Casey Woo has never taken the conventional path, and that’s part of what makes his perspective so valuable for startup founders. In this episode of Startup Success, Casey shares the journey that took him from Wall Street to startups, why he came to see himself and others like him as “silicon valley misfits,” and how that experience ultimately led to the creation of Operators Guild and FOG Ventures. Along the way, he offers a sharp framework for understanding the kind of talent high-growth startups really need now, especially in a world being rapidly reshaped by AI.
From Wall Street to Silicon Valley misfit
Casey’s early career looked like a classic high-achiever story. After college, he followed an expected path for an economics major, landing in investment banking and then at a hedge fund. By his own account, he had the prestige, the pay, and the view of Central Park that was supposed to signal he had made it. But after years on Wall Street, he realized he was unhappy and ready for a dramatic shift.
That shift took him to a 10-person startup in New York, and eventually to Silicon Valley. There, he discovered something important. The startup world at the time had little respect for operators who didn’t neatly fit into engineering, product, or sales. Casey describes how disorienting that felt, especially coming from a background in finance and operations. He was looking for a community of people who, like him, were helping build companies from the inside without fitting the stereotypical startup mold.
“…if you weren’t coding or selling, you weren’t product engineering or sales and marketing, you’re nobody”
~Casy Woo
That sense of professional isolation turned into a much bigger idea.
Why founders need to understand the “scaler”
One of the most useful ideas Casey introduces is the concept of the “scaler.” In fact, he shared that he’s currently writing a book focused on defining the scaler archetype and helping founders better understand who these operators are, why they matter, and how to spot them.
He argues that many early-stage startup operators are mislabeled by traditional corporate titles like CFO or COO when, in reality, they are something broader and more dynamic. In his framework, these people are horizontal generalists. They may have a functional spike in finance, people, analytics, or fundraising, but their real superpower is moving across disciplines to help a company grow.
This matters because startups don’t operate like large companies. In a big company, functions are specialized. In an early-stage startup, the opposite is true. Teams are small, problems are messy, and roles bleed into one another. The best operators are often those who can jump from recruiting to strategy to finance to internal operations without losing momentum.
Casey’s military analogy makes the point memorable. Traditional companies resemble large military branches with clear specialization. Startups, by contrast, rely on people more like special forces, highly adaptable professionals who can solve mission-specific problems in fast-changing conditions. In his view, that is the scaler.
“The Special Forces of business were created to go in and out of very volatile special situations called Series A, Seed, Series B. And everyone is just jumping on it and doing whatever they can. That is the scaler.”
~Casy Woo
For founders, this is a hiring insight worth taking seriously. If you’re trying to build an early team using only traditional job descriptions and corporate career paths, you may miss the people best equipped to help your startup actually scale.
What a scaler looks like on a resume and in an interview
Casey argues that scalers tend to share patterns, both in temperament and in how their careers unfold. They’re often impatient, curious, energized by building, and comfortable with ambiguity. Many have fast mental cycle speeds. Many get bored easily. Many are drawn to messy environments where they can create order, solve new problems, and move quickly.
On a resume, that often means a non-linear path. Founders shouldn’t automatically reject candidates whose backgrounds seem “all over the place.” Casey suggests that this may actually be a signal of the right kind of startup DNA. A strong scaler may have jumped across functions, industries, and side projects because they are wired for challenge, variety, and ownership.
In interviews, founders should listen for a few things:
- Does the person light up when talking about building from zero?
- Do they describe ambiguity as exciting rather than exhausting?
- Have they stepped into problems outside their formal job description?
- Do they seem more motivated by impact and momentum than by process and structure?
Those are signals worth paying attention to.
Just as important, founders should distinguish between people who love optimizing an established machine and people who love inventing one. Both can be valuable, but they are suited to different stages. Casey’s view is clear: the more horizontal and adaptable the operator, the earlier the stage where they tend to thrive.
