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The Exit – Presented By Flippa
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The Exit – Presented By Flippa

NuevoWhy the Best Time to Sell Is When You're Winning | Betsy Kauffman on Leadership and Maximizing Valuation9 de noviembre de 2026 · 28 min
Episodios
321
Se publica
cada semana
Último episodio
9 Nov 2026

Sobre el podcast

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/

Episodios 321

  1. Why the Best Time to Sell Is When You're Winning | Betsy Kauffman on Leadership and Maximizing Valuation

    28 min

    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 …

  2. Multiple Million-Dollar Exits: Jeremy Schoemaker on Building, Scaling, and Knowing When to Sell

    36 min

    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 …

  3. Building a Business Buyers Want: How to Maximize Your Exit With Natalia Zacharin

    27 min

    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 …

  4. 30 Years to Build, 3 Years to Unravel: Jeffrey House on Ace Cider's $60 Million Exit

    32 min

    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 …

  5. Know Who You’re Selling To: Sequoya Borgman on Private Equity and Preparing for an Exit

    26 min

    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 …

  6. Know When to Walk Away: Elliot Omanson on Exit Timing, Tax Strategy, and Keeping What You’ve Earned

    35 minEpisodio 316

    On this episode of The Exit, presented by Flippa, Steve McGarry sits down with Elliot Omanson, CEO of OWLFI, to discuss the decisions that determine whether an owner walks away from an exit with wealth …

  7. Building a Business That Doesn’t Need You: Heath Adams on Scaling and Selling

    32 min

    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 …

  8. The Trend Is Your Friend: Selling at the Right Time and Avoiding the Wrong Buyer with Matt Bradbury

    28 min

    This episode was recorded prior to the passing of our guest, Matt Bradbury. We are honored to share this conversation and extend our heartfelt condolences to Matt’s family, friends, colleagues, and all those …

  9. Don’t BE for Sale: Mark Mills on Building Leverage and Maximizing Your Exit

    35 min

    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 …

  10. The Charisma Trap: Charles Lee on Bad Investments, Founder Red Flags, and Building Toward an Exit

    30 min

    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 …

  11. Don’t Wait Until You’re Ready to Sell: Andrew Brooks on Building Toward a Successful Exit

    26 min

    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 …

  12. The Tax Efficient Exit: How Charitable Giving Can Change Your Sale with Phoenix Hafen

    32 min

    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 …

  13. An 81-Day Exit: How to Build a Business That Can Run Without You with Dr. Michael Filosi

    32 min

    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 …

  14. The 8-Year Exit Blueprint: How to Maximize Valuation and Avoid Costly M&A Mistakes with Matt Andersen

    30 min

    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 …

  15. From Buying Websites on eBay to 7-Figure Exits: Matt Raad’s Digital M&A Masterclass

    35 min

    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 …

  16. Maximizing Your Exit: Protect More of What You Built with Mark Miller

    27 min

    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 …

    Notas del episodio

    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


    Most entrepreneurs spend years preparing their business for sale, but very few prepare themselves for what comes next. In this episode of The Exit, Steve McGarry sits down with Mark Miller, Managing Director of the Hilton Family Office, to discuss what really happens before and after a business sale. From avoiding costly tax mistakes to building the right advisory team and creating systems that increase valuation, Mark shares practical strategies that can help founders protect more of what they've built.

    They also explore the emotional side of selling a company, why lifestyle planning matters just as much as financial planning, and the common mistakes that cause entrepreneurs to lose millions unnecessarily after closing the deal. Whether you're planning to sell next year or a decade from now, this conversation offers valuable insights for maximizing both your company's value and protecting your financial future.

    Mark Miller is the Managing Director of the Hilton Family Office and CEO of Hilton Tax & Wealth Advisors, where he helps business owners, executives, and high net worth families preserve and grow their wealth using family office strategies. With nearly four decades of experience in financial services, he is a bestselling author and nationally recognized financial expert whose work has been featured in major publications including Kiplinger's, The New York Times, and Money Magazine. Mark specializes in exit planning, tax efficient wealth strategies, and helping entrepreneurs protect what they've built long after the sale of their business.

