Let's Ride w/ Paul Estrada
Who else is trying to figure $hit out?
Welcome to Lets Ride w/ Paul Estrada – the podcast where a dad tackles the big questions of life, career, and everything in between, by talking to interesting people that have the answers!
When I turned 18, I lost sleep at night with questions that Google was not yet sophisticated enough to answer: What career should I pursue? How can I be more than just average? And how do successful people get to where they are (was there a secret handbook I didn't know about)? After 22 years of pondering these existential dilemmas, I’ve finally pieced together some answers – An answer that is sufficient for now, but one always in need of refinement.
Join me each week as my 6 ½ year old son, Adrian, throws out a thought-provoking question or idea, and I invite a guest to help me sufficiently respond to him. From learning about money and investing, to finding a passion in life, and exploring careers that can be meaningful for you, we cover it all with a dose of humor and some soundbites of wisdom.
So, if you’re a parent or a young adult navigating these tricky waters, or if you want confirmation that other people are sometimes just as lost as you, you’ve come to the right place.
Let's Ride w/ Paul Estrada
Startup Entrepreneur: From Banking to Reinventing Umbrellas
From prestigious finance careers to launching a startup revolutionizing the humble umbrella, Reed Jacoby's entrepreneurial journey demonstrates that sometimes the boldest business opportunities aren't flashy tech innovations but overlooked everyday problems.
Reed's story begins in Michigan, where despite not being the academic superstar, he leveraged his natural talent for building relationships to secure admission to top business programs and eventually land coveted positions in banking and private equity. Working with ultra-wealthy clients gave him a crucial insight: true wealth creation doesn't come from collecting paychecks but from ownership. One pivotal moment—a client casually calling to wire in $22 million—sparked Reed's realization that he needed to create something of his own.
The entrepreneurial path has tested Reed's resilience at every turn, especially during fundraising where "it's probably one yes for every 50 to 200 no's." Through it all, he's maintained that this journey, while "by far the hardest thing I've ever done," is also "one of the most rewarding things you can do."
Ready to reconsider what entrepreneurship might look like in your own life? Reed's advice is refreshingly honest: find something that genuinely excites you, recognize it will take longer and cost more than expected, and prepare for constant challenges. Most importantly, know yourself—some people need to "burn the boats" while others can start more cautiously. Whatever your approach, Reed's journey proves that with enough determination, you can handle far more than you think.
Let's say mom wants to make a company that she would like, then like how would you like, like? How do you start it?
Speaker 2:So yeah, you gotta find a business that you would like to do, something that's interesting to you, and then you can just yeah, you can make it. I mean, yeah, that's the idea is that you would make it.
Speaker 1:So you don't even have to like do, like a meeting or something.
Speaker 2:Not really. It's like the podcast is kind of a business where I just started it by myself and I had an idea and then I just made. I'm making the idea happen, I'm just doing the work and then it slowly is building into a company.
Speaker 1:But podcasting has been around for a long time.
Speaker 2:Yeah, it's been around for a few years. Just a few years, yeah. But can I ask you have you ever heard the word entrepreneur before? No, do you know what it means? No, it means somebody who starts their own business and they don't work for like anybody else, they just work like they're their own boss, like they start their own business and they just work by themselves or they work for themselves.
Speaker 1:I'm going to make a company and I think it's going to be called Robot. I think this is a good name for robot making robot making. So we're gonna make like, basically robots, then like, like give them to stores and then the stores would pay us money. How much money?
Speaker 2:like they'll sell it all right now.
Speaker 1:That's a company, so you have a product, which is your robot, and then you sell your robots to stores so like there's like one place that has computers, where, like, everybody can think of bright ideas, and then there's another machinery place that makes robots, like with the people's ideas, and then we buy trucks and that's on to the stores.
Speaker 2:That sounds like a great company.
Speaker 1:I know there are already companies like that, but not many companies are like that, that's true.
Speaker 2:All right. Well, that's a great idea to start. So how are you going to start?
Speaker 1:I'm going to start by making one building and then put all the furniture. Okay, got to have furniture like boxes, like packages for robots, and then one's going to be the parking lot and then the rest is all going to be the street parking, and then we're going to write a sign, and then we're going to make a big sign on the beautiful glass doors that says Making Robots.
Speaker 2:Our guest today is the visionary founder of Gilly, an innovative umbrella company. Nope, not that kind of umbrella company. We're talking about actual umbrellas, the rain accessory, the one you open over your head to stay dry on a rainy day, just to clarify. But before he was reinventing the umbrella, he was just a scrappy kid from the suburbs of Detroit, not the most academically inclined. He made up for it with his incredible resourcefulness, which eventually led him to one of the most prestigious business schools in the nation, michigan's Ross School of Business. From there, he carved out a path through banking and private equity. He was on his trajectory to a highly successful career, climbing the corporate ladder, when a series of soaking, wet walks from the tube to his London office sparked an idea. It was at that moment that he made the decision to leave his lucrative career behind and dive headfirst into the unpredictable world of startup entrepreneurship. I'm excited to learn more about his go-bigger, go-home journey. My guest today is Reid Jacoby.
Speaker 1:So let's ride. Let's ride on through the rain. Come on and take me anywhere that you want to be.