How AI is reshaping hiring and scaling
Casey also offers a blunt and timely take on AI. In his view, AI is accelerating the value of horizontal operators while putting pressure on work that is more rules-based, repetitive, or narrowly specialized. He doesn’t frame this as a simple story of jobs disappearing. In some cases, AI may actually increase demand for technical talent and operational leverage. But he does believe it is changing who becomes most valuable inside a startup.
Founders should pay close attention here. Casey’s point is that employees who embrace AI and use it to expand their leverage will remain highly useful. Those who resist it and cling to older, manual ways of working may find themselves with fewer options. If AI can remove a large amount of lower-level manual work, companies will naturally want to capture that efficiency. The winners will be the people who can manage systems, use AI well, and turn better information into better decisions.
“AI is perfect for horizontal.”
~Casy Woo
This has major implications for startup hiring. Founders should increasingly look for operators who are strategic, technically curious, and eager to rethink workflows. The job is no longer just to do the work. It is to redesign how the work gets done.
How the office of the CFO and COO has changed
One of the more interesting parts of the conversation is Casey’s perspective on how the office of the CFO and COO has evolved. Historically, many finance and operations teams were limited by poor access to data. Product and engineering often controlled the systems and information. Finance teams would receive snapshots, build spreadsheets, and work backward from incomplete visibility.
That model is changing. Casey argues that modern finance and operations leaders now have access to far more integrated data across sales, marketing, customer behavior, and financial performance. AI and software tooling are making it easier to pull this information together and use it in real time. That, in turn, expands the role of finance from reporting history to driving performance.
He puts it memorably: the CFO is increasingly becoming the “Chief Performance Officer.” That shift has big implications for startups. It means founders should expect more from their finance and operations leaders than budgeting, closes, and board reporting. The best people in those seats can connect business functions, uncover what’s really driving outcomes, and help the company make faster, smarter decisions.
“The office of the CFO is the Office of the Chief Performance Officer.”
~Casy Woo
The new operational model high-growth startups need
Threaded through Casey’s whole perspective is a broader operational model that founders should take seriously. High-growth startups need business-first operators who can work across functions, interpret messy signals, and combine human judgment with modern tools. Casey describes this mindset as “business first, function second,” and that may be the cleanest summary of what many startups need in this era.
This model is especially relevant as startups rethink hiring plans, team design, and how much leverage they can get from smaller headcounts. The old approach of carving work into rigid silos too early can slow a startup down. A more effective approach is to build around highly capable scalers with domain spikes, then add specialization as the company grows and complexity truly demands it.
In practical terms, that means founders should design teams for adaptability. Hire people who can carry real functional weight while also jumping into cross-functional work. Value curiosity. Value speed. Value those rare people who create clarity in chaos.
Operators Guild sits right at the center of this shift. Casey describes it as the home for the scaler, and that positioning makes sense. For founders, OG represents both a talent signal and a support ecosystem. It’s where early and growth-stage operators gather to compare notes, solve problems, build relationships, and stay sharp as the operating environment changes.
The programming reflects that broader view of what operators now do. It isn’t confined to narrow functional topics. It spans AI transformation, CEO readiness, business strategy, and the real cross-functional demands of operating in startups. That makes it especially relevant to founders hiring their first finance, operations, or strategic leaders, and to operators trying to grow into those roles.
FOG Ventures complements that mission by giving operators a way to support and invest in the tools shaping the future of work. For founders building B2B products that serve operators, this can be a particularly interesting ecosystem to know.
Final thoughts
This conversation offered founders a practical lens for thinking about talent, leverage, and what modern startup operations really look like. Casey’s own path, from Wall Street success to startup outsider to community builder and investor, gives him a distinct point of view. His framework around scalers helps explain why some people thrive in startups while others struggle, and why that difference may matter even more in the AI era.
Thank you to Casey Woo for joining Startup Success and sharing such a thoughtful perspective on operators, scaling, and the future of startup work. We look forward to having you back on the show when the book comes out. In the meantime, founders should check out Operators Guild and FOG Ventures, especially if they’re hiring adaptable operators, building tools for them, or simply trying to better understand the new operating model high-growth startups now require.
