CXO Conversation Podcast

January 20, 2026

10 Minute Clip with Casey Woo

In “Making the Hardest Call – Admitting it’s Not for You,” Casey Woo, former CFO for Landing.com, shares the pivotal moments that shaped his career journey—from starting at West Point and pivoting to Harvard, to walking away from Wall Street to pursue his passion for building and leading companies. With CFO and COO roles at firms including WeWork and Zozi, Casey reflects on following your own path instead of others’ expectations, the lessons he’s learned on his way to the C-suite, and why choosing finance allowed him to combine strategy with impact. His story is a powerful reminder that the hardest calls often lead to the most fulfilling careers.

For the full interview: https://ocns.co/making-the-hardest-call-admitting-its-not-for-you/

10 Min Clip Transcript

Michael Mitchel: [00:00:00] All right. I’m gonna kick it.

Hey, join us today on CXO conversations is Casey Wu, CFO of Landing. Casey has had several major pivots so far in his career and they involved some hard choices in soul searching that at first glance, uh, you may scratch your head and say he walked away from that. Uh, he was selected, uh uh, and started at West Point, but graduated from Harvard.

Worked at hedge fund making Wall Street money, but walked away. Today we’re gonna talk with Casey about following your passion and not the expectations of others, what he is learned from his, uh, on his path to CFO, including time at WeWork, and advice to the next great CXO generation. Welcome to the podcast, Casey.

Could you, um, could you share, uh, the landing pitch with everybody? Thanks. Thank you, Michael, for

Casey Woo: having me. As it relates to landing. Landing wants to be the Marriott for [00:01:00] apartment renting.

Michael Mitchel: Mm-hmm.

Casey Woo: Right now in apartment renting in general, there is no consumer brand. It is fragmented. It’s the local leasing office.

It’s the skyscraper you walk into. It’s Craigslist apartments.com. There is no brand that owns it, like hotels have brands. So that’s kind of point number one. Point number two is landing is going to be and is, in my humble opinion, the leader. Inflexible long-term living. So let me break that down a little.

There’s a few swim lanes or categories when it comes to apartments. Number one is corporate housing. That’s pretty established. There’s players in it. They sell to McKinsey or Deloitte, and they, they earn a fat margin and. It’s kind of price in sensitive in that sense. And then it’s like your one two month corporate exec.

Okay. That is a very particular type of swim lane. The second is vacation rentals. Mm-hmm. [00:02:00] Airbnb, VRBO, et cetera. And the third is living. So it’s not corporate, it’s not vacation, it’s your primary. That’s us. The other way I’ll say it is I studied consumer as a public equity investor, and the way with consumers is very simple.

Humans think of top of mind categories. If you say search engine, you think. Google, like pretty almost immediately. Mm-hmm. If I think vacation rental, you think immediately Airbnb. Okay. So a final, I’ll, I’ll kind of end with this. The way consumers pick is category, so, okay. Michael wants to go somewhere for two days.

I can almost assure you he’s thinking hotel or Airbnb. Right. Okay. No, Michael wants to do two to three weeks, four weeks. Uh, he’s, it’s Airbnb. Maybe the view, I can pretty much guess it, but the minute I say, Michael, what about living somewhere for four months? Four and a half months, nine months, 9.2 months.

No, [00:03:00] just kidding. I’m gonna switch to another city. It’s landing. So it’s the flexibility right now, right? Right now no one thinks of anything. They think of Craigslist and maybe Airbnb. Kinda sounds like

Michael Mitchel: you describe the We work for apartments.

Casey Woo: Flexibility. It, it, it’s, WeWork took these 15 year, three year leases, et cetera, these long structured, rigid way that landlords operate and broke it apart.

Michael Mitchel: Mm-hmm.

Casey Woo: And that is basically what landing does. And the other thing is it’s turnkey. So the other thing is you bring your toothbrush and your wardrobe. Everything from the spatula on up is taken care of for you. Oh, that’s

Michael Mitchel: cool.

Casey Woo: And we, and we think flexible living is going to be a big section of the, of the population will turn into a flexible living, uh, lifestyle.

Right.

Michael Mitchel: Okay. Cool. Um, I’m going to, the one thing that really struck me when, when, uh, I saw your bio is that you [00:04:00] attended West Point, but you graduated from Harvard. And the reason why I, obviously everyone knows I’m really active in veteran community. I used to be, you know, I’ve done interviews with, with the students, try and get in, you know, part of the selection committee, so I know how tough it is.

So can, why’d you apply to West Point and then switch to Harvard? Tell me a little bit about, that’s

Casey Woo: a little bit of an embarrassing story. Um, so I was kind of the classic straight A student. Uh, I was valedictorian of my high school and you know, I had all the aspirations as any Chinese. Immigrant American, uh, to go to Ivy League.

