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Casey Woo is the Founder and CEO of Operators Guild, an invite-only community for professionals in strategic finance and operations roles. He is also the General Partner and Founder of FOG Ventures. He is a seasoned, multi-stage operator, bringing over two decades of experience in investment banking advisory, public equity investing, high-growth operational and military leadership roles. His last role was the CFO of Landing, where he oversaw the company’s Finance, Legal and People operations. Prior to Landing, he served as the Global Head of Strategic Finance at WeWork.
Discussed in this Episode:
- The rise of the operator
- How to communicate with CFOs and cross-functional teams
- What matters most to every CEO and founder
- How to recruit the top operators
- Why funding no longer has the impact it once did
If you missed GTM 130, check it out here: Being CMO Under Mark Benioff of Salesforce and the Innovator’s Dilemma
Highlights:
08:33 Building effective CFO-CRO relationships.
18:13 The role of cross-functional communication.
26:59 The commoditization of funding.
32:53 The rise top operators and how to recruit them.
38:33 The commoditization of technology in the age of AI.
44:31 The power of community and in-person events.
Guest Speaker Links (Casey Woo):
- LinkedIn: https://www.linkedin.com/in/caseywoo/
Host Speaker Links (Scott Barker):
- LinkedIn: https://www.linkedin.com/in/ssbarker/
- Newsletter: thegtmnewsletter.substack.com/
Where to find GTMnow (GTMfund’s media brand):
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- Twitter/X: https://x.com/GTMnow_
- YouTube: https://www.youtube.com/@GTM_now
- The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/
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The GTM Podcast
The GTM Podcast is a weekly podcast hosted by Scott Barker, GTMfund Partner, featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
GTM 132 Episode Transcript
Scott Barker: Hello. And welcome back to the GTM podcast. You’ve got your host, Scott Barker, fresh off of some much needed out of office time. Just got back from Mexico city. And my guest Casey Woo is actually flying down to Mexico city like next week. Is that right?
Casey Woo: That’s right. I’m very excited.
Scott Barker: I love that man. I love that. So you guys are open up a new chapter down there.
Casey Woo: That’s right. Yeah. So my company Operators Guild or the community is launching its 21st chapter. Uh, Mexico City.
Scott Barker: Hell
Casey Woo: it’s, it’s a, definitely a very up and coming tech ecosystem out there that I’m excited to help invest in.
Scott Barker: it is. It really is. [00:05:00] I always enjoy my time down here. And it’s it seems to be a beacon for a lot of, you know, really talented folks. Um, so anyway, I’ve been super excited to have this conversation. It’s it’s bounced around a little bit on the calendar. So I’m excited to nail you down. And, you know, for our listeners, I’ll do a quick bio.
So Casey Woo is a seasoned multi stage operator, brings over two decades of experience, uh, in investment banking, public equity, investing, high growth, operational, and military leadership experience. And his last role, um, was the CFO at landing, where he oversaw the company’s finance, legal and people operations.
And then prior to that, he served as the global head of strategic finance at WeWork. Um, which would have been a crazy, crazy run. So excited to get into that a little bit. Um, but now he oversees a thousand CEOs, COOs, and CFOs as the founder of Operators Guild. Uh, if you’re not familiar, [00:06:00] it is an invite only community for professionals in strategic finance and operations roles.
So not unlike GTM Fund and GTM Now, just another leg of the, the stool. And, uh, I don’t usually go into. Uh, people’s education background, but, uh, did graduate from Harvard and West point, which I think is definitely worth, worth shouting out. Um, but man, I, I do feel like we kind of clicked on our, our very first meeting and that’s why I’ve been excited to host you on this podcast.
I think we just see this, the, the world in a very similar light and, you know, typically we bring on revenue leaders, founders, but as I said, you know. That is one leg of the stool, and it’s important to hear from other voices from time to time. And we’ve had conversations in the past where it’s like, you’ve got to build division, you’ve got to sell division, and then you’ve got to scale division.
And scaling the vision [00:07:00] requires finance, legal, people, ops, and some of these maybe unsexy roles that are absolutely critical. And that’s been your world and maybe a good place to start is, you know, pulling from your time at, at landing and, and we work. What did you wish more CROs, VPs of sales, your counterparts on the revenue side knew about how to communicate?
With you, the CFO and kind of the, the finance and ops team.
