FOUNDERS & FRIENDS PODCAST

With Scott Orn

A Startup Podcast by Kruze Consulting

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Scott Orn

Scott Orn, CFA

Casey Woo of Operators Guild, a tightly-knit community of battle-tested operators refining the craft of scaling businesses, driving growth, and giving back; all while having a lot of fun

Posted on: 03/08/2021

Kruze Consulting's Founders and Friends Podcast · Casey Woo of Operators Guild, a tightly-knit community of battle-tested operators

Casey Woo

Casey Woo

Co-Founder, Managing Member - Operators Guild


Casey Woo of Operators Guild - Podcast Summary

Casey Woo stops by to share more on Operators Guild and how they created an organization that brings together like-minded professionals focused on cooperation and learning, resulting in mutually beneficial relationships devoid of judgement or ego.

Casey Woo of Operators Guild - Podcast Transcript

Scott: Hey, it’s Scott Orn at Kruze Consulting, and welcome to another episode of Founders & Friends. Before we start the podcast, let’s give a quick shout out to Rippling. Rippling is the new cool payroll tool that we see a lot of startups using. Rippling is great for your traditional HR and payroll. They integrate very nicely. But guess what, they did another thing. They integrate into your IT infrastructure. They make it really easy for when you hire someone to spin up all the web services in their computer. Which sounds kind of like not a huge deal, but actually we did this study at Kruze, we spent $420 on average just getting a new employee’s computer up and running and their web service up and running. It’s actually a really big deal. It saves a lot of money. The dogs are in the Dogwood. We see a lot of startups coming in to Kruze now using Rippling. So please check out Rippling. Great service, we love it. I think we have a podcast with Parker Conrad, you can hear it from his own words. But we’re seeing them take market share, so shout to Rippling. Now to another awesome podcast at Kruze Consulting’s Founders & Friends. Thanks.
Singer: (singing). It’s Kruze Consulting’s Founders & Friends, with your host, Scotty Orn.
Scott: Welcome to Founders & Fiends podcast with Scott Orn at Kruze Consulting. Today, my very special guest is Casey Woo of Landing/Operators Guild. We’ve got two things we’re going to talk about today with Casey.
Casey: You sound so professional.
Scott: I’ve done it about 195 times.
Casey: Very good shows. Thanks for having me.
Scott: Casey has been my friend for a couple of years. He actually runs a community for, I’d say, COOs, CFOs, called Operators Guild, which I’m a member of and I really enjoy. I’ve learned a lot. Then he’s also CFO of a company called Landing, which is a really exciting startup. So, I figured we could get a little two for one action here and have Casey on the podcast and talk about both entities. Does that work?
Casey: That works.
Scott: Cool. Do you want to give your quick, like, retrace your career a little bit and give people a little background on you so they know the context?
Casey: I’m from L.A. I did something that most Chinese American families don’t do, is go to the military. Shocked my entire family. I went to West point.
Scott: I didn’t know that. Wow.
Casey: Yeah, yeah. I had your traditional civilian colleges and then I had one called the Military Academy, and they’re like, “Which one are you going to go to?” When I picked the Military Academy, they’re like, “What?” I’m a sucker for challenge. Someone told me once, “Oh, West point is really hard to get into and out of.” That stuck with me and I’m like, I want to do that. It’s so bad as. It is awesome and it was tough. I went there.
Scott: West Point, or what military college did you go to?
Casey: Yeah, I went to West Point.
Scott: Oh, wow. In my [inaudible] school class, the most impressive people by far were all the people who went to the military colleges. Actually, when you look at them now, they’re all like the most successful people. It’s ridiculous.
