Do the prenup: have the investor conversation before you need it
An investor who had just come on board attempted a hostile takeover of Shane Chanel's business. His advisors had warned him. He did not want to upset them.
Shane Chanel's hardest lesson as a Founder came from an investor who had only just joined the cap table, and who then attempted a hostile takeover of the business.
His read on what happened is unsentimental. At some point the maths changed for them. Five per cent of something that might be worth a billion in a few years started looking less attractive than a hundred per cent of twenty or thirty million now.
The advice he did not take
This is the part worth sitting with. Shane's advisors had told him to put protections in place. He knew what to do.
He did not do it, because the investor had only just come on board and he did not want to upset them.
Do the prenup
You do not get married expecting it to end. You do the paperwork anyway, while everyone still likes each other and nobody has anything to defend.
The same applies here. The moment to agree what happens if things go wrong is the moment when nothing has.
Why these conversations feel like an accusation
Geo's admission on the episode is that he hates conversations about contracts and worst-case scenarios, and that early in his career he simply avoided them. He has regretted it more than once.
That is the actual obstacle. Raising it feels like signalling distrust of someone who has just backed you, and there is always a reason to leave it another month.
Shane's version of the fix is unglamorous: set the boundaries, set the expectations, and then follow up on them. The following up is the part people drop.
What to write down
Take the worst-case scenarios and put them on paper before they are live. What happens if someone wants out. What happens if you disagree about selling. What each person is actually building toward.
Founders who agree up front that they are building to exit, and write it down, are protected by that document on the day one of them changes their mind.
The cost of having the conversation is a few uncomfortable minutes with someone who just wired you money. The cost of skipping it is defending your company from your own cap table.