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.

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.

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.

"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.

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.

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.

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.

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