Casey: Until you met me. No, but from there, so I transferred to Harvard after two and a half years. I did so not because I didn’t want to do the army, but because I started grow a lot of interests and quickly realized, so I did well enough. I say that because there’s the people who hate it and leave and there’s the people who did well enough, who, it goes by rank there, so if you’re high enough ranking you, you pretty much know what you can pick as a branch when you graduate. I wanted aviation. A lot of people do. Aviation, Hawaii, that’s the first post and branch that to go down. Apaches and Chinooks. Black Hawks. When I researched it, it would be ten-year commitment from there. Two and a half more years of West Point, 7 years commit. It’s longer because you’re talking aviation. They spend a lot more money on you. I was like, so what can I do in these 10 years? Can I study economics? They’re like, the finance branch just closed. You can fly helicopters and of your 10 years, only three will be leading men. Most of its training and the other is you’re too high ranking and you get out of the seat and you sit in air conditioned radar screen rooms. I was like what are you after that? Oh, there’s people who are weather helicopter pilots. I’m like, okay. So anyways, long story short, I begrudgingly had to choose, because it’s a 10-year commitment. I went to Harvard for economics. I was the odd ball out who knows how to fire rifles and tanks and stuff with Harvard kids. Anyways, I jumped in and this is my story, where as an economics major you’re told there’s two steps to Nirvana. Step one, go to Manhattan and get an investment banking job at Goldman Sachs or Morgan Stanley.
Scott: Or Hambrecht & Quist, which is where I wound up.
Casey: Yeah. So, I was like, okay. Last time I checked, I was cleaning weapons. I’m like is this what you do? Okay. I mean, I know I’m being facetious, but I really enjoyed my internship at Morgan Stanley. I think I got the job because I could tell war stories and military stories to separate myself. I definitely wasn’t the smartest.
Scott: They also knew you wouldn’t crack when you’re working at 3:00 AM for the sixth day in a row kind of thing.
Casey: That’s spot on. What got me the interview, I think, that got me the spot was I said, by the way, the military is very similar to banking. They’re like, “What do you mean?” It’s collegial. It’s attention to detail. It’s endurance. They just loved it. Actually, it is true. It’s hardship. Analysts are just working a hundred hours. It’s the same bootcamp, it’s just in suits versus camouflage. Anyhow, I loved it. Half my groomsmen are from Morgan Stanley and my wife. So that was a pretty good two years there.
Scott: Wow.
Casey: Yeah.
Scott: What year were you there? Because I don’t know if you’re older than me or younger than me, it might have been the same time.
Casey: ‘04 and ‘05.
Scott: Okay. I was ‘99 to ‘02. So, a little bit ahead of you.
Casey: Yeah. So, after that there’s only one last step to Nirvana, get a private equity or hedge fund job and retire. And it works. I’m old enough now, there’s a lot of friends of mine that are just fine and they took two steps and they’re done. So, at the age of 24, I remember I was walking along Fifth Avenue, I got the call from the recruiter. It was like, you’re going to get a job at Maverick Capital, well-known Tiger Cub fund, covering retail. We’re talking Under Armour, Victoria’s Secret fashion shows, we’ve got a 3 billion book, you’re going to learn from the best, here’s your corner office. I’m like, oh my God, this is amazing, right? It was. It was super cool. I felt super fortunate. You’re in the club. I had people calling me, “How do I do hedge funds?” “How do I do this?” All the politics behind getting in. It was awesome. But after a year, I remember, my office was bigger than my apartment. I was swinging around in the chair, overlooking Central Park, I just felt really lucky. I was overpaid, 20, single, Manhattan. Like, what do you have to complain about? I was like, there’s something wrong. Wow, this is it. I’m supposed to do this for 10 years. I don’t know if I can do this for 10 years. I didn’t know why. I’ll fast forward. It took me about another four years to figure it out. So, I did more public investing, I learned a lot about that side, and eventually I learned there’s two things that drive me, which, by the way, is what drives operators. Number one, we like to work with others. It doesn’t mean we’re extroverts. We love working on teams. I like the military and banking, oddly, more than hedge funds. I didn’t understand. It because those are team sports.
Scott: Totally, totally.
Casey: I tell people, “Have you seen The Big Short?” Oh, yeah. Well that guy, if you just pause in his office, that’s 99% of what you do. It’s [crosstalk].
Scott: I remember doing hedge fund interviews after Hambrecht & Quist or JPMorgan, and the guys would just have like piles of paper in their office and they would just sit there reading research reports all day and stuff like that. I was like, ooh. I’m on the same exact way you are. Keep going, I don’t want to interrupt you, but I’m on [inaudible].
