Stop Generating, Start Thinking with Kevin Henrikson

0:00If you were in a car accident today or tomorrow, and you're like, man, I've got to go to the hospital, I'm going to be out of touch for three days, you would just have to cancel all your meetings. and people would understand. And I'm like, you kind of need to create that ability for yourself or give yourself permission to sort of have a car accident periodically where you're like, I just need two days to like think about stuff.

0:22Picture this. You open up a new AI conversation and prompt your way to five new versions of the same document. Even after reading every one of them, you end up more confused than where you started. AI promised to make us productive. Instead, we're drowning in outputs with real progress flatlining. Today's guest is a founder who's built and sold companies for hundreds of millions of dollars. He's scaled engineering teams at companies like Microsoft and Instacart, and now he's calling bullshit on the productivity myth we've all been sold. The solution isn't another AI tool. It isn't a perfectly engineered prompt.

0:54It's learning when to stop generating and when to start thinking. Kevin, welcome to the show. Thanks, Paul. I appreciate you having me. So I want to get your insights on AI chaos. There's a story you wrote from 2005 when you presented Zimbra at the super happy dev house. And I watched the video and it's you like late at night, super dark. I'm sure somebody's holding a camcorder. Yeah. First, like what's a hacker house like in 2005? Dude, it's crazy. So yeah, there was this guy, David Weekly. He's still like a big exec at a bunch of tech companies here, also a pilot. So we've connected through pilot forums, you know, reconnected 20 years later.

1:30but yeah he had had this house in hillsborough and um it just started with kind of like friends coming over and writing code talking about what was going on in the internet again this is like pre sort of mobile wave pre all the things it was like just the early days of kind of web 2 javascript those kind of things where we were starting to do some more dynamic web apps and people were just hacking around with that and blogging and so the hack it was literally like Just a bunch of kind of smart people getting together, working on things, and then sharing their projects. And part of that was some of them were startups.

2:05Some weren't even companies. They were literally just ideas. You would kind of go in there and work on your thing and show people what you're working on and how you're integrating with something. And there was this word mashup where people had sort of figured out that you could use JavaScript to connect different applications. And so you could write a web page and have it connect to other web pages through this kind of like really early days of APIs and early days of JavaScript. And so that was kind of what kicked it off. And a lot of people were working in that mode. But we were working on Zimbra.

2:35It was a small startup at the time. And I was kind of doing developer relations. And I kind of went to this house to kind of like look for people to integrate with us and kind of see what we were building and show some of the stuff that we had done. And then ended up there. It's like, hey, there's a demo. And I'm like, cool. I'll just throw my name on it. and yeah, ended up demoing. And like I said, you saw the projectors kind of essentially somebody grabbing a phone in the back and taking pictures. And it was Cal Newport actually, which is crazy. He's wrote a bunch of famous books on productivity now that was taking most of those pictures and posting them to a website called Flickr, which Yahoo ended up acquiring.

3:11And yeah, so kind of a crazy blast in the past. If you look back, what made you a builder? Like what motivated you to go to a hacker house? Like what is it in Kevin that makes him wake up every day and build this stuff? Yeah, I mean, I've just crazy curiosity. I mean, even when I grew up, I grew up on a pig farm and I would just go outside and work on things. And my mom always used to joke that you would spend more time working on stuff than actually using it. So I'd spend a week trying to fix this go-kart, ride it for 10 minutes, wreck it, break it, whatever, and then spend another three weeks putting it back together, reassembling it, changing engines, taking an engine off a lawnmower to rebuild it.

3:46And so I always just had this curiosity of how things worked. And I think when you do that with mechanical stuff, there's a certain speed to it. And then with digital and internet, it just went so much faster that you could just build and do so many things. And so, yeah, the Zimber thing was like, man, I was just curious where other builders were and like wanted to go see what they were doing. And quite frankly, it was trying to kind of be like a marketer in disguise, like kind of had this sales angle of like, hey, if I could get more people using our stuff, then that would be better. It was this whole open source movement back then where everybody was like building in public and things like that and more in the open source way and not in the like building in public marketing way and Twitter way, which people talk about today.

