THE LONGEST GAME YOU’LL EVER PLAY
I think one of the best ways to judge the character of an investor is to observe what they do when a portfolio company fails.
Do they help the founder with the process of shutting down the company?
Do they make intros on behalf of the company’s former employees to help them find new jobs?
Do they help the founder work through such an extremely difficult and emotional time?
What happened when the company first began to struggle? Did the investor just write down the investment and walk away? Or did they jump in to help the business stay afloat?
Investing is a long game – You’re forming relationships with founders and building a reputation that will last your entire career, not just the duration of the company.
My personal philosophy around the long game is simple: When a founder fails, I double down on that founder.
Sending that shutdown email is often one of the most difficult things a founder ever has to do. It hurts. I know since I’ve been there myself. As soon as I get that call/email from a founder, so long as they’ve done everything they said they would do and given their business every possible chance of success, I ask two questions:
What are you doing next?
How can I help?
If they’re a great founder, I want to be their first call for their next venture. After all, most of the greatest founders all failed many, many times before their eventual success.
Empathy and support are two things that differentiate the good investors from the great ones. And, being patient and treating people right are what the long game is all about.