Legacy Advisors Podcast

Kris Jones
  • 5.0 (1)
  • Entrepreneurship
  • Updated Bimonthly

The founders of LegacyAdvisors.io give you direct access to 35+ years of M&A deal-making experience. Kris Jones is a serial entrepreneur, best-selling author, and founder who sold Pepperjam to eBay. He's built a multi-million dollar digital marketing agency and invested in dozens of successful startups through KBJ Capital. Ed Button executed 10 strategic acquisitions at Button Energy, growing it into a $56 million business. He's transformed underperforming companies across energy, transportation, retail, and construction sectors. Each episode delivers tactical advice on valuation, due diligence, and negotiation - protecting what matters most: your legacy. We share real M&A case studies from our 40+ transactions to help you build an exit strategy that preserves your values and maximizes your return. (570)793-2037

Episodes

  1. 07/20/2025

    The Entrepreneur's Exit Playbook - From $13M Facebook Rejection to Successful Exits

    An eye-opening conversation with Kris Jones, serial entrepreneur and author of "The Entrepreneur's Exit Playbook." After successfully selling Pepper Jam to eBay, Kris has dedicated his career to helping entrepreneurs navigate complex exit strategies. In this episode, Kris reveals: Why every business is either growing or being sold The shocking story of PathMap's $13M Facebook deal that never happened Critical differences between strategic and financial buyers Common due diligence mistakes that kill deals His framework for building founder-independent businesses Why mindset trumps strategy in successful exits Whether you're building your first company or planning your next exit, this conversation provides actionable frameworks for creating optionality and maximizing value. Resources mentioned: "The Entrepreneur's Exit Playbook" by Kris Jones Legacy Advisors: legacyadvisors.io Kris Jones is a serial entrepreneur, M&A expert, and co-founder of Legacy Advisors. After 27 years in business and multiple successful exits, including Pepper Jam to eBay, Kris helps entrepreneurs prepare for and execute strategic exits through his advisory firm and bestselling book. Visit legacyadvisors.io for personalized M&A guidance and exit planning resources.

  2. 07/09/2025

    Second Chances - What We'd Do Differently

    Episode 10: Second Chances - What We'd Do Differently In this vulnerable behind-the-scenes episode, Legacy Advisors co-founders Kris Jones and Ed Button Jr. turn the microphone on themselves, sharing the costly mistakes, missed opportunities, and hard-learned lessons from their own business exits. What You'll Learn: The emotional preparation required for selling your business Why running a formal M&A process is non-negotiable (and what it cost Kris when he didn't) How legal structure decisions can leave millions on the table The evolution of buyer expectations and market sophistication Strategic timing considerations in today's shifting market Critical preparation steps for founders planning exits Key Topics Covered: Kris's exit story: Pepper Jam to GSI Commerce to eBay Ed's early acquisition lessons and emotional decision-making costs The importance of financial strategy and clean reporting How to maintain leverage throughout the M&A process Industry timing and seasonal considerations Building the right advisory team before you need them This episode offers rare transparency from advisors who've been on both sides of M&A transactions, providing actionable insights whether you're planning an exit in 12 months or 10 years. Resources Mentioned: Free M&A Checklist: legacyadvisors.io The Entrepreneur's Exit Playbook by Kris Jones Next Episode Preview: Episode 11 features an in-depth discussion about writing The Entrepreneur's Exit Playbook, including personal challenges, tactical insights, and lessons learned that you won't hear anywhere else. Connect with Legacy Advisors at legacyadvisors.io for expert M&A guidance and preparation resources.

  3. 07/08/2025

    The Hidden Cost of Building a Business: What Every Founder Loses (But Nobody Talks About)

    The Hidden Cost of Building a Business: What Every Founder Loses (But Nobody Talks About) In this eye-opening conversation, Bastian Grimm, founder of Peak Ace, reveals the uncomfortable truth about entrepreneurship that most business gurus won't tell you. While we celebrate the hustle, the long hours, and the relentless dedication required to build and scale a business, Bastian exposes what founders actually lose in the process - and why most entrepreneurs are completely unprepared for these sacrifices. What You'll Discover: The real investment founders make beyond money and time Why giving everything to your business always comes with a hidden price The psychological and personal costs of entrepreneurship that no one talks about How to mentally prepare for the sacrifices that successful founders inevitably face Bastian's candid insights from years of building and scaling Peak Ace Whether you're considering starting your own business, currently in the thick of building one, or wondering why the entrepreneurial journey feels harder than expected, this conversation will give you the honest perspective you need. Bastian doesn't sugarcoat the reality - he tells it like it is. About Bastian Grimm: Bastian Grimm is the founder of Peak Ace, a leading digital marketing agency. Known for his direct approach and deep industry expertise, Bastian has built his company into a recognized force in the digital marketing space while learning firsthand about the true costs of entrepreneurship. Perfect for: Founders, aspiring entrepreneurs, business owners, and anyone who wants the unvarnished truth about what it really takes to build a successful business. This episode contains mature themes about sacrifice, loss, and the psychological challenges of entrepreneurship.

