With Scott Orn

A Startup Podcast by Kruze Consulting

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Scott Orn

Scott Orn, CFA

Operators Guild lets ops professionals share ideas and best practices

Posted on: 04/07/2024

Casey Woo

Casey Woo

Founder, Managing Member - Operators Guild

Casey Woo of Operators Guild - Podcast Summary

Operators Guild cultivates a community of finance and operations professionals who help each other navigate the issues involved in scaling companies, and develop professional networks.

Casey Woo of Operators Guild - Podcast Transcript

Healy: Hey, this is Healy Jones, VP of Financial Strategy here at Kruze Consulting, andI want to say thanks to our podcast sponsor, ARC. At Kruze, we’ve got a number of clients successfully using ARC to manage their deposits, payments, access financing, all in one place. One of the things that ARC provides that’s really great is over a quarter of a million dollars in FDIC coverage. Their insurance program goes beyond the standard limit and it secures up to five and a quarter million dollars. So, startups that have even more cash than that can go and access treasury solutions to provide yield and safety. If you’re a startup looking for a secure financial solution that can help you scale, please check out our sponsor ARC at
Scott: Welcome to Founders and Friends podcast with Scott Orn, Kruze Consulting, and today my very special guest is Casey Woo of Operators Guild. Welcome Casey.
Casey: Thanks, Scott. Glad to be here.
Scott: Oh, my pleasure. I’ve been in Operators Guild for four or five years. Love the community. It’s COOs, CFOs, finance nerds. Maybe tell everyone how, and you’re one of the founders, maybe tell everyone how you got it going and what it’s all about.
Casey: Yeah, happy to. I have a 20-year work history. My first 10 years, I did the very classic Wall Street investment banking, go get a private equity hedge fund job. I did hedge funds, and then retire. Except, during that, I realized I love to build. It’s in hindsight. So, I left Wall Street. I moved from Silicon Alley, where I had my first startup, to Silicon Valley, because I said I got to learn this tech thing, and it really wasn’t happening 12 years ago in New York. Now, it’s actually really starting to fire up. It’s just good to see.
Scott: Yeah.
Casey: For later, we can talk about, I think the manifesto I’m working on. But basically, I learned the hard way that finance, HR, legal, IT, ops, things that are not really sexy, called engineering or sales, you’re climbing uphill here. I switched from… Finance is shit in New York. It is shit in San Francisco. Once again, I’m being a little facetious, but my point is, it’s not as cool. They say, “You don’t have a CPA, so you don’t qualify for finance.” I’m like, what? I don’t qualify? So, I learned a lot. That led me to getting really lonely. That led me to joining a lot of CFO groups and a lot of COO groups. For later, I’ll tell you why it didn’t work for me. I reverse engineered a mom and dad’s club with five rules of the things I preferred, or I’d say one minus others. I may be called the founder, but I think I’m just member number one. I think I created an organization, looking back, that I wanted, but I think a lot of other people wanted. That nine in April, 2014, met up. Amazing CFOs, CEOs, I’d all call us misfits, or same issue. Can’t describe what we do.
Scott: Did you say April 2014? So, it’s almost 10 years old? Wow, that’s crazy. Amazing.
Casey: We’re approaching 10-year anniversary.
Scott: Amazing.
Casey: To finish a short story, OG has grown to become what I would consider some of the most elite business builders in the world when it comes to high growth tech. We are now over 814 people as of today.
Scott: Wow, that’s awesome.
Casey: But I’m most proud of is not a single effort was made to sell or to market. This was literally a case study in organic word of mouth. Very proud of delivering value to members in a way that keeps going. So yeah, that’s OG.
Scott: It’s super organic. I think I knew Jamie because we were referring him, when some of our clients had a VP of finance role or something like that, we’d always refer Jamie as a recruiter. Then he introduced me to you. I remember sitting, having coffee in North Beach.
Casey: Yep. I remember that.
Scott: I think there was a smell test involved, and I guess I passed the smell test. But it’s awesome. There’s a lot of great people there, a lot of knowledgeable people, and people just share best practices or what they like or what’s going on. There was one today that I saw was super active. It was like a genius headline. Someone was like, “Hey, is there a color printer you like?” It was like, I bet you the people have asked about hardware or things like that 50 times, but this guy or gal did a great, great post and it got tons of interaction and it’s just little things to big things. There’s a lot of big things that get discussed there, like stock options or QSBS or finance and accounting, tons of stuff. But that was just a funny one.
