Stream: interviews

Topic: 639: Chasing that next BIG thing


view this post on Zulip Logbot (May 01 2025 at 22:14):

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. :link: https://changelog.fm/639

Ch Start Title Runs
01 00:00 This week on The Changelog 01:07
02 01:07 Sponsor: Heroku 02:44
03 03:51 Start the show! 04:47
04 08:38 Drew has a working Macintosh Portable 05:00
05 13:38 Drew's uncanny ablity of knowing what will trend 01:55
06 15:32 Hard beliefs 06:30
07 22:03 Sponsor: Depot 02:09
08 24:12 This is a podcast 03:57
09 28:09 How are you SO GOOD? 03:43
10 31:52 Learning about banking to build a bank 04:21
11 36:13 Why build a bank? 07:58
12 44:11 The YC pitch! 04:28
13 48:39 Why did it fail? 07:53
14 56:31 Are you loaded now? 07:05
15 1:03:37 Being a part of a BIG idea 10:01
16 1:13:37 On needing a job rn 03:28
17 1:17:05 Bringing back Valio Con 08:43
18 1:25:48 Drew's next big thing? 08:40
19 1:34:28 Good catching up 01:04
20 1:35:32 "What the crap?" is a Drew thing 01:29
21 1:37:01 Closing thoughts and stuff 01:38

view this post on Zulip Matthew Sanabria (May 03 2025 at 16:21):

In the Hard Beliefs section the guest mentions that product managers without design, sales, or engineering experience are useless. I totally agree

They then go on to rhetorically ask why CEOs let this happen (hire product managers like this). Simple answer! Most CEOs themselves are that way! They don't have the experience and they suck too!

view this post on Zulip Ron Waldon-Howe (May 04 2025 at 03:16):

Maybe "founder mode" should be executives becoming more discerning when they hire managers and product managers :)

view this post on Zulip Andrew O'Brien (May 12 2025 at 23:33):

Man, this reminds me how much fun it was to be in fintech in 2023Q1.

[Narrator: it was not]

view this post on Zulip Tim Uckun (May 14 2025 at 04:55):

product managers are there to take the blame when things go bad. That's the only skill they need really. The ability to be blamed and then fired.


Last updated: Jun 28 2025 at 13:42 UTC