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Nick Carey
In a lot of ways, I go to teachers because I want to learn something, but I think with a mentor, it's almost more like I want to discover something about myself. And that requires to have a relationship where there's a lot of vulnerability. And also, as Beau mentioned, you generally want to be getting mentored, I think, by someone that you have a lot of respect for. And you can go look at the wide world and there are all these different celebrities and influencers and people in high rank roles. But when you peel back, you know, the marketing and the image, like, what do they stand for? How do they behave when people aren't looking, you know, what are their morals and values? What kind of legacy are they leaving? And there was a book I read a while back that really touched me, which is like, everyone's chasing all these resume virtues all the time. You know, they increased their, you know, KPIs by 50% this year and it's the kind of stuff you broadcast on LinkedIn. But at the end of the day, what's put on your, you know, gravestone is really a lot more and speaks more to the quality of your character.
Kevin Gentry
Welcome to the Going Big Podcast. I'm your host, Kevin Gentry, and this is the place where we celebrate bold moves and big ideas. Each week I sit down with inspiring leaders, entrepreneurs and change makers who are making a significant impact in their careers and in their communities. Whether you're looking to level up your leadership, pursue your passion, or just get inspired to take your next big leap, this is where those stories come to life. Now, if you're listening on iTunes, YouTube or anywhere else you tune into podcasts, be sure to hit that subscribe button so you'll never miss an episode. Now let's dive in to what it
means to truly go big. Well, ladies and gentlemen, welcome back to another episode of the Going Big Podcast. I'm your host, Kevin Gentry and I'm pleased to have as my guest today Nick Carey and Bo Ghirardelli. These two guys took a swing together at something that is truly impressive. And what they've turned it into is I think it'll be of great interest to you for the conversation today. They have enabled a platform which has enabled hundreds of thousands of would be entrepreneurs to access educational material, coaching and mentoring and capital resources to overcome many obstacles that would be entrepreneurs face today. They had this idea related to leadership and mentorship and training, but they didn't just talk about it. They took it to a scale by tapping technology. And as you're about to see, they have the ability to really, in my judgment, transform so much about what we see today in the marketplace. So, Bo and Nick, it's a real pleasure to have you all. Thanks for joining us.
Bo Ghirardelli
Thanks, Kevin.
Kevin Gentry
All right, Bo, I'm going to lead off with you and from time to time I'll go back and forth. But when somebody asks you, what is this organization that you've started, Sky's the Limit? What is Sky's the Limit? How do you describe it in a quick elevator ride to somebody who asks you, sure.
Bo Ghirardelli
Sky's the Limit's a digital success platform for low income, earliest stage entrepreneurs, connecting them with education, networks and capital.
Kevin Gentry
Well, what is the problem that you saw that you're working to solve? Bo, I'll let you go first and then Nick, you pile on. I mean, is there a problem? What are, what's holding people back from starting a business today?
Bo Ghirardelli
Yeah. So I'll tell you a little bit about how we got started and illustrate this as a story. And when I was in living in Morocco during the Arab Spring as part of the Peace Corps, in the first month of living in a small community of about 15,000 people, I was approached by over a dozen adults who said that they had business ideas but didn't know how to get started. This was particularly relevant because we're in the midst of the Arab Spring, which, as you may remember, was a period of intense, intensely high unemployment rates. And so folks were turning to entrepreneurship out of necessity. And what it illustrated to me was that in my community there wasn't a good place for folks to turn to, to learn about how to start a business. So I worked with this initial group on creating a plan for how they would launch their business idea. And all of these ideas played to their strengths. So one woman had grown up in a family full of sheep farmers, and so she was going to build a herd herself. Another guy grew up in a, in a, in a family who owned fruit orchards. And, and so he knew how to pick and harvest fruit and sell it. And so he was building a, a resale company for that. All of the, all, all of these folks had some talent. And what they didn't have was a, a way to channel that into creating a living for themselves. So after they, they, and this, this, I can tell you much more about that story. We can come back to it if you'd like, Kevin. But at the end of the day that millions and millions of people across the world who have talent but don't know how to channel it into building a business, and that's what Sky's the Limit can do is help you build a company around your talents.
Kevin Gentry
All right, well, I do want to dig in more to understanding the problem. You and I, the three of us, have worked together now, known each other for about six months, but I'm still a newbie. I'm really trying to understand exactly how you all are taking this stuff to scale in the consequential way that you are. It's a phenomenal thing, but still to really understand this. Nick Carey, what was the aha moment for you? You weren't there as a Peace Corps volunteer in the Arab Spring. What was that aha moment for you?
Nick Carey
Well, it's been a pleasure watching the early founding of this entity with Bo and hearing his stories from Morocco were deeply troubling. You had all this social unrest, extremely high levels of unemployment. People were losing faith and optimism in their society, and it was having colossal perturbances, not just in their own country, but actually through the whole region. And when he came back to the United States, we started talking, and it was pretty obvious that actually, just even in our own communities across the United states and all 50 states, there are tens of millions of young adult entrepreneurs that have ideas but don't know where to turn to. And this problem is actually really huge. Our bulge banks, the systemically important financial institutions, define a small business as nearly something having a million dollars of turnover or more. And actually the vast majority of businesses, first of all, they start off with a lot less than that, and they may never all get there, but there's actually this whole category of successful, thriving small businesses, and everyone has ambitions to maybe make them quite a bit bigger. But that earliest gap is where all the vulnerability is. And so many of these early stage entrepreneurs are lacking know how, lacking community and support and finally access to capital. And it's actually, it is a huge social problem. It is a massive economic problem. And it's leading to this sort of malaise, I think, that we're all sort of hearing a little bit more about, which is that people are sort of feeling like the American dream isn't really there for everybody anymore. And this is, even, according to research, the first generation in the history of America where parents are saying the opportunities for their children aren't as good as they were for them. And a big factor in that is there's a confusion about what kind of jobs are gonna exist in the future and where people can turn to. And so the scale of this challenge is immense and it requires novel thinking. It requires a 10x solution, if not a hundred X. So we'll have to rebrand this podcast in a decade, Kevin, but we got a lot of work to do between now and then. But at the end of the day, you know, people are losing faith, I think, in their ability to succeed on their own merits. And we want to intervene right there at the earliest stages of their entrepreneurial journeys to be partners with them, to be support for them, and ultimately to help them achieve their potential. And so we hear a lot about economic disparities. United States, there is poverty. Half of households in the country don't have $1,000 to their names and savings. But it's not always for a lack of effort. And we exist to basically support those that want to do something about it.
