Dreamcatchers

What if your exit could be the beginning of your best story, not the end? In this deep-dive workshop-style episode, Jerome Myers reunites with Homer Smith, financial strategist and founder of Konvergent Wealth, to unpack the financial and emotional blueprint for achieving true post-exit success. Whether you’re years from selling your business or already navigating offers, this episode delivers the playbook for preserving family wealth and personal purpose. If you're a business owner asking, "What's next?" — this one's for you. [00:00 – 12:00] Two Paths After the Sale Why 70% of businesses brought to market don’t sell—and how to avoid being one of them The post-sale "tragedy" no one talks about “Only about 6% of owners who go to market are highly satisfied with the outcome.” The three pillars of a successful exit: business readiness, market readiness, and owner readiness [12:01 – 26:00] The Real Reasons Founders Miss Out Unrealistic valuations and the myths around multiples Why

What if your biggest failures were the stepping stones to your greatest impact? In this raw and revealing episode, Jerome Myers sits down with Kasim Aslam,  serial entrepreneur and founder of the world’s top-ranked Google Ads agency,  to unpack his journey from troubled teen to 8-figure exit. With unmatched candor, Kasim shares the highs, the hard truths, and why his life’s mission today is centered on global employment, not just profit. If you’ve ever felt stuck, burned out, or unsure of what’s next, listen closely. [00:00 – 12:10] Two Exits, One Framework Building the #1 Google Ads agency Productizing services for scale The behind-the-scenes of an 8-figure exit [12:11 – 22:45] Integrity Over Everything Why most agencies fail their clients Saying no to the wrong deals How honesty fuels demand and client trust [22:46 – 34:00] The Rocky Road to Reinvention Growing up in poverty and crime Losing everything in the '08 crash Finding purpose through f

What if you could add $1M to your exit, without working extra years? Jerome Myers talks with Mahen Gundecha, a seasoned dealmaker, about how timing, positioning, and rolled equity can boost your exit value. Learn why most exits fail, what buyers want, and how to avoid costly delays. A must-listen for any founder thinking about an exit, now or years from now. [00:00 – 12:58] Mahen’s Global Journey + The Wake-Up Call for Founders From Tanzania to Toronto to Pennsylvania: Mahen’s backstory Why unplanned exits leave millions on the table The value of starting exit prep years before you're ready [12:59 – 24:32] What Makes a Business Truly Sellable Why only 20% of listed businesses ever sell Founder dependency: the hidden value killer How rolled equity can add major upside post-sale [24:33 – 36:25] Market Forces You Can’t Ignore: Consolidation + Competition What happens when your competitor is acquired by private equity Why does consolidation raise the r

What if your business could attract the right buyer before you're even ready to sell? In this episode, exit strategist Lorraine McGregor reveals why only 1–2% of businesses ever sell and how to ensure yours is one of them. She breaks down the hidden reasons exits fail, the mindset shifts founders must make, and what buyers are looking for. If you think buyers will show up when you're ready, think again. This is a must-listen for any founder considering exit, even years in advance. [00:00 – 07:00] The Harsh Truth About Business Exits Why most small businesses never sell M&A myths: Buyers don’t show up when you’re ready, they buy when it suits them How Lorraine discovered the “black box” language of M&A [07:00 – 16:00] Why Buyers Walk Away Internal chaos kills deals: unresolved partner conflicts and weak management teams The real reason exit planners and M&A brokers won’t take you on as a client What does it mean to “become the business your buyer is looking for” 

What if your team, not your revenue, is the key to a successful business exit? In Part 2 of the Regret-Proof series, Jerome Myers and Maria Forbes of Stratis Human Capital Solutions explore how people issues like misalignment, legacy hires, and founder-dependence quietly drain business value. Learn how to turn your workforce into your strongest asset, whether you’re years from selling or fielding offers now. [00:00 – 04:30] Why Human Capital Is the Missing Link in Exit Planning Human capital is a strategic value driver, not just HR Buyers assess workforce strength, leadership alignment, and role clarity Growth and exit readiness should be aligned and simultaneous [04:30 – 08:30] Alignment: The First People Challenge “Cloning yourself” limits innovation and scalability Misalignment hinders synergy, efficiency, and growth True alignment means matching instincts and strengths to roles [08:30 – 13:30] Hiring Habits: Staff vs. Stakeholders Staff support the owner'