Michael Mitchel: Mm-hmm.

Casey Woo: So I, I was gonna apply to the usual suspects, but my uncle randomly one day was like, have you heard of West Point? Which is a, a mythical thing in the Chinese land, um, that they really admire. And of course I said, what is that? And basically it became one of those, like, that is so badass. I wanna be able to do that and I considered myself not a dumb 16-year-old, [00:05:00] but I was like very drawn to just, I want to do that.

It was that simple. No. Did I say I want to be in the military? I didn’t even think about that. I know that sounds crazy. I just like, I want to do that. One thing led to another, almost as like kind of like a fun thing. Like, okay, let’s try this thing and apply, and then one thing led to another and all of a sudden I have a fat package from West Point.

Michael Mitchel: Mm-hmm.

Casey Woo: I also have a couple of pat packages from some, uh, other institutions that I think most people would’ve said, what are you doing? Like, why wouldn’t you go there? And I’ll never forget the day I was on the dining room table, the offers were laid out. My dad said, so where are you gonna go? The one that stood out amongst all the civilian schools was this leadership institution that was air quote badass.

Michael Mitchel: Mm-hmm.

Casey Woo: And I said that one, he jumped for joy ’cause it’s free. So my mom started crying.

Michael Mitchel: Mm-hmm.

Casey Woo: Because what Chinese boy does that, why? Why are you going to the military

Michael Mitchel: right

Casey Woo: now? That’s why it went to West Point. [00:06:00] So it turns out I like a lot of West pointers, it was like, whoa, this is hard, et cetera. But as time went on, I really started to like it, the comradery, et cetera, et cetera.

Um, however, I also started to realize after my freshman year. I signed on for a 10 plus year commitment. I know that sounds kind of crazy to people right now. Like it’s like kind of duh. Mm-hmm. But it didn’t really dawn on me that I signed up for a career, not in education.

Michael Mitchel: Right.

Casey Woo: But, okay. So I’m in it. The very unique thing about the academies is it is so regimented and structured.

You can literally f. Look to the sophomore if you’re a freshman, and you’ll know almost exactly what you’ll be doing a year from now.

Michael Mitchel: Mm-hmm.

Casey Woo: So there’s this weird kind of forward-looking crystal ball of what you’ll be doing. Um, this. So the other thing is people don’t know that the [00:07:00] first day of your junior year is the actual day.

You’re committed. I didn’t even know this. I was like, wait a minute. I thought I was committed. No, not until your junior year. Okay. So that. Was like, okay, I need to really make sure this is something I want.

Michael Mitchel: Hmm.

Casey Woo: The second was, once again, I’m just, this is the facts is I was pretty high ranking there in terms of academia and like GPA, there’s like three GPA there and what happens is so long as you are up in the top 10%, you pretty much can pick what you want when you graduate.

So I had the luxury of saying, I probably will get my pick and I want to pick aviation so I could narrow down. My future into, let me just talk to aviation officers and figure out if this is for me of the 10 years. So basically junior, senior year two plus about another seven because it’s a little bit longer than the normal five because of the training that goes into like Apache helicopter pilots and Black Hawk.

I’m, look, I’m staring down a nine and a half [00:08:00] year commitment.

Michael Mitchel: Mm-hmm.

Casey Woo: From point of commitment. So I just started asking all these aviation officers who are my professors, et cetera. What’s it like? The short answer is, it wasn’t a good answer for me. It was, okay, Casey, of the nine and a half years, about four more schooling and training and simulators.

Then you have this juicy two, three year period where you’re leading men out there, flying, fighting, et cetera, which you all wanna do. Mm-hmm. And then you get too high ranking and you get pulled out of the cockpit and then you sit and you kind of, you know, manage. So I did the math. I said, wow, by the age of 30.

I have no choice but to do this, and only 30% of that time is leading men and what I love and, and being out there. So the efficiency, so to speak, was very hard. I also was someone that has never been committed beyond two years of anything, not even a girlfriend or anything. And you’re asking me for a nine and a half year commitment.

All this to say is I, um, I applied to. Um, Harvard [00:09:00] and some other schools, very few that said, all right, if I didn’t wanna do this, I need some kind of out. Otherwise, I mean, that’s it. Like you can’t, you didn’t drop outta school or, or, or sign this nine, didn’t have your commitment. Um, I was fortunate enough to, uh, to get into Harvard and I had to make a tough choice.

I felt it was the right choice for me at the time, but I literally remember saying to my friends, it’s like picking my left arm or right arm because I gave so much to that place. I loved it. I wanted to, and I even asked, you know, the, the head of the school who was. Giving me a very hard time for leaving.

