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
Legacy Advisors Podcast
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Podcast Overview
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
Language
🇺🇲
Publishing Since
4/9/2025
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Recent Episodes
July 20, 2025
The Entrepreneur's Exit Playbook - From $13M Facebook Rejection to Successful Exits
<p class="whitespace-normal break-words">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.</p> <p class="whitespace-normal break-words">In this episode, Kris reveals:</p> <ul class= "[&:not(:last-child)_ul]:pb-1 [&:not(:last-child)_ol]:pb-1 list-disc space-y-1.5 pl-7"> <li class="whitespace-normal break-words">Why every business is either growing or being sold</li> <li class="whitespace-normal break-words">The shocking story of PathMap's $13M Facebook deal that never happened</li> <li class="whitespace-normal break-words">Critical differences between strategic and financial buyers</li> <li class="whitespace-normal break-words">Common due diligence mistakes that kill deals</li> <li class="whitespace-normal break-words">His framework for building founder-independent businesses</li> <li class="whitespace-normal break-words">Why mindset trumps strategy in successful exits</li> </ul> <p class="whitespace-normal break-words">Whether you're building your first company or planning your next exit, this conversation provides actionable frameworks for creating optionality and maximizing value.</p> <p class="whitespace-normal break-words"><strong>Resources mentioned:</strong></p> <ul class= "[&:not(:last-child)_ul]:pb-1 [&:not(:last-child)_ol]:pb-1 list-disc space-y-1.5 pl-7"> <li class="whitespace-normal break-words">"The Entrepreneur's Exit Playbook" by Kris Jones</li> <li class="whitespace-normal break-words">Legacy Advisors: legacyadvisors.io</li> </ul> <p class="whitespace-normal break-words"><strong>Kris Jones</strong> 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.</p> <p class="whitespace-normal break-words">Visit legacyadvisors.io for personalized M&A guidance and exit planning resources.</p>
July 9, 2025
Second Chances - What We'd Do Differently
<p class="whitespace-normal break-words"><strong>Episode 10: Second Chances - What We'd Do Differently</strong></p> <p class="whitespace-normal break-words">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.</p> <p class="whitespace-normal break-words"><strong>What You'll Learn:</strong></p> <ul class= "[&:not(:last-child)_ul]:pb-1 [&:not(:last-child)_ol]:pb-1 list-disc space-y-1.5 pl-7"> <li class="whitespace-normal break-words">The emotional preparation required for selling your business</li> <li class="whitespace-normal break-words">Why running a formal M&A process is non-negotiable (and what it cost Kris when he didn't)</li> <li class="whitespace-normal break-words">How legal structure decisions can leave millions on the table</li> <li class="whitespace-normal break-words">The evolution of buyer expectations and market sophistication</li> <li class="whitespace-normal break-words">Strategic timing considerations in today's shifting market</li> <li class="whitespace-normal break-words">Critical preparation steps for founders planning exits</li> </ul> <p class="whitespace-normal break-words"><strong>Key Topics Covered:</strong></p> <ul class= "[&:not(:last-child)_ul]:pb-1 [&:not(:last-child)_ol]:pb-1 list-disc space-y-1.5 pl-7"> <li class="whitespace-normal break-words">Kris's exit story: Pepper Jam to GSI Commerce to eBay</li> <li class="whitespace-normal break-words">Ed's early acquisition lessons and emotional decision-making costs</li> <li class="whitespace-normal break-words">The importance of financial strategy and clean reporting</li> <li class="whitespace-normal break-words">How to maintain leverage throughout the M&A process</li> <li class="whitespace-normal break-words">Industry timing and seasonal considerations</li> <li class="whitespace-normal break-words">Building the right advisory team before you need them</li> </ul> <p class="whitespace-normal break-words">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.</p> <p class="whitespace-normal break-words"><strong>Resources Mentioned:</strong></p> <ul class= "[&:not(:last-child)_ul]:pb-1 [&:not(:last-child)_ol]:pb-1 list-disc space-y-1.5 pl-7"> <li class="whitespace-normal break-words">Free M&A Checklist: legacyadvisors.io</li> <li class="whitespace-normal break-words">The Entrepreneur's Exit Playbook by Kris Jones</li> </ul> <p class="whitespace-normal break-words"><strong>Next Episode Preview:</strong> 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.</p> <p class="whitespace-normal break-words">Connect with Legacy Advisors at legacyadvisors.io for expert M&A guidance and preparation resources.</p>
July 8, 2025
The Hidden Cost of Building a Business: What Every Founder Loses (But Nobody Talks About)
<p class="whitespace-normal break-words"><strong>The Hidden Cost of Building a Business: What Every Founder Loses (But Nobody Talks About)</strong></p> <p class="whitespace-normal break-words">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.</p> <p class="whitespace-normal break-words"><strong>What You'll Discover:</strong></p> <ul class= "[&:not(:last-child)_ul]:pb-1 [&:not(:last-child)_ol]:pb-1 list-disc space-y-1.5 pl-7"> <li class="whitespace-normal break-words">The real investment founders make beyond money and time</li> <li class="whitespace-normal break-words">Why giving everything to your business always comes with a hidden price</li> <li class="whitespace-normal break-words">The psychological and personal costs of entrepreneurship that no one talks about</li> <li class="whitespace-normal break-words">How to mentally prepare for the sacrifices that successful founders inevitably face</li> <li class="whitespace-normal break-words">Bastian's candid insights from years of building and scaling Peak Ace</li> </ul> <p class="whitespace-normal break-words">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.</p> <p class="whitespace-normal break-words"><strong>About Bastian Grimm:</strong> 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.</p> <p class="whitespace-normal break-words"><strong>Perfect for:</strong> Founders, aspiring entrepreneurs, business owners, and anyone who wants the unvarnished truth about what it really takes to build a successful business.</p> <p class="whitespace-normal break-words">This episode contains mature themes about sacrifice, loss, and the psychological challenges of entrepreneurship.</p>
11 total episodes available
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- What is Legacy Advisors Podcast?
- How often does this podcast release new episodes?
This podcast updates daily.
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This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
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Yes, this podcast regularly features guests.
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