Think Big

Max Levchin on Entrepreneurship

L-to-R: Tim Schulz, Max Levchin, Ron Pragides

One week after Bigcommerce and PayPal announced a strategic partnership, we were fortunate to host Max Levchin in our SF office.

Max was one of the original cofounders of PayPal where he served as the CTO until its acquisition by Ebay in 2002. In 2004, he helped start Yelp (he is currently Chairman of the Board) and founded Slide (acquired by Google in 2010). Max also serves on multiple company boards including: Yahoo!, Yelp, Evernote, Emerald Therapeutics and Quid. 

Max is currently CEO of Affirm (which he founded) and chairman of Glow. He is a thought-leader and tech luminary from his experiences as a serial entrepreneur, and investor/advisor to startups. He also hails from my alma mater, the University of Illinois at Urbana-Champaign.

We were thrilled that Max accepted our invitation to speak at Bigcommerce. Tim Schulz (our Chief Product Officer) and I facilitated the chat with our team, starting with a tasting of artisanal coffees — a common obsession for those in the tech industry.

L-to-R: Dunkin’ Donuts, Philz Coffee, Mazarine, Blue Bottle.

The conversation was casual and spirited. Discussion topics spanned the gamut: the mission of Affirm, observations on commerce, ideation and investment for startups, and a glimpse into Max’s morning routine. 

We asked Max about how he comes up with ideas for new companies — he apparently has a list of ideas that is constantly growing. Max’s says he gets ideas all the time but perhaps “99.9% of them are terrible”. He first gets excited about a segment or theme. He then digs into the segment and searches rigorously for a “thread” that is ignored by conventional thinking. Max tries to determine if there is a novel (and tenable) idea that hasn’t yet been exploited by others. If these criteria are met, there is the possibility of a viable startup idea.

We also discussed Max’s approach to evaluating startups for investment. He focuses 95% of his attention on the team, and asks himself “are these people awesome?” Max wants to invest in people that are deeply, intellectually curious — because those types are tenacious and won’t be easily discouraged by startup challenges. Max also made an interesting, nuanced distinction between “founders” and “entrepreneurs” . 

When asked about leadership lessons, Max pointed us to this Quora answer as his advice to budding entrepreneurs. It’s filled with great and sometimes controversial insights, like this one:

You can have successful teams where people hate but deeply respect each other; the opposite (love but not respect among team members) is a recipe for disaster.

Max says that he is still learning, and that he has matured as a leader from observing others. For example, he trusts team members more now than he would have earlier in his career. 

Max contemplates the coffee flight.

Max mentioned one childhood nickname and the lesson he learned from it. He also jokingly said that most of his childhood nicknames are…unprintable.

Max also offered to give us espresso-making lessons, and we’ll be sure to take him up on it!

(Watch the full video of our chat here)