David Novak 0:04 

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 Tobel, a financial services entrepreneur who founded two highly successful companies before she turned 40. In fact, she sold her first company learn vests 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 the show with me. I

Alexa von Tobel 1:43 

appreciate thank you so much, David. I'm honored and this can be a ton of fun. You know, Alexa,

David Novak 1:47 

you certainly do have an amazing story. And I'd like to go back to the beginning. Could you tell us about your upbringing?

Alexa von Tobel 1:53 

Sure. So a little known fact I was born in Kentucky.

David Novak 1:58 

Really? You know, I I'm from Louisville, Kentucky. No way. I mean, now we know okay, that's family. Yes.

Alexa von Tobel 2:06 

There's there's not many of us know, 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 I grew up with two older brothers. My parents, my dad was a pediatric specialists. 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 get I attribute a lot to being the youngest and to having two older 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 sets the tone for your life.

David Novak 2:55 

So your mom, your mom was a nurse, your dad's a doctor, what was it like growing up in a in a medical family?

Alexa von Tobel 3:03 

I always joke that I'm like, I don't know if I ever saw a doctor myself. When you have 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.

David Novak 3:56 

I talked at the top of the show, I talked about how every leader has to work through uncertainty and certainly you you had that very early on in your life as I understand it, your your father actually passed away when you were just 14 years old. How did that impact you know, how you lead the day when you when you reflect on it? So I

Alexa von Tobel 4:17 

mean, so much and I'm so glad you brought that up, David, you know, having something really unexpected happen and obviously losing a parent, as a child, it's your worst fear it truly is. And then when it comes through, you know, 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. i My way of healing was sort of seeking for the How does going through something like that help you and for me, you know, life is really precious and But I remind people this every day, which is this isn't the dress rehearsal, we only get to do this once. And that's it. And that 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, are we alive? Is the roof of our head? Do we food, something bad? Like it could be so much worse? And so I think that having that is almost in some ways, an existential strength. In you asked, how does that help me lead through ambiguity? Nothing's really that bad if you're 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 something bad, and we can keep going, and we can keep working. And we can prevail. That's

David Novak 6:00 

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 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?

Alexa von Tobel 6:21 

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 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, Avery, 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, my own oh my god, I David admire, I admire her so much. I'm truly blown away by the sort of things that she was able to do and keep all the trains 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 that has happened 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 data under 10%. But on the days where you get your the wind knocked down to you, it's okay, if you go home at four, there's just some, you know, we're human too. So the end of the thing is, you know, you 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 what she 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,

David Novak 8:38 

you only have so many assimilation points, you know, you can only take it so much and I think a leaders 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 don't

Alexa von Tobel 8:50 

you're allowed to go home and have a bad day that's allowed.

David Novak 8:53 

Yeah, you know, I I understand that and 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 how did you move from psychology to business?

Alexa von Tobel 9:14 

Yep. So I think my whole life David, I've always loved people you can ask, you know, my, my my whole family at five 710 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 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 in To the happiness lab at Harvard, which Dan Gilbert was was, was working on the science of happiness, and then I found myself in the mind brain behavior and positive psychology. And I just studied something that I loved in that. So 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 fulfilment, finding that deep self actualization. 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, 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 what what makes me tick. And so and it was I loved it, it was fascinating.

David Novak 10:52 

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.

Alexa von Tobel 11:03 

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 true, and we'll 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 punchline of that is 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 a great cup of coffee, or being married to somebody you 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 more things. It's not consumption. So it was a great orientation to be 18 to 21. And learning about those things. It I think it created a great foundation. Yeah, you get

David Novak 12:18 

that at early age, it 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 best and tell us about it? Yeah.

Alexa von Tobel 12:35 

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 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 stoop. 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 going and selling it my mom. No is the headline there. All that said, when I got to Harvard and graduated, I had this huge lightbulb 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 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 that love it. So the idea for learn best came from when I had graduated. I've been fortunate to get in Harvard Business School, I got great jobs on Wall Street, and you know, investment banking, and sales and trading 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 was quite capable of doing that. But she hadn't really done it. And I remember having this like really clear thought that said, I will be good at this. I 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 someone who's lucky enough to go to a great school and learn best was boring 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 if you did invest it. And I said, I'm going to go build that for modern people online for America, and, 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 in May of 2007. And I didn't drop out of Harvard business school until December 18 2008. So I was really percolating on it for a while there.

David Novak 15:25 

This is amazing, though. I think 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 out of Harvard, you had to have a million people tell you that you were crazy. How do you handle all the nose? It's,

Alexa von Tobel 15:49 

it's so funny. You're absolutely right. First of all, I had a million people 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 is in turmoil Lehman Brothers had gone under, it is a crazy time, don't go do that. And honestly, 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 ask 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, you know, 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, nine 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 thing, I felt fine. I said, it's time to work. Let's keep going.

David Novak 17:28 

Yeah, 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.

