The Corporate Escapee

If you know corporate is broken but jumping straight into solopreneur life feels like too big a leap, this episode is for you.Brett breaks down how to treat your “escape plan” like an insurance policy—not a dramatic leap off a cliff. You don’t have to quit your job tomorrow. But you do owe it to yourself to be prepared for the moment corporate quits on you… or you finally hit your breaking point.Instead of trying to convince you to go all-in on a solo business, this episode walks you through how to build a plan you can keep in your back pocket—so you’re not starting from zero if things go sideways.Download the FREE Starter KitJoin the CollectiveIn this episode, you’ll learn:Why the gap is so big between people who know corporate is broken and those who actually take actionHow to think like a “prepper” (without going full doomsday): planning so you don’t have to plan in the middle of chaosStep 1 – Define what you actually wantStep 2 – Get clear on your financial realityStep 3 – Take inventory of your skills and energyStep 4 – Shift from job title to problem-solvingStep 5 – Reframe your current employer as just one clientAlso: • A simple formula to value your time • Annual salary × 1.25, then drop three zeros → a shockingly accurate baseline hourly rate •. Why many escapees replace their corporate income in ~20–25 hours per week • Why you don’t need 100 customers • How 2–5 good clients can replace (or exceed) your corporate pay • Why most of those opportunities will come from networking and referrals, not job boardsWho this episode is forYou’re still in corporate, you know the system isn’t built for you, but you don’t see a clear path outYou feel stuck between “I hate this” and “I don’t know what else I’d do”You’re curious about going solo, but the idea of just quitting and “figuring it out” feels recklessYou want a practical, low-risk way to prepare now, so you’re not scrambling later

If you’ve ever walked out of a meeting thinking, “Why didn’t that land?”Or if you’ve ever felt invisible in corporate…Or if you’re building a life outside of corporate and wondering why some conversations connect and others fall flat…This episode will hit you hard.Today, Brett welcomes back Jake Stahl — author of the brand-new book Own the Room and creator of the STRATA framework, a system for reading people, decoding signals, and communicating with true presence instead of performance.Twelve years ago, Jake lost everything to opioid addiction — his marriage, his home, his reputation, and the identity he’d spent decades building. But his path back didn’t begin with a new job or a second chance.It began with learning how to read people.Jake realized that most communication has nothing to do with the words being spoken. It’s the signals beneath them — the micro-expressions, the posture shifts, the emotional triggers — that determine whether someone trusts you, connects with you, or shuts down entirely.Today, Jake breaks down STRATA, the six-part framework you can use to own every room you enter: • Signal: What you broadcast before you say a word • Trigger: The moment resistance appears • Reframe: How you shift someone’s lens without force • Anchor: Making the insight stick • Transfer: Turning your idea into their idea • Action: Where the next step becomes inevitableWe talk about how STRATA applies to sales, relationships, leadership, marriage, friendships — and most importantly, the escapee journey. Because leaving corporate and building your own path requires one core skill:👉 You must connect with people in a way that feels real.This episode gives you the playbook.Connect with Jake Stahl • LinkedIn: https://www.linkedin.com/in/jakestahl/ • TikTok: @JakeTheMindMechanic • Podcast: https://thejakestahl.com/podcast/ • Book: Own the Room: https://thejakestahl.com/books/

What happens when corporate stress gets so bad you literally can’t swallow solid food?That’s where Claire Sullivan found herself.On December 1st, 2023, corporate quit on her — and she took what most people would call the riskiest step possible:She built a business… the same day.Filed an LLCRegistered everything needed to operatePosted on LinkedIn that she was going out on her ownListened to what the market actually wantedAnd replaced her former salary by the end of the weekIs that typical? No.Is it possible? Absolutely.And more importantly — the steps she took are repeatable for anyone stuck in a corporate job that no longer works for them.This is one of the most real and honest conversations we’ve had on what it actually looks like to escape corporate — emotionally, financially, mentally, and practically.Who This Episode Is ForThis one is for you if:Corporate has stopped making senseEvery job application feels like it goes into a black holeYou’re burned out but can’t “just quit”You want control over your time, income, and healthYou don’t think you have “enough” experience to go out on your ownYou just need one real example of someone who actually did itConnect with ClaireMaven Course: How to Layoff-Proof Your Career by Becoming a Solopreneur: https://maven.com/clair-sullivan-associates/launch-your-solopreneur-business?promoCode=ESCAPELinkedIn: https://www.linkedin.com/in/dr-clair-sullivan/

