EAs versus chiefs of staff

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.

Timecodes

0:00 – Introduction

1:52 – The power of delegation: from the White House to Thumbtack

03:13 – Human vs. AI assistants: the future of delegation

05:30 – Levels of delegation: from tasks to algorithms

07:31 – Principles of effective delegation

08:50 – Delegation & productivity hacks

10:46 – The future: machine-generated delegation

12:36 – Global talent & leveraging international teams

13:33 – Assistants and financial leverage

14:45 – Company culture across borders

16:18 – Assistants as accountability partners

17:52 – Coaching, feedback, and the human element

19:30 – Goal setting, time management, and prioritization

23:07 – Frameworks for founders: time, energy, and meetings

26:06 – The efficient path vs. the effect path

28:19 – Executive hiring: principles and pitfalls

30:19 – Reference check signals 

33:09 – Principles for company transparency

36:55 – Cofounder relationships & company building

39:19 – Chief of staff vs. executive assistant

40:06 – Learning from high-performers: Lonsdale, Elon, Thiel, etc.

47:10 – Building your universe: org structures and talent networks

52:33 – Managing founder psychology & staying in the game

Resources:

Follow Jonathan on X: https://x.com/swaaanson

Follow our host: https://twitter.com/eriktorenberg

Stay Updated:

If you enjoyed this episode, be sure to like, subscribe, and share with your friends!

Find a16z on X: https://twitter.com/a16z

Find a16z on LinkedIn: https://www.linkedin.com/company/a16z

Listen to the a16z Podcast on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX

Listen to the a16z Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711

Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see http://a16z.com/disclosures

.

Stay Updated:

Find a16z on X

Find a16z on LinkedIn

Listen to the a16z Show on Spotify

Listen to the a16z Show on Apple Podcasts

Follow our host: https://twitter.com/eriktorenberg

Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.