What if selling your business could be the proudest moment of your career, not your biggest regret? In this episode, Jerome Myers talks with David Shavzin, founder of The Value Track and co-founder of the Exit Planning Exchange Atlanta. With decades of experience in exit planning and M&A, David shares why so many entrepreneurs feel disappointed after selling, and how you can avoid it. Discover how to think like a buyer, increase your business's transferable value, and prepare for a successful, meaningful exit. If you’re ready to transition from business owner to legacy builder, you won’t want to miss this conversation. [00:00 – 07:50] The Cost of Poor Planning 75% of owners regret selling, early planning is the antidote Baby Boomer wealth transfer = huge opportunities + huge risks Lack of preparation = loss of personal and generational wealth [07:50 – 23:50] Own the Buyer’s Mindset Big myths busted: quick exits, easy deals, setting your price Buyers pay for cash flow, not dreams

What does it look like to engineer a business that serves your life—and not the other way around? Matthew Jarvis, founder of Jarvis Financial and co-founder of The Perfect RIA, built a thriving financial advisory firm designed for freedom. In this episode, Matthew opens up about building a “lifestyle practice,” navigating the emotional landmines of succession, and making bold moves (like taking 150+ days off a year!) without sacrificing business performance. Expect honest stories about designing a business around your values, preparing for exit from day one, and why impact, not just income, should be the endgame. If you're looking to exit right, not just exit rich, this episode will shift your thinking. [01:13 – 08:12] Design Your Life First Life by Design: Matthew shares how he built a business to support his ideal lifestyle Lifestyle Practice: Intentional client selection and lean operations Personal Metrics: Why time off mattered more than AUM growth Early Vision: Planning for exit even in the ear

Most people think money is the biggest barrier to leaving their job—but they’re wrong. In this powerful mastermind session, Jerome Myers joins real estate investors and corporate pros to reveal the real cost of walking away: emotional, mental, and operational. Drawing from his leap from corporate at the peak of success, Jerome shares hard-earned lessons on why most exits fail, the myths of passive income, and what truly makes wealth worth building. If you're dreaming of leaving your W2 or already have, this conversation will shake your assumptions and refocus your purpose. Press play and discover what it takes to build a life of freedom and fulfillment. [00:00 – 04:57] Real People at the Edge of a Leap Investor intros: career paths and exit goals Common thread: W2 jobs and uncertainty Jerome sets the tone for real talk [04:58 – 11:45] Jerome’s Exit Story Built a $20M division—then told to downsize Choose values over comfort and quit Faced with cash flow struggles with no pl

What happens when your business becomes your identity, and you sell it? Julie Cole, co-founder of Mabel’s Labels, went from lawyering to label-making, raising six kids while helping build a household name from her sister’s basement. She opens up about the unexpected acquisition, how her team navigated co-founder dynamics, and the emotional complexity of stepping back while staying connected to the brand. Expect stories of scrappy beginnings, smart business moves, the real challenges of exiting with multiple partners, and how to redefine purpose after the deal is done. If you've ever wondered what success looks like on the other side of the sale, this conversation pulls back the curtain.  [01:26 – 07:26] From Basement to Brand Intro & Vision: Julie introduces herself and the idea Bootstrapping: Four founders and personal drive kickstarted the venture Real Need: A product born from personal challenges Validation: Early word-of-mouth proved the concept [07:26 – 16:44] Building the Machine Team Dynamics

How do high-earning professionals maximize their financial opportunities while avoiding common tax pitfalls? In this insightful conversation, Jerome Myers sits down with Steven Jarvis, a tax strategist dedicated to helping business owners and professionals confidently navigate tax planning. Steven shares actionable strategies to optimize tax savings, uncover overlooked deductions, and build a proactive approach to financial planning.  Whether you're a seasoned entrepreneur or just getting started, this episode will equip you with the knowledge to make tax-smart decisions that align with your financial goals. [00:00 - 06:42] The Importance of Proactive Tax Planning Avoiding Common Mistakes – Why waiting until tax season can cost you thousands Mindset Shift – Taxes are not just an annual burden but an ongoing financial strategy Collaboration is Key – Working with CPAs and financial advisors can uncover hidden opportunities [06:43 - 14:28]  Maximizing Deductions & Reducing Liability Hidden Tax Savings –

