How the Best CEOs Delegate
The a16z Show
Outro
Episode closing, calls to like/subscribe, and informational disclaimers from the show.
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:
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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
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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.
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