Alexa von Tobel 17:46 

So again, I keep it simple. I have written a business plan, David, that talked about the chapters of the business. And the first was we're gonna 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 disrupter. 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, you know, take one to 2% of your assets. And it was very expensive, you probably totally processed 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 sort of flipped the industry on its head, because rather than being available Monday through Friday, from nine to five, well said, we'll be available 24 hours a day, seven days a week. And we will only charge you for advice and sell no products. 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 in their 20s and 30s. who love to use the internet. But little by little we saw these people in their 40s and 50s and 60s and 70s. And all of a sudden I kind of had this moment I said wow, this product actually makes sense for everybody. And when I started we weren't even 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 like revolution of the wallet. That there were finally pure there were finally other people working in the category on the consumer wallet. And now kind of David you fast forward there's time and Robin Hood and all these amazing companies that are worth literally 10s of billions of dollars. And looking back, I was probably early to move. I mean, I was early, but it was, you know, some days I think about oh my god, what if I was running learn this today? I think it would be so much easier because zoom existed and all these other things,

David Novak 20:12 

you know. And you You did really simplify things. You know, I've heard, I've read where you said you demystified financial services, and you had the really terrific insight to help people focus on cashflow. Why

Alexa von Tobel 20:27 

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 gonna do this, I'm gonna do it right. And I'm gonna 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 used that in air quotes that was helping advise people with loads of money wasn't based on people's cash flow, 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 can help everyday people be able to afford month by month living. And then when they add extra teaching them how to have extra figuring out what to do with it.

David Novak 21:21 

Now you launch 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 Kool Aid Were you drinking,

Alexa von Tobel 21:40 

I will never forget it, I was on an elliptical machine at the gym, and I was studying for some tests, and Lehman Brothers is going under on the television. And I had three friends text me being like, I'm gonna 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 as the vehicle of that idea. But I that's kind of goes back to, you know, David, somebody wants this to me, and it like is burned into my DNA, which is when everybody's a gift is that 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 did 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,

David Novak 22:46 

you know what 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 vernacular. And I think this is really a great opportunity to give our listeners some practical wisdom here on this subject. If when you think back about it, you'd have not had to navigate through all this what people would describe as uncertainty, what would be three to five things that you could tell leaders to think about when when they're going through times like that.

Alexa von Tobel 23:19 

Well, so also, one other just quick, fun fact. So David, speaking of like navigating through uncertainty, I sold my business on March 25, 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 was 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 I was going through a life changing event, the most important life changing event in my whole life, which was 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. Tomorrow. 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 sized. 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 I've been described by many people in my life as hyper verbal, I am 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 what are the roadblocks, 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 just at least getting six to 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 gonna go exercise, like you have your mind is an important muscle that you have to take care of.

David Novak 26:38 

Absolutely. And you know, you describe yourself as a hyper communicator, you know, one of the things that I've already picked up is you're a very clear communicator, and you're able to simplify things. And, you know, you call learn this the Turbo Tax 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?

Alexa von Tobel 27:09 

I've never like done 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 until people. And it's so funny, David, I have a I have three children. My little, 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 too. And. 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 Tula 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.

David Novak 27:59 

You know, see your business takes off and learn investors 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, and to sell to Northwestern Mutual. And you mentioned all these FinTech companies that have multibillion dollar market caps. Any any regrets? It's, it's selling so soon.

Alexa von Tobel 28:24 

You know, this goes back to my I don't believe in regret. It's just like a really big waste of energy. So 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 a 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 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 interests of what we've 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 this this and they really called it a merger which was adorable because Northwestern Mutual is worth billions and trillions of dollars literally manages half a trillion dollars of assets and little learn best was this big. And the CEO is just the most spectacular man. His name's John schlocky, but I actually sent the video to the board and said I waited Still today to really process this. And it was actually a Northwestern Mutual Life Insurance policy that stabilize my own family after my dad had passed away. And I said to them, I know the power of what this brand does for family. And they have 8000 financial planners who go around the country to protect families for 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 a

David Novak 30:32 

cool, that's it's an emotional story.

Alexa von Tobel 30:34 

Yeah, it was, it was 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

David Novak 30:43 

to be so proud. I can tell you that it uh, you know, so you sell to Northwestern Mutual, is like you said his billion dollar company, you know, it. That had to be hard, though, going from running your own show to 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, from leading your own company and being part of a larger organization?

Alexa von Tobel 31:11 

So first of all, I mean, I really knew what I was getting myself into, you know, we spent a lot of time thinking about how do we come together. And again, we use 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 sort of like a marriage, if you've shared 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, you know, 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 gonna do it, I'm 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, uh, going from being the boss to being, you know, I was still CEO of learn 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, 1000s of employees, and literally budgets that span, you know, truly just massive amounts of money, they do almost 40 billion of revenue. And I'm just gonna learn everything like I'm a sponge, I was 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 cutie, he literally framed it. But as you would imagine, it was, there were moments of it that were beautiful, and so exciting, and some 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 you. I mean, that's like a punch line of integration. And so our commitment was just to this Northstar, we're gonna make sure that we build something better. And I'm really proud that that's where we are.