Casey Woo: Yeah, I, I have a thing where when I start a new CFO role, I sit down the entire team and I think one, one of the most important things for leadership is setting the mindset and the, and the tone. It’s no different than, you know, the Trump administration has a certain tone or the Biden administration, whatever it is, it’s a mini administration where it’s not about the, just the work being done, but it’s how you act, how you [00:08:00] behave, uh, what your policies are.
Uh, for me, I say, Hey, CFO organizations or offices can basically be broken into two different types. One is the enforcer. You’ve heard Dr. No, the police force, et cetera, which is fear, fear driven, whip driven, and of course the opposite, right? The enabler, the empower, the partner. I say it’s customer service. Hey everyone. If you thought you were like the police person with power over, no. You are the customer service representative for our CRO, our CTO. We don’t, our customers aren’t the customers of the company, by the way. Our customers are all the employees, and I need you to have that mentality. And by the way, I’m going to answer your question, which is first of all, that CFO needs to set that tone.
If they set the tone as an enforcer, it’s going to be naturally really hard for CRO to approach. Cause you’re not setting up [00:09:00] trust. If hopefully your CFO is doing enabler partnership, rather than I’m going to call you out on watching you, that makes it pretty easy for, and the invite for all the other execs, especially obviously go to market and tech, I’m sorry, engineering to bring them into the fold.
So number one is the modern CFO wants to be, and should be deeply integrated into go to market and product. The days of the, I’m going to, I’m an accounting FPNA. I do the budget only those days are over. That is so table stakes. If you want to be a good CFO, you need to know what the hell’s going on in that go to market meetings, at least at a high level.
So I think it’s sensing that that’s an exec that wants that and then teaching them, bringing them in saying things like, Hey, would you want to be part of our weekly standup or, you know, come, come as you [00:10:00] wish, but it’s really this partnership. Quiver. Um, the second is transparency. It’s very simple, right?
If you’re surprising the CFO every time, that’s not building trust. That’s clearly like, I can’t trust everything the CRO says. If it’s like, listen, advanced notice, we’re going to have a hole in revenue here. Our pipeline is getting weak here. I just want to let you know. my God, that is like, and so eventually what happens is you build a partnership where it’s, it’s happened a lot of times where, I mean, to be quite honest, the CFO helps you make you look good, or he reaches the skids for the CEO to take a, to take the hit for you.
Um, but the more notice and the more advanced as you have, there’s a lot of information CFO has that can help you, especially when it comes to political stuff, right? Let’s call it what it is. Humans are political, right? So what you don’t want to do is start. And this is what happened. I can’t name the company, but where the VP of sales.[00:11:00]
Was literally treating me like an outside entity and this is my territory stay out of it You know, it’s kind of an old school type of mentality. He made a lot of enemies I didn’t trust what he was doing a lot of it was hands off get out of my get out of my kitchen That doesn’t do good for anyone And it gets reported up right where so I can’t get anything from this person, etc That’s just gonna be whittling away.
So it really is a long way of saying Bring them into the fold partnership helped me Uh, and from there you’ll be surprised, uh, they can really help soften the blow, you know? And look, I get it. CFOs understand that marketing and sales want to look good. We have a joke. It’s like, there’s a metrics they share us and the metrics they create. It’s magical. What go to market creates for metrics. It’s all the stuff that has really good output, but work together to find a [00:12:00] real one. Because if you do those things, people know, and then your reputation immediately. Is someone that’s self serving. So that’s really the biggest advice is don’t be self serving and just be dead honest.
And you’re getting a lot of people who will help you succeed and want you to succeed versus watching when you trip up and calling you out, like, okay, we’re gonna call them out. What kind of metric is that? It’s just, it’s just a very, very negative.
Scott Barker: Yeah. Yeah. I think that’s all, that’s all great stuff. If, if I’m a CRO and I’m listening to this, I’m heading up sales and I feel like I have. A doctor, no, as my counterpart, as, as you said it, like a fear driven, uh, CFO and, you know, I’m, I’m worried to go to them. There’s always battles when I go to them for things.
So anything I can do to address that and do they even be, do they even want to play that role? Are they sometimes forced to play that role?
Casey Woo:[00:13:00] That’s such a good question. I mean, of course it’s case by case. Um, I think there’s, if I were to once again, break it up into two categories, there are the, um, people that are going to be hard asses and they’re just going to be hard asses like they’re, they, they, they have no interest and that’s just who they are. That’s where they’re from. Then I think you spend more time being professionally transparent and delivering the information real time and you don’t need to be partners with them.
