Battlefields, Boardrooms and Fatherhood - a Special Veterans Day Edition | Jake Wood (father of 2, Marine Veteran and CEO of Groundswell)

Jake: He said, Jake, you know, people try to overcomplicate it. You know, the, the thing about being a parent is your kids at every moment of their life should just know that they're loved. It's like, if you do that, everything else falls into place.

Like, alright, you know, there's a lot of methodologies out there, a lot of frameworks.

Like, if your kids feel loved, they're gonna grow up well.

Adam: 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. As we approach Veteran’s Day, it's an honor to sit down with Jake Wood, a decorated Marine veteran through multiple tours of duty, an entrepreneur, and a dedicated father of two.

Jake is currently the founder and CEO of Groundswell. A venture backed software company aiming to democratize philanthropy by building a new category at the intersection of fintech, benefits tech, and charity. Prior to launching Groundswell, Jake served as the founder and CEO of Team Rubicon, a disaster response organization that is considered one of America's leading nonprofits.

Jake was the subject of the book Charlie Mike, and also wrote a memoir called Once a Warrior. About his experience at war and returning home to build and scale Team Rubicon. From the battlefields of Iraq and Afghanistan, to the boardrooms of startups, Jake's journey is a testament to resilience, leadership, and the profound impact of fatherhood.

In this episode, we delve deep into Jake's experiences in combat, his transition to civilian life, and how his roles as a veteran and a father intersect in profound ways. We discuss how to be truly present, how to find a partner that understands and supports you and where to find the hours in the day.

Jake has dedicated most of his adult life to supporting veterans and helping others in need. And I'm excited to tell that story today.

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Adam: I would like to welcome Jake Wood to the Startup Dad podcast today. Jake, thank you for joining me. I hope you're having a great day.

Jake: Yeah, Adam, thanks for having me. Really excited to join you today.

Adam: Of course. Well, let's jump right in. You have a fascinating background, which includes at least two tours of duty that I could see both in Iraq and Afghanistan. And the founding of multiple companies. So tell us all a little bit more about your background.

Jake: You know, the last 20 years have been interesting for sure. I went to school at the University of Wisconsin where I was on a football scholarship aspiring to be a professional football player. Turns out I really wasn't any good at football. So, as you mentioned, I ended up in the Marine Corps and enlisted in the Marine Corps after I graduated.

That was 2005, so obviously we were kind of at the height of both the wars in Iraq and Afghanistan. Served in Iraq in 2007 as part of the surge. I was part of an infantry squad in Anbar Province outside of Fallujah. You know, tough tour, challenging tour, learned a lot about leadership, learned a lot about people, learned a lot about the world.

Following that tried out for a Marine Scout Sniper Platoon and was selected into the platoon, sniper school, all that stuff, went to Afghanistan the following year. in a sniper team. And, you know, I often kind of joke that's where I learned how to be an entrepreneur. You know, you think about what that mission is, and most people don't kind of connect the dots.

But, you know, really, it's a small team with a seemingly impossible mission with limited resources, limited information, ton of challenge and danger and risk. And you have to learn how to navigate that environment. And oh, by the way, failure is not really an option. So, it's actually very similar to running a startup.

You have to find a way you have to persevere, you have to adapt, you have to overcome all of those things. Anyway, I had enough of that after four years. And so I decided to get out. So that was 2009. It was, you know, a difficult economic period in the United States. It was a tough time to be leaving the military.

Having learned no real marketable skills in the military. I mean, I wasn't coming out as like a logistician or a cybersecurity expert. I was coming out as a sniper and, you know, it was not like I was gonna walk up to Goldman Sachs or, you know, Facebook and say, hey, like, you should hire me.

Adam: Or else.

Jake: yeah. Or else. Yeah, yeah, Yeah. So, you know, the plan was to go to business school, get my M B A, Take a couple of years to decompress, build out a professional network and figure out what was going to be next. I always wanted to do something entrepreneurial, but kind of felt like I needed to maybe hitch my wagon to somebody else's horse.

But what ended up happening was about two months after I got out of the Marine Corps the Haiti earthquake happened. And you know, I was waiting for my grad school applications to come back. It's January, 2010, and I'm just kind of inspired in that moment to go down and help in Haiti. You know, feeling like I had some good skills and experiences to, bring to bear.

And so I called a couple of organizations, they all said no to my offers to go and volunteer and help. And so I just, you know, worked with a couple of people to organize a team and we went down there, got there three or four days after the earthquake. We started running medical triage clinics in the city and we just kind of, you know, this idea began to coalesce in our brains that you know, we might be able to help build a better mousetrap when it comes to disaster response and based on this thesis that if we recruit, train and deploy military veterans for that work, that we could do it more efficiently than some of the traditional aid organizations out there. So, you know, long story short, we came back, we incorporated that the organization was called Team Rubicon incorporated as a, you know, a nonprofit company and we got to work.

You know, and if you fast forward to today, almost 14 years later. You know, the organization's got more than 150,000 volunteers. It's responded to over 1,200 disasters and humanitarian crises, raised 400 million dollars in philanthropy and is probably one of the more celebrated disaster organizations in the United States.

So I was really proud of that work. But as you can imagine, responding to the world's emergencies 24 hours a day, seven days a week was tiring. And so a couple of years ago, right as my second daughter was born, made the decision that it was time to move on to the next thing. We had, you know, a great succession plan in place, so we executed that.