Intro 00:01
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.
Kate 00:18
Welcome to Startup Success. In this episode, I sit down with Casey Woo, 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 hyper growth, 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 moderated, modern operators, and how FOG 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 want to 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 Operators Guild.
Casey Woo 01:26
Yeah, so 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 management consulting, corporate job, doctor, lawyer, and there’s one called Wall Street. And I’m 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 of a private equity job. And I was 24, overpaid, it was great. I had this nice office. I remember this Central Park view. And I said, I made it. I just need to keep doing this and keep my job and retire in 10 years. And I made it about eight years and realized I wasn’t happy, and I didn’t know why. Long story short, I left Wall Street and joined a 10 person tech startup in New York, Silicon Alley.
Kate 02:33
Okay, that’s a big change.
Casey Woo 02:35
Huge change, very scary. When all your professional life is chasing Wall Street, and then you leave. Got in, and so I learned that I loved it. And I kind of joke, why do I like eating glass? I love it so much that I realized I had to go, probably move cities if I was gonna do this as a career. And I went to a place called Silicon Valley. I was the recovering Wall Street guy wanting to go into a tech startup. And I went to a little company called Stripe for an interview. It 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 don’t know if it’s a trick question, but I do finance ops, clean toilets. I’m here to know what a real tech company is like, you know, I’m from New York. And they said, you don’t even have a CPA, so you don’t qualify for finance at Stipe.
Kate 03:35
Oh, interesting.
Casey Woo 03:37
And that was 2013. 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 like the second class citizen. (That’s true.) You’re called back office. You’re called GNA. And so I tried to find a community, because I was lonely. I changed jobs. I joined a CFO community. No offense, lot of it was more heavy accounting. Wasn’t my DNA. I wasn’t really a founder. 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 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? That started Operators Guild.
Kate 04:33
Oh, interesting.
Casey Woo 04:35
It’s the only paid community I’m aware of that is 120x in 10,11 years without a single sales motion. So, all word of mouth, we now are the preeminent operator, modern operator, CFO, CEO, early stage founder, BizOps, RevOps group, 20 chapters around the world, et cetera. And then FOG Ventures started five years ago, which is basically the investing arm of OG.
Kate 05:00
Oh, so there’s a connection, I didn’t realize that between the two.
Casey Woo 05:05
FOG stands for For Operators Guild. (Ah, okay), and is now one of the top operator syndicates. And it’s very simple, we are the buyers and builders of tech. So we specialize in B to B stage agnostic, have a lot of fun as a community investing together.
Kate 05:20
That’s great. I will say that Burkland knows Operators Guild, and has so much respect for what you did. I think you brought a lot of respect to that community, right? And a lot of like, empowerment and tools and really helped change some things about the way, like back office and operations were looked at in tech. So yeah, thank you. (Yeah. I’m glad to hear it, yeah.) So tell me, like, when you and I met briefly a while ago, you had such an interesting take right now on scaling a startup, I just wanted to get into it right away. And you talked a lot about, like, scalers and this horizontal, generalist concept. Walk us through that, because we have a lot of like, first time early stage founders listening. And I thought it was fascinating.
Casey Woo 06:13
So given my story, I am trying to write a book because I wanted it to help many others as I realized my loneliness and my path many others shared. So the synopsis is, I accidentally have interviewed 1200 operators, because when they apply to OG, I interview them, and then I am one. And it hit me in year eight, Oh my God, I have it all wrong. I kept thinking we were CFOs and CEOs. At early stage, which I define as, you know, 500,000 person or earlier, high growth, early stage, we are scalers. We are horizontal generalists. CFO CEO titles were borrowed from corporate. So what happened was Tech created a whole new profession that never existed on planet Earth. It used to be in business “small” meant unsophisticated, in general, or low growth. Big meant more prestige, more money. And so when you leave school, you go to IBM, right, go to Apple, you become a doctor, Goldman Sachs. Who in the world is going to a 10 person Series A startup or whatever? That’s not an engineer, right? That’s not a sales guy or girl. You don’t do that.
