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Dalton + MichaelDalton + Michael

Dalton + Michael Return To YouTube

Dalton Caldwell and Michael Seibel return to YouTube! In this episode the duo discusses big life changes and what led them to leave their jobs as Managing Partners at Y Combinator. Dalton + Michael is brought to you by Dalton's new VC firm, @Standard_Cap http://standardcap.com

Michael SeibelhostDalton Caldwellhost
Sep 2, 202530mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 0:33

    Intro

    1. MS

      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.

    2. DC

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

    3. MS

      [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."

    4. DC

      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-

    5. MS

      Yes

    6. DC

      ... interesting things would happen.

    7. MS

      [upbeat music]

  2. 0:33 – 0:59

    Reuniting on YouTube: life changes and a new format

    1. MS

      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.

    2. DC

      [laughs]

    3. MS

      How about, how about you?

    4. DC

      Yeah. There's a lot of, lot of new things.

    5. MS

      Yeah.

    6. DC

      Different environment here, changes for the viewers.

    7. MS

      Yes, yes. There's a microphone, like, in our face-

    8. DC

      [laughs]

    9. MS

      ... which is awkward. [laughs]

    10. DC

      There's some differences.

    11. MS

      Yes.

    12. DC

      There's some differences.

    13. MS

      Yes. So what are you up to nowadays?

  3. 0:59 – 1:07

    Dalton’s next chapter: leaving YC leadership to start Standard Capital

    1. DC

      Well, um, I'm now a partner emeritus at YC-

    2. MS

      Mm-hmm

    3. DC

      ... and I've started a new VC firm called Standard Capital.

    4. MS

      Big change.

    5. DC

      Yeah, it's a big change.

  4. 1:07 – 3:16

    Michael’s pivot: partner emeritus and learning how city government works

    1. MS

      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.

    2. DC

      That sounds really easy, fi- fixing San Francisco, Michael. Like, it's-

    3. MS

      Well, as a tech bro-

    4. DC

      [laughs]

    5. MS

      ... let me tell you. [laughs]

    6. DC

      You all the answers, right? It's just that easy. You're the guy.

    7. MS

      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-

    8. DC

      [laughs]

    9. MS

      ... like, I don't come with my, like, recipe for, like, why aren't... What you're... You suck.

    10. DC

      Have you thought about using AI?

    11. MS

      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-

    12. DC

      Oof.

    13. MS

      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]

    14. DC

      [laughs]

    15. MS

      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.

    16. DC

      Hmm.

    17. MS

      And the rest is kind of new.

    18. DC

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

    19. MS

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

    20. DC

      Yeah. Okay.

    21. MS

      [laughs] So-

    22. DC

      All right

    23. MS

      ... 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?

    24. DC

      Hmm.

    25. MS

      Like, can I just look? Can I look over someone's shoulder?

    26. DC

      Do they have dashboards? [laughs]

    27. MS

      No, no. Not, not even dashboards. Like, I just like, can I see someone doing something-

    28. DC

      Yeah

    29. MS

      ... 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?

  5. 3:16 – 4:22

    Why now? milestones, family reflection, and the ripple effect of departures

    1. DC

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

    2. MS

      Yes.

    3. DC

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

    4. MS

      Yeah.

    5. DC

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

    6. MS

      Yes.

    7. DC

      Um, also, honestly, man, you, you leaving kind of, uh-

    8. MS

      [laughs]

    9. DC

      ... I can't say that didn't affect my overall psychology.

    10. MS

      Sure.

    11. DC

      It's certainly more top of mind.

    12. MS

      Yeah.

    13. DC

      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-

    14. MS

      Yes

    15. DC

      ... I actually love the craft.

    16. MS

      Yes.

    17. DC

      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-

    18. MS

      [laughs]

    19. DC

      ... "Well, I'm, I'm, I'm not a found... "

    20. MS

      [laughs]

    21. DC

      "You know, I'm just an employee here."

    22. MS

      Yes.

    23. DC

      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.

    24. MS

      Yes.

