My $100M Mistake + 6 Company Exit F**k Ups To Avoid (#522)

Sam Parr says QSBS can materially change the after-tax outcome of an exit, but many founders learn about it late. He and Shaan Puri describe timing (holding period) and entity/eligibility constraints as reasons you need to structure early if it might apply.

Shaan Puri recounts shutting down a sticker/avatar app without attempting to sell it, later seeing a similar product (Bitmoji) sell for $100M. His point is to at least run a short, intentional process to explore potential buyers before deciding to kill a product.

Sam Parr describes how wanting an exit too badly weakened his negotiating position, because buyers can sense emotional urgency. Both hosts frame the core antidote as being truly okay with no deal (including having other options and/or committing to continuing to run the business).

Shaan Puri explains that the “best” offer isn’t necessarily the highest number, using Milk Road’s sale process and a “discount factor” concept for close probability and stability of terms. He emphasizes judging counterparty quality, red flags, and likelihood to close, not just headline price.

Both hosts stress that corporate development is often not the true decision-maker, and Shaan Puri says you need to identify the internal champion and their motivations. They argue you’re effectively selling to a specific person with a need, not to a faceless corporation.