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The Exit - Presented By Flippa

The Exit - Presented By Flippa
The Exit - Presented By Flippa
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  • The Power of Brand and Timing: Rob Basso’s Multi-Million Dollar Exit Playbook
    Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit, entrepreneur Rob Basso shares how he built Advantage Payroll Services into a $25M business and exited on his own terms. His journey started humbly, wrapping resumes in deli sandwiches, and ended with a strategic sale to a public company. Rob planned his exit from day one, focusing on clean financials, employee retention, and leveraging his personal brand to win trust. He urges founders to be visible, not just their company, and to run a business that’s always “sale-ready.” When it came time to sell, he passed on higher PE offers with earn-outs in favor of a lower upfront deal because he was emotionally done and ready to move on. The decision? One of the best he’s ever made. Post-sale, Rob struggled with identity loss but rebounded by helping others build personal brands and make better business decisions. His final lesson? Be authentic. Trying to be someone you’re not, whether with staff or clients, can backfire. Rob’s story is a reminder that successful exits aren’t just financial: they’re personal. And planning ahead, staying true to yourself, and choosing the right buyer can make all the difference. -- Rob Basso is a recognized business coach, entrepreneur & speaker. He is a published author, professional speaker and sought-after media personality. He has operated and sold many businesses in the past two decades including Associated Human Capital Management and Advantage Payroll Services. The most recent two companies were sold to public companies at industry high valuations. Known as The Everyday Entrepreneur, the media frequently calls upon Rob for his insights, opinions and expertise. In 2022 he was a judge for the American Business Awards (division of the Stevie Awards), panelist for the Middle Market Alliance, mentor for the Next Gen Summit and numerous other speaking engagements. Rob Basso on LinkedIn: https://www.linkedin.com/in/robbasso/ Website: https://www.robbasso.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/
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  • Profit, Purpose & the Creator Economy: Lessons from Bubba Page’s Startup Journey
    Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit, serial entrepreneur and investor Bubba Page opens up about his journey from building a bootstrapped B2B sales company (Launch Leads) to launching Influence.VC, a venture fund focused on consumer tech and creator-led startups. Bubba shares how his first successful exit funded his lifestyle and family, while his venture-backed failure taught him invaluable lessons about ego, resilience, and emotional health. He emphasizes the often-overlooked value of lifestyle businesses, those that generate strong cash flow without external funding, and challenges the myth that venture capital is the only path to success. The conversation dives into the power of the creator economy, and how partnering with influencers can accelerate brand growth with lower customer acquisition costs. Bubba also reflects on selling his business just days before the 2020 COVID shutdown. Listen to the episode for real-world insights for founders questioning when to sell, whether to raise capital, or how to build a profitable business without burning out. -- Bubba Page is a single dad to 8 incredible kids—four boys, four girls—a devout Christian, and a serial entrepreneur who’s built and sold multiple companies, including a three-time Inc5000 standout, LaunchLeads.com, which he sold in 2020. Now, he’s pioneering Influence.vc, a venture capital syndicate on AngelList, where his social media influencer expertise invests and turbocharges startups. He is also a sought-after advisor in fundraising, B2B sales, influencer marketing strategy, and angel investing, a frequent podcast guest, and soon-to-be author of Fatherhood & Entrepreneurship, blending business and Christian principles for family life. Named one of 2024’s 'Coolest Entrepreneurs' by UVBizQ Magazine, he has also written for Inc Magazine. Bubba Page on LinkedIn: https://www.linkedin.com/in/bubbapage/ Websites: https://influence.vc/ - https://thebusinessbootcamp.com/ Instagram: https://www.instagram.com/bubbapage/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/
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  • From Weddings to Winning Exits: How Kerri Glover Built & Sold a 7-Figure Service Brand
    Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode, Kerri Glover, M&A Advisor at Sagewood and the former founder of one of Colorado’s largest wedding planning firms. Kerri reveals how she went from bootstrapping a solo wedding planning side hustle to building a 20-person team, operating globally, and eventually selling her service-based business for a 7-figure exit. She shares the behind-the-scenes of preparing for a successful sale, covering everything from SOPs and financial clean-up to branding decisions and letting go of founder dependence. Kerri also offers her perspective on the biggest mistakes sellers make, how real estate impacts deal timelines, and what buyers really want in today’s market. Whether you’re building a service business or planning your next move, this conversation is packed with timeless advice on how to turn your business into a valuable, transferable asset. -- With over two decades of experience in the wedding industry, Kerri Glover's journey is a testament to passion, innovation, and entrepreneurial spirit. Her expertise, honed through planning over 1,500 weddings globally and contributing to the creation or redevelopment of 25 venues, is matched only by her insatiable thirst for knowledge. With an MBA from Regis University and a Juris Doctorate from Albany Law School, Kerri brings a unique blend of creative vision and business acumen to every project she undertakes. In 2016, Kerri sold her firm, the largest wedding planning company in Colorado, with Sagewood Advisors, where she is now an M&A Advisor helping others do the same. Kerri Glover on LinkedIn: https://www.linkedin.com/in/kerrilglover/ Websites: https://gosagewood.com/ - https://www.weddingvenuebroker.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/