Kevin Gentry
Well, okay, thank you, Nick. And I wanted to even unpack more the consequences of that problem. You know, I heard a statistic yesterday that 90% of new businesses don't survive after a couple years. But, okay, that's the free enterprise system. That's creative destruction. These things have happened for a long period of time. But you're arguing there's something else going on there. So tell me more about the consequences of losing faith in the American dream. There are surveys now that show that many people don't believe they can enjoy the same kind of livelihood that their parents did. This is one of the first things that we've ever seen in this country because people always felt like they could do better than the generation before them. But what happens when people lose hope, in your judgment?
Nick Carey
I mean, bo's witnessed it with a firsthand experience during the Arab Spring across the Middle east, where you had total social unrest that really begins at first because you have a large unemployed population. And when people are bored and unemployed and desperate, you get very terrible outcomes. But even if things aren't working very well, you also get a lot of dependencies. And worse, you get people that don't fulfill their potential, don't create the next innovations, don't invest, don't teach their children practical skills, financial literacy, and more. This has health consequences. It costs Medicare and Medicaid an uncalculable amount of money to have people that are unproductive and not working. And so this is a really challenging and complicated problem and one that requires a very large scale of intervention in order to head off. And so we've seen what happens in societies and in political systems when you have a large number of youth unemployment. And I think there's a big question mark, you know, in a big freight train headed to the American economy right now, which is what's going to happen with all the labor dislocation related to artificial intelligence. And this is a question economists are really struggling to answer. It's a question that's been very awkward for tech CEOs to face off against. And, you know, I think there's going to be some reckoning around all this over the next few years. And, you know, we're really focused on addressing that because we still see entrepreneurship is a very viable pathway for not only people that are looking for jobs, but people that are maybe going to be disrupted in their careers because of all the changes that artificial intelligence is going to bring by automating many jobs away. So that's a bit of the atmospherics
Kevin Gentry
to set some stage. You've brought it to life. I mean, I think we all feel a growing anxiety around the consequences and disruptions from artificial intelligence. We want to believe in just the creative destruction will lead to the next best thing. But there's so much uncertainty, uncertainty. And then when you pair that with these other obstacles that people face today, it is considerable. All right, but how did this idea happen? You all were roommates, is my understanding. How did you kick around this idea to the degree to which you said, okay, a, something has to be done, and B, we're going to do it through a group called Sky's the Limit, and we're going to do it through this online platform. How did this, how did this come about?
Bo Ghirardelli
Yeah, well, I mean, I think there's. I think, you know, good friends help you pressure test ideas, and they help you evolve your own thinking through. Through conversations. So there was a lot of that in the early days, I think, you know, working with Nick in our fraternity when he was the president and I was the philanthropy chair, really saw like a lot of common ground there and a belief in living for something more than ourselves. This idea that of contributing to society beyond our own personal enrichification was something worth pursuing. And I think there are a lot of Americans feel the same way about that. And that's what really helps us build solutions to market failures and philanthropy. But Nick has been an incredible partner along the ride. I mean, this guy has spent his career building tech companies. And when I approached him around Sky's the Limit, he was in the midst of building what is now a unicorn tech startup called Blockchain.com and this guy took on an incredible amount of work with Sky's the Limit to get it off the ground while he was getting blockchain.com off the ground. And I will. It always boggles my mind how he pulled it off. But Nick's a true believer in what we're doing and the opportunity for all of us when we unlock the potential earliest stage low income entrepreneurs across the country and the globe.
Kevin Gentry
Well, you've certainly tapped into something that makes this conversation all the more interesting. And that's obviously Nick's background and co founding Blockchain.com and the whole space and cryptocurrency and technology and just your trailblazer, Nick. So I don't know how you find time to also be engaged in a nonprofit, but I want to understand a little bit more about Joel's backgrounds. This always comes up. People want to know more. So we'll start with you, Nick. My understanding is you've lived all over the world, you've spent a lot of time in England. What, what influence, what was shaping your view of the world that got you to the point where you are today?