Speaker 2:All right. Well, we've got a first today. I think, uh, let's ride. I mean, we're, we're only in month number two, but we're going international already. We've got, um, we've got you a read. Where, where, where can we find you today?
Speaker 3:I am based in London, in London, exactly at this moment.
Speaker 2:Okay, I always think of what's that movie where he goes like you sound like you're from London. Oh yeah, you don't sound like you're from London. I love you, man. I think, yeah, I love you yeah one of those right the best.
Speaker 3:But yeah, I'm still hearing some of your, is it Michigan roots in the voice. I'm not really hearing that London accent. What's going on? Yeah, very much, so Very much. From the suburbs of Detroit and I spent a little time in your neck of the woods, went to New York and then popped over here for the last five or so years.
Speaker 2:Yeah, and what's it like, been living internationally.
Speaker 3:It's been good. I think London's a pretty soft landing for Americans. We speak the same language, there's a lot of the same customs, so if you're going to live abroad, london is a good place to start, and then maybe you can venture further afield later on.
Speaker 2:Yeah, that's awesome. I spent some time in Madrid for a study abroad. The intent was to learn Spanish, and what it ended up to was just six months of just having a good time and going out like five nights a week.
Speaker 3:So yeah, yeah, I did a study abroad in Madrid and the credits ended up not transferring, so I just spent all my time in that club Capital until 7 am every night. There you go, and yeah, that was a good summer. But now I'm a bit older. London's a bit different.
Speaker 2:All right. So we're getting a little bit of sense already of what young Reed Jacoby was like Back in the day. But I want to get straight into it. And the first thing that comes to mind, reed, as going through your credentials, your LinkedIn, doing some snooping around, and I look just at your resume as, just academically, you went to Ross School of Business for your undergrad, which is consistently ranked top 10, 15 business programs in the US, if not the world, and then after that you go to London Business School to get an advanced degree, your MBA, which, as I did research on that, is like the number one, number two international MBA program in the world. So, like your academic pedigree is like ridiculously off the charts. So I have to start there. So just, I mean, are you just like some? Were you some kid genius? Or like, how did? How did you end up with that kind of resume?
Speaker 3:No, no, no, it's been. It's been a lot of luck, and I think I was never the smartest kid in the classroom, so I made up for it. Outside of the classroom I was that guy who was the captain of the sports teams and got some help with his essays, so that's kind of how I snuck in.
Speaker 2:Yeah, well, let's start with Michigan. So I know you're from Michigan, so maybe the requirements were a little bit more lean. But I don't know for those that think about that type of academic pedigree. I went to what I call the poor man's UCI. Uci is UC Irvine, which is a UC school. It's a higher end school. I went to Cal State, fullerton. It's kind of at that time it was pretty easy to get into. Not going to lie, it might've been the only school that I applied to. Thankfully, I got into that school and the reason why I picked it was because it was far enough away from my parents' house that I could move out, but not so far that I couldn't go home on the weekends and have a home-cooked meal 100%. So how about that for college requirements, right?
Speaker 3:Yeah.
Speaker 2:But yeah. So how did you pick Michigan? Obviously, Michigan's a very well-known school. Was that always your dream, being from Michigan, to want to go to that school, or how did that come about?
Speaker 3:Yeah, well, a bit of a similar idea, I think. Growing up, my best friend who lived across the street, his parents, went to Michigan and so from a young age I was able to go up to Mud Bowls on Saturday and watch all these guys play and then go to the games and it was just such a good time that I became enamored with the University of Michigan. And then, as I got older, you know, my grades were good enough, but just barely good enough, and I think it's harder to get in from out of state than it is for in-state kids. But I kind of knew the rules to the game. So I padded that with some leadership stuff. I was captain of the soccer team and the track team and stuff like that and then kind of fortunately got in and it was right in our backyard. So, similar to you, I'd come home every couple of months but my parents didn't visit every day. It was kind of that perfect fix.
Speaker 2:So I'm thinking about my own journey as well. So I was not that strong academically either and, like I said, I got into Cal State, fullerton, somehow, not knowing that they had a really good business school as well. That being said, like I really wasn't interested in working that hard academically in college either, and so I picked I was doing my general ed and I took a psychology class and I'm like, oh, this looks pretty easy, I'm going to pick psychology as my major. And so I did that for like a semester and I said this is why am I doing this? I'm doing this because the business school scares me.
Speaker 2:I was not very good at math in high school. I think I failed algebra one, I failed algebra two, I failed geometry. Basically, I had to take every single math class again over the summer. And when I looked at the business requirements to graduate from the business school was like accounting 201, accounting 202, econ, finance, statistics, business calculus I'm like, oh, come on, there's just no chance that I'm going to be able to, there's no way that I'm going to pass all this right. And so eventually I had to just realize like, hey, man, I got a business degree is really what I need for me, for my personality. I'm nothing against psychology. There's great psychology. My sister's a psychologist. That's a great degree as well.
