Too many investors get seduced by EBITDA and end up buying the wrong business. In this episode, Sam Penny dives deep into what really matters when you're buying: fit. Because even a profitable business will eat you alive if the values, leadership style, or vision don’t align with you.
Drawing from 25 years of real-world experience buying, building, and selling businesses, Sam introduces the Buyer Fit Framework—a simple but powerful tool to evaluate whether a business truly suits who you are and how you lead.
This episode is for anyone who's ever looked at a P&L and thought, “This looks good,” but forgot to ask, “Does it feel right?”
What You’ll Learn:
- Why buyers regret poor fit, not high prices.
- The 4 dimensions of Buyer Fit: Values, Leadership, Skill, and Vision.
- How to spot cultural misalignments before they derail your deal.
- The “soft signals” that tell you if a business is truly right for you.
- The red flags that even seasoned buyers miss (and how to catch them early).
- Practical tools to evaluate alignment and de-risk your acquisition.
Free Resources Mentioned:
- 🔍 Business Valuation Report
- 🧭 Leadership Alignment Tool
- 🛠️ Business Buying Roadmap
- 🎯 Strategy Session with Sam: sampenny.com/strategy
Who This Episode Is For:
- Acquisition entrepreneurs looking to avoid post-deal regret
- Investors moving from theory to real-world ownership
- Operators wanting more than just ROI—they want meaning, mission, and momentum
Final Thought:
When the fit is right, the numbers follow. But when it’s not, the deal becomes a burden. Don’t buy a misfit. Buy a business that fits you.
Popular Podcasts
On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
Crime Junkie
Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.
Cardiac Cowboys
The heart was always off-limits to surgeons. Cutting into it spelled instant death for the patient. That is, until a ragtag group of doctors scattered across the Midwest and Texas decided to throw out the rule book. Working in makeshift laboratories and home garages, using medical devices made from scavenged machine parts and beer tubes, these men and women invented the field of open heart surgery. Odds are, someone you know is alive because of them. So why has history left them behind? Presented by Chris Pine, CARDIAC COWBOYS tells the gripping true story behind the birth of heart surgery, and the young, Greatest Generation doctors who made it happen. For years, they competed and feuded, racing to be the first, the best, and the most prolific. Some appeared on the cover of Time Magazine, operated on kings and advised presidents. Others ended up disgraced, penniless, and convicted of felonies. Together, they ignited a revolution in medicine, and changed the world.