Kate 07:46
Right.
Casey Woo 07:48
And therein lies the change. A big shift is now tech “small” is sophisticated. In fact, highly sophisticated in a weird way, which is sophistication doesn’t necessarily mean big anymore. You know, OpenAI was 100 people. Let me tell you, those 100 people are highly sophisticated. But the talent is more the guerrilla warfare. So the analogy I use is a military one. So all militaries in the world, all of them have Army, Navy, Air Force. And why is that? Why don’t you have one big blob called Military? The reason why is because humans, when something gets really big, they specialize. So Army is land, you know, Air Force is air. Why? Because it’s too hard for a human to organize around multiple specialties at that scale. The bigger you get, the more specialized a human organization gets right, okay, well, then take it to the opposite. So the smaller you get, the more general you get. So when you join a Series A, Series B, Series C, company, one of the values is being a generalist. And generalist doesn’t mean you’re not good at anything. So that was the other issue is no one says, Oh, what do you do? I’m a generalist. Like, that doesn’t sound cool. You have to say something like, I’m a lawyer or finance. But what I realized really quickly, 15% of my calendar as a CFO was finance. I was doing recruiting. I was in weird strategy meetings. I was trying to plan an offsite. I was moving boxes for an office, and everyone that has early stage knows what I’m talking about. We’re not specialists. We’re specialists at being generalists. So elite generalism, that’s where Tech has basically moved toward. So to finish the analogy, in the military 100 years ago, Special Forces was created. Why? Because it used to be wars were huge – big war, army versus army. Now you have, like, the Venezuela stuff was Delta Force. That’s 20 people. I mean, yes, supported by this stuff, but that’s a very different type of person. They are generalists, right? They eat, kill, swim, but their whole thing is mission by mission, very specific, get in, get out. That’s what happened in tech. The Special Forces of business were created to go in and out of very volatile special situation is called Series A, Seed Series B, and everyone is just jumping on it and doing whatever they can. That is the scaler.
Kate 10:43
I love that. And any one who’s been at a successful startup, I have, you’re spot on, because that’s what you’re doing. You’re doing a million things. You’ve got your specialty, but you’re doing a million things, and you need to be able to do a million things, and you need to be able to move quickly and be fast, and, you know, you’re all just. And so I think a lot of people don’t understand that. You’re lucky you made the jump, you know, from your established corporate world, and you fit right in. I have a lot of friends that try to go to startups, and they can’t handle it, right? They need that corner office, assistant, the process, the procedures. When you’re hiring, you’re looking for people that can handle that. And it’s not a certain age or a certain specialty, it’s kind of within the person. And you described it so well. If you’re a founder, you know, for the founders listening, how do you hire for that. How do you build that team? Then that? Because that’s what you need. But you also need those people that have the finance background, the marketing background get, but that can do all the generalist things.
