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Money and Marriage Struggles as a Cofounder with Jordan Gal | Dad of 3 · Startup Dad

• Jordan Gal (00:00): My wife and I grew up very differently. The joke between us in terms of parenting is that at her table you could talk about anything except money and politics. And at my table, the only thing we talked about was money and politics. We kind of collided in our familial cultures. And what we're trying to do is give our kids the best of both and be aware of the pitfalls of either one. Adam Fishman (00:28): 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. I'm joined today by Jordan Gal. He's a five-time founder and the CEO of AI startup Rosie, an AI powered phone answering system for small businesses. He's also a husband and the dad of three daughters. We talked about being an immigrant parent, teaching your kids entrepreneurship in subtle ways, managing stress and not bringing that home, being extremely family first and how to talk to your kids about money in a healthy way. I hope you enjoy today's conversation with Jordan Gal, and if you like what you hear, please subscribe on Apple, Spotify, YouTube, or your favorite podcast player. So you never miss a weekly episode. I would like to welcome to Startup Dad, Jordan, super excited to have you here today. Thanks for joining me. Jordan Gal (01:28): Thank you very much for having me. I am looking forward to this conversation. Adam Fishman (01:31): First, I wanted to thank Aaron Francis, past Startup Dad guest for introducing the two of us. We just did a fantastic episode together. So anyway, so thank you to Aaron for introducing the two of us. He's fantastic. You sir, are an immigrant from Israel and you described your life to me as growing up in a classic immigrant entrepreneur household. What does that mean? Jordan Gal (01:59): I think a lot of people who are immigrants would identify with it, and this country attracts people with a certain type of ambition and my parents were of that stripe of this general more freedom, more opportunity type of ambition. And that often leads immigrants to be entrepreneurs because you make it all the way here and it feels very compatible with the freedom that this country provides to start your own business. So that's what my parents did. They came here, my dad worked for someone he had a connection with for a year, kind of got on his feet and then started his own business. And growing up in that household, you just get a very specific experience as a child. It's a intense experience, at least it was for us because we had our immediate family of five people and really no one else. (03:01): We had an uncle in Connecticut by funny coincidence, Dorit Lemel on the Real Housewives of Beverly Hills. That's my cousin. Okay. So by crazy coincidence, that was our only familial connection. We would go there for holidays and that sort of thing, but besides it's just the five of us. So it was a very intense experience from a family point of view, watching my dad do the business thing. And I think he also didn't really have peers. This isn't like when you're just hitting up WhatsApp and saying hi to your buddies back home. So he shared his experience with us and we absorbed all of it mostly for better and some of it not. And that will color your perspective on work, employment, being the boss, upside, risk, all that stuff is you are marinating in that sauce for a long time. Adam Fishman (03:50): Yeah, and it sounds like that marinade has led you to found four or five different companies including your current business, which is Rosie. I'm wondering about your pain tolerance because founding so many companies, there must be something maybe slightly off about you or just you have an extreme tolerance for pain. So what has that been like? Jordan Gal (04:13): I actually don't have a good tolerance for pain and I try to avoid it, but the positive side of that equation, the desire for financial freedom and time freedom, overwhelmed any sense of risk to the point where it became very, very obvious to me. The truth is I have been an entrepreneur my entire life except for one year right out of college where I fell into a bit of a trap that I looked around at my peers at the University of Michigan and I automatically just looked at what they were doing and they looked at what everyone else was doing and this is what we do. And so I went into investment banking and I hated it. And it was a very, very straightforward trade off. You give us a very, very large portion of your life and your freedom and we will give you more money than all of your peers. And I was confronted with that equation and that's not good enough for me. So it's actually not purely about money, but so focused on the freedom to do what I wanted to do and I thought I was arrogant enough to think I'll get the financial freedom and the time freedom. So that overwhelms whatever risk or pain or anything else. Adam Fishman (05:26): And of course your time is not your own when you're an investment banker, it belongs to your boss. Well, I'm glad you got out of that. And now you have a partner and you have three kids and you founded a whole bunch of different businesses. One of the things that you mentioned to me is that you are trying to learn from your own upbringing experience as to how you parent your kids. I guess tell me a little bit about your kids and tell me what that means. Jordan Gal (05:54): The way I look at it is my wife and I grew up very differently. I just explained a little bit about how I grew up. She grew up with a father that went to the military, came back, went to Harvard Business School and then worked at a few companies and then stuck with one company for a very long time, did well with that and had a successful career and that's what she saw. So what she absorbed was you put your head down and you work really hard and that pays off. The joke between us in terms of parenting is that at her table you could talk about anything except money and politics. And at my table, the only thing we talked about was money and politics. We kind of collided in our familial cultures and what we're trying to do is give our kids the best of both and be aware of the pitfalls of either one. (06:53): So in general, I would say I grew up knowing too much about money. I knew our financial position as a family. I knew the accounts receivable of the business. I knew why things were tight right now, but that would change in 90 days because of this other thing that happened and I knew why we couldn't spend because we