And I said, I know this sounds crazy, sir, but is there a way I can serve, serve but less time? And he obviously laughed, said, we’re not gonna change the rules of Congress for you. Right. So you’re either gonna do nine and a half years or, or nothing. And, and that kind of made it okay, well then I guess it has to be nothing.

But that’s not what I want.

Michael Mitchel: I, I would think that, um, ’cause again, I mean, I know how tough it is to get in and you know how tough it was to get in. You’re [00:10:00] surrounded by. The top tier and there’s this camaraderie culture you’re surrounded with and you see your ca classmates with their passion. You know, we call it gung ho, whatever you want, phrase it.

Mm-hmm. Everyone’s really excited to be being there. It had to have been really, really hard to, to actually come that some, this isn’t a fit for me. I, I find that personally incredibly brave.

Casey Woo: Yeah. I, I would Well, thank you for that. I would, I felt, to me, I guess it was less brave for me and more. I felt the opposite.

I felt I was, was I running away from something that was tough?

Michael Mitchel: Mm-hmm.

Casey Woo: That was hard that this nine and a half years that I was kind of becoming like, I wanna do what I wanna do that’s more fun and easy and that’s why I left.

Michael Mitchel: Right.

Casey Woo: Um, so I felt it that way. But you’re absolutely right in terms of like all that I gave, I mean, I was high ranking at the school.

I had a lot of friends. I started really liking it. It was the, I liked it, but I didn’t like it for another [00:11:00] decade. Liked it. It’s, it’s less about the decade, it’s more about the inability to do anything else.

Michael Mitchel: Mm-hmm. Well, I’ve learned over time, I’m

Casey Woo: a very free spirit. Yeah. And I think that was what got me

Michael Mitchel: my perspective.

It it, that part’s irrelevant to me when we talk about this because it’s the fact that you made that hard decision, it wasn’t a good fit for you for whatever reason. Yeah. And I think that’s true of anybody. It’s hard. I mean, I, and you know, I, a couple years ago, I. Wasn’t a, a situation at quite West Point where I signed on for something, I quickly realized it wasn’t a fit for me.

And I, I was stubborn. I said, well, I don’t want, I, I I don’t wanna give up. And I stuck it out and it’s ultimately, I just delayed it. Inevitable. Right. So, um, but, but here, but outta that experience, what did you take away from it? What, what stayed with you that you’re, that’s still a part of you today?

Casey Woo: Oh man.

Uh. I dunno where I begin. I think the first thing is [00:12:00] West Point is unlike air quote civilian schools, the whole thing is designed well to create leaders. But I think more interesting is to, to have you face failure.

Michael Mitchel: Mm-hmm.

Casey Woo: The people that generally attend West Point are they generally win. Right. And I’m not, you know, they’re valedictorians, they like.

They’re, they’re doing well. They’re, they’re top athletes and all of a sudden you get to an environment where you just, banana peels are everywhere, right? You’re getting punched metaphorically in the face, you know, by Mike Tyson, and you’re not used to it. So the biggest learning is your limits. Like, I didn’t realize I could get pushed to that point.

I didn’t realize I suck so bad at x. I didn’t realize I actually was good at this. Um, so the curriculum is fascinating. If you look at it, it has everything from boxing to a gas chamber, to swimming mm-hmm. To computer science, to philosophy, to [00:13:00] economics. Like you could not get more diverse. And let me tell you, everyone has to go through it.

Michael Mitchel: Right?

Casey Woo: That’s what’s unique about West Point and gaining a lot of confidence that unless something is life or death. Don’t panic. That’s one of the biggest things. And I’m in the startup world now where it may feel like life or death. Let me tell you, you’re good. Don’t worry about it. You’re going home.

Think you’re going home every day. Confidence.

Michael Mitchel: Yeah. Um, and so, you know, after Harvard, you’re in the traditional Wall Street scene, high finance, the New York Life City lifestyle, wall Street earnings. But, uh, it my, as we gotten to know each other, it seemed like you were probab. I get the impression you were personally unfulfilled.

So if that’s true, why or why not? What, what was missing? ’cause you, you left that scene.

Casey Woo: It was really interesting listening to your intro of me. I didn’t realize that. I did actually make, I think two hard exits in places that you’re not wanted again when you leave. Like, [00:14:00] don’t let the door hit you on the way out.

Michael Mitchel: I can see Wall Street like that. They seem very clique-ish.

Casey Woo: Oh yeah. And same with the military. And once again, not a bad or good thing, but it, so to me, uh, I’d be cautious my words here. I think. Um. West Point is a fraternity. I mean, it has women too, but you know what I’m saying? It it is that type of club.

It’s a fraternal,

Michael Mitchel: yeah,

Casey Woo: yeah, exactly. You know, obviously as, as, as women and all that, but you know, kind of this club concept. So I’ll just use fraternity ’cause it’s male dominated. But the other thing is Wall Street is a frat. Same thing has women too, but it’s male dominated. But it has this frat like thing.

