Dalton + Michael Return To YouTube

Michael Seibel 0:00 I felt like for 20 years I had to be so just heads down in tech. I almost had to convince myself that those passions didn't exist.

Dalton Caldwell 0:08 Pretty much every founder I ever worked with at YC would always be like, "Dalton, when are you gonna do your own company again?"

Michael Seibel 0:13 [laughs] Perhaps my biggest regret is if one day I look back and I was like, "Oh, I didn't get to explore all those things."

Dalton Caldwell 0:20 I think I've always lived by the philosophy that if I just push myself really hard and I tried to do really good work with interesting people-

Michael Seibel 0:28 Yes

Dalton Caldwell 0:28 ... interesting things would happen.

Michael Seibel 0:29 [upbeat music]

Michael Seibel 0:33 All right. This is Dalton + Michael, and today we're gonna talk about life changes. Uh, I don't know about you, Dalton, I've had a couple life changes.

Dalton Caldwell 0:43 [laughs]

Michael Seibel 0:44 How about, how about you?

Dalton Caldwell 0:45 Yeah. There's a lot of, lot of new things.

Michael Seibel 0:48 Yeah.

Dalton Caldwell 0:48 Different environment here, changes for the viewers.

Michael Seibel 0:50 Yes, yes. There's a microphone, like, in our face-

Dalton Caldwell 0:52 [laughs]

Michael Seibel 0:52 ... which is awkward. [laughs]

Dalton Caldwell 0:55 There's some differences.

Michael Seibel 0:56 Yes.

Dalton Caldwell 0:56 There's some differences.

Michael Seibel 0:56 Yes. So what are you up to nowadays?

Dalton Caldwell 0:59 Well, um, I'm now a partner emeritus at YC-

Michael Seibel 1:02 Mm-hmm

Dalton Caldwell 1:02 ... and I've started a new VC firm called Standard Capital.

Michael Seibel 1:06 Big change.

Dalton Caldwell 1:06 Yeah, it's a big change.

Michael Seibel 1:07 Big, big change. For me, uh, as well, a partner emeritus, and so still a ton of office hours, which is kind of crazy, but it's been amazing. I've kind of been prodded to try to help make San Francisco better, and it's been an adventure.

Dalton Caldwell 1:25 That sounds really easy, fi- fixing San Francisco, Michael. Like, it's-

Michael Seibel 1:27 Well, as a tech bro-

Dalton Caldwell 1:29 [laughs]

Michael Seibel 1:29 ... let me tell you. [laughs]

Dalton Caldwell 1:31 You all the answers, right? It's just that easy. You're the guy.

Michael Seibel 1:35 It, it, uh, it, it has been humbling to say the least. It's been so much fun getting to meet public servants and just learn something completely new. I think they're all a little surprised in the beginning of the conversation when I don't start with, like, tech bro answers, and, like-

Dalton Caldwell 1:52 [laughs]

Michael Seibel 1:52 ... like, I don't come with my, like, recipe for, like, why aren't... What you're... You suck.

Dalton Caldwell 1:56 Have you thought about using AI?

Michael Seibel 1:57 And, yeah. [laughs] Have you thought about, have you thought about just doing these things? Have you thought, like, oh, like, there's a public safety pro- Have you thought about just deputizing all adult males and drafting them into a police force? Like-

Dalton Caldwell 2:08 Oof.

Michael Seibel 2:08 And so that's been really fun 'cause I think that people get a little disarmed when I'm like, "I don't know anything." Like, I like government. [laughs]

Dalton Caldwell 2:15 [laughs]

Michael Seibel 2:16 I believe in government, but I really don't know anything, and, you know, maybe one to 6% of the things I've learned in software and tech might be relevant.

Dalton Caldwell 2:25 Hmm.

Michael Seibel 2:26 And the rest is kind of new.

Dalton Caldwell 2:27 That's very humble of you. Uh, you're probably blowing their... They're like... Are, do they think you're tricking them?

Michael Seibel 2:32 No. I think what I've learned is tech bros come in pretty hard, pretty fast, pretty hot. So... [laughs]

Dalton Caldwell 2:38 Yeah. Okay.

Michael Seibel 2:39 [laughs] So-

Dalton Caldwell 2:40 All right

Michael Seibel 2:40 ... I think within five minutes they're like, "Well, this is a different conversation." And it's funny 'cause I think a lot of the times I'm asking a version of, can I just see what's happening?

Dalton Caldwell 2:51 Hmm.

Michael Seibel 2:51 Like, can I just look? Can I look over someone's shoulder?

Dalton Caldwell 2:55 Do they have dashboards? [laughs]

Michael Seibel 2:55 No, no. Not, not even dashboards. Like, I just like, can I see someone doing something-

Dalton Caldwell 2:59 Yeah

Michael Seibel 2:59 ... and just start asking myself the question, like, would and/or could I do it differently? And, like, that's been, that's, like, a very different approach, apparently. [laughs] Anyways, to move forward, why did you decide that this was the right time to do something new?

Dalton Caldwell 3:16 Yeah. I mean, look, for me, um, to start with, I did 25 batches, and that's, like, a good round number.

Michael Seibel 3:22 Yes.

Dalton Caldwell 3:23 Um, I also have a newborn, so my daughter was born really recently, like at the end of February.

Michael Seibel 3:29 Yeah.

Dalton Caldwell 3:29 And so, you know, you, we've been through this, man. You go through a lot of life reflection around that.

Michael Seibel 3:32 Yes.

Dalton Caldwell 3:33 Um, also, honestly, man, you, you leaving kind of, uh-

Michael Seibel 3:36 [laughs]

Dalton Caldwell 3:36 ... I can't say that didn't affect my overall psychology.

Michael Seibel 3:39 Sure.

