Lessons from 1,000+ YC startups: Pivoting, resilience, avoiding tar pit ideas, more | Dalton Caldwell (Y Combinato…

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Lessons from 1,000+ YC startu…

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Lessons from 1,000+ YC startups: Pivoting, resilience, avoiding tar pit ideas, more | Dalton Caldwell (Y Combinator, Managing Director)

Lenny Rachitsky

Apr 18

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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’s advised more than 35 YC unicorns, including DoorDash, Amplitude, Webflow, and Retool, and has worked across 21 different YC batches. He’s also racked up more than 6,500 office hours with founders. In our conversation, we discuss:

Why founders need to adopt the mindset “Just don’t die”
The most common reason startups fail
When to pivot, and characteristics of a good pivot
The concept of “tar pit ideas” and examples of bad startup ideas
Why investors say no to startups
The importance of market size in investment decisions
The pitfalls of founders over-delegating
Effective ways to talk to customers
20 ideas Dalton is looking to fund

Some takeaways:

The defining trait of successful founders isn’t a specific personality type but rather a profound self-belief. They possess an unwavering conviction in their startup’s potential, even in the face of daunting obstacles. Refusing to accept failure, they persuade others of their inevitable success.
Beware of “tar pit ideas”: ideas that receive initial positive feedback but may lead to long-term challenges. These ideas often seem appealing and solve what appears to be an unsolved problem, attracting many people to pursue them. However, despite the positive feedback and validation, they can become difficult to pivot away from once their limitations become apparent. Understanding the distinction between a genuinely innovative startup idea and one that merely garners initial enthusiasm can save founders time, resources, and energy in the long run, steering them toward more promising ventures.
A successful pivot often entails focusing on familiar problems and refining previous solutions. Companies like Brex and Segment thrived after significant pivots that drew on founders’ prior experiences and insights gained from initial concepts.
If your venture struggles and innovative strategies are exhausted, consider pivoting. But if there are still untapped ideas, persevere and try them first.
If an investor likes aspects of a startup, they may still say no because they are waiting for opportunities that meet a higher bar. Dalton says to put yourself in the shoes of investors and consider what decisions they would make if they were in that position. This perspective can help founders understand that rejections aren’t necessarily a reflection of lack of belief in their idea but rather a result of investors seeking the most promising opportunities given their constraints.

Listen now on Apple, Spotify, Overcast, and YouTube.

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

Where to find Dalton Caldwell:

• X: https://twitter.com/daltonc

• LinkedIn: https://www.linkedin.com/in/daltoncaldwell/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Dalton’s background

(04:41) The value of simple advice

(07:04) Dalton’s advice: “Just don’t die”

(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’s journey and finding a market

(21:22) Why Dalton says to “Move towards the mountains and the desert”

(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’s 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

Referenced:

• Y Combinator: https://www.ycombinator.com/

• Tiger Woods’s website: https://tigerwoods.com/

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

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

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

• Brex: https://www.brex.com/

• Retool: https://retool.com/

• Segment: https://segment.com/

• Mixpanel: https://mixpanel.com/

• Whatnot: https://www.whatnot.com/

• Andreessen Horowitz: https://a16z.com/

• Airbnb’s 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/

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

• Zip: https://ziphq.com/

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

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

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

• Foursquare: https://foursquare.com/

• Razorpay: https://razorpay.com/

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

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

• Milk Video: https://milkvideo.com/

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

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

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

• Stripe: https://stripe.com/

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

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

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

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

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

• 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/

• YC’s latest Request for Startups: https://www.ycombinator.com/blog/ycs-latest-request-for-startups

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

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

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

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

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

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

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

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

• 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

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

• Sam Altman on X: https://twitter.com/sama

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

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

• iMeme: https://apps.apple.com/us/app/imeme-generator/id1560021364

• Marc Andreessen on X: https://twitter.com/pmarca

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

• Gustaf Alstromer—How to Get Users and Grow: https://www.youtube.com/watch?v=T9ikpoF2GH0

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

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

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

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

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

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

• Oura ring: https://ouraring.com/

• Apple watch: https://www.apple.com/watch/

• SiPhox: https://siphoxhealth.com/

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

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

• The Student’s Guide to Becoming a Successful Startup Founder: https://www.youtube.com/watch?v=O5KCB2p6SB8

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

Lenny may be an investor in the companies discussed.

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Taking Down a Nuclear War Liar

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Taking Down a Nuclear War Liar

A lie can get halfway around the world before the truth can get it shoes on

Ryan McBeth

Apr 17

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Twitter user Chuck Callesto describes himself as a “| Father | Social Media Strategist” he should add “Liar” to that list.

On or about 3:00 PM ET, Chuck posted on Twitter:

“SHOCK VIDEO: ⚠️ B-52H long-range bombers being loaded with nuclear warheads..

IS THIS WHAT’S NEXT?”

Original tweet here.

This tweet is 100% false. The footage is from an exercise at Minot AFB which was recorded on the US Government media site DIVDS. Titled: “Exercise Prairie Vigilance/Bayou Vigilance 24-3 705th Munitions Squadron night operations”

It looks like this was originally taken from Spreader Account “Monitor X”

https://twitter.com/MonitorX99800/status/178031103262111746

Who originally got this from sentinel Telegram Account WW3.INFO Battlefield Research.

The exact text and video have made their way to multiple locations around Twitter.

If you don’t know what you are looking at, don’t share it. If something makes you feel emotional, don’t share it. Think before you click.

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Edward Lance Lorilla