Nick Carey
Yeah. Thanks, Kevin. It's always kind of fun to go down memory lane a little bit. I was raised predominantly by a single mom and I had jobs basically as soon as I can basically remember. But I think one of the cool things is we actually all start off as entrepreneurs. And this is one of the tenets of the book Bo and I wrote as well called Building Businesses Together. But I love asking this. It's how did you earn your first buck? And you can ask anybody that question and they'll usually say, I started a lemonade stand. I took the groceries out, you know, got the groceries from my grandparents, I mowed the lawn. You know, maybe sometimes things got a little more sophisticated. And so interestingly, almost everybody has some kind of relationship with entrepreneurship and then, you know, maybe it goes off the rails at some point. But my first job, I collected clams out of the Long Island Sound and I had them in a dive bag and I made a sign. And I used to sell cherry stones and chowder clams and little necks, and I would bike them over to my neighbors. And I always had a funny price, like, you know, 675 or something. And of course no one ever had correct change, so I would always get extra. And so I learned some random little things as a young entrepreneur. Everything from inventory management to marketing to just in time delivery. And then one of my mean neighbors, this old lady, actually sent the fish and wildlife people after me because I didn't have a permit of course, as a 13 year old kid to do any of this. And she became like a pariah in the neighborhood. But Also eventually they came over and they showed me how to fill out the application and they were really quite generous with teaching me. That was not the first time I would run into some regulatory challenges in my businesses, but it was a good early lesson. But I mainly think that like I took some of those lessons, you know, went to university where I met beautiful, literally fresh first day on campus. I used to build websites. I was the tech guy for the foreign language department and then graduated with a fairly significant amount of student loan debt. And I was convinced that, you know, I thought I should go work for one of these big tech companies. And frankly, through the interview process, I just, it felt so foreign and alien to me. And I, you know, I asked him once, I remember I said, if I outperform and I achieve all the things that, you know, you've asked me to do, what happens? Then they go, well, you know, next year there'll be a new set of things that you can work toward accomplishing and if you get through all these ladder rows, you know, you'll have some outcome for that. And I didn't think at the time that didn't make sense to me and it still doesn't make sense to me. I wanted the merits of my work to speak for themselves. And so I ended up pursuing a full time career in entrepreneurship. And the first business I got invited to participate in was called Pipeline CRM. It's a customer relationship management software. It was an amazing experience. I was 21 years old when I started working there. I didn't really know that much about anything, but I was hungry to learn and I had a lot of energy and effort to toss at that. And what was amazing is just like you interview all kinds of people and learn a lot from them. I was interviewing all the CEOs of these companies and they were telling me their most important secret, which is how they make money. And so I was learning about the sales process of all these different companies while getting them to try and use our CRM product. And so after that, you know, the, the opportunity came to basically go found with my British business partner, Blockchain.com which was a very early pioneer in the digital asset in cryptocurrency world. We've been at this now for 15 years. We're one of the oldest and longest standing companies in the business. And I'm really proud of all the work that we've done there. And so that's been a hell of a journey too. But one of the things that personally motivates me and I'll wrap this up quickly here, but I really have two levers that matter in my life. And one is that I feel like I'm learning a lot, and the work I get to do@blockchain.com continues to be very intellectually interesting. And the other is that I need to feel influential. I want to feel like I can participate in a way that matters. And there are two big problems, as I see it, in the world today. One is that money is quite broken. It is created, frankly, out of thin air. It grows in quantity every single year through fractional reserve banking. Inflation is growing, and we have to pay for things in a currency that is constantly devaluing. And so I'm very interested in alternative financial systems, ones that are built on sound economics and foundational monetary systems that have more consistent supply and demand concepts in them. So this isn't a podcast for cryptocurrency, so I'll stop at that there. But the other thing that I care a lot about is entrepreneurship. And the reason for that is I believe it to be an extraordinary empowering mechanism for people's personal agency, a way to learn, a way for them to pass skills and wealth down to their friends and family and their communities. And frankly, we need a lot more entrepreneurs in the world, and we need a lot more entrepreneurs that look like the composition of our society. So that's young entrepreneurs, it's entrepreneurs from diverse backgrounds, it's women entrepreneurs, it's immigrant entrepreneurs, who, by the way, tend to do very, very well as entrepreneurs, partially because it's a necessity for them to be successful. They have extra sort of wells of motivation in some cases. And by having a society that is feeling optimistic and prosperous and growing, this creates a bigger pie for all of us. And it helps abate those big concerns we have about social dislocations, political dislocations, and all the consequences of a society where people don't feel optimistic. And so the engine of all of that prosperity really starts with entrepreneurs. We worry a lot about jobs and how many jobs are being created. But all those jobs have to be in a company, and that company has to be started by. By somebody or a group of people. And so those are the two things that I care a lot about. I care so much about this problem, Kevin, that I've pledged over half of my shares from blockchain.com to working on solving this challenge in perpetuity. And I have chosen to work with beau for over 15 years to work on this problem set. And the last thing I'll say is It. I think it's amazing that people dedicate a lot of time and money to volunteering and philanthropy. And one of the things I try and encourage people to do is to practice doing that earlier. Just like any muscle, if you don't exercise it, it atrophies. And I don't think it's sufficient to become generous just at the end of your life. You need to be pulling that forward. We got a lot of big challenges in the world today, and we need individuals to start to step up a little bit more. Can't count on csr, can't count on Washington. You know, we gotta count on each other, our neighbors, and our citizens in order to do that.
Kevin Gentry
Amazing. Well, Nick, thank you very much. As the audience can quickly comprehend, you have your own going big story, just with respect to the trails you're blazing in the cryptocurrency Space and with blockchain.com, but it is so inspiring that how you have dedicated your life now, though, to giving these entrepreneurship opportunities to others, which I really want to unpack. And that's why I really wanted to have you all on the Going Big podcast. So that means I turn now back.
Nick Carey
We're just getting started, Kevin.
Kevin Gentry
Yeah, exactly. No, I know the enthusiasm that you all have is always infectious. Bo, you grew up in Oakland and went to public schools there. You were interested in entrepreneurship, supported some programs there. How did that influence your perspective on entrepreneurship? We heard how Nick's life has influenced him. How about you?
Bo Ghirardelli
Yeah, I mean, I grew up in a family full of entrepreneurs, a multi generational entrepreneurship family. Unfortunately, we don't still own the chocolate factory, in case you were going to ask that. Otherwise, we be giving that money away through Sky's the Limit. But, yeah, just growing up and seeing that path and talking about entrepreneurship at the dinner table was a really different experience that I had that would have been. I didn't realize how rare it was until I was older and realized that most people didn't talk about how to sell or how to hone your product to fit what the customer wants. And so that upbringing, and one that was also really focused on living for something greater than yourself. And so purpose was a big deal to me as a kid. And so Sky's the Limit is an amalgamation of the two. It's a passion for entrepreneurship. It's my tribe, it's my people, and I love them. And when I see groups of entrepreneurs being ignored, it's such a reason to wake up and do this work every day over and over for 15 years now. And I think when you look at the problems that society faces, whether it's in education. I was an educator with Teach for America in South Central Los Angeles for two years, whether it's in Morocco, where I was living in Peace Corps and working in rural communities, there is so much talent across the world, but there are huge intractable problems. Health, education, and ultimately poverty. And the relationship between economics and all these other problems is so strong. So when you have entrepreneurs and you empower entrepreneurs to build, they're an incredible route to solving the problems that touch every sector of our society. And that's what really keeps me motivated on supporting this group. And it's a big part of my. Why.