And I, you know, I kind of wandered off to find the next thing. I ended up starting a venture backed software company called Groundswell. It's also focused in the social impact space, so we're aiming to democratize philanthropy. With a platform that provides a modern, what's called a donor advised fund, which, you know, we don't need to get into the details of that, but, you know, we've built the world's most modern donor advised fund and we sell it to companies as an employee benefit.

And we're excited about the prospects there. We raised a good amount of venture capital money from Google ventures and a few others and you know, two years later we're hooking and jabbing.

Adam: Yeah. How many people work for Groundswell now? That's actually how I got connected to you. A person who introduced us, Nancy Pasco, I think, used to work with you in the past. But yeah, how many folks are at Groundswell now?

Jake: Yeah, we've got about 20 people today. You know, we're, you know, obviously looking to grow over the next couple of years. All of that is, of course, dictated by what happens in VC markets and the economy. But you know, we love what we're doing. It's a very mission oriented, mission driven company, and we've got great people.

Adam: Yeah that's really fantastic. I imagine the world of philanthropy also has its ebbs and flows depending on the economy and that sort of thing. So that must've been interesting kind of ride over the last couple of years too.

Jake: Yeah, you know, it has been. Historically, philanthropy is relatively recession proof, but it turns out over the last 18 months it wasn't necessarily inflation proof. And so... Last year, the data shows it was one of the first years in probably the last 20 that we saw a pullback in individual giving when adjusted for inflation.

So, you know, certainly, you know, unfortunate development. What's more unfortunate is that you had a lot of households that saw, you know, their household income eroded by that inflation. But yeah, it's created a challenging environment.

Adam: You mentioned at the onset you went to Wisconsin to play football. I know the size of Wisconsin football players. So my guess is you were not a lineman.

Jake: I was a lineman actually.

Adam: You were a lineman. Maybe that's why it didn't go so well.

Jake: Yeah. Well, yeah, it's funny. I, yeah, nobody would guess that I'm a lineman. I don't carry the weight I used to, but I, yeah, I played football at 290 pounds and run around 230, 240 today.

Adam: Wow. Wow. That's amazing.

Jake: But you're right, they wanted me at 315. It's why I wasn't uh, didn't go pro.

Adam: uh, svelte 315.

Jake: Yeah, exactly.

Adam: So the funny thing about football and then the military as you mentioned, the military as a training ground for leadership and learning how to do a lot with a little actually two of my favorite leadership books are about football and the other one is military strategy book.

So, The Score Takes Care Of Itself. And then Team Of Teams by Stanley McChrystal, who was probably. In charge when you were in the, war they're fantastic books and has taught me a lot and I've not been in the military or played football. I'm significantly smaller than you.

 But yeah, I think athletics and clearly military service prepares you for a lot of complexity. So I think that's amazing. I'm curious about, you know, how you got into football and things like that, especially more about your life growing up.

So, where are you from originally and what was your family like as you were growing up?

Jake: I'm very fortunate that I, I grew up with an amazing family. I've been now around the world a, a few times. I've been in a lot of different, organizations where I met and had the privilege of either playing with or serving with people from a bunch of different backgrounds, a bunch of different places.

And I, think I probably took for granted just how amazing my upbringing was before encountering some of these, you know, teammates and platoon mates across the Marine Corps and Wisconsin. You know, I grew up loving parents. Both my parents were present. My dad had a good job. He was always employed.

We always had a roof over our head, food on the table, all of that stuff. His job did have us moving around a lot. So I was born in Nebraska. We moved to Texas. We lived in Europe for a few years, Illinois. We ended up settling in Iowa for junior high and high school for me. With two of my sisters getting pulled along the way throughout that time.

And. You know, it was like I said, it was a normal upbringing. I rode my bikes from sunup to sundown running around the neighborhood with kids and playing team sports. Yeah, I think I wanted to be a baseball player when I was young turns out that really was terrible at baseball. But you know play basketball and I was a big guy, right?

So I was one of the bigger kids in the class. It was natural for me to gravitate towards football. My dad had played football in high school in some college so quickly I learned I wasn't any good at any of the other sports and you know, just poured everything into football. And that really worked out well for me.

I was fortunate enough to get a full ride scholarship to Wisconsin and got to continue to play. I was all, you know, I was a good student. You know, I got good grades. I was involved with student government and stuff like that. But Again, I just would emphasize just really lucky that I had, you know, two loving parents that provided for me every single day of my life.

Adam: Yea. You know, a lot of folks will go to the military ahead of going to college and then they come back, they use the GI bill to, to pay for education. You were fortunate to get a scholarship to go to college. What was the decision like to go and join the military after graduating from college?

Jake: There was a lot that went into it. Obviously like as I mentioned, I joined in 2005, so that means that my entire time in college we were at war. 9/11 happened my second week on campus. So it had been in the back of my mind throughout a lot of those four years in college. I was voraciously consuming news of what was happening overseas.

I saw myself in the young men and women I saw going overseas to serve. And, you know, so I, you know, I end up, I'm graduating, my football career didn't pan out. I've got this business degree. I'm not really interested at that point in my life in going and doing something in business, whatever that would mean.

And so I you know, kind of decided to scratch that itch that I'd been feeling for four years. I started talking to recruiters and I had the opportunity to go in as an officer, but I really felt inclined to join the infantry. And so I just chose to enlist where I could pick my job and I, you know, that's where I chose.

Adam: What was your parents reaction, if you remember, to you telling them you were going to enlist in the midst of war, basically to go overseas.

