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Casey
Foreign.
Sponsor Representative
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Interviewer
Casey, welcome to the liftoff.
Casey
How are you?
Interviewer
You're sort of the perfect. Yeah, you're sort of the perfect person to have on the liftoff because we talk about growth, we talk about scaling. You've got a new book out all about scaling. You've done it for a number of companies before. You're, you're an operator, you're an executive, you're a mentor, and now you're an author.
Casey
How are you?
Interviewer
You're sort of the, you've got all the proper background. You also, as I understand, a West Point cadet and a Harvard graduate as well.
Casey
Yeah, I work a lot. I just keep myself busy a lot.
Interviewer
Let's, let's start. I know you have this new book called the Scaler. Right. So let's talk about, just set a, set a baseline here. What is scaling your definition?
Casey
Scaling to me is the art of creating leverage in a business. In the business context, leverage could be productivity, efficiency, you know, kind of the more classic terms. It can come through systems, people strategizing. So like not doing something is also leverage. So that in general scaling. And I think another unique thing about scaling is in my world, scaling is horizontal. It's cross departmental, it's, it's left, right, rather than up, down. Because I think scaling a business has to be all the parts. Now you can also scale the legal department, right? So that's all only the things within the legal department. But in general, I think of scaling as the whole organism and that organism in the business context is the company.
Interviewer
How do I, how do I differentiate between a scalar and a regular operator then?
Casey
To me, an operator can be a much wider, wider range of general employee or worker. A scalar specifically, I think masters and owns across two dimensions or more.
Interviewer
And.
Casey
It'S kind of a, have you seen mixed martial arts mma? Yeah, it's the person who knows how to strike and wrestle or, you know, wrestle and do karate or, you know, something that it is, you know, with, with a level of mastery for Both or more. It's that combined element. And obviously the assumption is that they're good at it. They do provide leverage. Not just I want to do two things, but they efficiently fuse two or more disciplines and functions to provide leverage for the business.
Interviewer
So people that can play multiple positions, wear many hats. That kind of metaphor.
Casey
Yeah, I know this sounds weird, but like, I'm a five time cfo, but I'm not a cfo. I'm not a. Fine, I get what you mean though.
Sponsor Representative
Yeah.
Casey
Specialist. I am what I like to believe is a scaler who has a finance discipline. Oh, here's an analogy. Sorry. That's kind of how I think Special Forces, Navy seals in general. I think Navy seals are built for more. They're like, kind of like generalists, right? Swim, fight, eat, kill. Because they have to attach to very different missions and be very, very adaptable. Okay, but how do you become adaptable? You need to know a little bit about everything. Land warfare, aerial warfare, how planes work, you know, how to shoot a weapon, how to save someone. It's. To do that job, you actually need multiple understandings. And so I like to say, you know, so in the Navy SEAL squad, there are like, I think specialists like sniper medicine, radio comms. Right. There are people that, they all have gone through SEAL school, but some of them go through like radio comms or they're really good at something. But so what I like to say is you don't really ever call an. A Navy SEAL who's a medic a doctor. You don't call them doc. At least you know, he's a Navy seal first.
Interviewer
Casey, let's.
Casey
That's where the specialist versus scaler happens.
Interviewer
Yeah. You have such amazing experience working with many well known companies that have been huge successes. Why don't we jump into an example or two of where you've seen a company leverage this scaling concept and really see the fruits of its labor bear out. Can you share an example? Oh, yeah.
Casey
I mean, the trickiest thing about a scaler is that we are silent. By silent, I mean not silent. But a good example of a scaler is, you know, there is the COO or CFO or biz ops who comes in, notices the scale of the growth of the company, and puts in, I'm gonna make it up. A new HR system or a new system to capture product information, customer information that ties into the financial system that combined provide very worthwhile business intelligence for the company. No one ever told them to do that. They came in and they're like, wait a Minute. If I don't do this, it's going to be a lot harder to get real time battlefield intelligence, so to speak or real time business intelligence. Because by that point the data is 2x, the customers are 2x and it takes time to build all these in to integrate classic implementation integration. So seeing around the corner, seeing ahead, paving the road ahead. If you're, if we're doing our job right, there's no bumps in the road. An opposite thing would be like you can see us when, when scalars may not be fully empowered or working is. I'll give you an example which is look, I wrote about it. We work. I was at WeWork. Amazing product, amazing sales teams.