Casey: Yeah, that was a shocker. At first, I was like, are people going to take to that? People loved it. But yeah, normally it’s more serious, right? It’s like, “I want to be a COO.” Or “What’s going on with ChatGPT?” Or “SVB? Anyone? What’s going on over there?”
Scott: Oh God, I remember that.
Casey: Then all of a sudden, “Does anyone like their color printer?” And then it just popped off, which I think tells you a lot about the authentic engagement, where I want to say a lot of us are friends and that’s what happens when you do tenure organic versus, I have 100 salespeople trying to sell memberships.
Scott: Yeah. The other thing you guys do, which I really like, is the conference. Last year, it was in Napa, and I went to the conference. I think it was two days, if I’m not mistaken. It was great. Lots of speakers. I remember the speaker was the guy, maybe the CFO of Salesforce or something like that.
Casey: Yeah, Mark Hawkins.
Scott: He was really good. A lot of wisdom. But you just get to meet a lot of other people. It was really neat. It brings the online community; it makes it more real. It makes it more tangible. So that’s a really great event, too.
Casey: Yeah, thank you. Summit, we call it Summit. OG Summit is May 15th to the 17th, Denver for this year. So, it’ll be our third. Hope to see you there.
Scott: Awesome.
Casey: But yeah, we have a lot of fun, and the leaning of it is literally fun. So yeah, good programming mix, but networking and just having a good time.
Scott: Yeah, that is a good time, too. Well, so now you’re doing OG, but then you also have, it sounds like you’ve got a project you’re working on, and I want to tee it up for you. But there’s something you’ve learned in your career that I also agree with. Do you want to want to talk about it here?
Casey: Yeah, right. You’ve unleashed me. Okay, here we go. So, when I look back on the Operators Guild, I asked myself, why does it keep growing? Innately, I understand. But yeah, guess what? There’re many communities out there. Specifically, pretty big-name CFOs are joining. They’ve always had. If I can call him up, Charlie of Carta just joined. People I respect a ton.
Scott: Former podcast guest.
Casey: And big time COOs joined and biz ops and etc. I asked myself, there’s five CFO communities out there. There’re five COO communities out there that are legit. Why not? So I just had to ask myself.
Scott: That’s interesting because I didn’t even know there were other communities. That’s so unique to me that I didn’t even know there’s other stuff out there. It’s pretty interesting.
Casey: Yeah, I mean especially the CFO ones. CO Alliance, CFO LC, right? There’s just a bunch and they’re great. They’re great organizations. I personally, just candidly, I joined a few of those and it just wasn’t for me. It so happens that we keep growing. Then I ask myself why? Anytime the universe pulls something into existence with zero push, I think you have to ask yourself why? It is this product market fit that just happened. One of them, it falls on the category of, I try to solve a problem that I had. Travis couldn’t find a cab, Drew couldn’t store his thing so he went, you know, Dropbox. I’m not saying I’m them, but there’s just a real pain.
Scott: No.
Casey: So the epiphany was this. I said, you know what? Pull all the demographics of every single, at that time was 700 of us. I found out something really interesting. Number one, we have an NPS of over 80, which is pretty much nine out of 10 people would recommend, which is, I’m very proud of. Which is why it’s word of mouth. You can’t have a word of mouth community without a high NPS. That’s by definition. The seconds, well by definition, and it’s a paid community, by the way. So, if it’s free community, it’s hard to tell. But when it’s paid, people have a choice. They’re not going to pay unless I think it’s worth it to them. Or they have other communities that they can go to. By definition, whoever’s in the group gets along and finds value with each other. Okay, so who are those?
Scott: It also, there’s people who are… It filters out some people who might not be there for the best intentions or something like that, too. I think there’s an inherent trust or something like that, that I like about it being paid. Also, I like that your names are displayed, your reputation is important. There are all these positive factors that point people in the right direction to be on their best behavior.
Casey: I never thought about that. Yes, absolutely.
Scott: Yeah, totally.