Kevin Gentry
All right, well, plenty more to dig into, but you can't just mention a chocolate company in passing with a name like Ghirardelli and just expect us not to take notice. Tell us a little bit about the history that you referenced there.
Nick Carey
I'll just say one thing about that before he goes on this tangent. There was a rumor, Kevin, the first couple days on our college campus that Willy Wonka's heir to the Ghirardelli empire had arrived and it was like a wildfire. But anyway, now he can tell the story because it's relevant.
Bo Ghirardelli
Yeah. Well, if you, if you've heard that expression, wealth doesn't last past three generations, that's, that's, that's our story. So, yeah, great great uncle, triple great uncle, started the, started as an immigrant entrepreneur, came over during the gold rush.
Kevin Gentry
He came from South America, didn't he?
Bo Ghirardelli
Did. He came from Italy via South America from the cocoa fields there. And he came to California to try and. Try and make it rich during the gold rush and brought 50 pounds of chocolate along with them and, and, and totally failed at gold mining, but started selling that chocolate and, and turned out he made a fortune doing that and called home and said, hey, or really sent. Sent a note home a long way to, to get some more. And that's, that's the birth of it. So unfortunately, he, he sold that company
Kevin Gentry
in his own, like 1960s or so, didn't it? The, the Rice of Roni, they hold all the different other stuff in San Francisco, right?
Bo Ghirardelli
Yeah. The 1850s. Yeah. Yeah. So by, by before the 1900s, he'd sold it and, and.
Kevin Gentry
Oh, okay.
Bo Ghirardelli
Yeah. So now it's, you know, a Nestle brand or whatever. Yeah, but, but yeah, they so grew up, you know, tales of, of people making it big. But also it's a, it's a good reminder that, you know, you need to understand how to manage, manage wealth as you make it and, and what you choose to do with it. You know, this guy spent it on himself instead of on causes, you know, bigger than himself. And, and I think that that's, you know, I think a really missed opportunity. And I think it's important, as Nick says, to think about what you can do with your money today to solve problems that exist today instead of waiting for some future date.
Kevin Gentry
Okay, so I want to now understand the solution that you all come up with to the problem that you've identified and how Sky's the Limit came out of that. So you've, let's say you've persuaded everybody listening that the failures in our entrepreneurial system today with respect to the obstacles that are in place and those obstacles, everything from not enough knowledge and experience to lack of role models, lack of capital. What, what, how did you come up with this solution called Sky's the Limit? And what are you trying to do with this as the solution?
Bo Ghirardelli
Yeah, well, so this is, this is part of, you know, as Nick mentioned, we realized that the same problem we were solving in Morocco exists in our, in our cities across America. And in 2015, we had over 5,000 applicants to our Oakland based program. And this was, I think, a big part of why Nick, if I'm not speaking out of turn for him, but a big part of why he was like, okay, look, we can do something about this. I said, obviously we can't serve 5,000 people across the country from this brick and mortar operation in Oakland. We need technology to solve this problem. And I think that's where his technologist lens has been really invaluable, is helping us chart a path to solving problems for entrepreneurs, no matter where they live, and then doing so efficiently and flexibly in a first century manner of serving an entrepreneur, which is also a missing piece in the nonprofit ecosystem.
Kevin Gentry
All right, well, Nick, what is the solution? I want to follow up by asking how you applied the lessons from scaling blockchain.com into scaling Sky's the Limit. But what, what are you specifically offering to a would be entrepreneur that they don't otherwise have access to?
