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.