Sponsor Representative
Right.
Casey
Amazing finance team. However, the scaling apparatus was not there fully. Right. So it went bankrupt in the end because you have to balance the cash, burn the collections. Right. Good old real estate. That's when scaling was not there. Because people think of a business going under as like bad product, bad sales. No, it could also be bad.
Interviewer
So it's really interesting you used WeWork as an example because that's massive scaling on one hand and on the other, oops, you know.
Casey
Yeah, because you have to scale all the parts in this case financials. And that's why I think to appropriately scale or a leader of a scaling organization needs to have more than one discipline. Like they understand product and finance or. Because if you marry the two together you would say, okay, we're growing too fast.
Interviewer
It occurs to me you need a certain culture too that empowers people in their positions where they have the, they have the knowledge. So in other words, you wanted to go implement a new system and it seems very pertinent relevant in today's AI world. Right. Where holy f. I can like, you know, see this AI tool and if I implement it, I'm going to be able to save time, get better data, report these, these, these findings a lot faster to a broader team, whatever the case may be. But if you don't have the right culture, you're like, okay, I gotta wait to use this until somebody asks me about it or, you know what I mean? Yeah.
Casey
It's also look, the benefit of having a really strong some scalers in a business is that if you have a culture that just, you know, is cooperative, that could work. Meaning I don't need everyone to be thinking systems. You need a couple people who make sure the system works and then tell everyone, hey, we're using a new system and this is the benefit of it. And they're like, oh great, you Know, because some people are busy selling, some people are busy building product. They're not thinking about scaling and that's the other way to think about it. Specialists, to me, they have a different job. If you're a product person, you're building a product. You're not worried about accounting or the payroll or fundraising. Right. If you're selling, you're worried about selling your finance, you're worried about making sure the cash is collected and things are paid and, but notice they don't have rooms to be thinking about much else. The job of a scaler is to think about the whole, the everything else. The, what I call the arteries, the, the, the nervous system, the cardiovascular system. That is a job unto itself.
Interviewer
Casey, in addition to this Operators Guild that you run, you're also in a fund, right? You're. I don't know if it's a active venture capital role for you or more of an investor, but you, you obviously you mentor a lot of, of success or hot potential startups. Yeah.
Casey
Oh, I would say less mentor, but. Oh, sorry. So you're talking about fog, the fund, not Operators Guild.
Interviewer
Right.
Casey
Operators Guild is the preeminent community for tech operators, specifically non technical and non go to market. So my joke is we don't code and we don't sell. So our titles are cfo, coo, CEO and director, and above.
Interviewer
Right.
Casey
Director of finance, Director of ops, biz ops, rev ops, Chief of staff. We are the horizontal, we are the multi disciplined. We're the scales, we're the glue.
Interviewer
I like that.
Casey
Okay, okay. Yep. So that's. We're like, we're like one minus if you think about it. We're one minus sales product. You know, things that are very defined. Got it. And that's a very important, like oil and engine or you know, glue as you call it, or as I call it. That is needed. Okay. And Fog Ventures is the, it's separate. It's the investing syndicator arm of the community. It's a separate application. Operators Guild members obviously get in automatically because of their qualification. And it is operators investing together in tools that we love. So the modern operating tool stack. And it's been wildly successful because if you think about it, we build these companies so we can appreciate what good looks like from a diligence standpoint. But more importantly, a lot of us use these products, so we're a decent gauge at if this product has legs or not.
Interviewer
Right, Right. And there's probably no, no lack of new stuff being foist upon you to see how you evaluate Those things.
Casey
That's right.
Interviewer
So what kind of things are you looking at today? What kind of application?
Casey
We specifically are infrastructure AI B2B tools for the Finance CFO office, which is becoming a performance office or business intelligence office. Anything that is, you know, project management, scaling related. So as you, AI is great for that. Right. AI is cross database, cross department handle, unstructured, you know, oil and vinegar and combine it.
Sponsor Representative
Right.
Casey
And that's once again what scalers do. We have to cross different departments. So AI is really unlocking a lot of our powers to scale better, to remove the walls between functions that cause misalignment, inefficiency, confusion, loss of time.
Interviewer
I don't know as much about the categories that you're focused on. I'm not so much the operator myself. Are roles going away? Are we seeing a consolidation into the. The COO CFO operating function? Are they hiring less people on the ARAP COO controller roles? What's happening in that whole world.
