Brett Trainor Unplugged

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 what sustainability really means—financially, mentally, and emotionally—for Gen Xers who’ve left corporate (or are ready to).

They dive into:

✅ The “three-to-four-year wall” most solopreneurs hit—and how to move past it

✅ Building multiple revenue streams without chaos

✅ Shifting from survival mode to intentional growth

✅ Why sharing your numbers builds trust (and confidence)

✅ How to measure success beyond money—using purpose, time, and happiness

If you’ve escaped corporate or are thinking about it, this conversation is your roadmap for building a business—and a life—you actually want to sustain.

Connect with Jenni Gritters

📘 The Sustainable Solopreneur 

🌐 jennigritters.com

💌 Newsletter: The Sustainable Solopreneur

Connect with Brett Trainor

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📩 Download the FREE Escapee Starter Kit

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 combining AI efficiency with human judgment, creativity, and experience — proving that the GenX advantage lies in knowing how to apply wisdom to new tools.

You’ll learn:

If you’re a GenX pro still in corporate (or newly escaped), this conversation will show you how to use AI to amplify your expertise — not replace it.

Guest

Michael Himmelfarb — Pricing & product marketing strategist helping companies modernize pricing/packaging with AI-augmented consulting. Connect on LinkedIn and mention this episode for his 48-hour sprint details.

LinkedIn: https://www.linkedin.com/in/michaelhimmelfarb/

Resources mentioned

• Anthropic’s “automation vs. augmentation” idea (discussion)

• Shout-out: Naveen Aggarwal (technical enablement/automation support)

For GenX Escapees

Chapters

• 00:00 Welcome back, OG Escapee + today’s focus

• 01:29 From fractional CMO to pricing & packaging specialization

• 03:53 The buyer shift: clarity, speed, and specific problems

• 04:22 The 20/80 idea: what humans do that AI can’t

• 07:40 Automation vs. augmentation (and why it matters)

• 10:33 Hybrid delivery: standardized outputs + human judgment

• 12:25 Human superpowers: creativity, prediction, empathy

• 14:09 Beyond pricing: applying the model across functions

• 15:45 Productized sprints → recurring revenue possibilities

• 17:23 Big-firm disruption and the GenX advantage

• 19:33 Learning curves, iteration, and avoiding “prompt pack” hype

• 26:13 Focus, trade-offs, and building a simple offer

• 30:28 Shout-outs & resources + workshop idea

• 31:30 Michael’s ask + how to connect

If this episode hit home

Share it with a fellow GenX pro, leave a quick review, and DM Brett if you want the link to the free Starter Kit PDF or details on Michael’s sprint.

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 outside trying to replace your income, this episode is the playbook. From fractional and advisory work to user-generated content, workshops, and buying a small business — Brett shares what’s working, what he’s tried himself, and what might fit your life right now.

You’ll hear:

• Why your experience is more valuable outside of corporate than inside

• 17 proven ways (and 2 bonus paths) to monetize what you already know

• How GenXers are replacing their corporate income in ~25 hours a week

• The difference between consulting, fractional, advisory, and coaching

• Why “monthly service packages” might be the fastest on-ramp for freedom

• Real examples from Brett’s own journey — what worked and what didn’t

• How to future-proof your income before corporate “quits” on you

This one’s packed with ideas you can start exploring right now — no fancy website, no new degree, and definitely no corporate BS.

Mentioned paths include:

Solo Consulting • Fractional Leadership • Interim Roles • Advisory • Coaching • Business Development & Affiliate Deals • Services / Subscriptions • Paid Communities • Sponsorships • Influencer & Content Partnerships • Workshops • Speaking • User-Generated Content (UGC) • E-Commerce • Tech-Enabled Services • Plus: Buying a Business & Franchises (the two “bonus” options)

If this hit home, follow the show so you don’t miss the next “CliffsNotes” drop.

👉 Want help figuring out your best path out of corporate?