And so I’ll, I’ll try to be short with this, but basically. At Harvard as an economics major, you’re told there’s two steps to Nirvana. Step one is go to an island called Manhattan.

Michael Mitchel: Mm-hmm.

Casey Woo: And get an investment banking job at Goldman Sachs and Morgan Stanley. And the subtext is, if you don’t, you’re a loser.

Right. So it’s kinda like, I dunno, med school or law school where you’re like competing. I definitely wasn’t the [00:15:00] smartest, but I had some army stories, so I realized just be different. Mm-hmm. And so I was like, lucky enough to get, you know, this. Small spots there. I went to Morgan Stanley and I loved it actually.

Funny enough, it was a hundred hour work week, et cetera, et cetera. I met half my groomsmen there, my wife I eventually met there. Uh, it was cool. The second and last step to Nirvana is get a hedge fund or private equity job and retire.

Michael Mitchel: Mm-hmm.

Casey Woo: And lemme tell you, it works. I have a lot of friends now who are doing just fine and who are very successful Wall Street professionals.

What happened for me is I got into. A very prestigious, uh, hedge fund. I was over the moon. This was it. I had a corner office or an office overlooking, central Park was a corner. I’m not sure anymore. Um, the, the office was bigger than my shoebox apartment almost.

Michael Mitchel: Hmm.

Casey Woo: I was covering consumer retail. So we’re talking like Under Armour, Victoria’s Secret fashion shows.

It was. There’s nothing to complain about. I was [00:16:00] 20 single Manhattan. Okay, here we go. This is what they told me about. I went from like cleaning weapons to like in a air quote coveted spot where I would get calls from friends who would say, how do I get into Wall Street? I mean, I was like, it’s, it is a very interesting feeder system.

You gotta go to certain schools, et cetera, et cetera. So I felt very fortunate. Let me fast forward a bit. Basically, after a little bit, I realized I was unfulfilled. At the time, it was hard for me to understand. Now, looking back, it’s crystal clear what was happening. I had three jobs, the military banking and hedge funds.

Why is it I actually did not feel unfulfilled in the military and banking? I felt unfulfilled in the one on paper that looks like the best. It’s because the first two are team sports. No one ever told me that. You look at money, you look at prestige, you [00:17:00] look at what you’re doing. No one ever told me, team versus individual.

I never even thought about it. But all of a sudden you stripped me from my team and you put me in a nice corner office where I talked to myself. Me personally, I started to wither and die. And that’s why I enjoyed the military so much. It was the comradery. And by the way, banking is a team sport. You’re a hundred hours work week next to your peers.

And I didn’t realize that’s what energized me. So despite the money and all that, and it’s a very challenging profession, there’s no question. It became, I miss my team, number one. The second is whether you’re a lawyer, consultant, investor, auditor, they share one thing in common is that they don’t, per se, build anything.

They transact and advise. Once again, I have a lot of friends. My wife is an investor, so I don’t mean this in a derogatory term, but it can feel like a treadmill. So the other thing I realized I love to do is build things. I realized that because I went to startup hedge funds that were tiny, and I started liking the building of the hedge fund [00:18:00] more than the investing, which is my day job.

So after 10 years, it was a very hard decision. ’cause my entire earnings, power, everything I worked for was pedigreed and like. Wall Street investor. Um, I left, took a big pay cut and joined a 10 person FinTech SaaS software startup, and became what I call an operating CFO. And I got my butt kicked, but um, I loved it.

From day one. And so that’s how I left Wall Street.

Michael Mitchel: So you’ve been a CFO several times. You’ve served as COO twice. How would you, I mean, there’s obvious differences, but how would you define the major differences between those two roles? Hmm. Because clearly you prefer the CFO side over the CO side. This my take,

Casey Woo: so, oh man, you know what?

I’m just gonna like be uncensored. I’m gonna talk about the COO role. Now when I talk about this, [00:19:00] I’m gonna talk about it in semi of a blanket statement, but clearly I don’t mean it that way. There’s Sheryl Sandberg and Tim Cook and all the famous COOs. I also happen to have co-founded a 500, now 600 person operators group, um, that has many COOs and CFOs.

So I, I have these conversations a lot. I see a lot of my friends what they go through. And of course, I was in the seat. So this is how it’s informed. A co is a very, very. Fragile, and you can almost say semi suicidal job. I’m being provocative here. Okay, so I’m not talking about the the, the Sheryl Sandbergs of the world, especially at early and mid stage companies, so we’ll call it sub 500 people.