Dalton Caldwell 3:39 It's certainly more top of mind.

Michael Seibel 3:41 Yeah.

Dalton Caldwell 3:41 And, and look, I'm really excited about what I'm doing next. I love the work. I love working with founders, and I love doing office hours, and I, you know-

Michael Seibel 3:50 Yes

Dalton Caldwell 3:50 ... I actually love the craft.

Michael Seibel 3:52 Yes.

Dalton Caldwell 3:52 And I'm kind of excited, uh, to be a founder again myself. It always felt sort of a little weird to be like, "Founders are great," and then I'll run and be like-

Michael Seibel 3:59 [laughs]

Dalton Caldwell 3:59 ... "Well, I'm, I'm, I'm not a found... "

Michael Seibel 4:00 [laughs]

Dalton Caldwell 4:00 "You know, I'm just an employee here."

Michael Seibel 4:02 Yes.

Dalton Caldwell 4:02 And so, look, it's really freeing to just be able to start a new company from scratch. Like, we've talked about it so much on our YouTube channel.

Michael Seibel 4:10 Yes.

Dalton Caldwell 4:11 Uh, literally I signed all the documents-

Michael Seibel 4:13 [laughs]

Dalton Caldwell 4:14 ... and set up payroll and-

Michael Seibel 4:15 Nice. Nice

Dalton Caldwell 4:16 ... you know, I, I did all the stuff that we've been talking about, and I'm really proud of that. Like, it feels good to start something again.

Michael Seibel 4:22 That makes sense. So in terms of helping everyone else out here, I think it'd be interesting to talk about in general how should people make big life decisions?

Dalton Caldwell 4:34 Yeah.

Michael Seibel 4:35 It was funny 'cause I think that there were a couple people that I spoke to about this that kind of put me in the right frame of mind. The first one was my old co-founder, Justin. And, you know, I was talking to him and I was like, "Yeah, it's been 11 years at YC," and this and that, "and, you know, maybe I could just do this job till I retire." And I could kind of just hear the, like, the naked judgment.

Dalton Caldwell 4:59 [laughs]

Michael Seibel 4:59 Like, I could hear-

Dalton Caldwell 5:00 What did it sound like? What does naked judgment sound like?

Michael Seibel 5:02 Like, I don't know. It just-

Dalton Caldwell 5:03 [laughs]

Michael Seibel 5:03 But, like, you know, you know someone for so long, and it w- and he said something that got to me. He was like, "You could literally write everything that will happen between now and retirement if you stay at YC," and like, "Is that the life you want?" Like, "Do you want a life that's that predictable, especially because you're, like, financially secure?"

Dalton Caldwell 5:26 Yeah.

Michael Seibel 5:26 And I was like, "Uh." [laughs]

Dalton Caldwell 5:28 Yeah. I mean, you, you, you do love chaos, Michael. Let's be honest.

Michael Seibel 5:31 I do.

Dalton Caldwell 5:31 Let's be real.

Michael Seibel 5:32 I like chaos. [laughs]

Dalton Caldwell 5:33 You love chaos. You thrive on it.

Michael Seibel 5:35 Yes. Um-

Dalton Caldwell 5:36 So he knew how to push your buttons.

Michael Seibel 5:37 He knew how to push my buttons. Um, the second person, my wife, Sarah. So I was talking to Sarah casually about what post-retirement, um, is like. I weirdly love chaos and planning, which is a-

Dalton Caldwell 5:51 Oh, that's great

Michael Seibel 5:52 ... you know. Anyways, and she said something to me that really got me. She's like, "You've spent your entire adult life in San Francisco." And I was like, "Yes, I moved here at 23."Um, and she said, "You know, you spent 10 years giving back to YC because YC changed the trajectory of your life." And I was like, "Yes." And then she looked at me, she's like, "So are you gonna do anything for San Francisco?" And I was like, "Uh..." [laughs]

Dalton Caldwell 6:19 [laughs] Man, she knows how to push your button.

Michael Seibel 6:20 [laughs]

Dalton Caldwell 6:20 These people in your life, they know-

Michael Seibel 6:22 [laughs]

Dalton Caldwell 6:23 They know where to push you, man.

Michael Seibel 6:24 And it-

Dalton Caldwell 6:24 Yeah

Michael Seibel 6:25 ... it's weird 'cause, like, I've always thought to myself, you know, it's easy when you're in tech. It's like, yeah, I guess I, I live here, but my users are all over the globe, right? [laughs]

Dalton Caldwell 6:35 [laughs]

Michael Seibel 6:35 You know? Like, you can kind of tell yourself like, "Oh, aren't, aren't you post local?" But when you wake up and you're like, this is where you spent your entire adult life, you know, you, you say, "Oh, maybe, maybe there's an obligation there." And the last one was, um, Steve Huffman from Reddit, who kind of casually said, um, at some point in the last year, and it always stuck in my head, "I fully expect most of the capable people we know will end up doing something in public service before they fully retire." And he just said it with such an inevitability. I mean, it's as inevitable as, like, you would have a will.

Dalton Caldwell 7:12 [laughs]

Michael Seibel 7:12 Or like you would have... Like, like, or like you, you know, like how could you, how could you, um, look at yourself with that? [laughs]

Dalton Caldwell 7:19 [laughs] That's no more far-fetched than him being the CEO of a public company, right?

Michael Seibel 7:21 [laughs]

Dalton Caldwell 7:21 You know what I'm saying? In the scheme of-

Michael Seibel 7:23 Yeah

Dalton Caldwell 7:23 ... in the scheme of plausible things.

Michael Seibel 7:24 Yes, exactly.

Dalton Caldwell 7:25 That's definitely plausible.

