25:32

In this episode of the B2B Growth Blueprint podcast, host Mark Osborne interviews Cameron Bishop, managing director at Raincatcher, a lower‑middle‑market investment bank that specializes in sell‑side M&A for privately held businesses. Bishop shares his unconventional career trajectory—from advertising copywriter to CEO of a $400 million company and finally to investment banker—and explains why a staggering 70‑80 % of owners who attempt to sell are deemed unsellable. The conversation identifies the most common deal‑breakers: heavy owner dependency, cash‑basis accounting that hasn’t been restated to GAAP accrual, lack of repeatable sales and marketing processes, personal brand entanglement, and external pressures such as health issues, divorce, or COVID‑related operational challenges. Bishop outlines a practical exit‑preparation roadmap, recommending owners start planning five years ahead (or at least one to three years) and focus on transitioning from working in the business to working on the business. Key steps include converting financials to GAAP accrual, building scalable sales systems, delegating critical knowledge, hiring or developing a strong second‑in‑command, and creating a clear post‑sale personal plan. The episode emphasizes that addressing these structural and human‑capital issues not only makes a company sellable but also maximizes valuation and yields more favorable deal terms.

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