Guest: Bob Burg, co-author of The Go-Giver

Note from Brett:

This Greatest Hits episode is one of the most shared conversations we’ve ever had — and for good reason. If you’re trying to land your first clients or grow your solo business, Bob’s Go-Giver principles are a masterclass in creating value, building trust, and turning relationships into revenue.

I wanted to bring this one back for our thousands of new listeners. There is so much value to be learned from Bob and a core to solopreneur success.

Listen for three big takeaways:

👉 How to define value vs. price and articulate your worth.

👉 How to make referrals your #1 growth engine.

👉 Why receiving is just as important as giving.

• The difference between price and value — and why focusing on value creates loyal clients.
• The Law of Compensation: your income equals how many people you serve × how well you serve them.
• Why authenticity and consistency inspire trust.
• How to stay open to receiving so opportunities can flow back your way.
• Simple frameworks for building a referral flywheel that compounds over time.

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, but… benefits,” this is your episode.

Links:

• Solo Health Collective: https://hbgsolo.com/
• Tom Morrissey LinkedIn: https://www.linkedin.com/in/tommorrisseyhbg/

What You’ll Learn

• Who qualifies & how it works: EIN required, brief medical history, plan in your business’s name (self-insured structure for solos).
• How it’s different: Not ACA and not a sharing ministry; three high-deductible options ($2.5K / $5K / $10K) with 100% coverage after the deductible and no annual/lifetime max.
• Network & Rx: Open network with MultiPlan/PHCS PPO; pharmacy via Pharos Rx; prior auth for big procedures.
• Costs & fit: Age-rated pricing—often competitive vs. ACA when you compare total cost + design—but not for everyone (medical questionnaire matters).
• Service that doesn’t stink: Human, concierge-style support (aka you can talk to a person).
• The road ahead: Optional “Solo-Plus” wellness track (full lab panels 2x/year) to drive better health and better underwriting; watch items like portable benefits and association health plans that could expand options for independents.

Timestamps

00:00 Welcome & why healthcare keeps people stuck

02:00 What Solo Health Collective is (and isn’t)

04:00 Tom’s background (Cigna → self-insured solutions for small employers → solos)

07:30 Why underwrite the business of one (EIN)

10:30 The cost problem (everywhere) & what drives premiums

15:00 Getting a quote in minutes; three plan designs; preventive care at 100%

18:45 Networks (MultiPlan/PHCS), open access, prior auth for big bills

21:00 White-glove support & Trustpilot traction

22:45 Who it’s not for (questionnaire fails; ACA may be better)

24:30 Simplicity: deductible = out-of-pocket; families cap at 2x deductible

25:40 Future: biomarkers program, better health → better rates

30:30 Policy watch: portable benefits & association health plans

34:30 Final advice: know all your options; compare total cost & design

About Our Guest

Tom Morrissey is a benefits industry veteran (40+ years) and co-builder of Solo Health Collective, a national health plan purpose-built for self-employed business owners with no W-2 employees. Previously with Cigna serving mid-market and national accounts, Tom now focuses on accessible, concierge-level benefits for one-person companies.

Disclaimer

This episode is for educational purposes only and is not insurance, legal, or financial advice. Compare options (ACA, off-exchange, group, and Solo Health Collective) and choose what fits your situation.

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

🎧 Subscribe to The Corporate Escapee Podcast

📩 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:

• How to blend AI with your experience to create faster, smarter offers
• Why augmentation beats automation for consultants, advisors, and fractionals
• How to sell outcomes, not titles — and why buyers care more about value than ever
• Why your corporate scars, empathy, and critical thinking are your new superpowers

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

• Grab the Escapee Starter Kit: https://stan.store/thecorporateescapee 
• Join Escapee Collective Plus: https://escapee-collective.circle.so/checkout/escapee-plus-subscriptions 

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:

• Download the free Escapee Starter Kit – https://stan.store/thecorporateescapee
• Join the Escapee Collective ($20/mo for life before Dec): https://escapee-collective.circle.so/checkout/escapee-plus-subscriptions 
• Connect with Brett on LinkedIn: https://www.linkedin.com/in/bretttrainor/
• Email: [email protected]

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 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.