Candidly, A COO is a gap filler. It’s for what does not exist. And so I’ll talk about that more. So that’s one. The second is it’s so dependent on the CEO, it’s like a very custom built role. The C Yeah. So one joke is, you know, if you’re, if you’re presented a CO job, there’s a [00:20:00] 50% chance something’s really messed up and you’re brought in to fix it.

You know, 50% chance they just wanna beef up the team. So there’s also just like, why do you need a COO? What happens in boardrooms, in my opinion, is do you have a founder, CEO, generally young. Generally first timer who’s brilliant, but all of a sudden as the business succeeds, they need to professionalize themselves.

Hey, there’s things called performance reviews and like proper budgeting, et cetera, and the board doesn’t have the power, you know, to force the CEO to do anything. ’cause they generally own all the rights. So what happens is you start to see things like, Hey, Mr. CEO, Mr. CEO, have you thought of a COO? Who can help you do all the stuff you don’t wanna do.

And of course they go, oh, that would be brilliant. And all of a sudden there’s a COO created. So that’s one potential thing. There’s many, uh, but my point is be careful why you’re being brought in. It could be a very difficult mission to begin with. The others, what I call the three and a half bedroom, a three bedroom’s called the [00:21:00] CFO four bedrooms called the CEO.

You eventually need to round up or down. And here’s what I mean. CO. I have so many COO friends. What do you do? Well, I run product, I own sales and they’ll list a whole bunch of things. I’m like, great, I’ll see you in one year. In one year. What’s going on? I hired A CRO. Oh, great. Did, weren’t you doing sales?

Yes, but it’s gotten big. Great. I hired a CPO. Weren’t you doing product? Of yes, but now we have a CPO. What do you do now? I think I’m an overpaid layer at this point. Did you just hire yourself out of a job? The answers generally if you succeed, the answer is yes, but literally hire yourself out of a job, not like metaphorically uh, and then you’re a big line item and then people wonder what you do.

The last thing. And there’s many, but the last thing I think worth pointing out about a COO versus a CFO is. Authority. It’s not a clear swim lane. And so you may start off and the, and the CEO says, all right, you have authority, [00:22:00] or we call the D, who holds the D, who holds the decision making power on, let’s call it sales or whatever.

Okay? Then all of a sudden everything’s cool until one day the CEO says, Hey, Mr. Mrs. COO, who made this decision? Oh, I did. I have the D, right? Yeah, but I don’t believe in it. So guess who really has the D. The CEO O so there’s like a false, I call it mom, dad, and people are gonna find out real quick, who has the power is a mom or is a dad.

And then you got another issue going on. And lemme tell you, if you get into a battle of the CEO, guess who wins, not you.

Michael Mitchel: Yeah. Okay.

Casey Woo: Um, and then the last thing is when you said difference CI strongly believe for the most part, the CFO is the right track if it makes sense for. What you want do. The CFO is becoming the COO.

That’s kind of the bottom line. The CFOs used to be Air quote, oh, is that the accountant? And, and once again, nothing about accountant, but they didn’t understand that it’s like that plus a lot more. Now it’s becoming truly [00:23:00] strategic, which is what COOs are generally for. So I think CFO is a proper swim lane.

Every company needs it. It’s very clear what they do. They don’t run into the CEO. They don’t hire themselves out of a job. So those are some big differences in terms of actual like career path. And of course there’s like, I can talk about what they do, but CO is like very varies by, by company. CFOI think is pretty standard.

Michael Mitchel: Uh, real briefly, how would you, how would you say that the role of the CFO has changed over the years? Because I, I know we, earlier we chatted about the difference between tactical and strategic. It’s almost as if I paid you for

Casey Woo: that. That’s, that’s something I strongly feel so great question. When I came to.

Silicon Valley from Silicon Alley and decided I wanted to do this job. I realized I went from the top of the totem pole in finance, New York to the bottom in Bay Area. I walked into a company, I’ll leave unnamed, but is probably one of the biggest companies in the world now. They were 60 [00:24:00] people. It’s an engineering based company or engineering led company.

Everyone knows about it. If I told them and I walked in and I said, I, I was told I need a job here. Any job. Except engineering. Don’t put me in engineering, but I don’t care if it’s a janitor. I’ve switched careers. I’m here to learn from the best about tech. And they said, show me your resume. And they saw all these Wall Street accolades.

And by the way, this is shortly after oh eight.

Michael Mitchel: Oh, right. Yeah.

Casey Woo: Oh man. I never would’ve thought everything I worked so hard for. It wasn’t just a neutral, it was a negative. He’s like, you are the devil. Oh my God, Morgan Stanley, are you the Goldman Sachs people? Oh my. You’re the devil you call. I was like, oh my God.

And I said, how about this, this 10 to a hundred person company I did in a, yeah, that’s cool. That’s legit. But it’s so New York. You don’t know what a real tech company’s like. At first I was like, that is damn pretentious. Just like finance is pretentious in, in your, you know what they were right just 10 years later, I [00:25:00] didn’t really know what a tech led company is, like a Facebook or Google versus, you know, et cetera.