Speaker 2:It just was not for me and I picked it for the wrong reasons. I picked it because I was scared of math and I sucked it up and ended up doing it, and so I'm grateful now that I did that, because I use math so much in my day-to-day life, but it was definitely not top of mind. So, yeah, and then I guess, just to piggyback off that as far as what you were doing was, you're now going to this prestigious school, like you said, and I'm assuming, a lot of the same things. Right, you're having to take a lot of the same types of classes. The only difference is you're doing so with international superstars in terms of academics, right, and also local people. So the one thing I will say about that is, I'm assuming, being surrounded by so much talent, like did that feel like you had to elevate your own game and like, do you feel like you were able to do that?
Speaker 3:Yeah, it did feel like I had to elevate my own game, and I'd be curious at some point to hear whether or not you had to retake all those classes in college too. But-.
Speaker 2:Three, three of them. Yes, thanks for asking Okay.
Speaker 3:Cool, cool, cool.
Speaker 3:Yeah, definitely had to elevate my own game, and I think what was really interesting was that you know, as I mentioned, most of the grades were on a competition scale and I couldn't compete with these kids really, and so it was a super challenging rubber meets the road type situation where you don't want to fail out but you're just not.
Speaker 3:You're not at their level, and so you have to kind of readjust and find ways to make up for those scores, particularly on these tests where they're just more inclined to kind of do better and maybe they're just naturally smarter than me. But they were certainly also paying 50 grand a year to go to ninth and 10th and 11th and 12th grade, and so there's it's just kind of a different ball game and you meet head to head and it's just not happening for you. So how do you get around that? I think one other way that I really want to elevate my game was we were in school for a year and all of these great companies and banks from around the country were coming to Little Ann Arbor to meet us, and we're 19, 20 years old, and so that kind of combined with the people I was competing with.
Speaker 3:It sort of elevated my mindset where, yeah, it was daunting that my grades were very good and I couldn't compete with these people, but at the same time you kind of feel like, oh, maybe I can do something here, maybe I'm worthwhile, maybe I'm talented in a way I didn't know.
Speaker 2:Well, knowing what I know about you is that you are a very personable person, you make build relationships easily, and I just feel like you probably leaned into that right. And so you had this opportunity where, like you said, people are coming to see you just because of the flag that you're going to school under right, which is a huge banner and a huge appeal to people, and while the grades might have been there, it seems like you were savvy enough to recognize that and then say like, okay, well, I've got to lean into my personality and who I am and to build these relationships, to find myself an opportunity. Is that fair way to? Is that how it went?
Speaker 3:Yeah, no, no, no. That's exactly right. That's exactly right, and I think there were different kind of opportunities to do that. I think one way is you can get referrals and recommendations from other people. And one thing I recognized from an early age, but that was really hammered home in undergraduate business school, is that other people make the world go round. Whether you want to get into that business school, whether you want to get a job, everything starts with somebody else giving you the access, even in entrepreneurship it's the same exact thing, and so I use that to my advantage, without being disingenuous.
Speaker 3:but people, I think if you play it right and you're likable and you really want something, I think people pick up on that and they want to be around you. And so to inject that into situations where there isn't a standardized test to compete on, you can set yourself apart and get into places that you wouldn't otherwise get into.
Speaker 2:Yeah, and I think when people are thinking about colleges, football programs and all the glitz and glamour, the colors of the school, people care about those things and I get it. It's really fun and exciting. I think what maybe gets overlooked sometimes is the value of the networks that you can begin to build. Right Up until that point we're just kids, we're pretty much just surrounded by our childhood friends and family, and that's our network. But eventually you get to college and now all of a sudden you're surrounded by a lot of different people with a lot of different backgrounds and you can start building this network and that becomes what I say today is networks can be your biggest asset that you own if you do it properly. And so the one thing that you are afforded is okay. You get to kind of kickstart the amazing building of your first professional network. So I guess talk a little bit about it sounds like you did recognize that and just maybe talk about how you recognize that and how you began to build your network in that way.
Speaker 3:Yeah, sure. So I think you know it's a. I don't know if it's a cheesy thing or not, but it's a saying that your network is your net worth.
Speaker 1:Yeah.
Speaker 3:That couldn't be more true than you know when you start a company at some point, or when you're getting into college.
Speaker 2:Yeah, so you graduate out between keg stands and studying and networking.
Speaker 2:You graduate college, okay, you've got this great resume, you've got the school on your resume and you spend the first about eight to 10 years of your career as a W-2 employee, which means working for somebody, for a company, and you're in the finance and banking industry, right, and I'm assuming you were already on a path where it's like, man, if I just ride this out, I'm good man, I can keep climbing this ladder, I'll keep making more money. You were kind of already set out on this path. Well, first of all, is that true? And, if so, just quick overview of what was that first couple of years like, of just getting into the professional world and starting to build up your resume? Yeah, absolutely.
Speaker 3:So I had a really interesting experience in a preview of entrepreneurship when, after I graduated, I went to work for an uncle for a little bit in Los Angeles and he wanted me to run his peanut factory.
Speaker 3:And so I went in there and I had absolutely zero effing idea what was going on Not the slightest clue. I could not. I could barely even talk to people because you know, school is one thing, but you have no frame of reference for the real world, you have no idea how anything actually works. And so I went in there and said, okay, one day I'd love to be an entrepreneur, I'd love to own my own business. That's where the real money is made. But now is not the time and to this day, I have no idea how Mark Zuckerberg or Evan Spiegel or they started a company when they were 22. I just have no idea, because it's so hard to have some building blocks for your career.
