
24 segments available
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. Timestamps: 0:00 – Introduction 0:44 – The power of delegation: from the White House to Thumbtack 02:13 – Human vs. AI assistants: the future of delegation 04:30 – Levels of delegation: from tasks to algorithms 06:31 – Principles of effective delegation 07:50 – Delegation & productivity hacks 09:46 – The future: machine-generated delegation 11:36 – Global talent & leveraging international teams 12:33 – Assistants and financial leverage 13:45 – Company culture across borders 15:18 – Assistants as accountability partners 16:52 – Coaching, feedback, and the human element 18:30 – Goal setting, time management, and prioritization 22:07 – Frameworks for founders: time, energy, and meetings 25:06 – The efficient path vs. the effect path 27:19 – Executive hiring: principles and pitfalls 29:19 – Reference check signals 32:09 – Principles for company transparency 35:55 – Cofounder relationships & company building 38:19 – Chief of staff vs. executive assistant 39:06 – Learning from high-performers: Lonsdale, Elon, Thiel, etc. 46:10 – Building your universe: org structures and talent networks 51:33 – Managing founder psychology & staying in the game 55:26 – Athena’s vision: human + AI assistants Resources: Follow Jonathan on X: https://twitter.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 a16z.com/disclosures](http://a16z.com/disclosures.
"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 m..."
">> Jonathan, welcome to the podcast. >> Thanks for having me. >> So Jonathan, you're running a massive company. What 4,000 employees? >> 4,000 >> 4,000 employees. You also do investing. You're also in..."
"I some people say, "Hey, you know, Bill Gates is so much richer than me, but he has the same phone that I have." Or I remember um maybe it was you, maybe someone else who was like, "Wait, Obama should..."
">> So, I've had an for many years now and and she's absolutely amazing and um you know I use her for scheduling and u you know typical assistant activities but you have many assistants you know our fr..."
"delegate by algorithm, where you actually export your own internal preferences as you delegate. So, I would say, "Hey, when I plan dinner parties, I like to have six to eight people. I like people to ..."
">> across all of them. >> What are other principles like, you know, I love this delegate bio algorithm, not not by task. What are other principles or frameworks that are really important or non-obviou..."
">> Yeah, it's fascinating. Well, at some point it's going to be, you know, not I don't even have to say it, I just think it. >> Yeah, >> this is uh this is part of our vision uh Athena longer term >> ..."
"about is sort of um international labor some call, you know, labor arbitrage. >> What is the right way of thinking about what people in say the Philippines um can do or can't do verse, you know, assis..."
"finance thing. I'm curious because I I don't leverage mine there. What are the ways that people could get leverage from this because are you are you still interfacing with with the accountants or are ..."
"what it's been like to scale this company where you have and you know you dealt with this thumb thumb too a little bit in terms of just work forces in different areas and how you think about culture b..."
"should be using assistance more for is uh is not only delegation but also accountability of like hey you want to be you know exercising this amount or you want to be spending your time doing XYZ or yo..."
"that have most context on you and they can give feedback on how you're engaging or like you know they can tell you hey you're tired today you know. Yeah, the >> that was my first observation uh when I..."
"don't you maybe we could start with LBD and how you think about goal setting in general and then we can you know bit deeper >> yeah I mean my wife Katherine and I who uh we met as friends one of you k..."
"or principles you live by in terms of time. Like for example, I I believe you put you try to stack meetings in, you know, in a day or in as few days as possible or something. What are what are certain..."
"of my favorite self-help books is the seven effective habits of how effective people and one of their you know principles maxims is this idea of like efficiency with when it comes to achieving uh you ..."
"it, we were like, we're just going to hire the best assistants, match them with clients, and boom, amazing. But we matched the first five assistants, and every single client said the same thing. How d..."
"when you're doing reference checks? What do you really What's the way to get the most signal out of them? >> I mean, what I often tell people is, hey, I'm probably going to hire this person. Uh, and n..."
"transparency with the company like what's information that's helpful maybe going back to thumbtack days what's helpful for the the company to employees to know like what what are principles that that ..."
"go to grad school, but you you know had your buddies from college and you were thinking of starting this this business which wasn't even like a personal pain point. You just thought it'd be a good bus..."
"staff or what's sort of the right, you know, there's sort of this tension between, you know, getting someone younger who's, you know, definitely initially going to do it for for a couple years um and ..."
"know like Lonsdale maybe like a lot or something who have you know chief of staff for like a year or two and then they start a company then they invest in them and they build kind of this reputation f..."
"the right org structure? There's actually no right or structure. It's what's the right or structure for you as a founder and you know Mark Andre and Ben Horowitz are company builders and so they're bu..."
"extensive founder career about uh managing your own psychology, dealing with stress, >> dealing with the cognitive dissonance of, you know, having to present externally like things are amazing even wh..."
"else uh can you share about plugs for the company or things to watch out for or for people who you know want to get assistance, you know? Yeah, look it uh I just say if you don't have an assistant, yo..."