Welcome to How Leaders Lead where every week you get to listen in while I interview some of the best leaders in the world. I break down the key learning so that by the end of this episode, you'll have something simple you can apply as you develop into a better leader. That's what this podcast is all about. And today's guest is Alexa Von Toble, a financial services entrepreneur who founded two highly successful companies before she turned 40. In fact, she sold her first company, LearnVest, for $375 million, and now she's building inspired capital into a powerhouse. Alexa is one of the most impressive young leaders I know, and I know you're going to learn a lot from this conversation. Now if you want to be a successful leader, I'm sure you know it's not always easy. There's always some bumps along the way. You're going to face some tough times and lots of uncertainty. And I mean lots of uncertainty. There will be moments when you don't have all the information you want. There will be moments when you don't have all the answers you need. So what are you supposed to do then? Well, the successful leaders I know keep moving forward. They fight through it. They lead their teams in the midst of the uncertainty. You're about to experience a masterclass from Alexa about how to navigate this well, and I'm excited for you to listen in. So here's my conversation with my good friend and soon to be yours, Alexa Von Tobel. Alexa, thanks so much for taking the time to be on this show with me. I appreciate it. Thank you so much, David. I'm honored and this is going to be a ton of fun. You know, Alexa, you certainly do have an amazing story. I'd like to go back to the beginning. Could you tell us about your upbringing? Sure. So a little known fact, I was born in Kentucky. Really? You know, I'm from Louisville, Kentucky. No way, David. I mean, now we know. Okay, that's for you, Tess. We know, because there's not many of us. No, I was born in Kentucky, Madisonville, and then moved to Jacksonville, Florida when I was eight months old. So I'm really in my heart, a Floridian. Grew up with two older brothers. My parents, my dad was a pediatric specialist and my mom is a pediatric nurse practitioner and they actually specialized in children who had really rare issues at the time, things like autism, ADHD, a bunch of that early work that was not that well known about in the 80s and 90s. And then I, again, I attribute a lot to being the youngest and to having tooled our brothers who really looked after me, but also kind of always said to me, if you want to hang out, you got to keep up. And that really set a tone for your life. So your mom was a nurse, your dad's a doctor. What was it like growing up in a medical family? I always joke that I'm like, I don't know if I ever saw a doctor myself when you have that many people and both my brothers are actually doctors, David. So no, I think my name is Alexa, right? Which now everyone knows from Amazon's Alexa, but my parents really believed in using your God given talents to give back. And actually, Alexa is Greek for helper mankind, Alexander and Alexa. And hence, why Amazon named it the helper of mankind. And I think my parents just had a very strong point of view on taking your talents and making more of your community and helping to give back to people that are less advantaged and that was very much just like in my everyday existence when you grew up in a family who goes to work all day long to help people who really, really need it. So I would say it was a great foundation for my values. I talked at the top of the show. I talked about how every leader has to work through uncertainty. And certainly you had that very early on in your life as I understand it, your father actually passed away when you were just 14 years old. How did that impact how you lead the day when you reflect on it? I mean, so much. And I'm so glad you brought that up, David. Having something really unexpected happened and obviously losing a parent as a child, it's your worst fear. It truly is. And then when it comes true, I think, and I'm now what it's like 20 plus years out from it having happened, you never really get over it. And I think I've always been a really positive and optimistic person my whole life. And it actually didn't change after that happened. If anything, my way of healing was sort of seeking for the how does going through something like that help you. And for me, life is really precious. And David, I remind people this every day, which is this isn't the dress reversal. We only get to do this once. And that's it. And this is it. And I think very much it kind of taught me that nothing is really that bad. And what I mean by that is, you know, all through COVID is everyone around me at times was stressed and anxious and worried. I said, I realize it's a roof over our head to be food. It's not that bad. Like it could be so much worse. And so I think that having that is almost in some ways an existential strength. And you asked, how does that help me lead through ambiguity? Nothing's really that bad. It's still alive and healthy and well. And so it's just always given me an extra gear that I can turn on in the face of tremendous stress and chaos and concern that just says, it's not that bad. And we can keep going and we can keep working and we can prevail. That's such a great perspective. And, you know, it's helped you manage through all the things that you've done, you know, starting up these businesses because it's not easy when you go through that. And then you had to go through that and you were with your mother. Okay. And what was it like just going through that experience with your mom and what did you learn from it? First of all, my mom is absolutely the hardest working person I know. And I think one of the things, again, we all learn by watching the people around us, right? And now that I have children, I'm so mindful of what they see and how they see us, you know, move through this world because so much of what you pick up from your parents is just what they do. My mom woke up every morning at 5am, would get us out of bed, would pack our lunches, would, you know, even through everything she was going through in her life. She truly was just a rock of making sure that all of the things we needed were right there. And, you know, in retrospect, I mean, my mom has always been somebody that I admire. And now that I have three kids of my own, oh my God, I David admire her so much . I'm truly blown away by the sort of things that she was able to do and keep all the train-running for us through everything that she was emotionally going through. And