Why Founders Need “Scalers” on Their Early Teams
episode
Startup Success: A Podcast for Founders & Investors
28 min
1 speaker
8 chapters
transcribed 16 days ago
Transcript
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What early‑stage founders need to know about hiring “horizontal generalists” (scalers)?
Welcome to Startup Success, the podcast for startup founders and investors. Here you'll find stories of success from others in the trenches as they work to scale some of the fastest growing startups in the world. Stories that will help you in your own journey. Startup Success starts now.
Welcome to Startup Success. In this episode, I sit down with Casey Wu, who is the founder and general partner of Fog Ventures and the founder and CEO of Operators Guild. After helping to scale companies like WeWork and The Landing through hypergrowth, Casey now sits at the intersection of operators and investors backing the next generation of startups. We dive into the rise of the horizontal generalist, how AI is reshaping, how teams are built and scaled, and what it takes to operate in today's startup environment. Casey also shares how Operators Guild is redefining modern operators and how Vogue Ventures is investing in what he calls Toolbox 2.0 for the next wave of. Builders. Thanks so much, Casey, for being here.
I'm
happy to be here.
Yeah. So, you know, you have such an interesting background. I wanna start there first. If you wouldn't mind kind of walking us through it a bit and then getting into what led you to found both Fog Ventures and the Operator's Guild.
My path is one that is kind of the classic, went to college, then was told that there's these really nice careers after college that you should pick from. You know, management consulting, corporate job, doctor, lawyer. And there's one called Wall Street. And you're like, Oh, I was an econ major, so I did that. I went to an island called Manhattan, got an investment banking job, amazing. And then got a hedge fund job, which is kind of like the pinnacle for a private equity job. And I was twenty four, overpaid, it was great. I had this nice office. I remember this Central Park View. And I said, I made it.
Yes.
I just need to keep doing this and keep my job and retire in ten years. And I made it about eight years. And Realised I wasn't happy.
Oh.
And I didn't know why. Long story short, I left Wall Street, joined a ten person tech startup in New York, Silicon Alley.
Okay. That's a big change.
Yeah. Huge change. Very
scary.
When when when All your professional life is chasing Wall Street and then you leave.
Mm-hmm.
You got in. And so I learned that I loved it.
Oh good.
And I I kinda joke, why do I like eating glass? I loved it so much that I realized I had to go probably move cities if I was gonna do this as a career. This is two thousand ten.
Mm-hmm.
And I went to a place called Silicon Valley. Mm-hmm. I was the recovering Wall Street guy.
Ah.
Trying to go into a tech startup.
Okay. And
I went into a little company called Stripe for an interview. I had about they had about 60 people at the time. And I was very excited. They looked at my resume and said, Do you code or do you sell? I was like, I uh I don't know if it's a trick question, but I do call finance, ops, clean toilets. I'm here to I'm here to know what a real tech company's like, you know, I'm from New York. And he said, uh you don't even have a CPA. So you don't qualify for finance stripe.
Oh, interesting.
And that was two thousand thirteen. Basically, back then and earlier, if you weren't coding or selling, you weren't product engineering or sales and marketing, you're nobody. You're you're you're you're like the second class citizen.
That's true.
You're called back office, you're called G and A.
Yes.
How did Casey Woo’s career path lead him to create Operators Guild and FOG Ventures?
And so I try to find a community because I was lonely. I changed jobs. I joined a CFO community, no offense. A lot of it was more heavy accounting. So it was just kind of one wasn't my my DNA. Uh I wasn't really a founder.
Mm-hmm.
You know, so you know, you know, but I was much more of an operator, operator, CFO COO. So I was invited to a nine person lunch in 2015. With people like me, these kind of misfits that left McKinsey or Goldman, or you know, we we weren't an engineer, we weren't a salesperson. And I said, Hey, you're my people. Do you want to just meet every month and help each other? Uh that started Operators Guild.
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Chapters
8 chapters
1
What early‑stage founders need to know about hiring “horizontal generalists” (scalers)?
0:01–3:51
2
How did Casey Woo’s career path lead him to create Operators Guild and FOG Ventures?
3:51–7:50
3
Why are scalers essential for hyper‑growth startups in today’s AI‑driven world?
7:50–10:27
4
What signals on a resume and in an interview reveal a true scaler?
10:27–14:12
5
How has the role of the CFO/COO evolved with AI and modern operating models?
14:12–17:49
6
What personality traits and DNA make someone a successful scaler?
17:49–20:52
7
How does Operators Guild support scalers through community, events, and funding?
20:52–24:17
8
What practical advice does Casey give founders for building and scaling early teams?
24:17–28:00
Speakers
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