collective. We cover who qualifies, how underwriting your business (not you as an individual) changes the game, pricing logic, networks, wh…

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Beyond the Escape: How to Stay Free (and Profitable) as a Solopreneur w/ Jenni Gritters 53:10

5d ago53:10

53:10

What happens after you escape corporate? How do you make your solo business work long-term—without burning out or losing the freedom you left for? In this episode, Brett sits down with Jenni Gritters, author of The Sustainable Solopreneur and coach to creatives, consultants, and coaches who want to build profitable, flexible, and fulfilling solo bu…

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The Future Isn’t AI Automation — It’s AI Augmentation (with Michael Himmelfarb) 31:08

11d ago31:08

31:08

GenX built the systems everyone’s now trying to automate — and that’s exactly why we’re built for what’s next. In this episode, I’m joined by Michael Himmelfarb, one of the original corporate escapees, to talk about why the real opportunity with AI isn’t automation…it’s augmentation. Michael shares how he rebuilt his consulting business by combinin…

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The Ignorance Tax: How to Build a Lean, Automated Solo Business with Paul Durelli 41:17

20d ago41:17

41:17

Paul Durelli returns to The Corporate Escapee Podcast one year after his first appearance to share what’s changed, what’s working, and where he sees the biggest opportunities for corporate and medical professionals looking to escape traditional systems. In this conversation, Brett and Paul explore how AI, automation, and virtual assistants can help…

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From Corporate to Calling: A Practical Path to Purpose w/ Lisa Petrilli 35:46

23d ago35:46

35:46

If your “great job” feels increasingly empty, this one’s for you. Former corporate leader Lisa Petrilli (Medline/Baxter) shares a practical approach to discovering your Life Quest—the next chapter where purpose, agency, and freedom replace autopilot. We dig into choice vs. circumstance, how to reframe fear and uncertainty, and simple steps GenXers …

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Local First, Personal Always: Selling Solo to Small Business Owners (with Robert Lock) 45:24

27d ago45:24

45:24

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Fans First: Jesse Cole’s Playbook Behind the Savannah Bananas Phenomenon 36:05

1M ago36:05

36:05

When I first interviewed Jesse Cole—the man in the yellow tux and founder of the Savannah Bananas—the team had just started selling out games in Savannah. Fast forward to today, and the Bananas are a global sports and entertainment phenomenon: • A ticket waitlist of more than 3 million people • Stadiums of 70–80,000 fans packed to see Banana Ball •…

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The Chief Energy Officer: What GenXers Can Learn from GenZ Purpose w/Conrad Hawley 33:12

1M ago33:12

33:12

What GenXers stuck in corporate can learn from a 22-year-old former D1 athlete who walked away from the easy path, found his purpose, and chose to serve others—even when it was uncomfortable. I like to connect the dots and showcase what's possible if we break out of our comfort zones 🔑 In This Episode: Why Conrad left a full football scholarship (a…

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Your AI Advantage: Why GenX Escapees Are Built to Cash In (with Naveen Aggarwal) 43:34

1M ago43:34

43:34

Brett and Naveen break down how GenX escapees can use AI to work faster, earn more, and de-risk the leap from corporate. You’ll learn where AI actually helps (and where it doesn’t), how to turn your experience into simple, repeatable, AI-enabled services, and why singles (small wins) beat swinging for enterprise home runs when you’re solo. Think: m…

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Your First Revenue Stream Outside Corporate (with Lee Ann Pepper) 32:26

2M ago32:26

32:26

We’re launching a new recurring segment with Lee Ann Pepper focused on real-world revenue ideas for corporate escapees. If you’ve ever asked yourself, “How would I actually make money if I left corporate?” this episode is for you. Lee Ann and I break down practical, low-risk ways GenXers can start monetizing today—without swinging for six-figure fe…

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Networking Made Simple: David Ackert’s Proven Short List Framework for Escapees 46:23

2M ago46:23

46:23

For most corporate escapees, networking and sales feel like the biggest hurdles to building a solo business. With hundreds of LinkedIn connections and decades of contacts, it’s easy to feel overwhelmed—or worse, to avoid networking altogether. Enter David Ackert—author of The Short List and winner of the 2025 Non-Fiction Book Award. David has spent…

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All Things Fractional: Your Complete Guide with Karina Mikhli 38:04

2M ago38:04

38:04

Fractional, Defined: How to Lead (Not Freelance) with Karina Mikhli What does “fractional” really mean—and is it the right next step after corporate? In this episode, I sit down with Karina Mikhli, founder of Fractionals United, Fractional COO, and COO for the Fractional Leadership Alliance. She breaks down what fractional leadership is (and isn’t)…

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Nail Your Messaging and Master the 6 Questions Every Client Will Ask w/ Tom Freedman 50:22