again, that kind of comes back to a little bit of my orientation on life, David, which is like, things are, you know, we're alive, we're healthy, we're here. And then number two, just this incredible work ethic that through everything, rain, sleet, snow, hardship, stress, anxiety, just if you put in the work, good things happen. And I really do believe that is a North Star to me. And one thing I will quickly say as an entrepreneur, David, and you know there are days at work where you get your gut, literally your gut punched, you can't breathe because something so bad is happening that you're so anxious and worried about. And I think one of my orientations was you have to show up every day and give 110%. And there's days where you're allowed to go home early. So you have to start the day at 110%. But on the days where you get your, the wind knocked out of you, it's okay if you go home at four. There's just something, you know, we're human too. So the end of the thing is, you know, I don't want it to come off as, you know, crazy hard work at all times. Like, there's a balance to entrepreneurship, but I always start the day with 110%. And I think that really was something, a lesson that I watched my mom really give me, which she started every day at 110%, five o'clock in the morning, providing us with everything that we needed despite everything that she was going through. Yeah, you only have so many assimilation points, you know, you can only take it so much. And I think a leader's got to figure out when it's time to say I give at least for a day so you can come back and fight another day, you know. You're allowed to go home and have a bad day. That's allowed. Yeah. You know, I understand then, and you know, your, your, your mom and your dad's intelligence obviously was passed on to you and the hard work ethic. And you go on and earn your way into Harvard and you get a degree in psychology as I understand it. What drove that decision and how did you move from psychology to business? Yeah. So I think my whole life, David, I've always loved people. You can ask, you know, my, my whole family at five, seven, ten, I actually was a new student in sixth grade and literally ran for president of my brand new school, my brand new class of friends and, and actually ironically one, which was hilarious in retrospect. But I've always loved people and I really do. I find people fascinating. You meet me at a party. I'll be like, hunkered up next to somebody being like, tell me about who you are. I want to know who you are. And so psychology just was genuinely something I was, I was, I was, I was fascinated by our minds and how they work and, and then no surprise, I've always been a really positive, optimistic little creature. And so I found my way into the happiness lab at Harvard, which Dan Gilbert was, was, was working on the science of happiness. And then I found myself into mind-grained behavior and positive psychology. And I just studied something that I loved and that, that's that. And was so grateful for doing it because the whole meaning of life is not always work. And you know, it's really finding fulfillment, finding that deep self-actual ization and, and, you know, no, no surprise there, David. It doesn't come from taking easy paths. It often comes from taking hard paths and working hard and overcoming adversity . And so actually working in the happiness lab gave me a really great framework for understanding my own self-actualization and who I want to be and, and, and what, what makes me tick. And so, and he's, I, I loved it. I was fascinated. You know, I have to ask you this while we're on this. What would be the one thing that you've learned really boils down into personal happiness? So it's really straightforward actually. And I wrote the beginning of my senior thesis on it, which was they took groups of people and they said, you can either write down one thing that you've always wanted to come and sure will give it to you that will make you happy. Or if you're like a coffee and tea drinker, just your regular cup every morning , perfect. What makes you happy? Unsurprisingly, most people said, oh, I know myself so well. I'll go to the top of my list and I'll pick the thing. And the, the punchline of that is we're really bad about knowing what makes us happy. What makes us happy, David, is consistency, continuity, knowing small things that you love that add up long periods of time, like the great cup of coffee or being married to somebody like waking up next to. But again, on the list, people are always like more money, more things, bigger house, you know, winning the lottery, unsurprisingly winning the lottery doesn't make you happy. In fact, it actually makes people really, really, really unhappy. And so the takeaway from that is it's really simple things. It's knowing what gets you excited, being with people that make you happy, simple, simple things. It's not consumption. So it was a great orientation to be 18 to 21 and learning about those things. I think it created a great foundation. Yeah, you get that at an early age. Obviously helps you as you go forward. And you know, you seem to be someone who's gotten a lot of joy about the businesses that you've created. You know, when did the light bulb go off or learn vest and tell us about it? Yeah. So you asked, you know, how did psychology go to entrepreneurship? But if you go back in my own life, I was an entrepreneur very early. I remember having a little piggy bank and trying to do things so that I could buy more leotards because I was an athlete. And then I remember, you know, I didn't like have a lemonade stand. I was just like selling things for my house like on the front street, like literally like on the table. My mom at one point, I got in a lot of trouble for taking like a little piece of art off the wall and like, you know, going and selling it. My mom's. No, is the headline there. All that said, when I got to Harvard and graduated, I had this huge light bulb go off where I was like, I'm an entrepreneur. And the truth is my dad was an entrepreneur. He'd run his own, his own medical practice. And my grandfather was an entrepreneur, he had started a series of lumber yards like Home Depot's and the more I thought about it, I was like, oh my God, this actually like runs in me. I am an entrepreneur. And it was one of these big moments, David, where the light bulbs went off in my head where I was like, that is my like love of building. And I really do love to build it. So the idea for learn best came from when I had graduated. I've been fortunate to get into Harvard Business School. I got great jobs on Wall Street