needed to invest it. So it was like too much. It's a lot for a 14, 15-year-old to carry around, but it gave me a instinctual feel for business and money and finances and risk and debt and all that stuff. So there were some pros and cons there. And my wife's family didn't really talk about money and for them it was basically focus on excelling in academics, finding things that you're interested in, focusing on them, basically let us worry about the money, as parents. You be a student, be a good person, go to college, that sort of thing. And she came out less equipped to handle finances and understand how the world of money works. And so ideally we can bring the best of both to our kids so they have a good understanding, but we don't do the shock treatment that I got. Adam Fishman (08:04): You also describe yourself to me as extremely family first when it comes to prioritization, which is not always something that I would hear an entrepreneur talk about. They talk about their startup often as another kid in the family if they are parents themselves. And so what does it mean for you? You have three kids, what does it mean for you to be extremely family first while also running a growing business? Jordan Gal (08:33): I guess it's just a matter of prioritization and what the goals are. I do care about my career, my company, I care about professional reputation, all that stuff, but it just doesn't even hold a candle to the actual goal and priority of family and security and that sort of thing. I think that comes from two places for me, right? There's a little bit of DNA mixed in there. Sure, that's just me. But in terms of experience, I was born in Israel on a kibbutz and a kibbutz is a commune that colored my perspective. It is literally a commune. Everyone has a job and the cars are public. No one owns a car. Now it's very different, but back then people didn't even have bank accounts. You would go to the store with your little card and your number and you would just buy stuff and it would just kind of get deducted from your annual allowance. (09:31): And my dad was the kibbutz accountant and my mom took, I'll take care of kids. I mean it is full on communism, socialism that makes you look at your community very, very differently. You're really part of something very tight knit. Then when we moved over to America with just the five of us, we had that very intense experience with just the five of us. So it was really us against the world type of a feel. And I don't like Nassim Taleb, but he has a great line or maxim, whatever you want to call it, where it's like communists with family, socialists with close friends, Democrat with local politics, Republican with state politics, libertarian with federal politics. Basically the further you get away, the less control people should have because they're further away from the people that matter and care. So that's kind of how I view a lot of it. (10:25): So it's like the kibbutz thing plus the immediate family as immigrants thing and that I just view everything through that and I've had difficulty caring properly about certain aspects of business because it's all in service to this other thing that matters so much more to me. It all feels like a tool. In some ways, I hope for a second part of my career where I can explore things that I'm much more interested and passionate about because everything up until now feels pretty much like I just want to make money for the actual priority, which is my family. Adam Fishman (11:04): Yeah, it's sort of like business is a means to an end for now to support the things closest to you. So you live in Chicago now and we're going to talk a little bit about your journey. You recently moved there maybe a handful of years ago? A few years ago? Jordan Gal (11:19): Almost three years. Adam Fishman (11:19): Three years. Jordan Gal (11:20): Yeah. Adam Fishman (11:20): Okay. But you were in Portland for a long time, but what I want to hear about even more so than that is with your oldest daughter and your wife, your oldest daughter's 13, you spent about 18 months living a fairly nomadic lifestyle and this is predating COVID when that became fashionable to do. And so you went around for 18 months with a young kid and your wife. What was that experience like? Jordan Gal (11:49): Yeah, my wife and I have been together since we were 20, so we met college on a blind date, so we have been hanging out together for a very long time. So we've had a lot of adventures and that is one of our favorites. So what happened was I grew up in Long Island and my wife grew up in Connecticut, so we were like New Yorkers effectively. The city was for us, the center of our universe. After college, we lived in New York, we lived in Brooklyn, we lived in Connecticut a little bit, and I worked with my family business with my father and my brothers at times. That was a property tax reduction business, kind of an interesting thing. And I did that for a while and then decided, you know what? It's time for me to go out on my own. We were in the family business together and it started to get a little tense right as we had kids. (12:37): My older brother had a kid, I had a kid, and that will take the lid off of your ambition and reveal some things to you and to the people around you. And what the family business arrangement required us to do is put the lid back on and that felt unhealthy. So we decided, hey, we love each other more than we care about this business. Let's go our separate ways. And not surprisingly, everyone's individual position got better as soon as we did that. What it meant for me was I went fully online and when I went fully online, my wife and I looked at each other and we were like, hey, we've been talking about traveling. This is an opportunity. Let's go put our stuff in storage. And we had been talking about leaving the New York area for a while. Growing up there you can become convinced that that is the center of the universe and nothing else matters, and that is not a very healthy view of life in general. (13:29): So we wanted to try something else. We felt we moved to the suburbs a little too early. I was working during the day and she'd go out and hang with friends and everyone would be talking about their interior designer and their vacation and their paint, and then she was like, well, this is the most boring thing I've ever experienced. So we said, perfect, let's go. This was right around the time that two things happened, Airbnb and WeWork and those two things combined made it possible for us to go spend a month or two at a time