Nick Carey
Right. So a lot of people use like the model of, you know, sort of like a place based program where you go to a building, you fill out an application, you wait for the school year to open, you maybe get some coaching and you have some homework and, you know, you might have some peer interactions and then maybe an expert or two comes along and there's a test at the end and you get some kind of certificate. And that's sort of the, like, education model that's applied, especially like business schools. And that's where people learn how to maybe manage a job as opposed to create one and become an entrepreneur. So there is no university for entrepreneurship. The only way to go learn it is to go practice it in the wild, in the real world. And so what we learned when we opened up shop to set up a place where people could come practice entrepreneurship with the primary belief that anyone can learn this skill and get better at it by practicing, like Beau mentioned, we had people sign up from all across the country. And so immediately we knew we had a lot of demand for this idea and we hadn't even really marketed this yet before. And so we had to go through a transformation and become a digital technology or digital charity. And in doing so, we were able to take all the lessons of things we knew worked, graph them onto a technology experience. And then now we've been able to scale this to a level that can support every aspiring entrepreneur across the United States and soon anywhere in the world. And so we've had some amazing partners in this work, by the way. So I don't want to take any or all the credit for this whatsoever. We approached one of our key anchor funders very early on who understood this challenge and who also saw the opportunity to do something really impactful at a very big scale. And a lot of credit is due to our partners at Accenture who have been with us riding side by side, helping us deliver against these ambitions from the very early days. And so with that, we got sort of this transformational confidence and partner in place early on. And then, you know, my work in the technology space, informed by building and supporting many successful businesses, hopefully has helped us shape how to think about delivering high quality experiences at scale. And so what we do, we very basically is that anyone in the world can sign up for Sky's the Limit. You Visit Sky's the limit.org and we're really looking for two different types of people out there. One are entrepreneurs. And so if you've got a business idea, you're practicing building a business, you don't know where to start, or even if you're further along and you've maybe lost some motivation, we're here for you. You can sign up, you create a profile on our app, you can download that for free from iOS or Android, or use your laptop to sign up, and that'll get you enrolled in our community. It's a ongoing, forever enrollment. We don't have seasons, we don't have semesters. You can sign up at 2 o' clock in the morning. You can start building your profile on your ride to work on the subway. And you can basically use this flexibly. We're also recruiting Kevin volunteers. This is a key aspect of our intervention. We work with our corporate partners, like folks at Accenture, like folks at Wells Fargo and Bank of America and, and Goldman Sachs and PNC bank, who have all contributed thousands and thousands of volunteers to the Sky's Limit experience. This is a key aspect of our community. So everyone can sign up for free and then they're enrolled in the Sky's Limit experience. The first part our entrepreneurs basically spend time with is a product offer we have called missions. This is a little bit like, think of it like task based activities that you would go do in like a video game. So you tell us who you are, what your idea is, why you're personally motivated to do it. You describe your customer, what are their preferences, what are their price points, what are the problems they're experiencing that you're trying to solve. And we have all of these modules that are Based on over 15 years of experience and working with tens of thousands of entrepreneurs on a bilateral basis that have informed this curriculum. And that's the entrepreneurial education bit. We can match our entrepreneurs with all these subject matter experts and mentors that have been recruited by our corporate partners. And then the last thing we offer is access to capital via very novel funding system. So entrepreneurs can create pitches just like you see on television with Mark Cuban and the guys that are always on TV getting pitched all these different things. Practicing, talking about your business is a key skill that all entrepreneurs need to learn. And we have a program that lets them create a pitch and even win grants to help them grow their businesses when they're ready to do so. So all put together, the Sky's Limit experience helps entrepreneurs learn, helps entrepreneurs get access to social capital, which is this key element. Support from peers and volunteer mentors and advisors that we recruit to Sky's the Limit. And then the last piece is access to capital that we provide through our grant making vehicle.
Kevin Gentry
All right, wow. Okay, so I think we can all understand the educational component. Good for you for providing this at scale. The capital component makes sense. You're filling a gap in the marketplace because most banks see that as too risky or too small of an investment to make. Because you're probably making. It's a pretty modest bit of capital that you're offering. My guess is, but on the mentorship the coaching standpoint, fascinating. What experiences did you each have in your own life with mentorship that influenced your thinking about how to offer this? With this? Bo, you go first.
Bo Ghirardelli
Yeah. I think mentors have been incredibly important all along the journey. Even before I knew what the heck a mentor even was. Right. I'm talking about grandpa, who had an advertising company just showing me his. How he advertises for his clients and. And helping me understand that. That his job was to help them get more customers and to help their brand get discovered by more people. And I was tremendously influential. And, you know, I really looked up to him as a role model. And so it always helps when you. You respect the person, you listen a lot harder to them. So learned a lot from him. And then there's been folks along the way. Some of them are board members. Guy Fabiotti, who helped merge Elance and Odess in the early days of the Internet economy to help people around the world find work. And now this company looks like Upwork, which is a huge publicly traded company. And Fabio has just been an incredible source of inspiration and mentorship to me along the way and shares a lot of the same values and dreams for this work. And he found us online. We waved a flag and said, hey, we're looking for advisory board members. And he reached out and what a fortuitous encounter. Sometimes you just got to put yourself out there and things happen, magic happens, but you gotta work for it, and you gotta. To be okay with. With a lot of failed attempts. And I think that's. That's part of the journey of finding a mentor is. Is making sure that it's a. It's a good fit for both of you. The timing has to be right and. And. And I think that it goes through seasons as well, and you need to. You need to be able to ride with that. With the. The changing of the times.
Kevin Gentry
Nick, mentorship comes up a lot in these. Going big conversations and gotten all kinds of advice about how be a mentor, how they can seek a mentor, how they can learn from a mentor in your judgment is. So we have teachers. Teachers are more formally constructed in schools and things. We see that very clear role. Mentor is somebody that's practicing something we want to do and we can learn from informally. How would you describe that and how have mentors been important to you?
Nick Carey
Yeah, I was just thinking about that while you two were talking, because in a lot of ways, I go to teachers because I want to learn something, but I think with a mentor, it's almost more like I want to discover something about myself. And that requires to have a relationship where there's a lot of vulnerability. And also, as Beau mentioned, you generally want to be getting mentored, I think, by someone that you have a lot of respect for. And you can go look at the wide world and there are all these different celebrities and influencers and, you know, people in high roles. But when you peel back, you know, the marketing and the image, like, what do they stand for? How do they behave when people aren't looking, you know, what are their morals and values? What kind of legacy are they leaving? And there was a book I read a while back that really touched me, which was like, everyone's chasing all these resume virtues all the time. You know, they increase their KPIs by 50% this year, and it's the kind of stuff you broadcast on LinkedIn. But at the end of the day, what's put on your gravestone is really a lot more and speaks more to the quality of your character. And so being a man of good character, I still think we have a kind of lack of good leadership in the world today. And finding mentors that can help you navigate the complexity of your anxieties, your imposter syndrome, regulatory challenges and more is not always easy. But a lot of people are also willing and really eager to share some perspectives and help you figure your own out. And those are the best kind of mentors. And I've been so lucky in my career to have some amazing people that have helped me see around corners, helped me see my own challenges and put a mirror up to my. My own comments and statements and. And ultimately a bit hold me accountable. And, you know, it's not just about having someone there, you know, hitting you with a stick, telling you to work a little bit harder. You know, it's about, you know, getting deeper about what your personal motivations are for doing something. And so my advice is to try and find mentors, if you can. We offer this at Sky's the Limit because we think it's so foundational to helping people, you know, navigate the complexities, stresses, challenges of building a business. And, yeah, I think it's also an amazing way for people to give back. We interviewed Richard Branson a while back, and he speaks so fondly of mentorship. He says it helps keep me young and it helps me revisit, you know, my history with my own work. And I've got new reflections on that stuff. And I think about that, and it's quite a wise thing in my view. You know, older people have Been trying to tell us lots of things for a long time. And usually when we're young and full of adrenaline, we're not always ready to hear them yet, but sometimes those moments click and it really does unlock profound moments of clarity.
