AI's Impact on Specialists: Why Generalists Will Thrive | Casey Woo Full Podcast

The punchline is the CFO is becoming a mini CEO. The days of the Dilbert accounting CFO meme is over, especially in tech. I mean, maybe in, like I would say, slower moving businesses that don't require as much agility or margin of error, then yeah, then you can have the more what I would call budget operating model compliance accounting CFO. At early stage moving very quickly, I always found the CFO title to be misleading. One way I can tell you is, you know, 15% of my calendar was finance. By the way, Salesforce just created COFO and I smiled and finally, finally it has been accepted. Strategic finance, right? That's a very, very common term now. Strategic CFO. All it means to me is business first, finance second.

Welcome to the Startup CEO Show. I'm your host, Mark MacLeod. In this episode, I sit down with Casey Wu, founder of Operators Guild and also founder of FOG Ventures, which is affiliated with Operators Guild. Casey began his career in the military and then into investment banking, and then he was a CFO 6 times, and now he runs the largest community for what he calls non-building executives. So execs who are not writing code and not selling the product. So often that's the CFO, the COO, Biz Ops. And this was a really fascinating discussion, A, for me, because I was a CFO for a long time, but B, he sees a real change coming. He calls these people scalers, and he feels like any role that is just truly specialized is actually in danger of being disrupted by AI. And the future is going to be requiring leaders who are generalists, who can see across the business and leverage AI to get instant insights, instant value. So this was a fascinating discussion. I really hope you enjoy it. Casey, welcome to the Startup CEO Show. It's a true pleasure to have you here. How you doing today?

Good. Thanks for having me.

It's a pleasure. So this is, this is another first on the podcast. A few months ago I had, normally I just have CEOs and I had Matt Turk from FirstMark Capital on a while ago. So this is the first time I had an investor and now is the first time I've had someone who's been in different executive roles. And so, Yeah, I'm excited to have this discussion. I know you began your career as a CFO and I was a CFO for a long time, so we won't nerd out on accounting standards or anything lame like that, but maybe just tell folks who you are and just give us a little bit of background just as a starting point.

So actually that was, I've had too long of a career. My first career is actually in the military and investment banking hedge funds. So I was 10 years in Wall Street. Then my second half is CFO, COO, CEO, 5-time CFO, COO. Now I run Operators Guild. But yeah, so I've had a very, I would say, diverse background as it relates to— well, military is very different than what I call transactional or investing and then building. And now I run Operators Guild, which is a community of scalers or CFOs, COOs, CEOs that invest. So it's like everything has kind of come all rolled in together. Uh, so it's super fun, but it's all tech. It's VC, high growth, crazy tech.

I love it. I'm curious, uh, I actually didn't know about the military background. I'm curious what, um, what you took from that, like how that made you better in the second half of your career, I guess.

Yeah, I think every experience will absolutely, you know, you'll take away something. In no particular order, so I went to West Point. What you learn a lot is when you leave somewhere. So when I left, I missed my team. I didn't appreciate how much I'm a team person, which no surprise I'm in startups and it's just, it's startups are basically building with teams on steroids. That's essentially what it is. But anyways, I learned very much the camaraderie. It didn't matter if I was cleaning a tank, digging a ditch, doing push-ups. I wanted to be with a team because then I did investment banking and I loved it also because I was with the team, even though it was spreadsheets. So I realized the content is sometimes even less important than the actual setup. The other thing at West Point is designed to do, like all military, is to have you face failure. Mm-hmm. So you're not the customer when you go to West Point. They pay you to go there. Um, so they dictate all that you do and they will guarantee you fail. Uh, for example, just in the athletics department, we all have to do gymnastics, boxing, and swimming. I've never met anyone great at all three, right? Same thing on the— anyways, I can keep going on and on, but the point is You're going to face a lot of bumps and you're going to have to deal with it. And the third is leadership. It's a leadership institution. So I think you'll go through over a dozen, probably, leaders or managers, air quote, in a year or two years. It's the way it's designed. So you get to see so many different leadership styles. You start figuring out on your own what's effective as both a follower and leader. Et cetera. So those are the big ones.

That's fascinating. You didn't say it, but I'm guessing you took a whole bunch of discipline with you as well.