in a different city in what we called interviewing cities. Instead of go there for a weekend, let's go live there for a month or six weeks and see if we could live here. So we checked out a bunch of different cities. We went to Portland, Berlin, Seattle, Denver, Miami, and maybe another one or two I'm forgetting, and then decided, okay, Portland's the right fit for us, let's go there. And we lived there for eight years. Adam Fishman (14:20): Wow. How old was your daughter when you were doing this journey? Jordan Gal (14:24): She was one, and by the time the 18 months was up, she was two and a half and we had just had our second daughter, my middle daughter, we went to Miami, that's where my wife's parents were and we had the baby close to them because that was a great opportunity. And then we went to the geographic and cultural opposite of Miami, which is Portland, Oregon. Adam Fishman (14:45): Not that many cyber trucks in Portland, Oregon, as you would find in Miami. Jordan Gal (14:50): Yeah. The way I categorize it is in Miami, walking around as a pedestrian with a stroller, you have a 25% chance of dying every day you walk out the door and in Portland we would get to a crosswalk, both sides of the street, slow down and stop. You cross, you give 'em a smile, you wave to everyone, nobody honks, and then everyone continues on and we were like, what is this place? We like this version of things. Adam Fishman (15:19): When you're traveling around and you're living in places for six weeks, couple months at a time, and you're going international and you're crisscrossing the United States and you have a young kid and then a second young kid. One of the things that terrifies me about this thought is that kids come with a lot of stuff, pack and play, high chair, crib, stuffed animals, blankets, clothes, all that sort of stuff, strollers. How do you live a nomadic lifestyle with all the stuff that comes with having young kids? Jordan Gal (15:53): It was a great experience in challenging a lot of those assumptions. We didn't need 90% of the stuff that we thought we needed, and I don't know if it's that our oldest is just really cool and mellow or if that trip and her parents on that trip helped her become mellow in that way, but it was a piece of cake. It did not matter as long as she had her people and something that felt like home, which was the pack and play and blankie and that sort of thing, and she was just off and running and loved the whole adventure of it. And in general, it was a great challenge of a lot of assumptions around life and stuff. We had such a funny experience when we got to Portland and we decided we're staying and then we sent the, what's it called, a pack rat or whatever that big container thing. Adam Fishman (16:48): Yeah, the pod storage. Jordan Gal (16:49): The pod, yeah. So we had it sent to us and when we opened it, we couldn't believe the nonsense and junk that we kept. Why would we need any of this stuff? And I think those 18 months of just living suitcase and Airbnbs was like, you don't really need much at all. Then we started collecting things again as one does. Adam Fishman (17:08): Okay, so you're the second person I know who has uprooted their entire family from Portland actually, and moved to Chicago. I have a very good friend who's also done this journey. He went Chicago, Portland, then back to Chicago several years later. You did this a few years ago. It seems to have coincided with the start and the launch of your latest company, Rosie. Why'd you do it? Why'd you move from Portland, panacea of family life to Chicago? Jordan Gal (17:37): Yes. Okay, so I am not going to sugarcoat anything about this conversation and just let the chips fall. It did not coincide with the company. That was just a coincidence. Portland was and is a lovely place with incredible people. The problem for us was that the experience of COVID and how the city and the people reacted to COVID shocked us and revealed to us that we were not as closely aligned with the people in the city around us as we expected, which it was a bit of a shock, and we had a few kind of shocking experiences. So COVID in general, we took seriously and we played ball, but the city dragged its feet and kind of went around the bend on being careful and became ideological and that really impacts your community and your kids. And we felt very lucky. I was running an e-commerce software startup and I had this strange experience of my company absolutely booming during COVID, which is a weird something I was very grateful for because everything was so scary and all of a sudden I'm looking at my graph and straight up into the right, so I should feel lucky and we did what we could. (18:55): So here's a perfect example. COVID hits and we start to understand what this means for teachers and for schools. And when I see that, I'm like, I got a business that's booming right now. What I'm going to do is I'm going to donate. How can I help? How can I get my company to let's say buy 10 teachers the monitors and the microphone and all this stuff they need for Zoom and the whatever they need? And a lot of the response, my wife by coincidence was president of the PTA, and our impulse immediately was like, we got to help. What can we do? And the first bit of cracks in our relationship with the city was the response to that and people said, no, don't donate because the less fortunate communities can't donate so our teachers shouldn't have nice stuff. And I was like, that's weird. To me, in all of my value system, that felt very off and my wife was also responsible for this big annual fundraiser for the school. (19:59): Same thing. Instead of going overtime on the fundraising to help even more, people said, no fundraiser this year because our community has more resources than others, and so it would feel wrong to raise money this year when others can't. And I was like, guys, what are we talking about here? This is our kids. And so these cracks and these cultural cohesion and then the crime hit and then the response to the crime and then riots and I was like, you know what? My understanding of the relationship between citizen and government, not only does it not fit with the way Portland does, the people around us don't want it to fit. We're the odd people out. That started to kind of dawn on us in this irreconcilable way where it was like, I don't want my kids to grow up in this environment with this understanding of how government should work. That got to the point where we were, that was at the macro level and then at the micro