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Dalton Caldwell

Dalton Caldwell

Partner at Y Combinator; founder of imeem

Every podcast episode featuring Dalton Caldwell that Attunex has found: 76 interviews and appearances across 12 shows between 2012 and 2025. Most often on Y Combinator Startup Podcast (36), Dalton & Michael (25) and Founders Talk: Startups, CEOs, Leadership (3). Often in conversation with Michael Seibel. Follow Dalton in Attunex to get new appearances automatically, each with an on-device transcript and summary.

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Updated 2026-10-14.

  1. #396 Max: Non-Consensus Coding (How to Find Billion-Dollar AI Startup Ideas)
    AI Fire DailyAI

    In March 2026, the hard part is no longer building the product—it's figuring out what to build in a world where AI Wrappers are collapsing. 🛠️ With agentic coding tools like Cursor and Lovable…

    2026-03-26
  2. 160. Դասեր 1000+ YC startup-ներից | Dalton Caldwell
    ProdCast

    Send us Fan Mail Այս էպիզոդում Dalton Caldwell-ը կիսվում է YC-ում տեսած ամենակարևոր դասերով։ Քննարկվում են pivot-ները, tar pit ideas-ը և founder resilience-ը։ Support the show

    2025-08-25
  3. Building A $2 Billion SaaS Company: Lessons From A Two Time Founder
    Y Combinator Startup Podcast

    Two-time founder Rujul Zaparde knows a thing or two about resilience and learning from failure. After dropping out of college to build FlightCar, he worked as a PM at Airbnb, and later as a visiting…

    2025-01-08
  4. How To Influence Decision Makers
    Dalton & Michael

    Whether it's career advancement, leaving a positive mark at an org, or raising funds for your startup, the ability to convince and influence decision-makers is a vital skillset to develop. In this…

    2024-11-16
  5. The Problem With Startup "Experts"
    Dalton & Michael

    Despite the most successful tech founders being centralized in the Bay Area, there are founders, accelerators, and investors located around the world. In this video, Dalton Caldwell and Michael…

    2024-11-16
  6. Stop Innovating (On The Wrong Things)
    Dalton & Michael

    Startups need to innovate to succeed. But not all innovation is made equal and reinventing some common best practices could actually hinder your company. In this episode, Dalton Caldwell and Michael…

    2024-11-16
  7. Should Your Startup Bootstrap or Raise Venture Capital?
    Dalton & Michael

    Within the world of startups, you'll find lots of discourse online about the experiences of founders bootstrapping their startup versus the founders who have raised venture capital to fund their…

    2024-11-16
  8. Do Technical Founders Need Business Co-Founders?
    Dalton & Michael

    Whether or not you need a co-founder is always a hotly debated topic — but going one level deeper, founders often wonder what kind of co-founder they need. It’s also common for technical founders to…

    2024-11-16
  9. Techno Optimism, Explained
    Dalton & Michael

    Social media often promotes a doom and gloom outlook about our future society. But is that worldview accurate? In this episode, Dalton Caldwell and Michael Seibel discuss the best ways for founders…

    2024-11-16
  10. Should You Quit Your Job At A Unicorn?
    Dalton & Michael

    If you’re an employee of a late stage company right now, how would you know when it’s time to move on vs. time to double down? The fact is there isn't an easy answer — it can really vary from person…

    2024-11-16
  11. Why You Shouldn't Copy Your Tech Idols
    Dalton & Michael

    Do famous founders give advice they didn't follow themselves? How seriously should you consider the advice of people like Elon Musk, Sam Altman and Peter Thiel? It’s hard not to give advice when…

    2024-11-16
  12. Does Your Startup Need To Be In San Francisco?
    Dalton & Michael

    Should you and your startup live in San Francisco? Y Combinator Partners, Michael Seibel and Dalton Caldwell, debate their different opinions on whether startups are more likely to succeed in the…

    2024-11-16
  13. Will OpenAI Kill All Startups?
    Dalton & Michael

    How will the rise of AI impact startups and entrepreneurs? Join Michael Seibel and Dalton Caldwell for a discussion on the opportunities and challenges AI brings for founders. Through the lens of…

    2024-11-16
  14. How Generosity Built Tech Giants
    Dalton & Michael

    The core secret to startup success isn't fundraising or growth hacking - it's solving your customer's biggest problems. But most founders are afraid to really understand those problems. What if that…