So, but, and then they go, do you have a CPA? I said, Nope. Said, well, then you don’t qualify for finance here. And it blew my mind. I was like, wait a minute. I came from New York, which is like funding comes from 17,000 flavors. That just

Michael Mitchel: sounds like, like 1977 type thinking. It was, uh, not too long ago. Oh, wow.

Casey Woo: And the joke in Silicon Valley was there’s only three people that matter, the people that fund it, VCs, the people who build it, engineers, product managers, and the people who sell it. Notice they didn’t say hr, finance, legal, it. Translation, the back office. So I’m, I’m being a little bit facetious, but basically it was like, finance is a bookkeeper.

Once again, no offense to bookkeepers, but it’s more than that, right? Yes. We do that and more. And so I, I realized I was pretty lonely. And so this gets to your question of how the CFO has, you [00:26:00] know, role has changed, at least from the Bay Area world. So I realized that it was not only misunderstood, but I’d say undervalued.

And I happened to be invited to a lunch group. Of, uh, VPs of finance and BizOps and COOs, and I was like, oh my God, these are my people. I want to hang out with you and learn more because I don’t these engineers and VCs. It’s just kind of not my world. And honestly I’m a second class citizen. And that group, uh, we call it the Operator’s Guild, was this very humble seven person breakfast club I co-founded with, um, a friend is now 600 and.

Incredibly authentic and organic growth. But what’s happened over the last eight years for the role of the CFO, and I would even say HR people, is that it went from the back office to being strategic. So about five, six years ago, the word HR seemed to be banned from the land and it, you have to call them people.

Mm-hmm. [00:27:00] It’s a, I’m the head of people, not hr. HR was, you know, sexual harassment training a DP workday. It was this kind of like necessary evil Finance was also kind of like a necessary evil. I raised my series B and the VC said, I need a VP of finance. It was that type of language. Literally someone said that to me.

Mm-hmm. And then it flipped over time and over time it was like, you people is a big deal. Like it’s your talent. It’s, and so what happened is there’s a chief people officer, so all of a sudden it became front office strategic. Then of course, CFO over time became, there’s a difference between a controller.

People didn’t even realize that, and A CFO. And there’s a difference between a corporate CFO and A operating CFO, and there’s a difference between a strategic CFO and a non-strategic CFO. And that’s happened over time, where now you hear founders who are getting much smarter is yes, the, the bookkeeper is important.

I’m looking for a business thought partner and a strategic CFO. So that role has been [00:28:00] elevated significantly. And I can go more into why, but basically the coming out party is now and, and I think people that had a hard time explaining the value they could create is now, is now understood.

Michael Mitchel: Okay. Um, we work, I kind of believe was a wild ride.

Um, I mean, I can only begin to imagine what the, what the environment, the fast-paced environment was like, and I’m sure it was a crash course and everything. What was your takeaway from that experience and how has it shaped you as a, as an executive?

Casey Woo: Well, first of all, I’d like to say I think the most surprising thing, um, about WeWork is for people that are outside.

I tell them, I’m gonna make up a stat. But if you asked a 10. For every 10 we Workers ex WeWork, you ask, would you do it all over again knowing what you know? I think nine out of 10 would say hell yes. So I’m gonna start with that. I don’t think the Theranos people or the Enron people would say that. [00:29:00] So let, so the thing is, I think people get confused between this like fraud and like Bad, bad.

And basically a company that has a real business, it’s an amazing product that was mismanaged. That’s really what it is. It was, but in doing so, I learned a bunch. You know, number one was obviously the importance of governance. We all were told there’s governance and board rights. You know, you learn about it.

That was pretty key for WeWork. You know, it didn’t have the right governance. Um, or looking back, you know, I think SoftBank would tell you that. So just that subtlety makes an enormous difference in many ways. The second is the whole growth at all costs. You know, I think they were pushing the limits of could you do it where my, my analogy is, you know, can nine women make a baby in one month?

And the answer [00:30:00] is no. There is actual business physics. Where just because you have 10 x the money doesn’t mean you can 10 x it. It’s a really good reminder of things take time. Amazon took two decades to build. Mm-hmm. So even if you have the whole playbook, you couldn’t do it in two years, no matter if you had all the capital in the world.

So that’s a big learning. The other is do not underestimate visionary founders. I’ll have to give credit to Adam, despite all the press. WeWork would not be WeWork without him. I don’t think Travis would be Uber without Travis. By the way, we have many competitors. We were number one by far. Uber number one.