Jake: Yeah, I think I probably underappreciate the absolute terror that I caused my mother. And my father, I mean, obviously both, but, you know, my father's terror was mixed with some level of pride. And I think for my mother, certainly pride as well, but like, you know, I, now being a father, cannot fathom my child going to war.

I cannot fathom it. I would not wish it on anyone, and I did it to my mom twice, and that's part of the reason I ended up getting out. I remember when I got home from my second tour, my dad and my mom met me at the airfield, you know, our whole battalion was coming back, we'd just lost, you know, we'd lost 20 men over seven months.

We had another 200 wounded. I was fortunate that I wasn't in either of those camps. But, you know, you're talking about, you know, 20 dead, 200 wounded out of 800 infantrymen. Your odds weren't great. And my dad hugged me and he whispered into my ear, Don't you ever do that to your mother again. So,

Adam: Yeah.

Jake: I took it to heart.

Adam: Yeah. Yeah. Sounds like you made the right call. You've been able to do a lot of great work still working with veterans. So I wanted to ask you've been the subject of a book. I was doing my research. There's a book called Charlie Mike, and then also you wrote a memoir called Once A Warrior, which is about your experience at war, return home and building Team Rubicon for, you know, 14 years. I'm curious, you've dedicated most of your, actually all of your adult life to supporting veterans and helping others in need, what was the inspiration to support veterans and this pull to want to help other folks in need?

Jake: Well, you know, I, there was a lot. I felt... I was lucky that I had an amazing support system when I came home. You know, I keep talking about my parents, my family, not just my parents, but my sisters. And they helped with that transition back. They were there for me. And if I had needed a safety net, I never really needed, I wasn't slipping through the cracks at any point in time, but if I had started to slip through the cracks in any way, like they would have been there to, to help and pick up the pieces.

Whether that would have been footing bills or... You know, bailing me out of trouble, whatever, however that might have manifested. And I had a lot of friends who weren't so lucky. You know, I had a lot of friends who came back to broken marriages, to broken homes, to you know, a guy that had to go back to the Indian reservation that he'd grown up on.

And it, you know, it wasn't a good environment, right? And so I just, I felt fortunate and I think when you... You know, when you are fortunate you have an obligation to help those that are less fortunate. And then there were, certainly more acute things. my sniper partner ended up committing suicide a few years after we got back.

We were very close. You know, that was obviously a kind of a moment of reckoning for me. And he wasn't the only one from our battalion. At one point our battalion had the highest suicide rate of any battalion in the Pentagon. And we lost more men to suicide than we lost to the enemy. So, you know, you gotta, you see that and you gotta take action.

You gotta start trying to figure out how to help. You know, and I, you know, the way that I helped was, you know, there were a lot of people that were pitching in, right? A lot of different organizations doing incredible work. A lot of Marines from our battalion that were, I mean, just literal heroes in the lengths that they would go to bail their fellow Marines out from trouble, whether it was letting them crash on their couch for...You know, months or a year or giving them a loan to pay down a debt or, you know, whatever it might have been. It was an all hands on deck effort.

Adam: You really sound like you gave a lot of people purpose when they came back from the war and being a veteran and finding good ways to help people and give folks a reason to keep going. Which is really inspiring. So I want to turn the corner because this is a podcast about fatherhood.

And we've hinted at it a little bit, but you have two kids and you have a partner. So tell me about your family. Tell me about, how you met your partner. How old are your kids?

Jake: Yeah. I count myself as the luckiest man in the world. I met my wife just only a couple of weeks after getting back from Afghanistan. She had just gotten out of a long term relationship. I had, you know, of course, just come back from combat deployment.

I don't think any of us were looking for, you know, our future spouse but we met, we connected you know, that first evening really just closely, like our interests, our values were very evident. We started dating and it was interesting because you know, you get to this decision point, at least I did, where I had to decide whether or not I was going to stay in the Marine Corps or get out.

And she was very clear. She's like, you know, I love you, but I am not sticking around for, you going back to war. I'm just like I'm not gonna sign up for that and I don't blame her I mean again, like I think at the time I you know, I was debating whether I wanted to go back. There's almost an addiction that life you know, and so I was lucky that I kind of took a gamble on our relationship and said, okay, I'll get out. And then the next one was I got into Northwestern in Chicago, and you know, we're living in Los Angeles at the time.

She was from Los Angeles, and I get into Northwestern with a full ride for their MBA program. And, you know, it's a top five school, and I go back to her, and I say, look at this. This is amazing. She said, That's great. I'm not going to Chicago. So again, I took another gamble on, where our relationship was heading and, you know, long story short, we ended up getting married and she's been an amazing partner and we have two daughters Valija, who's going to be five here in September and Laila, who will turn three in November.

Adam: Awesome. I love those names. So did you end up going to Northwestern or did you stay in LA?

Jake: You know, as soon as we had that conversation, I realized I needed to apply to UCLA and USC and got in both places there. I ended up going to UCLA for one semester before I dropped out to focus on my first company.

Adam: And probably learned more building Team Rubicon than any MBA would have ever taught you. So,

Jake: Yea no doubt about it.

Adam: That is an amazing amazing story. I desperately want to meet your wife now.

Jake: She's a force of nature. Trust me.

Adam: Tell me about what she does. So you've had a very in depth career since coming from the military. Started and led a company for a very long time, 14 years. Now you're leading another company. I know you and your wife have a foundation together.

But what does she do?

Jake: She's incredible. She's probably way more accomplished than me. So she had a degree in atmospheric physics and then went into broadcast journalism with that. So she was a weather forecaster and not the kind that you know, gets a journalism degree and then just sits there and reads you the rain reports.

