The Corporate Escapee

Tom Mirabella left corporate at 30 and never looked back. Seventeen years later, he’s built Wingman into a 25-person business by doing what corporate rarely rewards: solving problems fast, betting on relationships, and staying obsessively close to customers.In this conversation, Tom breaks down his escape story, why “local + in-person” is making a comeback, and how Wingman’s franchise model flips the typical franchise script — where the franchisee focuses on relationships and sales while the central team handles fulfillment and delivery.If you’re stuck in corporate and can’t see a path out, this episode gives you a practical look at what “building your own lane” can really look like — without pretending it’s easy.Join the Escapee Collective: TheEscapeeCollective.com What You’ll Learn• Why Tom left corporate early (and what corporate policies taught him about ceilings)• The side-hustle-to-business path: how one small project turned into real clients• How to think about risk when leaving: your monthly “number” vs. replacing a salary• Why entrepreneurship can swing from best day to worst day in 30 minutes — and how to handle it• The “digital mayor” concept: becoming the trusted local hub in your town• Why Tom believes physical locations + community presence still win in a digital world• A modern franchise approach: franchisee sells + builds relationships, HQ team delivers• Why customer service and trust are the real differentiators in crowded marketsKey Quotes• “The problem’s now. Two weeks from now, it’s worse.”• “As an entrepreneur, you can have the best and worst day within a half hour.”• “I want you to be the digital mayor of your town.”• “If you do what you love, the money follows.”Mentioned in This Episode• COBRA and how Tom thought about early-stage risk• Networking groups, chambers, community events, and “planting seeds”• Using a podcast as a lead generator (and why it worked)Connect with Tom• Email: Tom at wingmanplanning.com• Website: WingmanPlanning.com• Social: Instagram / Facebook / TikTok / LinkedIn (search “Wingman Planning”)

What if scaling your business didn’t require hiring, hustling harder, or stacking endless clients?In this episode, Brett sits down with Pia Silva (No BS Mastery) to break down a simple model for building a highly profitable solo (or two-person) business — built around intensives, clear boundaries, and pricing for outcomes (not hours).Pia shares how she and her husband went from $40K in debt to $500K in revenue by shifting from long, drawn-out projects to a focused, high-value intensive model. Then she explains her signature framework — the 50-25-25 Rule — and how to reverse-engineer your pricing based on the life you actually want.If you’re a corporate escapee (or future one) trying to make real money without recreating the corporate grind… this is the blueprint.Join the Escapee Collective!What you’ll learn • Why most “big ticket” projects are often the least profitable • Pia’s 50-25-25 Rule for profit + freedom (and how to use it to price your offers) • How to design offers so you make your monthly revenue in 50% of your client hours • The two levers to grow profit without working more: • Increase value (real + perceived) • Decrease time (intensify delivery) • A smarter version of “good / better / best” packaging (without selling deliverables) • How to use a Lead Product (paid) instead of free proposals to build trust fast • Why warm networks beat websites and content in the early stages • How to build boundaries that prevent scope creep (without sounding rigid) • The mindset shift escapees must make: sell outcomes, not timeKey frameworks + concepts mentioned • The Intensives Model: Focused delivery in a compressed timeframe vs. dragging projects out for months • 50-25-25 Rule: Make your total revenue in 50% (or less) of your client-working hours so you have time for life • Lead Product Method: A paid diagnostic/strategy step that replaces proposals and tees up an easy upsell • Boundaries via Process: Clear steps + expectations reduce pushback and scope creepResources from Pia • Scale Solo Playbook: NoBSMastery.com/playbook • Price to Freedom CalculatorConnect with Pia • Instagram: @pialovesyourbiz • LinkedIn: Pia Silva