Casey: You’re out there, but you’re safe. The fascinating thing I saw when I looked at all the members, once again, 10 years, pretty much 10 years of organic growth. People come; people go. Who has stayed? What has this organic plant grown? One, we are director and above. Well, that’s intentional. Number two is we have 235 unique titles across 700 people at the time.
Scott: Wow, that’s interesting.
Casey: I want to say most communities are less than 10. A sales community. It’s CRO, right? Sales, marketing, growth. You get to 10, maybe 20. We have 235. Okay, that’s very interesting. That’s off the charts. Okay, that’s noted. The other thing is we have four major title personas. Number one, finance. CFO, the director of finance, VP finance. Number two, ops. COO, director of ops, customer ops, ops, et cetera. Number three, special ops.
Scott: What’s that?
Casey: Rev ops, go to market ops, chief of staff, biz ops, translation. Not a big team. Internal consulting or internal projects. Chief of staff. Yeah, I think I mentioned that. Number four, early founders, CEOs and general managers. So, the jeopardy question in reverse: what do all these people have in common? What does a chief of staff, a biz ops, CFO of Carta, early founder have in common? Most people can’t answer it.
Scott: Yeah, I only know the answer you told me before we started recording.
Casey: We are multi-disciplinary generalists. Now, generalists are generally a bad term. For a lack of a better term right now, I’m just going to use it. It dawned on me. So, I went to the military at West Point, so I have a little military background on me, so I apologize for the analogy here, but it is apt, and I got signed off by a Navy SEAL that’s in the group. OG is the Navy SEALs of company building. Notice I said company building. It’s not… So, what’s happening is it used to be in tech. It’s called the people who fund it, VCs, the people who build it, product engineering, and the people who sell it. Those are the first-class citizens of Silicon Valley of Tech. Makes sense. Stripe, build it, guys, sell it. Go.
Scott: Yep, yep.
Casey: The third has now risen, and write a lot about it, is the people who scale it. They’re as valuable or whatever. They’re important. I’m not trying to compare, but there’s valuables, engineers and sales. It’s the three-legged stool. The reason why is companies are now scaling so fast. It’s like NFL speed. Before, less competition, less VCs. Now, incredible funding. We have companies burning 10 million a month. This is like high stakes, not a pizza shop so to speak. Not a simple business that you can build slowly. This is high-stakes company building.
Scott: Yeah. I’d also say, just to testify to that, I mean I have a pretty interesting perch. We have 800 something clients. I see the successful founders and I see the founders who… You don’t know why they’re not… It seems like a good idea. It seems like they can build a product or they can sell it. But I just don’t know why this isn’t working, from the outside. Then you see a pattern over a couple years where they’re not able to just do the block and tackling and be creative problem solvers outside of their own domain. Companies end up failing. There’s no tombstone that says these people couldn’t make decisions or weren’t organized enough or didn’t have enough diversity in their background or creativity to solve problems. But that’s actually what happened. They were missing a fundamental, either person on their team, or a fundamental character trait that just didn’t allow them to be successful.
Casey: Look, I’m not saying anything that’s not public here, but WeWork is an amazing product. But I think the issues they had were on the fundraising finance side of scaling. It was misaligned, et cetera. I think it’s been very well written about. That’s called scaling. It’s not good enough to just have a great product and a really good sales team, which we both had. Oh my god, the best product teams, installers and incredible sales team. But I feel like, and we had great scalers, but for another discussion, I think they didn’t have as much voice or were overridden. But that is equally as important. I think that company could today be still a five, 10 billion business if it lined it up. I think scaling hyper-speed is no longer this thing that northern Californians do. I think this is a profession. I think this is something Stanford will teach 10 years from now, of professional… No different than engineering and how much it’s advanced go to market, how much it’s advanced… The scaling profession has begun. It begun. You can see comps, people are getting paid 300, 500,000 for this. This is not some air-quote “back-office operation” anymore. These are very talented people, that could be working as the partner of McKinsey or someone at Goldman, whatever. Less about pedigree, but I think you catch my drift. These are very high-clock speed, analytical horsepower people that don’t code and don’t sell.