Casey: Right? When I tell the story, it resonates with a lot of people because no one ever told me when I was growing up, you need to play team sports. They’re just like, oh, you need to do economics or whatever and I never realized how important environment is. So now I know I need to be with people, I need to be with teams. The second thing that I learned about myself is I love to build things. So, investing is a very respectable, extremely difficult thing. I have incredibly impressive friends who are in it. But for me, I realized it was more like a treadmill. Different stock, same day. It’s very interesting if that’s what you like to do, but I like Legos and Ikea furniture and businesses, I don’t care what it is that’s built. So, what is the perfect world for me? High growth startups. All a startup is is a bunch of people building. I took the leap, took a huge pay cut, after just realizing I don’t know what it is, but let me join this 10-person company. FinTech, SaaS, New York, so Silicon Alley. Loved it. Wife didn’t love it because I got so consumed by it, but I knew I was fish in water. I thought I was fish in water in finance. No, no, no, no, no. I’m going to fast forward because I’m way over four minutes. But basically, my philosophy is if you’re going to do something, go where the best are. If you’re in the military, you go to West Point and get your butt kicked. If you want to do film, you should go to Hollywood. If you want to do tech, go to Bay area. So, I came out here and then I was kind of lonely because I switched my careers. I know a ton of Wall Street folks, but I don’t know any startup folks. By the way, this is after the ‘08.
Scott: A few years ago, you didn’t know anyone.
Casey: Goldman Sachs and Morgan Stanley were not something you want to see on a resume because of the crash. So, when you’re talking to all these Stripe and all these bad-ass tech companies, they’re like, ew, you’re a wall street guy? But they loved my 10-person going to a hundred tech startup.
Scott: Yeah. Yeah, yeah, yeah.
Casey: They’re like mad respect. But all this other stuff? Get it off. So, it’s ironic because it meant nothing. It meant everything in New York, it means nothing out here. So, I restarted. This is where the OG thing comes in, where I was looking for people, I wanted others to learn from. My title is VP Finance in biz ops. What the hell is that? Are you an accountant? Are you a McKinsey guy? Like, what are you? I met a lot of engineers, a lot of VCs, a lot of COs, but like I didn’t meet my type. In fact, I don’t even know what my type was, I just called it an operator. A guy named Jamie Ceglarz, he invited me-
Scott: He [crosstalk] back in the day.
Casey: I’m sorry? Oh yeah, yeah, that’s right. He was on the podcast. He invited me to a heads of finance lunch. I was like, wait a minute, these are my people. I didn’t know that many people, but he did. So, at the end of it, I said, “Hey, Jamie, I’d love to do this again, but I have an idea. I want to create like a mom’s group for operators where it’s confidential, hard-hitting, helping, friendship, therapy, best practices. He’s like, sure. We got very lucky. That five, six, I think, seven-person group, the universe aligned, chemistry, friendship, met every month and eventually, well, there’s only three rules, no promotion/solicitation, show up, what’s said here, stays here. We added a fourth because all of a sudden someone said, hey, I know this other awesome operator who’d be great for the group. So, we go, okay. So, there’s a nomination process. No bad actors. Everyone needs to agree. Seven became 15, became 50, became 100. No joke, one night when me and Jamie were working on Operators Guild, because it’s like a night and weekend thing, my wife thought I was cheating on her. It was like, listen-
Scott: Who’s Jamie?
Casey: Yeah. It’s okay. It’s okay if you like guys. It’s fine. But like, who’s Jamie? What is this? It doesn’t pay you anything. I said it’s this group that’s kind of grown out of control, but we love the people in it and we don’t want to let the quality go down so it just takes up more time. You’d be surprised how something that looks simple takes up that much time.
Scott: Yeah, of course.