Michael Seibel 7:27 And so it's funny 'cause, like, those things were rattling in my head. And I think what I've noticed about making big life decisions is that people say stuff to you all the time, but when it sticks, there's something, there's something deeper going on when, like, you can kinda live quote them a couple weeks, a couple months later.

Dalton Caldwell 7:46 Yeah.

Michael Seibel 7:46 How about you? Were there any conversations that kinda helped shape your thinking?

Dalton Caldwell 7:51 Yeah, I mean, I, I have to admit, pretty much every founder I ever worked with at YC would always be like, "Dalton, when are you gonna do your own company again?"

Michael Seibel 7:58 [laughs]

Dalton Caldwell 7:58 Like, I'm sure you got this too.

Michael Seibel 7:59 Yes.

Dalton Caldwell 7:59 This is like in the top five questions I got-

Michael Seibel 8:01 Yes

Dalton Caldwell 8:01 ... as a YC partner.

Michael Seibel 8:02 Yes.

Dalton Caldwell 8:02 They were always like-

Michael Seibel 8:03 Yes

Dalton Caldwell 8:03 ... "Hey, man, just between you and me-

Michael Seibel 8:06 [laughs]

Dalton Caldwell 8:06 ... when are you gonna start your own company again?"

Michael Seibel 8:07 Yes.

Dalton Caldwell 8:07 I'd be like, "No, no, no, this is great." You know, I always had my answer, but-

Michael Seibel 8:11 Yeah

Dalton Caldwell 8:11 ... it was, it's kind of always top of mind when someone's a YC partner-

Michael Seibel 8:15 Yes

Dalton Caldwell 8:15 ... is that we're all founders, and it's kinda hard to corral founders in any one place for an extended period of time.

Michael Seibel 8:21 It is tricky.

Dalton Caldwell 8:22 [laughs]

Michael Seibel 8:22 It helps when they're having kids or are-

Dalton Caldwell 8:24 Yeah

Michael Seibel 8:24 ... otherwise life distracted.

Dalton Caldwell 8:25 Yeah.

Michael Seibel 8:25 [laughs]

Dalton Caldwell 8:26 I think that... So that was certainly something that stuck in my mind, is just the constant questions about that.

Michael Seibel 8:31 Yeah. Yeah.

Dalton Caldwell 8:31 And, you know, I, I've been... I had various answers that were, that were true.

Michael Seibel 8:34 Yeah.

Dalton Caldwell 8:35 Um, and then look, man, talking to my, to my wife and my family just about having complete agency-

Michael Seibel 8:42 Mm-hmm

Dalton Caldwell 8:42 ... over my calendar, agency over what I spend time on, agency over all that stuff is, it's like pretty important.

Michael Seibel 8:49 Yeah.

Dalton Caldwell 8:50 And if you, again, if you think about the advice that we've been giving to people on YouTube all these years, we always just tell people, opt for the high agency route.

Michael Seibel 8:57 Yeah.

Dalton Caldwell 8:57 Opt for doing your own thing.

Michael Seibel 9:00 Yeah.

Dalton Caldwell 9:00 Even if it's hard, you're gonna like yourself more about it-

Michael Seibel 9:03 Yes

Dalton Caldwell 9:03 ... than, than doing the comfortable thing, you know? And so I think, yeah, talking to my wife about a lot of this stuff in terms of, you know, our calendar and our home life, this made a bunch of sense. And look, I'm super excited about how well AI is working for our portfolio companies.

Michael Seibel 9:19 Yes.

Dalton Caldwell 9:19 And so if you think about it, this is my equivalent of starting my own startup using AI.

Michael Seibel 9:24 Sure.

Dalton Caldwell 9:24 So I have founder market fit to be an investor.

Michael Seibel 9:26 Yes.

Dalton Caldwell 9:27 It'd be very hard for me to go start a true pure play, um, AI company.

Michael Seibel 9:31 Well, and you gotta be careful about that founder term, 'cause you know people on Twitter yell at VCs when they-

Dalton Caldwell 9:36 It's true.

Michael Seibel 9:36 [laughs]

Dalton Caldwell 9:36 Well, I think it's when they're, like, not the founders of their VC firm. They just say they're operators.

Michael Seibel 9:41 [laughs]

Dalton Caldwell 9:41 So afforded to it, it's like-

Michael Seibel 9:42 That's true. That is true

Dalton Caldwell 9:43 ... Paul Graham really is the founder of YC.

Michael Seibel 9:44 [laughs] That's true.

Dalton Caldwell 9:45 Does that make sense? Like, he's... Paul Graham is a founder by starting YC.

Michael Seibel 9:48 But I was a founding investor, Dalton. [laughs]

Dalton Caldwell 9:50 Exactly, yeah. I, so I think that's completely fair.

Michael Seibel 9:52 [laughs]

Dalton Caldwell 9:53 But the founders of the VC firms-

Michael Seibel 9:55 Yes. Yes

Dalton Caldwell 9:55 ... I do think they deserve the title.

Michael Seibel 9:56 That's fair.

Dalton Caldwell 9:57 I think, you know-

Michael Seibel 9:57 That's fair

Dalton Caldwell 9:57 ... Ben and Mark from Andreessen-

Michael Seibel 9:58 Yes

Dalton Caldwell 9:58 ... those were the founders of Andreessen.

Michael Seibel 9:59 Well, and there aren't that many. I've been surprised at how few people it seems like start funds to build institutions.

Dalton Caldwell 10:06 Yeah. It, it's hard.

Michael Seibel 10:07 Hard, I agree.

Dalton Caldwell 10:08 [laughs]

Dalton Caldwell 10:09 And so that weighed heavily on me. And look, you know, the, there's, there's this big innovator's dilemma thing where if you're trying to graft AI onto an existing business, it's much harder than starting something for sc- from scratch.