Freebie from Michael: 20% off: https://www.clym.io/p/bretttrainor Most solo businesses are focused on getting clients—but ignore the compliance risks that can quietly wreck everything.Former tax attorney and CFO Michael Williams joins Brett to break down the ADA, privacy, and regulatory issues small businesses face—and how a $100K GDPR mistake pushed him to finally build Clym.io, an all-in-one website compliance platform.Michael also shares the remarkable story of raising a seven-figure VC round… then paying it back to regain control and stay true to his vision.In This Episode:• The hidden ADA & privacy risks solopreneurs overlook• Why most accessibility lawsuits hit small businesses• How AI-powered scans fuel compliance lawsuits• How Clym.io uses one snippet to manage 150+ regulations• Why Michael left a cushy CFO role at 38• The identity shift from employee → builder• What it’s really like to take VC money—then give it back• Why taking action beats waiting for the “right” timeConnect with Michael & ClymWebsite: https://clym.ioMore From BrettEscapee Starter Kit, resources & links → https://linktr.ee/bretttrainor

This episode is a little different. I was a guest on Catherine Jelinek’s podcast, Breaking Through the Noise — and she generously allowed me to share the full conversation with you.We talk about leaving corporate, taking action, finding traction on TikTok, and the honest story behind building the Corporate Escapee movement. If you’re stuck, burned out, or thinking about going solo, this one will hit home.In this episode, we cover:Why taking action is the #1 skill corporate trains out of youMy path from 25 years in corporate → consulting → fractional → building 10+ income streamsHow TikTok unexpectedly became the platform that changed everythingWhy 80% of my 76K TikTok followers are over 40The moment one video brought in 300+ strategy call requests in 48 hoursThe three stages of an escapee: Curious, Motivated, and LiberatedWhy your path out of corporate isn’t a leap — it’s a shiftThe reality of layoffs, RTO mandates, and the “profits over people” eraWhy authenticity beats production quality every timeThe mindset shift corporate doesn’t prepare you forWhy this conversation mattersA lot of people want out of corporate, but they overthink the first step. This episode breaks down what actually works — and why you already have more than enough experience to start.Connect With CatherineCheck out Catherine Jelinek’s podcast:👉 Breaking Through the NoiseAvailable on Apple, Spotify, and YouTube. Follow and support her work — she’s having the conversations corporate workers need to hear.

Today I’m joined by Neil K. Carroll, founder of vidwheel, who took the long way out of corporate: video agency → higher-ed job → rebuilding as a lean solo business.Neil shares how a simple testimonial project for a startup turned into something much bigger—a repeatable, productized service that helps founders uncover the stories and insights hidden inside their customer relationships.If you’re stuck in corporate and wondering what you would even sell, this episode will help you see the path: start with what you already know, listen for the real problem, and bet on yourself.What You’ll LearnNeil’s escape path: agency burnout → COVID pivots → higher-ed → soloThe “Root Thread” deep testimonial approach and why it delivers strategic customer insightHow to productize what you already do without boxing yourself inWhy referrals and local networks are enough for a one-person businessHow Neil priced his offer and why undercharging early is part of the processThe 4 levers every offer should hit: save time, save money, make money, reduce riskWhy betting on yourself beats betting on corporate stabilityKey TakeawaysYour corporate title doesn’t matter—your ability to solve problems doesProductized services make selling and delivery easierCustomer conversations reveal the real value you offerSolopreneurs don’t need 100 clients—you need a few right-fit onesYou can always go back to corporate… but very few people want to once they leaveAbout Neil K. CarrollNeil is the founder of vidwheel, helping startups and small businesses capture deep customer stories through Root Thread testimonial interviews and his hardware-enabled Mini Studio (VidKit 3).He combines interviewing skill, remote production, and AI-assisted analysis to help companies extract messaging, proof, and product insight directly from their customers.Connect with Neil:LinkedIn: Neil K. CarrollWebsite: vidwheel.com

Download the FREE Escapee Starter KitEpisode SummaryAfter nearly 30 years in corporate communications, Ed Patterson didn’t just leave corporate—he left the country. He and his partner planned their move to Portugal, secured residency, and designed a new life where work no longer sits at the center. We cover what it really takes to prepare (financial, legal, lifestyle), what he’d do sooner, how he reframed success to “quality of my day,” and practical advice for anyone considering a similar shift—whether you move abroad or simply want more control at home.Chapter markers • 00:00 Intro: Why Ed left corporate and the U.S. • 00:45 Ed’s background: PR/Comms, crisis, agency + in-house • 03:00 The Portugal plan: residency, D7 visa, timelines, consultants • 05:35 How they prepared: roles, finances, finish lines, advisor sign-off • 10:50 Healthcare and costs: private insurance, day-to-day expenses • 14:40 Redefining happiness: “quality of my day,” health, sleep, energy • 20:13 Advice to 30- and 40-somethings: plan for when you want to—and when you have to • 26:14 Do an inventory: skills, network, gaps, use corporate to upskill • 30:11 Action over waiting: fractional, contracts, bridge income • 33:06 The “adventure years” mindset and inviting questions • 35:23 CloseKey takeawaysPlan with intent: set a finish line, pressure-test with a financial advisor, and define roles at home.Consider geo-arbitrage: lower costs can pull your finish line forward by years.Optimize your day: sleep, movement, and mental space beat title-chasing.Treat corporate like your one client: extract skills, network, and education while you’re there.Build optionality: fractional work and short contracts can bridge income during transitions.Do the inventory: skills, network, marketable experiences, and gaps to close before you jump.Prepare for both scenarios: when you choose to leave—and if corporate chooses for you.Health matters: design a life you can actually enjoy.GuestEd Patterson:LinkedIn: https://www.linkedin.com/in/edpatterson1/Instagram: https://www.instagram.com/twoguysinportugal Callout quotes“We hit our finish line sooner because our costs dropped by a third to a half.”“I sleep better, eat better, and feel more creative. That was impossible when work ran my day.”“Plan for your choice—and for the day you may not have one.”

