Dalton + Michael

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

In this episode of Dalton + Michael, we reflect on making startup advice videos for YouTube since 2021. We've spoken to hundreds of founders that have watched the videos and heard lots of feedback. We also discuss what advice we bring into our own daily lives. This is a throwback episode of Dalton + Michael, recorded in the style of the original episodes. A new studio is coming soon. Dalton + Michael is brought to you by @Standard_Cap Dalton Caldwell on X: https://x.com/daltonc Michael Seibel on X: https://x.com/mwseibel

Michael SeibelhostDalton Caldwellhost

Apr 26, 202613mWatch on YouTube ↗

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 ideas

Repetitive 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 quotes

Man, 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

Repetition as coaching and accountability“Just do the thing” and avoiding overthinkingMVP culture and Paul Buchheit’s 90/10 ideaFast iteration and small wins vs grand designsStartup stages and transitioning to the next stagePower-law outcomes and “games with few winners”Anti-gatekeeping plus honest odds of success

High quality AI-generated summary created from speaker-labeled transcript.

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.