Join the Escapee Collective for $20/month (locked for life if you join before December) and connect with other GenXers building freedom on their own terms.

🔗 Links in the notes:

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 of healthcare and build profitable, flexible practices in functional medicine.

They cover why every solo business owner eventually pays an “Ignorance Tax,” how to turn that into an automation advantage, and why building your digital backbone early—CRM, SMS, AI follow-ups—can save years of frustration. Paul also shares a powerful “found money” idea: adding an ADA accessibility widget to your site that qualifies you for a $5,000 federal tax credit every year.

What You’ll Learn:

• The Ignorance Tax: when to stop DIY-ing and pay for speed and expertise

• The tech stack every solo business needs to scale (CRM, SMS, email, AI)

• How to delegate effectively and build your first small remote team

• Lessons from doctors escaping into functional medicine and how that model applies to corporate escapees

• How to find “found money” opportunities like the ADA tax credit that deliver instant ROI

Key Moments:

00:00 – Welcome back and recap of Paul’s first appearance

02:00 – Why medical professionals are escaping corporate medicine

09:00 – The Ignorance Tax and when to hire help

10:30 – The best automation and CRM tools for solos

20:00 – ADA tax credit: how it works and why it matters

28:00 – How small, AI-enabled teams are outpacing big companies

35:00 – The mindset shift from worker bee to queen bee

39:00 – Continued learning, avoiding the comfort trap, and staying curious

41:00 – Where to connect with Paul and learn more

Resources Mentioned:

• Paul Durelli – Digital Kahuna: www.digitalkahuna.com

• CRM Tool – Go High Level

• Book – “Pro Voice” by JT O’Donnell

Connect with Paul:

Visit www.digitalkahuna.com for courses, automation services, and details on the ADA $5,000 tax credit offer.

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 spot yours

• How to move from reaction and fear to sovereignty and action

• A 30–60 day Next-Chapter Script exercise to regain control

• Why love-over-fear is a leadership OS (not a sermon)

• First small steps for still-in-corporate escapees

Timestamps

00:00 – Why this convo is different

01:20 – Lisa’s corporate path → calling

05:40 – Awakening without the woo

10:40 – Choice vs. reaction in corporate (and life)

12:40 – Reframing uncertainty & fear

16:10 – What corporate gives you—and when it plateaus

20:25 – Purpose, practically: defining mission without dogma

26:50 – Starter steps if you’re stuck (clarity, script, small bets)

30:10 – Why Lisa’s book is free + how to use it

35:10 – Frameworks beat retreats (avoid meandering)

36:45 – Wrap + where to connect

Links & resources

• Free book: Life Quest: Your Role in Saving the World: https://lisapetrilli.com/

• Connect with Lisa: https://www.linkedin.com/in/lisapetrilli/

 About Lisa

Lisa Petrilli is the founder/CEO of Higher Conscious Leadership and a former corporate exec (Medline, Baxter). She helps leaders move from mind/body mastery to soul-level purpose and practical action.

CTA (one small step)

Download the free book, then spend 10 minutes today writing your 30-day script. Prompt: “If nothing at work changed, how would I live the next 30 days differently?”

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 every chat with 2–3 new intros

💡 Why owner conversations are precious—and how to uncover real problems instead of pitching surface ones.

💡 How to package your offer with paid discovery + 90-day sprints instead of scary year-long scopes.

💡 Why going local first builds faster trust (and how that expands nationally).

💡 How adding exit-planning expertise creates credibility and future opportunities.

Guest

Robert Lock — Founder, Buffalo Mountain Sales Strategies | Advisor with Sales Acceleration | Based in Denver, CO

Connect on LinkedIn: https://www.linkedin.com/in/lockrobert/

Keywords

GenX • Corporate Escape • Solo Consulting • Fractional Leadership • SMB Sales • Discovery Calls • Networking • Sales Acceleration • Denver

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 This Episode Matters for GenXers:

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

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)

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:

Enjoy and let us know what you think!