Like she was a real, real weather scientist. When I met her, she was working locally in Los Angeles for the top news channel in L.A. Shortly after we got married, she did a contract with CNN. She was later Good Morning America, the Today Show. I mean, you know, she was the creme de la creme 

Adam: I should have interviewed her!

Jake: You should have, yeah, no she's unbelievable.

But it's a tough industry and think she was in it for, I mean, almost 20 years, I think. And, you know, at a certain point, she decided that you know, both of our careers were incompatible with having a family and she made the, you know, really hard professional choice to step back from her career for us to start ours.

So she left the media you know, just over five years ago so that we could start our family with Valija.

Adam: Yeah that's amazing. Tell me about that decision to start a family. What were those conversations like? Obviously the two of you are working incredibly hard and something had to give.

Jake: Yeah, I mean, it was, tough. We got married in 2013 within days of returning from our wedding, she moved to New York to start the job at CNN. So, you know, our first two and a half, three, four years of marriage, she was living in New York. I was living in LA. I was building Team Rubicon, which was, you know, three years old at the time.

She was working the morning shows first at CNN. So she was going to bed at 6 p. m. Eastern Time every day, waking up at, you know, close to midnight, to get ready for those shows. I mean, we would go days, sometimes a full week without even speaking to each other. You know, we'd send a quick text message, hey, are you alive?

And you know, we'd get proof of life one way or the other. But it then also allowed me to focus on my career, you know, or building Team Rubicon. I was, you know, working until 10 o'clock at the office every day. I was on the road probably, you know, 15 days a month trying to raise funds for the organization's mission, or going on the missions themselves.

And so, I think that, you know, that arrangement actually gave us each that the time and space we needed to focus on our careers, which were really important at that time. But we always knew that we wanted to have a family. It was just a matter of when the timing was going to be right. And you know, around 2017 I think we both felt you know, somewhat fulfilled professionally.

And, you know, the clock's always ticking. And so, we felt like we'd waited as long as we wanted to. And, you know, made the decision to start having kids. You know, that's never an easy process. But we’re blessed with two beautiful girls.

Adam: Yeah. In our prep you talked about finding one of the most important things in life is finding a partner that understands and supports. How does your partner, your wife, understand and support you?

Jake: Well, I mean, she's always been supportive, you know, throughout my career for the last, you know, 15 years and that's, given me the liberty to do what I need to meet, you know, the expectations and requirements of my job, you know, as a CEO I employ people, their livelihoods depend on the success of the company, the success of the company depends on the decisions and the actions that I'm taking.

And so, You know, I think she knows that responsibility weighs heavily and she, again, gives me, you know, the liberty to, hey, if I have to fly across the country and be gone for two days, I'm going to do that. Now, what does she expect in return? You know, she expects me to be present when I'm present.

She expects me to prioritize the kids when I'm able to. And of course my, you know, my kids, my family are always the top priority, but of course that's gotta be balanced, right? There's gotta be that give and take, like, part of that priority, taking care of my family, is taking care of the business.

Because if the business fails, I can't take care of the family. So it's a, you know, it's a delicate balance. I don't always get it right. She's very transparent with me when I don't get it right. And that's, yeah, that's fine. That's not a complaint. That's you know, that's, I think you know, a demonstration that the partnership is strong.

It's healthy.

Adam: Yeah. So you use the phrase, be present when you're present, which I like a lot. And I've heard people say some version of that in a couple of other interviews that I've done. What does that mean to you? What does it take for you to be present when you're with the family?

Jake: Oh, it's hard. It's hard. I say it and I hope nobody interprets it as like, it's a mantra that I live and breathe. And I, you know, I meet every day. It's the type of thing I have to repeat to myself in the middle of a moment when I'm not giving my kids my undivided attention. But, you know, it's got to be the goal.

You know, when you're a CEO at a startup, it's really hard at the end of the day to turn your mind off, right? To context switch from spreadsheets and budgets and strategy or personnel issues and go home and, you know, do a tea party or talk to your wife about how her day was but that's what you owe them, right?

And so, you know, that's the constantly what I'm repeating to myself when I find myself pulling out my phone to check that, that alert that I just got on slack or email when my eyes are glazing over cause I'm thinking about that sales call that I had that I fumbled in. So you know, the thing that I always try to remind myself is that your kids know when you're not paying attention, they know when you're mailing it in with them in play.

And so I try really hard to be immersive with my kids. You know, we've got a bunch of games we play and you know, sometimes I'm not in the mood for it, but I gotta, I gotta get in the mood for it.

Adam: Yeah. What are your daughters into right now? What's sort of a favorite playtime activity for you with them?

Jake: You know, our oldest daughter can't stick with the same thing for more than like two minutes, so, you know,

Adam: She's enthusiastic.

Jake: I'll get home, you know, I'll have two hours with them maybe before they go to sleep, and I'll tell you what, we'll go through like 15 different activities. So, sometimes it's hard to even say, but, they're into the princess stuff.

They're you know, hide and seek, and you know, we're trying to get her more interested in, learning how to read and some of the things that she is expressing zero interest in and it's fine. You know, it's fine I was probably uhh late to that party too myself, but you know, it's a lot of interactive…I'm a big guy, she's a maniac. So she wants me to pick her up and throw her. Oh, you know, we have these games or it's just physical stuff and so a lot.