Casey
Right now? I think it's more, much higher, bar to hire a new person, a little bit less. So just, you know, laying everyone off. It is very much. Can we do more with less? Yeah, well, maybe in the past it was we would hire three people. Now it's one. Because AI. Sorry. Because right now what is really happening is increased productivity per person versus replacing a person. So right now, for sure there's higher productivity. People are saving time doing, you know, not summarizing things or, you know, AI drafting things or summarizing notes. But eventually, I think if productivity increases more and more and more and more. Yeah, I think all else equal what was needed for five people, two people can do. So I think we're still far away from a complete replacement. I still think, you know, far could be 10, 15, 20 years, but it's. It's definitely in the realm of, you know, putting on an Iron man suit. But you still need the human.
Interviewer
Yeah. Interesting, though I haven't thought about it in this way. Like, do I really need that head of hr? Does it have to be a senior executive? Do I really need the head of legal, head of finance, head of. You know what I mean? So maybe some of these do get consolidated because of the systems around you, right? Is that what you're intimating?
Casey
That's right.
Interviewer
And then let me ask you a question which is sort of related to that, which is I'm building a team. I got a hot startup idea, Casey. I got to get this thing out in the marketplace. I'm a technologist, I'm a cto type, right. Will call me a co founder. Also who's the next person that I typically need to hire? And I'll tell you, my bias is towards that person that has the Rolodex, the network that the sales know how to go bring in the revenue. I'm ready to take this thing out to the market. So I want to go hire that salesperson. Is that the right way to think about it or do I need the person who is going to just make sure the trains run on time and you know, we're properly managing our cash flow and you know what's the next hire after that cto?
Casey
It depends on the business. For example, Uber needs legal help earlier because they would have to file lawsuits. Low margin businesses like DoorDash or Amazon.com need more analytics and data engineers because it's way more important to get, you know, this mass data and optimization problem. So the first thing is just like what is the type of business and what is the main competency need? Then from there there's scalers, right? It's scalar to mirror a ratio. The beauty, the beautiful thing with scalers by definition we're leverage so you don't need to hire a ton of us. In terms of the ratio, every ratio is different. But a strategic CFO can be a finance scaler, right? They're highly analytical, they bring in the finance T shaped skill set and can really help scale things that touches money. There is external scaler so they're good at commercialization generally kind of cooish. So they're pretty good about external. So that's go to market scaling out the combined sales marketing team and product teams really thinking about growing customers and outward growth. Then there's internal ecosystem scalers that are very good. They generally sit in the finance legal people division. So for them they are always thinking about how to make the lives of the employees easier and more effective. And so as that company, as that grows, you way want to increase the amount of scalers that are ecosystem scalers. You know, hey, our systems are kind of going to get challenged or we're hiring too many people. You need scalars to take care of air quote the home and yeah, so it's, it's, it's really kind of a ratio. I don't think there's like a, well.
Interviewer
Let me, let me pinpoint an industry because I saw in your background you've worked at some very large companies and some of the hotter companies of today I think anthropic maybe have you done some work with them?
Casey
Of Course, I mean there's a whole, I haven't done work with them. No. But obviously.
Interviewer
Open AI. I mean there's some big, huge companies out there, but it looks like they're hiring a lot of people to me. And, and I wonder like, what's the right model to sort of follow if you have one of those types of just companies that are completely blitzscaling the market, to use your phrase, sort of, you know, the idea that AI is going to be doing a lot of this. But Here is an AI company and it looks like they have 50 job open scenes whenever you take a look at them. Right. Anthropic or OpenAI or those types of folks.
Casey
I mean I, I don't know the intimate details of those companies, but I can guess from the speed and aggressiveness of their growth. Yeah. And their market potential that it's a ratio thing. Right. So if you're, you know, selling to a much bigger market and the prize is so valuable, it makes sense to hire ahead one, you're just fighting a bigger war. So you just need more, more of everything. It's just a size thing. Right. When you're talking about billions and billions of revenue and thousands and thousands of customers, that right there tells you also the ferocity of product development means you probably need more resources to keep ahead of the product curve. And as an organism or system gets bigger, you need more coordination. Generally speaking, you know, there's, I don't know, 100 people at IBM that just do payroll. Right. Just do payroll.