Kevin Gentry
Well, frankly, I think we're sold on the benefit of mentors. We're all struggling to find out how exactly to tap their wisdom. But how in the world do you all do that at scale through Sky's the Limit. How do you connect an aspiring entrepreneur and a would be mentor together?
Bo Ghirardelli
Yeah, well, and we have, we're still on a learning journey about this. I think that the idea is that finding the right person at the right time is the problem to solve and there are a lot of ways to solve it. One of the things we learned was that getting people into group events where there was a context for the event, like, oh, we're going to do pitch coaching or we're going to do group mentoring on digital marketing, for example. And so then this brings people in and we know what we're going to talk about. We have the ability to, on a, you know, do zoom breakout rooms so you can go from a larger group down to a smaller group and then you start to meet people. And in these, in these virtual events are where we see a lot of our mentoring relationships start. So that's one route and then the second place that they, that they happen is on our platform. So you can use our recommendation algorithm to help you find mentors and advisors and you can decide for yourself after looking at their profile what they had to say about themselves, whether or not this feels like somebody you want to reach out to. And then you can message them directly on our, on our platform. But a lot of times we find, you know, come to an event, meet some people, have an informal conversation, find common ground and then you can, and then you can keep that, that mentoring relationship going. Whether you're able to meet in person because you somehow are in the same city or whether it's over, over zoom or the phone.
Kevin Gentry
Nick, I want to take something back to you because you've spoken out about your thinking on leadership, about persistence and resilience and long term thinking from your experiences. How does that influence the kind of advice you recommend for these aspiring entrepreneurs?
Nick Carey
It's a good question. I do think it's very personalized. I think a good mentor has to ask a lot of questions. You're not really there to be prescriptive or to tell people what to do or what not to do. It's to help Them process and understand a perspective or an anxiety or a challenge they're experiencing. Now, sometimes you can teach a lesson or a moment from your own lived experience that could be quite valuable to them. It's not to say that they're experiencing it the same way, but you know, you could say, well, we don't touch the stove because it will burn you. And if you take this much risk on, there are big consequences. So make sure you consider a risk adjusted approach to X, Y and Z in your business or in your personal life. But yeah, I think the, you know, a lot of founders talk about the journey being very challenging or lonely or difficult. And I think that's sometimes true. But it doesn't have to be. It can frequently start off that way though, as you feel like you're the only person in the world that cares as much about the problem you're trying to solve. And Sky's limits here for those entrepreneurs, we want to be that support system, be your best cheerleader, help you find peers, help you find people that are rooting for you and ultimately help you find customers, product market fit and build a successful, sustainable business. And it doesn't have to be a unicorn company. There's so many measures of success, between zero and a million of revenue that are very worthy and admirable businesses. I have nothing but respect for anyone out there building a company because it is just so hard. And that's one of the things, you know, a billionaire founder will tell you and a small business owner of a bodega around the corner. Being in business is not easy. It requires persistence. And I like to describe it as almost the business code of ethics, which is doctors talk about how you have to have a do no harm principle, the Hippocratic oath. And I think in business, you know, there's sort of a always take care of your customer and take care of your customer first. They're your best teachers and they'll reward you. And having a long term perspective on that helps build really enduring, loyal customer bases which are really valuable over the duration of time. So there are nuances to all of that, but, you know, those are some views.
Kevin Gentry
Well, here, here. That's some good, sound advice. All right, we'll talk about shared life experiences. Bo, bring this to life a little bit. Nothing beats a good story. Do you have in mind a story or two about one of the aspiring entrepreneurs that Sky's the Limit has helped? Yeah.
Bo Ghirardelli
I can tell you about a woman who inspires me. Her name's Brianna and she's on our board of directors and met Brianna a while back out in the Bay Area. And she grew up in a family where her mom had started a popcorn company using family recipes. And this is. This is gourmet popcorn. It's delicious stuff. And the, you know, as she grew up and worked in that business, for her, for her mom as a kid, right, Bagging popcorn, et cetera. So this was part of her upbringing. Unfortunately, you know, later in life, as a teenager, she was trafficked and this changed her life, this tragedy. And as she entered the workforce and was trying to figure out what she wanted to do with her life, she realized that what would bring her great joy and purpose would be to resurrect her mom's popcorn company. And so it's called Katrina's Popcorn in honor of her mother. And this gourmet popcorn company has a very strong mission. So Brianna. Brianna's goal was to create a place for women to work who'd been trafficked and give them a place to heal and earn money while they were on that journey. And so she's provided dozens and dozens of women an opportunity there to work while building an incredible small business with a delicious product. And she's working on working with hotel chains to place her popcorn inside those hotels so that they can raise awareness about trafficking, which often happens in hotels. And so this is, you know, she's a very mission driven entrepreneur. She's a social entrepreneur, and she represents a whole nother set of motivations for our community. There's so many social entrepreneurs, people who want to solve big problems, and along the way, that takes money, but that's not the primary motivation.
Kevin Gentry
All right, well, it's time to start bringing this to a close. But before I pose the usual wrap up questions, just a couple more questions for each of you. First, I want to go back, if I could, just to the cryptocurrency space. Nick, if my memory serves me correct, you were one of the first to donate bitcoin to a US college way back when it was just sort of unheard of. Where do you. I mean, so we know that you're a visionary, you're a bold person in many ways, but how do you see that whole area influencing the future? You talk about the disruption that's going to come from artificial intelligence. How do you see the influences and disruptions that will come from cryptocurrency?