Casey: Eventually, it got so big that me and Jamie looked at each other and said, listen. Because we didn’t charge dues, it was like out of our pocket, our time. We’re like, listen, we’ve got to hire someone to help this. We were really hesitant. But it’s free. At the time, Adam Neumann taught me something from WeWork. Free’s not good. You know? Of course, I was like, Oh Adam, Adam. But he’s kind of right. When there’s no skin in the game equally in a relationship, it kinds of perverses things. It doesn’t mean charge an arm and a leg, but there was like, are you serious about this group, are you going to attend? That was the best decision we did. It’s not a lot of money, but it weeded out people that were kind of freeloading, kept the people that found tons of value. People showed up more and we hired an awesome operator to run it and now we’re 500.
Scott: I didn’t know it was that big. Wow, that’s amazing. I think I’ve been a member for a little more of a year. By the way, you said a ton of stuff. You and I are wired the same way. I joined [inaudible] because I wanted to build something. I’m the same exact way. Then I think I’ve told you this, but I ran an online community for people with rare diseases for a long time.
Casey: That’s right.
Scott: I totally empathize with your working at night. It’s addictive. It’s like so fun and people are getting a lot of value out of it. It’s fun to see you. You call it OG most of the time, but it’s called Operators Guild, and I’ve been a member. There’s just a lot of good questions there, like random stuff when you’re running a business. Or maybe you’re a finance person or chief operating officer or something like that, that you have like a peer group you can just ask the question to.
Casey: Well, here is where I think OG gets super interesting after looking back six, seven years. The most proud thing about OG is that of the 500, not a single one was sold to, marketed to. We don’t have a sales person. We don’t have a marketing person. It’s not a business. I don’t pay my kid’s tuition with this. Translation: It’s all word of mouth.
Scott: Yeah, yeah, yeah.
Casey: It grew with word of mouth. What happens when you have a completely organic community is it has a whole different feel and ethos compared to a traditional professional community. So, I’m not going to name some, but we’ve all been to the wine and cheese blazer party where, welcome every Friday, we will meet and you can dress in your blazer, have awkward circle conversations where you’re like, hey, LinkedIn Connect? LinkedIn Connect. What I realized was if I look back at all the, air quote, networking I’ve done, that stuff that has been the most valuable is my friends. It’s not-
Scott: You meet friends through it, you know? The other thing I like about it is it’s very efficient, like I can just ask a question when I need to or I’ll answer people’s questions when I have a thought. It’s like efficient networking. I guess maybe it’s a social network. But I don’t have to sit at a cocktail party, through someone’s terrible stories or things like that, I just kind of read what I want to read. There’s some weekly, or maybe it’s like once a month, there’s like a lunch get together or things like that where you do stuff, a video. It’s pretty cool. Those are high quality, but it’s almost like exactly fit for our time. It’s a really great service. I really enjoy it.
Casey: Yeah. Because what happened is that the punchline is we’re 500 friends who happen to know what we do for a living, we’re not 500 operators on an email distro. I think that’s, yeah, it creates a different safety ethos. Authenticity is probably the word I’m looking for. So that’s what I’m most proud of.
Scott: That’s really cool. If people are interested in that, what do they do? Because we’re talking about it. Do they reach out to you via email? How should they get involved?
Casey: You absolutely can. The easiest way is our website, operators-guild.com. From there you can read about it. There’s an apply button, obviously, how you heard about it. It could be the podcast. It could be Scott. I love reading that question. Where’d you hear about it? And it’s an OG member. It’s cool.
Scott: It’s a great service and it makes a lot of people smarter. Kudos to you. Kudos to Jamie. Yeah, you guys, I can’t believe 500 people. It must have like doubled in the last year, right, or something like that? It feels like it’s gone up a lot.
Casey: Yeah, COVID actually accelerated it.
Scott: Oh, yeah.
Casey: The need for navigating through uncertain times with friends and the loneliness and the uncertainty was awesome. Providing that was just, once again, I go back to the word friendship. I didn’t realize how much of it was we’re a friendship group. I know it sounds kind of weird, but that’s what makes it just different.