Interviewer
Right.
Casey
So it's a race show thing. So yeah, I think that.
Interviewer
I've started, I've started and, and advised a bunch of different companies and you, you definitely have a, a different view on things and it's an educated one. I just want to be able to tap into that. As you share your insights with other early stage companies, what other things do you tend to sort of lean in on? And some things that you recommend startup founders consider and evaluate.
Casey
What resources?
Interviewer
Yeah.
Casey
Oh, I mean, I mean I, this, this sounds biased, but it's not. It's when I, when people ask me they're getting into startups or new job, it's like, oh, do you have a mentor book, you know, or blog you could recommend me or a podcast? I'm like, no, there's no any mentor or that's going to cover whatever is the unknown. But what I have found to be incredibly effective is a network or a community. Because if you think about a network community, it's a living, breathing thing of people. Now AI that it sits on top of the changing world. So as the world changes, your community updates and refreshes. For example, when Chat GBT came, the community came together at OG Operators Go and was like, what is this ChatGPT thing? And so we started evolving into it as a group. You know, we had people using it for this and he's okay, but there's no static anything. There's no mentor that would know that. There's no, it's. You got to be real time and flexible. So AI to me in terms of OG is authentic intelligence. Right. It's, it's, it's human intelligence.
Interviewer
No, I'm going to double click on.
Casey
A community that's relevant to you.
Sponsor Representative
Yeah.
Interviewer
On the community aspect. And then how, when the community throws out, hey, what do you guys use for payroll? Hey, what do you guys use for hr? Hey, what do you guys use for xyz? Other tools that sit in your, in your areas of expertise. How do you sort of evaluate those things? How do you share that?
Casey
Oh, so we have an online forum and an archive of 10 years of past posts where people ask questions about problems they're solving. Hey, I have a situation. Or one's like we just moved to, you know, we're expanding to Canada. Has anyone hired and set up payroll or for Canadian engineers? Wow, okay, there you go. And since I've been Canada payroll or you type in Canada, you'll get those. And of course there's real time, you know, OG members helping each other.
Interviewer
Yeah, that's great. OG definitely sounds like a cool group. What is the other thing that you look at, Casey, that you just, you, you sort of cringe when you see founders and, and small startup teams doing that. You just go, ah, they fell into the trap.
Casey
I think probably.
Interviewer
Sometimes hiring a certain position too soon, too late, or maybe starting to do certain spends.
Casey
Yeah, I do think spending, spending a little too early before things are more certain. Or I should say thinking you need to hire five people when it you just need three. That's really hard because when you, when things are going and you got a big VC investment and people are excited, everyone's full charge. So what is over hiring? And now look, there's rare exceptions like an anthropic or open AI where they might be under hiring. Right. But for the most part, unless you're that there's a chance you're over hiring. And you'd be surprised, you'd be surprised what you can do with half the amount of people you know and still keep a great culture it is kind.
Interviewer
Of funny how you know these, everyone's talking about the, the two person or one person billion dollar company and such. But the reality is all these companies that are hot into AI right now are spending like crazy as well as hiring like crazy. Hey Casey, this is awesome. I don't want to, I don't want to forget to ask you the obvious question which is how does somebody get involved in Operators Guild and become an OG in your area?
Casey
Yeah. So we have an application process and you just simply go to the website operators guild.com if you take a look at the website, what we offer, there's actually a lot more that we offer that the website doesn't even do a great job going into but apply if you are qualified. You know, we have a pretty strict bar and it's about 1 in 10, maybe 2 in 10 will get accepted just based on the historical average is. Yeah, then we, you share a lot more about, we share a lot more about the community. What we do, what we don't do, who we stand for and then take away from there. And there's also a lot of operations members you can probably reach out to. They, some of them have it on their LinkedIn. You can absolutely just talk to them about it as well. But it's. Go to the website.
Interviewer
Yeah, but is the key criteria experience or the types of companies you work with, what are you looking for?
Casey
Yeah, that's right. It's, it's high growth, mostly tech, generally VC backed. Because of the high growth early stage startups, I would say, you know, series D or earlier when you get much later it becomes more of a specialized type of situation or group, it's just different. But when you're earlier it's much more of a generalist scaling, horizontal type role.
Interviewer
Right.
Sponsor Representative
Okay, so final question.
