Dalton + MichaelWant to Build a Great Startup? Start Having Fun.
Episode Details
EPISODE INFO
- Released
- October 12, 2026
- Duration
- 17m
- Channel
- Dalton + Michael
- Watch on YouTube
- ▶ Open ↗
EPISODE DESCRIPTION
The best startup founders have a secret advantage: they have fun. Dalton and Michael discuss how you can embrace "Type 2 Fun" and enjoy the adventure. It's not just a mindset, it's a requirement to build an enduring company. Discussion includes: the difference between type one and type two fun, why type two fun is more rewarding than “empty calorie” fun, how reframing hard days as fun unlocks endurance, why people fondly remember their hardest startup moments, how to tell if you’re a replaceable employee, why learning to love being uncomfortable is how you stretch yourself, how to transfer grit from sports or academics to your startup, why a competitor who is having a great time is the hardest to beat, why you shouldn’t wait for the torture to end, why people suited to be founders are under-stimulated by normal work, the personal inventory founders should take (rent, safety, sleep, food, exercise) before pushing hard, why liking your users, your problem and your teammates helps, and why the startup journey is an adventure worth enjoying. 0:00 Introduction to type two fun 1:53 Learning to enjoy hard things 4:34 The mindset shift in startups 5:41 Learning to love being uncomfortable 6:53 Transferring grit from life to startups 8:38 The competitive edge of type two fun 11:01 Flipping the mindset switch 12:10 Seeking challenge vs. seeking comfort 13:08 Maintaining a healthy foundation 14:31 Viewing the startup journey as an adventure 15:54 The unfair advantage of great founders _ Dalton + Michael is brought to you by @Standard_Cap. Standard Capital is the AI-native Series A fund. Learn more at standardcap.com – About Dalton: Dalton Caldwell is Co-Founder and Partner of Standard Capital. He spent 12 years at Y Combinator, where he served as Managing Partner, worked across 25 YC batches, and advised more than 1,000 startups. His investments include Whatnot, Brex, GitLab, PostHog, Stock Space, Rappi, Razorpay, and Oklo. Before becoming an investor, Dalton founded imeem and App.net. About Michael: Michael Seibel is a Partner Emeritus at Y Combinator, where he served as Managing Partner of the early stage accelerator from 2014 - 2024. Michael also serves on the board of three companies: Reddit, Dropbox, and Kalshi. He moved to the bay area in 2006, and was a co-founder and CEO of two Y Combinator startups Justin.tv/Twitch (2007 - 2011) and Socialcam (2011 - 2012). In 2012 Socialcam sold to Autodesk Inc. for $60m and in 2014, under the leadership of Emmett Shear (CEO) and Kevin Lin (COO) Twitch sold to Amazon for $970m. – Are you an AI builder? Check out StandardDB. Discover offers, credits, tools, and partner programs from the StandardDB ecosystem.
SPEAKERS
Michael Seibel
hostYC partner and former CEO of Y Combinator; cofounder of Justin.tv/Twitch.
Dalton Caldwell
hostYC partner and startup founder (App.net), focused on early-stage company building and product.
EPISODE SUMMARY
In this episode of Dalton + Michael, featuring Michael Seibel and Dalton Caldwell, Want to Build a Great Startup? Start Having Fun. explores great founders win by enjoying the hard parts of startups Dalton Caldwell and Michael Seibel define “type two fun” as work that feels difficult in the moment but becomes rewarding and even joyful in retrospect, and they argue startups are best approached this way.
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