Scott: Yeah. The [PBB] time was really good because everyone was in the dark, everyone was piecing together what they knew. It was a shit show and we’re about to enter another shit show of PBB, too, next week. Yeah, it’s just so helpful to have like professionals that you can rely on.
Casey: I knew more than our counsel. Because the power of crowdsourcing, so we were all doing PPB live, people would literally in real time be like actually they just changed it, actually it’s this, and that would challenge my counsel, for a thousand an hour, and say that’s not the new rules. He goes, “Yes, it is.” I would source it. I’d be like, no, look at this. So, the amazing ability to leverage a community was super cool to see in action.
Scott: Yeah, I know. It was crazy.
Casey: Hey, it’s Scott Orn at Kruze Consulting. Before we get back to the podcast, quick shout out to ChartHop. ChartHop is one of my favorite new SaaS tools on the market. Basically, what ChartHop does is it puts your org chart in the cloud. I always like to say it brings transparency to your organization so everyone in the organization can see who they report to, they can see the full org chart of the company and how their group relates to other groups. It also has a lot of information on the individuals in the company. So, you can click on the ChartHop profile and just get like where people live, their experience, Slack handles, all this kind of stuff. It’s just a really great tool. The other thing is ChartHop has started doing some cool stuff around compensation and budgeting planning. So, you can actually start seeing like what the cost structure of the company will look like in certain kind of scenarios. So, I’m loving ChartHop. Check it out, charthop.com. We use it at Kruze, really like it, and I can’t recommend it enough. All right, back to the podcast. So that’s OG. Let’s talk about your other passion besides family, which is Landings. This is a cool idea. So, do you want to explain your startup? So, I’ll explain the startup, and more so, Bill, who is the founder, I think, which is a very important background. But Landing, in short, wants to be the Marriott Starwood of apartment living. Similar to used cars, it’s a very fragmented market. It’s a painful experience, lack of transparency, et cetera. There’s just no one front door, no one place. I think Carvana is doing it for used cars. So that’s Landing in a nutshell.
Scott: Opendoor did it for houses. That’s what Opendoor is doing for houses.
Casey: Exactly. The other thing that was fortuitous is one of the premises of Landing is the status quo is Craigslist, Ikea, Home Depot, Comcast, and 12-month lease, unfurnished, four white walls, leasing office. That’s pretty much what it is for a long time. We’ve all, well, most of us, have done the San Francisco, New York apartment hunting. Oh my gosh, right? We have all stories. We all have our battle wounds. It’s that. It’s like, it doesn’t have to be like that. So, everything from flexibility, so why does it have to be 12 months? Why can’t it be four, three?
Scott: Yeah. Yeah.
Casey: So, what’s interesting is when you think about flexibility, over time, no one stays at 30 years at a job anymore. Right? Now it’s like on average operators stay two years, just as a demographic. But the point is even buying a home now people get worried, because maybe I move, and then COVID happened.
Scott: [inaudible] COVID, it’s like this is tailor made for you guys.
Casey: Boom. COVID was like, wait a minute, I can work for Scott in Denver?
Scott: Or Wyoming, or Virginia, or wherever. Yeah.
Casey: But what is a hurdle to moving? Furniture.
Scott: Yep.
Casey: All the other costs that go with it. Now you just bring your toothbrush. So, you know what? I’m going to try Austin for a bit. Go try Austin. Maybe I like it, maybe I don’t. I don’t want to buy all this Ikea furniture. Or if I do, it’s going to be ragtag. Great, you’re done with that. You want to go to New York? Go to New York. So, we’re in like 70 markets. Hopefully, we’ll be international. It is membership based, so think kind of like Inspirado. There’s a concierge service. There’s much higher-end touch. But yeah, it’s great class A, class B availability.
Scott: That’s great. So, I didn’t know you guys are in 70 markets. That’s insane.
