Balancing Career Ambition With Your Prime Parenting Years | Casey Woo (father of 3, founder of Operators Guild)

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Casey: I deal with entrepreneurs all the time. It's all about passion. It's all about what you lean to. You know, I want to solve this. They're leaning into it. You know, I'm a customer service person. I'm great at dealing with people. They lean into it.

You know, I'm a finance person. There's all these specialties. So my thing is very simple. Expose them to as many things as possible. Whatever sticks, double down. What gets you energized?

Whatever that is, just do more of it. But the prerequisite is do as many different things. You want to try to golf? You want to camp, you know, swim, whatever. And then finally I'll find it. And there's a pattern pretty quickly.

Adam-IntroOutro: Welcome to Startup Dad, the podcast where we dive deep into the lives of dads who are also leaders in the world of startups and business. I'm your host, Adam Fishman, and in this episode, I sat down with the founder of the Operators Guild, Casey Woo. Casey started Operators Guild to create a community of engaged ops professionals who help each other navigate the issues that come up when scaling a company.

In this conversation, we talk about how I came across Casey when he wrote a heartfelt post on the challenges of balancing career ambitions with your prime parenting years. We cover the pressures of being a father, the dichotomy of career and parenting, partnership dynamics with his wife, Laura, the joys and challenges of raising three kids, and how the value of time and his definition of success has changed as a father.

I hope you enjoy my conversation with Casey.

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Adam: I would like to welcome Casey Woo to Startup Dad. Casey, thank you for joining me today. It's great to have you here.

Casey: Thanks for having me.

Adam: Awesome. Before we get started today, I wanted to jump in and kind of talk about the thing that you wrote on LinkedIn, which is the thing that made me want to invite you onto the show.

I feel like somebody tagged me and it was like, Adam, you should talk to Casey. I'll link to this post in our show notes, but here it is. I'm just going to read it really quickly. You said, “I'm 41 and I love my work. However, I am increasingly struggling with balancing my prime career with my prime parenting years. I love my work as an operator, but my favorite and most important job is being a dad to my three kiddos under seven aka the hurt locker.” I like that by the way “by the time your kid is 12 years old, you've already spent 75 percent of your time with them. And I came across two different charts and immediately merged them in my head. It visualized my acute struggle these days. The two most important things in my life are merging at once. If you're in your 30s and 40s, you're likely in the prime of your career. It's easy to get caught up in the stress of work, putting out fires and focused on the next milestone. But it's important to earn a good income, fulfill one's professional goals, pay for vacations, provide for the family. However, and this is what I want to talk to you about, these prime hustle career years are the same prime years that my young kids need me the most, still adore and care to be around me, and when I can build amazing memories and bonds with them.”

So Casey, having said that, tell me about the inspiration for that post. Why did you put yourself out there so publicly on LinkedIn about this dichotomy that you wrestle with?

Casey: There's just a time in your life where you're like, everything's coming at once. When you're young, things come at you one at a time. I'm hungry. I need to eat. I have a test. And then it becomes, you know, college where there's multiple classes and maybe you have a relationship going. And then you all of a sudden it starts to peak at, you know, I'm 41.

You got three young kids. You're generally in the prime of your career. So there's you're known for something you got something going you got some confidence. You got a little bit of a nest egg and you can take risks. You can build. It's not just go show up to your job, learn, get a paycheck, right? So things start to get more open ended - possible - and of course just the surface area of everything expands and I just felt this pressure of, all these things matter to me, right?

Because what happens when you have a lot of things coming at you, you say, alright, what can I cut? And that's when the post was like, I mean, three kids are expensive, so I could theoretically do the namaste, I'm just gonna cut my work and manifest money.

I'm just a pretty practical person and I don't know how to do it any other way, but work hard to make money to just hand it over to my children.

My children are number one. But then there's money, right? Let's just call it what it is to provide for them. And then there's time. The money you can solve theoretically there's leverage in that, but time. So yeah, that's what inspired it. It was just, I want to do this. I want to do that. This weekend is that.

And you just realize you're suffocating on things and the calendar. And then of course, not being present, finding it hard to be present and things starting to break, missing this, missing that, that's what caused it, so.

Adam: Well, I appreciate you sharing that with the broader LinkedIn community. It's the thing that said, I gotta have this guy on the show. He seems very thoughtful, and I'm excited to have this conversation with you. So if we go all the way back to the beginning, tell us a bit more about your background.

Where did you grow up? What was your life like growing up?

Casey: So I was born in Hollywood, or Los Angeles, and first generation immigrant parents. Life was I guess we were pretty fortunate. You know, he's kind of middle class, very hardworking. Parents, my dad was like a real estate broker, mom was a jeweler. They all had to find new careers when they came from Taiwan, or that's always been really hard to think about, you know, if I just moved to like, I don't know, France right now and had like rebuild.

It's pretty hard. I was a pretty stereotypical, just very hardworking. I got really good grades. Work was my life. Life was, and yeah, work is my life is also like what you discover. It's sometimes it becomes your self worth, right? My family's culture.

The focus was work, education, and you started centering around that in terms of what value you bring to people, how you're respected, and looking back it's very clear that's where you put a lot of your energy is where things grow. So I did that. I went to the Military Academy at West Point. That's a whole other podcast we can talk about.

Then I finished my undergrad, so I actually did two and a half years at West Point and I did two years at Harvard. I think I'm one of maybe two people on planet Earth, something like that, that have that strange mix.

It wasn't planned that way, but it was pretty awesome to have two very different experiences.

They grew me a lot. And then from, as an economics major at Harvard, you're told there's two steps to Nirvana. Step one is go to an island called Manhattan. And get a banking job at Goldman Sachs, Morgan Stanley. I did that, met half my groomsmen, met my wife. I'm pretty good at Microsoft Excel. And then it was one last step, which was get a hedge fund or private equity job and retire.