4:24And so, yeah, it was just curiosity combined with like an interest to show people cool stuff and have engaging conversations. You know, AI is everywhere and building is fast. It's accelerating more and more. What's changed and what stayed the same? yeah so for me i mean if anything the curiosity is kind of like cranked it up like i mean right now i can look at my browser i've got four chat chpt tabs and two manis windows and probably three of those are active like they're just running on stuff that i keep giving it and so like you're constantly nudging prompts and so i think the idea of being able to hyper paralyze your ideas and thoughts and sort of become curious and get a way more synthesized view and learn things just way faster.

5:09So like in one tab, for example, I'm asking about some company we're looking at in another tab, crafting like a proposal to sort of understand like how we're going to go re-architect one of our features. And then in a couple others, I'm like asking about like my diet for this week. I'm like, what am I going to change what I'm going to eat? And like, I was like, no, there's nothing in the fridge. I'm like, man, what should I get for food? And then, so I like, I just ripped off a tab. I'm like, Hey, what should we order this week? And so to me, that sort of hasn't changed the curiosity, but what has changed is the ability to sort of like unbridled sort of energy where you can just keep asking questions at nauseam.

5:42But I think, you know, sort of to the post and what we had talked about was that like, because of that, you end up with a lot of, you know, scattered ideas. And so you need to find time to say, okay, let me sit down and be calm and synthesize. And I was telling a buddy of mine once, I had this idea where, you know, most of my cars are Teslas and they're all connected. And I walk out with my phone and I drive it and I push the button and it auto drives me and it's like, you know, all the AI, everything. And one day I have one car that's like a hybrid kind of a gas car essentially. And so I walked out there and I just literally had the key, no wallet, no phone, no, no, I had taken off all my trackers and they were charging.

6:18So like none of my connected, I was literally kind of naked in the, in the like digital sense. I literally just had the physical key to unlock this car. And I'm like, Oh, I'm just going to run down and grab something from the store. And I got out of the car and I was like, you know, didn't have my phone. And I was like, kind of like, Oh, that's weird. And I'm like, Oh, wait on my watch. And there was this first sense of panic. Like I lost my like sort of pulse. But then as I started walking around the store, I was like, holy shit, this is kind of amazing. Like there's this level of calmness of like, this is what it's like to not be sort of like constantly jacked into the internet and with multiple devices syncing.

6:51And I've done this twice now where we have the team or do a dinner and be like, Hey, everybody just take off all your devices and just like literally a device free sort of environment. And it completely changes it. It like brings the humanness back to things. And so I think that part of it is, you know, what's changed, but also probably has some negative connotations of like the fact that we're always just jacked into like the internet in real time. It reminds me of walking into a Lunch and Learn. It must've been a long time ago. And there was this founder at the startup that Microsoft had just purchased.

7:23And he was gonna teach people what it was like to be an entrepreneur. And like, I still remember it like it was yesterday. And you put up this slide that showed your calendar. It was just a screenshot of your calendar. I said, on Mondays, I have a team meeting and on Friday. And the rest of it was blank. Tell me about focus. In a world where we're always distracted, to your point, and always like, if you want to be successful, you've got to hustle and grind. Tell me about your philosophy around focus and how you think about productivity. Because that, to this day, still sticks with me. Yeah. And it's funny because my thinking on this continues to evolve.

7:57How do I do efficiency? How do I delegate all these things? And what's funny is like when I think back, like before that talk, I was the like code late at night, sleep under your desk kind of model in my 20s. And then my 30s got a little smarter. And now in my 40s, the biggest unmovable meeting every day on my calendar is sleep. It says 8 p.m. go to sleep, 5 a.m. wake up or 4 a.m. wake up, depending on the day. When I travel, that moves. And so I know like I'm on East Coast, in Asia, like in Europe, I move that, my admins move that sleep blocker. And it's like, no, no, I just don't compromise on the sleep thing.

8:30And it's like, if it's going to be out late, I'm just not going to do it. I'm going to go home and sleep. And so I think the calendar day time, I think I've adjusted. And so like, I still have these free time blocks. And I joke, if you were in a car accident today or tomorrow, and you're like, man, I've got to go to the hospital and be out of like touch for three days, you would just have to cancel all your meetings. And you would be like, and people would understand. And I'm like, you kind of need to create that ability sort of for yourself or give yourself permission to sort of have a car accident periodically where you're like, I just need two days to like think about stuff.

