Dalton + Michael5 Years of Dalton + Michael: What We've Learned Making Videos
Michael Seibel on five-year retrospective: simple execution, MVP thinking, and stage transitions matter.
In this episode of Dalton + Michael, featuring Michael Seibel and Dalton Caldwell, 5 Years of Dalton + Michael: What We've Learned Making Videos explores five-year retrospective: simple execution, MVP thinking, and stage transitions matter Their most repeated advice—“just do the thing”—isn’t novel but works like coaching: repetition builds execution and accountability.
At a glance
WHAT IT’S REALLY ABOUT
Five-year retrospective: simple execution, MVP thinking, and stage transitions matter
- Their most repeated advice—“just do the thing”—isn’t novel but works like coaching: repetition builds execution and accountability.
- They apply startup fundamentals to their own work, especially MVP/90-10 thinking, emphasizing small, fast wins over grand, brittle plans (even in government contexts).
- They argue that founders should focus more on progressing between startup stages than on optimizing within a stage, because the hard problems change as companies scale.
- They stress the reality of power-law outcomes: very few startups become huge, so founders who want to truly “win” must practice a different meta-game than hitting incremental monthly metrics.
- They aim to be welcoming and anti-gatekeeping while still being honest about the odds, framing startups as an “adventure” that can be worth it even without a world-beating outcome.
IDEAS WORTH REMEMBERING
5 ideasRepetitive fundamentals beat novel advice.
They compare startup guidance to athletic coaching: the value is often reinforcement and accountability, not hearing something you’ve never heard before.
Execution starts when you stop overthinking.
Dalton notes he uses their own voice in his head as a corrective—if you’d tell founders to act, you should do the same in your own business.
Use MVP/90-10 building blocks to create momentum.
Michael describes applying MVP thinking in San Francisco government by seeking the smallest version that produces a real “bar moved” outcome, then iterating from there.
Most “grand solutions” are stacks of practical hacks.
They argue the world—tech and institutions alike—is largely built from incremental, imperfect components, so insisting on pristine designs can block progress.
Optimize stage transitions, not just stage performance.
Michael wishes he’d spent more time helping founders get to the next stage (where the game changes) rather than polishing metrics within the current stage.
WORDS WORTH SAVING
5 quotesMan, it's true. Just do the thing.
— Dalton Caldwell
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.
— Michael Seibel
At every stage in a startup, it's stressful, things feel existential, um, at every stage. But fundamentally, the stages are different.
— Michael Seibel
I almost feel like sometimes founders imagine a different arc. Like, the hard stuff is now. Like, they, they invert that arc.
— Michael Seibel
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.
— Michael Seibel
QUESTIONS ANSWERED IN THIS EPISODE
5 questionsWhat are concrete examples of “between-stage” moves founders should prioritize over optimizing current metrics?
Their most repeated advice—“just do the thing”—isn’t novel but works like coaching: repetition builds execution and accountability.
How would you define the “meta-game” for top 0.1% outcomes—what behaviors change compared to top 10% founders?
They apply startup fundamentals to their own work, especially MVP/90-10 thinking, emphasizing small, fast wins over grand, brittle plans (even in government contexts).
In your experience, which common monthly goals (growth, ARR, engagement) most often distract teams from the harder “can this be huge?” questions?
They argue that founders should focus more on progressing between startup stages than on optimizing within a stage, because the hard problems change as companies scale.
What’s a practical 90/10 MVP approach you’d recommend for a non-startup institution (like a city department) trying to deliver fast wins?
They stress the reality of power-law outcomes: very few startups become huge, so founders who want to truly “win” must practice a different meta-game than hitting incremental monthly metrics.
How do you balance anti-gatekeeping (“there’s room for you”) with honesty about the grim math without demotivating capable founders?
They aim to be welcoming and anti-gatekeeping while still being honest about the odds, framing startups as an “adventure” that can be worth it even without a world-beating outcome.
Chapter Breakdown
Five years of startup videos: unexpected longevity and impact
Michael and Dalton reflect on reaching the five-year mark, admitting they didn’t anticipate the series lasting or becoming such a defining part of their public identities. They share how surprising and rewarding it is to hear directly from viewers who’ve benefited from the conversations.
“Just do the thing”: why their simplest advice keeps repeating
They address the common joke that all their videos boil down to “do the thing.” Dalton agrees the critique is fair—then argues that repetition is precisely the point because execution beats rumination in startups.
Coaching as repetition and accountability, not novelty
Michael and Dalton compare startup advice to athletic coaching: you don’t get new secrets every day, you get reinforcement and accountability. The value is hearing the basics repeatedly until behavior changes.
Using their own advice on themselves: the “inner coach” effect
Dalton explains that their videos have become a tool for self-correction—he often catches himself overthinking and recalls what he’d tell a founder. The work is applying your own principles under real pressure.
MVP culture outside startups: applying 90/10 thinking in government
Michael describes bringing MVP thinking into San Francisco government work, where big “grand projects” often fail. He leans on Paul Buchheit’s 90/10 framing: get meaningful progress with a small, focused slice of effort.
“Everything is a hack”: demystifying systems and organizations
They broaden the point: technology and institutions are stacks of hacks and workarounds, not pristine designs. Michael adds that government is a human organization like any other—messy, iterative, and improvable.
Why people rewatch: fundamentals as calming “old songs”
Dalton notes people already know the advice, yet still return to it because it’s grounding—like replaying a familiar song. They frame this as a meditative return to first principles and simple thinking.
Stage transitions matter more than optimizing within a stage
Michael shares his biggest hindsight lesson for advising founders: focus less on optimizing where they are and more on helping them move to the next stage. Many companies avoid the hardest “how do we become huge?” questions by substituting easier, local optimizations.
The myth that it gets easier: greatness requires later-stage excellence
Using Michael Jordan as an analogy, Michael argues the best get better under higher stakes—especially in the “playoffs” (later stages). Many founders assume the opposite arc: that the hardest part is at the beginning and everything gets easier later.
Non-gatekeeping plus honest odds: the adventure is still worth it
Dalton emphasizes balancing encouragement with realism: very few startups become huge, but pursuing startups can still lead to a meaningful, exciting life. Like youth sports, the odds of going pro are low, yet the activity is still valuable.
Winning in power-law games: don’t train for top 10% if you want top 1%
Michael argues that in games with very few winners (power-law rewards), “do what everyone around you does” can be the wrong strategy. He wishes he’d engaged founders more on the intellectual strategy of rare-winner games rather than getting them fixated on near-term metrics.
Chess and the meta-game: moving beyond memorized playbooks
Dalton likens startup tactics to chess openings: memorization can beat most people locally, but elite performance requires a different meta-game. They close by affirming that “still good” outcomes matter, while acknowledging many founders may wonder how far they could’ve gone.
EVERY SPOKEN WORD
Install uListen for AI-powered chat & search across the full episode — Get Full Transcript
Get more out of YouTube videos.
High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.
Add to Chrome