Adam: That's awesome. I feel like, you know, a lot of people think about that's an important thing to do with their sons, but equally important to do that with your daughter. So that's amazing that you can be rough and tumble with them and then also go you know, have a tea party.

Jake: My oldest daughter is an interesting dichotomy because she's super into princesses and doing her hair and makeup and all this stuff, which neither my wife or I are into. But then at the same time, she's a total maniac.

Yeah. Like wants to jump off everything, crawl, climb, you know,

Adam: I wonder where she gets that from.

Jake: Yeah. Yeah. Your guess is as good mine.

Adam: So rewinding back to the beginning when you're, oldest daughter was born. What's the earliest memory that you have of becoming a father?

Jake: My earliest memory of becoming a father is probably the you know, the moments or hours right before it physically happened. My wife was in labor for 50 hours, five zero,

Adam: That's more than two days for those doing the math at home.

Jake: Yeah, between when her water broke and when she delivered. And and she was pushing for five or six of it. I mean, it was, and I remember we're at hour 49 and I thought to myself, oh my God, like, is this how, like, Is this how, you know, deaths during delivery happen?

Like, is this not going to work? Like, you know, if you've actually watched a baby delivered, like, you sit there and you wonder how the human species survived.

Adam: That's right. Yeah.

Jake: And so it was, I would say it was pure terror. In those final moments that like something wasn't going to work out and then the moment that my child came out, it was like this moment of pure, like a joy that you've never felt and every, you know, it's so cliche, like, oh, there's life before your kid is born and there's life after it.

It's true. Cliches exist for a reason, you know, first time I held that girl, put her on my chest. It was just like, my God, I will never be the same person ever again.

Adam: Wow. What an amazing story. And gosh, what a warrior your wife is. 50 hours of labor is no joke.

Jake: Yeah. Yeah.

Adam: You mentioned when you see childbirth happening that it's a miracle that the human species has survived, just how challenging it can be. And there's tons of stories of people who have challenges with it.

And of course that doesn't mean it's not worth doing, of course, but I'm curious because I saw that you started a foundation with your wife. And one of the places that you support is the Children's Hospital of Los Angeles. And you mentioned in your bio that a big reason for that is because they saved your daughter's life, youngest daughter when she was born.

So tell me about what happened there and why that hospital is so important to you.

Jake: Yeah. So with our second daughter, my wife got pregnant very early in COVID. You know, we'd been trying and the one month that we were supposed to stop trying you know, we were kind of working back to my book was coming out in November, 2020 and I needed to be available to do the book tour.

And so we said, okay let's work backwards. We can't get pregnant this month. Well, that's the month we got pregnant.

Adam: Of course.

Jake: Um, yeah. And so that's unfortunate. And so, you know, a couple of months in, we almost lose the pregnancy. My wife began hemorrhaging and it was, you know, really terrifying experience.

She ends up going on bed rest for seven or eight weeks. So I'm, I'm the busiest I've ever been running a disaster response organization during COVID. We've got a two and a half year old at home and my wife's on bed rest. So it was just, it was crazy.  

Adam: Wow.

Jake:After, you know, she had a checkup then at the, near the conclusion of this bed rest to ensure that the pregnancy was still viable.

It was great. But in that same meeting as the doctor was doing this ultrasound, special ultrasound because my wife was older, he discovered that our baby had a heart issue. She had something called TGA, Transposition of the Great Arteries. It's extremely rare. It basically means that the four main arteries that come into the heart were coming into the wrong chambers.

And so what that meant was it's unsurvivable at birth because your heart does not oxygenate the blood. It pumps bad blood to the body. And it requires this massive heart surgery. And there's only, you know a dozen hospitals in the country that can do it. Fortunately, two of them were within 20 miles of our house here in Los Angeles, so we felt very lucky.

We just started prepping for that. We chose CHLA to do the surgery with a surgeon that was kind of world renowned there. Again, felt very lucky. And so my daughter was born at a community hospital a few blocks away from the children's hospital and we had to rush her in an ambulance over to CHLA and, you know, they, was this extraordinary effort by dozens of doctors and nurses and surgeons and it was you know, they saved her life and she's today almost three years old.

She's thriving. She's smart, she's sassy, she's, you know, she's all these amazing things and it's because we're just extraordinarily blessed.

Adam: Wow. Wow. What a miracle story. That is really amazing. I wanted to ask you what are some of the more, surprising things that you've discovered since becoming a dad?

Jake: How quickly they can understand you, and so you better watch what you say. Yeah, I think that a child's intelligence is really amazing. Like the cues that they can pick up on, not just language, but, you know, more subtle cues. It's really incredible to see their minds at work.

And it’s also extraordinary to see yourself and your spouse and your kids. And to see that manifesting in just really different ways at different times and, you know, to see this balance and this blend in the human. And then there's like this third entity and you're like, I don't know what the hell that is, who that person is, but like, you know, I wish we could cut that part out.

But, you know, they all got that third trait, characteristic, whatever it is. Probably some long lost crazy uncle on either side of the family. That’s contributing to the genes.

Adam: Ha. We all have one.

Jake: Yeah. So it's, those are the things that I think amazed me. And one of the other things was, and I don't know, I think this is probably pretty common, but you know, my first daughter was the apple of my eye, the joy of my life.

I love her more than anything in the entire world. And then, you know, you have this moment when your wife's pregnant with the second and you're like, I don't know. I don't know that I can love another child as much as I love the first one. It's impossible. And the moment the child's born, you're like, Oh, okay. I get it.

Adam: Yeah.

Jake: There's more capacity there. Okay.