Casey: Yeah. Well, I think we’re most proud of our selection. Oh, the other thing is we do unfurnished, too. So, we are the one front door for a landlord, so it’s not just furnished. So, imagine a world where you go look at a site and on the left side, it’s an empty floor plan look and it has a price on it, and on the right side, it’s furnished and there’s a price on it. Why can’t you choose furnished or not?
Scott: Yeah, for sure. So, you guys go to a landlord and say like, “Hey, we can manage this building in the same way that Marriott manages a hotel that a REIT owns, real estate investment trust owns, and we’re going to make it first-class and people are going to have a great experience. We’re good at this and we’re good at that concierge service. It’s beneficial to both of us. You get a higher rent, we collect some service fees, and the customer wins because it’s a better experience.” Right? That’s the idea?
Casey: Bingo. I mean what does Four Seasons have? They have a bag full of great customers, right? That’s what they bring.
Scott: It’s their brand and expectation, yeah.
Casey: That’s exactly right. That’s exactly right.
Scott: So, 70 markets, is it all throughout the United States or how do you choose your markets? What’s the methodology?
Casey: Probably the usual way you would think. One is the denser markets, the markets that have the most ins and outs. So, you start with the tier one markets and the classic demographics of a certain socioeconomic, right? Because obviously, it’s furnished, right? So, it’s going to be more than the traditional. But eventually, it’s going to be, it’s the top, 50 top 70. In fact, I think the goal is not to be just New York, San Francisco. In fact, it’s probably the opposite, right? What we really work extremely well is in your 1500 a month rent, that instead of 1500, maybe it’s 2000 or 1900, but you get $20,000 worth of furniture and you don’t have to deal with any issues.
Scott: [crosstalk] the lease earlier or stay longer, or whatever it is, right? That’s a big part of what you guys are offering.
Casey: Oh, by the way, no deposit.
Scott: Yeah. Wow, no deposit?
Casey: Yeah, no security deposit. A lot of these fees are gone. Yeah, it’s just a different experience.
Scott: So, with COVID, what I saw happen with some of our team members was we still had, we’re national or international, but we still had seven people in San Francisco, but all five, besides Vanessa and I, moved out of San Francisco immediately when COVID hit. Almost all of them did like a journey around the United States over a couple months and lived in a bunch of different cities. Some people are just still doing it, you know? That’s fine with us, but this makes so much sense because you can go from like one landing property to another and just have that freedom. It’s really cool.
Casey: Send them our way.
Scott: Yeah. I’m jealous because I’m 44, almost 44, and I would have totally done this in my twenties or early thirties, you know? Like, oh my God, what an opportunity.
Casey: I know exactly what you mean. I have team members who were are Hawaii and Montana and I’m like, I got three little ones, I just stay here. I know exactly what you mean.
Scott: So, you guys are going to just keep expanding the markets and keep expanding properties in the market, and that’s really cool. Wow. I forgot how you got connected with the company. Did you know the founder?
Casey: So yeah, so I mentioned Bill. The short answer is I joined for Bill, and this is what I think is such an interesting story. For those who knew me coming out of WeWork, I actually really loved WeWork. People think it’s like a… No, I love growth stage. I learned a ton. There’s a lot of benefits. I’m a growth operator. I had a, air quote, tattoo on my arm that says Do Not Do Early Stage. I’ve done multiple stages, from 10 to 50, to 150 to 3000 to 10,000, and there’s like a Goldilocks. I was like, okay, this growth stage, let’s go nuts, the more zeros, the bigger, the more ambitious, that’s me. So recruiters knew that, my friends knew that. Diversa Partners called up and said, “Hey, would you meet a guy named Bill Smith?” I looked at it, proptech, series A. Nope.
Scott: Like, series A, uh-oh.
Casey: Also, I’m coming off of WeWork, right? So, it’s like, “Oh man, nope.”
Scott: You and I, that’s when we met. You were doing like crazy finance meetings all day long and stuff like that, trying to like save the company and figure out what the go-forward for WeWork was going to look like and things like that, so that was a stressful time.
Casey: Yeah, it was. It was intense. You kind of learn the most during those times.
Scott: Yeah, totally.
