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 Tour

This conversation captures Jesse’s philosophy before the explosion—and it’s more relevant than ever for GenX escapees and founders building solo businesses. His blueprint proves you don’t need to be the biggest, you need to be the only.

In this episode:

• Jesse’s “ONLY” framework for standing out (Own the problem, Noise, Love, Why)

• Why customers are transactional but fans never leave

• How small first/last impression touches create “happy tears”

• The 5 E’s of experience: Eliminate, Entertain, Experiment, Engage, Empower

• Why constraints drive creativity (and why experiments beat iterations)

• The Visionary + Integrator combo every founder needs

For Escapees:

A great example of what following your dreams can lead to. Also, great insights for building a solo business.

If you’re landing your first client or building a lifestyle business, Jesse’s insights map perfectly: different is better than better. Create fans, not customers—and let them do your marketing for you.

Resources

• Jesse Cole LinkedIn: https://www.linkedin.com/in/yellowtuxjesse/

• Books: Fans First & Find Your Yellow Tux

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 path
• How he walked on to Iowa State’s Top 25 basketball program after not playing for 3 years
• His role as the team’s “Chief Energy Officer” and how he brought discipline and heart into everything he did
• How struggle, loneliness, and discomfort became the fuel for transformation
• The importance of self-awareness, emotional honesty, and earning your identity
• Why he’s building a speaking career focused on pouring into others—and how that fills him with purpose
• How he structures his solo life post-athletics and why discipline still anchors him

✨ Why This Episode Matters for GenXers:

• If you’ve been telling yourself it’s too late to start over… listen to this episode.
• If you’ve been waiting for the “right time” to make a move… listen to this episode.
• If you’ve been going through the motions… this is your wake-up call. 🫵

Conrad may be GenZ—but his mindset, energy, and willingness to act despite fear is a blueprint for anyone ready to take back control.

Brett’s Take:

“This episode hit me. Conrad’s honesty, discipline, and self-awareness are things most of us spend decades trying to develop. But more than that, he took action. He walked away from safety and toward purpose. GenXers—we can learn a lot from that.”

🔗 Connect with Conrad:

• LinkedIn: https://www.linkedin.com/in/conradhawley

• Just Google him—he’s easy to find and open to speaking engagements and collaborations.

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 Takeaways

• GenX Advantage: We’ve lived analog → digital → internet → mobile. We know how to train people—now we train AI. We also know when outputs are “off.”
• AI as Fractional Workforce: Treat AI like your on-demand researcher, analyst, designer, scheduler, and SDR. One subscription, many “roles.”
• Start with Singles: Stop chasing six-figure whales out of the gate. Package $1–5K/month services that solve one need deeply, repeat it across clients.
• Outcome > Hours: Price the result (clean CRM, personalized outreach engine, faster proposals), not your time. AI compresses hours into minutes—that’s the point.
• Productize the Process: Turn your workflow into a mini system: inputs → AI-assisted steps → valuable output. Reuse 80%, customize 20%.
• Risk Wins Deals: Month-to-month + clear ROI beats open-ended fractional promises for most SMBs.

Practical Use Cases We Cover

• Lead gen & personalized outreach at scale

• CRM cleanup & contact enrichment

• Proposal/slide creation (e.g., Gamma)

• Research & meeting prep “briefings”

• Contract review & red-flag summaries

• Agents & light automations (only after nailing the manual workflow)

Simple Monetization Paths (Examples)

• $2–5K/mo: “Done-for-you” outbound engine (200 targeted emails, replies routed, CRM updated).
• $1–3K flat: CRM cleanup + enrichment + basic dashboard.
• $1–2K/mo: Founder research briefs + talk tracks before key meetings.
• $3–8K setup + $1–3K/mo: Build a lightweight, repeatable micro-SaaS/workflow (pricing, content kits, hiring screens) for a niche.

Timestamps

• 00:00 Intro & why AI is a GenX superpower

• 03:30 From big-corp AI to solo/SMB impact

• 06:10 Training people vs. training AI (and knowing “good”)

• 11:20 AI as your fractional team: practical tools & roles

• 16:45 Thought partner use case (Brett’s real examples)

• 23:30 Singles over home runs: structure simple wins

• 29:45 Value pricing when AI compresses your time

• 34:20 Risk, ROI, and easy “yes” offers for SMBs

• 38:45 Partnering to productize (stack skills → stack revenue)

• 42:50 Action plan & where to find Naveen

Memorable Lines

• “AI is the great equalizer—your fractional workforce in one subscription.”

• “Don’t sell AI—sell a solved problem that AI helps deliver.”

• “GenX knows what ‘good’ looks like. That’s the edge 20-somethings can’t fake.”

Resources Mentioned

• Explained Consulting: explained.consulting

• Gamma for slide/proposal generation

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 who don’t want to be influencers.
• The new inventory-free e-commerce model that lets you launch products without warehouses or Amazon risk.
• Why the Connector Model (introductions + network leverage) is a hidden path to retainer + commission income.
• How to get paid for hiring advisory—helping SMBs make better hires using your experience.
• Why small, repeatable service retainers often add up faster than chasing one big consulting deal.
• The mindset shift from swinging for home runs to stacking singles for steady cash flow.