    2024-11-16
  15. Secrets You Can Learn From Your Customers
    Dalton & Michael

    YC partners Michael Seibel and Dalton Caldwell discuss how spending real time with your users can unlock insights and growth. Hear the stories of how Airbnb and Brex built billion-dollar companies by…

    2024-11-16
  16. The Student's Guide To Becoming A Successful Startup Founder
    Dalton & Michael

    If you're a high school or college student with big dreams of starting your own company, this video is for you. Dalton Caldwell and Michael Seibel, two startup founders who started in the early 20s…

    2024-11-16
  17. How To Earn Customers For Life
    Dalton & Michael

    In this first in-person episode, Michael Seibel and Dalton Caldwell reveal how startups can gain a competitive advantage by doing something deceptively simple. They share compelling stories of…

    2024-11-16
  18. The Hard Conversations Founders Don't Want to Have
    Dalton & Michael

    Michael Seibel and Dalton Caldwell discuss the importance of having honest and difficult conversations with startup founders. While having hard conversations can be uncomfortable, Seibel and Caldwell…

    2024-11-16
  19. The Cult of Conformity in Silicon Valley
    Dalton & Michael

    What happens when the unconventional becomes conventional? Michael Seibel and Dalton Caldwell discuss how the startup world has changed from being dominated by outsiders and nonconformists to now…

    2024-11-16
  20. The Secrets To Setting Smarter Goals
    Dalton & Michael

    If you're looking to maximize your startup's potential, start by setting the right goals. Michael Seibel and Dalton Caldwell provide tips and strategies for setting goals that will help keep you and…

    2024-11-16
  21. Avoid These Tempting Startup Ideas
    Dalton & Michael

    Thinking of a new startup idea? Dalton Caldwell and Michael Seibel discuss the types of ideas to stay away from—what we commonly refer to as "tarpit ideas."

    2024-11-16
  22. The Two Mindsets That Can KILL Your Startup
    Dalton & Michael

    Dalton Caldwell and Michael Seibel discuss the qualities that make a founder overly optimistic or far too pessimistic about their startup. Where is the right middle ground?

    2024-11-16
  23. Most Important Lifestyle Habits Of Successful Founders
    Dalton & Michael

    Dalton Caldwell and Michael Seibel discuss the best approaches to developing a healthy lifestyle that ultimately helps you run and grow a successful startup. Take care of yourselves out there.

    2024-11-16
  24. How Future Billionaires Get Sh*t Done
    Dalton & Michael

    Dalton Caldwell and Michael Seibel take a look at Paul Graham's essay "Maker's Schedule, Manager's Schedule" and share tips on how to be more effective and productive on the journey to creating a…

    2024-11-16
  25. What Basic Game Theory Teaches Us About Startups
    Dalton & Michael

    Dalton Caldwell and Michael Seibel discuss the problems with zero sum games within tech culture. Is your startup making a positive impact on the world or are your business practices a net negative in…

    2024-09-13
  26. Save Your Startup During an Economic Downturn
    Dalton & Michael

    Dalton Caldwell and Michael Seibel discuss Paul Graham's essay "Default Alive or Default Dead." They share strategies to cut your company's burn rate and keep your startup alive to see another day.…

    2024-09-13
  27. How To Deal With Setbacks
    Dalton & Michael

    Dalton Caldwell and Michael Seibel discuss the best approaches to managing the many setbacks startup founders can face over the lifetime of starting and running a business. Apply to Y Combinator:…

    2024-09-04
  28. Why You Should Leave Your FAANG Job
    Dalton & Michael

    Dalton Caldwell and Michael Seibel discuss the struggles of working at FAANG (Facebook, Apple, Amazon, Netflix, Google) and how to strategize leaving a big tech job to become a founder at a startup.…

    2024-09-04
  29. Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director)
    Lenny's Podcast: Product | Career | Growth

    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…

    2024-04-18
  30. Stop Innovating (On The Wrong Things) | Dalton & Michael Podcast
    Y Combinator Startup Podcast

    Startups need to innovate to succeed. But not all innovation is made equal and reinventing some common best practices could actually hinder your company. In this episode, Dalton Caldwell and Michael…

    2024-03-15
  31. Should Your Startup Bootstrap or Raise Venture Capital? | Dalton & Michael Podcast
    Y Combinator Startup Podcast

