Buying a business isn’t just about reviewing a P&L and signing a contract. Too many investors discover after settlement that they’ve inherited hidden problems—missing systems, staff departures, or a culture that doesn’t fit. In this episode, Sam Penny (aka The Impossible Guy) breaks down the biggest risks buyers face, how to spot them early, and the safeguards you need to put in place so you don’t get burned.
Sam shares real-world deal stories, the key questions every buyer should be asking, and the practical protections that separate smart acquisitions from costly mistakes.
If you’re planning to buy a business in the next 12 months—or you’ve got one on the radar right now—this session will give you the foresight and tools to take ownership with confidence.
What You’ll Learn in This Episode
- The four core risks that derail business purchases: overstated performance, key person departures, undocumented systems, and cultural mismatch.
- How to test assumptions during due diligence instead of discovering problems post-settlement.
- The questions that reveal hidden weaknesses, including:
- “What are your biggest operational vulnerabilities right now?”
- “Who are the three most critical people in the business and what keeps them here?”
- “What would a worst-case first 90 days look like?”
- Red flags in seller behaviour that signal deeper problems.
- How to protect yourself with smart deal structures: transition plans, retention clauses, escrow/earn-outs, and SOP handover.
- A real-world example of a buyer who uncovered undisclosed staff resignations—and saved six figures by renegotiating.
Resources & Next Steps
- 📋 Download the DealSafe Toolkit – includes a due diligence checklist, key buyer questions, and a transition plan template.
- 🎯 Book a Strategy Session with Sam – review your deal and test assumptions before you sign: sampenny.com/chat
- 🎙️ Keep building your skills with the Built to Sell | Built to Buy Podcast – practical lessons from real-world deals.
Podcast Exclusive!
If you want to work 1:1 with Sam, a small number of spots are available for his loyal podcast listeners. Visit sampenny.com/action to take up this great offer.
Next Episode Teaser
In the next session, Sam dives into one of the most overlooked aspects of acquisitions: intangible assets. Learn how to identify, value, and leverage intellectual property, brand equity, customer data, and proprietary processes—the hidden drivers of valuation and growth.
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