on investment banking sales and creating and all these offers. And I remember thinking to myself, it's the first time in my life where I'm making my own savings, my own money. And I always wanted to have my finances ironclad. And I remember when I lost my dad, my mom overnight was taking care of our finances. And that she's quite capable of doing that. But she hadn't really done it. And I just remember having this like really clear thought that said, I will be good at this. Like no matter what, my whole life, I will be able to take care of my own finances and be really empowered in it. So I went to Harvard, no classes on it, David. Literally financial literacy zero. And after I graduated this light bulb went off where I said, I'm sitting here and I'm very good at finance and very good at math. But I can't believe that I don't even know how to learn the basics of my wallet . Like how is that a thing where being, you know, somebody who's lucky enough to go to a great school and learn best was born because it stood for learn, earn, invest. You have to learn about it. You have to earn it. And then you have to take care of it. You have to invest it. And I said, I'm going to go build that for modern people online for America. And then once that light bulb went off and everything turned, I was infected. I couldn't get out of my head. And I actually found it. It may have 2007 and I didn't drop out of Harvard Business School until December 18th of 2008. So I was really percolating on it for a while there. This is amazing though. When I think about it, you're in Harvard Business School, which is such an incredible feat by itself. You've got that amazing accomplishment. And then you muster up the courage to start your own business and you actually drop out of Harvard. You had to have a million people tell you that you were crazy. How'd you handle all the nose? It's so funny. You're absolutely right. First of all, I had a million people. I'd be like, God, this is crazy. I even had one of my own best friends in the world grab me and say, don't do this. You should not drop out. Like, the world doesn't turmoil. Lehman Brothers had gone under. It is a crazy time. Don't go do that. And honestly, it kind of goes back to my life orientation of I was okay having my own point of view. And I didn't need that validation from somebody else. There's this psychology study, David, that I learned about where they took people in their 90s and asked them, what do you regret? And here's the punchline of that whole study, which is they didn't regret things they did. They didn't regret the person they kissed or they didn't regret the job they quit or none of that. They always regretted the thing they didn't do, the swing they didn't take. And so I always joke that, you know, 90-year-old Alexis sits on my shoulder and she's a tough cookie and she's very clear on things I would regret. And so once I knew I would regret not doing it, I didn't really care if nobody else cared because I was like, this is my life. I only get to live once and I've got to do the things that are my true north. And so that was that. And so I dropped out and I actually walked into the admissions office and I said to the woman, I tears my eyes, I said, please don't try to convince me to change my mind because you will probably be able to convince me and I need to go do this for myself. And I walked out and then I had dropped out and I thought to myself, oh my God, you're insane Alexa. And the next day I felt fine. I said, it's time to work. Let's keep going. You know, I love how leaders make big decisions. That's such a great story. Tell us about how you made the call to leverage the internet and then how you built your business model because you really disrupted the category. So again, I keep it simple. I'd written a business plan, David, that talked about the chapters of the business. And the first was we're going to have tons of content and then we're going to have tools to help you know where your money is and what it looks like. And then we're going to offer financial advice. And what was so straightforward for me was the financial advice piece was really the big disruptor because people had never made it affordable for the masses. For the most part, financial planning and financial advice was done for people that had loads of money. You know, if you had millions of dollars, everyone wanted to give you advice and they would take one to 2% of your assets and it was very expensive, but you didn't probably totally process that. But if you were young and just getting started, there was no place to go. And so back to kind of keep it simple, stupid. I literally just said we will be transparent. You'll know what it costs on the website. It will be super straightforward. It will be designed for everyday normal people. And we had sort of flipped the industry on its head because rather than being available Monday through Friday from 9 to 5, we'll said we'll be available 24 hours a day , 7 days a week. And we will only charge you for advice and sell no product. So you never are concerned that we are completely aligned to you. Again, super simple. And quickly we started to see it was working and we sold directly to everyday consumers. And David, at first I assumed it would be all young people. You know, in their 20s and 30s who love to use the internet. But little by little we saw it was people in their 40s and 50s and 60s and 70s and all of a sudden I kind of had this moment where I said, wow, this product actually makes sense for everybody. And when I started, we weren't even, you know, FinTech wasn't a thing. It wasn't really until the summer of 2014. So almost six years later when they put me on the cover of Forbes and literally called it the millennial revolution of the wallet, that they were finally pure. They were finally other people working in the category on the consumer wallet. And now kind of David, you fast forward, there's Chime and Robinhood and all these amazing companies that are worth literally tens of billions of dollars. And looking back, I was probably early to the move. I mean, I was early, but it was, you know, some days I think about, oh my God, what if I was running LearnBust today? I think it would be so much easier because Zoom existed and all these other things. You know, and you did really simplify things. You know, I've heard, I've read where you said you'd be mystified in financial services. And you had the really terrific insight to help people focus on cashflow. Why? It was so simple, but David, 78% of the country lives paycheck to paycheck. And through all this, I became a certified financial