What happens when you’re the biggest asset in your business - and the biggest liability to its sale value?

In this episode of Buyers’ Frenzy, host Will Lindstrom sits down with exit planning advisor and business coach Len Breskowitz to unpack one of the most common- and costly - deal killers: owner dependency.

Len explains why a business that can’t run without its owner is essentially worth nothing to a buyer, and how his “two-week vacation test” quickly reveals the level of risk.

They discuss practical ways to reduce that dependency, including Len’s “80% rule” for delegation, step-by-step approaches to building owner independence, and the critical importance of defining your “next big adventure” beyond business ownership.

The conversation also covers the emotional and strategic sides of letting go, the surprising gap between owner expectations and family succession reality (50% vs. 25%), and why early, open conversations with family - ideally three to five years before a transition - can prevent valuation surprises and conflict.

Len also shares a simple way to explain valuation and risk to family members so everyone understands their role in protecting and increasing enterprise value.

Highlights Covered:

• Why buyers avoid businesses tied too closely to their owner
• The “two-week vacation” litmus test for sale readiness
• How the 80% rule helps owners delegate effectively and reduce dependency
• The emotional side of letting go and owner identity after a sale
• Why early family conversations (3–5 years in advance) prevent exit surprises
• The gap between owner expectations and reality in family succession (50% vs. 25%)
• Building an advisory team to guide the exit process
• Explaining valuation and risk in simple, relatable terms

Whether you’re years from selling or actively preparing for an exit, this episode shows why your ability to step away may be the single best indicator of your company’s value.

Have insights on “Deal Killers”? If you’re a CEPA, CPWA, CFP, or fiduciary with experience navigating the hidden risks that derail deals, we’d love to hear from you. Connect with us on LinkedIn or at theculturethinktank.com/contact