And it worked. I got a hedge fund job. I'm still a member of the office overlooking Central Park. The office was bigger than my shoebox apartment. I'm like, oh my god, I made it. You know, I'm overpaid. People are wanting to take me out to steak dinners and all that stuff. And I just had to just do it for 10 years.

Just do it for 10 years and retire. That's it.

Adam: Seems simple.

Casey: Right? Just do it. And every year I got less energized by the job. Not because the job is not challenging. It's a, it's an incredibly challenging profession. But what I realized for me is I missed two things. And I said, why was I pretty happy in the military and banking?

Which on paper you'd be like, no, like those are the last.

Adam: Should be miserable. 

Casey: It's the Wolf of Wall Street, hedge fund, you know, Big Short. That's where it's happiness. And it was inversed. And it was inversed because I missed my team. So the one thing I will tell my kids is it's not about corner office. it's about the environment.

I strongly believe humans thrive in certain environments and you need to find what that is. Mine is not a corner office. I'm always outside of it. Why? I miss people. I don't want to be by myself. An the camaraderie of the military. I'm digging ditches, but I'm happy. There's no Central Park view, but I'm happy because I'm with others.

Building together, interacting. And the second is building. So building with teams. As an investor, lawyer, auditor, banker, consultant, for the most part, your job is to transact and advise. Unless you're building McKinsey, or building Goldman Sachs. You're transacting and there's nothing wrong with that, but for me, I felt like a treadmill and very often you'll hear people, you know, from consulting or banking that come over to the operating side, which is what I eventually did is that they want to own something, not advise, hand it off and someone else does something with it. The classic like consultants come in, hand you a deck thing. So after a while you're like, I want to do this myself and it's addicting. So after 10 years I quit, took a pay cut, a big one because you know, Wall Street's like just, an egregiously paid type of role and joined a 10 person startup and I loved it.

Definitely, you know, bank account took a hit and just had to readjust, but I was so energized. I was building with teams. Then from there it was, okay, this is what I want to do for a living. Is this, I don't know, I'll call it a CFO, COO, tech person, which I now just refer to as an operator.

My belief was if you're going to do something, go with the best star because that's how you learn.

If you want to cook. Move to Paris. You know if you want to film, move to Hollywood. Just the ecosystem will elevate you. If you want to do tech at its like highest speed and sophistication, go all the way to Silicon Valley, right? Just dive in. I did that. And found out the really hard way that finance in New York is the shit. Finance in San Francisco is shit.

Adam: Yeah.

Casey: Are you a bookkeeper? I'll never forget the line, do you have a CPA? Because if you don't qualify for finance here.

Adam: Uhhuh,

Casey: And I'm like, oh my. Qualify for finance? New York is just the land of finance, right? But there was a disconnect from, you know, 10 years ago, the tech world.

And once again, I'm stereotyping, right? But a lot of people, if you told them what's the difference between a controller and a CFO, they wouldn't know.

Adam: Right.

Casey: Or we say, what does the CFO do is they do budgets and like expense reports, right? They're just, the scope of it was just, I think not the widest aperture it could be. And I eventually found a job at a very like all engineering technical shop because that's what I didn't have. Oh, you just hang around business people all the time. You don't know what a real tech company is like. And I thought it was the most pretentious. And they were right though. There's a difference between a tech led company and a company that does tech.

And so I'm really glad I learned it. The coolest thing that happened though is along the way I was invited to a nine person lunch group with CFOs and COOs And I was like, oh my God, I found my people. Where have you been? It's just been VCs and CEOs and I'm second class citizen everywhere I go. No one understands this operating thing.

And I asked those nine people if they would like form a little group where we get together. Think of it like a mom, dad group where we help each other. And I set five roles because I was attending other communities and groups that I fought. We're off of it. So I kind of created the one that I wanted. That's a whole nother story, but basically it's called the operators guild and that, that nine grew to is now 800 and it's the full time thing with a full time staff and it's been one of the luckiest, coolest things that ever happened to me. In the meanwhile, just to get to the present, I've done six other, seven total startups from pre seed, A, B, C, D, pre IPO, raised a bunch of money, learned the hard way, a lot of things.

I've had to personally do three riffs, you know, nine payroll close calls. I was part of the crazy ride at WeWork. As a senior finance professional. It was an amazing journey, learned a ton, and now I'm much older. I'm now 10 years into operating and really focused on building the community at OG.

I also run a syndicate called Fog and just kind of feeling out what I want to do next. But that's my story. Sorry, it's a little bit long.

Adam: No, that's a great story. And along the way, you mentioned you met your wife, your partner back during the finance years, the New York finance years. So tell me about your, partner, and how you met, and then I want to talk about your kids the other love of your life.

Casey: Yeah, Laura is an amazing woman, it's one of those, you know, are you too lucky to be with someone type of thing. Okay, if you are, you should probably marry them. She was three years younger than me. We went to Morgan Stanley. She came as an intern, I was a second year. We just knew of each other then and then when I went to hedge funds two, three years later, she reached out on Facebook and was, hey, reaching out to all these Morgan Stanley alum who are in hedge funds.

Right. It's the classic, like I'm looking to get into this. Wanted to get some advice. I was like, you're beautiful. Yeah. I'll give you advice. Yeah. Let's, can we do coffee and advice? I had ulterior motives and yeah, long story short, we started becoming good friends, had a lot of fun together and you know, dated for three or four years.

Married in 2012, and yeah and that's how I met her. Oh I, I, I, actually the more interesting story is, the first time we've ever, she's ever seen me was a very fateful night. I was a first year analyst at Morgan Stanley. And, for those of you who don't know, at Mesman you work like 100 hours, literally 100 hours a week.