Michael Seibel 10:20 Yep.

Dalton Caldwell 10:20 So just across the YC portfolio in general-

Michael Seibel 10:22 Yep

Dalton Caldwell 10:23 ... we like to fund from scratch disruptors to existing industries that-

Michael Seibel 10:27 Yes

Dalton Caldwell 10:27 ... that are using AI to run their thing, versus trying to buy a company and then put AI on it.

Michael Seibel 10:34 This came up so aggressively in the mobile world, where, like, you and I both know so many people who are working on mobile startups before iPhone. And, like, you would think they were in the best posit-

Dalton Caldwell 10:46 Yeah

Michael Seibel 10:46 ... you know, it's like, oh, they're all squared away. Like, they were in mobile, iPhone happens. None of the YC winners w- had that profile.

Dalton Caldwell 10:54 Yep.

Michael Seibel 10:54 Like, all of the YC winners in mobile started after mobile came out. And so I do think there is something about if a new technology hits, having to start from scratch, otherwise you... Like, are you really gonna embrace and, and, and adopt the new technology?

Dalton Caldwell 11:09 Yeah.

Michael Seibel 11:09 Or is there always gonna be that-

Dalton Caldwell 11:10 What's the... It's the classic innovators dilemma. You have to-

Michael Seibel 11:12 Yeah.

Dalton Caldwell 11:12 Like, again, we see this in our current SaaS portfolio at YC.

Michael Seibel 11:15 Yes. Yes.

Dalton Caldwell 11:16 A lot of people have a ton of revenue in SaaS-

Michael Seibel 11:18 Yes

Dalton Caldwell 11:18 ... and they know they're gonna get disrupted by AI, but that means they have to give up all that revenue.

Michael Seibel 11:22 Yes.

Dalton Caldwell 11:23 You, you've done these operas.

Michael Seibel 11:24 It's hard.

Dalton Caldwell 11:24 I've been doing a lot of these.

Michael Seibel 11:25 It's hard.

Dalton Caldwell 11:25 You know, it's hard to, to cut off the thing that's been working and got you this far-

Michael Seibel 11:29 Yes

Dalton Caldwell 11:30 ... uh, in lieu of doing something new. And so, you know, that weighed heavily, uh, on my mind. And honestly, like, talking to founders-

Michael Seibel 11:37 Mm-hmm

Dalton Caldwell 11:37 ... has been inspiring to me too, 'cause there's like, you know, [laughs] find your own way to do it, but-

Michael Seibel 11:42 Yeah

Dalton Caldwell 11:42 ... keep doing the work, man.

Michael Seibel 11:43 Yeah.

Dalton Caldwell 11:43 Like, keep doing your wacky investing stuff, and [laughs] I, I think it's been super cool, like, all the notes that I got, I know you got them too-

Michael Seibel 11:51 Yeah

Dalton Caldwell 11:51 ... announcing that I was doing this and leaving YC, just the sheer amount of good vibes.

Michael Seibel 11:56 Yeah, that was kinda-

Dalton Caldwell 11:57 Super cool

Michael Seibel 11:57 ... crazy. I think that, like, uh, as an aside, a maybe weirdly unfortunate part of doing YC for so long is that, like, you-Touch so many people's lives, but for you, that's just the day-to-day

Dalton Caldwell 12:14 The job. Yeah

Michael Seibel 12:14 And, uh, seeing all that response that both of us got when we announced we were leaving, I was like, "Oh, crap." Like, it was just this, like, really big reminder like, oh, my God, like, you're a main character-

Dalton Caldwell 12:26 Yeah

Michael Seibel 12:26 ... in thousands of people's lives. [laughs]

Dalton Caldwell 12:29 Yeah, it's pretty cool.

Michael Seibel 12:30 [laughs]

Dalton Caldwell 12:30 Like, it's like the... What, what's the thing, um, the Mark Twain story where he attended his own funeral?

Michael Seibel 12:35 Yeah. Yeah. [laughs]

Dalton Caldwell 12:36 Yes.

Michael Seibel 12:37 Yes.

Dalton Caldwell 12:37 And, like, to hear what people say-

Michael Seibel 12:39 Yes

Dalton Caldwell 12:39 ... uh, is pretty cool, and you would, you would never get that amount of-

Michael Seibel 12:43 No

Dalton Caldwell 12:43 ... of good vibes in any other circumstance except when-

Michael Seibel 12:46 Yeah

Dalton Caldwell 12:46 ... there's a big life change.

Michael Seibel 12:47 Yeah.

Dalton Caldwell 12:48 And so it's one way to kind of take stock of where you're at in life.

Michael Seibel 12:51 It's a feedback loop you only get access to if you take a big leap.

Dalton Caldwell 12:54 Yeah.

Michael Seibel 12:54 No, I totally agree. I think the other thing for me, and I think, you know, different people are built differently. I remember having a lot of passions outside of tech, and I remember when I was trying to make this decision, I felt like for 20 years I had to be so just heads down in tech. I almost had to convince myself that those passions didn't exist, 'cause it's like this is a hard game, and, like, when you're not focused, it's an impossible game. But one of the weird things that kind of... One of the weird techniques that helped me, um, I got kicked out of college, and in order to kind of get the motivation to go back and graduate from Yale, I was like, "I need to make a life plan." I think what I was really responding to was that these institutions in the moment, like Yale, weren't motivating me. Like, I thought I'd be as motivated to graduate from Yale as I was to get into it, and, like, completely not the case. [laughs]

Dalton Caldwell 13:55 [laughs]

Michael Seibel 13:56 And so it's kind of like, all right, I gotta put some other things out there where, like, graduating's gonna be prerequisite, but, like, this thing isn't the actual end game. And so for me, it was a simple plan. It was 20s money, 30s family, 40s government-

Dalton Caldwell 14:11 Hmm

Michael Seibel 14:11 ... retire and teach. That was a plan that I made when I was 21 years old.