So in Silicon Valley you learn, you know, the Steve Jobs of the world, the Elon’s of the world. They’re definitely interesting characters. I appreciate that. Because if I was leading WeWork, it wouldn’t be WeWork. So you need that. Call it crazy, that visionary. So the other thing I learned is that power of a [00:31:00] storytelling.

The energy that was brought.

Michael Mitchel: Yeah.

Casey Woo: We were on a mission and that attracted incredible talent. That to this day is like a lot of my friends. And we had an amazing time learning, growing, um, and really attracting amazing people. And we did believe in the mission that we were improving people’s work life. So a lot of lessons from WeWork, but I think there’s also some misunderstandings.

Given the class. So is there

Michael Mitchel: anything that you could point to that from a skills perspective or, or, you know, what, how do I, um, say this? Yeah, maybe, I mean, as an, as an executive, what were some of the things that you could say, okay, I gained from this and I can apply it? I mean, it could be personal, it could be a, a specific skill.

I mean, I, I think that every experience we have. We take something away from it.

Casey Woo: Mm-hmm.

Michael Mitchel: So from a skills

Casey Woo: perspective, it can even be lessons learned. Yeah. Uh, there’s many, I’m just trying to be right, respectful of the, of the time here. [00:32:00] One is how to operate at hyper speed. So WeWork has broken many records in terms of speed for many financial metrics from any cash deployment, from et cetera.

Uh, we were gobbling up the globe in parallel across like five continents. It was insane. When you operate in something like that, it’s a very different learning. So where, you know, now I’m at landing, which is also hyper speed, but I, I can tell I’ve utilized a lot of the learnings to teach my team that have, have not experienced it.

So one of the rules is what I call 80 20. You need to get to zero to 80 real fast, but don’t spend too much time going from 80 to a hundred. Tomorrow, it’s all gonna change,

Michael Mitchel: right?

Casey Woo: So I think other people that may not have been in a slower environment, they’re, they’re like very focused on like polishing stuff and No.

So play it loose. You have to play loose and fast. But for some people it’s really uncomfortable to [00:33:00] have a rolling budget. To have a budget that doesn’t make any more sense in 30 days. And you gotta redo it, but yet you need something so that, that, that’s like times a thousand across. The thing is we need to keep moving the ball forward.

Iterate, iterate, iterate, um, make a call. It’s not, it’s not permanent. It, it can, it can scare a lot of people. It can be very daunting to a lot of people, the ambiguity. So I think that’s the number one skillset I learned is how to build fast, be flexible, but, but evolve in a very prudent way. Uh, you know, yeah.

Over time.

Michael Mitchel: Okay. What, um, what do you look for in, in an executive hire

Casey Woo: in all hires, I look for business first, comma function, second. In my general counsel business first, legal second in my controller business first, accounting second. It’s kind of the, you don’t wanna hire someone who’s a hammer and because they think everything’s a nail.

If you think about all the roles, all it is is serving the business. [00:34:00] It’s not serving the function. So the first thing is, does this person have a business orientation? For example, what, what is Yeah,

Michael Mitchel: yeah. I’m sorry. You’re about to ask what, what is your definition of, of business skill?

Casey Woo: Yes. So I’m gonna make it up.

Um, let’s say you go to the lawyer and you say, Hey, oh, here we go. Here we go. This is not the best analogy, but it’s like you go to a finance person and go, Hey, what’s the cash burn? Just roughly and maybe an accountant or fp and a like, hold on, let me pull all the bank statements. Lemme run my spreadsheets, lemme file out the cash burn.

A business person’s like, why don’t you just take today’s cash balance and minus it minus last month. It’s like, just get to the objective. What is the objective? Um, a legal one is I, I give ’em an issue or her, and the answer could be, we don’t need a 70 page contract for this. We just need to go shake hands with so and so.

Michael Mitchel: [00:35:00] Mm-hmm.

Casey Woo: And settle for a hundred bucks. That’s a business oriented general counsel. Um, if that makes any sense. So, so pick the analogy you like best, but basically what is the objective and what’s best for the business? It may not require my specific skillset or function

Michael Mitchel: mm-hmm.

Casey Woo: For this need. Um, but sometimes people that are not business first, all they think about is their box, their function, how they would spreadsheet the hell outta something.

Michael Mitchel: Mm-hmm.

Casey Woo: Um, and, and business first people were problem solvers. They can get themselves out of any situation, whereas, so I would call it a toolkit versus I’m a, I’m a hammer.

Michael Mitchel: Right. Okay. Cool. All right, excellent. What, um, do you have any advice you’d share to the next, uh, next CXO, next CFOC level general advice?

A peer or

Casey Woo: like an up and coming up

Michael Mitchel: and

Casey Woo: coming? Yeah, so I think two things. One is. When I [00:36:00] entered startups, I thought when I was reading about business books, I would read about business, and yet I realized, all I kept reading about were psychology books, HR books. I’m like, what? I don’t wanna be like an HR person or psychologist.

