How did Nick Kokonas handle due diligence when selling Tock?

Nick Kokonas says he timed the sale of Tock to its COVID growth spurt, before slower growth could hurt the price. Rather than pay an investment bank 3 to 4 percent, his team acted as their own banker for 2 percent at the board's insistence. The buyer's list of 896 diligence questions was expected to take four to six weeks, and he says his team answered it in three days, closing against a March 31 deadline tied to Squarespace's plans to go public.

• Kokonas worked the deal with his CFO and his COO, Jeff Kaplan.
• He says incentives explain most behavior across a deal table, including lawyers billing by the hour.

▸In their words

“And we did that whole list in three days.” Nick Kokonas · at 1:36:44 — open in the transcript →

Source: our own transcription of the episode. The full conversation is on My First Million (2026-10-26). Read the whole episode summary →

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