A lot of people get there are pretty disciplined by definition. So in that sense, yes. I think the most simple thing I learned was being afraid, scared, or regret doesn't do anything. So when you're in a situation and you're being very bothered because of anxiety or fear, it doesn't help you. I know that doesn't mean it goes away, but eventually you, I don't know, it could be as simple as I lost my passport traveling. Let's say like, oh my God, the old me would start panicking. And then you're just like, okay, I lost my passport. Like, what is the next step? Next step is go to the embassy, change my flights, tell all my meetings I can't make it. You know what I mean? You, you just move forward. All the panic doesn't get your passport any faster. So that, that's a very simple thing you learn. I mean, in startup CEO land, you face that all the time. You face a problem every day. And I think a lot of startup CEOs who are listening will be like, yep. After a while you're like, 90% of the things, no need to panic.

That makes me think of an old movie, Apollo 13 with Tom Hanks, and they're hurtling to the moon and like they're gonna run out of oxygen and back in on Earth they're like calm, like, like let's just work the problem. He just kept saying like, let's work the problem, right?

Like, yep. Like that's exactly right. A lot easier said than done, but I think as we all do in startups, you know, you get beaten down enough, you know, you start to learn, okay, you know, it's not the end of the world.

That's right.

Let's work this problem out.

Yeah, 100%. You know, my, my operating days are, are long behind me, but I can remember times when in the moment it was just like, oh my God, the world's ending. I was like a total drama queen in my first startup and I would get a colleague to drive me home because I was too stressed to drive. It was just ridiculous. And then, and now it's just like a distant memory. It's like, whatever, you know, that was silly. And then of course, uh, at the risk of getting too woo-woo, everything including those challenges happen for you, right? Tony Robbins wouldn't be who he is if he didn't have an abusive mother, you know, it's just like everything shapes you, right? So, uh, you learn that over time as well. So you've been a CFO for a bunch of time and I, I don't wanna spend too much time there, but you know, I'm biased 'cause I was a CFO for 14 years, but I feel especially as a company gets older, the CFO role is really important. Like I liken finance to being like, you know, if you're building a tall building, you need a deep foundation and like finance is the foundation of that tall building. So, you know, I'm curious from your perspective, I don't know, I mean, what makes a great CFO? In the, for a startup?

I think this is a great question now. Um, so my group just ran CFO Summit, so it was 100 of some of the best tech CFOs together. So I have a lot of things coming off of that. The punchline is the CFO is becoming a mini CEO.

Hmm.

The days of the, and I pardon my, my crass directness, but for simplicity's sake, the days of the Dilbert accounting CFO meme. Is over.

Mm-hmm.

Especially in tech. I mean, maybe it, in, in, I would say slower moving businesses that don't require as much agility, um, or, or margin of error. And then, yeah, then you can have the more, what I would call budget, operating model, compliance, accounting CFO. At early stage, moving very quickly, I always found the CFO title to be misleading. Uh, one way I can tell you is, you know, 15% of my calendar was finance. And then, you know, that's, oh, by the way, Salesforce just created COFO and I smi— and I smiled and I was like, and finally, finally it has been accepted. Uh, strategic finance, right? That's a very, very common term now. Strategic CFO. Uh, all it means to me is, um, business first, finance second.

Mm-hmm. So you can go beyond numbers. You got the context. Yeah.

And they're T-shaped, so they understand business and all around, but they're spike in finance or accounting or con, et cetera.

Mm-hmm.

So yeah, so I think the CFO these days, especially with AI, and this is wild. What the whole reason OG started was because CFOs, CEOs were nobodies. 10 years ago, uh, I was asked if I coded or sold anything in my Stripe interview. Do you code or do you sell? And I had a Wall Street background. I'm like, I can try, but I do a thing called finance and I can clean toilets and biz ops. Like, what is that? Are you an accountant? Because we have accountants. And I'm like, no, I'm not an accountant. Well, then you have no job here at Stripe. Now, Who would've thought a computer science degree is more shaky than an oil painting degree? AI is eating up specialists like crazy. We were the non-specialists, what I call the scalers. We were the biz ops, the CFO, the CEO. Many CFOs are COOs and, and you know, CFOs are becoming CEOs because at early stage, a CFO's pretty much, you know, an operating CEO if they're good. So anyways, I think you guys get the drift, but it's with agents now with AI. I couldn't believe Mark Andreessen had this video. I think I played it 4 times. I had goosebumps. He basically said, yeah, the world is moving toward multidisciplinary generalists.