Guest: Bob Burg, co-author of The Go-GiverNote 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.What You’ll Learn: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 LearnWho 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.Timestamps00:00 Welcome & why healthcare keeps people stuck02:00 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 premiums15:00 Getting a quote in minutes; three plan designs; preventive care at 100%18:45 Networks (MultiPlan/PHCS), open access, prior auth for big bills21:00 White-glove support & Trustpilot traction22:45 Who it’s not for (questionnaire fails; ACA may be better)24:30 Simplicity: deductible = out-of-pocket; families cap at 2x deductible25:40 Future: biomarkers program, better health → better rates30:30 Policy watch: portable benefits & association health plans34:30 Final advice: know all your options; compare total cost & designAbout Our GuestTom 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.DisclaimerThis 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 happinessIf 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 SolopreneurConnect 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 offersWhy augmentation beats automation for consultants, advisors, and fractionalsHow to sell outcomes, not titles — and why buyers care more about value than everWhy your corporate scars, empathy, and critical thinking are your new superpowersIf 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.GuestMichael 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 EscapeesGrab 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 connectIf this episode hit homeShare 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 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 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 youThis 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/thecorporateescapeeJoin 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 ROIKey Moments:00:00 – Welcome back and recap of Paul’s first appearance02:00 – Why medical professionals are escaping corporate medicine09:00 – The Ignorance Tax and when to hire help10:30 – The best automation and CRM tools for solos20:00 – ADA tax credit: how it works and why it matters28:00 – How small, AI-enabled teams are outpacing big companies35:00 – The mindset shift from worker bee to queen bee39:00 – Continued learning, avoiding the comfort trap, and staying curious41:00 – Where to connect with Paul and learn moreResources Mentioned:• Paul Durelli – Digital Kahuna: www.digitalkahuna.com• CRM Tool – Go High Level• Book – “Pro Voice” by JT O’DonnellConnect 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 escapeesTimestamps00:00 – Why this convo is different01:20 – Lisa’s corporate path → calling05:40 – Awakening without the woo10:40 – Choice vs. reaction in corporate (and life)12:40 – Reframing uncertainty & fear16:10 – What corporate gives you—and when it plateaus20:25 – Purpose, practically: defining mission without dogma26:50 – Starter steps if you’re stuck (clarity, script, small bets)30:10 – Why Lisa’s book is free + how to use it35:10 – Frameworks beat retreats (avoid meandering)36:45 – Wrap + where to connectLinks & resources • Free book: Life Quest: Your Role in Saving the World: https://lisapetrilli.com/ • Connect with Lisa: https://www.linkedin.com/in/lisapetrilli/ About LisaLisa 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.GuestRobert Lock — Founder, Buffalo Mountain Sales Strategies | Advisor with Sales Acceleration | Based in Denver, COConnect on LinkedIn: https://www.linkedin.com/in/lockrobert/ KeywordsGenX • 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 TourThis 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 needsFor 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 pathHow he walked on to Iowa State’s Top 25 basketball program after not playing for 3 yearsHis role as the team’s “Chief Energy Officer” and how he brought discipline and heart into everything he didHow struggle, loneliness, and discomfort became the fuel for transformationThe importance of self-awareness, emotional honesty, and earning your identityWhy he’s building a speaking career focused on pouring into others—and how that fills him with purposeHow 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 TakeawaysGenX 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 NaveenMemorable 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 mostThe three categories every escapee needs: prospects, clients, and connectorsHow to re-engage dormant ties for new opportunitiesThe “14 interactions” rule and why most people quit too soonWhy doing structured free work can accelerate your first paying clientsHow GenXers’ natural problem-solving and “be helpful” mindset is a superpower in building trustWhy confidence isn’t faked—it grows naturally from following a consistent systemAbout David AckertDavid 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 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. 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 driverTom 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 freedomConnect 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” planIf 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