Dalton Caldwell 14:15 When you were 21?

Michael Seibel 14:16 When I was 21 years old, Dalton.

Dalton Caldwell 14:17 Wow.

Michael Seibel 14:18 And it was funny. I, I said this to somebody, and they were like, "You're crazy." Like, they were like, "It is crazy that you would consider planning your whole life." And I feel like people who know me really well, they're like, "That's pretty on brand." [laughs]

Dalton Caldwell 14:33 Yeah.

Michael Seibel 14:33 But for this person I was talking to- [laughs]

Dalton Caldwell 14:35 I mean, Michael, it's a little crazy to plan your whole life.

Michael Seibel 14:37 [laughs]

Dalton Caldwell 14:37 I'm not, I'm not with you on this one, man. I'm not... I'm not with you.

Michael Seibel 14:41 Um, not for everyone, right? [laughs]

Dalton Caldwell 14:43 Yeah.

Michael Seibel 14:43 Not for... Your mileage may vary, but it's been 20 years, and things have awkwardly followed that plan. And so, um, you know, I just turned, uh, 42, and I was kind of, I think subconsciously in the back of my head I was kind of like, "The plan."

Dalton Caldwell 15:04 Yeah.

Michael Seibel 15:05 Like, what about the plan? The plan's been working. What about the plan? And I would've been more than happy to change the plan if I felt like it needed to be changed, right? Like-

Dalton Caldwell 15:15 Yeah

Michael Seibel 15:15 ... yeah, like, who cares, right? It's not like I, every thing was really perfectly laid out. And by the way, that's not that detailed of a plan, right? I mean, it's [laughs] one word per decade. But, like, having that reminded me about the other things that I really liked. You know, rolling back into what Justin said, like, I now have the opportunity or the privilege to be able to explore these other things that I like.

Dalton Caldwell 15:39 Yeah.

Michael Seibel 15:39 And perhaps my biggest regret is if one day I look back and I was like, oh, I didn't get to explore all those things. And so for me, like, that really kind of cinched it, 'cause it was like, oh, okay, like, this is just the next phase of the plan, right? This is just the ne- And what's really funny is going into each of those phases, I had no i- You know, you start a company with your co-founder who wears a camera on his head broadcasting 24/7. You're not, you're not-

Dalton Caldwell 16:05 Sounds like a billion-dollar company to me. [laughs]

Michael Seibel 16:06 Right, right. [laughs] You're not drawing a straight line to money, right? [laughs] You know? And, like, you know, family it was kind of, you know, I was 30, I was dating my wife, but, like, we weren't married, we didn't have kids, right? Like da, da, da, da. Um, and so for me it was kind of like this plan never works where you take a leap and it's, like, a safe leap.

Dalton Caldwell 16:25 Yeah.

Michael Seibel 16:25 This plan always works where it's kind of like you gotta take a leap, and then you gotta feel your way down. And so that's what's been so fun over the past three to four months is, like, taking that leap and then realizing, like, oh, shit, I really do like this other stuff.

Dalton Caldwell 16:38 Yeah.

Michael Seibel 16:38 I still love tech, but l- does it have to be 97%? [laughs]

Dalton Caldwell 16:44 [laughs]

Michael Seibel 16:44 Like, it doesn't-

Dalton Caldwell 16:45 Maybe. I don't know.

Michael Seibel 16:46 You know, there are enough people who can carry the ball on the tech side.

Dalton Caldwell 16:49 Yeah.

Michael Seibel 16:49 Um, and so that's been, that's been incredible.

Dalton Caldwell 16:53 I think I've always lived by the philosophy that if I just push myself really hard and I tried to do really good work with interesting people-

Michael Seibel 17:01 Yes

Dalton Caldwell 17:01 ... interesting things would happen.

Michael Seibel 17:03 Okay.

Dalton Caldwell 17:03 And that's kind of how I got-

Michael Seibel 17:04 Okay

Dalton Caldwell 17:04 ... from just some guy in Texas-

Michael Seibel 17:07 Okay

Dalton Caldwell 17:07 ... onto, like, this crazy life trajectory I've been on.

Michael Seibel 17:10 That sounds a good life plan.

Dalton Caldwell 17:11 I get... But do you see what I'm saying?

Michael Seibel 17:13 Yeah.

Dalton Caldwell 17:13 I was like-

Michael Seibel 17:14 Or life philosophy

Dalton Caldwell 17:14 ... let me just do... Yeah. It's totally life philosophy.

Michael Seibel 17:16 Yes. Yes.

Dalton Caldwell 17:16 Which is I should always be almost, like, uncomfortable. Like, I should always be-

Michael Seibel 17:20 Mm

Dalton Caldwell 17:20 ... right at the limits of my skill set.

Michael Seibel 17:22 Mm-hmm.

Dalton Caldwell 17:22 I should always be pushing myself right to where I'm, like, redlining.

Michael Seibel 17:25 Yes.

Dalton Caldwell 17:26 And again, we've, we've done some crazy stuff together. You understand what I'm talking about.

Michael Seibel 17:28 Yes.

Dalton Caldwell 17:29 Like reinventing YC to run on Zoom.

Michael Seibel 17:32 Yes. [laughs] COVID was fun.

Dalton Caldwell 17:34 It was, it was right at the limits of our, of our skill set.

Michael Seibel 17:37 Yes.

Dalton Caldwell 17:37 Um-

Michael Seibel 17:37 Yes. While having children.

Dalton Caldwell 17:39 You know. [laughs]

Michael Seibel 17:39 While having children.