Oh, wow. I did not see that.

Who control agents. That's us. That's been my community for— we didn't find a community because everyone's like, what are you? Are you a lawyer or a doctor? Are you like, I want to put you into a vertical right now. I'm, I'm, I just get it done. I get whatever is done that is not getting done, and specifically in finance. So anyways, that's the biggest takeaway is scalers and generalists, I think, are now where the world is moving. And by the way, startup CEOs, a lot of them are scalers. They're, we do multidisciplinary to get anything off the ground, but specialists need to be careful.

Hmm. That's so fascinating.

Everyone needs to be careful at the end of the day, but I think in the first go, it's very clear the junior jobs, the specialists, if you just program, so to speak, and don't have ideas, what they call it, there's like the execution engineer and then the, uh, the engineer with an idea. The execution engineer is at, at risk because what is AI doing? Executing. So ideas and strategy are cross-function. It's far more complicated. That's where there's still a role and CFOs. Know all the numbers, right? So in a business, let's not forget what a business is. It has to make money. People think it's just a product. No, the numbers are really important. So that's why CFOs are starting to become really potentially good mini CEOs and really important strategic partners to CEOs, if not becoming CEOs themselves, which is what happened to me.

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So if you think about a CFO in the past, we were locked out of the data because we're not technical. So if you wanted customer data, you wanted that, you had to go to the CTO. Who held the keys called being technical. Now the, the data's moving to the center is what I call it. So besides, we just had before CFOs had accounting data and, you know, receivables, payables data. That's it. Now it's Chief Business Intelligence Officer. Think, think, um, CIA. Chief Data Officer. CFOs hold more data and knowledge probably than even the CEO, because the CEO's busy fundraising, whatever. They don't see the numbers. Once you have numbers married with metadata, like who your customers are, what are they buying, and now AI makes it so easy to combine unstructured money and non-money data. But if you think about CFO training, we're trained to read things as a business person. Now there are salespeople who can do that. Engineers, less likely, right? If you're purely an engineer, you're not really trained in the art of taking marketing data and marrying it with product data. That's just not your training. You're very good at building product, right? So this is where, think about it, it's once the AI agents suck in everything, who's the best person to decipher and read it all? It's probably not the AE. It's probably not the paid marketing specialist. It's probably not the front-end engineer. It's the COO, CFO, Biz Ops, head of strategy, or CEO. It's the center people.

I love that. For me, this is about maybe the difference between data and insights. You know, companies are swimming in data.

That's exactly it.

Maybe short of insights and someone who can crunch and synthesize and just be like, hey, This is the nugget.

This is the head of BI. BI is just insights, right? It's actionable insights. But I tell all CFOs, this is, this is your world now. This is it. And if you're not doing that, you know, you asked your first question, what's, what do CFOs should be doing? If you're not truly being the head of business intelligence and displaying things to people that are like, oh my gosh, we need to change the way we product, or we need to, it's not product, the way we build or this feature. There's so much intelligence and insight when you combine it with money, that it's the job of the CFO to present that. A lot of pressure, a lot of responsibility, a lot of privilege.

Tell us about your Operators Guild, please.

Operators Guild started very innocently with 9 of us 10.1 years ago, April 2015.

That's very precise.

Yeah, well, it's because we had our 10-year anniversary and I— it's nice to say 10, but it's no longer— it was because I was lost. I was an ex-banker/hedge fund finance bro, you know, one of those types. And there's people leaving McKinsey and Bain. Because the whole story is when you go to college, you don't go to a small business when you leave. Who does that? No, you, you graduate from Wharton, you go to Wall Street, or you go to management, or you go to, you go to IBM, or you go to Amazon. You don't go to sub-20-person companies. And then it started. Um, and it's increasing, right? So I went and the answer was there was no group for me. So when I came here, it literally was, I'm sorry to offend anyone, it's like Dilbert CFO groups. It was basically accounting group, which is fine. And when I say Dilbert, I just, it was that persona of don't ask them to forecast, right? Don't ask them to forecast. Their job is to get the books done. That, that was the idea that, you know, they wore a blazer, looked really nice, but weren't the life of the party. Okay, cool. And then you have founders who are mostly fundraising and, pounding on doors to get money and in Aspen, right? Because those days money was really hard to come by. Like you gotta, you gotta still like, so 9 people started. There was, we weren't CFOs per se. COO doesn't really mean anything. It just means one minus CEO. We weren't CEOs. We were in this middle and there was no group for us, period. So that 9, uh, we're the only professional paid community I'm aware of that's ever 100x'd organically. We don't have a sense. We're now 1,200 people. I say this not because of any like, oh wow, that's a cool vanity stat. I say this because it tells you the product market fit. It tells you the world needed this. Anytime you have 100x growth paid, it's not a free group, word of mouth, it's because there was a need that was not filled. And this is the inspiration for, I told you, my book is The Scaler. What, what is going on? What are these people? It's a new profession that got created. So Operators Guild is 21 chapters around the world. Think YPO, but for early stage builders that don't code and don't sell.

