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Dalton Caldwell is Managing Director and Group Partner at Y Combinator. Prior to YC, he was the co-founder and CEO of imeem (acquired by MySpace in 2009) and the co-founder and CEO of App.net. During his time at YC, he\u2019s advised more than 35 YC unicorns, including DoorDash, Amplitude, Webflow, and Retool, and has worked across 21 different YC batches. He\u2019s also racked up more than 6,500 office hours with founders. In our conversation, we discuss:

\u2022 Why founders need to adopt the mindset \u201cJust don\u2019t die\u201d

\u2022 The most common reason startups fail

\u2022 When to pivot, and characteristics of a good pivot

\u2022 The concept of \u201ctar pit ideas\u201d and examples of bad startup ideas

\u2022 Why investors say no to startups

\u2022 The importance of market size in investment decisions

\u2022 The pitfalls of founders over-delegating

\u2022 Effective ways to talk to customers

\u2022 20 ideas Dalton is looking to fund

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Brought to you by:

\u2022 Eppo\u2014Run reliable, impactful experiments

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\u2022 Coda\u2014The all-in-one collaborative workspace

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Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups

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Where to find Dalton Caldwell:

\u2022 X: https://twitter.com/daltonc

\u2022 LinkedIn: https://www.linkedin.com/in/daltoncaldwell/

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Where to find Lenny:

\u2022 Newsletter: https://www.lennysnewsletter.com

\u2022 X: https://twitter.com/lennysan

\u2022 LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Dalton\u2019s background

(04:41) The value of simple advice

(07:04) Dalton\u2019s advice: \u201cJust don\u2019t die\u201d

(08:39) Knowing when to stop

(11:45) Deciding to pivot

(14:26) Characteristics of a good pivot

(17:53) Knowing when to pivot

(19:03) Zip\u2019s journey and finding a market

(21:22) Why Dalton says to \u201cMove towards the mountains and the desert\u201d

(23:45) Tar pit ideas

(26:49) Understanding why investors say no

(29:14) The importance of market size

(32:16) Avoiding over-delegation and hiring senior people too early

(36:43) Why startups fail

(40:30) Effectively talking to customers

(45:17) Examples of startups hustling to talk to customers

(48:01) Patterns of successful startups

(52:05) YC\u2019s Request for Startups

(55:37) Early days of Silicon Valley

(01:05:33) Contrarian corner: growth hacking for early startups

(01:09:28) Failure corner

(01:11:15) Closing thoughts

(01:12:22) Lightning round

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Referenced:

\u2022 Y Combinator: https://www.ycombinator.com/

\u2022 Tiger Woods\u2019s website: https://tigerwoods.com/

\u2022 Co-Founder Mistakes That Kill Companies & How to Avoid Them: https://www.youtube.com/watch?v=dlfjs_eEEzs

\u2022 Daniel Alberson\u2019s LinkedIn post about Y Combinator: https://www.linkedin.com/posts/alberson_i-left-my-dream-job-as-a-product-manager-activity-7089677882431533056-jJ9H

\u2022 Companies in Y Combinator W17 Batch: https://www.ycdb.co/batch/w17

\u2022 Brex: https://www.brex.com/

\u2022 Retool: https://retool.com/

\u2022 Segment: https://segment.com/

\u2022 Mixpanel: https://mixpanel.com/

\u2022 Whatnot: https://www.whatnot.com/

\u2022 Andreessen Horowitz: https://a16z.com/

\u2022 Airbnb\u2019s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/

\u2022 Rujul Zaparde on LinkedIn: https://www.linkedin.com/in/rujulz/

\u2022 Zip: https://ziphq.com/

\u2022 Lu Cheng on LinkedIn: https://www.linkedin.com/in/lu-cheng-973b7830/

\u2022 Avoid these tempting startup tar pit ideas: https://www.ycombinator.com/library/Ij-avoid-these-tempting-startup-tarpit-ideas

\u2022 Airbnb acquires Localmind to create crowdsourced advice about neighborhoods: https://skift.com/2012/12/13/airbnb-acquires-localmind-to-create-crowdsourced-advice-about-neighborhoods/

\u2022 Foursquare: https://foursquare.com/

\u2022 Razorpay: https://razorpay.com/

\u2022 Total Addressable Market: https://www.productplan.com/glossary/total-addressable-market/

