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.