Speaker 3:So I did the same and I went to work at JP Morgan in ultra high net worth private banking.
Speaker 3:So we were managing money for the ultra rich of Southern California, which was a great experience not necessarily managing their money, but I saw how real value is created when I was 22 years old, and so most of our clients quite a few of my clients yeah, they had 30 year careers in finance, and if you were in the New York JP Morgan office, you would have seen a lot of people who worked at law firms or banks for 30 years, but I was working on people who were farmers in Central California and lived in Beverly Hills in $20 million houses, and so there are all these stories rolling around about how people make real money.
Speaker 3:There are all these stories rolling around about how people make real money, but as an actionable next step. I saw that these guys used to call in and they worked at a private equity firm in Los Angeles and this guy called in one day when I was 23 years old and he said hey, reid, I'm going to be wiring in 22 million tomorrow. And I thought, and at the time and this guy was probably in his early 40s, and at the time when I was 23, I thought that sounds cool, I'm going to do that.
Speaker 2:Yeah, that sounds cool. Yeah, I'd say so, so.
Speaker 3:I'm going to pursue that. So then I started to look to looking and getting into private equity, which is buying and selling companies, but in order to do that first in America it's not necessarily true in the UK or overseas, but in America it helps to be an investment banking analyst, where you work on transactions.
Speaker 2:Yeah, so let's I mean, without getting too much in the analytics portion there's a couple of things I want to touch on, and that is help people understand what these really, really wealthy people know that we don't know in terms of how to invest money. I know this is like we could spend an hour, three hours on this. I get this is a super loaded question, but just at a high level, like what are certain concepts that they're doing that maybe your average person is?
Speaker 3:not, yeah, and I didn't get to talk to them for hours at a time, but most of them had started their own companies. And I think one piece of advice that is interesting and goes back to your idea in childhood of what wealth is is that when you're growing up you think if somebody's making a million bucks a year, they're rich. But I guess that technically is the case. But the people who are really rich, they own a piece, at least a piece of something, and that something grows into meaningful value. And so all of these people owned something of value. And of course there were those people who inherited a lot from their family, but for the most part they had made it on their own and it was just extraordinary to see the amount of money that they made doing something. And it took them a really long time and I'm sure it was extremely hard, but they did it.
Speaker 2:Yeah, that's the thing. The other thing that you mentioned, which is, I think, again in the media and things like that, you see these quote unquote overnight success stories of brands and things like that. But what I heard from you when you were talking about these clients was 20, 30 years of grinding it out and building these things. It's not the case that it's like, hey, I put a couple of years into something and I made $50 million. It was no. They grinded and risked themselves and their wealth to get over a long period of time?
Speaker 3:Oh yeah, totally, and I think for a lot of them it's probably not their first company. Quite a few of them have probably had some massive misses at points where other people would give up, and so you have to factor in. What's not on the page, too, is that they didn't just hit this. Put in three years, make a hundred million bucks. That is incredibly rare.
Speaker 2:Right. And then the last big thing that you mentioned that I want to touch on is you had what I'll call an aha moment, or a light bulb moment, when somebody calls you and says they're going to wire you $22 million.
Speaker 2:That's in his 40s and you're like aha, what's going on here, and it seems like that was a pivotal turning point for you, at least in how you were starting to think about your own career. So I guess just talk about if that was in fact the moment, just talk through how that kind of guided your thinking moving after that point.
Speaker 3:That was a major moment, and I think being there and seeing how wealth is created and I thought to myself, well, that's an incredible life.
Speaker 3:I'd at least like to take a stab at that. Continuing in finance, and the way that this guy just made 22 million bucks, isn't the riskiest thing that's ever happened. Quite a few people do it Not a lot make 22 million bucks and wire transfer it to their young banker, but nonetheless, that is in some insane risk, and so the way to get there is also what I learned through ownership. So in private equity, you would own a piece of a company and you make your money through what's called carried interest, which is effectively taking a percentage of the profits from you owning a piece of this company and then selling it. But it was kind of that process that informed my next step, which was to get into corporate transactions in order to then get into private equity, and, interestingly, I absolutely hated those jobs, but nonetheless it was a great learning experience. I think it's all a part of the path and it's all a part of uncovering more learning since you go.
Speaker 2:Yeah, at an important point there is learning doesn't stop after you get your degree right and so. But I guess the thing for you is you were super deliberate about taking on these different roles. Like okay, oh, I need this puzzle piece and then that puzzle piece now with kind of like this long-term vision of, okay, well, I want to own my own business. Long-term vision of, okay, well, I want to own my own business. I know now I want to own my own business one day, but before I do that, I really want to get these skills under my belt.
Speaker 3:That's exactly right, and I think I had in the back of my mind for the longest time that I would probably go to graduate school and after that, that's when I'd really start to mix it up, I'd start to take some risk, I'd start to put some weight behind myself, and I think that those building blocks were instrumental in order to build up the confidence, in order to build up the capital, in order to build up my network to make a success. I'm doing something on my own, because if I would have tried this at 22, it would have flopped within six months.
