Timing Your Sale: Lessons from The Founder’s Dilemma

Inspired by HBR’s “The Founder’s Dilemma” by Noam Wasserman, this article explores the critical choices entrepreneurs face when completing a sale.

The Cost of Holding on Too Long

Wasserman’s research highlights a common pattern: founders often delay their exit, risking their opportunity to maximize value. Emotional attachment and fear of change are frequent drivers of hesitation.

Wasserman frames the dilemma as a choice between being “Rich” or “King”.

  • The “Rich” path involves giving up control to increase financial return.
  • The “King” path prioritizes control—even if it comes at the cost of valuation or investor interest.

Many founders try to straddle both paths, but indecision can lead to a delayed or suboptimal exit.

Clarity Brings Confidence

Achieving a successful exit—financially and personally—requires clarity. When founders define their priorities early, they lay the foundation for confident, informed decision-making.

Clear priorities help founders:

  • Evaluate Potential Buyers more Objectively: Assess buyers based on long-term compatibility rather than just price
  • Set Realistic Expectations: Establish achievable goals regarding valuation and deal terms
  • Navigate the Exit Process: Approach the exit with confidence instead of uncertainty

By aligning personal goals with transaction outcomes, founders can reduce friction and increase the likelihood of a successful exit. 

The Hidden Costs of Delaying an Exit

While gaining clarity around your goals is important, so is timing. Postponing an exit can result in missed opportunities and in some cases, diminished returns. Research indicates that Founders who wait too long to sell may encounter deteriorating valuations, increased competition in the marketplace, or personal burnout.

In Conclusion

At Perseus, we embrace a buy-and-hold model that prioritizes long-term stability. Our mission is to protect your company’s unique identity and provide the support needed for its success.

The most successful exits we’ve seen are led by Founders who knew what they wanted, stayed open to timing, and partnered with acquirers who understood their values.

For a deeper look at how to prepare your business for a successful transition, read blog 7 Steps to Prepare Your Software Business for an Exit. 

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