Selling a business is often seen as the ultimate victory, but what happens when the excitement fades and uncertainty sets in? In this episode, Jerome Myers, America's leading exit authority, uncovers founders' emotional and psychological challenges after selling their businesses. Many assume financial freedom will bring fulfillment, only to feel lost, disconnected, or restless. Jerome reveals the hidden traps of the exit journey and provides actionable insights to help founders transition with clarity and purpose.  Learn how to avoid the everyday post-exit struggles and step confidently into your next chapter. [00:00 - 06:45] The Founder’s Exit Paradox Exiting a business isn’t just a financial transaction—it’s a personal transformation. Many founders assume wealth will bring fulfillment, but the reality is often differen.t The sudden loss of structure, identity, and purpose can be overwhelming Planning beyond the financials and preparing for emotional shifts is the key to a successful exit [06:46 - 15

What if selling your business didn’t bring the fulfillment you expected? While most discussions around business exits focus on valuation, deal structures, and financial freedom, few address the emotional toll that follows. In this episode, Jerome Myers, America's leading exit authority, unpacks the silent costs of selling a business—the identity crisis, emotional void, and six centers of doubt that can leave founders feeling lost. He shares why 75% of entrepreneurs regret their exits and reveals a four-step framework to help navigate post-exit life with clarity and purpose. If you’re planning an exit or struggling with what comes next, this episode is your guide to designing a fulfilling next chapter. [00:00 - 01:15] Introduction: The Emotional Toll of Selling Your Business Exiting a business isn’t just financial—it’s personal and emotional Many founders feel lost, questioning their identity after selling This episode uncovers what happens emotionally after an exit [01:16 - 03:09] The Six Centers of Do

Success often comes at a cost. In this episode, Jerome Myers explores the Five Scars of Success—key life experiences that shape high-achieving entrepreneurs: conditional love, suicidal ideation, financial ruin, near-death experiences, and early loss of a loved one. While these experiences fuel ambition, they can also make business exits emotionally complex. Jerome shares how to reframe these scars to build a fulfilling next chapter beyond business ownership. [00:00 - 01:00] Introduction & The Five Scars of Success A reminder to check in on others. Success is often shaped by personal struggles. Exiting a business is about more than money. [01:01 - 03:00] Scar #1: Conditional Love Achievementis tied to receiving love. Creates a need for external validation. Must redefine self-worth beyond success. [03:01 - 04:30] Scar #2: Suicidal Ideation High-pressure success leads to dark moments. Many founders struggle in silence. Support systems are crucial. [04:31 - 06:00] Scar #3: Financial Ruin Many exp

What if the life you've carefully built suddenly changes—whether through divorce, a business exit, or an unexpected transition? How do you redefine success when everything familiar is gone? Michelle Jacobik, a financial expert and entrepreneur, shares her firsthand experience of navigating these pivotal moments. She and host Jerome Myers discuss rebuilding financial stability, rediscovering personal identity, and cultivating a mindset that fosters lasting success. Expect raw honesty, practical guidance, and an inside look at the steps needed to create a fulfilling next chapter.  Tune in to gain the confidence and strategies to embrace change and turn uncertainty into opportunity. [00:00 - 03:14] - The Power of Support & Mindset Shifts Purpose, values, and gifts define contributions Support systems are essential for growth Mindset impacts success [03:15 - 12:29] - Navigating Divorce and Financial Transitions Divorce is both emotional and financial Plan for financial stability post-divorce Avoid emoti

What if the biggest myth about exit planning is also the most dangerous? In this solo episode, Jerome Myers, America's leading exit authority, breaks down the costly mistake founders make—waiting too long to plan their next move. He shares hard-hitting insights on the Founder’s Exit Paradox and why delaying the conversation about “what’s next” can leave you lost, unfulfilled, or even financially vulnerable. Jerome explores the excuses founders tell themselves, the four unexpected reasons entrepreneurs are forced to exit, and the ultimate question every business owner should ask: If you only had six months left before you had to exit, what would you do differently today? [00:00 - 02:44] The Exit Paradox: The Dangerous Myth That’s Holding You Back Waiting too long to plan leads to regret Exit is a transition, not the end Are you exiting from or to something? [02:45 - 008:51] The Three Excuses Founders Use to Delay Their Next Move “I’m too busy.” Avoiding the future creates problems “I don’t know what’s