Got it. So not just CFOs, but yeah, COOs, et cetera.

Yeah. So we have early stage CEOs, 'cause that makes sense. 'Cause when you're early founder, you're everything. You do everything until you hire a salesperson until you hire a CFO. We are the, we don't code and we don't sell people and we don't do law, right? So we are CFO, COO, Biz Ops, Chief of Staff, RevOps, strategy, early-stage founder CEO.

That's amazing. I wish I had that back in my operating days. Now, are you creating content or are you really just facilitating people coming together?

Yeah, so we do two main things I would call social networking and education. So we, we're known for our events, 12-person dinner parties, 50-person happy hours. We hold 2 summits, CFO Summit, OG Summit. So that's just, I mean, we just got the reviews back. Content's great, but you know what people really love? The people. You learn every time. You can have Barack Obama speaking or whoever. That's great. I love the people I met. So I call it therapy, friendships, relationships. Feeling understood. And then the second is, you know, really good content programming, problem solving. So if you think about what we do, all we do is solve problems. That's all a business is, is just a series of problems. But in early stage startups, they're all new and nuanced and infinite permutations, especially as technology changes. But imagine if you had a group of now 1,200 of us that collectively have solved probably 80-90% of any problem you will face. Or if we don't know what it is, we collectively figure it out together like AI. So it's pretty classic, you know, like any YPO group, etc. There's a forum online, but a lot of the relationships start to build personal board director-wise outside, like peer groups. We don't have formal peer groups. And then the last thing is we have investing and talent. Those are separate, but OG itself does education and events, and then we have a syndicate that where we invest together. Called FOG, and then we have Guild Talent, which is a talent agency for us, both hiring and to be hired.

Yeah, that makes— talent makes a ton of sense. I could think of so many ways you, yeah, you could go with that, but that's amazing. And so, um, yeah, I didn't realize the FOG acronym was related. So, so everyone comes together, uh, co-invests in companies as well, which was just going to create even more bonds between you. That's really cool.

Yeah. FOG stands for Four Operators Guild. Yeah. So, so yeah, it's, uh, but basically it's an entire ecosystem that services the scaler.

Yeah.

That no one understood before.

So the term the scaler came out of running Operators Guild. You realize these people, that's what they are. Is that right?

It came out of me realizing there's this message to get out and to write a book. And then the book agent says, what's the title? And I was like, uh, Generalist, the Operator.

And we're like, that's it. We're like, here's your bum. Boom. Here's the title.

Yeah. And we're like, What is it? And the best I can come up with, and by the way, anyone on your, who's listening, if you can come up with a better category label for what I'm describing than scaler, I would owe you a nice steak dinner. Um, but yeah, so it's, it's a, I would say I coined it, phrased it. If you look in the dictionary, there is no definition for scaler, but I think people get it pretty quickly now. Um, but generalist just gets confused with you, you're not good at anything or you're an intern. Um, so scaler has a, a more apt definition.

I'd love to unpack this, um, insight about how you think specialists are vulnerable, which I don't disagree with, but like for all of my career. Um, and like my advice to my kids who are just graduating, well, one's graduated high school and is in college and the other's, you know, just about to go is like, hey, you need a skill. This is my guidance before AI. And like, you need to kind of pick a thing and pick a craft and be really good at it. And, um, I would always, whenever I had to remove leaders from companies because they couldn't keep up with the scale of the business. Often it was because they didn't have a specialty, like a co-founder would over time just become the VP of special projects, right? Because they just, they didn't have some functional discipline. And so that was a world where specialty was rewarded. So are you saying now, like, that's no longer the world? That co-founder who's a little bit good at everything, are they going to go further?