Casey Woo 11:46
That’s definitely half written in my book. Okay, one of the goals is, well, great, you’ve convinced me there’s a thing called scaler, right? Now tell me where to find them. My goal is to try to formalize the category and the persona more. Because right now it’s one of those, this sounds very weird, but it’s no different than any kind of personality, so narcissism, right? And I’m not, but that was the someone came out and defined. But in the end, it’s complex. You know,mine is called a scaler, right? So it’s just a different type of breed and there’s a personality. So one of the things to watch for is when you take a lot of these scalers together, the common personality, because I believe it’s a DNA. So let me back up. I think we are born a certain way, with a propensity to be better or worse at certain things. A hunting dog is better designed for hunting than sitting. Yes, you’ve seen the accountant breed. You’ve probably seen the enterprise sales breed. You’ve probably seen the narcissist CEO/founder breed. We all know what we’re talking about. The lawyer breed, right? The dentist conference. Why do they all kind of look alike? It’s because of the DNA. So if you take that same thing and replace it with scalers, scalers are impatient, generally, a very fast cycle speed. They abort very easily. They have a lot of neuro divergence, like me, which is like ADHD. And hence why horizontal work is very interesting, rather than one thing deep. You see, in early stage founders, a lot of neurodivergence. Elon Musk is a very pop culture one. What clearly is, you know, on the spectrum, and as a result, there’s a lot of business creativity. So you will, you can see pretty clearly someone who is very interested in building and solving problems versus maintaining and optimizing. So those are really two big different things. If they get very excited to jump into chaos, if they are comfortable with ambiguity, you have a pretty clear sign that they’re more early stage. The other way to think about it is scalers and early stage founders are business artists. So I never thought I was an artist. I can’t draw a stick figure. I can’t play, you know, any instrument. But I realized the biggest difference between corporate or large and small is degrees of freedom. The bigger a company gets, the less different things you can do, which is why Amazon creates a whole different division for startups that is outside of Amazon, so to speak, or Google X, because once the organization gets big, you can’t just innovate all sorts of stuff. They have a certain business model. Scalers don’t really like corporate or large because they love the ability to do anything. So at early stage, the degrees of freedom are like near infinite. What product line do you want to do? What pricing do you want to do? Do you want to do a website? Do you want to do go-to-market? We can change anything we want. We can pivot tomorrow. That is a dopamine. So when you’re in that scaler, early stage world, and you feel that dopamine, where you have a lot of impact, ownership and creative freedom, and you’re impatient, that suits really well for “we haven’t figured it out, we want to be disruptive” company.So how you find them is when you look at it that way, you can see pretty clearly someone’s personality, right? Of course, look at their resume. Scaler resumes commonly are all over the place because we have a thing where we don’t really like to do the same thing twice. Now, if you’re a career lawyer, generally you’re okay with doing the same thing twice or compound, right? That is a huge distinction, which is why we’re generally move horizontal than vertical. So you’ll see our you know, ones like, used to be a lawyer, then used to be in growth and used to like then started a side hustle. You see these unfocused-y type of things, but it’s really because they’re bored, curious, and want to challenge.
Kate 15:47
You describe that perfectly. I hope all the founders listening took note of that. I think you’re spot on, because I’ve also found these scalers, as you call them. They get energy, right from the chaos, from building, from starting early, and other people get stressed. They get smaller, they get worried. You do need to write that book. It’s spot on. It’s so true. Tell me, how is the Operators Guild supporting this? Like, how do you all bring it?
Casey Woo 16:18
We are literally the home for the scaler. Okay, so we are, like, any kind of professional organization. We have events. So we have in person events, and we have online forums. Online forums are what you would imagine, right? They’re asking for Q and A, connecting, helping each other. In person events are either social based or content based. So we had CFO Summit. We have OG Summit coming up for all operators. So that’s both programming and networking and socializing. Yeah, we have 120 events per year across 20 chapters. The 20 chapters are they follow tech density, so the largest are SF, New York, LA, then Toronto, Austin, and then on down the line. But yeah, OG is the safe space for some of the best modern tech operators in the world at early to mid stage.
Kate 17:09
That’s great. You must have some fascinating conferences and events, right? Because it sounds like you’re right at the forefront of building these incredible tech companies.
Casey Woo 17:18
It’s super fun because our programming is diverse, just like our problem set, right? So, once again, no offense to kind of old school CFO conferences, but if you come to our CFO Summit, you know, we’re talking about, obviously, AI transformation, you know, one of them was, you know, becoming a CEO, right? It’s not just budgeting. FP&A, right. To me, specialist vertical, which is great, but the modern operator at early stage is CFO plus, yes, they sit next to a COO. They are in CRO go-to-market meetings all the time. It is that cross pollination part, where what I like to say is, we’re business first function second.
Kate 18:01
That’s great, a great way of saying it. It makes it difficult, I think, for founders that are hiring to define the roles their people do. I mean, you must see that, right?
