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The a16z Show

How the Best CEOs Delegate

The a16z Show

a16z

Science, Innovation, Business, Entrepreneurship, Culture, Disruption, Software Eating The World, Technology

4.41.1K Ratings

🗓️ 10 December 2025

⏱️ 58 minutes

🧾️ Download transcript

Summary

Jonathan Swanson has built two rare successes: Thumbtack, the home-services marketplace, and Athena, the fast-growing platform that pairs ambitious people with world-class personal assistants. Today he runs a 4,000-person company, invests on the side, and raises four kids — all by designing his life around leverage. a16z General Partner, Erik Torenberg, sits down with Jonathan to unpack what that actually looks like. They discuss how elite assistant culture shaped his philosophy, why delegation is a skill most founders never truly learn, and how the combination of humans and AI is redefining personal productivity. Jonathan explains why he believes ambition grows with leverage, not the other way around, and breaks down how he delegates everything from scheduling to search processes to entire life systems. They also get into the future of work, the rise of machine-generated delegation, the expanding role of chiefs of staff, and how founders can design their time around the few things that matter most. It’s a conversation about work, life, and the systems that allow people to operate at scale.

Transcript

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0:00.0

Brian Johnson wants to break the chains of biology. I want to break the chains of time. We can always raise another round or do another trade, but you can't raise another decade. You're running a massive company. You also do investing. You're also happy marriage with four kids. I know the way that you do it all is delegation. What is the secret that you've figured out? Cardinal sin of delegation is that it will be faster or better to do it myself.

0:23.3

And the reason it's a blocker is because it's true.

0:25.5

But the only way you get leverage is by going through that work.

0:28.1

A couple decades ago, you had to be Mark and Driesen, Irvinodikosa, to have a half dozen assistants.

0:34.0

And that costs you half a million dollars.

0:35.6

Now with a company like Athena for $3,000 a month,

0:38.3

you can have your own assistant. What have you learned in your extensive founder career?

0:44.2

Most people think about delegation as a convenience. Jonathan Swanson thinks about it as a system

0:49.4

for living and has built its career around a simple idea. If you don't have an assistant, you are the assistant.

0:55.5

He scaled Bumptack into one of the major home services marketplaces for the last decade.

0:59.9

Now he's doing it again with Athena,

1:01.8

the number one place to hire a personal assistant who can run your calendar,

1:05.4

your operations, your home, and increasingly your AI workflows.

1:09.5

Jonathan is running a 4,000-person company while investing on the side and raising four kids.

1:14.4

The through line is a very intentional philosophy of time.

1:17.7

He believes most people underestimate how much ambition they unlock when they learn to delegate well.

1:22.5

In this conversation, we talk about how elite assistant culture shaped him,

1:26.2

while founders consistently get wrong about leverage

1:28.4

and why he thinks billions of people

1:30.1

will soon be delegating to a mix of human and AI partners.

1:33.6

We get into delegation frameworks,

1:35.8

splitting work across multiple assistants,

...

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