5 Years of Dalton + Michael: What We've Learned Making Videos

1. MSMichael Seibel0:00

   If I were to go back in time and kinda give myself some advice on how to advise founders better, I think that I would be spending more time trying to help founders get between stages, get to the next stage, and less time trying to help founders optimize the stage that they're in. [upbeat music] All right. Welcome to Dalton + Michael: Throwback Edition. On this episode, we're gonna be talking about the lessons we've learned from the past five years of making startup videos. And I gotta be honest, when we started, I didn't think we'd be doing this for five years, and it doesn't feel like five years has passed. So-

2. DCDalton Caldwell0:41

   I didn't really have a vision for how long we'd be making these videos either, or that, that people would care about them. And I certainly didn't expect that this is probably what people know me the best for. Like, somehow this is, I guess, the most important thing I've done. [laughs] Which is-

3. MSMichael Seibel1:00

   Isn't that weird? [laughs]

4. DCDalton Caldwell1:03

   Not what I expected. And, you know, it's, it, it's cool 'cause everything I get when I talk to people are good vibes where, you know, the gist is it seems like we're having fun, it seems like we have these funny conversations and we enjoy chatting with each other. And I think people feel like they're a fly on the wall of, like, two friends talking about startups that have a lot of stories, and, um, people like that. So, so thank you for, for watching these. [laughs]

5. MSMichael Seibel1:29

   These videos have almost been awkwardly rewarding. I would say it's awkward because the number of times people will come up to us and say, "Hey, thank you for doing this," and it's like, it's, it's weird. And, you know, so I'll say, like, "Hey, thanks for watching," but, like, it is really fun to be able to have an impact in people's lives. And especially because, you know, we're in the startup ecosystem, you know, we've done some stuff. I feel like people who are aspiring to be where we are or even further than we, we, where we are, it's fun to kinda give them a little on-ramp, to give them a little, like, hey, like, you can be part of this too. And so, um, I think that part has been very, very surprising and rewarding. I think that maybe an interesting question to ask is what is some of the startup advice that, um, we're using ourselves?

6. DCDalton Caldwell2:21

   I mean, I think to start with, um, I think sometimes the people are, are joking about our videos. They're like, "Oh, you can just summarize them all by just do the thing." You know? Like, [laughs] like yeah, yeah. I get it, guys. Like, yet another video, another Dalton and Michael video that's like, "Don't overthink. Don't worry so much. Just do the thing." Fair criti- okay. Like, I can, I can ... I have no, um, pushback on that. But man, it's true. Just do the thing. And in my life, um-

7. MSMichael Seibel2:49

   By the way, I wanna, I wanna pause on that

8. DCDalton Caldwell2:50

   [laughs]

9. MSMichael Seibel2:51

   And, uh, you know, it's kind of like being, like, an, an athlete asking you, like, "How do I get faster?" And you say, like, "Go to the gym and train." And the athlete being like, "But you said that yesterday." And it's like, [laughs] that's, it's like, sure. But like [laughs] that's still the best way to do it. [laughs]

10. DCDalton Caldwell3:09

    And, and it's good to hear it. Again, the point of a coach is a coach being like, "Hey, you should keep running," you know? [laughs] Like, they're not actually gonna tell you stuff you've never heard before from the most part, but their job is to be repetitive and, and to hold you accountable, right? Like, their, the role a coach has in your life is not to say things you've literally never thought of before, right? Like, a- at least if you're at a, an advanced level. Maybe if you've, if you don't know how to shot put or something, the coach needs to tell you how to shot put. But at some point, you know, their, the job of a coach is to be repetitive in, in a, in a nice way.

11. MSMichael Seibel3:42

    Yes.

12. DCDalton Caldwell3:43

    And so I've gotten a lot of value of reminding myself of our own advice. Like, I think about the videos all the time that we made and what I would say, and so that's, I've been using that with, with, you know, my business and what I've been working on is just like, "Hey, stop overthinking, dude. Like, just go do the thing. Like, that's what you would tell people, so why aren't you doing it?" You know? [laughs] That voice is in my head all the time.