Nick Carey
Well, we will have to probably have a much longer podcast on that at some point, Kevin. But yeah, I was credited with doing the first donation ever to university using bitcoin. And it was actually really hard at first. They weren't sure whether or not they wanted it or if it would be permissible. And so we had to go through this whole exercise. But ultimately universities get all kinds of alternative assets donated to them. Could be artwork, sometimes it's portfolios of investments, real estate and more. And so after speaking with them, I got them comfortable with, with doing that. And I wish they had held on to it because it would have been quite a bit more valuable. They ended up selling it right away. But that's okay. It was an opportunity to educate. Now many universities accept cryptocurrency for tuition. Notably, MIT and Stanford have hundreds of students that are paying for their annual tuitions now in digital assets and digital currency. I think if I were to summarize why it's so interesting and important to me is just the financial system as it exists today. Most people probably haven't been through the deep exercise on how it works, how it's protected and regulated, who has access to varying credit lines and more. And it's very complicated and they have a lot of fancy vocabulary deliberately to make it seem more intimidating than it really ought to be. But fundamentally it doesn't work fairly and it doesn't work equally for all people. Depending on the circumstances of your birth, your credit score, what jurisdiction you were born in, you may never have access to a bank account. You will likely rarely have access to any form of meaningful credit and access to more sophisticated financial tools. So the, the idea behind crypto and really bitcoin, the first crypto project was to build an alternative financial system and a peer to peer electronic cash system that would enable anyone, anywhere in the world instantly to make payments online just as simply as we can send text messages or emails. And we have a long way to go, Kevin, if I'm being honest, to fulfill our vision for all of that, which would ultimately essentially be to create capital markets on the Internet where anybody on earth instantly could send, receive, secure, trade and exchange anything, whether that's dollars, online, digital currencies, equities, data as an asset class, renting AIs to do work for you, and much more. And we need a very scalable, high throughput, very decentralized system so that the incentives aren't to rent, seek on top of it. And banks today make all of their money off of the money you deposit in them. So I think a system where you as an individual are rewarded for participating in it makes a lot more sense. And the truth is it's going to take a while to transform and persuade the wider population of the world. But in all adoption curves, you cross the early adopters and the chasm and then you get into mainstream adoption. And I think it's very clearly in that epic today. And I think it'll take my lifetime of work probably to get it across not even the finish line, but in the right direction. And, and I think that's quite a worthy goal. But at the end of the day, just I believe anyone in the world should be able to pursue entrepreneurship and the work beau valiantly does on this with a heroic amount of effort every day. You know, I think we keep working on this problem set and you know, we'll build an incredible movement that enables anyone to come tract us and try and get supported in their entrepreneurial dreams.
Kevin Gentry
Well, Nick, you've received a lot of well earned credit for how you have democratized and the whole approach to how we access capital and utilize it as exchange. And so thank you for not only that, but also what you're doing with Sky's the Limit. And to that point, Bo, you know, Nick is giving a tremendous amount of the value that he's created for society to contribute it to Sky's the Limit. But we know that's still just a drop in the bucket for what you really want to achieve. You want to go really big. Sky's the Limit. So help me if you could help those listening understand if someone wanted to contribute very generously, let's say $5,000 or $25,000 to Sky's the Limit, what would it do, what would it achieve, what would it help you do in terms of helping these would be entrepreneurs overcome the obstacles they face.
Bo Ghirardelli
Yeah, thanks, Kevin. We do have huge ambitions and $25,000 will make a real difference. We can serve 3,70 entrepreneurs about in this year with that money. So I think that's serving them through
Kevin Gentry
your online platform in terms of the educational piece, the mentoring and coaching, and perhaps even the cap.
Bo Ghirardelli
You got it. You got it. And I think what's pretty interesting about that and what is a big part of why we take this technology based approach to solve is because it's not only the way that many of the people we serve want to access resources, they want to access the online. But so much of the nonprofit ecosystem is still brick and mortar based services. And, and that comes at a real cost. So $25,000 with Sky's the Limit could have the same impact as, as 425,000 placed in a brick and mortar nonprofit. And so that, that's 17 times more efficient with, with Sky's the Limit. And that is many more lives changed. Right. And each entrepreneur that we support is not just standing as an individual. They rep, they're a member of a community. They're building products and services. They're going to touch the lives of dozens, hundreds, thousands of customers. And so the ripple effect from entrepreneurship is truly powerful. And there's so much leverage and every cause that people care about, whether it is health or education or the environment, we have entrepreneurs who are solving problems in those spaces every day. And so investing in an entrepreneur is an incredibly leveraged investment. And that's part of what keeps us motivated to do this work at Sky's the Limit.
Kevin Gentry
Well, that's awesome. And you're right, that is such an untold story is the gains to society and progress and prosperity, innovation that entrepreneurship brings. And when they're not able to tap into that, we all lose out. So good for you. All right, in bringing this to a close, I have one question for you, Beau. One question for you, Nick, to close this out first. For you, Beau. I often ask now, thinking back on a younger version of yourself, you're still a young guy, but thinking on an even younger version of yourself, maybe your college years even before then, I think you all will start helping an entrepreneur when they're 18. So let's consider an 18 year old version of yourself. What would you tell that younger version of yourself to do differently today? Now that you know what you know,
Bo Ghirardelli
that's a tough one. I sure certainly had a lot more hair back then, but I was not much older than 18 when I got started with Sky's the Limit. And you know, I was in my mid-20s. So, you know, if I was doing it again today, I would say get clarity around your messaging sooner. Reach out to even more people and build long term partnerships with them. Find people who really care and want to be in partnership with you. And then lastly, I'd say you need to become an AI savant and you need to get on that ASAP and leverage that tool to accelerate the impact you can have.
