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

If I had to go back in time and kind of 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. All right. Welcome to Dalton plus Michael throwback edition. On this episode, we're going to be talking about the lessons we've learned from the past 5 years of making startup videos.

And I got to be honest, when we started, I didn't think we'd be doing this for 5 years. It doesn't feel like 5 years has passed. So, 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. >> Isn't that weird? >> Not what I expected.

And you know, it's it it's cool cuz 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. >> 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 kind of 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. >> 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 Like, "Yeah, yeah, I get it, guys.

Like yet another video another Dothan Michael video that's like don't overthink. Don't worry so much. Just do the thing." Fair critique. 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 >> By the way, I would I want to pause on that. It 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 that's it's like sure, but like that's still the best way to do it. >> 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." Like, they're not actually going to 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 the >> The role a coach has in your life is not to say things you've literally never thought of before, right? Like at least if you're at 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, there the job of a coach is to be repetitive in in a in a nice way. >> 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?" That voice is in my head all the time. >> It's funny because as I do more and more kind of research and work in San Francisco government, you know, I find myself rece- reaching for versions of MVPs all the time. And it's like really funny because a common train of conversation will be "Here's the 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." 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 know, it's the it's the Paul B- Paul Bucheit, 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 cuz 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. >> 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 >> Well, and that's government. And I think that's what's so funny is I think that like in 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. Like, point to me at a human organization and show me how it's spiritual and pristine." And like, you know, what I don't think you can find one. So, I think that's been really fun is been like one bringing in 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 move the bar a little bit.

So, I think that's been really really fun to hear. Other things that come to mind after 5 years? >> I think everyone knows our advice, but they still want to hear it anyway. 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 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 on the basics. >> So, again, this is 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 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. >> 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 like essential um at every stage, but fundamentally the stages are different.

And I think that maybe if I were to go back in time and kind of 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. 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 is too hard.

There's some maybe some truths that we don't want to 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 and the other thing that came to mind in 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 love Michael Jordan kind of videos and kind of stories and so 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. 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 going to be easier and easier. And by the end it's going to feel like I'm playing a preseason game." And I'm like, "No. No, no, no, no. And so, I think I think if I would go back in time, I would kind of emphasize that more cuz 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 clear air. We always are honest with folks. But let's just talk about the numbers. The actual number of really big startups that make it um is small. And we're always honest about that. And to me, our main message is it's still worth trying if you're having fun and you're following the fundamentals? And that something awesome will happen with your life.

Like >> Yes. >> Like something cool will happen by using these tools and going on an adventure and and you know, working with a co-founder and trying to help people that kind of like no matter what path it takes, if you do it the right way, the the fight is still worth fighting. And I I stand by that. But my reaction what you're saying, which is is just the grim math of of reality here, just like there aren't 10,000 Michael Jordans out there, right?

There there is not that many um really big companies. And again, I just I've always tried to bridge the gap between telling anyone that watches these videos there's room for you here, we want you here, there's a seat at the table. You you should be a founder if you want to be, you know, like basically the opposite of gatekeeping has always been one of the messages I've been trying to do. And we have to go mind that with being honest.

And again, maybe we keep using the sports thing. Like I think sports is awesome for kids growing up and you learn a lot. And I have my kids doing sports. And I know the odds and probably they're not going to be professional athletes. And those are both true statements, right? >> Yeah, I agree. And I and I think that the piece of advice that I would give somebody who really really wants to win is like think about how do you win in games when so few people win.

Like think about how those types of games are different from games where lots of people win. We always talk about this idea of are you doing the the average of what the 10 people or 20 or 50 people around you are doing? And like in some games, that's a great winning strategy. In other games, that's the exact wrong strategy. I think that like I wish if I would go back in time, I I have you know, we get to work with really smart people.

I would have kind of engaged them at an intellectual level on what kind of tactics work in games with so few winners. Cuz I think I might have been able to kind of like addict people to the like intellectual strategy part of that. As opposed to I fear what happens too often is addicting people to the next month's growth goal. >> It's almost like chess. I'm not a good chess player, but basically you can be pretty good if you just memorize a bunch of opening moves and beat most people.

But the meta game to be great at chess, I think is just totally different. Like there's a whole different meta game to be a really, really, really good chess player versus someone that you know can beat everyone in their hometown. >> What I fear is that people are practicing a game that can make them a top 10% founder or give them a top 10% outcome. But like they're not even practicing the game that could help produce a top 1% or 0.1% outcome.

And it's like in a power law distribution of rewards, being in the top 10% is not good enough. >> Well, it's good, but you probably will always wonder if you could have gone farther, yes. You know, that that's probably what I would say. But it's still good. >> Still good. >> It's still good. >> All right, great chat, Dalton. >> All right, thanks Michael.