At a glance
WHAT IT’S REALLY ABOUT
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.
IDEAS WORTH REMEMBERING
5 ideasLife 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.
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.
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.
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.
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.
WORDS WORTH SAVING
5 quotesYou 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
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