And, we're in a cubicle, and the second year turns to me, his name is Brad, and he goes, Oh man, I just got staffed up. I can't go to this NYU recruiting event. So the way it works is you go back to your school. And he goes, hey, can you go for me? I'm like I'm not an NYU person. I don't even know. And he says, yeah, whatever.

So I went. And I was like this black sheep, this Harvard kid sitting in the middle of NYU folks. And they're wondering, why am I even here?

And I try to be really helpful by telling people that in banking, you know, it's, there's quotas, there's school teams. It's not as evenly meritocracy, as you would imagine, and just kind of showing them the insides.

With the hope of saying, hey, if you don't get a job at, you know, one of these firms, it's not you.

It's not like, oh, you couldn't make it. It's, you know, it depends on where you went to school and things like that. Not a good idea to do that. I should have just been quiet and I remember them asking well how many spots are there for NYU kids at Morgan Stanley?

And rather than saying no comment or I don't know, I wrote I said zero to one.

Adam: Oof.

Casey: And this is a form of, I don't know, 300 NYU Stern, ambitious, talented juniors looking to get an internship. And I just told them, an internship's really important and going to the right bank is really important.

Adam: And that they're not going to get one at your bank.

Casey: I mean, when you hear zero to one, and that's a pretty hard thing.

And I, but my whole point is, hey, if you don't get it, it's not 'cause a you like, just know that it's a little bit of a crap shoot, whatever. Fast forward a year you know, six foot tall girl came to me and knocked, you know, tapped me on the shoulder and said hi. And she goes, hi, do you remember me? I was like no, because you spoke at NYU,um, and I'm that one.

And that was hers. So that's how we knew of each other. Yeah. But that's how we met.

Adam: Yeah. And yeah, so you have three kids now if I'm not mistaken. Tell me about your kids. How old are they? Boys? Girls? What do you got?

Casey: My kids are seven, five, and three.

They are the best thing that ever happened to me. boy, boy, girl,

you can probably imagine after the two boys I really like a girl.

I'll just say it. There's no shame in it. Three boys is cool too, but you know, one of each is really fun.

Adam: Yep.

Casey: And got super excited when the balloon popped pink.

So yeah, they're crazy raccoons. And I just love watching them in terms of, you know, you get to see obviously their personalities, the way they interact. When you have three kids, they start to create their own unit and how they interact. Its super fun. And what I love most about any person I meet, let alone my children.

Is what's their superpower?

Everyone, I'm going to write a post or whatever about everyone's got a PhD. Find out what it is. So yeah, and I can go down, but basically, you know, one's artistic, you know, one's just, you know, super sharp, manipulative, extremely strong willed and confident and fearless.

But I love seeing that.

So yeah, so that's, and we, you know, we live in Marin, just north of the Golden Gate Bridge.

Adam: Very nice.

Casey: An incredible place to raise a family, very fortunate. And they're doing the whole school thing now. We found our groove out of, you know, all potty trained, right? So we're like, finally, one foot left in the hurt locker.

Adam: Yeah.

Casey: We’re almost there. And then my daughter celebrated her third birthday yesterday. 

Adam: Oh, happy birthday.

Casey: We're getting there. I think we're about two years away from like, semi self sufficiency. But yes,

Adam: Just turning them loose in the wilds of Marin and saying, we'll see you at dinner time.

Casey: Yeah, my wife will probably, yeah, not that quite open, but yes not all eyes on them every second.

Adam: Yeah. You said Laura is your wife's name. So she started in finance. She obviously made her way to Morgan Stanley. She's just to prove you wrong. What does she do now? Cause three kids is a lot of kids. So how do the two of you make it all work?

Casey: Yeah. She's at a high powered career in finance, which is also an accomplishment because I mean, let's call it what it is being a female in a male dominated thing is not easy and hard. She did extremely well. She went to Maverick capital for about 10 years and had a really good run there.

Then went to a multifamily office. So she started moving into kind of family office investing and now she's at Innovation Endeavors. As the head of IR which is anchored by Eric Schmidt. So she has a really cool job where she gets to meet some of the coolest entrepreneurs, you know, doing some of the most bleeding edge stuff and yeah, she's loving it.

So she has this like this little startup-y, right? Like when you think about you know, a VC shop it's been around four or five years, very successful, but there's a big difference between corporate life and she's watched me go through the crazy startup life. And I'm very happy to see her just love her team and the impact she can make, right?

Stepping away from investing and kind of being a part of an operating business. So, yeah.

Adam: And so the two of you are both in pretty... You know, serious careers, right? I'm sure Operators Guild keeps you super busy. I'm sure your wife's super busy. Tell me about the decision to start a family. Two hardworking professionals, not a lot of free time probably, and now you have three kids. So what was that conversation like?

What did it take to kind of get you both to that point where you were ready?

Casey: This one's an easy one. Our first date, so to speak, was how many kids do you want? She’s like four. How many kids do you want? Four.

Adam: Oh, wow.

Casey: So, we 

Adam: Oh, you're not done yet.

Casey: ah, that's a different story. I think I think three's the new four. You know, obviously we're older. It was an obvious, you know, kids are a very big part of our life.

Regardless of whatever we're doing, no time is a good time. You just had to like do it, right? Because the other thing is just time, energy, time and energy. And if you want to have three or four, you need to like back into it, right? She's German. Like there's a, you got to plan it. Okay. Two years apart.

I think that was a little bit of like, you know, just enough spacing, but not so much that we're going to be parents forever. So, yeah. So, and then of course, when the third was super healthy and we got the girl, it was enough. And also, we don't, we live in a relatively expensive place to raise kids, right?

So there's a whole bunch of factors, and more importantly, it's just our age and energy.

