Leaning in, doubling down

What I’ve learned from the greatest asset allocators in the world:

For decades, Angel investing has been viewed as a series of one-shot decisions.

The vast majority of angel investors will meet a founder, conduct their due diligence, and make a one-time decision to either cut a check or not, then walk away or wait until the company is bankrupt or public.

But it doesn’t have to be that way.

The most successful public equity investors show us that the best investments are the ones where you build an increasingly large position over a long period of time.

Angel investing doesn’t have to be one-and-done.

Instead, you can take the approach of actively managing your portfolio of startup investments.

Write small checks at the very beginning with the understanding that, for the ones that you “picked right”, you’ll want to invest much more in that company over the long term.

This frees up capital to make a higher number of investments on the front end while making fewer and more select investments in the companies that show repeated success on the back end.

It’s a lot like investing in a public company, and it’s one key to producing outsized returns for yourself and your investors.

When you see things working, lean in, double down, and continue to invest!