Casey: So, in that sense, I was extremely grateful. Then they said, “Just meet with them.” I said, “Okay, sure. Why not?” Every successive meeting was more interesting, and more interesting not even about the business. I’ve done this for, I said six startups now, or seven? I don’t know. I’ve lost count. It is about the founder.
Scott: Yeah.
Casey: More so than you would ever think. What’s so unique about Bill is I’ve worked for a lot of great founders, most of them are first time. Sometimes first time is awesome. Sometimes they have to learn a few things. So, I’ve done it. Go ahead.
Scott: I said, we certainly had to learn some things. It’s hard.
Casey: Exactly. But imagine the second time around, or the third time around, there’s a lot of things you don’t even need to tell them anymore.
Scott: Yeah.
Casey: Bill’s a four time. Bill, I believe, if I can get the story right, he, at the age of five, asked for a briefcase. He’s from entrepreneur family. He’s just built that way. I believe at 16, he had a business or side business that was making money where he’s like, I just need to continue to do that, so he just left school. So, since the age of 16, he’s just been building businesses. I think, three successful exits. You may have heard his last one is called Shipt, sold to target. He’s just an incredible operator. So, part of it was, you know what? I’ve never worked for a four-time operator, and I believe it’s a skill sport. I mean, if you think Elon Musk is just getting lucky all three times, it’s not. There’s skill in it. There is a art to it. But the business model of course was tricky, right? It’s capital intensive. I was like, ah, humming and hawing. Then, you know what? I say, “You know what? I want to go work with Bill.”
Scott: Yeah.
Casey: The biggest thing he said to me that won me over was, “Casey, you can say I’m successful, you can say I’ve done this stuff, but I’ve learned a great lesson, a mistake, that I won’t do again. Hiring seasoned late stage talent too late.” He goes, “A lot of companies, what they do is let’s do series A, and then we’re going to just swap them out, and then series C, and then we’re going.” He’s like, “What are you saving? You’re saving this, but it’s non-linear.”
Scott: Yeah.
Casey: You get a Scott Kruze to come in and set up your shop versus, what’s that worth? It’s more than whatever premium you charge. So, he understood that.
Scott: Yeah. Well also, he’s got the track record to be able to raise capital at good valuations that facilitate that, too. That’s one of the benefits of being a seasoned entrepreneur and being successful.
Casey: That’s right. He appreciates finance.
Scott: It’s so finance intensive, too.
Casey: Spot on. So those two, combined with Bill, I was like, “You know what?” He’s like, “Come on, let’s just try it. We’ll know in 12 months.” He also said, “I’m going big or going home.” Right? I can be with my kids. I don’t need to work. I love that. He’s like, “We’re going to make a difference in an industry or forget it, not worth my time.” I’m like, “Let’s go.” You know what? It’s been almost 12 months and pretty happy I made that decision. Despite my tattoo.
Scott: Are you rolling up your sleeve? I can see the video here. Amazing. Well, you’ve had a good run. It sounds like you got a couple really awesome years ahead of you at Landing and the OG is going to keep you busy. You’ve got a lot on your plate, plus you got like three kids, don’t you? Or how many kids do you have?
Casey: Yeah, I have three now. Yeah, it’s pretty awesome.
Scott: A very full life.
Casey: That’s right. That’s right.
Scott: Awesome, man. Well, thank you for coming by. I really appreciate it. Everyone can check out Operators Guild and email Casey or click to join, and then check out Landing. It sounds amazing. This is, again, something I wish existed when I was in my twenties and early thirties when I had a lot more personal freedom than I do now. I would be all over the country. I’d probably be hitting all 70 of those markets at different times.
Casey: Please do.
Scott: Awesome, man. Thank you so much. Appreciate it.
Casey: Thank you.
Singer: (singing). It’s Kruze Consulting Founders & Friends with your host Scotty Orn.

Find out why Kruze Consulting is one of the leading accounting firms in San Francisco and the US, serving funded, early-stage companies. Kruze clients have raised over $4.5 billion in venture capital and seed financing, and our research and development tax credit work has saved clients millions of dollars in burn rate and payroll taxes. Contact Kruze to learn more.

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