Life After W2

From Corporate to Creative. Olivia Atkin’s Inspiring Journey. What you will learn:• How Olivia transitioned from professional sports to corporate life• Why she pursued an MBA for new challenges and opportunities• How networking became essential during the COVID job search• The corporate culture issues she experienced at Lockheed Martin• How gender bias shaped her understanding of workplace dynamic...

From Misconceptions to Mastery. Jim McEleney’s Franchise Journey. What you will learn:• How Jim went from misconceptions about franchising to exploring real opportunities• Why franchise owners lived a lifestyle that caught his attention• How working with a consulting group helped him identify goals and transferable skills• What the research and due diligence process looks like in franchising• Why...

Breaking Free from the Past. Mark Robinson on the Illusion of Safety and the Path Forward. What you will learn:• Why the past feels like a magnet and how to break its pull• How negative energy disguises itself as comfort and familiarity• The difference between real experience and the mirage of safety• How to shift your mindset from retreating to advancing• Why paying attention to positive energy c...

From Employee to Firm Owner. Kyle Beltle Shares the Turning Point That Changed Everything. What you will learn:• How a single moment can ignite the decision to start a firm• How to build personal runway for your transition• What to expect when employment shifts faster than planned• How to navigate the emotional and financial rollercoaster of leaving stability• What early marketing and client acqui...

“Comfort is the biggest obstacle to growth.” In this episode, Mike Henzgen shares how he left a stable accounting W2 to build a business on his terms. He walks through the real tradeoffs behind leaving, from testing real estate to launching an offshore accounting team, and why the best time to take the leap might have been yesterday. You will hear the mindset shifts that made it possible. Owning y...

“Invest in what you know, not what you are being sold.” In this episode, retirement expert JP Ruiz QKA CISP pulls back the curtain on solo 401k and self directed IRA plans. We get real about record keeping, compliance, and the simple steps to move from a traditional employer plan into a structure that supports tax advantaged alternative investing. JP shares the practical toolkit most people miss....

“I loved teaching—but I couldn’t keep giving from an empty tank.” After a decade in the classroom, Kerry Komarov hit a breaking point during COVID and extended maternity leave. Instead of returning, she mapped her transferable skills—storytelling, communication, digital creativity—into a content marketing business that fits family life. Kerry shares the mindset shift from the “safe paycheck” to se...

“I thought I’d finally found the perfect job — until it swallowed me whole.” After 15 years in corporate recruiting and management, Lindsey Tague hit burnout. Getting laid off from a startup became her wake-up call to stop chasing titles and start building something of her own. In this episode, she shares how she turned that moment into a thriving career in social media and content marketing. Lind...

“You do not have to be a thousand steps ahead. Just one.” In part two, Aloysius “Al” Carl flips the mic and interviews Jon about leaving a stable consulting career to build a lending business, the messy middle, and learning to share more of his own story. They unpack imposter syndrome, journaling for clarity, and why focus beats multitasking. Jon explains how he helps families redeploy old 401k an...

“Every big win is a stack of small wins.” In this episode, Aloysius “Al” Carl shares how a whistleblower crisis ended his rise at Dun and Bradstreet and pushed him into entrepreneurship. He opens up about the emotional toll, the reality of cash flow, and why calm, focused energy beats hustle. Al walks through the pivots that shaped his path. Building a consulting firm from zero. Returning to corpo...

“More than 70 percent of my day was charting for insurance, not caring for people.” Family nurse practitioner Monica McKitterick shares how she walked away from corporate healthcare to build a membership based direct primary care practice that puts patients first. We unpack the moment she chose freedom, how she launched in a new state with no patient list, and what finally quieted the imposter syn...

“I kept getting glowing reviews—but no path to grow. So I built my own.” In this candid episode, designer-turned-founder Nikki Holbrook shares how the pandemic clarified her values and pushed her to leave a stable UX role for mission-driven work with women-owned businesses. She breaks down the leap from billable hours to productized branding + website packages, why value-first outreach wins client...

“Right before I quit, the firm offered me a $20,000 raise and a mentor I’d always wanted. I knew it was a test.” After graduating law school and landing at a top national firm, Miguel Perez seemed to have it all — prestige, stability, and a clear path to partnership. But the reality of tracking every billable hour and suppressing his entrepreneurial instincts became too heavy. In this episode, Mig...