Adam: Yeah, Matt Greenberg, who's been on my show, talked about there is no law of conservation of love when it comes to your kids. It just expands exponentially, which is a pretty amazing way to think about it. Those are some wonderful surprises of being a dad.

Thanks for sharing those. I wanted to ask you, What's your kids favorite book and what's, I guess, your favorite book to read to them right now?

Jake: Yeah, I think it's always been Tickle Monster.

Adam: Oh, I love that book.

Jake: Yeah, it's my favorite book. We get super animated with it. We've got a whole routine. It also happens to be my least favorite book because we've got a, we get super animated with it and we've got a whole routine. And, you know, they never want to hear it just once.

They want to do it two or three times in a row and it's exhausting.

Adam: Yeah.

Jake: But it's a, pretty amazing book.

Adam: Yeah. That's awesome. I love that book. We'll put it in the show notes. Also amazing that it can simultaneously be your favorite and least favorite book at the same time.

Jake: No doubt.

Adam: It doesn't exactly settle them down before bed, I imagine, so.

Jake: No, not even the slightest.

Adam: So I wanted to ask you because this is, you know, the intersection of kind of business and parenting, do you have any particular frameworks or guardrails for parenting that you've established or anything where you're like, this is an approach that I take that I think is unique or different.

Jake: Not really. You know, I was lucky to have a lot of great father mentors, you know, guys I worked with at Team Rubicon who were older than me that were great fathers, in my opinion. And, you know, one of them was my COO. He's now the CEO of Team Rubicon. His name's Art Delacruz. Four kids, amazing father, amazing husband.

He said, Jake, you know, people try to overcomplicate it. You know, the, the thing about being a parent is your kids at every moment of their life should just know that they're loved. It's like, if you do that, everything else falls into place.

Like, alright, you know, there's a lot of methodologies out there, a lot of frameworks.

Like, if your kids feel loved, they're gonna grow up well.

Adam: That may be the most straightforward framework of them all so that’s a good one for people to remember.

Jake: Yeah, let's not overthink it, right?

Adam: Keep it simple. That's great so you mentioned, you know, the importance of partnership obviously with your spouse and I know that it's super important when you have kids, but it is also difficult to agree all the time with your spouse.

So what's something that you and your wife don't agree on when it comes to parenting?

Jake: I don't know that there's much. We're pretty well aligned, and when we're not, I think we're pretty quick to compromise. I think that the way I'd answer that question is, you know, we're frequently not on the same wavelength. So like, there'll be moments when she’s like, seeking discipline and I'm like, I'll let kids be kids.

And then there's, you know, moments where that flips. And those are the only moments where we argue. It's like, wow, you really need to cool your jets. It's like, you just did that yesterday. Give me a break. You know? But I think like generally we're pretty aligned on what we want to do.

It's just there are certain moments where there's misalignment in the moment.

Adam: Yeah, that's amazing. You can't get lost in the moments though for the long term. Right. So that's good. One of the things you told me in, in our prep is that you're a pretty early riser and one of your mantras is to kind of find the hours for yourself. So tell me, what does that mean for you when what's your schedule like as a parent and a CEO?

Jake: The reality is for anybody that's a CEO out there, there are some things that only you can do and particularly in a startup, you know, with scale, you can start to farm a lot of that stuff out. And I got to that point at Team Rubicon where I was like, you know, my days were pretty sparse.

Like I was really only focused on high level stuff, contemplating big decisions, maybe dealing with some personnel issues here or there. But, when you're in the startup space, like you don't have the ability, the resources, it would be irresponsible even to, you know, try to delegate all of the things that a CEO needs to be doing.

And so the reality is there's just a lot of stuff and not a lot of hours. So you've got to find the hours and you know, I want to be present for my kids. So that means I, I find three hours before they wake up typically between four and seven. You know, as soon as they wake up, I take the opportunity to make them their breakfast and you know, get some time, just, you know, some early morning cuddles or whatever you want to do.

And then I go to work. I drop my older daughter off at school. I make it a point that I do that routine so that I can get as much time as I can with her. I try to get home for dinner. I'm home for dinner almost every night that I'm on the road. And that's because I put in three hours before.

Adam: Yeah.

Jake: The work day. And you know, I spend those two hours at night from six to eight before they go to bed with them, you know, again, trying to be as present as I can. But I think there's a lot of people who, those three hours they might tack onto the end of the day. They don't get home until eight o'clock.

They're barely able to kiss their kids goodnight before they go to bed. And, you know, I'm not gonna sit here and tell anybody they're a bad parent. I just, that's not how I, you know, I wanna spend more time with my kids than that. And so, try to find those hours. It's a pain in the butt. You know, I, I don't love getting up early.

It's become like a habit. So I naturally do it now. I don't get to the gym as frequently as I want. That sucks. I only go on the weekends. Again, I'm trying to be present. So some things have to take a back seat. But it's because, like, again, I've got to prioritize my life and something like hitting the gym, yeah, your health's important, but like, so is making payroll.

Adam: Yeah. I was going to ask you what you do in that four to seven time frame and is it exercise, but it sounds like it's CEO stuff.

It's some of this stuff. So you don't have to be at work as late.

Jake: No my feet hit the ground when I get out of bed, I'm at my desk within seven minutes every morning.

Adam: Yeah, I find one of the things about parenting is if you're not a morning person, it certainly has that effect on a lot of people. So, and then the other thing I find really interesting, and you mentioned that you don't work out as much and it's mostly confined to the weekends.

