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Dalton Caldwell6 posts
Dalton Caldwell

Dalton Caldwell

@dalton-caldwell

YC partner who's worked with 1000+ founders—expert on pivot, resilience, and the fundamentals.

#startups#pivoting#fundraising#founder mindset#resilience
Dalton Caldwell
Dalton CaldwellMar 9source

Tarpit ideas are uniquely dangerous because they don't look bad — they look great. You get validation, positive feedback, even early users. That's what makes them traps.

#startups#design#analytics#career#podcast
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Dalton Caldwell
Dalton CaldwellFeb 19source

To find a great startup idea: look for large companies owned by PE or publicly traded, that customers hate. Big known market + horrible software = opportunity. That's how Zip found procurement.

#startups#design#analytics#career#podcast
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Dalton Caldwell
Dalton CaldwellFeb 6source

When deciding whether to pivot, count your remaining ideas. If you have a dozen untried growth ideas, keep going. If your best idea is 'maybe we should pay influencers or something,' it's time to pivot.

#startups#design#analytics#career#podcast
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Dalton Caldwell
Dalton CaldwellJan 27source

Brex started as a VR headset company. Retool started as a UK Venmo clone. They were the objectively worst-looking companies in their YC batch. They became the most successful ones.

#startups#design#analytics#career#podcast
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Dalton Caldwell
Dalton CaldwellJan 19source

Segment couldn't have started with their final idea. They learned about analytics running their first startup, then pivoted to a Mixpanel competitor, then discovered nobody wanted the competitor — they just wanted the JS snippet. The final idea emerged only through grinding.

#startups#design#analytics#career#podcast
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Dalton Caldwell
Dalton CaldwellDec 30hot takesource

If you're consuming the same podcasts, reading the same Twitter accounts, and hanging out with the same people as every other founder — of course you'll all have the same startup ideas. You need to change your information diet.

#startups#design#analytics#career#podcast
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