It’s just, I got a job to do. You know, just straight facts here. The others that you can tell are want to be included. You know, they might be, you have to read the room. They might be new. They want to show the CEO they’re delivering value. If it’s the second one, you help them look good, right? It’s what it is.
It’s, it’s helping people succeed. So you find out very quickly. So [00:14:00] I ask everyone, when you sit down with your stakeholder, figure out, write down on a piece of paper. What’s their pain point? What do they care about? Like, what is it? Is it commissions? Is it their issues with a team, you know? And then the second is what you can help with them immediately.
Is there anything going on right now that can help you, right? So you can reverse it from a CRO to CFO. Hey, anything, it could be, I don’t have a lot of visibility in XYZ. Immediately, my customer service come back two, three days later and say, Hey, remember that thing you said? I put some work with my team on to be able to help you get more visibility. Right. You just start to help someone solve their problem and that begins the erosion of the no.
Scott Barker: Mm
Casey Woo: It’s, it’s a classic. Just build trust. Is this person for me or against me? That’s exactly what’s happening in the first meeting for me or against me. Trust them or cannot trust them. And you have to repeatedly do [00:15:00] things of pure altruistic.
Like I’m going to help you. Like any relationship, then all of a sudden those, like it softens from there, go back, invite them to the meeting, but give them information and Intel almost like before anyone else knows.
Scott Barker: hmm. Mm
Casey Woo: They’re in the, they’re in the, in their club. Um, and lastly, CFOs don’t want to get surprised because their job is to look out, their job is to forecast.
So whatever you can do to ease their stress, budget surprises, misses, surprises, they need to be the first to know because that’s how they look good. To their boss, right? So or looping them on big decisions, right? It’s all very first principles of relationships that people forget. But you can break someone down from a no to this.
And then at the very end, it’s like, listen, I feel like we have this like police relationship. You know, I [00:16:00] want to bring you in the fold more, you know, we should be partners. It’s, it’s going to be better for us that way. Right. There’s, there’s, there’s always just a straight up call them out.
Scott Barker: Mm hmm.
Casey Woo: Uh, and you’ll be surprised.
You’d be surprised. Are the, they’re like, wow,
Scott Barker: What I, what I find super interesting is, you know, you said two questions there, you know, what’s their pain point and what do they care about? And, you know, although you have your CFO lens on starting to, you know, sound a lot like the CROs that we have on this, this podcast, because they’re, they’re doing essentially the same thing, except their buyer is external and your buyer is internal.
And I think if, if people can really internalize that and understand that. They can then start speaking the same
Casey Woo: never thought about it. You take the superpowers that are natural to a sales leader. What are sales leaders? They’re really good relationship people. Especially at the enterprise level, they’re trained relationship people. Just turn it inside. And again, you’re [00:17:00] right. You call it something really good because the stereotypical finance is very analytical, very execution based.
They’re kind of forgetting about the relationship. And I think that’s pretty much what I’m sharing with my team is relationship is the most important. I kind of say with your CEO, you could be the smartest CFO in the world, the best. Everything’s going to come down to your relationship with the CEO. I’ve seen people with the most extremely good relationships with their CEO and they suck. It’s all good. It’s all good for a long time. And some of the best CFOs who just cannot build a rapport, they’re out.
Scott Barker: hmm.
Casey Woo: more important? Extreme competency or, or EQ? It’s EQ. All the time.
Scott Barker: Thank you. How, how did you, you learn that? I think that’s something I really appreciate about you is you’ve been able to grow your career and, and, you know, you can have the talk with a finance professional, with a legal professional. You can get in the weeds with [00:18:00] me on go to market, on sales and, and marketing.
How did you learn to speak the Multilanguages when, of business, when many usually go really deep or niche on maybe one or two.
Casey Woo: Yeah, this is um, the fun topic we had, we had a conversation about. And I think that’s what you’re referencing, which is, um, So at the Operators Guild, what I’ve learned is, Who is the operators guild? You know, we are the we don’t code and we don’t sell, right? We’re the biz op strategy. And when you think about that role, it’s cross functional.
It has to be. I mean, by definition, it’s it’s it’s not an organ of the body. It’s the arteries, right? So the arteries run through the whole thing as compared to any one thing. So we are the nervous system arteries. If you want to use that analogy, which means we have to talk to and interact with every organ in the body.
