Chasing that next BIG thing with Drew Wilson (Changelog Interviews #639)
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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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100 minutes
Recorded Apr 23, 2025
Published May 1, 2025
Download (144MB)
Transcript
Startups
Culture
Drew Wilson – Website, GitHub, LinkedIn, X
Adam Stacoviak – Website, GitHub, LinkedIn, Mastodon, X
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.
DrewWilson.com
Clerk
Founders Talk #19 + Founders Talk #20
Chapter Number<br>Chapter Start Time<br>Chapter Title<br>Chapter Duration
00:00
This week on The Changelog
01:07
01:07
Sponsor: Heroku
03:42
04:50
Start the show!
04:47
09:36
Drew has a working Macintosh Portable
05:00
14:36
Drew's uncanny ablity of knowing what will trend
01:55
16:31
Hard beliefs
06:30
23:02
Sponsor: Depot
02:09
25:11
This is a podcast
03:57
29:08
How are you SO GOOD?
03:43
10
32:51
Learning about banking to build a bank
04:21
11
37:11
Why build a bank?
07:58
12
45:10
The YC pitch!
04:28
13
49:37
Why did it fail?
07:53
14
57:30
Are you loaded now?
07:05
15
1:04:35
Being a part of a BIG idea
10:01
16
1:14:36
On needing a job rn
03:28
17
1:18:04
Bringing back Valio Con
08:43
18
1:26:47
Drew's next big thing?
08:40
19
1:35:26
Good catching up
01:04
20
1:36:30
"What the crap?" is a Drew thing
01:29
21
1:38:00
Closing thoughts and stuff
01:38
Changelog
Play the audio to listen along while you enjoy the transcript. 🎧
Adam Stacoviak
Well, Drew Wilson is back in the house… It’s been a while since you’ve been here.
Drew Wilson
It has.
Adam Stacoviak
I want to say – gosh, I didn’t even do my math here. Let me go search quickly, Drew Wilson…
Drew Wilson
I think maybe 15 years, 12 years… I don’t know, something like that.
Adam Stacoviak
Okay, so we had you on Founders Talk a couple of times. Founders Talk was a show that I did solo, where I talked to founders, makers, builders, things like that… And it was Valio. Remember this name, Valio?
Drew Wilson
Yeah. ValioCon, man.
Adam Stacoviak
And part one and part two, for whatever reason. That was the name of the show. It was Drew Wilson / Valio - Part 1 and Valio - Part two.
Drew Wilson
Oh, wow. Maybe we’re talking pre-ValioCon, and we’re talking back when I was making stuff under the name Valio, which would have been like 2009 or something.
Adam Stacoviak
You know, I don’t know. ValioCon was mentioned… You were at [unintelligible 00:06:15.07]
Drew Wilson
Oh, dang. So that’s probably like 2011.
Adam Stacoviak
That’s 2011, man. Yeah, that’s right. Exactly. 2011. Pegged it. September 2011.
Drew Wilson
Wow.
Adam Stacoviak
Okay, so that was that show. That was Founders Talk. I think we had you on this show too at some point, but I don’t know when.
Drew Wilson
Yeah, I’ve been on here before, and I think – it was a while ago. It was a couple years after that one, for sure. So maybe 2014 or 2013, something like that.
Adam Stacoviak
Well, listen, I should have did my better research on when Drew was last on this podcast. It was ages ago. It was basically the beginning, it was basically the earliest of days… And it’s been a lifetime. I think I literally haven’t talked to you in a decade.
Drew Wilson
It has been a while, man.
Adam Stacoviak
At least a decade. I would say at least a decade.
Drew Wilson
I think maybe one or two tweets, or something like that…
Adam Stacoviak
Yeah, here and there. Nothing special. You got busy, though.
Drew Wilson
Yeah, I got busy.
Adam Stacoviak
You’ve always been the busiest person I know of, but you got really busy.
Drew Wilson
Yeah, yeah.
Adam Stacoviak
Like, you built a company and sold it busy.
Drew Wilson
Yeah, yeah. That was fun.
Adam Stacoviak
How does that feel?
Drew Wilson
It was – dude, it was incredible. It’s like one of those – I mean, it’s not to the scale of “You’re a billionaire now. You never have to work again.” But it was one of those, like, you come up with an idea, you build it yourself, you’re able to build a little company around it, you raise some money,...