Why do so many people leave corporate… only to end up going back?In this solo episode, Brett breaks down the two core reasons most corporate escapees fail—and more importantly, how to avoid them.Failure here doesn’t mean experimenting and choosing corporate again. It means wanting out, trying to go solo, and giving up before momentum ever takes hold.If you’re thinking about leaving corporate—or you’ve already made the leap—this episode will help you understand what really trips people up and how to build a path that actually sticks.Resources Mentioned The Escapee Collective – A milestone-based community designed to help corporate escapees get out and stay out: Link: https://escapee-collective.circle.so/checkout/the-escapee-collective What You’ll Learn in This Episode • Why not getting an early win is the fastest way to lose confidence • How long gaps without income create doubt, panic, and backtracking • Why most escapees don’t lack skills—they lack momentum • The hidden cost of isolation and loneliness when you go solo • Why “doing it alone” dramatically increases emotional swings • How peer support and feedback shorten the learning curve • Why community works better when people are at similar stages • The difference between education, theory, and applied learning • What successful long-term escapees all have in commonKey TakeawayGoing solo doesn’t fail because you’re not smart enough or experienced enough.It fails when: • You don’t get a win early • You try to figure everything out aloneMomentum and connection matter more than perfection.Resources Mentioned The Escapee Collective – A milestone-based community designed to help corporate escapees get out and stay out: Link: https://escapee-collective.circle.so/checkout/the-escapee-collective You can also reach out directly to Brett on LinkedIn with questions about the community or your escape path.

What if podcasting wasn’t just content—but a bridge out of corporate?In this episode, Brett sits down with Mark Hayward, former PwC and KPMG consultant turned podcast host and podcast guesting entrepreneur, to break down his escape from corporate—and how podcasting quietly became one of his most powerful tools.Mark shares how he started a podcast while still in corporate, not to make money, but to build confidence, find his voice, and explore what life outside the corporate box could look like. That passion project eventually opened doors to consulting, coaching, real estate experimentation—and ultimately a business built around helping others grow through podcast guesting.This is a real, honest conversation about experimentation, false starts, energy, and why podcasting works differently than most people expect.What We Cover • Leaving PwC and KPMG after a 14-year corporate career • Why Mark started a podcast before leaving corporate • The role experimentation plays in finding your escape path • Why not every revenue stream is worth keeping • Coaching vs. consulting vs. creative work (and the energy test) • Podcast hosting vs. podcast guesting — and how each actually works • Why guests often get more business than hosts • How podcasting builds confidence, clarity, and opportunity • Practical advice for corporate professionals who know they want out—but don’t know what’s nextKey TakeawayYou don’t need a perfect plan to escape corporate. You need momentum, experimentation, and a way to get into conversations that open doors. Podcasting can be one of those doors.Connect with Mark • Website: podcastintroduction.com • Podcast: Business Growth Talks • LinkedIn: https://www.linkedin.com/in/mark-hayward-163721a0/ Listen, subscribe, and shareIf corporate feels off—but you can’t see the exit yet—this episode will help you think differently about your options.

If you know corporate isn’t for you but you can’t see a clean exit, this episode is your roadmap. Brett sits down with Sam Lee (Indie Collective) to break down how experienced professionals can build a “portfolio career” — consulting, coaching, fractional work, and productized services — without quitting their full-time job first. Sam shares the simple frameworks that helped him build $1M+ in annual revenue through independent work for over a decade, and he explains why most people get stuck trading time for money. You’ll walk away with a practical way to tell your story, activate your network, and design an exit strategy with less risk.In this episode, you’ll learn: • Why the “side hustle first” approach builds confidence and reduces risk • The simple sales story that unlocks referrals: Client → Problem → Outcome • How to activate your network without sounding awkward or salesy • Why “fractional” isn’t always the fastest path to revenue — and what is • The real goal: stop trading time for money and start selling outcomes • Sam’s 3-part productization path: 1. Niche down to best-fit clients 2. Solve painkiller problems (not vitamins) 3. Build a portfolio of offers, including productized work • The two killers of the independent path: no early wins + isolation • Why productizing your expertise helps both client work and job searchesKey quotes / soundbites: • “The most pernicious trade independent builders make is trading time for money.” • “Your sales story is three things: who you serve, their problem, and the outcome.” • “Nobody is hiring a generalist right now. They want been-there-done-that experts.” • “Trial and error at this stage of your career is expensive.”Resources mentioned: • Indie Collective: IndieCollective.co