  4. 06/17/2025

    What Is Your Business REALLY Worth? A Founder's Guide to Valuation

    "What is my business actually worth?" It's the question every founder asks, but most get the answer wrong. This episode of the Legacy Advisors Podcast provides a masterclass on the art and science of business valuation, moving beyond myths to give you a market-proven framework. Hosts Kris Jones and Ed Button unpack what truly drives a company's worth. They discuss the key variables that influence value, from consistent profitability and revenue durability to the scalability of your leadership team. Learn the critical differences between strategic and financial buyers , understand when to use EBITDA versus revenue multiples , and get actionable advice on how to increase your company's valuation starting today. Key takeaways from this episode: The three main things every buyer looks for when assessing value. Why basing your valuation on emotion or hearsay is a dangerous trap. Strategic vs. Financial Buyers: How their different goals impact the price they're willing to pay. Actionable steps to increase your valuation multiple and build a more valuable business. Debunking the myth that waiting until your business is "bigger" always results in a better offer. Whether you're planning an exit in two years or ten, the insights in this episode will prepare you to secure the best possible outcome. For more resources and personalized advisory, visit us at legacyadvisors.io.

  5. 06/04/2025

    Financial Fitness for Founders – P&Ls, GAAP, and Cash Flow Mastery

    In this essential episode, Kris Jones and Ed Button guide founders, CEOs, and operators through the critical components of financial fitness. They demystify monthly P&Ls, explain the strategic importance of GAAP compliance, differentiate between profit and cash flow from a buyer's perspective, and outline how to build a finance-ready company for future growth, investment, or exit. Why regular P&L reviews and accountability are non-negotiable. How GAAP-compliant financials can significantly multiply your business's value and credibility. The crucial distinction between profit and cash flow, and why buyers prioritize the latter. Actionable steps to ensure your company is financially mature and attractive to investors or acquirers. Financial Fitness, P&L, GAAP, Cash Flow, Profit, Business Valuation, Mergers and Acquisitions, Entrepreneur Finance, Exit Strategy, Business Growth Tune into Episode 7 of the Legacy Advisors Podcast to transform your financial discipline and build a more robust, valuable business. For more insights and resources, visit legacyadvisors.io.

  6. 05/14/2025

    The M&A Checklist That Could Save (or Earn) You Millions

    Ready to sell your business in the next 12 months? Kris Jones and Ed Button break down the ultimate 20-point M&A Checklist that every founder needs. From financial clarity to founder replacement planning, this episode helps you prep for a premium valuation and a smooth diligence process.   One insight from this episode could save, or earn you millions.

  7. 05/07/2025

    Start with the End in Mind | Legacy Advisors Podcast

    What if your exit wasn't reactive—but reverse engineered? In this episode, Kris Jones and Ed Button Jr. dig into the stigma around "exit," how ego kills deals, and what it really means to build a company with an intentional endgame. From Kris's near-sale of Pepperjam to Ed's generational transition at Button Energy, this episode is packed with stories, strategy, and real talk on how to leave your business the right way. Whether you're a startup founder or a family business owner, this episode will change how you think about legacy.

  8. 04/30/2025

    Why Humility Is the Secret Superpower of Great Leaders – With Dr. Matthew Sowcik

    In this episode of Legacy Advisors Podcast, Ed and Kris sit down with leadership expert and best-selling author Professor Matthew Sowcik to explore a powerful (and often misunderstood) force in business: humility. From the underwear analogy to Steve Jobs' transformation, Matthew delivers unforgettable metaphors and insights on how humility shapes confident, resilient, high-impact leaders.   Kris shares how Matthew's coaching transformed his team and personal growth, and Ed gets vulnerable about a humbling failure that reshaped his leadership. Together, they uncover how humility isn't the opposite of confidence—but its foundation.   Whether you're building a company, leading a team, or navigating tough calls, this episode will shift how you think about success, failure, and legacy.   #Leadership #HumilityInBusiness #Entrepreneurship #LegacyPodcast #MatthewSowcik