planner, which is sort of the doctor of money. I was like, if I'm going to do this, I'm going to do it right and I'm going to do it to the highest degree of expertise. And once you go through that exam, you really realize most of the country, 78% in COVID has actually sent that number up, live paycheck to paycheck. Most people don't have $400 of savings. And most of the software, I use that in air quotes, that was helping advise people with, you know, loads of money, wasn't based on people's cashflow because it didn't have to be because people who have enough money don't have to worry about can they pay their bills. And so we built financial planning software that was based on real cash flows so that we could help everyday people be able to afford month by month living. And then when they had extra, teaching them how to have extra, figuring out what to do with it. Now, you launched this business in the middle of a recession. You know, talk about, you know, really taking a gamble or what people would think would be a gamble in such a time of uncertainty. But in fact, as I understand it, you said this is a wonderful time to start a company. What kind of cool aid were you drinking? I will never forget it. I was on an elliptical machine at the gym and I was studying for some tests and Lehman brothers just going under on the television. And I had three friends text me being like, I'm going to lose my job. I'm so scared. And I had this really, really lucid moment where I said, this is the best time to launch a plan, a company that helps everyday people figure out what to do financially. And again, it was the right time for the idea and the business. It was the absolute scariest time for me as the vehicle of that idea. But I, that kind of goes back to, you know, David, somebody once said this to me and it like is burned into my DNA, which is when everybody's egg you have to zag. You can't run where everyone else is running. You got to run where people aren't looking and you got to run when people are too scared to run. And it was just the right call. And I knew it deep, deep, deep in my heart that it was the right decision and then I just had to have the guts. It was really about having the courage to actually just follow through. You know, when I was at Pepsi, we did a campaign, I remember doing this campaign for Mountain Dew, which we use this line, been there, done that, you know, which became a part of the verdacular. And I think this is really a great opportunity to give our listeners some practical wisdom here on this subject. When you think back about it, you know, had to navigate through all this, what people would describe is uncertainty. What would be three to five things that you could tell leaders to think about when they're going through times like that? Well so, one of their just quick fun facts, so David, speaking of like navigating through uncertainty, I sold my business on March 25th of 2015. I was literally nine months pregnant and had my first child that weekend. So that week of my life quite literally was the most uncertain week because this tremendous event was happening. That was going to, you know, and I took very seriously my responsibility of being responsible for every employee, every shareholder, you know, hundreds of people to deliver this major exit and at the same time I was quite literally nine months pregnant and that was the week that I really understood. When you're leading through crazy uncertainty and again physical uncertainty, right, I didn't quite know how, you know, I was going through a life changing event, the most important life changing event of my whole life, which is my child. And in those moments, I just, I learned to break things down into chunks. I'm like, let's take today, let's tackle this morning, let's tackle this afternoon, let's tackle this evening. Like sometimes you just don't need to think two weeks out, three weeks out, it 's just like, let's just tackle today, let's make it bite size. So that's one tactic. Another tactic is just to remember to keep things in perspective. And that kind of goes back to like my own roots of like, our real life is the roof over your head. You're, we're okay. And I think that was another big one. The third was communication, which is, you can probably tell from this, I've been described by many people in my life as hyperinverbal. I'm a, I talk, I'm very comfortable communicating, telling you what I'm thinking, what's happening, where we are going. And in those moments also just being able to communicate to everybody around you, what you need, what do we make, what do we need to do to make this happen? What are the road blockers? And sometimes I find people get very overwhelmed and then they actually stop communicating. Or if there's too much happening, they don't communicate. And I'm sort of the inverse, which is when things get more trying, I communicate more because I find it allows people to know where you are, what they, what you need , how do we make these things happen? So those are just a few basics. And then finally, the value of sleep, David. Like when the world is being thrown at you, you have to be able to be clear headed. And so kind of being able to keep, like just at least getting six, you know, six minimum hours of sleep through high moments of stress. And if you go think about athletes and I really do attribute being a leader to being an athlete, because you're being asked to do something that is superhuman at the top of your sport or at the top of the game. And just physical well-being, physical care, eating meals, like it's sort of basic, but it's pretty important. So great communication, keeping things in perspective, breaking things into smaller chunks. And again, just making sure you're eating and getting sleep and just taking care of yourself. And because our minds, you know, just like you take care of your muscles, if you're going to go exercise, like your mind is an important muscle that you have to take care of. Absolutely. You know, you describe yourself as a hyper-communicator. One of the things that I've already picked up is you're a very clear commun icator and you're able to simplify things. And you know, you called, learn vest, the TurboTax for financial planning or your GPS for your money. You know, these are great word pictures. Do you work hard to simplify your communications like that or does it just come to you? I've never like gone through a program. I think, again, I'm a third child, like your whole life, I'm just trying to make sure I get what I need and tell people things. And it's so funny, David. I have three children. My youngest is a