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PODCAST

The Corporate Escapee

Hey, I’m Brett Trainor — corporate escapee, business builder, and your guide to building life after corporate. After 25+ years in corporate, I realized the system wasn’t built for freedom or happiness. Now I’m helping other corporate pros not just escape — but thrive as independent solopreneurs, building multiple income streams and more control over their time, work, and life. I study what’s working in the new world of solo business — the models, the mindset, and the experiments that lead to freedom

business entrepreneurship

All Episodes

33:11

Healthcare for a Company of One: A Real Alternative...

The Corporate Escapee ·

2025/10/30

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, what’s covered, what’s not, and where this is all headed (biomarkers, portable benefits, and association plans). If you’ve ever said “I’d leave corporate,

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53:10

Beyond the Escape: How to Stay Free (and Profitable)...

The Corporate Escapee ·

2025/10/29

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 businesses.Jenni shares her journey from The New York Times to building a six-figure business working just 25 hours a week. Together, Brett and Jenni unpack

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31:08

$5K in 48 Hours: Turning Your Experience into a...

The Corporate Escapee ·

2025/10/24

GenX Escapees: this one’s your playbook. Michael Himmelfarb (multi-time guest and early Escapee OG) breaks down how to productize a fast, high-value, AI-enhanced consulting offer—think $5K in 48 hours—by letting AI handle the heavy lifting while you deliver the human superpowers clients actually pay for: judgment, creativity, prediction, and trust. We get into pricing, point solutions, and why your domain expertise beats “AI-only” every time.You’ll learn • Why buyers now demand crystal-clear

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22:05

17 Ways (Plus 2 Bonus) to Monetize Your Corporate...

The Corporate Escapee ·

2025/10/22

About this episodeIn 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 outside trying to replace your income, this episode is the playbook. From fractional and advisory work to user-generated content, workshops, and buying a

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41:17

The Ignorance Tax: How to Build a Lean, Automated...

The Corporate Escapee ·

2025/10/14

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 GenX escapees scale their businesses without hiring full-time employees. Paul also explains how he’s helping medical professionals escape the bureaucracy

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35:46

From Corporate to Calling: A Practical Path to...

The Corporate Escapee ·

2025/10/11

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 can take while still in corporate. No dogma required—just a better operating system for work and life.You’ll learn • What a “Life Quest” is and how to

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45:24

Local First, Personal Always: Selling Solo to Small...

The Corporate Escapee ·

2025/10/08

Robert Lock went from corporate sales leadership to running supply chain during COVID—then used that “between lanes” moment to launch his own firm, Buffalo Mountain Sales Strategies.In this episode, he and Brett dig into how GenX escapees can win clients by going local-first and relationship-heavy, not enterprise-style transactional.You’ll Learn💡 How to build a referral engine from scratch:→ Daily LinkedIn connects with a simple, honest message→ Wait 24 hours→ Invite to a virtual coffee→ Leave

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36:05

Fans First: Jesse Cole’s Playbook Behind the Savannah...

The Corporate Escapee ·

2025/09/27

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 • 17 Major League Baseball parks sold out on their 2025 World TourThis conversation captures Jesse’s philosophy before the explosion—and it’s more relevant

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33:12

The Chief Energy Officer: What GenXers Can Learn from...

The Corporate Escapee ·

2025/09/24

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 (and $250K in value) at Kansas to find his true pathHow he walked on to Iowa State’s Top 25 basketball program after not playing for 3 yearsHis role as the

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43:34

Your AI Advantage: Why GenX Escapees Are Built to...

The Corporate Escapee ·

2025/09/23

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: micro-SaaS, productized services, and month-to-month offers that business owners can say “yes” to quickly.Key TakeawaysGenX Advantage: We’ve lived analog →

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32:26

Your First Revenue Stream Outside Corporate (with Lee...

The Corporate Escapee ·

2025/09/17

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 fences or waiting years to replace a corporate paycheck.In this episode, you’ll learn:How User-Generated Content (UGC) works and why it’s perfect for GenXers

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46:23

Networking Made Simple: David Ackert’s Proven Short...

The Corporate Escapee ·

2025/09/12

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 20+ years helping professionals grow their books of business and has distilled his research into a simple, proven framework that removes the guesswork

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38:04

All Things Fractional: Your Complete Guide with...

The Corporate Escapee ·

2025/09/05

Fractional, Defined: How to Lead (Not Freelance) with Karina MikhliWhat 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), how to price and structure your work, and why networking—not job boards—drives real opportunities.We cover: • The difference between fractional vs

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50:22

Nail Your Messaging and Master the 6 Questions Every...

The Corporate Escapee ·

2025/08/27

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 solopreneurs and small business owners design simple, effective growth strategies centered around relationships.We dive into: • Why most escapees waste time on

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29:34

From Corporate Stress to Strength Training: A Dual...

The Corporate Escapee ·

2025/08/21

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 goods, Greg walked away to follow his lifelong passion for health and fitness. Today, he runs a growing training facility in Tennessee, helping athletes

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36:26

Escaping Corporate Identity: How Thea Watkins Built a...

The Corporate Escapee ·

2025/08/21

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 runs a portfolio career that blends teaching, coaching, facilitation, and consulting. She’s proof that your decades of experience are not only valuable

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40:40

Portfolio Life: Building Purpose and Freedom After...

The Corporate Escapee ·

2025/08/15

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 30-year journey—and what that means for planning.How our latchkey kid upbringing shaped Gen X resilience, adaptability, and desire for freedom.The social side

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40:38

UGC for Gen X: How to Make Money Creating Content (No...

The Corporate Escapee ·

2025/08/08

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-figure corporate income in just 14 months.We break down exactly what UGC is, why brands want creators over traditional actors, and how YOU can get started—no big

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48:45

From Burnout to Purpose: Escaping Corporate and...

The Corporate Escapee ·

2025/07/09

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 corporate won’t take care of them • How he found his first customers (and how you can too) • The rise of solo businesses—and why GenX is perfectly

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38:25

Escape Without Breaking: Shelley McIntyre’s 3-Phase...

The Corporate Escapee ·

2025/06/09

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 (yes, even the good ones) • How to rediscover your identity after decades in corporate • The key mindset shift GenXers must make to take action before it’s too

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306 results

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