Which is a very different role than what the heart does. The heart doesn’t necessarily talk to the liver. I’m getting a little out there, but it’s in charge of its function. And it needs to just beat the heart, right? Ours is taking care of [00:19:00] everyone. across every organ is what we do. Okay.
What happened was, I had 10 years in Wall Street. And I felt like a fish in water there. I mean, I wasn’t like fulfilled, which is why I left. But, you know, these are my finance bros or gals. You know, I just felt very at home. Then I joined a 10 person startup. And for some reason When I was communicating or trying to sell something or, you know, convince someone of something, it went from very easy in Wall Street to very difficult. And yet, everyone I’m working with in the startup is smart, English fluency, and then I quickly learn as a rookie operator. The difference between a rookie operator and a senior operator is Google Translate. So the analogy I use, in Wall Street there’s only two zoo animals. I’m going to make them up, a rhino and a bear.
A rhino is the investing team. The bear is the assistance. There’s only two people at a hedge fund. It’s the investors and the assistance. That’s it. [00:20:00] Kind of like VC. So when you’re speaking to another, in this case, what’d I say, rhino, whatever I called it,
like you’re just speaking and the rhino speak. And then you learn one language called the bears and you know how you interact with the assistance.
Great. In startups, it’s a goddamn zoo. It is. The CRO is a different animal than the marketing person. The narcissist CEO is a different animal than the, um, paranoid accountant. So all of a sudden, as I’ve progressed through my career, you start to realize that you’re actually speaking. Eight languages at a startup. Marketing people talk budget. That’s, that’s, that’s what they want to talk about, right? That’s how they they’re focused on the budget, right? Engineering likes to talk about technology, new technologies and impact. So a good example I had was I remember trying to explain to the CTO that [00:21:00] we needed like a process.
Oh, sorry. We needed to. Um, get our cogs down and most of our cogs hosting costs, which is under his content. So explaining gross margin to him, the cogs and the costs, whatever. And you could see he’s very smart. Like I said, English fluent, didn’t understand. I brought in the founder who was half engineer and half business.
I spoke to him. I said, this is what I’m saying. And he turns over to him and says. Oh, what he’s saying is, um, you know, those hosting costs that we have. Yeah. So basically every compute point or whatever that we can reduce it, you get another engineer and he’s like, got it. I’m on it. And that’s when I learned, I’m speaking French and this guy is, is Russian.
That’s going to be a really, really hard time if you really thought about all the languages. So over time, I’m whatever you call octolingual and you collect languages [00:22:00] and it is amazing once you have their language, but think about budgeting. So the other thing I realized, I sit in a room with a salesperson, that’s a completely different budgeting conversation than tech, than product, right?
So anyhow, so as you see very quickly, any cross functional role, it’s actually a whole bunch of different breeds talking to each other. And that’s why it’s very, that’s why you get into fights. That’s why you get like the product person battling the CRO. Different countries and different languages. Um, so anyways, that’s what I call Google Translate.
The faster you can actually speak their actual language rather than English, the faster you can pass any bill through Congress.
Scott Barker: Yeah. For yourself, like your initiatives, and then also you can act as the conduit or the translator between all the other, you know, organs. And so even if they don’t know the language of the heart or the liver, you’re the one that can,
Casey Woo: That’s right. The
Scott Barker: now mixing analogies, but I
Casey Woo: no, no, but the CEO and CFO are cross functional, [00:23:00] they’re switching one on one meetings with completely different species. Their job is to translate it all. That’s actually what’s happening. And then to balance the whole, you know, biosphere. Um, but you need all the different animals to use analogy.
Everyone has a very powerful specialty, but to work together, that’s language and communication.
Scott Barker: Yeah.
Casey Woo: That’s why budgets are so hard to do.
Scott Barker: Yeah. Cause there’s a large part is, is relationship management, storytelling and translating when it seems like it’s numbers driven. Yeah, yeah,
Casey Woo: Yeah. Why can’t I get my budget? And it’s just balancing all dependencies. Um, but you got to speak their language of why they can’t, it’s no different than any relationship. We tell a kid why they can’t have something. There’s ways of telling them that make them understand as ways of telling them that piss them off.
Scott Barker: yeah, yeah, I love it. I love it. Um, so I want to shift gears a little bit or actually go back to something we talked about. So we have these. You know, broadly main [00:24:00] pillars of, of company growth, you know, you got to build, you got to sell, you got to scale. And then, you know, in, in the past, there’s really been this fourth pillar, uh, to build a large software AI company, which was capital.
