Dalton + Michael Return To YouTube
Michael Seibel (host), Dalton Caldwell (host)
In this episode of Dalton + Michael, featuring Michael Seibel and Dalton Caldwell, Dalton + Michael Return To YouTube explores seibel and Caldwell reflect on leaving YC and choosing change Dalton Caldwell and Michael Seibel explain why they became YC partner emeritus and what they are pursuing next: a new fund (Standard Capital) and hands-on work to help improve San Francisco.
Seibel and Caldwell reflect on leaving YC and choosing change
Dalton Caldwell and Michael Seibel explain why they became YC partner emeritus and what they are pursuing next: a new fund (Standard Capital) and hands-on work to help improve San Francisco.
They describe how specific conversations with trusted people can catalyze major life decisions when certain comments “stick” and replay in your mind over time.
Seibel shares early lessons from dozens of hours talking with city government, emphasizing that many public servants are capable, well-intentioned, and constrained by citizen-driven bureaucracy and human processes.
Caldwell highlights the identity and “status power” trap of prestigious institutions, and how leaving reveals whether respect was tied to you or your role.
They offer decision-making heuristics—high agency choices, “office hours with yourself,” and embracing uncomfortable growth—to avoid long-term regret and keep learning across life phases.
Key Takeaways
Life changes often start with a few “sticky” conversations.
They note that advice is common, but the lines you keep replaying (from a cofounder, spouse, or peer) usually indicate a deeper internal readiness to change.
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Predictability can be a warning sign once you’re secure.
Seibel’s cofounder argues that if you can “write the next 20 years,” it’s worth questioning whether comfort is crowding out exploration and growth.
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Choose high agency even when it’s harder.
Caldwell frames leaving YC and starting a firm as aligning with the same advice they gave founders: owning your calendar and decisions tends to produce more self-respect and better outcomes.
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New technology waves often reward starting from scratch.
They connect AI to prior platform shifts (mobile/iPhone): incumbents and pre-wave startups struggle to fully commit because existing revenue/processes create Innovator’s Dilemma friction.
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Prestige can distort identity and relationships.
Caldwell warns that people may confuse institutional power with personal capability; leaving tests what’s real when calls stop getting returned automatically.
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Government work is constrained, human, and often citizen-shaped.
Seibel reports surprise that many issues stem from voters demanding rules after failures; bureaucracy is frequently a response to public pressure, and frontline workers bear the cost.
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Use “better prompts” on yourself to decide faster and clearer.
Caldwell recommends treating decisions like LLM prompting: articulate constraints and then ask, “If I were doing office hours with myself, what would I say? ...
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Notable Quotes
“You could literally write everything that will happen between now and retirement if you stay at YC.”
— Michael Seibel (quoting his co-founder Justin)
“So are you gonna do anything for San Francisco?”
— Michael Seibel (quoting his wife Sarah)
“Most people who work in government are trying to do the right thing.”
— Michael Seibel
“We as citizens drive the bureaucracy.”
— Michael Seibel
“If I were doing office hours with myself—what would I say?”
— Dalton Caldwell
Questions Answered in This Episode
Dalton, what specifically made starting Standard Capital feel like “founding again” compared to being a YC partner—what changed day-to-day?
Dalton Caldwell and Michael Seibel explain why they became YC partner emeritus and what they are pursuing next: a new fund (Standard Capital) and hands-on work to help improve San Francisco.
Get the full analysis with uListen AI
Michael, in your 90–120 hours of conversations, what was the single most surprising example of a policy or rule that citizens pushed for and later regretted?
They describe how specific conversations with trusted people can catalyze major life decisions when certain comments “stick” and replay in your mind over time.
Get the full analysis with uListen AI
You both referenced the Innovator’s Dilemma with AI—what are the clearest signs a SaaS company is truly willing (or not willing) to cannibalize its current revenue to adapt?
Seibel shares early lessons from dozens of hours talking with city government, emphasizing that many public servants are capable, well-intentioned, and constrained by citizen-driven bureaucracy and human processes.
Get the full analysis with uListen AI
Dalton, how did you personally prepare for the “loss of institutional juice” when leaving YC, and what advice would you give someone afraid of losing status?
Caldwell highlights the identity and “status power” trap of prestigious institutions, and how leaving reveals whether respect was tied to you or your role.
Get the full analysis with uListen AI
Michael, what’s one concrete way tech people can help city government that doesn’t default to “build an app” or simplistic ‘dashboard’ thinking?
They offer decision-making heuristics—high agency choices, “office hours with yourself,” and embracing uncomfortable growth—to avoid long-term regret and keep learning across life phases.
Get the full analysis with uListen AI
Transcript Preview
I felt like for 20 years I had to be so just heads down in tech. I almost had to convince myself that those passions didn't exist.
Pretty much every founder I ever worked with at YC would always be like, "Dalton, when are you gonna do your own company again?"
[laughs] Perhaps my biggest regret is if one day I look back and I was like, "Oh, I didn't get to explore all those things."
I think I've always lived by the philosophy that if I just push myself really hard and I tried to do really good work with interesting people-
Yes
... interesting things would happen.
[upbeat music] All right. This is Dalton + Michael, and today we're gonna talk about life changes. Uh, I don't know about you, Dalton, I've had a couple life changes.
[laughs]
How about, how about you?
Yeah. There's a lot of, lot of new things.
Yeah.
Different environment here, changes for the viewers.
Yes, yes. There's a microphone, like, in our face-
[laughs]
... which is awkward. [laughs]
There's some differences.
Yes.
There's some differences.
Yes. So what are you up to nowadays?
Well, um, I'm now a partner emeritus at YC-
Mm-hmm
... and I've started a new VC firm called Standard Capital.
Big change.
Yeah, it's a big change.
Big, big change. For me, uh, as well, a partner emeritus, and so still a ton of office hours, which is kind of crazy, but it's been amazing. I've kind of been prodded to try to help make San Francisco better, and it's been an adventure.
That sounds really easy, fi- fixing San Francisco, Michael. Like, it's-
Well, as a tech bro-
[laughs]
... let me tell you. [laughs]
You all the answers, right? It's just that easy. You're the guy.
It, it, uh, it, it has been humbling to say the least. It's been so much fun getting to meet public servants and just learn something completely new. I think they're all a little surprised in the beginning of the conversation when I don't start with, like, tech bro answers, and, like-
[laughs]
... like, I don't come with my, like, recipe for, like, why aren't... What you're... You suck.
Have you thought about using AI?
And, yeah. [laughs] Have you thought about, have you thought about just doing these things? Have you thought, like, oh, like, there's a public safety pro- Have you thought about just deputizing all adult males and drafting them into a police force? Like-
Oof.
And so that's been really fun 'cause I think that people get a little disarmed when I'm like, "I don't know anything." Like, I like government. [laughs]
[laughs]
I believe in government, but I really don't know anything, and, you know, maybe one to 6% of the things I've learned in software and tech might be relevant.
Hmm.
And the rest is kind of new.
That's very humble of you. Uh, you're probably blowing their... They're like... Are, do they think you're tricking them?
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