Number one is don’t forget what a business businesses, it’s just a bunch of people who’ve decided at eight in the morning to commit themselves to a certain other bunch of people to build something and sell it. Hopefully for more than it costs. It’s a game.

Michael Mitchel: Yeah. Business is a

Casey Woo: game that was created by humans with too much time on their hands.

Michael Mitchel: I never heard the phrase that, seriously, we don’t worry about

Casey Woo: getting killed like animals. Right? So we, we literally create this fun game called business and we take it like really? Seriously. So don’t forget, that’s what it all is. Translation. It’s about the people. The faster you can learn how to influence, motivate, hire, train, develop, deal with manage in out people.

Michael Mitchel: Yeah.

Casey Woo: You become Neo in the matrix. You, you elevate above it all and you’re like, [00:37:00] you don’t see numbers and revenue. You see people, and the last thing I’ll tell you is I accidentally have what I think is a superpower. I didn’t realize that has served me extremely well.

Michael Mitchel: Mm-hmm.

Casey Woo: I happen to build teams really well, so I have a lot of things I don’t do well.

I happen to just be able to hire, develop, put people in the right seats on the bus. Give them that autonomy, train them. Where I would, I wanna proudly say my track record, if you talk to my CEOs, is pound for pound, one of the most productive, efficient, well-oiled, happy teams.

Michael Mitchel: Mm-hmm.

Casey Woo: And so what I, when I, when I get, you know, when I get credit for something, oh my God, I was amazing to do this.

I didn’t do anything. My, my team did it. So my joke is, I’m the hardest working laziest manager you’ve ever seen. That is the, by the way, if you have that ability to build a team against something, you can do anything. You can do anything that, that’s like the real superpower. Um, I think the opposite of that, and this is the watch out [00:38:00] there are people, what I, who I call a Rambo, they’re so good, but they take everything on themselves.

Eventually Rambo loses the war because he gets overwhelmed. So when you’re starting off, it’s cool to be Rambo, but as you scale, become MacArthur.

Michael Mitchel: Echo’s echo. Yeah. Um, yeah. And, and as we kind of wrap this up, you know, the, there’s a question I always ask everybody is, what was the worst job you’ve ever had and what positive influence did you take away from it that you still use today throughout your entire career?

Right.

Casey Woo: I’m gonna use worse. Not as like, I hate it, but as in not fun. Um, it’s definitely at West Point, which I was a paid. Military cadet. I received a paycheck. And so that, that is a job. I didn’t realize it’s out of her job, but it is actually a job. Um, I learned a ton from it, and it was, it kind of goes back to it’s [00:39:00] humiliating.

I mean, they can really strip you down. You fail. You’ve never failed so much. You’ve never felt so embarrassed or inadequate. Um, but you come away. Realizing it’s gonna be okay. And then the other thing was not panicking. There’s one exercise we did where they gave us an impossible assignment. We knew it was impossible, but we couldn’t say anything by the way.

We could only say like, we’re basically mutes as freshmen, so they would assign it. We knew that we were in for it, but we couldn’t say anything and we just did it. And there was a consequence if you didn’t make it in time, it was like five hours of work into one hour. We didn’t make it. We were panicking.

We got punished. Whatever that was, you know. And then the next day they would do it again, except it was 45 minutes, same amount of work. And then six times later we got punished. Every time there, there was no let up. You realize we went from like panicking all the time to like, okay, we’re just gonna do our very best.

And so all you realize how much energy goes into panic. Panic doesn’t get you [00:40:00] anywhere. Use that energy. And by the way, we became so efficient, we almost got it done in 30 minutes. It was like the most insane thing. So you start to realize the power of focus and confidence. And you know what? Regardless if you panic or not, it, it is what it is.

So try your best to just not, not worry about things you can’t control.

Michael Mitchel: Cool. Excellent. Well, I’ve really enjoyed the conversation. Um, I, you know, as you can probably tell from the, from the, the theme of my questions, I, I find it very, I, I’m really intrigued and I find it inspirational that, you know, some people would view your West Point days as a failure.

I don’t, I think it’s incredibly brave, um, to, to make that hard call. Um, and you’ve done it more than once. So, um, I, I, I appreciate that you, you know, um. What, what you had to go through. I, I mean, I, I don’t know how else to, how to, how to say it. Um, uh, thanks for joining us on, uh, CXL conversations. Uh, for those who are listening, uh, you can find me on LinkedIn, Michael [00:41:00] Mitchell with one L at Denver, and I’m on Twitter m Mitchell with one L 52 80.

Um, and that’s Ted. Thanks for being on CXL conversations.

Casey Woo: Thank you, Michael. Thanks.