Brett Trainor Unplugged

By Brett TrainorBusiness Entrepreneurship Education Self-Improvement

Brett Trainor Unplugged episodes

December 19, 2025Keep It Small. Keep It All. (Live Workshop on Escapee Taxes + Business Setup)
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 learn
The real first question for escapees: build a business vs replace a paycheck
Why “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 ideas

Resources Mentioned:

Lettuce.co: https://hubs.ly/Q03Yz8KX0

Tax Calc: https://hubs.ly/Q03Yz8Rf0

Tax Prep: https://hubs.ly/Q03Yz8JY0

Guests

Diane Kennedy

CPA 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.
41 min
December 09, 2025Your Corporate Escape Plan: Insurance Policy, Not Leap of Faith
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 Kit

Join the Collective

In this episode, you’ll learn:
Why the gap is so big between people who know corporate is broken and those who actually take action
How to think like a “prepper” (without going full doomsday): planning so you don’t have to plan in the middle of chaos
Step 1 – Define what you actually want

Step 2 – Get clear on your financial reality

Step 3 – Take inventory of your skills and energy

Step 4 – Shift from job title to problem-solving

Step 5 – Reframe your current employer as just one client

Also:

• 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 boards

Who this episode is for
You’re still in corporate, you know the system isn’t built for you, but you don’t see a clear path out
You 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 reckless
You want a practical, low-risk way to prepare now, so you’re not scrambling later
23 min
December 05, 2025 Own the Room: How to Communicate So You’re Heard, Seen & Respected w/ Jake Stahl
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 inevitable

We 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/
44 min
November 27, 2025Corporate Quit on Her — She Built a Business Faster Than She Could Job Hunt w/ Clair Sullivan
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 LLC
Registered everything needed to operate
Posted on LinkedIn that she was going out on her own
Listened to what the market actually wanted
And replaced her former salary by the end of the week
Is 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 For

This one is for you if:
Corporate has stopped making sense
Every job application feels like it goes into a black hole
You’re burned out but can’t “just quit”
You want control over your time, income, and health
You don’t think you have “enough” experience to go out on your own
You just need one real example of someone who actually did it

Connect with Claire

Maven Course: How to Layoff-Proof Your Career by Becoming a Solopreneur: https://maven.com/clair-sullivan-associates/launch-your-solopreneur-business?promoCode=ESCAPE

LinkedIn: https://www.linkedin.com/in/dr-clair-sullivan/
38 min
November 22, 2025 He Left a Cushy CFO Job to Fix a Broken System (with Clym.io Founder Michael Williams)
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” time

Connect with Michael & Clym

Website: https://clym.io

More From Brett

Escapee Starter Kit, resources & links → https://linktr.ee/bretttrainor
41 min
November 20, 2025How One TikTok Video Built the Corporate Escapee Movement
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 you
My path from 25 years in corporate → consulting → fractional → building 10+ income streams
How TikTok unexpectedly became the platform that changed everything
Why 80% of my 76K TikTok followers are over 40
The moment one video brought in 300+ strategy call requests in 48 hours
The three stages of an escapee: Curious, Motivated, and Liberated
Why your path out of corporate isn’t a leap — it’s a shift
The reality of layoffs, RTO mandates, and the “profits over people” era
Why authenticity beats production quality every time
The mindset shift corporate doesn’t prepare you for

Why this conversation matters

A 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 Catherine

Check out Catherine Jelinek’s podcast:

👉 Breaking Through the Noise

Available on Apple, Spotify, and YouTube. Follow and support her work — she’s having the conversations corporate workers need to hear.
25 min
November 13, 2025Bet on Yourself: From Video Agency to Solo Productized Service with Neil K. Carroll
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 Learn
Neil’s escape path: agency burnout → COVID pivots → higher-ed → solo
The “Root Thread” deep testimonial approach and why it delivers strategic customer insight
How to productize what you already do without boxing yourself in
Why referrals and local networks are enough for a one-person business
How Neil priced his offer and why undercharging early is part of the process
The 4 levers every offer should hit: save time, save money, make money, reduce risk
Why betting on yourself beats betting on corporate stability
Key Takeaways
Your corporate title doesn’t matter—your ability to solve problems does
Productized services make selling and delivery easier
Customer conversations reveal the real value you offer
Solopreneurs don’t need 100 clients—you need a few right-fit ones
You can always go back to corporate… but very few people want to once they leave

About Neil K. Carroll

Neil 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. Carroll

Website: vidwheel.com
38 min
November 12, 2025He Didn’t Just Escape Corporate—He Left the Country W/Ed Patterson
Download the FREE Escapee Starter Kit

Episode Summary

After 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 Close

Key takeaways
Plan 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.
Guest

Ed 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.”
35 min
November 07, 2025The Go-Giver Playbook for Escapees (Greatest Hits)
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.
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.
31 min
October 31, 2025Healthcare for a Company of One: A Real Alternative for Solopreneurs w/Tom Morrissey
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.
34 min