Casey Woo 18:12
Yeah. So depending on the stage, you know, you find the right scaler. Scalers have spikes, so we have disciplines. So mine is like Strategic Finance. Others are People and Culture, others are Analytics and Data. Others are fundraising. So we are generalists, but we have a spike. You know, there’s something a Navy SEAL has a sniper and explosive, right? There are Navy SEALs, but some are specialists in weapons, and some are specialists in explosives, right? So there’s that type of discipline orientation, but you also have another stage, right. The more generalists, the more horizontal someone is, generally the earlier. And then you move down that line, right? Someone that’s a little bit more of a mix of, you know, want to be more vertical, rather than the horizontal, seeing bigger scale, well, then they’re going to be fit for that.
Kate 18:58
Got it. That makes perfect sense. Thank you for walking us through it and then talk to us about FOG Ventures, because that’s that came out of Operators Guild?
Casey Woo 19:05
Yeah, all things OG came organically. A reverse product-market-fit. So I had a few friends in the venture capital world who reached out in 2020 and they said, Hey, can you take a look at this startup deal? And I said, that’s weird, I’m not an investor anymore. Why do you want me to look at this? They said, Oh, it’s a CFO operator tool. Oh, and they’re like, and you are the community of them. So if you like this, we might take a harder look, and the light bulb went off. So the one thing I learned doing public outing investing and when I was a hedge fund manager, it’s all about the customer. (That’s true.) So there’s not a single big company in the world that doesn’t have happy customers. So we are the customer. So to me, I made it simple, which is, we invest in the products we love in B2B. So we’re not consumer. So FOG does not invest in consumer or biotech or things that are way above our head. We invest in things that we use. So it’s a lot of B2B Tech, all stages. We are an open syndicate. So what’s really cool, is that when someone pitches to us, we’re now over 1000 of us, they get to be in front of 1000 decision makers. (Wow, that’s great). But also, these decision makers get to discover some of the best tools. So it’s a very, I think, differentiated way to fundraise and to support rather than just more institutional check.
Kate 20:35
Yeah. I love that. And so how are you all feeling about the market right now? You know, with AI dominating and like, what’s your take on it?
Casey Woo 20:46
I think the world is moving from from vertical to a horizontal operator. The first thing that AI replaces are specialist. Now, obviously the plumber is a specialist, so maybe physical is different than but if you look at what they first did was, you know, I think accounting very rule based. Now the word replace is kind of a tricky question. There’s an argument now that instead of replacing engineers, software engineers, software engineering is becoming even a bigger boom, because everyone’s needs an AI thing. And so the non-traditional, non-tech companies may want to hire someone that’s technical just to help them with AI agents, right? So there’s a whole thing of the word may not be replaced, but I think the world is moving more technical in general. Tech is just being embraced by, you know, everyone from the pizza shop to Facebook. So I think that is an accelerant. I think the office of the CFO in particular, and CEO, I become a lot more powerful because it used to be all the data was kept in product and engineering, right? We didn’t know how to code. We can’t get it. I don’t know what’s going on, right? Yeah, lines and like, what do you need? You know what customer information? And then we would just go back and crunch numbers on a spreadsheet. Now it’s flipped. The central organizations pull in everything, from the SaaS software to AI, it pulls in everything. But finance runs through everything. So a lot of times, if you had non financial data, that’s great. But what makes it really interesting is when you inject financial data. At the end of the day, a business is finance, yeah? Okay, without finance, there’s no business, right? So you marry the two together. And now I like to say the office of the CFO is the Office of the Chief Performance Officer. So we have all the information. We have sales, marketing, product. So now it all comes together: LTV/CAC, you know why customers are churning it all. It’s all tied to money, but we never got the data. Now we do. AI is perfect for horizontal, which is unstructured, homogeneous data together. I do think it is going to have to up everyone’s game. So the days of just crunching models, right? Same thing with accounting, same thing with anything rote or more junior, is not necessary anymore. So I think AI is gonna make a lot of people, hopefully, more strategic, more clever with horizontal tools. But I do think those who do not embrace AI may not have as many job options. So that is definitely something that is very obvious to me. And so what I mean by that is, if you think about it, Who does AI benefit the most right now? Business owners. Business owners generally, their largest cost is payroll. If you told them, I’m just gonna pick on accounting, your 100,000 or 80,000 or $50,000 bookkeeper can now be mostly replaced by accounting AI, that’s $50,000 to their bottom line. (Exactly.) Can you blame them, right? They’re not bad people, but if you were a business owner, you wouldn’t like, okay, I can save $50,000 pure margin, right? Okay, so guess who they keep? The accountant who really brings AI to bear? So I think if you’re an employee, there’s only two types: those who really leverage AI in their job and say, hey, you know, I’ll manage the accounting department, but in a very effective way. You’re great. I think you’ll have a job. But if you come doing it the old way and push up against No, no, you still need me, not that. Yeah, I think the $50,000 of profit. Are you gonna win?