One of the things I found is as my kids have sort of grown up and got, I mean, they're not super old yet, but schedules change and what you're capable of and the hours and stuff are really. Kind of change over time. So everything is a snapshot and a period of time and you know that can shift which is interesting. What is something that you have had to give up to become a father?

Jake: Well, the gym. You know, and then I'd say two things. One is, one is starting to swing back, you know, for the last couple of years travel, my wife and I used to travel a ton and we'd go to exotic places, challenging places and you know, you can't drag a five year old and a three year old to, you know, sub Saharan Africa or the mountains of Uganda.

Yeah. Like we used to do. So I think we're eager to get back on the road now. We've been able to actually sneak away just as the two of us this year for kind of the first time and leave the kids with somebody else, which is great, you know, allows us to reconnect. But, you know, you still want to be like a direct flight, you know, within reach of a direct flight should you need to get home for anything urgent.

So it's still some limitation, but you know, we're really eager to take our kids to some of those exotic places as they get older and show them the world and hopefully we'll be in a position financially to do that. The second thing is football. I love football. I could sit in front of a TV and watch football all day Saturday and Sunday in the fall.

My wife hates football, so I'm on a, I'm on a decade long influence campaign to try to raise my girls as football fans. So that my wife has no choice but to spend time with us on Saturday and Sunday. So, we'll see how that goes.

Adam: That's how you reclaim football. I love that. I love that. The other strategy, which I've employed to great success is you marry someone that you went to college with, who is also a fan of your college football team.

Jake: Yeah, you know, I love my wife, but man, I really screwed that one up. Yeah, I'm with ya.

Adam: That's great. What is a mistake that you've made as a father?

Jake: That's a good question. You know, I try not to set myself up for failure. In what I mean by that, just kind of revisiting earlier part of the conversation, I try not to overcomplicate it. So I really just try to love my kids, you know, help them feel loved every moment of every day. And you know, I think I've done a good job of that.

You know, I've dropped balls here and there and you know, like screwed up this, that, or the other thing, but. And I'm not saying I set the bar low. I'm just, you know, I think all of the mistakes I've made, none of them are, I guess, mistakes of the heart, right? Like I, you know, I've probably kept them up too late or, you know, I might've been away for some event that it would have been nice to be at.

But again, all in this spirit of, doing the best that I can and so I feel pretty good about that

Adam: That's good. And I think they probably, as you mentioned, they can sense that, right? So kids are very receptive to the fact that you care and that they feel loved. So you've started now two companies, Team Rubicon and Groundswell.

And, you know, one of the things we talk a lot about is this idea of the hustle culture of a startup. And, you know, your last company is kind of the epitome of that. When stuff hits the fan and there's a disaster, it's go time. How have you found that this idea of hustle culture or sort of the pace of a startup fits in with, family life?

Jake: You know, first of all, like the whole meme culture thing. I is, makes me chuckle, but you know, I, this hustle culture grind set thing. I'm like, all right, you just You know, get over yourselves.

Adam: Yeah.

Jake: But at the same time, I'm also just sometimes perplexed by how much this idea of hard work gets lampooned these days some folks.

You know, this idea that there's something inherently flawed about, you know, working your ass off. And, you know, I'm super thankful that my dad...worked extraordinarily hard. And listen, there were moments where I wish he would have been more present. He worked really long hours, but you know, part of his job was helping failing factories not close.

And so when you look at, you know, What happened to American manufacturing over the last 30 years, like his job was trying to prevent that. So, you know, it was high stakes. There were families that were counting on him. And so I also take a lot of pride in the work that he was putting in to save, you know, those jobs and in some cases to save those towns from economic decline.

And so I can look back on him and I can appreciate the hard work that he put in and I guess forgive him for some of the nights where he didn't come home until midnight. Now I don't work nearly as many hours as my dad does, but I probably travel more than he did for work. And it's also in a good cause, right?

I've been really lucky for the last decade and a half. I've created companies that are, I think, at their core mission driven and making society better. So, It's a long winded way of getting to the question you asked, which is what do I think about hustle culture? I think that it can coexist with being a father.

I think you have to be thoughtful about it. You know, we've talked about kind of the schedule that I create for myself. You've got to be willing to take the red eye so that you're not spending you know, extensive time away. And you've got to be present when you're present, like we're talking about.

So, I know my daughter will grow up feeling loved. I know my daughter will grow up knowing that I've done everything in my power to help her achieve her dreams. And I'm pretty okay with that.

Adam: Yeah, that's a pretty great way of thinking about it. Thank you for sharing that. Okay, two more questions for you. One of which you kind of already answered at the beginning. But if your kid, one of your kids, came up to you and said, you know, Dad, I'm gonna go join the military. What would your response be? What would you say?

Jake: Join the Marines or join the military? Because if she came to me and said join the Marines, I'd say join the Air Force. It's going to be a much better quality of life. And I mean that. I am proud of having been a Marine. I would do it all over again. The Marine Corps is a tough place for a woman.

Adam: Yeah.

Jake: I think the Marine Corps knows that and is trying to change that, but they've got a long way to go.

And that's a part of that Marine Corps culture that is bad. There's a lot of great things about the Marine Corps. But their treatment of women historically and the inequities for women in that branch are deeply entrenched. So I would wave her off from the Marine Corps. I think military service is a noble thing to do.

I think service to others and something bigger than yourself is an important lesson that people can learn in life. It's a hard life and I would want her to make that decision with eyes wide open and I'd be completely honest with her about my experience. My wife would freak out. So we would see how that would ultimately play out.

