A Few Things We Learned From Daniel Gross

Daniel is the Founder of Pioneer and runs Y Combinator’s AI track. He is an early investor in Cruise, Gusto and Opendoor. Below are some investing lessons from our session with Daniel.

Don’t belabor decisions; either pass or figure out what else you need to know

“I’ll sleep on it” doesn’t work. It’s rare you go to sleep and magically have the answer. So you should quickly determine next steps after meeting with a founder.

Daniel tries making a hypothetical investment decision within 5-10 minutes of starting a pitch meeting. If he’s excited, Daniel then figures out what additional information is needed to proceed with the investment. This helps focus the conversation and the diligence afterwards.

If he’s not excited, Daniel passes quickly. This is beneficial for all parties. Nobody wants to be left hanging.

You can talk your way into later rounds, even if you passed on the seed

Some investors write dozens of $25K seed checks, hoping this lets them access later rounds of the winners. Daniel doesn’t believe in this approach.

As a smart angel, you should be able to make friends with top founders and get allocation in their rounds. You don’t need to buy access by investing earlier on.

Spearhead is a program that funds and mentors founders so they can start angel investing. Founders get exclusive access to masterclasses from investors such as Daniel Gross. Spearhead is currently accepting applications for the 2019 cohort. Apply by Oct 31.

A Few Things We Learned From Daniel Gross