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  • The 30% Mistake: Why Most Founders Leave Money on the Table with Linda Hamilton
    Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: Linda Hamilton, a Certified Exit Planning Advisor and longtime CPA, shares practical strategies for business owners preparing for a future exit, emphasizing the importance of readiness, clean financials, and documented systems. Key Takeaways: Exit Planning is About Optionality, Not Just Selling Many business owners avoid thinking about exits too early, but Linda argues that preparing early builds resilience and optionality, not just a path to sell. The Cost of Not Preparing Citing a 30% valuation gap between male and female founders, Linda underscores how lack of preparation—especially around clean books, contracts, and succession—can significantly impact sale outcomes. Readiness vs. Attractiveness Linda encourages using assessments to evaluate both how attractive your business is to a buyer and how ready you are to exit. She shares a story of a founder nearly derailing a deal by not securing key employee agreements. Key Indicators of Exit-Readiness - Critical elements include: Clean, audited financials Signed client/vendor contracts Repeatable and documented systems Cash flow visibility and control over AR/AP Transferability & Systemology As a certified systemologist, Linda highlights the importance of mapping your customer journey and operational systems to ensure the business can run without you—critical for buyer confidence and deal value. Building a Support Team Successful exits rely on coordinated advisors: CPAs, attorneys, brokers, and wealth advisors. A SIPA-certified exit planner often acts as the “quarterback” to align everyone's efforts with the owner’s goals. Timing & Purpose Timing an exit is personal. Many owners regret selling too soon because they lack a post-exit purpose. Linda encourages planning for life after the sale as part of the overall exit strategy. Empowering Female Founders Linda advocates for financial fluency and readiness assessments to help women negotiate from a position of strength. Confidence comes from awareness—knowing your numbers, your risks, and your value. Final Advice: Linda wishes she had done her own business readiness assessments earlier in her career, highlighting how early preparation can influence smarter long-term decisions. -- Linda Hamilton is a CPA and CEPA, (Certified Exit Planning Advisor) who is passionate about helping women business owners achieve financial fluency to grow, profit & scale. Linda founded Grow Profit Scale™, a coaching and mastermind program designed to empower women entrepreneurs with financial fluency, profit amplification, and scalable business strategies. In addition to Grow Profit Scale, Linda is also the founder of Linda A. Hamilton CPA LLC, where Linda and her team provide accounting, tax, and strategic financial planning services. With over 35 years as a CPA, CGMA, CEPA, and SYSTEMologist®, she has helped countless business owners develop strong financial systems, improve profitability, and plan for successful exits. Linda on LinkedIn: https://www.linkedin.com/in/lindahamiltoncpa/ Websites: https://www.growprofitscale.com/ - https://www.lahcpas.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/
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  • When to Let Go: The Emotional Side of Selling Your Business – Lessons from Jonathan Bennett
    Want a quick estimate of how much your business is worth? With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business. You might be surprised by how much you can get for it: https://flippa.com/exit -- In this episode of The Exit: Host Steve McGarry sits down with Jonathan Bennett, advisor at Clearly Then and former founder of a successful B Corp consulting firm, to unpack the emotional journey of exiting a business—something rarely discussed, but profoundly impactful. Jonathan shares his own story of selling his company through a gradual management buyout, and how the decision started with a casual walk in Dublin and a question from his wife. The episode dives into the often-overlooked inner challenges that founders face—identity loss, grief, and the fear of letting go. “The easy part is the legal and financial stuff,” Jonathan says. “The hard part is emotional.” You’’ll learn: Why selling at your peak (not in burnout) is critical How to choose the right successor without hanging on too long Why empty promises during a handover can backfire What life after an exit looks like—and how to fill the void with purpose Smart negotiation tips, including how to uncover the real motivations of a buyer Whether you're planning to exit soon or just building for the long game, Jonathan’s mix of practical wisdom and emotional intelligence will give you a fresh perspective on what it really means to walk away from something you built. "Don't wait until you're depleted to sell—get off the stage while the crowd is still clapping." – Jonathan Bennett -- Jonathan Bennett is an advisor and executive coach for purpose-driven leaders who need help solving their organization’s toughest obstacles. With experience in urban, rural, remote, and First Nations communities, Jonathan’s expertise is in social purpose business strategy, governance, branding, change, and communications. His coaching draws on 25 years of creativity and leadership success as a CEO, board member, and founder, and he is known for his deep-listening and his breakthrough solutions that create insights and new strategies. Jonathan on LinkedIn: https://www.linkedin.com/in/bennettjonathan/ Link to Private Podcast: https://clearlythen.com/listen Website: https://clearlythen.com/ -- The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/
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About The Exit - Presented By Flippa

The Exit - Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on https://flippa.com/the-exit-podcast/
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