little girl. And somebody yesterday said to me, "Oh my God, she speaks so well." And I just said, "She's a third." And she's two. And I was like, "She's a third." And this woman was like, "Oh, of course." And so I think that there's probably got to be something pretty rooted in my orientation of being the youngest of two older brothers. But I do think communication skills are paramount and it's something I'm going to make sure all my children learn and public speaking and standing up and speaking to a crowd and being articulate is an important skill. You know, so your business takes off and learn vest is a huge success and you had all kinds of people wanting to buy you, I'm sure. What was behind your decision to sell and to sell to Northwestern Mutual? And you mentioned all these FinTech companies that have multi-billion dollar market caps. Any regrets at selling so soon? You know, this goes back to my, I don't believe in regret. It's just like a really big waste of energy. So even if I did regret it, I wouldn't let myself really process that. But no, I don't regret it. It was such a clear decision for me. And here's kind of how I went about it. Again, I took my job as CEO very seriously. I was legally responsible for an entity with shareholders and many investors and, you know, hundreds of employees. And so I said my job is to take back to the board the best options that we have . We weren't looking to sell, we had lots of cash, we had just raised about $35 million and had about $52 million on the balance sheet. And I remember thinking, my job is to look at this decision and then bring it to the group. And I kept kind of thinking to myself, when will I give myself the emotional space to process this? And it really was basically the day before when I kind of had like my own little moment of silence where I said, what do I really believe is in the best interest of what we built? And we signed all the documents and the board of Northwestern Mutual asked me to send a quick video that just said why I was excited to enter this. And they really called it a merger, which was adorable because Northwestern Mutual is worth billions and trillions of dollars. Literally, man, I just half a trillion dollars of assets and little learn best was this big. And the CEO is just the most spectacular man as named John Schlitsky. But I actually sent a video to the board and said, I waited till today to really process this. And it was actually a Northwestern Mutual life insurance policy that stabilized my own family after my dad had passed away. And I said to them, I know the power of what this brand does for a family. And they have 8,000 financial planners who go around the country to protect families from the unthinkable. And I said, I literally don't know a better place to go put something that I had spent at that point almost a decade of my life building. And so it was that simple. That's so cool. That's an emotional story. Yeah, it was one of these moments where I said, I feel like my dad's looking down on me and I know exactly what I'm supposed to do. He's got to be so proud. I can tell you that. So you sell to Northwestern Mutual, like you say, this billion dollar company. That had to be hard, though, going from running your own show to a more bureaucratic environment I understand you're the chief digital officer and then took on more responsibility. How do you shift your mindset, Alexa, from leading your own company and being part of a larger organization? So, first of all, I mean, I really knew what I was getting myself into. We spent a lot of time thinking about how do we come together and, again, we used the word combination. But we really did share a value system. I believed in financial planning for everyday Americans, Northwestern Mutual for 161 years had been protecting everyday Americans. And so when you have, it's sort of like a marriage. If you share the same value system, you can put a lot on top of that. And so I went into this eyes wide open and I really said to the CEO, I said, I committed to stay for three years. And I said, at the end of that, my goal is really simple. I don't want you to regret your decision. I want you to feel it was one of the best decisions you've ever made. And so that was my orientation. I was like, if I'm going to do it, I'm just not going to be, you know, most founders sort of sneak out the back door and are ready to get out of it. And it is hard. And you know that going from being the boss to being, you know, I was still CEO . I've learned best, but then I took on a role where I reported into a CEO. But I went into it eyes wide open, David. I really knew what I was going into. And I kind of took this as like the end of my MBA intellectually. And I said, I'm now going to get to go inside of a company that has, you know, thousands of employees and literally budgets that span, you know, truly just masses amounts of money. They do almost 40 billion of revenue. And I'm just going to learn everything. Like I'm sponge. I was, you know, 30 years old. I was like, I can soak in so much from this, this learning experience. And I'm so grateful they invested so much in me, David. And I really did learn so much. And probably one of the most important documents of my life is a note that the CEO gave me after I left, where he said that it was one of the best decisions of his entire career. And my husband's so cute. He literally framed it. But as you would imagine, it was there were moments of it. They were beautiful and so exciting and so much learning. And then there are also moments of course, it's like you're taking a tiny, fast moving company in New York that's like focused on breaking things and a big company that has just such tradition and such values and can think in decades and you're bringing them together. Like, I mean, that's like a punchline of integration. And so our commitment was just to this North Star, we're going to make sure that we build something better. And I'm really proud that that's where we are. That's great. I love the fact that your husband framed that letter, which has meant so much to you because that was the goal you had when you set up. That's fantastic. You know, so how'd you end up founding Inspire Capital? So you kind of get a sense of how I think and operate. And when I was building LearnVest, I would drop down a Harvard Business School 24/25 and I was in New York City and I remember having just this simple moment where I'm like, I am in New York City. Where is the capital? Literally, I kept getting on planes and flying to the West Coast and then I have to raise more capital and get on a plane and fly. And I kept