Yeah, that's a really good call out, because by definition, generally when something gets much bigger, you— it requires specialization. So I think it's a complicated answer. It's a great question. Let me see if I can tackle this succinctly. Um, what I'm learning is the, the functions I think will still be there. Like, there's a marketing need. There's an engineering need. I think what happens is it's more senior. So the head of marketing is much more multidisciplinary, whereas the writer, the copywriter, who's more junior, like hyper-specialist, is at risk. But if— but to run marketing effectively, you need to be more multidisciplined. For example, you may I need to start understanding finance better, you know, read metrics better, et cetera. Um, and less so I need to write, it's more strategic. So it's everything senior, senior engineer needs to have. They're saying senior engineering looks like product.

Mm-hmm.

Because think about it, like if in fact they're thinking product people are gonna rule it because they have the ideas, they know how to— so what is product? Product is actually a multidisciplinary person, right? They marry technical with marketing with finance. So product is actually an underserved, like under understood. They think product is a specialty.

I've always thought that the best product leaders are mini CEOs.

Bingo. In fact, I invest in most of them. That's one of my heuristics. It's 100% spot on. So I think product people are gonna get very, very influential because they're not held hostage anymore by engineering.

Mm-hmm.

Air quote, you know, just they're, they're, they're hand in tight.

Yeah, I get it.

Nope. Okay. As it relates to, I think, the VP of special projects, yeah, first of all, I think there's two types. There's those that are really like not getting into anything and then they're just floating around because they're a founder or a co-founder or whatever. Yeah, I, I think you gotta find something. There are worlds now, you know, you call it chief business officer, chief data officer, that those people, if they have the right skillset, become. Meaning there are new jobs being created that are legit specialties in the future. Like, I'm gonna make it up, Chief Business Intelligence Officer, that those people can actually now do because they don't have a marketing background or an engine, but they are business people. Could be business and insights is probably the next one, or running AI agents. So they start to pick up the skill sets of running AI, right? So I think there's new job creation is what I'm calling it for multidisciplinary people. Um, but yeah, the VP special projects will eventually just go away, right? All those things eventually go away because they're gap fillers.

Fascinating. So I don't know whether you run these surveys or just have anecdotal evidence, but like what's keeping your members up at night?

I think there's a lot of pressure. To use AI, both on the CFO, COO, CEO side will be your board saying, why haven't you increased your operating margins?

Mm-hmm.

I heard from my last board meeting and my last co— I heard this, I heard that.

Yeah, yeah, yeah.

They went from a 900-person customer support team to 60. Why aren't we doing that? Right? Or why did you send me an old school board deck, both for profit margin reasons, efficiency reasons, but also kind of like staying relevant, staying ahead of the competition. So I think velocity has only increased. I think Zuckerberg said, oh yeah, we could be wrong. It doesn't matter because we're so fast. So whatever we try, whatever we do, oh, we're wrong. What's right, and then we just move so fast. Our talent is so fast. So speed. So a lot of pressure is just— we thought it was fast before.

I know.

I mean, because AI has just made everything within seconds or minutes rather than weeks and hours and months. So, so yeah, it's, it's velocity. And also, I think another big one is, um, risk-taking with AI, right? But by nature, operators, finance, they're protecting the company. So they can't just inject wild types of tools that, you know, have real downsides. So that's a really big one is rules, regulations, compliance. I think the divide there is simple. If it has to do with life or death, or like people's money, you have to slow down. Like you can't just try random, like, you know, healthcare or fintech type stuff, like actual, but if it's like productivity tools, project management, note takers, summary, like you go ahead and go crazy.

Yep.

Because it doesn't kill anyone if it's off, but it's better to be using it than not. So that's what's happening.

So AI, at least horizontal LLMs have a propensity to hallucinate. And as a finance leader, right, that I don't, I'm guessing I probably have a zero tolerance for hallucinations. So how do I, how do I use AI?

I think in the beginning it's spot checking, it's constant testing. I heard a great answer to hallucinations. This one company, I'll leave anonymous, they had hallucinations. They were in the travel business. So literally the AI agents were creating flights that didn't exist. So people would say, oh, your flight is missed. Why don't you book this one? They're like, okay, oh, what? It doesn't—

okay.