Adam: Yeah. Chasing around three kids, seven and under is not for the faint at heart.

Casey: A more interesting question is if, I was stressing really hard on the third gender reveal,

Adam: Yeah.

Casey: if it hit blue again, I can't speak for her, but the odds of a fourth would go from 5 percent to 25%,

Adam: Oh,

Casey: Right? And then you have, and then you end up with seven boys, you know.

Adam: yeah.

Casey: So, There's just this like, count your blessings, BOOM!

Like, three is just like an overflowing pot. And to us, we love just the energy, the holidays, the family, right? And at three, you've got there. At four, it's just a whole nother ballgame. But we just consider ourselves lucky and, you know, as she calls it, the bakery is closed.

Adam: Bakery is closed. I love that. What's the earliest memory that you have of becoming a dad?

Casey: Oh if dad meant seeing my kid versus, you know, her being pregnant, it's absolutely, we'll never ever forget. When Henning, our first, was born, the most incredible, exciting, you know, just having contractions, like that is like, I wish that upon every person to be able to experience, meeting their child is the most, whatever you're looking forward to is very few things that I think will top meeting your child first, second, third, fourth, doesn't matter, but yeah, absolutely. It's the hospital. It's seeing him. It's just flooded with love and the responsibility, right there. It just kicks in.

There's like this, I'm gonna take care of you and love you and keep you safe. And he's obviously just adorable. So yeah, that was the coolest. Yeah, no question.

Adam: All right. When we kind of prepped for this call, one of the things that you said you wanted to talk about is what you call the honest reality about work life balance. And you put balance in quotes. So what is that reality for you?

Casey: I'm probably not the best person to take advice in this category, but for me... You know, when I heard initially this whole like you know, nine to five, it stops here, then do this. I think there's a little bit of truth to that, which is blocking time off. Like, for example, my kids are at school now. So, well, yeah, then you work.

So there's definitely that black and white on and off. But I think the whole, for me, never touching a work email during the weekend is not my reality.

Adam: Right.

Casey: What my reality is when kids are not around.

If they're sleeping, at 7 o'clock they go down, 7:05 go ahead if you want to go do whatever non kid stuff that you think is important.

Whether it's socializing with your friends, whether it's work to catch up, I do it.

Now part of that is me, I think, over committing and overloading myself. So you can also just have a work that's not as much volume of stuff and you might be able to fit it in the air quote nine to five.

But my point is it's work, work life flow, not balance.

And it flows. If I'm traveling, extra amount of work because I'm not with my kids.

Adam: Yeah.

Casey: But there's no kind of, for me, a very nice clear boundary.

And as I say that part of me is just me, right? Like I've seen very successful people with very heavy jobs. Have a cleaner balance.

I think part of it is them.

They can just shut it off.

Adam: Yeah.

Casey: So I'm very self aware that I don't have an easy shutoff valve. And that causes a lot of it, right? If you don't have easy, you know, what they call meditating, whatever, where you can just take thoughts and move them away, you're likely going to integrate work with something else or not be present enough.

So I'll fully admit, I'm not saying work/life balance is not possible, I'm just saying, for me, it's, I still got a ways to go.

Adam: How do you explain what you do to your kids? Do they have a good understanding of what it means to run a community of operators?

Casey: I love this question for kids, no matter what age, kind of don't ever know. And it's. My kids are probably too young to even care. They just know that I go into the office shed and smash a keyboard. Oh the phone. Hello. Hello. Hello, which is really cute. I think there's something really cute about kids who I mean they hang out with you all the time, they know you better than anyone… Who have no freaking idea what you do for is in the time because you don't talk about it, you don't bore them with it, so the answer is I don't think they have any clue.

Adam: Yeah.

Casey: It's too complicated in that sense. I'm not, you know, a plumber, or a driver, or something a little more straightforward. It's even hard to describe community to you. Let alone, like, to a, you know, seven year old.

Adam: Yeah.

Casey: But yeah, they definitely know that we work hard. And they've definitely gotten the connection of, like, the sweetest thing was my son.

He's like, hey, dad, like I it's just fake money. And he gave it to me. And he's like, now you don't need to work as hard and you can spend more time. And I was like, oh my God. And because sometimes I joke, they're like, where are you going? I got to work. You got to go to school, right? That costs money, you know, or that toy you got that costs money.

And kind of telling them that I'm doing this for them. Not just like I have something better to do that I don't want to be with them, but it's. It's a responsibility to take care of them.

Adam: Yeah. One of the things that you mentioned, I want to follow up on that, is, you mentioned that you love work and you love your family and I can tell that you're a person who really gets a lot of satisfaction from running this community that you do and it seems like it's very valuable for a lot of people. So one of the things I'm curious about is, you know, you and your wife both have careers and you have three kids. What sort of rituals or what do you do to find time to spend with each other?

Maybe independent of the kids or are the kids integrated into that? I'm always very curious to hear how people do this with many children.

Casey: The short answer is it's been tough. I mean, there's, of course, you always have the scheduled date nights. Help, to be quite honest. We have an au pair, we've had a nanny before. We just, you know, the trade off of both working is you have an income enough to hopefully hire help. It’s kind of the trade.

And that has helped a ton, which is a live in au pair who's amazing.

So, and then, of course, a stable of babysitters. So if you want to go out at night, so one is also not only with us, but it's with our friends.

So I think one thing that we stumbled upon, which is great, is doing something for ourselves.

You know, I have an air quote dad's group. She has her mom's friends and the community. So when you go into school, right, you have a community, you start to have a lot more friends in common. So I think we, I love it when she's like, I have a girl's night out, I have a, you know, dads get drinks, whatever it is.

And so the babysitter or we trade off. But the big one is very simple, which is a very strict bedtime.

Adam: Yeah.