Interviewer
Casey, you're, you're sitting in the catbird seat because you've seen so many really interesting deals and help shape a lot of these companies. But looking at the, looking at 26, 27, you know, these are going to be some fast crazy growth years. What are we going to see in terms of, of where things end up for some of the, the large AI startup companies in terms of their efforts to get a, a foot planted in the market. Are we going to see many succeed? Are we going to see one succeed? Is this the battle of, you know, super superheroes and only one survive? How do you sort of foresee this market taking shape?
Casey
I think AI is a completely new ecosystem. Just like software SaaS became a whole new ecosystem or Just like the industrial revolution was a whole new ecosystem where you had auto insurance companies and tire makers and you know, it's a whole ecosystem is now being built. For example, there's companies that are brokering GPU chips, there's a whole market being developed for leasing GPU chips because that's the new oil, so to speak. So I think one is a lot of new categories of air quote, vibe, coding, replit, lovable, that's a whole new thing. So there's a lot of new categories for new ways of doing things and then within that I think there's going to be a lot of false starts. There's going to be a lot of. That's the beauty of innovation, right? You try and one hits amazingly and others don't. I think the big players, there's going to be some mega players, no different than the last cycle. There's Google and Meta and the Magnificent Seven. Some of them are going to get even bigger. But this is a very high cost game. So scale matters, size matters and the big get richer. So I think the size disparity is going to continue to happen and a whole new crop of small to medium sized companies are going to be built off of this new ecosystem. Scaffolding Harvey AI I think is doing very well for legal so niche applications via AI that build off the ecosystem, that service a very distinct market and have a brand. So I think a lot of companies that are going to do decently have a very distinct brand, reputation, loyalty with the customers. And yes, I think there's gonna be a lot of go under, you know, as people have honestly, there's a little bit of a gold rush going on.
Interviewer
Right.
Casey
Some get really, really rich and others walk home with not a lot of gold. And that's, that's the beauty of this new phase.
Interviewer
There's always a bit of Darwinism in all of this. Right. Hey Casey, it's really been fun chatting with you. I learned a lot and lots of great, lots of great drops of knowledge because we don't tend to focus so much on the operator function but clearly it's hugely, critically important.
Casey
Yeah.
Interviewer
So when does the book come out?
Casey
Oh God, hopefully a year and a half year. Yeah.
Interviewer
Okay, you got some time, you'll add a few more chapters. I look forward to following you though at the Operators Guild. Sounds like a fantastic opportunity and really thanks again for sharing some thoughts with us.
Casey
Absolutely. Talk to you later.
Interviewer
Take care.
Episode: The Scaler Mindset: How Elite Operators Build Hypergrowth Companies with Casey Woo
Originally aired: February 17, 2026
Guest: Casey Woo, operator, executive, author, five-time CFO, and founder of Operators Guild.
This episode explores the nuanced art of "scaling" in business, as defined and championed by Casey Woo—veteran operator, executive, and now author of The Scaler. Host Keith Newman and Casey delve into what it truly means to be a "scalar" versus a conventional operator, dissect the specific mindset and capabilities that foster hypergrowth, and discuss actionable advice for founders navigating the rapidly evolving tech landscape, especially in the AI era. The conversation combines high-level frameworks, tactical examples from both success and failure, and Casey’s practical philosophy on teams, culture, community, and the future of elite operations.
“You don't really ever call a Navy SEAL who's a medic a doctor. You don't call them doc… he's a Navy SEAL first.” (04:35)
“We're the horizontal, we are the multi-disciplined. We're the glue.” (09:45)
"There’s no mentor… that’s going to cover whatever is the unknown. What I have found to be incredibly effective is a network or a community… it's a living, breathing thing of people." (18:36–19:17)
“We have a pretty strict bar and it’s about 1 in 10, maybe 2 in 10 will get accepted…” (22:10)
"AI is a completely new ecosystem… there's companies brokering GPU chips… that's the new oil." (23:56)
“Some get really, really rich and others walk home with not a lot of gold. And that’s the beauty of this new phase.” (25:42)
Conversational, candid, and analogy-rich with a practical, battle-tested outlook—Casey weaves together operator wisdom and real-world startup scars. The advice is actionable yet humble, emphasizing learning from community and context over dogma.
For More:
Listen to 80+ founder and operator interviews at Liftoff with Keith Newman.