13. MSMichael Seibel4:04

    It's funny because as I do more and more kind of research and work in San Francisco government, you know, I find myself res- reaching for versions of MVPs all the time. And it's, like, really funny because a common train of th- conversation will be, "Here's a history of all of the super big projects that we've tried to do and failed." It's like, okay, good to know. Great. "Here's a spec for the next super big project that we're really excited to try to do." [laughs] And, and, you know, and it'll inevitably involve software because I'm around it. And, and, you know, I find myself constantly reaching for that, like, you- it's the, it's the Paul B- Paul Buchheit, right? What's the 90/10, right? With 10% of the work, can we make some freaking, can we, can we get something done here? And it's so surprising 'cause I think that people kind of ... And I might have expected myself to try to design grand solutions. I, I'm not convinced the world is built on grand solutions. Like, I'm not convinced that at any resolution it's not a bunch of 90/10 Legos. [laughs]

14. DCDalton Caldwell5:13

    Yeah. It's all a hack. Like, the more you know how technology works, it's like a bunch of hacks on top of hacks, and that's just, that's just how it works, right? Um-

15. MSMichael Seibel5:22

    Well, and that's government. And I think that's what's so funny is I think that, like, in the American culture, government is kind of simultaneously ridiculed but presented as this kind of pristine, almost, like, spiritual thing. And it's kind of like, no, it's a human organization. Y- you ... Point to me at a human organization and show me how it's spiritual and pristine, and like, yeah, well, I, I don't think you can find one. So I think that's been really fun is been, like, one, bringing an MVP culture, but then two, being able to deliver the fast wins that MVP culture can, like, you know, like, it's really motivational to iterate on something that actually moved the bar a little bit. So I think that's been really, really fun too. Other things that come to mind after five years?

16. DCDalton Caldwell6:05

    I think everyone-... knows our advice, but they still wanna hear it anyway. [laughs] And I like to think about it, um, too, and sometimes they go back to watch the old videos. It's almost like listening to an old song. Like, somehow, [laughs] somehow even if you know the answers or you've seen the video, there's something calming and meditative about remembering the basics and focusing-

17. MSMichael Seibel6:33

    Yeah

18. DCDalton Caldwell6:33

    ... on the basics. So again, this is-

19. MSMichael Seibel6:35

    Yes

20. DCDalton Caldwell6:35

    ... this is... When I come to our own videos or when I come to our own advice and I think about our conversations over the years, I'm always just trying to think about the basics and first principles thinking, and getting out of my head of s- you know, spinning out and creating super complicated solutions or super complicated scenarios, you know? So I guess simple thinking is my summary of the, of the thing that stuck with me.

21. MSMichael Seibel7:00

    I think for me probably the last thing that stuck with me is looking back, we've worked at companies at all these different stages. And at every stage in a startup, it's stressful, things feel existential, um, at every stage. But fundamentally, the stages are different. And I think that maybe if I were to go back in time and kinda give myself some advice on how to advise founders better, I think that I would be spending more time trying to help founders get between stages, get to the next stage, and less time trying to help founders optimize at the stage that they're in. I've met a lot of companies where I feel as though engaging in the question of how you could actually be a big, successful company is h- is too hard. Th- there's some, maybe some truths that we don't wanna talk about there. So instead, we'll kind of engage in easier questions like, how do you hit your monthly growth goal? Or how do you, like, add another million ARR, right? Like, and we won't tackle the major stuff. And I think the other thing that comes to mind on my front is that, like, it turns out to be a great company, you have to be great at the later stages. It's like, it's funny, like I, I, I love Michael Jordan kind of videos and kinda stories and so on and so forth. He was my favorite athlete. And there are all these stories about one, like how Michael Jordan could lock in in the regular season, right? So it wasn't like he was coasting, but then, like, two, how he became an even better player in the playoffs. [laughs] Like, like his average got, went up. I almost want to inspire founders to be on that arc, and I almost feel like sometimes founders imagine a different arc. Like, the hard stuff is now. Like, they, they invert that arc. Like, oh, the really hard stuff, the NBA final thing is where I'm starting, and every step it's gonna be easier and easier. And by the end, it's gonna feel like I'm playing a preseason game. And I'm like, "No. No, no, no, no." [laughs] Why? And so I think, I think if I would go back in time I would kind of emphasize that more 'cause I think that the folks who have the right mindset, they're just more resilient. And, like, they're, they think bigger, they can execute bigger. It's almost like they're flying in, like, clearer air.

22. DCDalton Caldwell9:18

    We always are honest with folks, but-

23. MSMichael Seibel9:20

    Yeah

24. DCDalton Caldwell9:21

    ... let's just talk about the numbers. The actual number of really big startups that make it, um, is small. [laughs] And we're always honest about that. And to me, our main message, is it still worth trying if you're having fun and you're following the fundamentals? And that-

25. MSMichael Seibel9:40

    Yes

26. DCDalton Caldwell9:40

    ... something awesome will happen with your life. Like-

27. MSMichael Seibel9:43

    Yes.

28. DCDalton Caldwell9:44

    [laughs] Like, something cool will happen by using-

29. MSMichael Seibel9:47

    Yes

30. DCDalton Caldwell9:47

    ... these tools and going-

Episode duration: 13:01