9:02And that to me is like still something that's pretty powerful. I try to build in blocks of that every week and then periodically take like a couple days where you're like, hey, I'm just going to do nothing. And it's weird now because I have like a sales calendar for some of the stuff that we're selling. And I let people book meetings on Saturdays and Sundays. And surprisingly, people will book them in the mornings. But then, you know, I'm like, okay, if that's a good time for them, I'll take those meetings. And then I'm just not going to work Tuesdays. You know, I sort of like trade it off where it's like, you can't do the 996 thing that we talk about.

9:29You know, these people are working nine to nine, six days a week. And I'm like, yeah, you're just not as effective in the last hour of that nine to six sort of schedule. We both have kids. You know, I watch them kind of navigate the world. I'm sure you do. And you look at the distraction and the technology and everything. Similar to your trade-offs in your sleep and those sort of frameworks, what are some of the things you're implementing at home? It's interesting because when the kids were really young, like they were sort of the iPad generation, right? My daughter knew how to use an iPad at two years old.

10:02She's now, she just turned 16, the youngest. COVID changed this because I saw a lot of kids struggle with COVID coming out of that, kind of leaving high school, going to college and not having sort of a transition of like, what does life look like and going to COVID and into these things and not learning the life skills. And so my rules with her are actually pretty loose. Like I'm like, you know, what time should you be at? I'm like, you tell me. And then, you know, have her using things like Lyft and Uber early. She uses those on her own now. And I think the other thing that's interesting is the phone stuff is like, you can take the phone away and lock them out of their digital footprint, but then they go to college and then you're like, okay, wait a minute.

10:42Now, like you never knew how to like self-modulate on the phone. So I'm kind of like, let it go. And if you sleep into school or you sleep through your class, it's better to learn that in high school where you have the guardrails of people kind of watching you for in college, if you sleep through a bunch of casts and miss it, nobody's going to call you. Right. And so I think that's one thing where I've kind of arguably let the boundaries out in the sense that like, if I thought of when I was a kid, I was driving tractors at nine years old, like, you know, on a farm and like there was no rules.

11:09Like I'd go out and just fire the welder up and arc the thing and be like, wow, that, that didn't work and like have to go fix it most city kids don't have those experiences today because they're not in that physical world that their devices are thing and i think the other one that this is controversial i think it sometimes but i'm very very strict i'm making sure that kids drive i've seen a lot of teenagers make it all the way through high school and some into college and never get a driver's license because they don't need it right they're either at a walkable location they're getting rides from their friends they're using lyft and uber and again like there's ones that just barely get the driver's license and never use it.

11:44And there's ones that don't get it. And I think both of those lack confidence to actually navigate the world in a way that I think is going to be required. And so that's one thing that I'm very hard on. Like, you got to get your driver's license right away and you got to go drive. You have a permit now. I don't drive anymore. You want to go somewhere? I'm like, great, grab the keys. Let's go downstairs. I'll sit in the passenger seat and we'll drive you and we'll go. And then that's it. And she's like, well, I don't feel like driving. That's cool. And we're not, I don't feel like going because that's real life and I think my view is that now she's through that hump and she's like about to get you know gonna take her driver's test in a few weeks and and so I think to me the kid thing is like almost going back in a weird way to our parents and not helicoptering and not giving them over protections because it's just too easy to like track everything what they're doing on their phone and I can I used to block everything in the early days and now I'm like what's the point like at some you know when she's 18 she can just clear the like apple protector and she's free to go And I'm like, well, why don't we let that happen when she's 16 or 15 and kind of figure out what her boundaries are and understand that self-modulation.

12:43So I think driving and sort of releasing those sort of like really strict rules. And again, you know, every kid's different. Like people have different abilities to sort of self-navigate. I'm sure there's people listening that are like, dude, you're insane. My kid wouldn't be able to do that. Great. Then that's a personal thing. But I think my personal thing is like, look, we should start to simulate college. It's like, I don't do your laundry. I don't cook your food. Hey, the food's in the fridge. What do you want to order? we'll go to the store together. In fact, you'll drive me to the store, we'll buy the things and come back and you know, we can cook it.

13:10Because I think a lot of that teaches a set of resilience that if you end up in college, and you're like, only no way to get food is to click DoorDash, or buy Lyft or Uber to go to a restaurant, like I'm like, or go to the mall, right? It's just so easy to go to the mall and have 20 things to pick from. And I'm like, yeah, that works. But that's not real life. Like it's you're gonna have to figure things out. And same thing, having them travel alone, go to airports, flying in different, you've got to learn those things. And I'd much rather learn that where there is sort of the protective of the home that, hey, eventually you are going to end up in a bed and back at home with your parents versus, yeah, I think learning that for the first time in college is a lot trickier.