So what they did was they have another AI that checks the AI because it's incredibly unlikely that you have the same hallucination. So all they do is say, is this real? And then the other AI machine goes, I don't see that. Okay, then it's hallucination. So it's AI on AI. It's almost like an AI QA machine. Um, that was a clever one, which is try— it's like a double blind. It's like, can you recreate, you know, this fact or this thing? But I think in the beginning it's, it's try it and see how accurate, try it and see how accurate. And then you'll start to see, okay, it's pretty good here. I can start trusting it 9 out of 10 times or 99 out of 10 times or 100 times. It's great., but over here it's weird, you know, whatever that is. It's, it's just pretty classic trust but verify is what we call it, right? So I don't think anyone's using it blindly. Now maybe they are, but I think for CFOs they will try it and then what happens is it gets better than you. It's like Waymo in the beginning.

It's like, ooh, ooh, oh, oh, I don't—

well, okay, it's, its safety record is now better than Oh, okay. And it swings over.

So I think you've shared this already, but maybe just to, I don't know, just make sure it's there in like a couple of sentences. What is the central thesis of this book?

Startups used to be a hobby. They are now a profession. It is a professional career now, just like a professional sport has been created called early-stage hyperscale. There's an entire education set that'll be run. Stanford will start to teach it in 10 years. Our children and grandchildren will no longer just have Wall Street, management consulting, or corporate, or lawyer. It's gonna be scaler. Now, scaler, funny enough, is what I mean by that is founders are extremely well covered. Everyone knows the CEO founder. We're talking about the number twos and threes, that those are the ones who, when Elon says, this is my vision, someone builds it. Now at the same time, there's founder operators, right? So they become founders. But anyways, that's the central thesis is there's a persona, it's a personality type that's never been categorized. That is now it's in its first generation that will become as sturdy as an engineer or a marketing professional.

And so is that your specific focus for Operators Guild? You're going to bring these people together and have the content and programs so that they make this transition and become that person?

Yeah, the, the silly analogy, but it works, is so the, the title is The Scaler, uh, the working title, The Rise of Special Forces in Business. So bear with me. Special operations is new in military. It's, it's about 100 years new or 70 years, 70 years new. And the reason why is because, uh, wars in the past were huge. They were World War I, World War II, massive. So what do you need? You need specialties, branches called Army, Navy, Air Force, right? They specialize in land, sea, and air. And then all of a sudden it didn't matter if you had a million people and the biggest budget in the world, you started having guerrilla warfare. So Vietnam War. So then they're like, oh crap, we need to create things called Green Beret, Delta Force, Navy SEAL. They're a completely different type of person. They are generalists. They need to know how to do a lot of things, but there's only 10 of them on a mission. So there's not this army, bring in the army and then bring in the Navy. No, no, no, no, no, no. Osama bin Laden was like 20 dudes and they all had to figure it out. That's what happened in business. Business was all big. Amazon versus Walmart, Pfizer versus whatever. And so we're all specialties because they're huge.. And then all of a sudden, this early stage hyper mission called Series A, Series B, high stakes, high money, high sophistication has never been created before. And so we created special operations in tech. So to answer your question, think of it like creating a Navy SEAL organization. So all I do is represent us and give Navy SEALs therapy, education, community, investing opportunities. And jobs or deployments. That's the whole world is special operations for business, but it's a specific persona though. So we don't service engineers or salespeople. It's builders, non-technical builders.

I love it. Like I say, I wish I had it when I was operating. Let's talk about BizOps for a second, cuz it might mean different things to different people. People might not know what it is, but like, one of my CEOs has just had like an epiphany with respect to Biz Ops, you know, like with CEOs often over time you become the bottleneck, right? Like everything kind of flows through you. Everyone kind of needs your guidance. And he's just, he's built this whole Biz Ops function that reports to him so he can go in and be like, here's a problem or here's an opportunity or here's an outcome that I want. Go make it happen. And then he deploys and like off they go. And so like he's gotten like massive leverage. And so now he's doubling and tripling down on this. And so I'm curious, like, is that how you think about BizOps or what else would you tell folks who are thinking, hey, maybe that I need that in my company?

