Dalton + Michael5 Years of Dalton + Michael: What We've Learned Making Videos
CHAPTERS
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.
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