Choosing contrarian, hard, durable ideas

Michael Grinich is the co-founder and CEO of WorkOS, the enterprise authentication and identity infrastructure used by Anthropic, OpenAI, Cursor, xAI, and hundreds of fast-growing companies. Before WorkOS, Michael dropped out of MIT, worked at Dropbox, and founded Nihilus — where a painful first experience with enterprise features planted the seed for everything that came next.

In this episode, Immad Akhund and Raj Suri sit down with Michael to talk about the SaaS apocalypse thesis, how WorkOS quietly became the enterprise layer for AI's biggest companies, and what it actually takes to build for developers.

What you'll learn:

1. Why the SaaS apocalypse narrative gets it completely backwards
2. How WorkOS became the default enterprise-ready layer for AI-native companies
3. The Stripe parallel: why developer infrastructure compounds the same way payments did
4. What a failed first startup taught Michael about idea validation
5. How keeping a daily idea notebook — volume, not quality — led to WorkOS
6. Why second-time founders approach conviction and validation completely differently
7. The do-or-die bond between developer tools and their customers
8. How Michael taught himself enterprise sales after starting as a purely technical founder
9. Why building for developers is the ultimate boss battle in tech
10. What AI getting to Renaissance-printing-press level actually means for software

Chapters:

(00:00) The SaaS apocalypse thesis — and why Michael thinks it's wrong

(01:09) Introducing Michael Grinich — MIT, Dropbox, and the road to WorkOS

(05:14) The Stripe origin story and early MIT startup network

(07:03) Drew Houston, Dropbox, and what convinced Michael to build

(09:05) Founding Nihilus: three maxed credit cards and two days from missing rent

(11:00) How to generate startup ideas: volume over quality, the notebook habit

(14:05) Finding sticky ideas — the ones you keep coming back to

(17:10) Why the energy behind an idea matters as much as the idea itself

(20:16) What experience gives you: pattern recognition and a framework for new scenarios

(24:05) The moment Michael saw the enterprise auth problem and knew it was real

(27:02) How Anthropic, OpenAI, and Cursor ended up as WorkOS customers

(31:16) Why WorkOS sits at the security and growth layer for AI companies

(35:06) The ultimate boss battle: building developer tools for other developers

(39:06) Why developer customers give the best product feedback — and why that's a gift

(44:04) The SaaS apocalypse revisited — and what's actually happening to software

(47:17) How AI compressed the timeline to enterprise-ready from months to a day

(53:03) Tying company value to something durable through technology waves