How to Know If the Business Is Right for You - Sam Penny | Business Coach for Owners & Investors

How to Know If the Business Is Right for You

Buying a business isn’t just about the numbers. It’s about fit. In this article, based on our recent Built to Buy webinar and podcast, you’ll learn how to evaluate whether a business is truly right for you — beyond the spreadsheets.

Why Fit Matters More Than Function

Not every good business is a good fit. A company might have strong revenue, low churn, and loyal customers, but that doesn’t mean it’s the right business for you to own and operate. This is about more than operational success — it’s about personal alignment. If the business culture, pace, or leadership style clashes with yours, you’ll feel friction daily. And that’s where regret starts.

The Four Layers of Buyer Fit

We use the Buyer Fit Framework to assess alignment across four critical dimensions:

  • Values Fit – Does the mission and culture match your worldview?
  • Leadership Fit – Will your leadership style work with this team?
  • Skill Fit – Do your strengths match what the business needs next?
  • Vision Fit – Can you see your life in this business 2–5 years from now?

Values Fit: The Most Overlooked Factor

Most founders build from a deep belief system, whether they state it or not. If you don’t share that belief, leading the business becomes exhausting. Look at how they make decisions, talk about their customers, and define success. That’s where values show up — and where they need to align with yours.

A Real-World Misfit: What Happens When You Get It Wrong

One buyer acquired a business with great financials. But within 90 days, team members quit. Culture clashed. Growth stalled. They underestimated the values mismatch — and it turned a 3.5x deal into 5x the work. Eighteen months later, they sold — exhausted. Lesson: The wrong fit destroys more than just morale. It wrecks momentum.

Clues That Reveal Fit (Or Misfit)

  • Team interactions: do they lean in or hold back?
  • Founder conversations: open and aligned or guarded and misaligned?
  • Brand tone of voice: bold, reserved, chaotic, precise — does it match how you operate?
  • Customer reviews: what are clients praising?
  • Business rhythm: fast-paced or methodical — and do you thrive in that?

Red Flags to Watch

  • Feeling the need to “fix” the culture immediately
  • Disrespecting how decisions are made
  • Rationalising misalignment during due diligence
  • Wanting the spreadsheet, not the people

These are signs you’re headed for friction — even if the numbers look good.

Questions to Ask Before You Sign

Don’t just analyse the business — interrogate your own response to it. Ask:

  • Could I lead this team today without the founder?
  • What would energise me about this business?
  • What would frustrate me within 3 months?
  • If I had to hold this business for 5 years, would I still want it?

Tools to Help You Decide

Further Reading

Recap: The Right Business Is Personal

  • Fit matters more than financials
  • Use the Buyer Fit Framework
  • Trust your instincts — and back them with evidence
  • Decide based on the life you want to lead — not just the return you want to make

Listen to the Podcast Episode

🎧 Catch the full session as a podcast: Built to Buy | Episode: Is This Business Right for You?

Book a Strategy Call

If you’re even thinking about buying, let’s make sure you’re buying the right business. Book your 1:1 call now and get expert eyes on your deal.

 

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