Dalton Caldwell 17:41 Um, you know, I just... I've always been my own worst critic, and I've always been hard to myself, on myself.

Michael Seibel 17:45 Mm.

Dalton Caldwell 17:46 And I just wanted to feel like I was pushing myself to the very limit, and if I just kept doing this, that would compound over enough time-

Michael Seibel 17:52 Yes

Dalton Caldwell 17:53 ... to just have a really interesting life.

Michael Seibel 17:55 Okay.

Dalton Caldwell 17:55 And yeah, I've been kind of subscribing to that theory, and continue to do so.

Michael Seibel 18:00 I think for you, maybe a question that I would ask is what was something kind of counterintuitive that people don't know that foundersDon't know about setting up a fund. Something weird, something different. Not like about like the strategy fund, but just more just kind of like inside baseball.

Dalton Caldwell 18:18 At the end of the day, a lot of the people at big companies or successful franchises-

Michael Seibel 18:22 Mm-hmm

Dalton Caldwell 18:23 ... they know in their heart, if they're self-aware-

Michael Seibel 18:26 Mm

Dalton Caldwell 18:26 ... that people are nice to them and respect them because they work somewhere that is important and powerful. And, you know, there's two ways you can deal with that. Either one, you believe that you're special-

Michael Seibel 18:37 Mm

Dalton Caldwell 18:37 ... and so you're like, "Oh, I'm a PM at Facebook. I'm a really big dog. I'm so important. Like, I-"

Michael Seibel 18:42 We love Facebook PMs.

Dalton Caldwell 18:44 [laughs]

Michael Seibel 18:44 They're some of the best people on Earth. [laughs]

Dalton Caldwell 18:46 They're great. No, but, like, you basically-

Michael Seibel 18:48 I'm really good friends with a Facebook PM.

Dalton Caldwell 18:49 I'm sure you are.

Michael Seibel 18:50 [laughs]

Dalton Caldwell 18:50 You basically confuse the power of the place you work with yourself.

Michael Seibel 18:54 Mm-hmm.

Dalton Caldwell 18:55 And so you, you get-

Michael Seibel 18:56 Yes

Dalton Caldwell 18:56 ... you dis- you get entangled-

Michael Seibel 18:58 Yes

Dalton Caldwell 18:59 ... where your identity and your work identity are the same thing.

Michael Seibel 19:02 Yeah.

Dalton Caldwell 19:02 And you just get really, I don't know, like you get confused about what's what.

Michael Seibel 19:06 Yes.

Dalton Caldwell 19:06 The non-self-aware people are just unaware of this, and they're, you know, they leave a, they leave an important job, and they're just like shocked. [laughs]

Michael Seibel 19:15 [laughs]

Dalton Caldwell 19:16 Um, and then I think the self-aware people are aware of this.

Michael Seibel 19:19 Yeah.

Dalton Caldwell 19:19 And this is why they stay in those jobs forever, is 'cause they're like, "Hey, if I leave, no one's gonna be nice to me anymore. I'm gonna lose all the juice that I had." And so I think this is what keeps people... They, they won't admit this in public, but I think-

Michael Seibel 19:29 Yeah, yeah, yeah

Dalton Caldwell 19:29 ... a lot of people are kept in various jobs-

Michael Seibel 19:32 Yeah

Dalton Caldwell 19:32 ... with the self, correct self-awareness that the moment they leave, no one will return their calls anymore. People may be like, "Wow, these guys have it all figured out."

Michael Seibel 19:40 Yeah.

Dalton Caldwell 19:40 Like, "These guys have it all locked in."

Michael Seibel 19:42 Yes.

Dalton Caldwell 19:42 "Every day must be stress free." No, this, this is hard.

Michael Seibel 19:45 Yeah.

Dalton Caldwell 19:45 Um, just like I'm imagining trying to fix city government's hard. This is the hardest thing I've ever done, man.

Michael Seibel 19:50 Yeah.

Dalton Caldwell 19:50 Like, I've done a lot of hard stuff, but to, to start something from scratch at this, especially at the scale-

Michael Seibel 19:55 Yeah

Dalton Caldwell 19:55 ... of what we're trying to do.

Michael Seibel 19:56 Yeah.

Dalton Caldwell 19:57 This is objectively the hardest thing I've ever done.

Michael Seibel 20:00 If you're in that mindset, and I agree with you, that like if you only know how good you are when you're kind of in that hard charging, in that most stressful moment, it's almost like another reason to consider making a big life change, 'cause it's like you only really know your top speed or your top capability in those moments.

Dalton Caldwell 20:16 Right.

Michael Seibel 20:16 And like ditto when people don't kinda have to say yes to you, right?

Dalton Caldwell 20:23 [laughs]

Michael Seibel 20:23 You're kinda getting a real grade.

Dalton Caldwell 20:24 Yeah.

Michael Seibel 20:24 Not like, uh, not like, uh-

Dalton Caldwell 20:26 You're a civilian again.

Michael Seibel 20:27 You know.

Dalton Caldwell 20:27 It's, it's like people in the government, all these people retire from government jobs and-

Michael Seibel 20:30 Yeah

Dalton Caldwell 20:31 ... you know, imagine they treat you differently-

Michael Seibel 20:33 Yeah

Dalton Caldwell 20:33 ... once you retire from a government job.

Michael Seibel 20:35 Yeah. I would say for myself, so one, I don't wanna take on the mantle of fixing government. That is, that's at least more than a three-month task. Um, I think the only thing I'm excited about is trying to help, but I think that what I can do, it might be interesting, is just kinda go over a little bit of what I've learned.

Dalton Caldwell 20:51 Yeah.