Speaker 2:Yeah, and then the last thing I want to touch on before we get into your entrepreneur journey is what I'd mentioned on, but I want to go a little bit deeper and that is the type of work you were doing. You probably could have continued on that path, made the right connections, kept going up the ladder and you probably would have ended up in the top 1%, 2%, 3% of people in terms of your earning power and things like that. So it was kind of like this you just go with it, you're already on it, just go with it. You're already on the path. But then you're like, nah, I'm going to let me blow this up and let me go try something super, super hard. So was that an easy choice for you? Or did that cross your mind too, of just like I can just keep grinding this out and get to the same end point that I want to get to?
Speaker 3:It definitely crossed my mind and sometimes it still does, depending on how hard of a day. But I think basically you know from a young age you're looking at salaries in the 1%. You know I haven't looked in a while but I was probably. I was definitely in that in my age group. And so to give that up to do something super risky and then put all of your savings from being in the 1% in your age group into something that the odds affect against you, it took a lot of courage and you know you kind of it takes some peanuts.
Speaker 2:It takes some peanuts, it takes some peanuts, but yeah it's a major decision.
Speaker 3:I think that what I saw, particularly when I was in private equity that was an extremely good learning experience, if not an intense grind and quite exhausting is that you see the potential in boring businesses. I was in business services, private equity so it's literally businesses that service other businesses and make money off of that, and so you see that you don't have to be on the front page of the news or having dinner with Jeff Bezos in order to make a fortune, and the people who are making the real fortunes, the real money, are the business owners, and so the founders are making fortunes, while the finance people are shifting around decimals and taking swimmers of what's actually happening.
Speaker 2:Yeah, yeah, I think that's important too, right, when people think of entrepreneurship and things like that, they think of those sexier businesses, right? Those ones that look like a lot of fun, not realizing or not understanding that, hey, when you're working behind the curtain, kind of, and working in some of these things that are not so sexy but there's a lot of opportunity and a lot of money to be made if you're willing to go that route, if you're not pursuing just the visual or the look of wealth but you just really want to grind out a business. There's plenty of those types of things. It's just maybe, because they don't look that interesting, people just discard them or choose not to pursue them.
Speaker 3:Yeah, totally, and people don't think about them. It doesn't live in a lot of people's minds that you could make the bolt on a tire on a car and get a contract and make a fortune. People think that they want to have some artificial intelligence company, but everybody's different. Some people want a coffee shop in their neighborhood. Some people want to disrupt the multi-billion dollar consumer product category. Others want to compete with Elon Musk. I don't want to compete with Jeff Bezos and Elon Musk.
Speaker 2:That sounds very challenging but I also don't want a coffee shop.
Speaker 2:Yeah, all right. And so you've got this great career and you're on the path that all of us think we want. And, yeah, you make this decision to jump into the entrepreneurship world and you come up with the idea for Gilly, which is your umbrella company and by umbrella I don't mean some seedy offshore account, we're talking about a legit, actual umbrella that protects you from the rain. Where does that idea come from? Because I think a lot of us. We get ideas in our head of what businesses we want to start. These ideas pop in our head and then we just choose not to pursue them for whatever reason. But you did so. Where did this idea pop into your head? And then, what gives you a strong enough feeling to one give up this career, where you could be making tons of money already, and actually go pursue this?
Speaker 3:I moved to go to the London Business School to London, obviously in 2019 with my wife, and I had always had it in my mind, as I mentioned before, that I was going to do something big after grad school. That's when I'd really get started, and so you know, going to and from the campus, it just organically came about that I needed an umbrella it rains about every other day, but they're too annoying to carry with you and so the simple fact of the matter is that there are few substitutes for an umbrella and if you look into it from a business perspective, well, there's been no innovation in a century. 1 billion go to the landfill annually, and you could probably name an umbrella brand now, but before we spoke and I started this, I'm not sure if you could name an umbrella brand, and that's what happened, but it was a slow drip over time. I mean, I had hundreds of conversations and when I was first thinking about this I think this would be interesting for people to hear Most everybody laughed at me because, through no fault of their own, I didn't take it in an offensive way at all.
Speaker 3:They thought I was in business school, I was going to one of the top business schools and I was working at this activist hedge fund, which is a very prestigious job, and they're just thinking wait, you're going to try to do something with umbrellas. You think you can make the best umbrella in the world. What are you talking about? And so you know, over time people stopped laughing as I got more serious. I had you know.
Speaker 3:I was fortunately in business school but it helps to talk to everybody you can to iron out the idea and so kind of over time, ironed out this idea and decided, okay, I've cut this a thousand different ways, I'm going to take the leap, what's the worst that can happen? What's the best that can happen? I think this is my path and I think I'm ready.
Speaker 2:You could lose all your money and delay earning potential for several years is all that can happen. But hey, listen.
Speaker 3:Yeah, yeah, no. And look, I thought that through, especially after giving up earning for business school, and I just thought okay, I've made a certain amount of money in my 20s. I'm going to spend all of what I have left over on umbrellas, probably, and if I lose it I don't care, because I may die tomorrow, but in all likelihood I'll probably have a lot of working years left, and so there'll be so much time to make up that money that it wouldn't matter at all, and if this works out, I'm going to make more money than I ever could in a job.