Scott: Yeah.
Casey: So what’s happened is-
Scott: Also, if I may, just for the audience, you’re emphasizing the speed, but I see it… Because I see companies very, very early who are trying to move fast. But there’s something about when you’re first getting a company going or even the middle early stage, where it’s not even the speed. Speed is a byproduct of good execution. But it’s like, don’t chase speed, do a good job, figure the stuff out, do it right, da da da. Then speed follows. That’s a lesson from building Kruze. We ended up growing super-fast, but it wasn’t because we were trying to grow super-fast. It was because all the blocks fit into place and then it clicked and then we were able to do it. You know what I mean?
Casey: I agree. But I would add, so a hundred percent, Kruze is one where the success of the business, the product market grows it. I do think there are choices that are made by investors and founders to go fast or not before anything happens.
Scott: I guess what I was trying to say is, this stuff’s important even if you’re not trying to go Mach 10, you know what I mean? That’s what I was trying to say.
Casey: Well, What I would say is if you choose Mach 10 and you have people on the scaling side that are not equipped to go Mach 10, I can tell you what happens.
Scott: The plane breaks a bar-
Casey: The wings rip off. If you have the talent who’s done it, the wings may not rip off and you’re able to get into, whatever, outer space. So, the meaning, I see it, my perch is, I see Navy SEALs of company building all day long operating. I see people that are less good. Or I would say, less experienced. The difference between the two, I’m going to write about, is like, all right, budgeting. There is what I would call regular and then what I would call Jedi. There’s a Jedi level that I see, because once again, I really apologize for the cheesy analogy, but there’s like war fighters, right? SEALs fight all the time. So, their playbook is different. They have to deal with, I mean, what do they call it? Special operations warfare. We’re special operations business building. The reason why SEALs, many reasons, were created is because, branches called the Army, the Navy and the Air Force were not enough to fulfill all needs. They’re amazing, of course, but some missions, some things, require, and here’s the line, specialists at being generalists.
Scott: I like that.
Casey: It is an actual specialty to be a generalist. That’s point number one, where no one describes themselves as a generalist, that would be weird. The other thing, and probably this audience here, I’m very curious. I’m going to throw in some spice. When I ask certain CFOs, why do they join OG? The whisper is, “I’m not a CFO.” What they mean by that, CFO, it just happens to be where we spike. It’s a specialty. So, the next, most interesting thing about OG members, is the number of different titles they’ve carried or can carry. One, I’m thinking, biz ops, chief of staff, CEO founder, CFO, janitor. You go down the line, someone called it portfolio career. You go down the line, the generalists carry all sorts of titles. In general, if you have a sales professional, they don’t carry all sorts of titles. They carry sales titles. Engineering, and there’s nothing wrong with that. But then there’s this weird breed that we’re confused ourselves of what career path we want, what we’re doing. Now I know why, because I’m going to finish off the analogy. Navy SEALs, and I apologize if anyone’s a SEAL. I’m just going to for analogy’s sake, they have disciplines. The disciplines are, so when you look at a Navy SEAL, it’s like, you call them SEALs. They have the same trident tattoo. But all of a sudden when you talk to one, one’s a sniper, one’s a medic, one is radio and comms, one’s a leader, one’s explosives and ordinance. Once again, apologize if I butchered it. But the point is this. Move that analogy over to generalists in business building. Those disciplines are strategic finance, data analytics, Oregon culture, board and fundraising, dealing with crazies, go to market and rev ops. These are the actual disciplines of what we do. Translation: the mix-up is people are calling the people in OG finance person, CFO, or I would say, sniper or medic. You don’t call a Navy SEAL a medic, you call them a SEAL who happens to be specialized. So, the translation is we are not bound by titles. That realization is what I want to share with everyone.
Scott: Also, I think it’s the spice of life in a lot of ways, doing a lot of different stuff. Oftentimes, I’ll be telling a startup like, “Hey man, now’s a good time for you to hire a CFO. If you get a good CFO, they’ll function a lot like a COO.”
Casey: Bingo.