level, we weren't comfortable letting our kid walk to the library three blocks away because between here and there were several tent encampments with people doing drugs. And that's when we were kind of like, you know what? We went too far left. We got to go back to the middle. Adam Fishman (21:16): Yeah. Well there's a theme here though, which is prioritizing family first and what your family needed. And you didn't want your kids walking in that environment. You didn't want them growing up in that environment. And so it wasn't maybe that way when you got there, but it changed and then you prioritized your family. Jordan Gal (21:36): Yeah, it would've been much easier to stay. I had an office, I had a business, I had all these other things much easier to stay, but if you think about the kids and how they grew up and their education and all that, and that's why we are in the Chicago suburbs and we have made a devastating trade off. The food here is so mediocre compared to Portland. Oh my God. It is tough. It's tough. But the kids have this amazing school. My kid rode her bike to school this morning. Yes, they're basic. They go to Starbucks, but they have a great education and safety and in my prioritization, that's what mattered more. Adam Fishman (22:11): Okay. Well, I want to talk about something you brought up earlier in the show, which is talking about money and for context, your kids are 13, 11, and nine, is that right? Yes. And I would consider this to be, you mentioned it's a little contrarian how much you lean into this. Some people might see it that way. Others would be like, no, that's totally normal. But hey, we talk to a lot of different people on this show and then we appreciate diversity of perspective. So I'm going to say that you have a somewhat contrarian dad superpower and that is talking about money. A lot of families don't know how to do that with their kids or they think it's taboo or they want to shield their kids from that, but that's not how you approach it. Now you also mentioned that in your household growing up it was the extreme other direction, which was like, I know the P and L of everything in the business. I could do the accounting for this business if I needed to. How do you approach this in your household and how do you and your wife strike that balance? Jordan Gal (23:14): I find that it's not necessary for them to know the details of their family financial position, whatever. That's not necessary in order to understand the world of money and business and how things actually work and what is behind some of the things that they're seeing and experiencing. So I guess maybe I make it less personal. I talk less about ourselves and I take the opportunities where I see them in our day-to-day lives and experiences to just peel back a few layers. And what I mean by that is, I mean let's just say we go on vacation and you go to the shaved ice stand in Maui that we were just in a few weeks ago and there's a giant line and this is a booming business, and that's just interesting. That's just cool and you admire the people who did it and you want to know how they did it. (24:12): All right, so maybe I'll prompt some questions around the curiosity around why do you think this has so many people, but all the other shaved ice spaces that we drive past don't have this number of people? So maybe I'll kind of poke at that at how reputation becomes established and how the quality of the product leads into people talking about it and enjoying it and then that joy is infectious. And then maybe I'll say it'll be our turn to buy and everyone will order and then I'll pay. And I guess what I don't want to do is I don't want them to feel completely separate from that last act of payment, of transaction, of the exchange that just happened. And so when they become aware, I just paid $55 for these shaved ices for the five of us and everyone's happy and we sit down. Maybe I'll prod there and I'll say 55 bucks, that's interesting. (25:06): What if that's the average? How much money are they making from the people online right now? And they'll count 20 people and say, okay, what's 20 times 55? And we'll kind of go through that and I say, okay, how many times do you think this goes around a day? And it'll start to kind of dawn on 'em like, oh, this place is making like $25,000 a day. Okay, how many days a week are they open? So I'll start to poke into that and I'll say, do you think they just keep all that, but what about the people behind the counter? Do they need to pay them? What about the ice? What about the electricity? So I just want them to understand what's going on in the world around them as it relates to money and business. I try to make it fun that way without being like, do you know how much I paid for this vacation? You've stopped fighting with your sister. Adam Fishman (25:50): And that way you're also kind of helping your kids develop some empathy for what it takes to run a business and just curiosity in asking questions and going a level deeper, which is really interesting. Jordan Gal (26:03): What I hope it leads to is an awareness of where they sit in that whole ocean of economy. And so when they choose where they want to go and live and exist, they at least understand what's happening around. It reminds me of a great graduation speech by David Foster Wallace. He has a graduation speech if you haven't heard, it's unbelievable. It's called This is Water. And he talks about the importance of education in, I don't want to spoil it, but it's about a goldfish in water. And without education you don't even understand that you're in water. And the value of education is just giving you this understanding of where you even are to begin with so that you can start to understand and have a level of awareness as you go through the world. And a lot of people do not understand at all how the economy works and it makes them resentful and it makes them envious and it confuses them and leads 'em into bad conclusions. (27:07): And I don't care what they end up doing as long as they are really interested in what they're doing, but at the very least when they leave the house, I want them to have an awareness of how this stuff works and ideally this is where it gets into pushing them toward entrepreneurship versus not. My impulse is I do want to push 'em toward entrepreneurship because I think it leads to happiness. That's my goal in pushing them toward entrepreneurship, not so they can make a bunch of money and take care of me when I'm older. I hope they don't have to take care of me, that's my