
Hosted by Jerome Myers - Advisor to exiting founders · EN

What happens when the business exit is not the only exit happening? In this episode of Your NEXT, Jerome Myers sits down with Brian Roeder, founder of Bee Oak Partners and Managing Agent for Transworld Business Advisors’ Monterey office. Brian shares the story of building Barrel Oak Winery from raw land into one of Virginia’s busiest wineries, welcoming up to 1,500 guests on busy Saturdays, growing a committed team, raising more than $2 million through nonprofit events, and ultimately selling the business in 2022. But this conversation is not just about selling a winery. It is about navigating a double exit. Brian built the business with his former wife, and as the marriage came apart, the business had to be protected, investors had to be considered, and the dream they had built had to be carefully unwound. He describes the moment after the wire hit as a physical release, like a load had been lifted from his shoulders. But relief did not automatically create clarity. After the sale, Brian moved back to California for what he thought would be his next chapter in the family business. When that path did not unfold as expected, he faced another transition and another question: Who am I now? In this episode, Jerome and Brian explore: The emotional weight of selling a business Why the team is often what founders miss most How divorce, investors, employees, family, and identity can collide during an exit Why relief is real, but not the same as purpose What Brian calls “the hollow place” after success The difference between connectors and extractors Why the right advisor starts with the owner’s story, not just the numbers How Brian now uses his experience to help other owners avoid the mistakes he had to learn the hard way A successful transaction can close the deal. An excellent exit protects the person on the other side of it. Connect with Brian Roeder:https://beeoak.combrian@beeoak.com Take the Exit Readiness Assessment:https://www.exittoexcellence.com/era Schedule a conversation with Jerome:https://calendly.com/yournext/30-minute-1-on-1 Learn more about your ad choices. Visit megaphone.fm/adchoices

What happens after the wire hits? For years, founders imagine the exit as the summit. The documents are signed. The legal teams are done. The congratulations pour in. The number in the bank account finally reflects the sacrifice, pressure, and grit it took to build the company. Then Tuesday morning arrives. No urgent emails. No executive team waiting for direction. No fires to put out. No company demanding your identity, energy, and leadership. Just silence. In this episode of Your NEXT, Jerome Myers explores one of the most overlooked risks in exit planning: the psychological and structural collapse that can happen after a successful transaction. Inspired by The Exit Expedition: Why the Deal Is Only the Summit, this conversation unpacks why so many founders prepare their companies for sale while doing almost nothing to prepare themselves for life after the exit. You’ll hear about: The Transaction Illusion The invisible role the business plays in a founder’s life The Depletion Window after an exit The Six Centers of Doubt Why “respectable noise” can become a trap How to design the descent before you reach the summit A successful transaction monetizes the business. An excellent exit aligns the life. If this resonates, here’s the next step. Take the Exit Readiness Assessment: https://www.exittoexcellence.com/era Schedule a conversation: https://calendly.com/yournext/30-minute-1-on-1 Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, we break down the three nominees for the Excellence in Exit Planning Awards and evaluate them the way most people won’t: by looking at the actual criteria, the quality of their ideas, their public influence, and whether they’ve truly moved the profession forward. We examine the cases for Todd Yeiter, Kristen Carlson, and Jerome Myers, and compare them across seven dimensions, including originality, credibility, practical applicability, public-facing footprint, and ecosystem impact. But this conversation goes beyond an award prediction. It becomes a deeper discussion about what thought leadership really is in the world of exit planning. Is it mastering the structural mechanics of a deal? Is it helping owners build companies that can run without them? Or is it naming the invisible human problem no one else wants to touch: what happens to the founder after the deal is done? If you care about business exits, founder psychology, transition planning, or the future of the exit planning profession, this episode will give you a lot to think about. In this episode: The official criteria for Thought Leader of the Year Why thought leadership is harder to judge than business performance The case for each nominee The seven-part scoring framework used in the analysis The final prediction for who wins in 2026, and why The bigger question: If the money were no longer the issue, and the transaction was complete, would you actually know who you are on day two? Learn more about your ad choices. Visit megaphone.fm/adchoices

Most founders believe the liquidity event is the finish line. It isn’t. In this episode of Your NEXT, Jerome Myers sits down with Colin Hodge, a founder who grew a dating app to millions of users with virtually zero ad spend, navigated a first exit, joined the acquirer, and then experienced the part nobody markets: the emotional “now what?” that follows the deal. Jerome unpacks what he calls the Transaction Illusion: the belief that money automatically brings relief, identity, and fulfillment. Colin shares how vulnerability became a growth catalyst, how his company was forced into a fire sale, and the unbelievable twist of buying his own business back and scaling it again. If you’re building toward an exit, recovering from one, or quietly wondering why success feels… weird, this conversation will land. Key topics: Why money doesn’t solve the post-exit questions it exposes Identity shifts, shame, and the silent side of “success” Organic growth through user psychology The boomerang story: sell it, buy it back, grow it again Why founders need a “descent protocol” before they summit Links: Learn more: exittoexcellence.com Explore the work: [NEO Assessment / Exit Readiness Assessment link] Guest: colinhodge.com (book + latest projects) Learn more about your ad choices. Visit megaphone.fm/adchoices