Scott: Or vice versa. You see a lot of CEOs that can actually manage the finance organization, and it’s because they’ve done different stuff. They have different perspectives. But all that comes together into this super awesome professional who takes the company somewhere.
Casey: You just described the new breed that is forming.
Scott: Yeah.
Casey: I would change it. You don’t see a lot. You see them. That’s the, I think, specialty of these special generalists that operate at this level. Basically, business first, function second. If there’s anything to take away, business first, function second.
Scott: I like that.
Casey: The reason why they’re CFO, they don’t operate as a finance person or whatever COO even means. They’re a business person with skillsets called sniping, medic, whatever. In this case, finance, go-to-market ops, psychology, influencing people. That’s how generalists run, cross-functional generalists run. They have skillsets and tool sets. They don’t act like a tool. They’re not one anything. They’re ingredients, and whatever problem we need, general contractor, I got it, I’ll solve it. That’s the power of a generalist.
Scott: Yeah, totally agree. Also, I really do think it makes it more fun and gives you a lot more longevity. You see people who do the VP of finance, who maybe are just very finance or accounting focused.
Casey: Yep.
Scott: They go from company to company, which is great. That’s usually what the founder wants to plug a hole thing. But they get tired, or they get bored. I have those off the record conversations with them all the time. They’re like, “Oh my god, another software startup. This is my third one in three years. Yeah, I got everything fixed up, but now I’m just like, I need to do something else.” I think the generalist aspect actually helps you get to the next level and helps create a lot more opportunity, whether it’s at your company or the next one. But you’re just more useful in a lot of different ways. And it’s just more fun.
Casey: I would actually inverse it. My belief is the generalist is a DNA. When you say it’s spice of life, it’s Scott who enjoys… By the way, you’re a founder for a reason. By the way, you’re a perfect example. It’s why you’re a member. You could be a CFO. You could be a CEO. You could be a CEO. In fact, if you really wanted to, you could be head of sales. You probably are. But that’s called a generalist now. But not every Scott likes that. So-
Scott: No, you’re totally right. It fits my [inaudible 00:23:13].
Casey: Part of the manifesto is their breeds, just like dogs. You’re born a hunting dog. You’re born… It’s in us to want to build and go multi-discipline. We get bored with anything verticalized, which makes for a really good generalist. There’re other breeds that make for a really good salesperson or a really good engineer. It’s personality. These personality tests, these Meyer-Briggs. There’s some grounding in that. When you look at the OG, there’s going to be a personality test that comes out of, you know you’re a generalist, most likely, if you score XYZ on this quiz.
Scott: We’re huge on personality tests at Kruze. Everyone takes one. We used to use predictive index. Now we use caliper. But actually, really helps and it helps get people in the right slots.
Casey: That’s right.
Scott: You’re totally right. The different, you’re innately pulled to something, and finding that is actually the success, it’s the spice of life as well.
Casey: Yeah. Ask an engineer or a salesperson in general, “Hey, do you want to do all these other things?” A lot of them will be like, “No.”
Scott: Yeah.
Casey: “Why would I want to do that?” So that’s what I mean is there is an actual breed of us. It’s not finance professional or second in command. That doesn’t mean anything. Like chief of staff, what does that even mean? It’s very hard to describe us, but basically, to all my friends out there who are generalists, you’re no longer lost. We’ve been lost forever, which is, “Describe yourself, what do you do?” I want to help, with the help of a lot of people, write something where it’s like, “I’m that. I am that.”
Scott: I think people are going to like this. So, you’re basically talking about doing a new project where you’re going to target this and explain this methodology and explain this personality trait.
Casey: It’s a thing, and I think it’s the beginning of where people will add to it. I joke, Stanford will teach this professionalized thing in 10 years, just like they teach engineering or whatever. It’s a real thing. You can go to Wall Street, you can go to McKinsey, or you can try to do the building thing. Just as legit, just as high earning, just as hard as all the other med school law school things that has been well-grooved. This is here to stay.
Scott: Yeah. Or if someone’s listening to this, they’re starting their career, I did investment banking for three years and it became super repetitive for me. That’s how I knew I needed to try other things. But those skillsets have been with me my whole career. So, it’s not like a bad move.
