In The Trenches

“Don’t F*ck It Up": Les Trachtman on Avoiding Post-Close Founder Succession Mistakes

Feb 5, 2026
Les Trachtman, seasoned entrepreneur and author of Don't F**k It Up, shares hard-won lessons from four decades of taking over founder-led companies. He discusses how to manage the founder-successor relationship, crafting practical transition agreements, using short mutual renewals as an off-ramp, assessing who to keep or replace, and the value of patience and tactical communication during the handoff.
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ANECDOTE

Honest First Meeting With A Tough Question

  • At his first all-hands Les faced a receptionist who asked, "What if we liked it better before?" and he answered honestly.
  • He asked employees to give the new regime a chance and then "vote with your feet" if unhappy.
ANECDOTE

Field Announcement Triggered Founder Emotion

  • Les renamed a company and announced the new name at a Giants event, triggering an emotional founder objection on the field.
  • The new name later proved successful and the founder came to like it.
INSIGHT

Rolls Change Incentives, Not Always Equally

  • The size of a founder's roll and cash-out both shape incentives but money taken off the table reduces pressure to perform.
  • Roll amounts can be "schmuck insurance" or genuine skin in the game depending on personal context.
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