Michael Seibel 20:51 And this is kind of like a TLDR after, I don't know, 90 to 120 hours of conversations with people in city government, conversations with citizens, and thinking. So I would say the first inning of knowledge. [laughs] First one, I think, I think what is most obvious to me and what scares me might not be obvious to other people, is like most people who work in government are trying to do the right thing. Most people who are working in government are capable people who are actively choosing to take a lower salary to give back. So that's like a big deal. So the second thing that I've learned that's been very surprising me is like I expected more smoky rooms. Like, I expected more like the people want this, but we're gonna like be, do this other thing. [laughs]

Dalton Caldwell 21:37 That's what people think about tech, too.

Michael Seibel 21:39 Yeah, yeah. [laughs]

Dalton Caldwell 21:39 Where they th- they actually think that there's a lot more coordination.

Michael Seibel 21:42 Yeah.

Dalton Caldwell 21:42 There's not as much coordination as people think.

Michael Seibel 21:44 There are many problems where when I kinda got to the root of them, it was our politicians and doing, and our government doing the things that we said we wanted, and then it turns out we didn't know-

Dalton Caldwell 22:01 It was a bad idea

Michael Seibel 22:01 ... the right thing. [laughs]

Dalton Caldwell 22:03 [laughs]

Michael Seibel 22:03 Like, like it so reminds me of like listening to your users and your users being like-

Dalton Caldwell 22:08 They want something bad.

Michael Seibel 22:09 Yeah, like I want all the text on the website to be black and the background to be black. [laughs]

Dalton Caldwell 22:14 Yeah.

Michael Seibel 22:15 And, and it's hard. You can't run AB tests in the same way. Like, it's, this is a hard environment, but like I was shocked how often it was like, "Yeah, we did what, what the voters told us to do." And it was like, oh, shit. Okay. Um, I think the other thing I didn't realize is like in the same tone, we as citizens drive the bureaucracy. Like, I think this story is not told the right way. Like, it's always told like we're victims of government bureaucracy. It's like we are actually driving the government to create rules to make the government less efficient.

Dalton Caldwell 22:49 Hmm.

Michael Seibel 22:50 Like, every time there's like one bad apple-

Dalton Caldwell 22:53 Yeah, okay

Michael Seibel 22:53 ... we are like-

Dalton Caldwell 22:54 Yes

Michael Seibel 22:54 ... "Put in all the new rules. Like, wh- how could this happen?" And then like there's 50 new rules, and if a company were run this way, it would never work. [laughs]

Dalton Caldwell 23:04 Well, big companies are run this way, where when something bad happens-

Michael Seibel 23:07 Put a lot of rules in

Dalton Caldwell 23:08 ... the scar tissue is to create rules to prevent that bad thing from ever happening again.

Michael Seibel 23:10 But big companies can't do it as well as government.

Dalton Caldwell 23:13 Yeah.

Michael Seibel 23:13 Government can create rules that you can go to jail if you break. [laughs]

Dalton Caldwell 23:16 No, that's what's crazy, is they, they're enforced by the police.

Michael Seibel 23:19 Yes.

Dalton Caldwell 23:19 So that's f-

Michael Seibel 23:20 That's a different kind of rule

Dalton Caldwell 23:20 ... I think that's a fair point.

Michael Seibel 23:21 Yes.

Dalton Caldwell 23:21 All right, fair point. Fair point.

Michael Seibel 23:23 But it's like, but once again, it's triggered by us.

Dalton Caldwell 23:26 Yeah.

Michael Seibel 23:26 It's triggered by like somebody made a mistake, honest or not, and us being like, "How, how could you let that happen?" Like, how could the government not play error-free ball, like for 100 years with all-

Dalton Caldwell 23:38 Yeah.

Michael Seibel 23:38 Well, and so that's like a, a big one where I'm just like, if you think you're a victim of bureaucracy, like a city worker is the largest victim-

Dalton Caldwell 23:46 Yeah

Michael Seibel 23:46 ... of the bureaucracy. I think the other one that kind of, and this applies outside of government, but this really got me. We were talking about this earlier. Like, I took for granted that software companies build their own tools. That's just like a muscle that they have that we've always had, and I think that what I'm realizing is how many organizations don't have that muscle. It's basically if we're using software, it means some vendor's building it for us. It's sad, 'cause think about how many tiny tools that we built at YC-

Dalton Caldwell 24:13 Yeah

Michael Seibel 24:14 ... were like, God forbid... I mean, most people know about Bookface now, right? God forbid we had to find a vendor who would sell usLike YC alumni s-

Dalton Caldwell 24:22 Or, or like a vendor for the application flow.

Michael Seibel 24:24 Oh, God.

Dalton Caldwell 24:25 Yeah. [laughs]

Michael Seibel 24:26 Imagine. Like we would've-

Dalton Caldwell 24:27 We wanted to change some text on the application, we'd have to-

Michael Seibel 24:29 Call someone?

Dalton Caldwell 24:30 Call someone.

Michael Seibel 24:30 Call our account manager?

Dalton Caldwell 24:32 Yeah.

Michael Seibel 24:32 It never would've worked, and I think I just took for granted how many times we were making our own tools, and now I'm like looking at organization that like, it's very, very, very hard for them to make their own tools, and it's like, oh, that's bad. And, and I understand why, right? And it... But, but it's, it's, it's like, it's harder. Um, I think the other one that keeps on coming up, you think that government has these powers and these responsibilities, and you kinda don't wanna make it a human operation. You wanna make it a machine. It's like, well, the permitting process is bad. This supervisor can write legislation to improve it. These people need to vote for it, and then it's done. And when you start talking to people, it's like, obviously it's a h- everything is humans.

Dalton Caldwell 25:19 Mm.