    Within the world of startups, you'll find lots of discourse online about the experiences of founders bootstrapping their startups versus the founders who have raised venture capital to fund their…

    2024-02-13
  32. Should You Be Optimistic About The Future of Technology? | Dalton & Michael Podcast
    Y Combinator Startup Podcast

    Social media often promotes a doom and gloom outlook about our future society. But is that worldview accurate? In this episode, Dalton Caldwell and Michael Seibel discuss the best ways for founders…

    2024-01-01
  33. Should You Quit Your Job At A Unicorn? | Dalton & Michael Podcast
    Y Combinator Startup Podcast

    If you’re an employee of a late stage company right now, how would you know when it’s time to move on vs. time to double down? The fact is there isn't an easy answer — it can really vary from person…

    2023-11-06
  34. Does Your Startup Need To Be In San Francisco?
    Y Combinator Startup Podcast

    Should you and your startup live in San Francisco? Y Combinator Partners, Michael Seibel and Dalton Caldwell, debate their different opinions on whether startups are more likely to succeed in the…

    2023-08-29
  35. Will OpenAI Kill All Startups?
    Y Combinator Startup Podcast

    How will the rise of AI impact startups and entrepreneurs? Join Michael Seibel and Dalton Caldwell for a discussion on the opportunities and challenges AI brings for founders. Apply to Y Combinator:…

    2023-07-24
  36. The Student's Guide To Becoming A Successful Startup Founder
    Y Combinator Startup Podcast

    If you're a high school or college student with big dreams of starting your own company, this video is for you. Dalton Caldwell and Michael Seibel, two startup founders who started in the early 20s…

    2023-04-25
  37. How To Earn Customers For Life
    Y Combinator Startup Podcast

    In this first in-person episode, Michael Seibel and Dalton Caldwell reveal how startups can gain a competitive advantage by doing something deceptively simple. They share compelling stories of…

    2023-03-14
  38. The Hard Conversations Founders Don't Want to Have
    Y Combinator Startup Podcast

    Y Combinator group partners Michael Seibel and Dalton Caldwell discuss the importance of having honest and difficult conversations with startup founders. While having hard conversations can be…

    2023-03-01
  39. The Cult of Conformity in Silicon Valley
    Y Combinator Startup Podcast

    What happens when the unconventional becomes conventional? Michael Seibel and Dalton Caldwell discuss how the startup world has changed from being dominated by outsiders and nonconformists to now…

    2023-02-10
  40. The Secrets To Setting Smarter Goals
    Y Combinator Startup Podcast

    If you're looking to maximize your startup's potential, start by setting the right goals. Michael Seibel and Dalton Caldwell provide tips and strategies for setting goals that will help keep you and…

    2023-01-16
  41. Avoid These Tempting Startup Ideas
    Y Combinator Startup Podcast

    Thinking of a new startup idea? Dalton Caldwell and Michael Seibel discuss the types of ideas to stay away from—what we commonly refer to as "tarpit ideas." Apply to Y Combinator:…

    2022-12-01
  42. The Truth About Y Combinator
    Y Combinator Startup Podcast

    With the YC S22 batch coming to a close, Dalton Caldwell and Michael Seibel reflect on the recent batch and their experience fundraising. The two group partners also clear up some misconceptions…

    2022-11-29
  43. The Two Mindsets That Can Kill Your Startup
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel discuss the qualities that make a founder overly optimistic or far too pessimistic about their startup. Where is the right middle ground? Apply to Y Combinator :…

    2022-11-24
  44. What Basic Game Theory Teaches Us About Startups
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel discuss the problems with zero sum games within tech culture. Is your startup making a positive impact on the world or are your business practices a net negative in…

    2022-11-17
  45. Most Important Lifestyle Habits Of Successful Founders
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel discuss the best approaches to developing a healthy lifestyle that ultimately helps you run and grow a successful startup. Funders, take care of yourselves out…

    2022-11-10
  46. Elon Musk & The Midwit Meme
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel on the midwit meme, how it applies to startups, and the best example: Elon Musk. Apply to Y Combinator: https://www.ycombinator.com/apply/

    2022-11-03
  47. Things That Don't Scale, The Software Edition
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel on software hacks that don't scale. Companies discussed include Google, Facebook, Twitch, and imeem. Watch the first video on doing things that don't scale here:…