    25. DC

      Uh, literally I signed all the documents-

    26. MS

      [laughs]

    27. DC

      ... and set up payroll and-

    28. MS

      Nice. Nice

    29. DC

      ... 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.

  6. 4:22 – 7:51

    How big decisions crystallize: the conversations that stick

    1. MS

      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?

    2. DC

      Yeah.

    3. MS

      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.

    4. DC

      [laughs]

    5. MS

      Like, I could hear-

    6. DC

      What did it sound like? What does naked judgment sound like?

    7. MS

      Like, I don't know. It just-

    8. DC

      [laughs]

    9. MS

      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?"

    10. DC

      Yeah.

    11. MS

      And I was like, "Uh." [laughs]

    12. DC

      Yeah. I mean, you, you, you do love chaos, Michael. Let's be honest.

    13. MS

      I do.

    14. DC

      Let's be real.

    15. MS

      I like chaos. [laughs]

    16. DC

      You love chaos. You thrive on it.

    17. MS

      Yes. Um-

    18. DC

      So he knew how to push your buttons.

    19. MS

      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-

    20. DC

      Oh, that's great

    21. MS

      ... 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]

    22. DC

      [laughs] Man, she knows how to push your button.

    23. MS

      [laughs]

    24. DC

      These people in your life, they know-

    25. MS

      [laughs]

    26. DC

      They know where to push you, man.

    27. MS

      And it-

    28. DC

      Yeah

    29. MS

      ... 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]

    30. DC

      [laughs]

  7. 7:51 – 10:09

    Dalton’s decision drivers: founder pull, agency, and AI-era timing

    1. DC

      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?"

    2. MS

      [laughs]

    3. DC

      Like, I'm sure you got this too.

    4. MS

      Yes.

    5. DC

      This is like in the top five questions I got-

    6. MS

      Yes

    7. DC

      ... as a YC partner.

    8. MS

      Yes.

    9. DC

      They were always like-

    10. MS

      Yes

    11. DC

      ... "Hey, man, just between you and me-

    12. MS

      [laughs]

    13. DC

      ... when are you gonna start your own company again?"

    14. MS

      Yes.

    15. DC

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

    16. MS

      Yeah

    17. DC

      ... it was, it's kind of always top of mind when someone's a YC partner-

    18. MS

      Yes

    19. DC

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

    20. MS

      It is tricky.

    21. DC

      [laughs]

    22. MS

      It helps when they're having kids or are-

    23. DC

      Yeah

    24. MS

      ... otherwise life distracted.

    25. DC

      Yeah.

    26. MS

      [laughs]

    27. DC

      I think that... So that was certainly something that stuck in my mind, is just the constant questions about that.

    28. MS

      Yeah. Yeah.

    29. DC

      And, you know, I, I've been... I had various answers that were, that were true.

    30. MS

      Yeah.

  8. 10:09 – 11:43

    The Innovator’s Dilemma in practice: why incumbents struggle with AI (and mobile déjà vu)

    1. DC

      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.

    2. MS

      Yep.

    3. DC

      So just across the YC portfolio in general-

    4. MS

      Yep

    5. DC

      ... we like to fund from scratch disruptors to existing industries that-

    6. MS

      Yes

    7. DC

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

    8. MS

      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-

    9. DC

      Yeah

    10. MS

      ... 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.

    11. DC

      Yep.

    12. MS

      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?

    13. DC

      Yeah.

    14. MS

      Or is there always gonna be that-

    15. DC

      What's the... It's the classic innovators dilemma. You have to-

    16. MS

      Yeah.

    17. DC

      Like, again, we see this in our current SaaS portfolio at YC.

    18. MS

      Yes. Yes.

    19. DC

      A lot of people have a ton of revenue in SaaS-

    20. MS

      Yes

    21. DC

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

    22. MS

      Yes.

    23. DC

      You, you've done these operas.

    24. MS

      It's hard.

    25. DC

      I've been doing a lot of these.

    26. MS

      It's hard.