When Michael Hoang’s company grew from $180M to $1.1B, he thought his loyalty would pay off. Instead, promises were broken—and a tow truck came for his company car three days before his vacation. That moment became the catalyst for his freedom. In this episode, Michael shares how he built a bridge out of his W-2 life—starting with house hacking, buying rentals while traveling full-time, and eventu...

“When you’re working at ESPN, everyone thinks you’ve made it. But for Nicholas Tana, success without creative freedom started to feel like another kind of trap.” In this episode, Nick shares how leaving a coveted role at ESPN led him down an unpredictable path—from contract work and failed starts to building a production business that blended creativity, independence, and meaning. He reveals what...

Thinking about leaving your 9 to 5 but not sure where to start? Mark Astor’s journey from W2 employee to building the nation’s only law firm focused on mental health and addiction shows the real challenges and the real opportunities of making the leap. In this episode of Life After W2, host Jon Chan talks with entrepreneur and attorney Mark Astor about the messy but rewarding path to entrepreneurs...

In this episode of Life After W2 , host Jon Chan sits down with Angela Wyant , who left a successful W2 career in technology management to pursue entrepreneurship in real estate. Angela shares the mindset shifts that helped her navigate unexpected challenges, the influence of her entrepreneurial family background, and how she redefined freedom and success on her own terms. We dive into: What it re...

🎙️ Life After W-2 Podcast with Jon Chan & Ashli Mason Thinking about leaving your 9-to-5 and stepping into entrepreneurship? In this episode of Life After W-2 , Jon Chan sits down with Ashli Mason to talk about what it really takes to transition from a traditional W-2 job into business ownership. They dive into: Why clarity is the first step before making big life changes The financial challen...

🌟 Welcome to The Road to 1! 🌟In this powerful interview, we sit down with Adam Colburn—a real estate investor, coffee shop owner, and family man based in Raleigh, NC—who went from working in HVAC and real estate photography to flipping houses, wholesaling, and scaling a sober living rental portfolio nationwide.🚀 What You'll Learn in This Episode:• How Adam closed his first wholesale deal af...

🌟 Welcome to The Road to 1! 🌟Looking to take full control of your retirement account and invest in real estate, private lending, or alternative assets? In Episode 80, we’re joined by Joe and Matt from CamaPlan, a leading provider of self-directed IRAs and 401(k)s, to dive deep into:✅ What is a self-directed IRA?✅ How to avoid UBIT (Unrelated Business Income Tax)✅ The difference between debt v...

🌟 Welcome to The Road to 1! 🌟In this inspiring episode, we sit down with Alexis Morgan, founder of Peach State Capital, to uncover her powerful journey from real estate hustler to fund manager. Learn how Alexis built confidence through cold calls, found mentorship through intentional networking, and pivoted from wholesaling to capital raising — all before the age of 23.🎯 Key Takeaways:• From hi...

🌟 Welcome to The Road to 1! 🌟In this episode, I’m sharing the 5 most important lessons I’ve learned after four years in real estate and building my lending company. Whether you’re a seasoned investor or just starting out, these insights might help guide you on your own path to success. I’ll dive into the challenges and triumphs I’ve faced, and the key takeaways that have shaped my journey. From...

🌟 Welcome to The Road to 1! 🌟🚗💰 Creative Finance Isn’t Just for Real Estate! 💡 Learn how Mike Davis is revolutionizing the industry by using seller financing to buy and sell cars, trucks, boats, RVs, and even planes! Plus, discover his journey from wholesaling real estate to scaling his SellerFinance.io marketplace. Takeaways from Episode:1️⃣ Creative Financing Works for Cars Too! 2️⃣ $1.5M P...

🌟 Welcome to The Road to 1! 🌟In this episode, I sit down with Steve Scanlon, executive coach and mindset expert, to dive deep into the power of neuroplasticity, emotional intelligence, and leadership development. 🚀Steve shares his journey, the science behind rewiring the brain, and how mastering mindset can drive personal and professional success. Whether you're an entrepreneur, investor, o...

🌟 Welcome to The Road to 1! 🌟In Episode 75, I share my real estate investing journey—from house hacking and buying rental properties to scaling up to 30 doors across multiple markets. But after years of dealing with property management headaches, tenant issues, and inconsistent cash flow, I’ve decided to pivot. 🚀Now, I’m selling off my rentals and moving into private lending, where I can scale...