What if your relationship with money determined your freedom? Most people chase wealth, but few truly understand how to manage it in a way that brings lasting security and fulfillment. Are you making financial decisions that serve your future, or are you unknowingly setting yourself up for financial traps? Jerome Myers sits down with Drew Boyer, author of Hip Hop & Finance, to explore the financial lessons hidden in hip-hop. From MC Hammer’s financial downfall to 50 Cent’s unexpected business acumen, this conversation unpacks the actual cost of economic ignorance, and the mindset shifts needed to build lasting wealth. Expect powerful stories, hard-earned wisdom, and a fresh perspective on personal finance that blends music, culture, and money in a way you’ve never heard before. [00:00 - 00:59] The Inspiration Behind Hip Hop & Finance Jerome introduces Drew and his book How hip-hop lyrics teach financial lessons Drew’s journey from drummer to finance Why financial education should be accessible [03:00

What if success isn’t enough? Many entrepreneurs reach financial freedom only to feel lost. Walter Paulsen, who built a $500M company, shares why wealth alone doesn’t bring fulfillment and what truly matters after the exit. Expect real talk on resilience, competition, and finding purpose beyond business. Walter and Jerome Myers break down why some thrive post-exit while others struggle—and how to make sure you’re on the right path. Listen now to discover what makes success truly meaningful. [00:00 - 04:55] - The Nature of Happiness & Purpose Happiness is fleeting, not a permanent state It’s a byproduct of meaningful work, not wealth Chasing money without purpose leads to dissatisfaction [04:56 - 07:30] - Competitive Mindset & Personal Growth Walter’s sports background shaped his resilience Self-competition builds long-term success Physical challenges enhance mental toughness [07:31] - Building a $500M Business in Four Years Led Blackhawk Network, pioneering the gift card industry Secured multi-y

Exiting your business should be a celebration—but why do so many founders feel lost afterward? In this solo episode, Jerome Myers explains the emotional cost of exiting, why money alone isn’t enough, and how to clearly navigate the transition.  Whether you're considering an exit or already on the other side, this episode will help you find purpose beyond the payday. [00:00] The Founder’s Exit Paradox Exits aren’t just financial—they're emotional transformations Many founders feel unexpected emptiness after selling Your next move matters—success isn’t just about money   [02:00] The Harsh Reality of Selling a Business Only 2 in 10 businesses that list sell Most founders assume buyers will line up—but they won’t Sellability matters—plan ahead or risk regret [04:00] The Emotional Rollercoaster Exiting brings loss, grief, and identity shifts Many founders fear what’s next and hesitate to sell Clarity is key—know where you're going before you exit [06:00] Why Money Isn’t Enough Money can’t replace

What’s stopping your business from thriving without you? In this episode, Jerome Myers hosts Adi Klevit, founder of Business Success Consulting Group, to uncover the often-overlooked value of documenting and implementing processes. Adi shares real-life stories of businesses that doubled their value, onboarded employees faster, and achieved true operational freedom—all by putting robust systems in place.  Whether you're planning to sell your business or simply want to reclaim your time, this episode offers actionable insights to ensure your business works for you, not the other way around. [00:00 - 07:28] The Power of Documentation Processes are key to scalability and freedom Knowledge transfer ensures continuity Documented processes can double business value [07:29 - 12:56] Building a System-Driven Culture Processes must be implemented, not just written Accountability ensures systems are followed Onboarding can be reduced from months to weeks [12:57 - 18:24] Process Mapping and Simplifying Complex

How do you create a business that builds lasting value and grants you the freedom to live life on your terms? Justin Goodbread, a seasoned entrepreneur with seven successful exits, shares his insights on designing businesses that thrive without your constant involvement. Learn how to build scalable systems, create recurring revenue, and focus on what matters most—your family,  passions, and legacy. If you’re ready to shift from being indispensable in your business to becoming a legacy builder with a life of purpose and fulfillment, this conversation will show you how. Listen now to discover the mindset and strategies that can transform your journey. [00:00 - 10:32] Seasons of Entrepreneurship Embrace the chaos of early entrepreneurship. Forget balance; focus on a blended life. Efficiency grows by knowing your strengths. [10:33 - 20:48] Mastering Efficiency and Delegation Review tasks to find what aligns with your strengths Delegate low-value activities to save time Focus on high-impact tasks for gro