problem. But because I think it leads to happiness and so I can't help but just infuse their non-academic education with an understanding around how this stuff works so that they understand the power of ownership and equity and not having to do all the work yourself and all these things that it took me a really long time to shake for my family business experience. Adam Fishman (28:05): And how do you instill this in them and gently push them towards entrepreneurship without being too forceful and maybe creating organ rejection there? Jordan Gal (28:18): I try to explain the difference between employment and ownership, and that is like maybe we're getting into a little bit of weird stuff that I maybe have some guilt around how I talk to them and I end up connecting our day-to-day lives and our expenses and we will come across something they want, a pair of Lululemon pants that costs $80 and I will just poke them. How long do you think it takes for someone working at the Panera that we just picked a bunch from? How many hours do you think it takes them to earn one pair of Lululemon pants? I try to illuminate how hard it is to make money and how valuable money is. And if they have certain expectations, they should be aware of what it takes to meet those expectations. You want all this nice stuff. You need to understand what that means and maybe that is an insidious push toward entrepreneurship because it's kind of like a gentle way of saying you need to make more money than you think. You need to make more money than the average person. And that's pretty challenging when someone else is deciding what you get paid. So that's kind of my nudge. Adam Fishman (29:37): Yeah, no, that's fascinating. And one the things about entrepreneurship is that it can be stressful. A lot of people are depending on you if you were employing a bunch of folks and you're the boss. And I'm curious how you have separated or balanced the stress that comes from building so many different businesses. How have you managed how much of that you expose to your kids on the entrepreneurial roller coaster? Jordan Gal (30:08): Yeah, I think for the most part I have been successful at shielding them from what I think they should be shielded from. Not everything. You should see that it's stressful and that sometimes you work late and sometimes you say, no, I can't do that. I had this other thing and I have no choice. And you don't want Daddy to go to LA for some random conference that he doesn't really want to go to anyway, but I'm going to go anyway. But I think for the most part I've been successful in doing that and I think that a lot of that comes from my experience with my father and not being shielded from it. My father did the best he could and he really didn't have peers and he had three sons and we were kind of his peers. So we shared the same way you and I likely share with our peers our stress. (30:46): I have not always been successful at it though. And at my worst is when I take my work stress and I allow that to ground my patience down to a very thin layer. And then it's not work that puts me over the edge. It's my kids that put me over the edge and they see me go through the barrier of my patience and into my anger and they don't understand that there's a whole bunch of stuff that led to it. That's the worst of both. I shielded them and then they kind of got the worst of it without even understanding that a lot of it is a result of me shielding them. So I try to talk about it and communicate and I try to have release valves. Adam Fishman (31:31): And with three differently aged kids, do you have to meter or kind of approach the conversations differently with all three of them and what you're revealing or not revealing? Jordan Gal (31:44): Yes, and I just thought about this more because Passover with this last weekend and in that ceremony there's the concept of different types of kids, different types of personalities, the wise one, the one that questions, the one that's quiet, that sort of thing. And all three of my kids are very different. So the ages make less of a difference in the personalities because they're very close together. It's within four years, all three of them. And the youngest one is a very bright nine. There's no need to talk down for her age, but the personalities are different and some are more sensitive about certain things. My 13-year-old is like a peer and always has been. This is the oldest one that we went to Berlin and is just, she's always been like that. So when I catch them individually, I will like some of the examples we talked about, hey, this thing we come across in life and maybe this surface to scratch there, it will be tailored toward that person's personality and interests. (32:44): But when I talk to all three of them, I don't really change much for each other and I do, what I find really interesting is the comments I get from the different personalities when we're openly talking about a topic. One will immediately see the other person's point of view. One will look at it from a more selfish point of view. The other one will be more skeptical. So that's fun because then you start to reveal these individual personalities and preferences and points of view. I like to make sure that they don't think that I know what I'm talking about. I regularly say, "Your dad's terrible at a lot of things, but he's good at these other things and that's my area of focus. The other stuff you can make fun of, there's other stuff I'm pretty confident in and maybe you're like that also." Adam Fishman (33:30): Much like this podcast where I don't pretend to know anything because that's in fact the truth and I'm just getting input from other dads. One of the things that you mentioned was sometimes with work stress that you blast through that barrier. There's a lot underneath the water, just the tip of the iceberg. And there's a lot that maybe you get angry or something and it's not your kids, but they are maybe the straw that broke the camel's back. What do you do to recover from that with your kids when inevitably it happens, which it happens to I think every parent and they're lying if they say that it doesn't? What's your strategy or tactics to kind of recover from that angry moment or stressful moment? Jordan Gal (34:13): My immediate reaction is pretty extreme guilt. I will remember for years making a rude comment to someone by accident and seeing them be hurt by it and I will carry it around for literally 10 years. It is not good. And so if that happens, I immediately retreat in terms of emotionally into