Get the New Escapee Starter Kit HereIf you know corporate is broken—but you’re not ready to quit—this episode is for you.In this year-end solo episode, Brett walks through 7 practical steps to help you rethink your relationship with work, assess how happy you actually are, and explore whether there’s a path outside corporate—without making a risky leap.This isn’t about quitting your job.It’s about getting prepared, taking back control, and testing what’s possible using the experience you already have.Whether you’re 25 or 65, this episode helps you stop being reactionary and start designing what comes next.What You’ll LearnWhy most people stay stuck—even when they’re miserableHow to reframe yourself from “employee” to “business owner”The 5-factor scorecard to measure your real happinessWhy you’re already a solopreneur with one bad clientHow to inventory your skills without thinking in job titlesA simple way to calculate your real market valueHow to design a future that integrates work into your life—not the other way aroundThe 7 Steps Covered in This EpisodeReframe Your Reality – You don’t need new skills or a new degreeEstablish Your Happiness Baseline – Money isn’t the whole storySee Yourself as a Solopreneur – You already have one client (corporate)Define What You Really Want and Need – Financially, personally, realisticallyTake Inventory of Your Skills and Energy – Focus on problems you like solvingCalculate Your Value – A simple formula to find your hourly baselineDesign Your Ideal Future – Work backward from the life you wantKey TakeawaysIt’s easier to find your first customer than your next jobSmall wins build confidence faster than big, risky betsYou don’t need permission to start testing a new pathDone is better than perfectControl comes from action, not planningFinal ThoughtYou don’t have to leave corporate to take back control.But if you don’t start preparing, another year will pass—and you’ll be having the same conversation...

This episode is a live mini-workshop recorded with members of the Escapee Collective (and released here because it was too useful to keep inside the community).My guest Diane Kennedy (CPA) breaks down what most new escapees get wrong about taxes and business structure — and why the real first question isn’t “LLC or S-Corp?”It’s: Are you building a business… or replacing a paycheck?From there, we get into the most common setup for solopreneurs (LLC + S-Corp election), how to think about deductions without getting cute, and why “keeping it small and keeping it all” is the solopreneur cheat code.We also bring in Lisa Dini from Lettuce, who explains how they help solos run the S-Corp model without turning you into an accountant.Heads up: This is educational, not legal/tax advice. Talk to your pro for your situation.What you’ll learnThe real first question for escapees: build a business vs replace a paycheckWhy “LLC vs S-Corp” is usually the wrong framing (and what Diane recommends instead)Why Diane believes you should set up an LLC early (asset protection + flexibility)The 3 “buckets” of income for solopreneurs: Earned, Leveraged, & Passive (the holy grail)A simple way to think about deductions: ordinary + necessary (and how to find write-offs you already have)How S-Corps can help you keep more of what you earn (salary vs distributions, plus other benefits discussed)Real-world Q&A on: partners, joint ventures, and multi-state setups, California “special rules” , Schedule C vs S-Corp timing, Solo 401(k) and related retirement ideasResources Mentioned:Lettuce.co: https://hubs.ly/Q03Yz8KX0Tax Calc: https://hubs.ly/Q03Yz8Rf0Tax Prep: https://hubs.ly/Q03Yz8JY0GuestsDiane KennedyCPA and long-time solopreneur. Diane helps business owners structure their business and income in smarter ways so they can keep more of what they earn and operate like a real business.Lisa Dini (Lettuce)Lettuce helps solopreneurs run an S-Corp model efficiently, without drowning in admin and accounting work.

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: bt@bretttrainor.com

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.