Enjoy and let us know what you think!

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 from networking.

In this episode, David shares how to replace random outreach with a focused, confidence-building system that actually drives results.

What You’ll Learn:

• Why a bloated network isn’t useful—and how to focus on the 9–35 relationships that matter most
• The three categories every escapee needs: prospects, clients, and connectors
• How to re-engage dormant ties for new opportunities
• The “14 interactions” rule and why most people quit too soon
• Why doing structured free work can accelerate your first paying clients
• How GenXers’ natural problem-solving and “be helpful” mindset is a superpower in building trust
• Why confidence isn’t faked—it grows naturally from following a consistent system

About David Ackert

David is the President of Ackert Inc., creator of the PipelinePlus Tracker app, and author of The Short List. He has dedicated his career to helping professionals simplify business development through intentional, value-driven relationships.

👉 Connect with David:

• Website: pipelineplus.com

• LinkedIn: David Ackert

👉 Resources:

• Get your copy of The Short List wherever books are sold

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), how to price and structure your work, and why networking—not job boards—drives real opportunities.

We cover:

• The difference between fractional vs. consulting vs. interim

• Karina’s 3-2-1 ops model for structuring engagements

• How to avoid the hourly trap and sell on outcomes

• Red flags, best practices, and when agencies might make sense

• Why SMBs are the sweet spot (and when it’s too early/too big for fractional)

📌 Links & Resources

• Connect with Karina: linkedin.com/in/karinamikhli

• Join the community: FractionalsUnited.com

• Fractional definitions: fractionaldefine.com

• Free Escapee Starter Kit: Download here 

🎙️ Subscribe to The Corporate Escapee Podcast for more GenX stories, tools, and strategies to help you find your path to freedom.

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 “shiny” strategies that don’t move the needle

• The Three-Headed God of Growth—marketing, business development, and sales—and how solos should prioritize them

• Tom’s SAM framework (Solution, Audience, Message) and how it fuels growth

• The 4 Cs of messaging: Clear, Concise, Compelling, and Consistent

• How to handle the six questions you’ll face on every discovery call

• Pricing strategies that balance affordability for clients with sustainability for you

• Why clarity and consistency in your message is the #1 growth driver

Tom doesn’t just share theory—he lays out practical steps you can apply immediately to land clients faster, refine your message, and build a business you actually want to run.

And yes, we already teed up Part 2—where Tom will come back to break down how to consistently get in front of the right people.

Connect with Tom Freedman:

• 🔗 LinkedIn: Tom Freedman

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 and adults build strength, resilience, and confidence.

In this conversation, Greg shares the lessons he learned from leaving corporate early, the challenges of opening a gym from scratch, and how fitness principles apply to GenX escapees looking for longevity and freedom.

We discuss:

• Why Greg knew corporate wasn’t his long-term path

• How he turned a side passion into a business—starting with training kids in a park

• The role of experimentation and iteration when launching something new

• Marketing strategies that are working for small gyms today (Instagram, Facebook, email)

• The importance of play, movement, and mental resilience for kids (and adults)

• Fitness and longevity tips for GenXers:

• Why walking is the most underrated exercise

• How to structure a simple 3-day strength training plan

• The 80/20 approach to cardio and nutrition

• Why building a plan—whether in business or fitness—is the key to freedom

Connect with Greg:

• Instagram: https://www.instagram.com/greg_bogdanski_iii/

• https://www.instagram.com/peak_performancetraining_tn/ 

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 but highly transferable into meaningful and fulfilling work.

In this episode, we cover:

• Why your corporate identity can be the hardest thing to leave behind

• How to intentionally build an external network after decades in one company

• The path from executive leadership to adjunct professor (and why more escapees should consider it)

• The real value of coaching—for both yourself and your clients

• Practical advice for preparing mentally and emotionally for a corporate exit

• Why focusing on values and fulfillment is more powerful than chasing a “perfect” plan

If you’re curious about life after corporate, in the middle of transition, or already building your next chapter, Thea’s story shows that fulfillment and freedom are possible—if you’re willing to step into the unknown.

Resources & Links:

• Website: theawatkinsconsulting.com

• LinkedIn: Thea Watkins

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 of retirement—why isolation is one of the biggest post-corporate risks and how to avoid it.
• Common mistakes people make when transitioning out of corporate life.
• How to create your own “portfolio life” built on purpose, flexibility, and joy.
• Why couples need to plan their next chapter together—before one person books the world trip and the other says, “But what about the grandkids?”

Whether you’re years away from leaving corporate or already in your next chapter, Joy’s insights will help you think bigger, plan smarter, and make the most of the decades ahead.

Connect with Joy Levin:

• LinkedIn: Joy Levin

• Website: Gen X Exec Encore