Cameron Bishop: Why Most Businesses Fail to Sell

21st Century Entrepreneurship

Cameron Bishop is a seasoned CEO turned investment banker, and we spoke about the hidden pitfalls that make otherwise successful companies unsellable—and what entrepreneurs can do to change that. With a track record that includes scaling a publishing company from $7 million to $400 million, acquiring 50 businesses, and helping private owners transition or exit, Cameron shares invaluable insights on building companies that are not just profitable—but also truly sellable.

Throughout our conversation, Cameron reveals five recurring red flags that derail deals, from poor financial records to excessive owner dependency. He speaks candidly about his mission: “I just love helping business owners when they're ready to sell, to give them guidance and hopefully… get them the generational wealth that they hope to get.”

Cameron’s stories—some painful, some triumphant—underscore the brutal realities of the lower middle market and the gap between what owners think their businesses are worth and what buyers will actually pay. As he puts it:

“Somewhere around 70 to 80% of business owners who try to sell their company never sell their company.”

Topics we covered include:

• Why so many $5M–$50M companies fail to close a sale
  
• The shocking truth behind poor accounting—and how it masks real profitability
  
• The dangers of customer and vendor dependency
  
• How gross profit margins can kill interest before a buyer even makes a call
  
• Personal stories of lost deals, bad assumptions, and hard-earned wisdom

Takeaways:
✔ Without accurate, GAAP-based financials, buyers walk away
✔ If your business can’t run without you, it likely won’t sell
✔ “Know what you don’t know—and find an expert to do it for you”
✔ Gross margin is a make-or-break factor for most buyers
✔ Selling your company isn’t just a transaction—it’s a strategic process years in the making

Whether you’re building to sell or just want to future-proof your company, Cameron’s insights will challenge how you think about valuation, succession, and long-term business health.