Casey: We're on the earlier end, which is 7 PM

Adam: That is pretty early. I would love if my kids went to bed at seven.

Casey: It is. Starting to push to 7: 30, I told her, hey, we can't put into seven all the rest of their life.

Adam: Right.

Casey: But when we moved from a 9:30 as rookie parents and someone said, what are you doing? 9:30? Put them down earlier and said baby, all of a sudden the world opened up, right? Cause you got whatever, 7:30 to 10:30 to do adult stuff.

A big one was literally time you put down kids. Making that a routine. Otherwise you're just exhausted. Like you have no time for yourself. You're just going to bed right after. And then the whole cycle just breaks you.

Adam: It's encouraging to know that you can in fact shift the bedtime in the direction that you want it when they're young. Moving from 9:30 to 7:30. That is like a, that's a feat of accomplishment there. That's great.

Casey: Yeah. You rip their nap away. You run them down. Yeah, I will say they wake

Adam: doing laps in the yard.

Casey: Yeah. I, yeah, they do wake up early though. So there's a trip, but that's a better trade. 

Adam: Yeah, 

Casey: You wake up early than to put them down late.

Adam: Did some West Point drills with them where you're doing burpees and things like that to wipe them out. What are some of the most surprising things that you've discovered as a dad? What's really like, blown you away about fatherhood?

Casey: Just how fast kids pick up on things.

Adam: Say more about that.

Casey: Just how smart they are. My eldest can draw better than me, you know, and I have you know, 38 years on him. They're just born with certain tendencies that are just I think really special and of course, I think how they see the world, right? It's such a fresh just like the whole money thing.

You know, I found some money. Can you stop working? It's just very basic things. The other thing just how sweet the whole innocent sweet children are I think that never gets old

And also their innate understanding of caring as a human. The cutest is my daughter, right? She's the youngest of all of them.

At the age of one, you know, she could barely stand, but if her brother's crying, you could see her immediately stop the bickering or the fighting over the toy and come and, like, starts to, like, pet his head. That's just like, or she walks by a dog. Yeah, I'm sorry, the stereotype, at least for, in my I gave her trucks, didn't want them.

This is like one years old, right? And then she loved the dresses, and doggy, like just wants to like love dogs, and the dolls, and there's just something so sweet about what you're born with.

Adam: Yeah.

Casey: And this goes back to PhDs, you know, like just that's your thing go, lean in. But the last thing is like my eldest is so imaginative. They only have the same toys, right? They're trapped in a home with the same toys all the time. Wherever he goes somewhere, you know, call it train town or whatever, the next hour he’s back he's grabbing anything in the house to recreate whatever is imagined. It's a train town. It's a, we took a ferry and he used magnet tiles and a one of those portable lights and he put it in and then lit it up and goes, look, it's a lighthouse.

Adam: Ah.

Casey: And I'm just like far more creative than me.

Adam: Yeah.

Casey: That is the stuff that has surprised me about kids.

Adam: So I want to touch on that PhD topic again, because I think that's an amazing way of thinking about kids. All having a superpower. What have you done to lean into the strengths or the fascinations of your different kids? How do you encourage it?

Casey: Yeah. Great question. I, this is where in my life, when you think about, I deal with entrepreneurs all the time. It's all about passion. It's all about what you lean to. You know, I want to solve this. They're leaning into it. You know, I'm a customer service person. I'm great at dealing with people. They lean into it.

You know, I'm a finance person. There's all these specialties. So my thing is very simple. Expose them to as many things as possible. Whatever sticks, double down. My eldest is art, imaginative things and of course, it's toys that build. Audio books, where his imagination's reading, right? So things that just, get him an art teacher.

The thing is, he's been fired from almost all of his, by all of his teachers, so to speak, because he's like mad scientist. He gets so caught up in his stuff that when you teach him like the fundamentals of drawing, he's like, I don't care.

Adam: Yeah.

Casey: Like talking about some anyways, so leaning in just more opportunities to grow the imagination and then of course play with him.

Yes. And then what happened? And then what happened? So as simple as that for my middle Bates, he's just the athlete. Built like a gymnast, can throw harder than his older brother, more accurately, picks up every sport, rock climbs. So that's what it is. He loved rock climbing. He like, you see the smile on his face.

That's it. I'm going to go try to get a belay certification and we're going to go to the rock climbing. That's really what it is. And my daughter's a little bit too young to tell whatever makes them laugh. And what I call is energized. I don't think the strengths and weaknesses, what gets you energized?

Whatever that is, just do more of it. But the prerequisite is do as many different things. You want to try to golf? You want to camp, you know, swim, whatever. And then finally I'll find it. And there's a pattern pretty quickly.

Adam: Yeah. Yeah. That's a fascinating way of thinking about it. I like that kind of exposing them to the broadest possible set of things you can. And then leaning in. Broad and then deep. Okay, more of a fun question, but what is your favorite book to read to your kids?

Casey: Oh man. It's actually, a search and find book.

Adam: Okay.

Casey: I have a very short attention span, so it's very sad, but it's very hard for me to read Grapes of Wrath to them. Right. It's gonna be something that has a lot of stimulus. So, I'm the tickle monster dad. I'm the throw around dad. I'm the, I wanna hear you laugh.

I wanna know you're having a good time. Less cerebral, you know, just making up stories and talking in a soft voice together. No, it's just more straight up like throw me on the bed, you know, like and so the book is a search and find book where what I do is one boy's on the left one boy's on the right and they're supposed to flip the pages.

And then I'll say, okay, find the crayon and I'll start counting down three seconds. And if they don't find it, they get tickled like crazy. And they just love it, or they don't turn the page after I finish reading something. They get tickled. There's just like suspense and they just love it and they can't get enough of it.