And I think you and I, and this is based on some past conversations we have had, uh, are seeing some shifts in that last bucket, uh, partly because it is. What we do, um, and with what you’re seeing at operators guild, as well as fog ventures, uh, which is kind of a, a venture arm of operators guild and what we’re seeing a GTM fund in our community where people can actually now get access to that 4th pillar capital.
From folks that have experience within the other 3 main pillars and, you know, I think you’ve kind of coined it as this idea of the rise of the operator and would love to just sort of geek out on what that means to you a little bit. [00:25:00] And what you’re
Casey Woo: Yeah. Um, it’s part of, you know, it’s part of this, um, book I’m trying to write because I, I’ve, I’ve, I’ve been in it long enough now to see what’s happening. Um, I’ve sat on many different seats as a hedge fund manager on the investing side. Um, then I became an operator and then on, on the BC side. So I’ve, I kind of circulated all, all, and a banker as an advisor, all CEOs and founders want three things. Number one is money. Number two is customers, and number three is talent. Now, you know, I think probably customers is number one by far, but the point is all CEOs and founders. I think everyone needs to remember this. If you want to get the attention of a founder or CEO, it’s money, customers or talent. Customers almost all day long, you know, money is when they’re looking for it. Talent, mostly all day long, unless they’re downsizing. [00:26:00] Let’s go through each of them. Number one, money. It used to be, it was 10 VCs on Sand Hill Road and they held the special money and it was hard. It was a big deal. Hey, no offense.
Now it’s money is plentiful. I mean, you can do charts on how much money, how many VCs are competing. The head, the big hedge funds are tossing in. Bezos has his own fund. You can get money. Money’s becoming more of a commodity. The other reason why is so many founders have gone through these cycles. In the beginning, it was like worshiping the investor because they’re the boss, so to speak.
And then they realized, you know, what’s really hard is building this daily in. Day in, day out. And that is my assistant, that is my associate, that is my talent around me. Money is very important. Don’t get me wrong. But I always say, I can give you 10 million to sit on the sidewalk. Doesn’t do anything. It just sits on the sidewalk.
It needs to get converted [00:27:00] into talent and customer. Okay. So if you look at visually money, customers, talent in your head, and number one is pretty much almost a commodity. Like you got an idea, someone will fund it. The acquisition costs of what is finite, no matter how much money you raise, there’s the number of customer set and the number of talent are finite. We’ll do the equation. The cost of acquiring a customer and the cost of acquiring a talent is now skyrocketing. You have way more money going after the same problem. The number of times you’ve seen a space that’s crowded is every day. Okay, so now you put it all together. You go to a second time founder and you can offer him money or offer him customers or talent.
What do you think he’s going to pick? I’ve got the money. You know what’s really hard and my other competitors going after? Customers and talent. Now, of course, it’s always been customers and [00:28:00] talent, but it used to be money wasn’t was, was like on the mind. So now think about operators in fog. We are both customers.
And talent. We buy B2B products all day long. It’s like a mom’s group controls 80 percent of the household budget. Okay. At the same time, we’re the talent. We’re the one that sits next to you 60 hours a week building with you. Cause it doesn’t, the money doesn’t build itself. So the rise of the operators, because startups have gone from a hobby to a profession. It’s the NFL. There’s so many people trying to get drafted. You know, but the competition’s up. So it really is very talented operators are needed to win this battle. Now it’s not good enough to have a product and sell it. That’s where the scalers come in, right? It’s the third leg is needed to get the edge before.
You just needed one edge to edge. Now you need all three [00:29:00] at any world class level. All things got to be hitting on all cylinders and that’s what’s happening.
Scott Barker: I love how simply, simply you put that. And it’s, it’s so true. Literally, those are the only things founders care about money, customers, talent, and they’ll take customers and talent over money. Cause money was just a, a conduit to get customers
Casey Woo: It’s a fire starter. Yeah. Oh, by the way, just to add to that, I tell people, you got customers, you got Sequoia. Guarantee you, if you keep loading up customers, Sequoia is going to be there, right? Or you can try to go after Sequoia first. Okay. It’s a little bit harder.
Scott Barker: Yeah.
Casey Woo: Customers will unlock, customers unlock talent.
You got revenue, people want to work for you. So you just got to simplify it. Um, and then last thing I would say is there’s only two ways a company gets money, an investor or a customer. You want it to be the second, the biggest companies in the world, the ratio of [00:30:00] how much money they took in versus how much money they took in from a customer, right?