Speaker 2:Yeah, well, that's what's interesting, and I think you're hitting on an important point, which is, as we get older and I'm going to be 40 here this year yikes, and you start. You get a mortgage, you get kids, a wife or husband, so you start adding all these wonderful responsibilities, but responsibilities nonetheless. And so at least the way I think about it is, my options are limiting and limiting and limiting in the amount of risks that I can take, because I have all these things that I have to take care of, and I think a lot of people maybe have similar mentality. So I think it's really great for you to have the foresight to say like, okay, I'm still in my 20s, maybe early 30s, and it's like if this doesn't work out, I'm going to give it the old college try, I'm going to give it the best shot, but if, for some reason, it doesn't work out, you've got plenty of years to make up that money, and so that's almost like your insurance policy or safety net. Is that how you felt?
Speaker 3:Yeah, no, totally. And I was in my early 30s and I thought, okay, I'm going to spend all the money I have left over from my 20s probably on this idea, and if it flops, the worst thing that's going to happen is I'm going to go back and make a lot of money in a job and Probably not like that job. So why don't I take a stab at this? And if this does go well, then I elevate myself into a category where I'm not sitting at a desk for 18 hours a day anymore hanging on what somebody who's older than me emails me. So that sounds appetizing. To take that risk and try to get out of that situation.
Speaker 2:Yeah, and so I should probably disclose this. I should have done it earlier, but I've known Reed for a long time and so he comes to me with his ideas like, hey, you interested in investing some money to help my umbrella company come to life? And I talked to my wife about it and we said yes, and, to be honest, we live in Southern California. It really doesn't rain here that much. I don't know anything about umbrellas, like you said, but I think we didn't invest in the company, we didn't invest in the idea. We invested in Reed Jacoby.
Speaker 2:The entrepreneur and I think that that's an important thing for people to understand is we're not alone. I think, in our approach to that, it's if you're a young entrepreneur or not just an entrepreneur. Forget young, right, you're just an entrepreneur. Yeah, you can have this amazing idea, but at the end of the day, there has to be somebody with the passion to want to execute and that has the ability to execute on that idea, and I think that's like a distinguishing factor. I mean, you could probably have some crappy idea and still do, just because you're that kind of person right.
Speaker 2:And so I don't know if you could just talk to about that part about it of I think people not really like you kind of have to have it in a certain way If you want to ask people for money, which is like like we can get into that conversation too Right. But just like you're asking people for money and like man, you got to sell them on you first and the product Is that. Is that how you approach?
Speaker 3:it? Yeah, absolutely. And at an early stage it's idea and team, and then over time, some traction comes, you're able to prove it out, and your family and friends, as we talked about before, your network is your net worth, even though it's a bit of a cheesy saying and people like you and Christina who are in my life. They call them angels in the industry, people who invest in your company. But you're literal angels because you need these people to help you achieve your dreams.
Speaker 3:You don't have the money laying around, and so when people come in and back you, it means a lot. But you have to put in so much work to get to the point where you could call somebody who's not related to you and convince them to give you money in a super risky venture and that you will do the absolute best that you can to not only not lose it but to give you money in a super risky venture, and that you will do the absolute best that you can to not only not lose it but to give them back a multiple of the money that they gave to you. And that takes a lot of time. It takes a lot of work. It is very far from easy for sure, yeah.
Speaker 2:so to that end, how many people did you have to call on and talk to and just to talk about the grind of raising capital and how hard was?
Speaker 3:that it is so hard and it's ongoing, and I would never discourage somebody from being an entrepreneur. So as I talk about some of these things, I hope whoever's listening doesn't become discouraged at all, because it's the most rewarding, one of the most rewarding things you can do. I recently had a baby and so that's a bit more rewarding, but being in Australia is one of the most rewarding things you can do, but it is also it's by far the hardest thing I've ever done. There isn't even a remote second, and I think a part of that is fundraising. Where I started versus where I am now is night and day, and I've still got a long ways to go. But you have to formulate the materials. You have to formulate the materials. You have to find a list, and something I was thinking about sharing on this podcast that's really funny is when I was first making a list of people that you're going to reach out to beyond family and friends might take you one to three months just to put together a list of people to call and for them to deny it. So there's all sorts of things like that, and I would say over the last I've been working on this for over three years I probably started fundraising six months to a year into it. I have plenty of advice and insight on that, maybe for another day, but I would say you know I've reached out to at least hundreds of people. I can tell you that on this most recent round it's been 350, 400 people and it is fundraising is.
Speaker 3:It's challenging because it's mostly no's and I think that you know it can be one yes for 99 no's. You know that's something that I've heard. It's probably one yes for every 50 to 200 no's, depending on your idea and where you're at and the validation et cetera. And so when you're at fundraising you know I was doing this alone for a year and a half, two years to get started If you're at fundraising, everybody's saying no, I'm trying to create a new category of a rain umbrella. It can be mentally very challenging to say well, who's right? Is it these 99 people who told me this isn't going to work, or is it me who's spending all of my money and time on this and the jury's still out?
Speaker 2:Yeah, what are those days like when I mean that's a lot of no's. And I would imagine there were some days where you woke up and you're just like, oh God, dude, I gotta go, I gotta go call a bunch of people, get a bunch of no's. How do you? What's like the driving force behind that that keeps you fueled and going though through all that?