Kate 24:37
Yeah, I think you’ve summed that up perfectly. I know, just on my team, when I inherited it, I had two people doing sales ops. They’re both gone. Now I’ve got an agent doing sales ops in the CRM, and I’ve got one employee who’s running agents and using AI and lots of tools. I think you’re just spot on in the way you walked us through it.
Casey Woo 24:57
I don’t know if it’s insightful, but it’s more like, Well, I’m just like, following the money, right? It’s like, okay, yeah, what are people doing? It’s an exciting time. I’m hopefully optimistic, but no, it’s also very scary. Yes, yes. Call it what it is. I’m old school too. Like, wait, how do I stay relevant? So the OG is one where we really, really try to push the bleeding edge, where, as an operator, you just, it’s all about evolving into the next operating, you know, cadence or stack. And I think for that, it’s very exciting. The content and everything has never been more interesting and more forward looking. Whereas before, I think we started getting a little comfortable with SaaS software, you know, right? And, like with anything, times change.
Kate 25:43
Yes, I think we all got comfortable there. This has been fascinating. I really enjoyed it. We always wrap up the show. You’ve shared a lot of great advice, but just any other advice you can share top of mind for the startup founders, listening right now?
Casey Woo 25:57
For startup founders, if you’re super early stage, you should definitely consider OG because if you think about what you do, you do everything. As you get bigger and hire scalers, please talk to me. There’s a lot of amazing, talented scalers who want to execute on a vision. Look to these types of people who are highly, highly leverageable and if you have a really, really interesting company that sells or product that sells to us, I’d love to hear from you. Love to support, both in talent or in customer intros or just getting a really cool product out there. But yeah, however, I can be helpful. Please let me know. And I’ve been there, and my professional mission is to help the builder.
Kate 26:37
I love that. I think that just helps the whole ecosystem when people give back to founders. Where can those listening go to find out more information about the Operators Guild and FOG Ventures.
Casey Woo 26:47
So Operators Guild is operators-guild.com. Feel out an application if you feel it’s a fit for you, and you can reach out to me directly on LinkedIn. And FOG is fog.ventures, not dot com, dot ventures. Any qualified operator will get in. Zero commitment to invest, but I highly recommend it, because it’s almost like a high end newsletter, where when you see the best deals, you’re actually reading about the future. So it’s really cool. And then if you’re interested in Angel investing, it’s a zero cost way to really get involved. Once again, zero commitment to invest. It’s really for the operators. That’s really cool.
Kate 27:22
Thank you so much, Casey for your time today. It was a fascinating conversation. You have to promise me you’ll come back after you write the book.
Casey Woo 27:30
That might be in 10 years, but yes. Writing a book is hard. (Yeah, I bet.) Yeah, I really enjoy it and enjoy helping.
Kate 27:37
Thank you. Thank you so much for your time.
Intro 27:40
You’ve been listening to Startup Success. To make sure you don’t miss out on future episodes, subscribe to the show in your favorite podcast player. Like what you hear? Tap the number of stars you think the show deserves in Apple Podcasts. For more tools and resources for your own startup success, check out burklandassociates.com. Thank you so much for listening. Until next time you.