    2022-10-27
  48. Why Investors (including YC) Can’t Fix Your Company
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel on common pitfalls in the advice from different types of investors and why you, the founder, are ultimately responsible for the success of your company. Apply to Y…

    2022-10-20
  49. What Does It REALLY Mean To Do Things That Don't Scale?
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel talk about Paul Graham's essay "Do Things That Don't Scale" and what it really means for founders. Read the essay here: http://paulgraham.com/ds.html Apply to Y…

    2022-10-13
  50. How To Change The World? Get The Small Things Right
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel talk about the importance of understanding incentives and doing research when it comes to building a world-changing startup. To create Rookies Mistakes we asked YC…

    2022-10-06
  51. Simple Products That Became Big Companies
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel talk about OpenSea, Gusto, and the importance of building simple products that solve a real problem. To create Rookies Mistakes we asked YC founders: Is there a…

    2022-09-29
  52. Where Do Great Startup Ideas Come From?
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel talk about where the ideas for Airbnb, Coinbase, and Stripe came from. Then they discuss what you can learn from these founders. To create Rookies Mistakes we asked…

    2022-09-12
  53. Successful Founders Are OK With Rejection
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel on the importance of talking to your users, why successful founders are ok with rejection from potential customers, and how protecting your ego by not talking to…

    2022-09-05
  54. Should You Follow Your Passion?
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel talk about solutions in search of a problem, whether or not to follow your passion, how to figure out what to work on, and how to motivate yourself. To create…

    2022-08-29
  55. Understanding Investor Terms & Incentives
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel talk about investor terms and incentives. To create Rookies Mistakes we asked YC founders: Is there a simple fact you wish you knew when you started your company or…

    2022-08-25
  56. YC Founders Made These Fundraising Mistakes
    Y Combinator Startup Podcast

    Michael Seibel and Dalton Caldwell are back for episode 2 of Rookie Mistakes to discuss common mistakes founders make when fundraising, and how to avoid them. Apply to Y Combinator:…

    2022-08-18
  57. Co-Founder Mistakes That Kill Companies & How To Avoid Them
    Y Combinator Startup Podcast

    In the first episode of Rookie Mistakes, Dalton Caldwell and Michael Seibel discuss co-founder mistakes. To create Rookies Mistakes we asked YC founders: Is there a simple fact you wish you knew when…

    2022-08-09
  58. Dealing With Setbacks And The Startup Gut Punch
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel discuss the best approaches to managing the many setbacks startup founders can face over the lifetime of starting and running a business. Apply to Y Combinator:…

    2022-07-27
  59. Saving Your Startup During an Economic Downturn
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel discuss Paul Graham's essay "Default Alive or Default Dead." They share strategies to cut your company's burn rate and keep your startup alive to see another day.…

    2022-07-21
  60. Why You Should Leave Your FAANG Job
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel discuss the struggles of working at FAANG (Facebook, Apple, Amazon, Netflix, Google) and how to strategize leaving a big tech job to become a founder at a startup.…

    2022-06-22
  61. How Future Billionaires Get Sh*t Done
    Y Combinator Startup Podcast

    Dalton Caldwell and Michael Seibel take a look at Paul Graham's essay "Maker's Schedule, Manager's Schedule" and share tips on how to be more effective and productive on the journey to creating a…

    2022-06-22
  62. 運転資金が残り1年以下になったときの対処法
    FoundX Reviewスタートアップ IdeaCastMentioned

    残り1年以下の資金になったときにはどうすればよいでしょうか。 今回の Tip の元記事は Dalton Caldwell の『 運転資金が1年分以下になった会社へのアドバイス 』です。

    2021-10-21
  63. Y Combinator's Michael Seibel & Dalton Caldwell - Lessons from 5000 Entrepreneurs
    Wharton FinTech Podcast

    Miguel Armaza is joined by Michael Seibel and Dalton Caldwell, Managing Directors and Group Partners at Y Combinator (YC). YC is one of the most successful startup accelerators and venture capital…

    2021-02-22
  64. #147 - Startup School Week 6 Recap - Tim Brady on Culture and Dalton Caldwell on Pivoting
    Y Combinator Startup Podcast

    We've cut down the sixth week of lectures to be even shorter and combined them into one podcast.First a lecture from Tim Brady. Tim’s a partner at YC. His lecture covers the importance of building a…