guilt. And then the way I get out of it is I explain myself fully and I probably do it at a bit too high of a level of maturity with the kids, but I'm like, your dad's very stressed out because he's fundraising right now and if I can't raise money for this company, then everyone's going to lose their jobs and that's why I'm really stressed right now and you just said something and I got really angry, but it is not your fault that I'm that angry. That's my fault. So I'll kind of just go extreme direct honesty because I want to remove the blame from them to see I'm the adult here, but no matter what you said, I don't have the right to react that way. It doesn't matter what you said, it doesn't matter what you did wrong, how wrong, whatever. My reaction has nothing to do with you, that's on me. Adam Fishman (35:35): And do you find that doing has helped your kids kind of do the same thing when they get frustrated or angry about something? Are they learning from that behavior? Jordan Gal (35:46): I hope so. I think that's hard to see because they're so close to us. I think other people see that and whatever emotional maturity they have. I also am pretty adamant about it because I have three daughters and I want them to see what level of a man confronting emotions and honesty and blame and all that stuff. I want a model. This is the healthy version of it. Do not accept less than this. Adam Fishman (36:19): Oh, I love that. Love that perspective. Thank you. I want to stay on this topic of the entrepreneurship roller coaster for just another minute or two. We talked a lot about your relationship with your kids and how stress can manifest and you can break through that wall. There's one person we haven't talked about much, and that's your wife. What do you do to maintain healthy relationship with your wife? What are your priorities with her while there's this company stress happening all the time? Jordan Gal (36:47): I think I owe her very direct honesty for this long of a stretch of time. You do not want to blow smoke, you don't want a false confidence that's not going to go anywhere good. We have tested some of those boundaries around what I owe and not owe and what she owes me and where all this stuff, where these boundaries should live. We have a relatively traditional arrangement in our marriage: husband, wife, three daughters, she's the mother, I work, she stays at home and is very involved in the community and extremely involved in their lives. So it's pretty traditional overall. But she's very much a modern, educated, strong woman. And so we have figured out what our version of modern marriage and family making is. So I think the communication being together for 25 years and a lot of that being married is by far the most important thing. (37:50): She's been on the rollercoaster with me and sometimes that rollercoaster is financial, sometimes good, sometimes bad. And along the way to where we are now, we had some ups and downs and in the downs is where it gets kind of interesting in terms of what is this thing. So we have had the conversations many years ago now we've had the conversation of she came to me and was like, when is it just enough and time to just go get a job? It was a very important boundary for us to kind of mark in permanent ink because there is no enough. This is who you're with and who you're about to marry. This is me. So that question is actually outside of the boundaries and I use the analogy of, hey, if I were extremely passionate about a line of work that did not pay well, but that's what I cared about, we wouldn't be talking about, hey, maybe it's time to quit this thing you really love doing and go get a higher-paying job. And so entrepreneurship in that risk-taking lives on its own in how to interpret it and how to deal with it. So we'd have to have all these conversations. I have a very strong hero complex, I'm just going to pretend to be my therapist real quick and talk about that. Adam Fishman (39:08): Sometimes I've heard this show is better than therapy. So here we are. Jordan Gal (39:12): I have to tell you, speaking of therapy, I came into this conversation with you, a ball of nerves. So the irony of me scheduling this today is something else. My youngest daughter, my nine-year-old is in the lead role of Moana today, and I am so nervous. I have barely been able to do any work. So the irony of this, I'm being overwhelmed by parenthood right now and watching your kid find something that they're passionate about and my favorite part of it is that self-motivation. She has found something that no one needs to say, hey, you should practice. She's like, well, it's good that I know my lines and my dances, but if I know everyone else's, then that's better. So I'll also practice everyone elese's. And you're like, oh, self-motivation. And that's actually what we're after. I don't know if it's in contradiction to traditional schooling, but they're often opposites. And one of the things I have an extremely hard time with is pushing my kids toward academic focus and excellence, but also saying, yeah, but make sure you find what you really like because that's more important than this thing that you are supposed to and supposed to do and you're supposed to accomplish and you're supposed to do next and all this other stuff. Adam Fishman (40:29): So obviously you and your wife have been together for 25 years, go blue, but I'm sure there are occasionally some things that you don't agree on when it comes to parenting. What is an example of one of those areas? Jordan Gal (40:38): I'm a very, very strong advocate of speaking up. From friends and family, that's kind of what I'm known for. Like, oh, Jordan will just say the thing that needs to be said even though it's uncomfortable. And my wife is a very sweet person and her personality, the way she grew up all that, she does not want to hurt people's feelings and we butt heads on that. It's a little example, last weekend my wife and I got to dinner with some friends. Our oldest is old enough to babysit. It's a few hours, just watch a show. But then because kids know where everyone are these days on the Snap Map, a bunch of boys come over and they walk into the house, even though she said, my parents aren't home, you can't come in. And they come into the house and the 13-year-old boys, relatively harmless but also not okay, unacceptable, not unacceptable thing to come to the house and do stuff and go here, (41:31): even though our kids are saying our parents aren't home, you have to leave. The next night, the same boys are across the