13:44And partly because kids are way less prepared with real life than, man, I was debating with other farmers that are 60, 70 years old as like a 15 year old in high school. Like, cause that's just the way it was. Like I would drive the truck over, load up two tons of corn, negotiate the rate, figure out the thing. Oh, you don't have this feed, go get this silage. And like, again, useless sort of like metrics of knowing how much soybean to mix with how much corn and real Vista, but knowing how to go drive over, connect the person, figure out where they are, make that discussion and be able to look in their face and talk to them eye to eye, shake their hand.

14:19Like a lot of kids can't do that today. And I think because of that, it's like, man, I'm like, well, let's let them go interface with the world. Right. So that's my view. That lesson could almost be told to people that are well older than 16 these days. If you go back to your comment around AI and just the overwhelming nature of the information that the chatbots give us today, especially when kids are learning, you have a 16-year-old and even younger, and they're learning skills that are not about, I wrote the paper and I got a grade on the paper. It's about the act of learning. What are you coaching parents on or kids on around how and when to use AI?

14:57So you don't atrophy that learning or that like ability to navigate the world. It's a good one. I think, and it's funny because my daughter's school is pretty progressive in the Bay area here. And they're very anti AI. Okay. You can use AI for like, they have, they have like a very, almost like a rubric of when you can use AI and when you can't. And it's pretty good. It's like, Hey, you can use it for research. Cause my thing is I liken it to construction where if you want to build your first house, like, yeah, it's probably good to drive your first hammer and nails and, and, you know, do that with a hammer and a nail before they give you the nail gun.

15:27but more than likely a new journeyman contractor joining a construction site today on their first day would be issued a hammer and some nails but also would be issued a nail gun like they're not going to be like no no for the first year we only want you to do hammer and nail like the old school way like no they're going to like hey you have that but you're going to start using the nail gun pretty quickly and so my view with ai and kids is like i think you're going to be behind it'd be like saying my parents even though like when i was a kid it was like modems and like very early internet and like kind of BBSs and things like that would have said, Oh, no, you're not allowed to use a computer or a calculator.

16:02You need to learn it to do it all by hand. And my parents were quite the opposite. They're like, I don't know how to use these computers. Here's a computer, go figure it out. You should go learn it. Cause that's a cool tool that I think people in the world are going to need. And grateful for my parents for doing that. And my dad in particular pushing us there. And so I think today, like I'm always encouraging my daughter to ask chat, like, what do you think? Like, what would chat say? Like, push yourself to go find those questions. don't ask me, right? Like learn to use the resources that are available.

16:26And again, same reason they would want to use Google maps. Like we had Thomas guides when I was growing up, you had the fricking big old thing, J seven page 52. And like, our kids will never learn that. I don't think they have to, like, they kind of are self-aware of their area and just trust and know that GPS is there. And so I think a lot of that with AI, like if you're not using it, I think you're going to fall behind. But I also agree that like going in every day and dumping in all of your homework into chat gpt and saying just give me the answer is probably also not the right solution so i think it's honestly just educating about those same boundaries like when you shouldn't and shouldn't use these tools just like you know we had to burn our hands when we were kids i'm like oh stove is hot like how do you figure that out there's a much more nuanced sort of stoves hot with today's modern tech but i don't think you can learn that by being told not to use it it's like never use the stove is actually never gonna like you're not gonna learn the lesson.

17:17It's like, no, use the stove. Here's a few guardrails, but you're going to kind of have to figure out what kind of pot you can grab the handle by and what kind of pot you need to go get a mitten for, like looking at it and like, does it have a plastic handle or is that a metal handle that can, you know, some of these things you just got to learn to kind of build your own perception for. And I think the other thing is kids need to also build perception for what's fake in the world, like, you know, deep fakes and deep voices and like the recognizing being human is a skill that's hard. And I think, you know, both older people struggle with this.

17:47I mean, so many people have been faked by the calls, you know, my mom getting a voice faked of me saying, Hey, Kevin needs something, you know, those kinds of like scammer calls, right? Like, so I do think that kids need to experience that because just sheltering them from the tech is actually going to make it worse. And then at some point they're going to like, that sheltering is going to go away. And then they're going to be faced with a pretty raw reality. It reminds me of this, a study that was once done about how school playgrounds have gotten too safe and like helicopter parenting. And it showed that, hey, actually, kids are getting more injured because we've made the world too safe.

