41: How a Master of Scale Climbed to the Top: Reid Hoffman, investor & entrepreneur

Reid Hoffman is co-founder of LinkedIn, early investor in Facebook, board member at Microsoft, and a member of the "PayPal Mafia."

Reid Hoffman is co-founder of LinkedIn, early investor in Facebook, board member at Microsoft, and a member of the "PayPal Mafia."

There is no one in Silicon Valley who's more connected than Reid Hoffman. That might be because he plays all of the connector roles, sometimes at once.  

He's a venture capitalist, at Greylock. He's an entrepreneur who co-founded LinkedIn, and sold it for $26 billion last year. (Hoffman's net worth is estimated to be north of $3 billion). Now he has a seat on the board of directors at Microsoft. After teaching a class at Stanford, he started a podcast, Masters of Scale, that's about the art and craft of building monster businesses.  

Hoffman is deeply qualified on that subject. He was a founding board member at PayPal, and early on became its chief operating officer. That also makes him part of an eclectic group of characters known as the "PayPal Mafia" former PayPal employees who went on to dizzying success. Members include Elon Musk, YouTube founders Steve Chen and Chad Hurley, investor Peter Theil, and entrepreneur Max Levchin, to name a few.  

I spent some time with Hoffman last week when I flew out to San Francisco to moderate a LinkedIn debate in front of a live audience. It wasn't politics: Reid was debating his friend Tim O'Reilly on the merits of spending gobs of investor money to build startups into dominant forces. 

After the debate, Reid sat down with me on the 17th floor of LinkedIn headquarters to talk about how he scaled from a pre-teen who was ambivalent about school into one of tech's most prolific builders:

That F in French 

In late elementary school, young Reid didn't see the point of class. That might explain how he ended up failing French.

"Once I started realizing I want to build that, I want to accomplish that, I want to participate and help in that kind of mission, in that kind of project, oh – this learning helps me do that. And once I made that connection, I got very focused on learning."

The lesson: Some people need to connect with more than the task if they're going to build great things. They have to see the big picture.

The Case for Diversity  

Hoffman has engaged in the rising conversation about culture and fairness in Silicon Valley by recommending a "decency pledge" that investors would make to founders. It's a subject I've explored with a number of Silicon Valley luminaries lately, as the tech capital's meritocracy facade has shown some cracks lately. 

"You have to start with a recognition that we are not yet the meritocracy we want to be. We are not yet the diverse and inclusive society we want to be. And we should all work toward that together," Hoffman says. How? "Make sure you're putting energy into helping the right high-talent, diverse individuals learn the culture. Whether it's anything from doing podcasts or other things to mentoring or teaching classes."

A Downside of Experience  

It turns out experience isn't everything. In one area in particular, it may have hurt Hoffman's investment portfolio. 

"Knowing all of the ways that PayPal almost died in getting its creation makes me know what the checklist is of, how are you on all these minefields? And so I didn't invest in Square, which is obviously a mistake. I didn't invest in Stripe, which is obviously a mistake. Great founders, great, interesting companies. It was my own PTSD from PayPal."

It's yet another lesson Hoffman has learned – and shared – that involves letting diverse points of view into the room, and remaining open-minded. That is, if you want to grow.