I love that you brought this up because at OG Summit was 2 weeks ago. There's a whole session on BizOps. So 10 years ago, the number 1 question I had in my tiny community, Operas Guild, was WTF BizOps. Like, what is it? I had it in my title and it was the hardest thing in the world to explain to someone what it is. So we created a Bible around it and a playbook and it was really helpful. And so meaning it was very brand new, like even we were describing. And the whole topic about BizOps was everyone's BizOps now. And BizOps is not just the function that we think of it as.

Mm-hmm.

It's very similar to kind of what we talked about, which is this hyper-agile insight machine that is multidisciplinary. Um, whether it consults or it executes, that's kind of the decision of the CEO. You know, think of it like a CIA can inform you or they can act on it, right? So I do think it's that. I think BizOps is our mini mini strategy pods that can be massive leverage, both internal and external. So one topic was, are you working in the business or on the business? So, you know, um, on, on the business is the product, the, the consumers, right? So a lot of times BizOps can work on there, but what people don't realize is BizOps can be a huge leverage for in the business. So anyway, so the answer is yes, absolutely. The same thing, I, I won't bore everyone, but the same exact reason why CFOs have become so central is the same reason why BizOps has become, except it may not be finance. It's now a new thing that doesn't have a lot of finance involved. So it's like start starting, like, do we go to London? You know, should we try this? Right? It's money's not involved yet, but there's enough intelligence to say, wait a minute. I think there's a signal here that our customers want X. Let's try it. Or I think we should try this. Or so it's quick experimentation also. Uh, but BizOps is no longer kind of the, the, the side cost center thing. They have more power and they are led by potentially like the VP of special projects, right? Except now they have more quick finance information. They have more ability to try things and fail small. It's less consulting and more, you can start to act on it.

I don't know if you agree with this, but there's like two personas of hires that I made back in my operating days that really worked out well for this sort of strategic generalist. One was McKinsey consultants who were sick of flying out Monday morning and coming back Thursday evening. And then the other was VCs who had maybe done a couple of years, but now needed to go get some operating experience before going back on the partnership track. And in both cases, like the thing that— the commonality, I guess, between those two personas is super smart, capable of digesting a ton of information and synthesizing the nuggets. And, you know, comfortable in front of senior people and going in a boardroom and speaking, You know, and so I hired, I rescued a McKinsey guy and made him my strategy head at FreshBooks. I hired a VC and made him my business development head at the same company. Like, all right, I've just had lots of success with that. So are you seeing that across your companies?

That's exactly a scaler.

Yeah.

In fact, I'm taking notes when you said on the book, it's, it is a very, very defined personality. I'm gonna add the whole, Comfortable speaking in front of senior people. I think that's an interesting one. No, we digest a lot of information very quickly. Um, it's clock speed is another one. It's just literally speed of processing. Oh, like an AI machine, right? Oh no, 100%. That's, this is the entire OG thing is these, uh, like I said, ex-McKinsey, ex-Goldman, like we, that's who a lot of us are. Ex-law firm. They're just smart, curious people. Whose personality doesn't like doing one thing. Um, you can call it boredom, you can call it ADHD, neurodivergent, seek stimulus, which is a very common one. I have that. Um, but I've spoken to 1,200 because I, I interview every applicant over 10 years, 1,200 people. And I'm like, oh, I know this breed real well. Their LinkedIn profiles are generally all over the place. They're zigzaggy, and it's because of their personality. It's not an accident. So that's what I'm telling people. This is not an accident that you are a scaler, right? That you've been drawn to this. Why? You were at McKinsey and you got bored. So, so is that a coincidence or is that your personality being allergic to something? So the allergies of our personalities will lead us I always say, have you been to an accounting conference? Why do they all look alike? Have you been to a lawyer conference? Why do they all look alike? Have you been to a plastic surgeon conference? Why do they all look alike? Have you been to a scaler conference? Why do we all look alike? It's just another different personality that's never been categorized. So the one you're talking about was the, I don't know where to put you cuz you're some generalist McKinsey person. But yes, if you put them in the right place now with AI and data and with a BizOps project or mandate, they are very, very effective. And not a cost center.

I'm curious, other than hopefully financial gain, what benefit do you see from having the members invest? Like, does it make them a better leader? And if so, how?

Oh, invest in terms of my syndicate?

Yeah. Yeah.