  9. 04/24/2025

    The Mindset That Separates Good from Great | Legacy Advisors Podcast EP3

    In this powerful episode of Mindset Matters, hosts Kris Jones and Ed Button Jr. dive deep into the mental game of entrepreneurship that truly separates good business leaders from great ones. The hosts kick off with their "Mindset Minute" segment, where Kris explores how confidence serves as the foundation for all entrepreneurial success. Drawing from his experiences with Tony Robbins' events, he shares how physiology and breathing techniques directly impact your mental state and decision-making abilities. Meanwhile, Ed introduces his "failing forward" philosophy, explaining how embracing failure as a learning opportunity has helped him build resilience throughout his business career. In the "Resilience Rundown" segment, the conversation turns personal as Kris reveals the challenges he faced while building a startup with comedian Damon Wayans Jr. – a venture that was thriving until COVID-19 brought live entertainment to a standstill. Rather than giving up, Kris shares how they pivoted their business model to survive. Ed counters with his own story of acquiring a business that quickly went sideways when employees began sabotaging client relationships, offering valuable insights on how to weather serious business storms. The final segment, "Life Hacks for Leaders," delivers practical productivity strategies that have helped both hosts maximize their effectiveness. Kris breaks down Tony Robbins' Rapid Planning Method (RPM), explaining how to structure your time around outcomes rather than tasks. Ed shares his non-negotiable morning routine – including cold showers and technology-free family time – that sets him up for peak performance throughout the day. Whether you're launching your first venture or looking to level up an established business, this episode delivers actionable wisdom from entrepreneurs who've navigated both spectacular triumphs and devastating setbacks on their journey to success. 👉 Visit https://legacyadvisors.io/podcast for more episodes, exclusive content, and resources to help you build the right mindset for entrepreneurial success!

  10. 04/16/2025

    Due Diligence Nightmares, and $100M Decisions | Legacy Advisors Podcast

    What's TikTok really worth? Why does due diligence feel like a financial colonoscopy? And how do you know when it's the right time to sell your business — or double down? In this episode of the Legacy Advisors Podcast, Kris Jones and Ed Button Jr. unpack the M&A headlines (starting with the TikTok chaos) and get brutally honest about what it takes to scale, acquire, and exit like a pro. 🔥 Featured in this episode: The Deal of the Week: TikTok's potential U.S. sale, who's bidding, and what's at stake Why the algorithm may never leave China — and what that means for valuation A raw behind-the-scenes story from Kris about almost losing the Pepperjam deal Ed's freight acquisition gone sideways (and what he learned from it) A deep dive into due diligence — how to prepare, what to expect, and how not to get blindsided "Sell or Stay": A $10M SaaS founder scenario that every entrepreneur should hear What's the difference between growth and scale? (Spoiler: most founders confuse the two) This one's for the owners in the trenches. The ones building with an exit in mind — but legacy at heart. 💬 Leave us a review if this helped shift your perspective. 📩 Learn more about our work at LegacyAdvisors.io 📱 Follow us on Instagram, LinkedIn, and YouTube @LegacyAdvisorsPodcast

  11. 04/09/2025

    Legacy Over Revenue: What Really Matters in Business | Legacy Advisors EP01

    In this debut episode of the Legacy Advisors Podcast, co-hosts Kris Jones and Ed Button Jr. lay the foundation for a show built around more than business, it's about story, values, and building something that actually lasts. They share war stories from the trenches: • How Ed grew a fourth-generation family business from 2 million to 130 million gallons through smart M&A and roll-ups • Why Kris turned down early offers and ultimately sold Pepperjam to eBay (after learning M&A the hard way) • What happens after the exit, and why so few entrepreneurs talk about that chapter • Why financial literacy is the founder's most underdeveloped superpower • The hard truths about scaling, hiring, cash flow, and the myth of "if you build it, they will come" Whether you're just getting started or you're gearing up for a sale, this episode offers raw insights from two operators who've lived it, and built legacies of their own. About Legacy Advisors Podcast: Hosted by Kris Jones and Ed Button Jr., Legacy Advisors explores what it means to build, scale, and secure your business legacy. We talk M&A, exits, leadership, and the messy reality of entrepreneurship, with no fluff, no filters. 🔗 Listen or watch on your favorite platform: https://legacyadvisors.io/podcast

  • 11 Episodes

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About

The founders of LegacyAdvisors.io give you direct access to 35+ years of M&A deal-making experience. Kris Jones is a serial entrepreneur, best-selling author, and founder who sold Pepperjam to eBay. He's built a multi-million dollar digital marketing agency and invested in dozens of successful startups through KBJ Capital. Ed Button executed 10 strategic acquisitions at Button Energy, growing it into a $56 million business. He's transformed underperforming companies across energy, transportation, retail, and construction sectors. Each episode delivers tactical advice on valuation, due diligence, and negotiation - protecting what matters most: your legacy. We share real M&A case studies from our 40+ transactions to help you build an exit strategy that preserves your values and maximizes your return. (570)793-2037

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