Speaker 3:Yeah, I think you know everybody's different. Everybody has different motivations. I think you know everybody's different. Everybody has different motivations. I think one thing that really helps me is, over time, I realized that having a community of people who are doing the same thing, preferably who have some more experience than you, is immensely valuable and keeps you sane, and so I have.
Speaker 3:For the last year year and a half out of three years I've been in an office with other consumer product companies, some from my business school others that I've met from an accelerator and being around people doing a similar thing who are going through the same kind of crises that normal people don't go through, is immensely valuable and can really help you. And then you have to have your personal motivation, because everybody's ignoring for the most part, everybody's ignoring you. Nobody cares I mean like nobody cares at all, and you and it. It means everything to you and if they care enough, they'll probably tell you now.
Speaker 2:So I'm hearing this almost sounds like a AA support group kind of deal where it's like you guys are like having to, yeah, like confide in one another. No, I mean, I get that right. Like, yeah, I could see that Like going something alone and having no one to talk to you about it, versus say, hey, man, you're not special, Like I'm going through the same thing, Like so you know, it's not you, it's the process, that kind of thing, right, and so going through that.
Speaker 2:I could see that how that's helping. Yeah, no, you, and we've talked about that. Now you've got another motivation, that being your son. How does that, I don't know, change your perspective on this journey that you're going on, if at all, or is it more or less the same?
Speaker 3:It's an interesting point. I think it changes your perspective quite a bit in that you now your two biggest issues are time and money. When you're an entrepreneur with your business, you don't have enough money to hire enough people and you don't have enough time because you don't have enough people. These problems are accentuated when you have a child, because now you really don't have enough money and now you really don't have enough time. It's accentuated from that perspective.
Speaker 3:But I think in my life this probably stems from I've kind of always wanted more for myself and I'm not talking about materials and I've always wanted to have more, explore what the world can offer me. And I think that you know as I go about that, and right now that's in the form of this umbrella company. I'm happy to kind of have him along for the ride and I hope that you know he's way too young to remember anything. So hopefully he'll kind of get a kick out of it and he'll say you know what? I can take the risk, I can lay some money on the line. I'd like to learn things and see what the world has to offer me too.
Speaker 2:Yeah, it's kind of resonating with me in the sense that I had my mom's parents, my grandparents, that were entrepreneurs. They did real estate and so growing up that was kind of always like that sounded awesome to me. And hey, I'm my own boss.
Speaker 2:I remember he would come back because my grandma would watch me a lot on the first of the month with wads of cash because this is like the 90s, before Zelle and stuff, and just like he'd lay it out on his bed and just like the smile on his face of just like this is from my empire that I built, and I'm just like this is so cool, it's so cool, right, this is what I want to do. That sounds so awesome.
Speaker 2:And so when I went to Fullerton and I finally decided to get the business degree, they had a concentration in entrepreneurship and I said, yeah, I mean, obviously right, that's what I saw. My family, that's the example I got from my family, and you talked about. This seems like a slam dunk kind of thing. And today I'm still collecting a paycheck. I'm not an entrepreneur.
Speaker 3:Well, you kind of are with the podcast.
Speaker 2:I mean typically. A business has to be making money for you to be an entrepreneur. But yeah, no, I'm kidding it kind of is, but I guess, in a roundabout way, I'm saying as a dad, which is how I look through that lens often now as I'm making decisions, is, like you said, it's like it's not about money because, like I said, I'm not making any money from this per se, but it's more so just like challenging myself to go through a process.
Speaker 2:If there's one thing I remember about growing up with my parents was like an example of working hard, putting in extra hours, like having that work ethic, and so as a parent, it's. I'm not teaching those. Maybe I need to step up my game, like you, because I'm not like in the bath giving my kids business lessons. So maybe I'm going to start doing that.
Speaker 2:So thanks for that idea, but yeah, no, I guess I feel like I'm behind now actually, so let me step it up. But no, it's like I'm not being that direct. But at the same point I'm hoping on the peripherals they are kind of seeing what I'm doing after hours and after dinner and they do come in here. I could say, if I'm online, they go to bed at 8.30 and I'm in here from 8 to 10, right, because I've got a day job. So this is all stuff happening after hours. They come in here and they say goodnight and they see me on my laptop and they see oh, what do you like? They always ask, they ask the question what are you working on, what are you doing? And I kind of implanting, I guess, little seeds in that way, and so it's just yeah, it's cool to see that you're, in a similar way, doing those sorts of things.
Speaker 2:So I feel like this kid's already way set my parents worked a lot, but my parents really or my dad really worked a lot.
Speaker 3:And so it's kind of ingrained in you and I know that there's a lot of stuff ingrained in me from watching him good or bad. So I think with my son I'm happy to have him kind of be around that and I want him to see me taking risks and kind of walking tall and being proud and I think that rubs off on them and they can gain a lot from that, even if they don't know it.
Speaker 2:What would you say to somebody that maybe was in your position deciding like hey, do I want to pursue this entrepreneurial journey? They got to be real with themselves, right. They got to ask, now that they've heard at least a bit, right For what we could get into in an hour of what it takes to really build a business. What would you say to somebody that's on the fence and what types of questions do they need to answer honestly about themselves to see if they have any sort of chance of making it successfully?
