How the Best CEOs Delegate
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.Timecodes0:00 – Introduction1:52 – The power of delegation: from the White House to Thumbtack03:13 – Human vs. AI assistants: the future of delegation05:30 – Levels of delegation: from tasks to algorithms07:31 – Principles of effective delegation08:50 – Delegation & productivity hacks10:46 – The future: machine-generated delegation12:36 – Global talent & leveraging international teams13:33 – Assistants and financial leverage14:45 – Company culture across borders16:18 – Assistants as accountability partners17:52 – Coaching, feedback, and the human element19:30 – Goal setting, time management, and prioritization23:07 – Frameworks for founders: time, energy, and meetings26:06 – The efficient path vs. the effect path28:19 – Executive hiring: principles and pitfalls30:19 – Reference check signals 33:09 – Principles for company transparency36:55 – Cofounder relationships & company building39:19 – Chief of staff vs. executive assistant40:06 – Learning from high-performers: Lonsdale, Elon, Thiel, etc.47:10 – Building your universe: org structures and talent networks52:33 – Managing founder psychology & staying in the gameResources:Follow Jonathan on X: https://x.com/swaaansonFollow 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/a16zFind a16z on LinkedIn: https://www.linkedin.com/company/a16zListen to the a16z Podcast on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYXListen to the a16z Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711Please 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 XFind a16z on LinkedInListen to the a16z Show on SpotifyListen to the a16z Show on Apple PodcastsFollow 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.