    2019-10-09
  65. #112 - Ryan Hoover and Dalton Caldwell
    Y Combinator Startup Podcast

    Ryan Hoover is the founder of Product Hunt which was in the Summer 2014 YC batch and was acquired by AngelList. He also invests in startups through his Weekend Fund.Dalton Caldwell is a Partner at YC…

    2019-02-15
  66. #15 - IPFS, CoinList, and the Filecoin ICO - Juan Benet and Dalton Caldwell
    Y Combinator Startup Podcast

    Juan Benet is the founder of Protocol Labs (YC S14). They're working on IPFS, Filecoin, and Coinlist. Dalton Caldwell is a Partner at YC.

    2017-06-30
  67. "Mistakes Were Made," a panel about failure (Code Conference 2016)
    Recode Replay

    Former General Magic executive Joanna Hoffman, former Aereo CEO Chet Kanojia and Y Combinator partner Dalton Caldwell talk with Recode's Peter Kafka about thier past entrepreneurial efforts that…

    2016-06-02
  68. Dalton Caldwell / App.net - Part 2
    Founders Talk: Startups, CEOs, Leadership

    Adam talks with Dalton Caldwell the Founder of App.net. Since we barely scratched the surface of the planned conversation around what he's doing with App.net in part 1, Dalton agreed to come back on…

    2013-06-07
  69. Dalton Caldwell / App.net - Part 2 (Founders Talk #45)
    Changelog Master Feed

    Adam talks with Dalton Caldwell the Founder of App.net. Since we barely scratched the surface of the planned conversation around what he's doing with App.net in part 1, Dalton agreed to come back on…

    2013-06-07
  70. After Founders Talk #42
    Founders Talk: Startups, CEOs, Leadership

    Adam Stacoviak talks with Dalton Caldwell the Founder of App.net after Founders Talk #42.

    2013-05-16
  71. After Founders Talk #42 (Founders Talk)
    Changelog Master Feed

    Adam Stacoviak talks with Dalton Caldwell the Founder of App.net after Founders Talk #42.

    2013-05-16
  72. Dalton Caldwell / App.net - Part 1
    Founders Talk: Startups, CEOs, Leadership

    Adam talks with Dalton Caldwell the Founder of App.net. This is a hefty part 1, mainly focusing on the road traveled by Dalton to get to App.net. We barely scratched the surface of the planned…

    2013-05-16
  73. Dalton Caldwell / App.net - Part 1 (Founders Talk #42)
    Changelog Master Feed

    Adam talks with Dalton Caldwell the Founder of App.net. This is a hefty part 1, mainly focusing on the road traveled by Dalton to get to App.net. We barely scratched the surface of the planned…

    2013-05-16
  74. Episode 84: Dalton Caldwell
    The Big Web Show

    Dalton Caldwell, CEO and co-founder of App.net, is Jeffrey Zeldman's guest in Episode No. 84 of The Big Web Show, sponsored by Happy Cog™.

    2013-03-07
  75. No-Host Bar Dot Net with Dalton Caldwell
    The New Disruptors

    Dalton Caldwell is the head of App.net (sometimes called ADN for App Dot Net), which some think is a Twitter competitor, but it isn't quite. It seems to be a typical venture-backed startup firm, but…

    2013-03-06
  76. Free Accounts and Developer Incentives, with Dalton Caldwell and Bill Kunz
    CMD Space

    This week Myke talks to Dalton Caldwell about some of the recent changes to App.net, including the new free accounts and the Developer Incentive Program. He is then joined by Bill Kunz to discuss his…

    2013-02-27
  77. Now The Hard Work Begins, with Dalton Caldwell
    CMD Space

    This week Myke is joined by Dalton Caldwell, CEO and Founder of App.net. They discuss the experience of launching this service, how it has evolved and what the future has in store for App.net.

    2012-11-07
  78. Dalton Caldwell
    App.net Live

    Frank and Dalton discuss hitting app.net's funding goal, the future of the platform, what's on the horizon for third-party developers, and Dalton's favorite coffee.

    2012-09-07
  79. Episode 77: 77: Nucleation Site
    HypercriticalMentioned

    John Siracusa and Dan Benjamin talk more about a potential smaller iPad, OUYA's challenges, what makes a successful Kickstarter project, how the Penny Arcade Kickstarter could have been more…

    2012-07-20