being like, New York City is the capital in my mind of the planet. It's just this incredible place of art, history, culture, grit, stamina, tech now, crypto. And I just had this deep moment that where one of my board members was this incredible entrepreneur. His name is Lee Barba. He was part of selling a company for about a billion dollars to TD Ameritrade. And he was simultaneously David the toughest grader of me and the most empat hetic, loving, supportive mentor of mine. And he made me so much better single-handedly. He was this one human who just constantly pushed me and it would send me the notes at 3am being like, I know you're not sleeping. I'm with you. I'm not with you either because I'm worried about you, but I'm in it with you. And I just had this really simple kind of product market fit moment where I said if you built a venture fund that is chock full of people who've built companies before , who care about founders, not in this arms length way where you're like a selling a spreadsheet, but you really have been in it, you understand what it's like to build businesses. It's really simple. It's going to be a phenomenal organization. And it had always been in the back of my head. And then one day I was sitting there and it came out of my mouth. I was like, it's just inspired capital. It's capital that knows and understands everything you're going through. And then I literally looked up and I said, is that name taken? And I bought it that day. And then once it kind of goes back to the basics, once an idea gets in my head, I kind of get infected by it. And I said, I really want to go build that business. And so inspired was born. And I made very few phone calls. One was to this woman named Penny Pritzker, who had been US Secretary of Commerce for President Obama. And instrumental now in putting people like President Biden back in the White House. And we had a deep, deep, deep, deep, deep shared history, lots of in common. We both lost parents when we were younger. We both have two older brothers. We both very much had a similar orientation and a truly fervorous love of building businesses. And I called her and said, hey, I'm thinking about this thing and this idea is in my head. And by the end of the call, she literally was like, can I build it with you? Let's do it together. And then the other phone call was to one of my best friends who had already transitioned to-- she co-founded Paperless Post. And she studied psychology at Harvard with me. And we turned in our senior thesis together and got parents of each other's children. And literally, she was my red phone every time I had an terrible problem that you can't solve because that's what being an entrepreneur is. And we basically said, I'm thinking of building this thing and each night I'd go over to a apartment and just sit there and talk about what it was and how I thought about it and got it out. And she was like, oh, what if you did this and what if you did this? And then one day I looked her and I said, are you an inspired couple? And she was like, I'm not an inspired couple. And so the other kind of big secret and you know this better than anybody, David, is building things with people that you love and respect because who the people are around the table is more important than the name and everything else. And so in the last partners, this guy named Mark Batty and who had been with me for almost 12 years and he and I were the deal team selling LearnVest and I kept joking. If he wasn't sick of me after working with me nine months pregnant, we're nights and weekends, we would do a second shift to sell the company and go through all of that when I literally was under slept and quite literally on my last energy leg. And he's absolutely brilliant. And so that was the team and then we just kept adding people that we love and trusted to it and 10 people in. It was, we have 68 years of overlap and we've founded 10 companies between the team. We just felt like that was the right ingredients to build a once in a lifetime special venture fund. You've got some great startups that you're behind and it was fun just reading through the things that they're pursuing. And Alexa, I'm sure you hear all kinds of business pitches, you know, but based on your experience, what's the fastest way to get a know and what would be the fastest way to get a yes? Fastest way to get a know, I'm going to give two short answers. One, to make somebody feel like you just really want to be a CEO and you really just want to build any company and then to not have enough depth. You can understand how deep somebody has thought about something by the level of detail that I give you when they answer your questions. So those are two pretty fast ways to get a nose is to not have enough detail and to have it really feel like you're a voyeur at entrepreneurship. The fastest way to get a yes is not fast. It's your life's work. There's no way to hack really caring about wanting to build something. You now have a sense of my orientation, David, like learn to just pour it out of my value system. It was just, I got infected with it and it was going to be over my dead body that I can figure out a way to build something special in the category. And so really seeing into the heart and soul of a founder, you get a sense of their why and what they want to build and it can come in lots of shapes and sizes. And those founders also, they do, they speak in decades, they know that they want to build something and they understand 10 years in it will maybe or may not be on the path to being successful if you're building it properly. Inspired capital, I can see why you bought that name immediately. You know, it's so purpose driven and it's so obvious you believe in the power of having a noble cause. Looking back, Alexa, who believed in you before you even believed in yourself? You got a lot of confidence now, but was there somebody who really kind of, you know, gave you that spur you needed? Yes. As I've said many times, I've tooled a brothers and it was amazing. They quite literally trained me. And you know, my middle brother, his name is Brandon, he used to go running with me at like 11 p.m. Quizzing me on like my AP biology exam. And you know, when I was sixth grade, first of all, he's the one who gave me my winning line of my running for office. What was the line? What was the line? I can't make this up. Brandon came up with it. He was like, everybody on the right side of the auditorium, raise your hand. Now put it down. Everybody on the left side of the auditorium, raise your hand. Put it down. Are those leadership skills or what? And I got a roar