And so to me, it's very engaging. But I'm not reading much.

Adam: Hey, that's okay.

Casey: Yeah.

Adam: That’s ok, when they're older and they, and somebody asked them, what was their favorite book? That's going to be the book. So what about the opposite? What is your least favorite book to read to your kids? Probably the Grapes of Wrath.

Casey: Yeah. Anything that's just all text, very few pictures.

Yeah, I hate to say it, it's just these like, very dense, the more closer it gets to a novel, and you know, I hate to say it, I'll lean toward audiobooks then.

Adam: yeah. So War and Peace stays on the shelf. You're not you're not getting that one.

Casey: Yeah, but to be fair, I think it's very important for these, like, denser books. It's very important, and I cheat with audiobooks. Which, I tell, it's different than a dad reading, but you know, they have way more command of the narrative, and it's fun, and it's like, you know, my intonation late at night is like, and then, yes, he was very excited, said, you know, said Sally.

Okay, you know, and that's just not fair to them,

Adam: Right.

Casey: But they love the audiobooks, so that's really what we're leaning toward.

Adam: Yeah, that's great. Have you or your wife developed any particular frameworks or guardrails from, for parenting that make, that you can kind of rely on or lean into when you need?

Casey: This is a, I think, a very common one, and what I call brilliant basic, but just routine. There's a safety in routine, there's a way to survive through routine, but also a little bit of discipline whether it's, you know, we got five minutes before we got to get out the door, everyone, so you need to get dressed and it's just that consistency whether it's going down at a certain time. The biggest one is, you know, if it's one treat you can have per day or whatever, you got to try to stay with that they will rip you to shreds once they discover it's a moving target.

Adam: Yeah,

Casey: Consistency.

Adam: Have you tried any of the parenting tools like the routine chart or like drawing the pictures of the activities that you want them to do in the morning. I don't know if this is a thing.

Casey: Well, this is where you come in. There's probably, I would love to, there's some advanced level things that you've collected that I would love to subscribe to. We are very rookie at pro tips. We just kind of are the basics and trying to survive. I would, I would love to hear what, what people love.

Adam: So I cannot claim credit for this one But the best one that the most creative one that I have seen works when your kids are a little bit older and every day you know They've got a different activity or they need to bring something to school with them as a family that I know that basically dressed their kid up in the outfit and with the instrument and with the whatever else that they needed for every individual day of the week and took a picture of their kid and blew it up and they have it at the exit of their house.

And so it's like, it's Monday. Baseball uniform, trombone, whatever, soccer cleats. And you can see it on the kid. And they have three kids, just like you. But all of them a little bit older. But I thought that was very creative. Whether or not it works, I do not know. But but I thought it was a neat it was a neat technique.

Casey: They basically visualize and execute, essentially,

Adam: Exactly. Cause then the kid's like, what do I need? I can go and look. I don't have to read. I can just see my picture. So probably works at all ages. Probably would work even as young as three with your daughter. So. So partnership, I want to talk about that for a second. Partnership is super important when you have kids, especially in your case when you're outnumbered by your children.

But it is also hard to agree 100 percent of the time with your partner. So what is something that you and your wife don't agree on when it comes to parenting?

Casey: There’s a lot. She will tell you. I'm much more of a laissez faire, a little bit more cool with more stuff. I'm sure that happens in a lot of relationships, or one's a little stricter. Probably not a great answer, but the real answer for us is we've fallen into things that, where she's more strict about, she leads.

Now, unfortunately, when you're stricter by 90%, you start to lead the charge at 90 percent of things. I try to do all the, you know, non kid stuff, right? Like, so the other one is splitting time. That allows us to actually have our adult time too, or whatever we got to take care of. So there is like, hey, go to go with dad to the park to ride the bikes. And then mom gets to sleep in. So we trade mornings. Translation, you kind of just parent, allow them to parent the way they want to parent without being together in like, because otherwise sometimes it's just, you start to focus more on the other parent of how they're doing it. Which is, yeah, and then there's also when you think about it with.

There's also a benefit, of course, when both of you are there, but it also means that both of you never get a break. So, that's what it is. A splitting time. Do you have bedtime? Cause the other thing is, they start to play off one of each other.

I want mama to do it. I want, well, there's only one right now.

Dad has stepped out for a walk. So, it's me. clearer, you got it, I got it, like, leads. And of course, like anything you have to agree on whatever the new rule is, one treat or, you know, screen time is only this and then just stay consistent. So, but I think the splitting time has worked really well on weekends and then he goes, we'll come together in the afternoon, but in the morning you have, and I think that's worked pretty well.

Adam: I think that is a great unlock for parents, to be honest. And one of those things where I don't think a lot of parents start out thinking that way, where they're like, no, we have to do everything together as a family. And then they're like, why are we miserable all the time? And then they realize like, oh, we don't have to be in the same place.

We can split so somebody can get a rest or something like that. Sounds like you've nailed it maybe even earlier age than I figured this out. So, that's a great one. I wanted to ask you another thing that you mentioned, and I love this analogy. You talked about this concept professionally and personally of cash versus lotto tickets. And so, say more about what that means. What does cash versus lotto tickets mean for you professionally and personally?

Casey: You know, for the last decade, I've been in high growth VC backed companies.

I love the venture world because it takes that type of bet when nothing is certain to create incredible things to innovate, even just like, you know, ChatGPT, right? I mean, when the investment was going in there, there was no product now meaning for certain types of innovation and bets and risk taking or R and D this idea of, you know, spend money and I'm not sure when the profit comes.

And go fast, you know, you gotta break through or disrupt because time is money also, is wonderful.

I think for a lot of people in this world, they forget that there's another world, the pizza shop. No, the pizza shop should not get VC money and, you know, build out 100 pizza shops tomorrow. That's, business does not work that way. Developing AI products does. So that's why it's normally tech. It's not a surprise.

