Lessons I Learned from Joe Lonsdale

Over my career I’ve had the privilege to work with and learn from some of the best entrepreneurs on the planet. Perhaps none was more influential on me than Joe Lonsdale.

I started my career building Addepar with Joe, Jason Mirra, and others. It was a pivotal learning experience for me and changed the trajectory of my life and career. I’ve continued to be impressed by how Eric Poirier and his team have since grown the Addepar platform to over $6 trillion in assets.  

Here are four lessons I learned from Joe that have been invaluable in everything I’ve done since:

Be Bold, Think (really) Big

Joe had previously founded Palantir, solving the most complex problems for governments and businesses. With Addepar, our goal was no less ambitious: fix the issues with the financial system that had led to the financial crisis.

Too many young entrepreneurs try to solve relatively small problems that they can easily understand, code, and take to market. Excellent books like The Lean Startup have become a sort of Bible for this approach, and there are markets where this makes sense.

However, at Addepar we knew we were embarking on a multi-decade mission to truly have a deep, global impact. Indeed, just the core data aggregation and portfolio modeling layers took years to build.

If you look at the PayPal Mafia in general, a key factor in their success has been building incredibly ambitious, contrarian companies in spaces that conventional wisdom deemed impossibly complex. Palantir, Tesla, SpaceX, Addepar and many of the best bets made by Founders Fund and 8VC follow this pattern.

Man-Machine Symbiosis

When you are solving large, complex problems it is unlikely you will be able to develop completely automated solutions. Instead, you need to focus on building systems that work seamlessly with human experts to create great outcomes. Joe taught me much of the conceptual and product development framework around man machine symbiosis and also why it’s so important to solve the more complex problems and markets that have resisted technological innovation to date. 

Since Addepar, I’ve focused on areas like Life Insurance, Medicare, Home Services, and Wealth Management where technology can play a decisive role in a company’s success and better customer outcomes, but only when paired with expert humans. Sometimes human experts are key components of the decision makes process alongside the computer; other times expert humans play a key emotional role in guiding customers through important life decisions.

Recruit A+ Talent

Joe taught me to be a relentless recruiting machine and to keep my standards incredibly high, only hiring A+ talent.

At times this can be exhausting and feel like a distraction, with so many engineers and executives spending half or more of their time in interviews. There is always a temptation to lower the bar and allow borderline candidates to join.

However, the benefits in efficiency and culture that you gain when you maintain an incredibly high standard can't be overstated. 

A+ candidates are interviewing you as you interview them and see the caliber of your team, meaning once the bar is lowered it's almost impossible to raise again.

One testament to this talent is companies Addepar alumni have gone on to build, including Scale.ai (Alex Wang), Scott Wu (Cognition), Opendoor (JD Ross), Vector (Will Chu), and Alloy.ai (Joel Beal).

Authentic Network

When I met Joe, he already had an incredibly deep and broad network, and that has only grown over the past decades. This doesn’t happen by accident. Joe typically replies to emails within seconds, doesn’t forget birthdays, and always picks up the phone. He gives time and value to his network even when there isn’t an immediate financial reason to do so.

 In doing so, he shows authenticity and engenders tremendous loyalty. One of the great unfair advantages of Addepar was our ability to facilitate a high-quality meeting with almost anyone in the world through Joe’s connections.

Meritocracy of Ideas

In coming out of college, I was deciding between joining Goldman Sachs or working (for free) with Joe on the idea that would become Addepar.

The decisive factor in my decision was Joe’s commitment to the meritocracy of ideas. It was clear that he didn’t make decisions based on seniority, but rather on capability and hustle. While at Goldman there was a predetermined 15-year path of seniority-based promotions, at Addepar I was given the opportunity to lead the company as President based on hard work and strong ideas.

There are times when experience matters, but generally hiring, promoting, and making decisions based on meritocracy leads to far better outcomes.