It’s dwarfed. Um, that’s it. It’s that simple. Get more money from customers, not investors. You win.
Scott Barker: Man, this is, this is good stuff and exactly how obviously we see, see the world that at GTM fund and we’ve seen it play out over the last, you know, four years. And, you know, the other things I think that are, you know, you said this, it’s, these are in turn, like, have always been true, but now with, you know, I think we’re really hitting.
At least on the go to market side, like the ability to get customers is harder than ever before. Everything is more saturated. Everything’s more competitive. We’re all using the same best practices, you know, it’s getting harder and harder. So what unfair advantage do you have? Who can unlock little doors?
Like those things really matter more than ever. And then on the flip side is I think the future of. [00:31:00] Even really large, successful organizations, there’s going to be less talent, but that talent is going to be the top 1%. So we are all fighting over the same talent because that talent is going to be augmented by AI and these people will be basically superhuman and able to, you know, just do incredible amounts of things while they’re, they’re being augmented
Casey Woo: We are no different than a professional sports team. We are athletes and we have different skill sets and you got to assemble the right team to win championships. I know that’s an overused analogy, but when you’re at a championship level, you’re competing with the money that can buy LeBron can buy everyone. It’s about the potency of the talent and putting it together. Right. And it’s no different when you think about a team, but because the stakes are so much higher and everyone’s got a lot of money, their salary caps are all gone. The talent is very real. And [00:32:00] then now we’ve gone through enough cycles where there’s a difference between world class Olympic level college level high school level because there’s enough of us now and it is starting to stratify.
Scott Barker: quickly. I don’t want to spend too much time on this, but I, I. I know you’ve recruited incredible people into this community. You’ve included incredible people to work for you in multiple different industries. Um, and now that it is more important than ever. And I think every day that I do this, I realized how important that talent is.
It’s almost everything. Uh, and we’re going through a hiring cycle for a new associate right now. And it’s just like the bar has to be, you have to beat the bat, like. The best in the world. Like, yeah, I have to just be wow. And if not, then let’s hold. Um, and how, how have you been able to recruit top one, 0. 1 percent talent in, in the past and now
Casey Woo:[00:33:00] What I, what I try to write about is the breed I look at, I call it special forces of business. It’s like the rise, it’s the creation of like Navy SEALs essentially is what’s happening. Every profession has a persona. You think it’s a surprise that when you go to an accounting conference they all look the same?
You think it’s a surprise you go to a sales conference and they all kind of look the same? Or a legal conference? Operators. You, me, like we may well time founders. We all look the same in a different way. And what that is, is you have to understand what makes them tick. That’s how you recruit someone. What makes an operator tick?
They want to win. So, so, so how do you win? The one of the most exciting things for an operator is working with badasses. They can learn or they can trust the person to their left or right. It’s no different than Navy SEALs respect each other. Okay, so the first thing is who am I working with? [00:34:00] Do I want to learn from this person?
Are they going to make me better? The second, if you’re talking about early stage is autonomy. We like impact. We don’t like things that are thankless is what we call it. We do something in a big organization and no one cares. And no, there’s like a meaning to what we do. There’s an impact we can make, whether it’s at a two person company or 20 percent or 2000, it doesn’t matter. got to allow them a seat of impact. So really good people around them, seat of impact. And of course they got to feel like they’re going to win whatever they’re on. Who doesn’t want, who doesn’t want to win? Um, they’re generally risk takers, you know, they’re very optimistic. So they want to see a winning team.
And yeah, and then the other thing is, you know, everyone at the different stages is optimizing for a different thing. You got to learn what that is. Some people are optimizing for money. Some people have never led a team, so they want to lead a team. Some people were really pissed about not being [00:35:00] respected in their last thing.
They’re looking for respect. Make sure you give that to them. It’s no, it’s, it’s literally sales psychology, which you can teach me better than anyone is just, what do they care about? What are their pain points? What are they value? And you can quickly tell what they value, excites them, what energizes them.
So that’s, but you gotta be a winning team or give them
something.
Scott Barker: and like summarize that the, the, the, the non negotiables are, you know, they need to be someone who wants to. Work with other badasses. They want to have an impact. They want to win. They are a risk taker Optimism. I like that one Because it is very true. You know, they’re if you’re too pessimistic, you can’t you can’t play this game You’re just slowing us down at this point
Casey Woo: yeah, yeah,
yeah.