Michael Seibel 25:20 Everything is humans. And so it's really nice to kind of be the, the Twitter tech bro and like try to like solve all the city's problems in like a tweet, you know? [laughs] And but just like the more I've learned, the more it's just like, you know, I had this thought the other day. I was like, you know, it's easier trying to advise a founder to build a successful company. Like, that's easier, you know? With the amount of research I've done, it's not like I'm sc- There are no conclusions. There's no like [laughs]

Dalton Caldwell 25:46 Oh, that's great. I thought you were gonna-

Michael Seibel 25:47 No.

Dalton Caldwell 25:47 I was waiting for the conclusion, Michael.

Michael Seibel 25:48 No, there's no conclusion. [laughs]

Dalton Caldwell 25:50 Now, I thought you were gonna fix everything.

Michael Seibel 25:50 There's no solution. Like, like, like this is hard. [laughs]

Dalton Caldwell 25:56 [laughs]

Michael Seibel 25:56 And by the way, like that's different for me. Usually, with this amount of engagement in anyone's company, I would be able to offer like advice. I am nowhere close to like- [laughs]

Dalton Caldwell 26:08 So iPads isn't the solution. I'm just kidding.

Michael Seibel 26:10 You're just kidding. [laughs]

Dalton Caldwell 26:10 Yeah, just like all, everyone needs i... No.

Michael Seibel 26:13 Um, to bring it back, like I respect people in public service even more. It's like they're taking on the hardest problems.

Dalton Caldwell 26:19 Yeah.

Michael Seibel 26:20 They're not getting paid crazy amounts of money. We are making their lives harder as citizens, and then we shit on them, and then like they're subject to the wind just like every other business, but we pretend like we're in this hermetically sealed environment the government controls. I used to think startups was one of the most stressful, hardest jobs-

Dalton Caldwell 26:40 Yeah

Michael Seibel 26:40 ... imaginable, and I'm like-

Dalton Caldwell 26:42 Yeah, it sounds rough.

Michael Seibel 26:43 This is- [laughs] It's like, yes. Like I almost sometimes in my conversations, I feel like I'm just like I have to express compassion. I'm like, "This is-"

Dalton Caldwell 26:52 Yeah.

Michael Seibel 26:53 "I respect you for doing this." So anyways, I think that's what's been kind of humbling and fun, and, and like this is where I live. So it's like if I wanna contribute to where I live, you gotta learn this stuff. Most people can have a men- a renter mentality, but some people have to have a bit more of an owner mentality at some point, and I feel like maybe I've been renting-

Dalton Caldwell 27:18 Yeah

Michael Seibel 27:18 ... too long, you know? So.

Dalton Caldwell 27:20 That's very, that's very noble of you. I think a lot of people are just renters for life, man. [laughs]

Michael Seibel 27:27 [laughs] Renters for... I'm gonna make some T-shirts. [laughs]

Dalton Caldwell 27:31 [laughs]

Michael Seibel 27:32 Anyways, final advice for people listening to this video contemplating a big life decision. Maybe it's starting a company, maybe it's starting a family, maybe it's moving to the Bay Area. Um, what do you think?

Dalton Caldwell 27:46 You know, here's the trick that I do that I would actually recommend. I think people are used to now writing prompts for LLMs-

Michael Seibel 27:53 Mm

Dalton Caldwell 27:54 ... and that you realize after you've written prompts for a while, that the better the prompt, the more likely you get a good answer. You still with me, right? Like you have to spend time-

Michael Seibel 28:02 Very much so, yes. [laughs]

Dalton Caldwell 28:03 And I think there's a superpower we can all develop-

Michael Seibel 28:08 Okay

Dalton Caldwell 28:08 ... of crafting the prompts for ourselves-

Michael Seibel 28:11 Mm

Dalton Caldwell 28:11 ... and thinking about it that way when we're making decisions.

Michael Seibel 28:13 Yes.

Dalton Caldwell 28:14 Which is like, you know, given these constraints or given this and given that, and kind of like try to formulate your thoughts into a very cohesive, linear way.

Michael Seibel 28:22 Yeah.

Dalton Caldwell 28:23 And then I think you tend to get pretty good answers, and the prompt that I keep giving myself is, "If I were doing office hours with myself-

Michael Seibel 28:29 Mm

Dalton Caldwell 28:29 ... what would I say?" 'Cause when I do that-

Michael Seibel 28:32 Mm

Dalton Caldwell 28:32 ... somehow a whole different part of my brain is activated because we're s- you know, we're so used to giving advice about things. I'm always like, "Well, what advice would I give myself?" And I've had a lot of... You know, I'm not sure that would work for everybody, but-

Michael Seibel 28:44 Mm-hmm

Dalton Caldwell 28:44 ... I've had a lot of luck with that type of prompt, and in general, I think thinking of your own thoughts as prompts and trying to curate them-

Michael Seibel 28:51 Mm-hmm

Dalton Caldwell 28:51 ... is a pretty good hack, man.

Michael Seibel 28:54 I like that. I think if I try to extract out the prompt perhaps I'm, I, I'm subconsciously giving myself, it would probably be some version of, "You've been incredibly lucky. When all's said and done, what's the story that can be told about like how you gave back, like in thanks for being that lucky?" I don't think you can deserve to be lucky, but I think that like if you are lucky, you can kind of give the world thanks. And so like what, how do you maximize that, I think is the, is, is interesting, and I think YC gave me a great opportunity to do that. But I think, um, maybe government is one of the single places that gives you more of an opportunity to do that. All right. Well, great chat. Welcome back.

Dalton Caldwell 29:46 [laughs]

Michael Seibel 29:47 There are gonna be more of these. Have a great day.

Dalton Caldwell 29:50 Thanks. Appreciate it, Michael. [outro music]