of laughter and I won. And you know, Brandon was the older brother that when I was in third or fourth grade, tapped me on the shoulder and said, I think you can read seventh grade books and gave me literature and maybe read it and then quiz me on it. And you know, just deeply, deeply believed that I could be special. And then my eldest brother was just a really special athlete. His name is Travis and he, it's so fun to now see him with my daughter because he's doing the same to her, which is, you know, he'll go, she was riding her bike and he was the one pushing her when, you know, just a year ago and he's like, you've got this in you. It's in your soul. And I just thought to myself, I was like, oh my God, he did this to me because he was eight years older than me. And I was a varsity diver and did many varsity sports and he used to literally go make me run and sweat bags and plastic bags and just crazy stuff like that, David. But he would give me the confidence that I could be the fastest and be the best and because of both of them, I'm sitting here today. That's great. You know, you've had so much success. But what's one day in business you wish you could relive because it didn't turn out the way you wanted it to. Oh, absolutely. There was a day where I was in the middle of changing out some really important talent and this person had showed up and it had taken me six months of finding, interviewing, six months of like extremely focused work. And this person finally showed up and within eight hours called myself and said , I'm not going to be able to stay. Something had happened and it was like a gut punch like you can't imagine. And I was traveling to close a business deal and literally I called my husband truly just sick. And he, so cute, he drove and picked me up at the airport, which nobody does in New York City. It was so sweet. He literally picked me up because he just knew I was like so deflated. And a second one, I'll just give you a second one because actually it's hilarious to me. So I dropped out of business school and we qualified for TechCrunch 50 and that means they pick 50 companies and you get to come present and they put you through a g auntlet and basically by qualifying they believe your idea is a big idea. And I stood up on the stage and presented in San Francisco on September 15th of 2009. I remember the exact day. And I was so proud to be there and I was presenting my company and the panel of judges and you can find it online. There was four or five of them. Literally looked at me like I was an alien and shredded my company with the following shreds, David. They said, I don't know if anyone will ever bring their wallet online that seems crazy. The investigation of money that seems absolutely idiotic. And I just, I had done the work. I leaned in and I was like, here's all the reasons you're wrong. But that was a moment where like people literally said Robinhood can't exist, Chime can't exist, all these massive businesses. And I was humiliated. I got off the stage and I said, I can't believe I'm here. And actually I was so, so, but it was, you know, I was so upset. I was like, I'm here. This is supposed to be a triumphant day where everyone understands our idea. And I kept joking. I got tech punched. I was like, instead of tech crunch, it was like getting tech punched. They literally just shredded the idea. And to this day, it's pretty funny, David, because it was, I felt my idea was so obvious. And now the world has made it obvious. And even these big tech guys thought it was a terrible idea. And that was a day that I'm now proud to relive. And that makes sense. A bad day that turned out great. You know, I recently, I've just completed a new book. You're a great author and you've written two fantastic books. I've written a book called Take Charge of You, How Self Coaching Can Transform Your Life and Career. And you know, as I listened to your story, Alexa, it seems like you've coached yourself through a lot of big moments. How do you build self-awareness and make sure that you follow your joy? It's a great question. And the answer is simple. You have to surround yourself, David, by people who absolutely tell you what you need to hear when you need to hear. And, you know, if you met my husband, he's this really wonderful, wonderful guy . His name's Cliff. And he is never, he will always tell me what I need to hear, even when I don't want to hear, even on the days when it's too much to hear. He will be the first person to say, "That was done. That was wrong. Don't do that. Please don't do that." And then around the business table, just surrounding yourself with people that you deeply respect to have zero trouble telling you that was done, that was wrong. Don't do that. Or just you're wrong, like passionately you are wrong. And so you can kind of get a sense that inspired. It's a bunch of people that have known me for a really, really, really long time. And I enjoy going out of my way of trying to create the psychological safety where people can tell me things that I have to hear to get to the right answer. Because it's not about being right, it's about getting to the right answer. And one fun fact, this great guy, his name is Mark Kelly. He's now the center of Arizona. But my husband and I became a good friend to him. He taught me this amazing story about when his wife, Gabby Giffords, needed surgery. He put the doctors in order of seniority and made the youngest go first. And then went backwards because you needed to get to the right answer. And you didn't want people to be swayed by who else was around the table. And so that always stuck with me as just the most important thing is to get to the right answer and to having people tell you what you need to hear that are not being influenced by the politics or the dynamics of a room. And it's hard to create those rooms properly, David. And it's about being mindful of having the rooms set up properly so that you get to the right answer. That is a great story. You know, Alexis, this has been so much fun. And I want to have a little more here with you do a lightning round of Q&A. What three words best describe you? Energetic, optimistic, and a believer. I'm a believer in entrepreneurship. What's your superpower? My energy. Now, you've got kids, so I know you'll have a good angle on this one. What Marvel character reminds you the most of yourself? Oh, my God. Oh, my God. I'm like, there's no character, David, that's coming to mind. That is like enough of a jokester. And I don't have one. I don't know. You kind of remind me of what is it, Black Widow or whatever? You're going to see where she does