Kevin Gentry
Well, I'm so glad you brought up that particular BO because I speak to groups and ask nonprofit leaders if they're using artificial intelligence and they're fundraising and very few raise their hands. I'm like, guys, you're going to be left behind. There's so much power to tap into with respect to that. All right, Nick, close us out. Now. For all those listening around the world from the experiences that you and Beau have had with Sky's The Limit and other experiences, what encouragement would you give? Let's say we're would be entrepreneurs. Maybe we're would be social entrepreneurs even. What encouragement would you have for us to think about going big?
Nick Carey
Kevin, I really appreciate you asking that question. I was thinking back, like you said, we've been talking now for six months and even with all the things you heard today, Bo and I needed to get some counsel and some mentorship and we were been very grateful to turn to your wisdom and your experiences with 10x. And the reason we came to you was sometimes brands matter, but reputations do too. And we have huge ambitions for Sky's the Limit. We think this problem is so big that it will require hundreds of millions and someday billions of dollars to intervene. And so we're on a long term mission to deliver on this promise of helping all entrepreneurs achieve their potential. And that's why we called it Sky's the Limit. And for anyone that looks up at the sky and sees a better future for themselves, we want them to sign up to Sky's the Limit. Join our community, participate, learn, come with an open mind and then we will be there to help support your journey. And at the end of the day, you know, we're all better off by trusting each other, growing together and learning together. And that's what Sky's Limit is all about. And for any funders listening, we would absolutely welcome your interest in learning more about our organization. And if you wanted to learn more, you can get in touch with us@skyeslimit.org
Kevin Gentry
well, I can't let you close out without saying in my experience over the years in helping groups, great causes like yours go big 10x, they're fundraising. You know, you've got to get the messaging right. Having that hole in the marketplace and a prospect's mind is very important, really. Understanding a lot of the frameworks that drive behavior, building the right culture, but nothing beats leadership. And you all have that in terms of passion and energy and drive. And I applaud you all for it. So looking forward to having you all back in a few more years. Tell us all about the progress you've made at Sky's the Limit at helping build a whole new entrepreneurial class in the world and helping us go forward. So thank you guys. Bogartelli, Nick Carey, thanks for joining us today.
Bo Ghirardelli
Thanks so much, Kevin.
Nick Carey
Thank you very much.
Kevin Gentry
Thanks for tuning in to the Going Big podcast. I hope today's conversation left you feeling energized and ready to tackle your biggest goals. Don't forget to subscribe and leave us a reminder review on iTunes, YouTube or wherever you listen to podcasts. It really helps spread the word and it gets these inspiring stories out to more people. You can also find more content, resources and updates at our website, goingbigpodcast.com Remember, the only limits are the ones you don't challenge, the limits that you impose on yourself. Keep pushing, keep growing, and above all, keep Going big. See you next time on the Going Big Podcast.
GOING BIG! WITH KEVIN GENTRY
EPISODE SUMMARY
Going Big with Bo Ghirardelli & Nicolas Cary: Sky’s the Limit and the American Dream
February 23, 2026
Episode Overview
This episode of Going Big! features a dynamic conversation between host Kevin Gentry and guests Bo Ghirardelli and Nicolas Cary—co-founders of Sky’s the Limit, a digital platform designed to empower low-income, early-stage entrepreneurs with the tools, mentorship, and capital needed to start and grow their businesses. Together, they explore the crisis in the American Dream, the roots and growth of Sky’s the Limit, disruptive forces like AI and crypto, and the transformative power of mentorship and entrepreneurship.
“There wasn't a good place for folks to turn to, to learn about how to start a business... millions of people have talent but don’t know how to channel it into building a business.” (04:07–05:30)
“People are losing faith, I think, in their ability to succeed on their own merits. And we want to intervene right there at the earliest stages of their entrepreneurial journeys to be partners with them, to be support for them, and ultimately to help them achieve their potential.” (07:39)
“I believe [entrepreneurship] to be an extraordinary empowering mechanism for people's personal agency...” (18:46)
“That upbringing...focused on living for something greater than yourself. Purpose was a big deal... Sky’s the Limit is an amalgamation of two passions: entrepreneurship and making a difference.” (23:05)
“With a mentor, it's almost more like I want to discover something about myself. That requires a relationship where there's a lot of vulnerability... what do they stand for? How do they behave when people aren't looking... what's their character?” (38:40)
“Finding the right person at the right time is the problem to solve... magic happens, but you gotta work for it.” –Bo (41:47)
“I like to describe it as the business code of ethics... always take care of your customer and take care of your customer first.” (45:00)
“She's working on placing her popcorn inside... hotels so they can raise awareness about trafficking.” (46:18–48:29)
“At the end of the day, just—I believe anyone in the world should be able to pursue entrepreneurship and the work Bo valiantly does... we keep working on this problem set...” (51:46 – 53:03)
“Each entrepreneur that we support...they're building products and services. They're going to touch the lives of dozens, hundreds, thousands of customers. The ripple effect is truly powerful.” –Bo (54:07–56:05)
Nick:
“We think this problem is so big that it will require hundreds of millions and someday billions of dollars to intervene. And so we’re on a long-term mission... For anyone that looks up at the sky and sees a better future, we want them to sign up... we're all better off by trusting each other, growing together, and learning together.” (58:21)
Bo to his younger self:
Nick to future entrepreneurs:
This episode is a compelling call to action—not just for aspiring entrepreneurs but for those who wish to support them. The conversation brings to light the scale of the opportunity gap, the need for scalable, tech-enabled solutions, and the indispensable role of mentorship, resilience, and purpose-driven leadership. Sky’s the Limit embodies a new approach: leveraging networks, technology, and philanthropy to democratize the pursuit of the American Dream.