Scott Barker: be wrong But let us fail and let us feel quicker and then we can we can figure it out and then But I heard the next [00:36:00] thing is then you figure out are they have to respect money?
Or leadership or like building a new skill set. Um, and then you can, you can go after them. I like it, man. Um,
Casey Woo: We’re, we’re
adrenaline junkies. You got to find out what’s, what thing gets our adrenaline going and then just give it to them.
Scott Barker: Yeah. Love it. Love it. All right, man. Uh, this has been awesome. Uh, I really appreciate you hanging out, uh, today and I got a final two questions, uh, for you and, you know, I always keep them the same.
They are intentionally vague. You can take them anywhere you want. Um, but the first question is. What’s one widely held belief that founders or executives believe to be true that you think is bullshit or no longer serving us?
Casey Woo: Yeah. I’m going to go with the, um, not the bullshit, but the no longer serving us, which is basically the evolution of the startup, um, at a high [00:37:00] level. When you early days of tech, it was you needed a good engineer to build a product, then it moved to you have a good product. You really need a good salesperson or sales team to sell it, right?
So it kept evolving of what it took before you have a good product. There’s no competition. It’s fine. Then it became Oh, I have a good sales team. Then I beat anyone with just a good product. And then it was so basically technology was winning. Better tech, right? This thing called sass came out and just crushed everyone.
What is no longer serving us is, I think we’re oddly moving to a world where, dare I say it, with AI, etc. Tech, having good tech and having a really good, yeah, having good tech and a good solution is commoditized. That’s [00:38:00] not how you’re going to win. You better have that out the gates. You better have a good engineer.
You better have whatever, because AI is like a nuclear weapon that opened an API up. Everyone’s got nukes. So if you think you’re more powerful and better technology in the next person, not enough, I think the new weapons of differentiation or even more so distribution, the ability to sell the product, because so many solutions is.
The only thing that matters is who pays for it. Okay, so you might have existing distribution, like NetSuite has existing distribution. That’s pretty powerful now when you layer AI in, right? Even though their technology is old, right? So distribution is now becoming even more critical. The better your hunter, the more you get the edge and then you, because it’s so crowded.
But the other one’s velocity. I kind of wrote a, I wrote a post that, you know, got controversial, but you know, it [00:39:00] was, I fired for effect, which is the 18 month fundraise cycle is dead. The true story. There was a VC hearing a pitch on Friday. Shout on the idea was like, you know, you should be doing this or that on Monday.
They came back. The entire deck was changed and they had that product for whatever he was talking about. I call it research and product. It’s not research and development anymore. Development has this idea that you’re developing. Give me six months. Give me nine months. We show you something. We’re talking like within hours.
I’ve seen product changes. Zuckerberg talks about it. They’re like, why are you so confident you’re going to win velocity? Whatever we’re wrong about. We’ll just move so fast there. We’re going to beat you. Notice he’s
not even talking
Scott Barker: we have a built in distribution advantage. So we can just
Casey Woo: He’s not even talking about my technology is, yeah. Better than yours. So I think that commoditization of technology, funny enough. Now don’t get me wrong. [00:40:00] AI is an innovation, like a no other, but it’s being, think about it. It’s being given to everyone for 20 bucks a month, air quote, all the edges that the smaller countries did not have over the superpowers.
They all have nukes to use that example. not the only five countries in the world to have it. Everyone has it. The small guys have it. Now it’s going to be distribute and it’s the speed. So these like small teams. Are catching up so fast because the big guys can’t the velocity. So anyways, that I think is a changing construct.
Scott Barker: speak in my language. I mean, we, I think we covered two, two things there through this project is. We talked about this one, which is tech is becoming a commodity and capital becoming a commodity. So if those two things are becoming true around the same time, then it makes velocity and distribution, you know, 10 X, uh, more powerful of a, a moat, um, which I kind of.
Just [00:41:00] kind of fucking exciting. It’s just like game on, you know, it’s like, it’s, it gets me kind of fired up. It’s like everyone it’s to your analogy of like, you know, we’ve got, you know, people in the NFL and people just starting out and people on the college, it’s kind of like everyone can get in the game now.
But now it’s like, we’ll, we’ll see who knows how to actually execute and, and play the game, you
Casey Woo: To use that analogy, I was watching like MMA fighting or NFL and you talk to him like, wow, like how was he? And they got beat. They’re like, man, his speed. His strength. So when you talk to play football, I did not, but they’re like, the speed difference is what they talk about. Like, what’s the difference between college and NFL?