I'm not quite sure.

Adam: You'd be hugging your daughter when she gets off an airplane and saying, don't ever do that to your mother again.

Jake: Yeah, exactly.

Adam: Okay. Last thing I just, I'm curious, how can people follow along with your journey or be helpful to you and the work that you're doing.

Jake: Yeah I'm a pretty easy guy to find. Pretty active across social media. I think. I've tried to be available to, you know, my stakeholders you know, in that regard. So whether that's, you know, any of the socials Instagram, Twitter linked in, you know, happy to have people follow along. If you follow me on Instagram, it's mostly going to be pictures of my daughter.

So don't feel like you're gonna get professional advice there. But you know, beyond that, you know, we're really excited about what we're building it Groundswell. You mentioned the foundation, my wife and I created, you know, that's all on the Groundswell platform. So part of the technology we've built is the ability for anybody to create their own personal foundation in 60 seconds and really, you know, unlock their inner philanthropist.

We want the world to be more generous. And part of that is, allowing people to do that. So folks can go to my.foundation. And create their own and again, trying to unlock that generosity and show the world what matters to you and help make a difference.

Adam: Awesome. We'll make sure to link to all that stuff in the show notes too. So thank you for sharing that. And hopefully, you know, maybe you get some LinkedIn followers and not as many Instagram followers out of this.

Jake: Let's, yeah, let's do it.

Adam: All right, if you're ready for our, rapid fire, our lightning round here's how it works.

I'm going to rattle off a question and I would like you to respond as quickly as possible with the first thing that comes to mind. So, if you are ready, let's dive in.

Jake: Let's do it.

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

Jake: Onesies with zippers.

Adam: What is the most useless parenting product you've ever purchased?

Jake: Onesies with buttons.

Adam: Which one of your kids is your favorite?

Jake: The one that's currently napping.

Adam: What is the most frustrating thing that has ever happened to you as a dad?

Jake: Double sided blowout.

Adam: Oof, same. How many parenting books do you have in your house?

Jake: Probably over 50.

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

Jake: Not a single page.

Adam: What are the favorite ages for your kids so far?

Jake: Whatever age they are today.

Adam: What about your least favorite age?

Jake: Whatever age they are today.

Adam: Screen time. Is it good, bad, or are you indifferent?

Jake: My kids could probably use less of it, but I think it's also one of those things that, you know, if managed well it's perfectly fine and it's, frankly, it's the future.

Adam: Alright, how many dad jokes do you tell on average each day?

Jake: I tell them at work all the time. 

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

Jake: My kids are 99th percentile height and weight, so you're not getting by without snacks before dinner time.

Adam: Have you ever pretended to be asleep to avoid a middle of the night wake up from one of your daughters?

Jake: Embarrassed to say yes.

Adam: I don't think there's anything embarrassing about that. Most people have answered yes. What is the most absurd thing that your kid has ever asked you to buy for them?

Jake: A rocket ship.

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

Jake: Eh, probably four or five days.

Adam: Whoo, that's a good one. Okay, what is the most difficult kids TV show that you've had to sit through?

Jake: Oh my god. Anything Cocomelon.

Adam: Oh, okay. You know, I recently heard about Bluey, and apparently Bluey is a very good show, but I never

Jake: Good show. Quality show.

Adam: Okay. What is your favorite terrible dad movie?

Jake: About a bad dad?

Adam: Oh no, just a terrible movie that dads tend to like.

Jake: Diehard.

Adam: Okay. I do love the clarifying question though.

Have you ever used your kids as an excuse to get out of a social event?

Jake: Every weekend. Puss in Boots.

Adam: Ooh, good one. How good are you at assembling toys and kids furniture?

Jake: Pro. Total pro.

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

Jake: When we were getting ready to go to the hospital to have our second daughter with the heart surgery and all that stuff we bought a playset for the backyard, like with a swing and a fort and all that slide, and I had to do the entire thing solo, which was like a bridge too far.

Adam: Brutal. Brutal. What is the weirdest place that you've ever found a diaper?

Jake: Glovebox.

Adam: How many hours of sleep do you actually get in an evening?

Jake: Five and a half to six and a half.

Adam: What is your policy on naps for yourself? Are you pro nap, or do you not take naps?

Jake: Naps were invented by the Soviets to make Americans weak.

Adam: What is the most absurd thing you've done to make your child stop crying?

Jake: Probably break down in tears myself.

Adam: Oh boy.

Jake: Make it stop.

Adam: Have you ever eaten something off the floor using the five second rule?

Jake: Absolutely.

Adam: How many times have you said, go ask your mother this week?

Jake: Probably nightly.

Adam: And finally, what is your stance on minivans?

Jake: Practical. Don't have one though.

Adam: You do not have one, but they are practical. Okay. All right. Well, Jake, thank you so much for joining me today on the show.

It has been a real pleasure. I appreciate you sharing everything that you did with our audience. And I look forward to uh, talking to you again in the future.

Jake: Well, this was great. I appreciate you having me on.

Adam: Thank you for listening to today's special Veteran’s Day conversation with Groundswell founder and CEO, Jake Wood. If you enjoyed the show, please subscribe, share, and leave me a review. It'll help other people find this podcast. Startup Dad is a Fishman AF production with editing support from Tommy Heron.

You can also stay up to date on my thoughts on growth, product, and parenting by subscribing to the Fishman AF newsletter at www.fishmanafnewsletter.com. Thanks for listening.