It's not coal mining companies that, that, that use VC money. So I'm a student of business where different investments and different tolerances are designed for the actual business. So because of all the hype and then obviously in 20 and 21 and just there was so much frothiness of everyone gets money. But of course, what happens? There's a price to pay, right? Is you pay too high eventually comes down, but there's a cash burning tendency. There's a mixture between taking a calculated bet and we don't say burn, invest money. And then there's just burning money, right? So there's this very weird world where when it got too frothy, people started to forget about.

What is a business in terms of a shareholder return? Cash flow. At the end of the day, all things lead to, air quote in theory, the discounted cash flows of that business. Cash that comes out to be able to be distributed and used. Otherwise it's called charity. Right. But it's a simple thing that people forgot about cash flow because we're in the early stage of things.

Right. And the reason why it's reminded me, cause when I was my East coast days, New York, it was all about cash flow. I was a public investor is Walmart spits off cash, Apple. There's something to hold on to and value. And the valuation is more accurate because you're as close as possible to potential cash besides selling.

On the other side, it is the farthest possible from cash. So don't forget about, there's businesses to respect that may not be some like 100x lotto ticket or super sexy AI. And this is my line is, you know, nannies take cash.

Last time I checked, you can laugh at the boring companies spitting off cash. That cash pays for groceries. It sounds like a weird thing, it's like, no crap, Casey. Just, there's like brilliant basics of, because we get caught in this world of multiples, and my equity is worth X, and it's almost like an illusion sometimes. And sometimes it works. And sometimes you're left with a bag full of paper that the nanny doesn't want.

Or whatever, I just use nanny. I say nanny just because I spend a lot of money on childcare. But you know, you pick your whatever, gas station.

Adam: Your mortgage company.

Casey: Yeah! I bring it back to the basics of like, We try to get all like mission oriented. That's great. And then there's just like, what are you working for? Well, to be able to pay for the vacation or for the school or, so anyways, don't forget about, there's a big world out there. That's focused on cashflow and being profitable and don't get it mixed up with everything's got to be some rocket ship.

Adam: Yeah. That makes a lot of sense. I love that phrase, nannies take cash, not stock options.

Casey: Yes. Oh, great. Your stock options are wonderful. Cool. Cash, please.

Adam: Okay, so besides those stock options or those lotto tickets, what is something else that you've had to give up to become a father?

Casey: Definitely social life and time. And when I say well, I just mean less. I definitely am lucky that I have, you know, my guy's trips and all that. Definitely it's time to do stuff for myself. There's a post I'm going to write, it's the three standard deviations. And someone's like, you know, kids are just standard deviations of social time. Your first one is one standard deviation takes up, you know, whatever it is, 68 percent of all your social time that you had before the kid, which is like bearable, right? Cause you got a third left. That's my first kid. Okay. The second kid will crush you. The second kid chokes you out at 92 percent or something like that. And that's when you feel it.

Adam: Yeah

Casey: And the third is at that point, whatever.

Adam: You're right.

Casey: Yeah, and so, so this is why, that made more sense to me than like, you know, oh, three is really hard. No, three is just very incremental. Two. Moving from one to two. I was like, why is that so hard? Because, you know, you would think zero to one is hard.

One to two to me was way harder. And it's that, it's this, when you suck away your rest time, recharge time, you time, that's hard.

Adam: Yeah. That one plus one does not equal two, actually. It's actually more like 50.

Casey: That's right, exactly right. It's an exponential type of squeeze out.

Adam: I never thought about the standard deviations. I'm looking forward to that post. You'll have to share it with me when it comes out. We'll link it in the notes if this isn't out yet. So, okay. Last couple of questions for you. What's a mistake that you've made as a father?

Casey: I really am hard on myself when I'm not patient with them.

You know, cause there's life and there's calendars and you're late for the meeting and we gotta go to the drop off and I'll catch myself at times with like, it's not just all about your schedule. You know, but there's of course a pressure.

You got three of them and look, we got to get to school, you know, but slowing down and saying, you know, what? all right, I guess we're gonna be late today and you know, you know, what's the matter? Let's talk about so it's like that's hard when you balance all this and you get too abrupt with them you get I always look back.

I thought that was mean. I don't like that I don't like the way I was so abrupt and hey, let's go right now. You know one of those things I want to reduce that and just I don't know, make it a little softer. But it's because of the anxieties of someone's waiting on a call for me right now. I mean, I need to drop you off, right?

But that's just, then you think about their world. That's not their world, and it's I never want to be that too busy of a dad.

Adam: Yeah. Yeah. No, that makes, that's profound. That makes, that makes a lot of sense. Okay, before we get to my rapid fire round, which is always a treat I wanted to ask you, how can people follow along on your journey or be helpful to you?

Casey: Well, I mean, I try to share a lot of the learnings from the Operators Guild, which is It's 800 going to a thousand of the best company builders in the world. And you know, when I write on LinkedIn, so I think follow me there for stuff. Obviously if you're an operator, Operators Guild it is one of the most incredible organic powerful communities for company building that I think is out there.

And then the Fog Ventures. So Fog Ventures, Fog stands for Four Operators Guild.

Adam: Oh, I like that.

Casey: It is an extension of Operators, we are the, one of the best top operator syndicates in the world. And we get to really pair up with tier one companies to invest in them because there's a trade for company building, distribution, brand awareness.

So yeah, I think signing up for those would be amazing. And of course, you know, send me a note if there's anything that I can help with. But I'm very fortunate to have a full time job right now of helping people.

Adam: Yeah, that's great. All right. Are you ready for the rapid fire round?

Casey: No.