\u2022 Lenny Bogdonoff on LinkedIn: https://www.linkedin.com/in/rememberlenny/

\u2022 Milk Video: https://milkvideo.com/

\u2022 Lessons from working with 600+ YC startups | Gustaf Alstr\xf6mer (Y Combinator, Airbnb): https://www.lennyspodcast.com/lessons-from-working-with-600-yc-startups-gustaf-alstromer-y-combinator-airbnb/

\u2022 How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups

\u2022 Collison installation: https://news.ycombinator.com/item?id=18400504

\u2022 Stripe: https://stripe.com/

\u2022 Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/

\u2022 John Collison on LinkedIn: https://www.linkedin.com/in/johnbcollison/

\u2022 Tony Xu on LinkedIn: https://www.linkedin.com/in/xutony/

\u2022 Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine/

\u2022 Ryan Petersen on LinkedIn: https://www.linkedin.com/in/rpetersen/

\u2022 Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/

\u2022 YC\u2019s latest Request for Startups: https://www.ycombinator.com/blog/ycs-latest-request-for-startups

\u2022 ERPs: https://www.ycombinator.com/rfs#new-enterprise-resource-planning-software

\u2022 Commercial open source companies: https://www.ycombinator.com/rfs#commercial-open-source-companies

\u2022 New space companies: https://www.ycombinator.com/rfs#new-space-companies

\u2022 A way to end cancer: https://www.ycombinator.com/rfs#a-way-to-end-cancer

\u2022 Spatial computing: https://www.ycombinator.com/rfs#spatial-computing

\u2022 New defense technology: https://www.ycombinator.com/rfs#new-defense-technology

\u2022 Bringing manufacturing back to America: https://www.ycombinator.com/rfs#bring-manufacturing-back-to-america

\u2022 Better enterprise glue: https://www.ycombinator.com/rfs#better-enterprise-glue

\u2022 Small fine-tuned models, as an alternative to giant generic ones: https://www.ycombinator.com/rfs#small-finetuned-models-as-an-alternative-to-giant-generic-ones

\u2022 Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/

\u2022 Sam Altman on X: https://twitter.com/sama

\u2022 Sean Parker on LinkedIn: https://www.linkedin.com/in/parkersean/

\u2022 Owen Van Natta on LinkedIn: https://www.linkedin.com/in/owen-van-natta-444a7/

\u2022 Marc Andreessen on X: https://twitter.com/pmarca

\u2022 Picplz 1, Instagram 0 as VC firm Andreessen Horowitz chooses photo app rival: https://www.reuters.com/article/idUS2587232395/

\u2022 Gustaf Alstromer\u2014How to Get Users and Grow: https://www.youtube.com/watch?v=T9ikpoF2GH0

\u2022 Getting to Yes: Negotiating Agreement Without Giving In: https://www.amazon.com/Getting-Yes-Negotiating-Agreement-Without/dp/0143118757

\u2022 Founding Sales: The Early Stage Go-to-Market Handbook: https://www.amazon.com/Founding-Sales-Go-Market-Handbook-ebook/dp/B08PMK17Z1

\u2022 Founder-led sales | Pete Kazanjy (Founding Sales, Atrium): https://www.lennyspodcast.com/founder-led-sales-pete-kazanjy-founding-sales-atrium/

\u2022 The Sopranos on HBO: https://www.hbo.com/the-sopranos

\u2022 The Wire on HBO: https://www.hbo.com/the-wire

\u2022 Columbo on Prime Video: https://www.amazon.com/Columbo-Season-1/dp/B008SA89HA

\u2022 Oura ring: https://ouraring.com/

\u2022 Apple watch: https://www.apple.com/watch/

\u2022 SiPhox: https://siphoxhealth.com/

\u2022 Dalton & Michael on YouTube: https://www.youtube.com/playlist?list=PLQ-uHSnFig5Nd98Sc9I-kkc0ZWe8peRMC

\u2022 How Future Billionaires Get Sh*t Done: https://www.youtube.com/watch?v=ephzgxgOjR0

\u2022 The Student\u2019s Guide to Becoming a Successful Startup Founder: https://www.youtube.com/watch?v=O5KCB2p6SB8

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.