When Should Your Startup Go Multi-Product?

Dalton and Michael discuss when founders should think about building a second product. Discussion includes: the reasons to build (or not build) a second product, building toward a suite, Slack vs Notion, how long to stay a one product company, why Microsoft and Google waited in the early days, how to avoid stacking low performing products, why PostHog built multi-product quickly, Zoom not being able to build a suite, why any products in the office suite means that you are ultimately competing with Microsoft, Google launching very different additional products, should you pivot instead of saying that you are doing a second product, and more. – 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. Learn more at StandardDB.com

Michael SeibelhostDalton Caldwellhost

Sep 21, 20269mWatch on YouTube ↗

EPISODE INFO

Released: September 21, 2026
Duration: 9m
Channel: Dalton + Michael
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

Dalton and Michael discuss when founders should think about building a second product. Discussion includes: the reasons to build (or not build) a second product, building toward a suite, Slack vs Notion, how long to stay a one product company, why Microsoft and Google waited in the early days, how to avoid stacking low performing products, why PostHog built multi-product quickly, Zoom not being able to build a suite, why any products in the office suite means that you are ultimately competing with Microsoft, Google launching very different additional products, should you pivot instead of saying that you are doing a second product, and more. – 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. Learn more at StandardDB.com

SPEAKERS

Michael Seibel
host
Startup founder and investor; co-founder of Justin.tv/Twitch and former YC partner.
Dalton Caldwell
host
Startup founder and investor; known for founding App.net and work with Y Combinator.

EPISODE SUMMARY

In this episode of Dalton + Michael, featuring Michael Seibel and Dalton Caldwell, When Should Your Startup Go Multi-Product? explores go multi-product only after a winning wedge, not as cover. They argue the decision to go multi-product depends heavily on whether the first product is failing (pivot) or succeeding (adjacent expansion).

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