Speaker 3:Yeah, I would say oh, daddy, let it rip oh daddy but on a more serious note, I think that, whether it was getting these jobs I wanted or starting a company, the one common denominator that has gotten me this far since I left a campus in Michigan is that for each thing that I've approached, I've wanted it kind of so bad my stomach hurts and I've had an incredibly high pain tolerance, and so if I stub my toe on the wall I might scream. But professionally I can do a lot of toe stubbing and not cry, and so I would pick an opportunity that's right for you. Not everybody wants to have an artificial intelligence company and raise $6 billion, and not everybody's equipped to do that right away. Maybe that could be a third or fourth company, maybe it's just not right for you. Maybe you want to have a coffee shop in your neighborhood, find something that's right for you and then set out some timelines and just know it's going to take a lot longer and it's going to cost a lot more money than you want it to. But everybody's different, and so you can work on it at night if you want.
Speaker 3:For me that wasn't going to work, so I dove in full time and I said I'm going to spend all of my money, if I have to on this, the decisions made. I'm doing it, Other people, you know it may not be that intense, and so you have to find the opportunity that's right for you. It has to be at the right time in your life, but at the same time, don't overthink it, like nothing's ever going to line up perfectly and you'll find, once you really get started, that everything goes wrong all the time. So do the best you can with that decision making, but then just leap in and start taking the hits and I think it'll be one of the most rewarding things you ever do, and hopefully you don't fail, hopefully you make a lot of money out of it.
Speaker 2:I think you're right and I think we're good examples of that. So you're the example of diving in the deep end headfirst and just going that route. And I'm the opposite. I'm hey, nope, I've got a family, I've got a full-time job. That's my focus from nine to five, but I can dabble in this on the side. And so, yeah, I guess for people out there, right, it's like figure out what journey works for you. And then the other thing that I heard from you is maybe think about in your head like what is the worst possible day of your entrepreneurship journey, look like, and then ask yourself, like can you get through three straight weeks of that and still have that grind mentality? Or are you like, oh man, and when I hit those road bumps I'm going to really think twice about it? Right, you can't do that. You just kind of got to go for it right?
Speaker 3:Yeah, totally. And one thing to think about is I'm the personality type where I burn the boats, I burn the ships that old saying where they drop the soldiers on the beach and they'd say those ships are gone. There's only one way through, and so I did that. And so these extremely painful moments. I don't have much of a choice. I'm in too deep, and I know it. If I were somebody thinking about it, I would burn those boats because there's going to be Ooh, no way.
Speaker 2:I'm keeping a rowboat, I'm keeping the yacht, I'm keeping all of it, keeping that motorboat.
Speaker 3:I'm keeping that motorboat, baby. Yes, 100% yeah. I guess everybody's different, but I would-.
Speaker 2:But to your point, you got to know your personality. I think is what you're saying right. For you you had to burn the boats because otherwise maybe you would have got distracted or you would have given up on it and, like I said, for me it was like no, I'm disciplined enough to where I can put aside these two hours a day or whatever it takes, and still be like and keep motivated and stay on that path.
Speaker 3:Right, yeah, totally Right. Like you said, everyone's different, everybody's different, everybody's different. But you can handle a lot more than you think if you want to. Let me put it that way.
Speaker 1:If you want to, if you want to, that's the key.
Speaker 3:If you don't, I'd avoid entrepreneurship if you don't think you want to, but if you do, give it a whirl.
Speaker 2:All right. So this reach out to you to want to talk to you was partially because I was driving Adrian home, my oldest son from baseball practice, and he talked about like how do you build a company and how do you do that? I'm like, well, let's go. Let's go talk to Reed because he'll tell us all about it. Now, before we go, he has one big question for you, big question for you, and that is he just in that car ride, has decided that he's going to start a robot manufacturing company. It's called Adrian's Robots and so, just to take on any critiques you have on the name or just the idea in general, how are we feeling about it?
Speaker 3:I love it. I think robotics is hot right now. You can see it in the headlines.
Speaker 2:He knows the trend. He knows the trend. I don't know.
Speaker 3:I didn't tell him that he definitely knows the trend and I think, going into umbrellas, there aren't many other people doing it, but if you go into robotics, there are other people doing it and there's comfort in numbers, and so he'll be able to raise more money and he'll have more confidence in the idea. I think.
Speaker 3:From a name perspective, I love it because people know what it is, which is really important If you think about like Yeti coolers cold, although, I would just caution him that 70% of the English language is trademarked at this point, so he'll have to get a pretty good lawyer and I know one to help him to trademark that.
Speaker 2:All right, we'll let him know. Reid, it's been awesome man, so excited for you and what you're doing, and I know you're going to make it happen Before you know it all you guys listening and everyone around the world you're going to have your Gilly umbrella on hand at all times. Thanks Paul, Thanks Reed and good luck for the rest of the journey, man.
Speaker 1:The Rockies ain't too far from here. If we drive all night, the cold, that will do you well in the mountain morning light. So let's ride, let's ride on through the rain. Come on and take me anywhere that you want to be. Let's ride and let's ride. Let's follow the skyline and when we make it to the other side We'll find all the bluest skies.