street. In my head I'm like, are those the boys? Because it's time to say something because if that's unacceptable, they should know that I find it unacceptable so that we know where we stand here instead of me thinking a certain thing and then thinking a certain other thing and them being wrong and not knowing it. My wife saw me come out of the car, walk in the direction and was like, no, no, no. And my daughter was like, please, dad. So I didn't. But that's kind of a perfect example of this, like, hey, you need to say something and my wife prefers not to say anything and it's up to my kids on how they approach that. I think that's a personality filter. Adam Fishman (42:16): If you could rewind the clock back to the time right before you had your first kid, with all the things that you've learned going through in the process of raising three of them, what advice would you give the younger version of yourself? Jordan Gal (42:31): I think I had the right goals in terms of freedom, be close to them. I didn't always work from home. I had an office, but I had a lot of flexibility. I didn't miss anything. So I think I had a lot of those things. I think a lot of it are the cliches, the recognize how fast this goes, get off the damn phone, enjoy yourself more, roll around. I needed to relax more. That would be my biggest advice. I have a pretty unhealthy level of paranoia around safety. It's a DNA thing, it's a Holocaust survivor's Israel trauma generational stuff here. And I have had difficulty managing that as a parent. That's what a lot of the therapy that I've done has been centered around because I don't worry about something bad happening. I visualize it and then I feel it as if it happened. And that's not good. (43:31): That is not healthy for you. And also the way it comes out for your family when you're like you basically trying to hold them close and don't go here, don't cross the street and look both ways and just that stress. I wish when I was younger, before I had the kids, I had more tools and a better understanding of that being my problem and really do your best not to force that down onto my kids. We've kind of turned it into a little bit of a joke. My nickname is Captain Safety beyond the cliches of get off the phone, enjoy and be more present. That would be one thing looking back that I really wish I kind of addressed more. Adam Fishman (44:11): With technology and in technology and around it, especially with three daughters, what is the relationship that you want your kids to have with technology as they progress through life and get older? Jordan Gal (44:25): At the first level, I think into the future, and I think you know what you should do? You should learn engineering because that's important. In general. I want them to be aware of what's happening. So I had this perfect conversation with my teenage daughter. We talked about Snapchat and we talked to her openly, hey, we're about to put a bunch of restrictions around your phone. The reason we're doing that is because we love you and how that's connected to the technology is this thing. Let's look at how many hours you spent here and there. And we had this conversation about Snapchat and we said, look, the other day you're in the car with us. We're driving. You're in the passenger seat. I'm talking to you. I think it was her mother was driving and she said, look at the moon. It's beautiful right now. (45:08): And my daughter kind of looked up and go, cool, and just went right back to the snaps. She was like, kid, literally beauty around you. You're missing by staring at this phone. She's like, well, I have to get back to them because they snap me. When they snap me, they can see that I opened it. If they see that I opened it, they know that I haven't responded yet and so I want to respond so they don't feel like I'm being rude. And then I was like, timeout, that's great for our friend Evan Spiegel, which is hallelujah, but it's not good for you because what you're in is you're in a little loop designed by a UX designer and you are playing right into their hands. So you message them and then they see it and they feel guilty, so they message you. And that's just ad impressions. (45:52): So I just try to give them an awareness of, hey, you are in control of this stuff. Do not fall under the spell of these things that are very powerful. And unfortunately because you're young and we can't expect you to have all that awareness, we're going to impose some of that control on you. But this is why. I want them to be aware of it. I want them to take advantage of technology. Everything I've done in my career is I take advantage of it. I work from this house right now and that allows me to be all over my kids' life. I just went to Panera to pick up one of the kids and drop them at school. My wife had to go somewhere else after the doctor and whatever else. And that's all the freedom that came out of technology. Same with the 18 month trip and everything else. I want them to take advantage of it without being taken advantage of. Adam Fishman (46:37): I love that. I love that. That sounds like a great lesson for us to end on before we get to lightning round. Last question for you. How can people follow along or be helpful to you? Jordan Gal (46:49): Okay, so I've run this business right now. That is so, so interesting. Some businesses I've had were great, some were boring. This one is a lot of fun. It's an AI company and we help small businesses by providing them a phone agent, so an AI that answers their phone when they can't get to the phone. And it's this very, very straightforward application of AI. I look at it as an arbitrage of like, here's this amazing tech, and then here's a bunch of people that don't care about the tech. They just have a problem. And I just help them take the tech and give it to them in this way that's very effective for them. So if you want to follow along with that, you can go to heyrosie.com. And then I'm mostly on X, Twitter, a little bit of LinkedIn, but mostly X @JordanGal. And eventually I'll start a podcast over the next few weeks. Adam Fishman (47:37): Well, we will link to all of these things in the show notes and send some traffic to Rosie, which I find to be a fascinating product. And I'm even thinking about how might I leverage this as a solopreneur. So something to think about. Very cool. Thank you. Jordan, are you ready? As ready as anyone can be for lightning round? Jordan Gal (47:58): Yes, yes. I'm not, but yeah, let's do it. Adam Fishman (48:01): Okay. What is the most indispensable parenting