18:21And so I've actually did the same experiment with my daughter who wanted to use chat for a school thing. I let her do it. And then she started to represent information that was wrong. It was like a learning moment. Like you have to let kids go through this and fail and be like, you just said something that wasn't true. Now let's go and have a conversation about what's true in the world and the importance of knowing what's true and what's not. Yeah. And being able to like cross check and validate like what you read is actually fiction or nonfiction, right? Like just like a reading a book in the library, you can go to book today and be like, I don't know what section I got it from.

18:53Did I get it from the fiction section or the nonfiction? Like, and you know, how deep are you believing some Stephen King stuff versus like, oh, that's all fiction. Oh wait, that's nonfiction. Okay. You wrote an article once you were talking about your nutrition plan about health and just the health stack in general. I wear an aura ring. I have Function Health. I have a lot of the different services. I'm finding myself piecing together my own healthcare because it's affordable to go direct and the information that you get is really helpful. And now you're working on a startup in healthcare. Healthcare is a highly regulated space.

19:27It's big, it's expensive, it's complicated. What are you seeing in that space and what's encouraging you to go spend your time and energy in healthcare? Yeah, it's a good question. I think two parts. So I think one on the consumer side, the tools are available to sort of like do your own version of concierge medicine today. And like it is relatively inexpensive for most people. What is Kevin's personal concierge medicine stack? If I wanted to go and mimic it, what are you using? So I've had the really expensive, like five figure, you know, tens of thousands of dollars concierge doctors in the past, but I don't use it anymore.

20:02I think what I do now is literally sleep is the first one. So like some version of aura ring, whoop and Apple watch, I wear all three because I'm crazy and I like to correlate the data. And so I'm probably, you know, not normal in that sense, but literally any one of them. And so like, if I had to pick one, I think aura is the simplest and the best. It's the coolest form factor. It's this ring. It just sits on your hand. The downside is when you pick things up or do weights or any kind of gym workout, you kind of got to take it off. And then, so it's like, well, the whoops better for that. And so I kind of wear both for that reason.

20:32Apple watch is just cool. The problem is Apple watch battery only lasts a day or two. So like, you know, you got to charge it more often. So I think that's the like, Hey, tracking my activity and my sleep, those are kind of the two things you get from those. And all of those have some version of sleep. And even the newest Apple watch stuff has great sleep. So it's like sleep and activity, right? Pretty good, right? You want to sleep well, and you want to move, right? Kind of the classic rings. If you think of the Apple watch, their Apple fitness has three things. It's like, Like, did you stand?

20:57Did you move? And like, are you actually actively exercising? I think sleep is the other sort of big one that I would track. So that's like the day-to-day, like, are you sort of doing something? Are you improving? Do you know how much you're sleeping? And then the other one is sort of inside your body, right? The cheap version is like you said, there's function health. There's a lot of things that are like a hundred to 500 bucks a year. You can get enough blood tests to give you a lot of good data that's directionally gonna tell you like, do you have some issues that are worth following up on?

21:23I think the next level up, and function now has a relatively, they bought a company called Ezra. It was, there was a really expensive one in the Bay Area called Pronovo. Ezra was also very expensive. I'm getting my first Ezra MRI in a month. Incredible, yeah. So I've had multiple Pronovos, multiple Ezras and they're really interesting. I think the cost is pretty affordable. It's like down to four or 500 bucks now for the basic one. And I think the only caveat that I've heard people complain about is that like it does cause false positives. And I've heard both providers care about it where like I show up with my report and I'm like, hey, I want you to check these three shadows right in this MRI.

21:57And the guy's like, Oh, you're like one of those Ezra guy. You can just see they're kind of annoyed. Cause they're like, why did you get a referral for cancer in your lungs? And I'm like, dude, I'd rather you check it out and tell me if I have hay fever or if I had cancer like that's. And so then they'd run a second scan and they're like, you're fine. Cause you, you know, you have two scans you can compare. You're like, that was temporary. So I think that's the only downside is that there will cause you some moments of panic, but I'd much prefer a few moments of panic and a little bit of investigative reporting than to not know.