    27. DC

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

    28. MS

      Yes

    29. DC

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

    30. MS

      Mm-hmm

  9. 11:43 – 12:54

    The emotional feedback of a big leap: realizing your impact at YC

    1. DC

      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-

    2. MS

      Yeah

    3. DC

      ... announcing that I was doing this and leaving YC, just the sheer amount of good vibes.

    4. MS

      Yeah, that was kinda-

    5. DC

      Super cool

    6. MS

      ... 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

    7. DC

      The job. Yeah

    8. MS

      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-

    9. DC

      Yeah

    10. MS

      ... in thousands of people's lives. [laughs]

    11. DC

      Yeah, it's pretty cool.

    12. MS

      [laughs]

    13. DC

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

    14. MS

      Yeah. Yeah. [laughs]

    15. DC

      Yes.

    16. MS

      Yes.

    17. DC

      And, like, to hear what people say-

    18. MS

      Yes

    19. DC

      ... uh, is pretty cool, and you would, you would never get that amount of-

    20. MS

      No

    21. DC

      ... of good vibes in any other circumstance except when-

    22. MS

      Yeah

    23. DC

      ... there's a big life change.

    24. MS

      Yeah.

    25. DC

      And so it's one way to kind of take stock of where you're at in life.

    26. MS

      It's a feedback loop you only get access to if you take a big leap.

    27. DC

      Yeah.

  10. 12:54 – 16:53

    Michael’s long arc: rediscovering passions and a decades-based life plan

    1. MS

      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]

    2. DC

      [laughs]

    3. MS

      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-

    4. DC

      Hmm

    5. MS

      ... retire and teach. That was a plan that I made when I was 21 years old.

    6. DC

      When you were 21?

    7. MS

      When I was 21 years old, Dalton.

    8. DC

      Wow.

    9. MS

      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]

    10. DC

      Yeah.

    11. MS

      But for this person I was talking to- [laughs]

    12. DC

      I mean, Michael, it's a little crazy to plan your whole life.

    13. MS

      [laughs]

    14. DC

      I'm not, I'm not with you on this one, man. I'm not... I'm not with you.

    15. MS

      Um, not for everyone, right? [laughs]

    16. DC

      Yeah.

    17. MS

      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."

    18. DC

      Yeah.

    19. MS

      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-

    20. DC

      Yeah

    21. MS

      ... 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.

    22. DC

      Yeah.

    23. MS

      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-

    24. DC

      Sounds like a billion-dollar company to me. [laughs]

    25. MS

      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.

    26. DC

      Yeah.

    27. MS

      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.

    28. DC

      Yeah.

    29. MS

      I still love tech, but l- does it have to be 97%? [laughs]

    30. DC

      [laughs]

  11. 16:53 – 18:00

    Dalton’s philosophy: redlining your skills with great people compounds over time

    1. DC

      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-

    2. MS

      Yes

    3. DC

      ... interesting things would happen.

    4. MS

      Okay.

    5. DC

      And that's kind of how I got-

    6. MS

      Okay

    7. DC

      ... from just some guy in Texas-

    8. MS

      Okay

    9. DC

      ... onto, like, this crazy life trajectory I've been on.

    10. MS

      That sounds a good life plan.

    11. DC

      I get... But do you see what I'm saying?

    12. MS

      Yeah.

    13. DC

      I was like-

    14. MS

      Or life philosophy

    15. DC

      ... let me just do... Yeah. It's totally life philosophy.

    16. MS

      Yes. Yes.

    17. DC

      Which is I should always be almost, like, uncomfortable. Like, I should always be-

    18. MS

      Mm

    19. DC

      ... right at the limits of my skill set.

    20. MS

      Mm-hmm.

    21. DC

      I should always be pushing myself right to where I'm, like, redlining.

    22. MS

      Yes.

    23. DC

      And again, we've, we've done some crazy stuff together. You understand what I'm talking about.

    24. MS

      Yes.

    25. DC

      Like reinventing YC to run on Zoom.

    26. MS

      Yes. [laughs] COVID was fun.

    27. DC

      It was, it was right at the limits of our, of our skill set.

    28. MS

      Yes.

    29. DC

      Um-

    30. MS

      Yes. While having children.

