UpTrajectory Review

Roy Dekel's Entrepreneur piece lands on a counterintuitive truth that most small-business owners spend years avoiding: the optimal moment to exit is precisely when the business feels indispensable to your identity. Dekel argues that founders who wait until they are 'ready' to sell have typically already extracted maximum personal value from the company, which means buyers inherit a depreciating asset. The paradox is psychological rather than financial. Most owners conflate their own burnout or boredom with the business's peak value, when in fact these feelings often signal that the founder has stopped investing in growth and the company has begun coasting on past momentum.

For the small-business operator reading this, the practical stakes are immediate and uncomfortable. Unlike venture-backed founders who have boards and investor timelines forcing periodic valuation conversations, Main Street owners often have no external mechanism triggering an exit discussion. The bakery owner, the custom manufacturer, the regional services firm: these businesses frequently represent 60-80 percent of the owner's net worth, yet the owner has no idea what the business would fetch today, next year, or five years from now. Dekel's framework suggests that the 'ready to sell' feeling often arrives after the optimal window has closed, leaving owners with a choice between a fire sale or passing the business to children who never wanted it.

What is genuinely useful here is Dekel's implicit challenge to the narrative of founder indispensability. Much entrepreneurship literature romanticizes the founder who cannot be replaced; Dekel treats this as a liability. The 'smart founder' in his framing builds toward exitability from early stages, creating systems and management layers that make the business attractive precisely because it does not need the founder. This is contested territory. Many small-business coaches still preach 'lifestyle business' optimization, which often means maximizing current owner cash flow rather than building transferable enterprise value. Dekel's view is more aligned with private-equity thinking than with traditional small-business advisory, and that tension is worth examining rather than glossing over.

The downstream effects split sharply by business type. For professional services firms with founder-dependent client relationships, Dekel's advice may be nearly impossible to implement without years of deliberate transition planning. For product businesses or those with recurring revenue models, the paradox is more actionable. The second-order effect worth watching: as more small-business owners absorb this framing, we may see a wave of earlier exits to private equity and search funds, which have been aggressively targeting businesses in the $1-10 million revenue range. This could compress multiples for late-stage sellers while rewarding those who exit earlier in their growth curve, effectively transferring value from long-tenured founders to more transactionally minded ones.

What to do now, regardless of whether you intend to sell in two years or twenty: get a valuation annually, not when you 'need' one. Build a leadership team that meets without you. Document processes that currently live in your head. Dekel's piece is ultimately a prompt to professionalize before you feel urgent pressure to do so. The founder who waits until they are ready to sell has already made the decision too late; the one who builds for exitability builds a better business regardless of whether the exit ever happens. That is the practical kernel worth extracting from the paradox.

“The best time to sell is when you don't want to.” — Entrepreneur

Takeaway: Get an annual valuation and build a team that operates without you before you feel ready to exit.