2M ago50:22

50:22

One of the biggest challenges GenX escapees face after leaving corporate isn’t expertise—it’s business development. How do you find customers, create clarity in your message, and grow without getting stuck in trial-and-error mode? In this episode, I sit down with Tom Freedman, a lifelong entrepreneur who has built six businesses and now helps solop…

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From Corporate Stress to Strength Training: A Dual Playbook for GenXers 29:34

2M ago29:34

29:34

Dual Takeaway: This episode is a two-for-one: inspiration for escaping corporate and practical fitness guidance for living longer, stronger, and on your own terms. What happens when you realize corporate life just isn’t for you—before it consumes decades of your career? Greg Bogdanski found out early. After stints in investment banking and consumer…

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Laid Off After 27 Years—And Finding Fulfillment Beyond Corporate w/ Thea Watkins 36:26

2M ago36:26

36:26

After 27 years in corporate—including an executive role—Thea Watkins never imagined she’d end up running her own business. A layoff forced her to pause, reflect, and rethink what she really wanted. Instead of jumping back into another corporate job, Thea leaned into her passions: leadership, people development, and inclusive workplaces. Today, Thea…

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Portfolio Life: Building Purpose and Freedom After Corporate with Joy Levin 40:40

3M ago40:40

40:40

What does “retirement” really look like for Gen Xers—and why do so many struggle with it? In this episode, I sit down with Joy Levin, market research consultant turned retirement coach, who helps Gen X professionals design their encore years with purpose, connection, and freedom. We dive into: Why retirement is no longer a five-year chapter but a 3…

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UGC for Gen X: How to Make Money Creating Content (No Followers Needed) W/Megan Collier 40:38

3M ago40:38

40:38

Episode Summary: Think UGC (User Generated Content) is only for 20-somethings? Think again. In this episode, I’m joined by Megan Collier—UGC creator, coach, and champion for Gen Xers and Boomers who want to turn their creativity into a revenue stream. Megan shares how she went from scrolling TikTok with just 200 followers to replacing her six-figur…

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From Burnout to Purpose: Escaping Corporate and Building a Life That Works 48:45

4M ago48:45

48:45

In this special episode, Brett flips the mic and joins John Browning on the Building Your Life Podcast. They dive deep into what it really means to escape corporate life and build something better—on your terms. Brett shares: • His journey from 25 years in corporate to solo consulting and fractional work • Why GenX is waking up to the reality that …

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Escape Without Breaking: Shelley McIntyre’s 3-Phase Framework for Leaving Corporate 38:25

5M ago38:25

38:25

She’s back for part two! Shelley McIntyre returns to break down the exact framework she uses to help burned-out GenX professionals escape corporate life—without hitting rock bottom first. If part one was about why we escape, this one is about how to do it—mentally, emotionally, and tactically. We cover: • Why grief is a part of every transition (ye…

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The LinkedIn Escape Plan: How Joe McKay Left Government and Built a Life in France 51:27

5M ago51:27

51:27

Joe McKay left a government job in Australia to raise his family in rural France—and stumbled into the solopreneur life along the way. In this episode, Joe shares how one consulting gig turned into a thriving ghostwriting business and agency, all built on the back of his personal brand on LinkedIn. We talk about: • The “fork in the road” moment tha…

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The Anti-Hustle Guide to Doing Better Work with Paul Shirley 53:48

5M ago53:48

53:48

This isn’t a future-of-work episode. It’s a how-to-work-differently episode. Paul Shirley returns for his third appearance on the show—and this time, we go deep. We’re talking focus, structure, guilt, failure, personal infrastructure, and why GenX escapees need systems more than strategies. If you’ve ever felt like: • You “should be able to do more…

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The Salary Gap Illusion: Why Going Solo Isn’t as Risky as You Think 16:31

6M ago16:31

16:31

Feeling stuck between your 6-figure corporate salary and the dream of going solo? You’re not alone—and the fear is real. But the risk? It’s not as big as you think. In this Cliff Notes solo episode, Brett breaks down “The Salary Gap Illusion”—why so many GenXers stay stuck in jobs they’ve outgrown, and how to start building your bridge to freedom t…

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Jumping Out of the Corporate Plane—with a Parachute (and a Plan) with Tonya McKenzie 39:13

6M ago39:13

39:13

In this inspiring episode, Brett chats with PR powerhouse Tonya McKenzie, a true OG in the escapee world, having built her own agency nearly a decade ago. Tonya shares the story of how her husband (a fellow escapee) gave her the push she needed to leap from corporate—and how she turned that leap into a thriving PR and media business. From launching…

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If It’s Not a Hell Yes, It’s a No: Why Clarity Comes After Action w/Shelley McIntyre 41:40

7M ago41:40

41:40

Shelley McIntyre didn’t just leave corporate—she walked away from a long career in tech and consulting and into something completely unexpected: grief coaching. But as Shelley quickly discovered, grief isn’t just about death—it’s also what we experience when leaving jobs, identities, and entire versions of ourselves behind. In this candid conversat…