Casey: Yes. Yes.
Scott: Get something, get a grounding in something and then you can launch from there.
Casey: Hundred percent. To be fair, I think there’s an argument of, do you go to these other institutions to learn something? That’s why we’re business first, finance second, business first, op second. Because we’ve come from, a lot of us come from a business sense, a business world, or an investor world. But yes, I think in the future there are worlds where, if OG is going to have OG University, there are worlds where, in theory, you could potentially get enough training if you go direct. It’s different. But I think there’s another path that will open. Right now, I do think good training institutions like consulting, like banking, are very helpful. Or like a big corporation that trains you in corporate finance. But once you break out and know that you’re a generalist, you never return. It is, you take those skills and all you do is add more skills. So, one tool belt has two belts, and then all of a sudden you have 50 tools sitting on this belt. No different than a very, very seasoned Navy SEAL.
Scott: I totally agree. So, we got a couple more minutes to wrap up. How should people, is there a web page for this? Where do they sign up? How do they…
Casey: Yeah, a lot of it’s going to start rolling out in the next year or two. I would encourage all of you that, if this resonates at all, go to, reach out to me. My little mini mission is to gather all the global SEALs around the world into a community where you’re no longer misunderstood. You’re no longer lost. More importantly, the big message is, “Hey, CFOs, you can be way more than that.” I’m not saying CFOs… Hey COOs, have you ever thought about being a CFO or CEO? Why are you so limited? No offense, when you join a COO group, there’s a little bit of a mindset of I’m going to be a COO. No, no, no. No, no, no. You can be whatever you want, but you’re not limited. If you want to do that, good. So that’s what I encourage everyone, and then get the word out, because I want to really help support this profession and these people who love to do it, and it’s a very hard job.
Scott: Totally agree. Also, there’s a really nice, self, it feels good to help other people, other peers. I get on there and answer posts. It’s fun because it’s like, oh, I probably… Sometimes, I’ll sit there and be like, you know what? There’s probably 10 people in this whole 800 people who know what I know. By the way I’m in there asking questions, too, and I want those 10 people who are real, who this is their heart and their expertise to answer me. So you do feel good. There’s a lot of… It’s cool when someone who you really respect and is accomplished and is like, “Hey, thank you for answering my question. That really made my life a lot easier.”
Casey: You mentioned an enormous point that I missed. A generalist community has an incredible diversity intelligence that is special to it because we have 235 titles. When I looked at someone’s LinkedIn, it’s basically tours of duty. So, your tours of duty happened to have certain expertise given to you. In the application of OG, it asks, what’s your PhD? Mine is building finance teams. That’s my thing. I know how to do it. I have my thing. Well, guess if you put together, if everyone had two or three PhDs, imagine the problems. Someone has gone to market Norway, they are so good at Norway go to markets.
Scott: That’s awesome.
Casey: If you ever are wanting to Europe, Norway or whatever, how much value is an hour virtual coffee with that person? It is…
Scott: I know.
Casey: Whatever, you have one. My goal is to AI, OG, GPT, this thing, where we start to extract all these spikes across all the Navy SEALs, and all the war fighting we’ve done. What new war are you fighting? Great. These two people you need to speak to. The advancement of that, and the community of that, is very exciting to me.
Scott: It’s super cool. Super cool. All right man. Thank you for coming on. Really appreciate it. I can’t wait for the OG. Check it out. Operators Guild. Then, you’re being a little coy with the projects you’re working on, and I totally respect that. But I can’t wait for that to come out, too. That’s going to be really awesome.
Casey: Yeah, it’ll be fun. Thank you for having me.
Scott: All right, man. Thank you.

Kruze Consulting is regularly reviewed as one of the preeminent providers of finance, accounting, tax and HR services to high-growth companies. For our offices in San Francisco, San Jose, Santa Monica, New York and now Austin, TX, our experienced team serves venture and seed backed companies in diverse industries from SaaS to biotech to hardware to eCommerce.

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