Oh, the number one thing is the education. When you start to invest in top tech deals, you see what's happening in the world. You stay in front of the very, so I don't know, defense tech. Have you seen Anduril?

Haven't.

Like Terminator. It's like Skynet. It's like what? It's like drones and robots fighting. And you're like, whoa, Replit. Replit. I was like, what is this? And part of it, you get to see the metrics in it too. You're like, oh my God, I've never seen something grow like this. And so when you study comp— forget about even, you know, investing. A lot of people don't even invest, but it's, it became this like incredible newsletter if you think about it. Whereas you see the deals, you see what's hot, you literally see what's trending. So Fog is known for like tier 1, high, like we, we don't do like every other deal. Like we literally try to do what's very interesting or high quality. Now sometimes that's even a lot. So yeah, so, so one of the main reasons is staying up to speed on stuff. You can also call it entertainment. We're, we're all geeks and nerds. We're business nerds. Like when you see this stuff, you're like, wow, like what a cool product. What a cool go-to-market. Like it's just that. Oh, and then by the way, if you want to put, put some money in and join them, there you go. Right. So it's a really fun, like real, real time, see what's going on and participate. And it's fun. It's fun to say like, this is wild.

I don't know.

I'll put in 10 Gs. Let's see what happens. And then you follow it. And you're like, oh my God. You know? So it's just, it really is fun is the word.

That's so cool.

It's, it's super fun.

So, so it sounds like you've got some good deal flow access over the years then.

Yes. If you think about it, money has become a commodity. Don't get me wrong. VCs have a very important place in the world, but after you get your money, there's only many second closes now. Why? 80% of the money is just wire me the money.

Yep.

20% now is strategic, truly strategic. So when I say we have 1,400 CEOs, CFOs, COOs, Like, that's a whole different ballgame. And by the way, 80 will show up to your super pitch for 1 hour. You tell your BD team how long it would take you to get 80 decision makers for 1 hour on your timeline. And by the way, these are B2B, so we specialize in B2B. So if you're selling to us, if you ever tell a CEO, I'll bring 80 leads. In 3 days to you, that will pretty much trump most checks.

That's fascinating.

Now obviously it's not an explicit sale, whatever, but it's, it's, it's perfect, right? Hey, we're customers and we're interested, so it works out for everyone. Uh, but also they want them as talent advisors. They want you, me, ex-operators, because the money is there. But man, you know how hard it is to build now? They got the money. They need to go back to right now. They need Navy SEALs. We're all fighting wars. They need more soldiers. And so there's a soldier group who invests. Yes. I want to talk to them. It's the rise of the operator.

Makes so much sense. Maybe final question, Casey. Like, so you've got these 1,200 people who are these scalers. Is this a movement you're trying to create? Like, Is, yeah, I don't know when you're done and you look back and you're like, okay, mission accomplished. What, what is, what's the mission?

The short answer is yes. I've never really, it's every once in a while crept up. It's just happened to me gradually, but I feel so strongly about this persona. I was member number one. I'm not the founder. I'm member number one. We are an under misunderstood, you know, group, just like any It could be alcoholics, it could be moms. They all create groups to be understood. But this movement is, yes, hey, by the way, 18-year-old kid out there who's wondering what you want to do, you picked up my book and you're like, oh my God, this is what I want to do, right? So it's, it's, it really is like finding your passion. That's what it is. I want people who are like, wait, I'm actually more of a Navy SEAL than an Army guy.

Good.

Start 10 years earlier because it took me way longer into my career to figure that out. So here you go. So it really is that, and seeing people passionate and happy at what they do makes the world better in every angle.

Amen. Yep. Well, Casey, this has been a real pleasure. I wish you and Operators Guild existed 20-something years ago. Um, but this makes me very hopeful for the next generation. Yes. When does your book come out?

It was just started.

So just starting. Okay. Yeah.

Or trying probably next year.

Yeah. Cool.

Great.

Thanks for coming on. I really, really appreciate it.

Yeah. Anytime.

Hey, thanks for listening to the Startup CEO Show. If you'd like to connect with me, be sure to visit my website at markmacleod.me or follow me on LinkedIn at The Mark MacLeod or Twitter @MarkMacLeod_. And if you want to tune in again next week, be sure to subscribe on YouTube, Spotify, Apple, or wherever you get your podcasts. We'll see you next time.