a little pose there. I can see you doing that. You're athletic. If you could be one person for a day, who would it be and why? I would love, you know what? I would love to be one of my great grandmothers and somebody I didn't really know and just get, you know, they're why I'm here and people who paid a foreign to me and just to literally like walk in their shoes and understand the sacrifices they made for me to be able to sit here. What's your biggest pet peeve? Oh, my God, David. I'm the most impatient human you've ever met. There's not an ounce of patience. I have to muster patience every day. It is a meditation. What's something about you that few people would know? I live for, like I live for singing. And I'm the least talented singer you've ever met in your life, just like not one ounce of talent. My husband and I both, like we would do anything to be able to be phenomenal singers because we just admire it so much. Do you have any hidden talents? You're not a singer, but you have a hidden talent. Yes, I can I can whistle with my tongue alone. And I mean, I have a bunch of random hidden talents, but no, I was a platform diver. I was an elite gymnast. I can sew. I can cross stitch. I mean, literally I've got a lot of random craft talents in my DNA. What's the favorite thing you'd love to do in your spare time? I like to build things. And it really took me into the last few years that my favorite thing to do with my kids is sit and build anything. We can build Legos. We can build a recipe, but like I love to make, I love to build things and seeing the process of starting and finishing is really satisfying. You know, I was really nervous, Alexa, about doing this podcast with you because you're you're a phenomenal podcaster in your own right, you know, with your founders project and partnership with Think Magazine. You know, do you like doing the podcast? I love it, David, for probably the same reason that you love doing yours, which is meeting people that have such unique perspectives is just such a gift. I think I consider it to be like a genuine gift to my own learning and my and anyway. So no, I love doing it. And it's so fun to get to understand how somebody thinks. Yeah, I love that too. That's exactly the exactly the case for me. Now I got to ask you this just a couple more questions here. Do you miss running a real business that sells something every single day? Is there another startup in your future? I literally feel like that's what inspired is. And I feel like it's this platform that I could do for the next 30 years because every day we are selling to the world's best founders of tomorrow, how to make them better. And that's endless. And so I still feel like, you know, I stood up inspired and the managing partner. I feel like I get to do that every day and I feel like I could do that for the next 30. So you have these founders. Do you kind of view yourself as a CEO in the sense that you're invested in helping each of these founders build their business and you're in it? Yeah. I'm in it and actually one thing is I don't know how to turn off caring. So when they're in it, I feel like I'm in it. And it's you know, you really know when you're in it because your brain just thinks about it, sleeps about it. So no one I very much feel like we're on the journey with them and that's extremely authentic. You know, I'm going to wrap it up here with this question. What's the one thing you'd tell any aspiring leader that they've got to have to be successful? I would say that in order to be successful, you need your own North compass. You need your own, you need your why that is not about money. It is not about fame. It is not about success. It is not about proving something to somebody else. It is so much deeper. And if that is what's making you tick and driving you, you will be more successful than you ever intended. And actually I'll end on this great quote somebody said to me once, which was, "Figure out what you love to do. Figure out what you're extremely passionate about and figure out what you're extremely talented at and do both as early as you can in your career and you will have tremendous success." Fantastic advice and Alexa, you are a superhero. You're unbelievable. I'm just pleased that I had the opportunity to learn from you and to hear how you think. And you're inspiring and inspire capital is that sounds like the perfect place for you to be. That's so kind of you, David. Thank you so much. I'm going to stand from afar for a long time and just truly grateful that you had me honored to be here today. Thank you. You know, when I listened to Alexa's story, it reminded me of 2008 when I was a director of JP Morgan Chase and when we had the financial crisis where everybody thought the whole world was turning upside down. You want to talk about uncertainty, people didn't know if every bank was going to go bankrupt, if they were going to be able to get their cash, you know, when the country was going to come out of this. I mean to tell you, it was a brutal time. And let me tell you something. I saw a great CEO in action then. I saw Jamie Diamond, the CEO of JP Morgan Chase, step up and handle this crisis with incredible poise. He could have been paralyzed. But no, he said, we've got to take the actions that will get the financial system out of the ditch and we'll get our country out of the ditch because this country and this financial system is the strongest in the world and we will be again. That kind of confidence in uncertainty, that action when most people could be paralyzed is what made him a great leader. So let me ask you, what is it for you? Is there a particular decision that you need to make? Are you feeling paralyzed? Is something holding you back from moving you forward? Well take a minute and picture that one thing in your mind. Take a minute. Okay, now you know exactly where you're stuck, where you're experiencing that uncertainty. I now want you to think of your very next action step. Now, I don't need you to think of the next 10 steps. What's the very first step? Whatever it is, take that step today. Don't wait, don't delay, let's get moving. So do you want to know how leaders lead? What we learned today is the great leaders have learned to navigate uncertainty and they keep moving forward. Thanks again for tuning in to another episode of How Leaders Lead, where every Thursday you get to listen in while I interview some of the very best leaders in the world. I make it a point to give you something simple on each episode that you can apply to your business so that you can become the best leader you can be. I'll see you next week. Bye.