Adam: Is anyone ever really ready for the rapid fire round? I think the answer is also no. Here's how rapid fire works. I ask you a question. You respond with the first thing that comes to mind. No chance of correction. We're just going. We're going. 

Casey: How many are there?

Adam: Oh, there's about 15 or 20.

Casey: Oh Jesus.

Adam: We're going to rip through these real quick. They're fun. We, I have a lot of fun with the rapid fire round though. Okay. If you're ready, here we go. Casey, welcome to the rapid fire. Welcome to the ring. Question number one, what is the most indispensable parenting product you have ever purchased?

Casey: Umbrella stroller.

Adam: What is the most useless parenting product you have purchased?

Casey: The big stroller. The way too big stroller.

Adam: You have three kids, which one of them is your favorite?

Casey: Daughter.

Adam: Most frustrating thing that has ever happened to you as a dad?

Casey: Pass.

Adam: Oh, I was gonna say it must involve feces or something

Casey: I literally was going to think, so I was, but then I was sort of making up a story, so if you want me to, I don't remember exactly where it was, but It's, yeah, it's just pooping all over their pants. I don't remember the context, so I didn't want to just say a random thing. But it's definitely feces.

Adam: As a follow up, where is the strangest place you have ever found a diaper?

Casey: Oh, you know, under the seat of a car, you know, after three years.

Adam: Oh God! How many parenting books do you have in your house?

Casey: Five.

Adam: How many parenting books have you actually read cover to cover?

Casey: And I said, please don't ask me how many. Okay, zero.

Adam: Least favorite age for your kids.

Casey: One.

Adam: Okay. Best age for your kids.

Casey: Seven.

Adam: All right.

Casey: This is all I know, by the way. Ask me later.

Adam: Everyone always says the age that they are right now. What is your take on minivans?

Casey: Super practical, functional. My wife would not be caught dead in one.

Adam: Blaming the wife. Okay, I see how it is.

Casey: To be fair, I also would, I would drive it, but I, there's other ways. SUVs are cool.

Adam: What is your policy on snacks before dinner time?

Casey: Before? Zero.

Adam: What is the most embarrassing thing that you've ever done in front of your kids?

Casey: Oh, man. Dance.

Adam: Ok. It gets a lot easier to embarrass your kids as they get older. I'm just going to tell you.

Casey: Oh, is to embarrass them or to, that I'm embarrassed of?

Adam: No, for you embarrassing them,

Casey: Oh nevermind. Oh, I know. One time I came in to my son's kindergarten and I was volunteering for lunch. I was like, hi, Henning! And you could see him side eye and slowly move down and hide in the bench. I was like, I've become that dad. I've become that dad and I didn't realize. I was like, what do you mean, hi? And he's like, can you go away right now?

Adam: He's going to love it when you drop him off on his first day of high school. Have you ever pretended to be asleep to avoid a middle of the night wake up?

Casey: Oh, hell yes. Yeah. Right now.

Adam: What is the most absurd thing that your kid has ever asked you to buy for them?

Casey: A gun.

Adam: What is the longest that you've gone without bathing your kids?

Casey: Mmm. Two days. 

Adam: What is the most difficult kids TV show that you have to sit through?

Casey: Oh, that's a good one. Oh, there's some weird ones. Oh, there's one that basically has 100 dinosaurs. 

Adam: Okay, 

Casey: It gets named, the dinosaur comes out of the gate, and it gets named, and it's alphabetical, and it's literally starting with an A, and you just watch these dinosaurs come in and out.

Adam: And that's the show.

Casey: That’s the show.

Adam: Which Disney or Pixar movie are you secretly a fan of?

Casey: Oh Incredibles.

Adam: Oh, good one. How good are you at assembling toys and children's furniture?

Casey: I'm fantastic. I'm a builder.

Adam: What is your worst experience assembling a piece of children's furniture or a toy?

Casey: When you have that one missing part that your daughter ran away with. And the power wheel won't work because it literally has that bolt that, you know, it just doesn't, the whole thing doesn't work. It's like the fourth wheel is gone and you can't find it and she threw it away in the packaging and it doesn't work.

Adam: I could tell that this has been a real thing for you. What is the most absurd thing that you've ever done to make one of your children stop crying?

Casey: Oh man. Absurd thing. 

Adam: Yes, the more absurd, the better.

Casey: I'd have to make something up. Most of it is just like take away something or I become The Gruffalo. And, you know,

Adam: Ohh The Gruffalo!

Casey: I'm like, The Gruffalo’s gonna eat you right now. So, yeah, definitely when it's like, I'm gonna eat you, or you know, if these, if I see any naked skin and your clothes aren't on, I'm gonna tickle that skin.

You know, it's a, I hate to say it, it's very, like, carrot stick. But

Adam: Yep.

Casey: that's a good one. I can't even be that absurd. 

Adam: That's okay. I like The Gruffalo strategy though. Also a great book and film. What is your favorite terrible movie to watch?

Casey: Hot Shots Part Deux with Charlie Sheen. 

Adam: And finally, in honor of Laura, how many times have you said, go ask your mother this week? 

Casey: 12

Adam: Awesome. I was actually thinking you'd say a much higher

Casey: By the way yeah.

Adam: Awesome. Okay. Well, Casey, thank you very much for joining me today on Startup Dad. It was a pleasure having you. This was a lot of fun.

Casey: Thanks for having me. This was great. 

Adam-IntroOutro: Thank you for listening to today's conversation with Casey Woo. If you enjoyed the show, please subscribe, share and leave me a review. It will help other people find this podcast.

Startup Dad is a Fishman AF production with editing support from Tommy Heron. You can stay up to date on all my thoughts on growth, product, and parenting by subscribing to the Fishman AF newsletter at www.fishmanafnewsletter.com. Thanks for listening.