Chasing that next BIG thing (Interview)

The Changelog: Software Development, Open Source

Drew Wilson is back! It’s been more than a decade since Adam and Drew have spoken and wow, Drew has been busy. He built Plasso and got acquired by GoDaddy. He built a bank called Letter which didn’t work out…and now he’s Head of Design at Clerk and back to chasing that next big thing.

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Sponsors:

• Heroku – The Next Generation of Heroku “Fir” is coming soon — Fir is built on a foundation of cloud native technologies and open source standards, ensuring portability, interoperability, and a vibrant ecosystem for your applications. Cloud Native for everyone, for the next decade and beyond.
• Depot – 10x faster builds? Yes please. Build faster. Waste less time. Accelerate Docker image builds, and GitHub Actions workflows. Easily integrate with your existing CI provider and dev workflows to save hours of build time.

Featuring:

• Drew Wilson – Website, GitHub, LinkedIn, X
• Adam Stacoviak – Website, GitHub, LinkedIn, Mastodon, X

Show Notes:

• DrewWilson.com
• Clerk
• Founders Talk #19 + Founders Talk #20

Something missing or broken? PRs welcome!

Capitoli

1. This week on The Changelog (00:00:00)

2. Sponsor: Heroku (00:01:07)

https://www.heroku.com/changelogpodcast

3. Start the show! (00:04:50)

4. Drew has a working Macintosh Portable (00:09:36)

5. Drew's uncanny ablity of knowing what will trend (00:14:36)

6. Hard beliefs (00:16:31)

7. Sponsor: Depot (00:23:02)

https://depot.dev

8. This is a podcast (00:25:11)

9. How are you SO GOOD? (00:29:08)

10. Learning about banking to build a bank (00:32:51)

11. Why build a bank? (00:37:11)

12. The YC pitch! (00:45:10)

13. Why did it fail? (00:49:37)

14. Are you loaded now? (00:57:30)

15. Being a part of a BIG idea (01:04:35)

16. On needing a job rn (01:14:36)

17. Bringing back Valio Con (01:18:04)

18. Drew's next big thing? (01:26:47)

19. Good catching up (01:35:26)

20. "What the crap?" is a Drew thing (01:36:30)

21. Closing thoughts and stuff (01:38:00)