  12. 18:00 – 20:35

    Inside baseball on starting a fund: status, identity, and becoming a “civilian” again

    1. MS

      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.

    2. DC

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

    3. MS

      Mm-hmm

    4. DC

      ... they know in their heart, if they're self-aware-

    5. MS

      Mm

    6. DC

      ... 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-

    7. MS

      Mm

    8. DC

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

    9. MS

      We love Facebook PMs.

    10. DC

      [laughs]

    11. MS

      They're some of the best people on Earth. [laughs]

    12. DC

      They're great. No, but, like, you basically-

    13. MS

      I'm really good friends with a Facebook PM.

    14. DC

      I'm sure you are.

    15. MS

      [laughs]

    16. DC

      You basically confuse the power of the place you work with yourself.

    17. MS

      Mm-hmm.

    18. DC

      And so you, you get-

    19. MS

      Yes

    20. DC

      ... you dis- you get entangled-

    21. MS

      Yes

    22. DC

      ... where your identity and your work identity are the same thing.

    23. MS

      Yeah.

    24. DC

      And you just get really, I don't know, like you get confused about what's what.

    25. MS

      Yes.

    26. DC

      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]

    27. MS

      [laughs]

    28. DC

      Um, and then I think the self-aware people are aware of this.

    29. MS

      Yeah.

    30. DC

      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-

  13. 20:35 – 27:32

    Michael’s early lessons from civic work: incentives, bureaucracy, and tool-building gaps

    1. MS

      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.

    2. DC

      Yeah.

    3. MS

      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]

    4. DC

      That's what people think about tech, too.

    5. MS

      Yeah, yeah. [laughs]

    6. DC

      Where they th- they actually think that there's a lot more coordination.

    7. MS

      Yeah.

    8. DC

      There's not as much coordination as people think.

    9. MS

      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-

    10. DC

      It was a bad idea

    11. MS

      ... the right thing. [laughs]

    12. DC

      [laughs]

    13. MS

      Like, like it so reminds me of like listening to your users and your users being like-

    14. DC

      They want something bad.

    15. MS

      Yeah, like I want all the text on the website to be black and the background to be black. [laughs]

    16. DC

      Yeah.

    17. MS

      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.

    18. DC

      Hmm.

    19. MS

      Like, every time there's like one bad apple-

    20. DC

      Yeah, okay

    21. MS

      ... we are like-

    22. DC

      Yes

    23. MS

      ... "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]

    24. DC

      Well, big companies are run this way, where when something bad happens-

    25. MS

      Put a lot of rules in

    26. DC

      ... the scar tissue is to create rules to prevent that bad thing from ever happening again.

    27. MS

      But big companies can't do it as well as government.

    28. DC

      Yeah.

    29. MS

      Government can create rules that you can go to jail if you break. [laughs]

    30. DC

      No, that's what's crazy, is they, they're enforced by the police.

  14. 27:32 – 30:02

    Closing advice: decision-making prompts, giving back, and the story you want to tell

    1. MS

      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?

    2. DC

      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-

    3. MS

      Mm

    4. DC

      ... 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-

    5. MS

      Very much so, yes. [laughs]

    6. DC

      And I think there's a superpower we can all develop-

    7. MS

      Okay

    8. DC

      ... of crafting the prompts for ourselves-

    9. MS

      Mm

    10. DC

      ... and thinking about it that way when we're making decisions.

    11. MS

      Yes.

    12. DC

      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.

    13. MS

      Yeah.

    14. DC

      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-

    15. MS

      Mm

    16. DC

      ... what would I say?" 'Cause when I do that-

    17. MS

      Mm

    18. DC

      ... 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-

    19. MS

      Mm-hmm

    20. DC

      ... 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-

    21. MS

      Mm-hmm

    22. DC

      ... is a pretty good hack, man.

    23. MS

      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.

    24. DC

      [laughs]

    25. MS

      There are gonna be more of these. Have a great day.

    26. DC

      Thanks. Appreciate it, Michael. [outro music]

Episode duration: 30:03

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