product you've ever purchased? Jordan Gal (48:06): The pack and play. That's the only thing that comes to mind. A portable way to ignore where you are. Adam Fishman (48:11): What is the most useless parenting product you've ever purchased? Jordan Gal (48:14): Probably those cameras that helped you spy the baby while they were napping. Adam Fishman (48:19): True or false? There's only one correct way to load the dishwasher. Jordan Gal (48:23): Oh, that's true. My way. Each dishwasher has a single correct way. I just happen to be able to find that. That's all. Adam Fishman (48:32): Okay. Aside from talking about money in the appropriate way with your family, what is your other dad superpower? Jordan Gal (48:41): I think I'm pretty funny as the dad. Adam Fishman (48:43): Okay. Jordan Gal (48:43): I got bad jokes. Adam Fishman (48:45): Okay, well we might come back to that. Can we also talk about Captain Safety? Who calls you Captain Safety? Is that your kids, your wife, everyone, the neighborhood? Jordan Gal (48:54): It started from my wife and trickled down into my kids. Yep. I drive nice and slow. I don't see the point in driving fast. I don't see the point. We're going to get there probably at the same time, regardless. So... Adam Fishman (49:06): If your kids had to describe you in one word, what would it be? Jordan Gal (49:10): Ambitious. Adam Fishman (49:12): Okay. What is the most frustrating thing that has ever happened to you as a dad? Jordan Gal (49:17): My kid, my oldest got really sick and was intubated in the hospital for three weeks. I was twisting in pretzels, which that was the most frustrating, crazy experience. Adam Fishman (49:32): Wow. Jordan Gal (49:33): Yep. Adam Fishman (49:33): What is your go-to dad wardrobe, Fiori pants, marine layer shirt? Jordan Gal (49:40): Everything real stretchy, real comfy and stretchy. Adam Fishman (49:43): What is the favorite ages for your kids? Jordan Gal (49:46): Right now is just perfect. If I could keep this, it's older, then the baby craziness, diapers, feeding, look out for the stair thing, but not so old that we are an afterthought that just drives them places. It is just the best right now. It is the best. Adam Fishman (50:08): Got it. You're in the sweet spot. Jordan Gal (50:09): The sweet spot. Hallelujah. Adam Fishman (50:10): Okay. How many dad jokes do you tell on average in a given day? Jordan Gal (50:15): They would say many. I usually know when it's a dad joke, so maybe two, three times a day. I'm like, ha, I'm in on it. I know it's funny. I know it's not. Adam Fishman (50:27): Yep. You have a teenager. What is the most embarrassing thing that you've done in front of her as defined by her? Jordan Gal (50:34): I have done some embarrassing things. The most embarrassing thing was not in front of her is walking to a wall at a conference. Glass wall. It was impossible to see, but it was in front of a lot of people. I can't really think of something super, super embarrassing with them. But last weekend when she and all of her friends who are like dancers were in our kitchen hanging out, none of them could do the worm. And who did the worm? Dad did the worm in front of everybody and they were like, damn bro. You got moves? Yes. Adam Fishman (51:01): Wow. Jordan Gal (51:01): Yep. Adam Fishman (51:02): Wow. If you've learned anything at the University of Michigan, it was how to do the worm. Okay. What is your favorite kids' movie? Jordan Gal (51:10): I love Bee movie. It's Seinfeld and it's for kids. It's great. It's genius. Adam Fishman (51:16): Is there a nostalgic movie that you cannot wait to force your kids to watch? Jordan Gal (51:22): Oh, that's tough. I grew up with two brothers, so three boys is a very different thing entirely. There are some TV shows I want them to watch, like The Wonder Years and Parenthood. So just some of that stuff. Some of the other movies, not yet. It's more historical Schindler's List type stuff. Like okay. They have some of that waiting for them. There's no rush. Adam Fishman (51:42): Do you have a favorite dad hack for road trips or flights? Jordan Gal (51:47): I've had sleep issues. I got a CPAP machine. I was diagnosed as a narcoleptic at one point. I have some sleep issues. I figured them out since. But I get drowsy behind the wheel and my hack is sunflower seeds. So when I grew up, a lot of my friends were baseball players. I played lacrosse, but they taught me how to stuff like 30 sunflower seeds in one cheek and move one over, crack it, spit it out, eat it, and then do the next one. So my kids know we're going on a road trip. Dad's got to get some sunflower seeds and a cup and be like, dad, that's gross. And I go, sorry, I'm awake while all of you guys are asleep. That's my hack. Sorry. Adam Fishman (52:20): Your kids have not adopted that hack yet as a form of entertainment for themselves? Jordan Gal (52:25): No, they're comfortably sleeping with their snuggy or something in the back while I have to drive six hours to Northern Michigan. Adam Fishman (52:31): Yes, yes. Oh, love that. Okay, last question for you with three kids and you live in the Chicago suburbs, what is your take on minivans? Jordan Gal (52:42): So my wife drives a minivan and right before we got the minivan, we were never minivanners. Never. Why would you want a minivan? We're we're too cool for that. There's no way. And then we got an SUV and two weeks, two weeks in to having an SUV and my wife looked at me and said, I made a huge mistake. It's my birthday. I will do anything if you come back today with a minivan. And I was like, got it. So we've had a minivan ever since. Now our kids are older and her lease is up and this is the big debate in our house. So I do not want to drive a minivan ever, and I prefer my SUV, but my wife loves her minivan and so I'm married to a minivan. Here we are. Adam Fishman (53:25): Alright, well, I'm excited for the advances in minivan technology for your next lease or purchase. So Jordan, thank you so much for joining me today on Startup Dad. Your company is Rosie. We will send people to check it out at heyrosie.com and people will follow you on X and all the other places. So Jordan, it was a pleasure having you today and I wish you and your fam all the best. Jordan Gal (53:51): Thank you very much, Adam. Great to be here. Adam Fishman (53:53): Thank you for listening to today's conversation with Jordan Gal. Startup Dad is available in all your favorite podcast players and YouTube. Just search for Startup Dad to find it anywhere you listen to podcasts. Thanks for listening and see you next week.