    LinkedIn - https://www.linkedin.com/in/markmiller-hiltonfo/

    Hilton Wealth Website - https://www.hiltonwealth.com/

    Hilton Wealth Book - https://book.hiltonwealth.com/


    Timestamps:
    [0:01] Episode Preview & Guest Introduction
    [2:19] Mark Miller's Background & Career Journey
    [4:22] Preparing for an Exit: Financial & Emotional Planning
    [8:31] Why Specialized Advisors Matter
    [15:24] When Is the Right Time to Exit?
    [18:27] Increasing Company Value Through Systems & Marketing
    [23:14] Lessons Learned & Hilton Tax and Wealth Advisors


    --
    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/

  17. Culture Shock: The Hidden Trap of Taking Your Company Public with Mike Krupit

    29 min

    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 …

    Notas del episodio
    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 What makes a business truly valuable to a buyer, and how do you know when it is actually time to sell? In this episode of The Exit, Steve McGarry sits down with Mike Krupit, founder and CEO of Trajectify, to unpack the leadership decisions that can make or break an exit. Drawing on a career that includes eight startups, three IPOs, an exit, and four failures, Mike explains why founders who remain at the center of everything can become a liability to their own business. He shares how putting the right people in the right seats, documenting critical processes, building strong systems, and delegating real authority can create a healthier and more valuable company. Mike also explores why the best time to sell is often when the business is performing well but approaching its next major plateau, and why founders need to prepare for what happens after the transaction before signing the deal. Steve and Mike discuss preserving company culture through an acquisition or IPO, communicating with employees when an exit process must remain confidential, evaluating leadership teams from the buy side, and avoiding the culture shock that can follow a major transaction. Whether you are actively preparing to sell or simply want to build a business that can thrive without you, this conversation offers a practical roadmap for creating a stronger, more transferable company. Mike Krupit is the founder and CEO of Trajectify, where he advises entrepreneurs, executives, and leadership teams on business growth, organizational development, and major transitions. A veteran of eight startups, Mike has held roles ranging from CTO to COO to CEO and has experienced three IPOs, mergers and acquisitions, and business failures throughout his career. Since founding Trajectify in 2013, he has focused on helping growth stage companies strengthen their leadership, align their people and processes, and successfully navigate the next stage of growth or an exit. LinkedIn - https://www.linkedin.com/in/mkrupit/ Key Timestamps: [2:36] Introduction and Mike Krupit's Background [2:56] Mike's Startup Journey and Leadership Lessons [4:24] Leadership and Business Valuation Factors [5:48] Preparing a Business for Exit: Documentation and Systems [7:12] Culture Preservation During Exit and IPO [10:03] Evaluating Leadership for Acquisition [11:35] Timing the Sale: When Is the Right Moment? [15:37] Mistakes in Exits and Post-Exit Planning [18:22] Driving Up Valuation: Processes and Leadership [19:30] Team Tactics for Confidentiality and Communication [22:27] IPO vs. Acquisition: Culture and Leadership Changes [26:35] Advice to Younger Self and Current Projects -- 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/
  18. The Strategic Exit Playbook: How ThinkTank Became an Accenture Acquisition with Timothy Lidman

    32 min

    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 …

  19. Secrets to Building a Franchise that Thrives Without You with Scott Jones

    29 min

    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 …

  20. The $14M Secret to Building a Business That Can Run Without You with Richard Stroupe

    33 min

    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 …

  21. The Secret to a Multi-Billion Dollar Exit (And Why You’re Doing It Wrong) with Mike Bennett

    28 min

    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 …

  22. The Hidden Side of Selling: CeCe Leung on Identity, Wealth, and Life After Exiting

    28 min

    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 …

  23. Founder Led Sales Is Killing Your Exit: How to Build a Scalable, Sellable Business with Mike Huey

    32 min

    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 …

  24. Before You Sell: How to Build a Business Buyers Actually Want with Andrew Giancola

    32 min

    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 …

  25. How Smart Debt Helps You Scale & Exit Your Business with Oz Konar

    32 min

    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 …

  26. From Burnout to a Turnkey Exit with Mike Brcic

    28 min

    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 …

  27. From Operator to Investor: Mastering Business Valuation and the Exit Journey with Saul Cohen

    32 min

    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 …

  28. From Patents to Profits: Monetizing IP and Building Newsletter Empires with Victor Varnado

    37 min

    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 …

  29. Franchising Your Way to Freedom: Building Transferable Assets with Gregory Mohr

    29 min

    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 …

  30. Is "Digital Hygiene" Killing Your Valuation? Why Your Biggest Exit Risk Isn't Your P&L with Paige Wiese

    29 min

    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 …

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