Josh Mastel did not exit because he hit some magical finish line. He exited because the business stopped giving him energy. In this episode of Your NEXT, Jerome Myers sits down with Josh to talk about betting on yourself, walking away from comfort, and building a life in alignment with what matters most. Josh shares the story of cashing out his 401(k), getting fired early in his career, losing his brother at 18, building a business he eventually outgrew, and then helping his wife scale her company into a $100M ARR technology services firm. This conversation is about more than entrepreneurship. It is about resilience, identity, priorities, and the courage to stop being a prisoner of something you built. If you are trying to decide whether your business still fits who you are becoming, this episode will stay with you. Learn more about your ad choices. Visit megaphone.fm/adchoices

Most advisors think the goal is to build a great firm. The best ones realize the real challenge is what happens when it’s time to step away from it. In this episode of Your NEXT, Jerome Myers sits down with Jon to explore the full arc of building, scaling, and ultimately exiting a wealth management firm that reached $2.5 billion in assets under management. Jon shares his journey from professional football to financial advisor, what drew him into the industry, and how he and his partner built a firm focused on serving athletes and entertainers. As the business grew, they shifted into an aggregator model, acquiring other advisory firms to expand their reach and capabilities. But growth is only part of the story. Jon opens up about the realities of being acquired, navigating integration, stepping away from day-to-day leadership, and redefining his role after the transaction. This is a conversation about more than strategy. It’s about transition. If you’re building a firm, considering acquisitions, or thinking about an eventual exit, this episode offers a grounded look at what the process really requires. From NFL career to financial advisor Why Jon chose to serve sports and entertainment clients Building and scaling an RIA to $2.5B in AUM Transitioning into an aggregator model through acquisitions Lessons learned from inorganic growth The acquisition process and integration challenges Letting go of day-to-day operations Redefining identity and role after the exit Advice for advisors planning their own transition What We CoverKey Moments00:00 Family stories and St. Patrick’s Day traditions03:45 Family travel and keeping kids engaged12:18 From NFL to financial advisor19:27 Building an RIA for athletes and entertainers35:00 Scaling through acquisitions45:15 The acquisition and integration process01:05:00 Life after the deal01:17:32 Advice for advisors considering an exit Learn more about your ad choices. Visit megaphone.fm/adchoices

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Jerome Myers interviews Mark Hartmann, exited founder and M&A advisor, on what it really takes to sell a business on strong terms and avoid the common post-exit traps. They cover seller’s remorse, identity after exit, de-risking a company for buyers, why earnouts can go sideways, and how founders should build a deal team that protects the outcome. Topics covered:• Selling Ethicare Advisors to a private equity-backed buyer• Deal readiness and due diligence preparation• De-risking customers, vendors, employees, and owner dependency• Earnouts, reps & warranties, escrow, and transition terms• Building a personal plan for life after the sale Links:Mark Hartmann: hartmannrhodes.comBook: The Sweat Equity Payday Learn more about your ad choices. Visit megaphone.fm/adchoices

Daniel Rudyak built a healthcare company the hard way. No venture capital. No safety net. And for a long stretch, not even the freedom to buy “two tacos” without doing the mental math. In this episode, Jerome Myers talks with Daniel, founder of ReadyRx, about what it takes to go from private equity boardrooms to the chaos of building: 120-hour weeks, 18 months pre-revenue, and the constant pressure of carrying a mission that’s deeply personal. ReadyRx has grown to 10,000+ monthly customers and a reported $70M valuation, but this conversation isn’t about hype. It’s about the truth founders rarely say out loud: the climb is hard, the summit is brief, and the “money” doesn’t give you what you think it will. If you’re chasing an exit, thinking about raising capital, or worried about what happens after the deal closes, press play. In this episode: Why ReadyRx exists (and the healthcare failures that sparked it) The real difference between investing in businesses and building one Why they refused venture money and what control is worth The hidden skill founders need after liquidity: allocation, not adrenaline Why most people don’t break on the way up, they break on the way down Learn more about your ad choices. Visit megaphone.fm/adchoices

Most founders believe the exit will finally deliver freedom. But what if that belief is the lie? In this episode, Jerome Myers and Josselyne Herman-Saccio explore what founders discover too late about selling their business. Why achievement doesn’t automatically produce fulfillment. Why the exit doesn’t erase identity pressure. And why designing your “next” requires more than a successful transaction. If you think the deal will solve everything, listen first. Learn more about your ad choices. Visit megaphone.fm/adchoices