They’re like the speed of reaction in the pocket, you know, whatever it was. It’s five seconds in college. It’s three seconds. And that’s actually what’s happening to us. You think you’re fast. There’s other engineers faster than you. And that’s who wins Superbowls. [00:42:00] It goes back to the 1 percent talent. It all like ties back.
Speed gets difficult. It really separates world class from okay, from whatever, and the talent game is now professionalized.
Scott Barker: Yeah. And it compounds, can compounds quickly. Uh, which is, which is especially, yeah, you layer on AI, which also compounds quickly. You will see teams just absolutely. Rocket ahead
Casey Woo: Yeah, for the speed.
Scott Barker: I think is kind of needed. Everything’s murky. It’s very competitive. I think I think we’re going to see more more breakouts, uh, this year, which will be exciting.
All right, um, final question for you, um, you know, everyone, you know, you listen to a podcast, right? Give me some silver bullet. What can I use right now? That that might help me? Uh, You know, move the needle in my business. Um, what’s one tactic or strategy that’s working right now? Um, either for any of the companies you’ve invested in or operators guild itself.
Casey Woo: Yeah, I’ll probably cheat and talk about Operator’s Guild because it’s what I know best, but also [00:43:00] it really, so it’s less for a software company, so to speak, um, but I think it appeals to almost anyone that hopefully is listening. When you think of AI and you think of technology and what’s happening in the world, I’m long community.
Like if community was a stock by what happens to all this technology, in theory, it gives us more time, right? It gets more time for insights, more time for family, more time to do not email. Now, if we do it all wrong, we just get more busy with stuff that, you know, it doesn’t do anything right. But if we do it right, machines and technology are going to give us more time and People are lonely. Social media, all the stuff you hear at COVID. What, what is the silver bullet is you must realize whoever I speak to, there’s some form of loneliness where they [00:44:00] really want to connect with someone. In life, that could be meeting another’s founder. There’s a loneliness in people’s lives and the events we hold.
We just took a huge survey. There’s a lot of good things we do. Number one, in person events. Number one, meeting people in relationships. I think it’s been forgotten. Like the bring back of the dinner party. I am long all in person events. You know what? The one thing AI is not going to affect for a very long time.
Flesh in person, grab a drink. Everything else is going to, or plumbers, though they’re, they’re good too, which is why Elon’s doing robotics and stuff. It’s like physical world. Like, you know, so. There’s a lot of like tactics and stuff, and then there’s just like making time for relationships and going to events.
And if you’re in the game of events, by the way, so if you’re selling events could work. If it works for your thing, get people together with other people and [00:45:00] then sell your thing. Cause there’s too much of all the other non event stuff in their life. It’s just so much you shut it off or it’s just not additive.
But events are hard now because we don’t need to travel anymore. We don’t need a commuter anymore. So getting someone out of their seat to drive and park and go somewhere is hard. But I think that’s where if you set it up for them and make it easy, like the Mexico City event, that I’m very, very long.
Scott Barker: Yeah. I mean, this is what I said at the beginning. We see the world in the same, the same light, uh, community will continue to grow in. In importance and, you know, in person events, you know, same with, you know, GTM now and GTM fund. Everyone always says like, it’s actually just like the dinners are like one of my favorite things.
Getting together with 40 people who are like minded going through the same things. They actually see me. Um, it’s so, it’s huge. And, uh, [00:46:00] you know, it’s, it’s about this idea of actually creating connection in a non commercial environment. And what’s funny is when you do that people want to Do commercial business with you, you know, at the end of the day, people that’s, it’s almost that simple.
Um, but Casey, this has been awesome, man. I am very excited to read your book when you, uh, when you finish that one. Um, and good luck on your Mexico city event. Uh, if people want to follow along with you, check out operators guilds. Uh, what’s the best way to do so
Casey Woo: Yeah, you can find me on LinkedIn. Follow me. But uh, so it’s operators dash. guild. com. Uh, any elite badass operators that don’t code or sell per se, send them our way. Uh, but yeah, that’s the easiest way to do it. Uh, reach out, apply if you think you’re, you know, you’re a fit, uh, or just reach out to me and DM me, um, and I’ll get right back to you.
Scott Barker: rock and roll. And to all our listeners, you know, I [00:47:00] say it every week, uh, listening is one thing, executing something totally different. Hopefully we gave you some ideas, tips, strategies to bring into your organization and, uh, we will see you all next week.
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