David Novak 33:41 

That's great. I love I love the fact that your husband framed that letter, which is meant so much to you, because that's, that was the goal you had when you set up. That's fantastic, you know? So how'd you end up founding inspire capital.

Alexa von Tobel 33:55 

So you kind of get a sense of how I think and operate. And when I was building learn best, I would dropped out of Harvard Business School 2425. 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, york city is the capital in my mind of the planet. It's just this incredible place of art history, culture, grit, stamina at Tech now, crypto, and I just had this deep moment that were 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 B and the most empathetic, loving, supportive mentor of mine. And he made me so Much better single handedly he was this one cumin who just constantly pushed me in. And it would send me the notes at 3am being like, I know you're not sleeping, I'm with you. I'm not 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've built a venture fund that is chock full of people who built companies before, who care about founders, not in this like arm's length way where you're like a cell in a spreadsheet, but like you really 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 always been in the back of my head. And then one day sitting there and it came out of my mouth, I was like, it's just inspired capital to capital that knows and understand 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, you know, instrumental now in putting people like President Biden back in the White House. And we have a deep, deep, deep, deep, deep shared history, lots in common. And we both lost parents, when we were younger, we both have two older brothers, we both very much had a similar orientation, and that truly forevers lover building businesses, and I called her and said, Hey, I'm thinking about this thing. And this idea 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 friend who had already transitioned to she co founded Paperless Post. And she studied psychology at Harvard with me. And we turned in our senior theses together and godparents of each other's children. And I, literally, she was my red phone every time I had like, a terrible problem that you can't solve. Because that's what being an entrepreneur is. And we basically I basically said, I'm thinking of building this thing. And she just, each night, I go over to her apartment and just sit there and talk about what it was and how I thought about it and got it out. And she's like, Oh, what if you did this? And what if you did this. And then when they looked at it, and I said, for you, it inspired capital, she was like, I'm that inspired. 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, and the last partners, this guy named Mark Batson, who had been with me for almost 12 years, and he and I were the deal, Team selling learn best, and I kept joking. If he wasn't sick of me, after working with me nine months pregnant, were nights and weekends, we would like do a second shift to sell the company and go through all of that, when I literally was like, 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 loved and trusted to it and 10 people in it was it 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.

David Novak 38:22 

You've got some great startups that you're 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. But based on your experience, what's the fastest way to get a no? And what would be the fastest way to get a yes?

Alexa von Tobel 38:41 

fastest way to get in? No. I'm going to give two short answers. One I 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's thought about something by the level of detail that gives you the answer your questions. So those are two pretty fast ways to get nose is to not have enough detail and to have it really feel like you're you're a voyeur at entrepreneurship. The fastest way to get a yes, it's not fast, it's your life's work. There's no way to hack, really caring about wanting to build something. And you now have a sense of my orientation David, like, learn best pour it out of my my value system. It was it was just, I got infected with it. And it was going to be over my dead body that I figured 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, but and those founders also they they do they speak in decades. They know that they want to build something and they understand 10 years and it will maybe or may not be on the path of In successful if you're building improperly

David Novak 40:02 

inspired capital, I can see why you bought that Dave immediately though it's so purpose driven. 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 really kind of, you know, gave you that spur you needed?

Alexa von Tobel 40:22 

Yes, I, as I've said many times, I've told her brothers, and it was amazing. They quite literally trained me. And, you know, my, my, my middle brother, his name is Brandon. He used to go running with me at like 11pm 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.

David Novak 40:54 

What was the line? What was the line, I can't make this up,

Alexa von Tobel 40:57 

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 are what? And 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 you know, 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, is, was just a really special athlete. His name's 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, cuz 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 in sweat bags and plastic bags, and just crazy stuff like that, David. But it would give me the confidence that I could be the fastest and be the best. And because both of them I'm sitting here today,

David Novak 42:22 

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?

Alexa von Tobel 42:31 

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 they've taken me six months of finding, interviewing six months of like, extremely focused work. And this person finally showed up, and within eight hours, I called my cell and said, I am not going to be able to stay. Something had happened. And I 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's truly just sick. And he is so cute. He drove and picked me up at the airport, which like 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 the 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 presented, they put you through a gauntlet and it basically by qualifying they meet they believe your idea is a big idea. And I stood up on the stage and presented in San Francisco on September 15 of 22,009. 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 gamification of money. That seems absolutely idiotic. And I just I 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, Robin Hood can't exist, time 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, 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 TechCrunch it was like getting TechCrunch they literally just tried to 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 is made it obvious. And even these big tech guys thought it was a terrible idea. And I just that was a that was a day that I'm now proud to relive

David Novak 45:14 

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. But 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?

Alexa von Tobel 45:43 

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 is this really wonderful, wonderful guy, his name is Cliff. And he is never, he will always tell me what I need to hear even when I don't want to hear it. And 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 dumb, that was wrong, don't do that. Or just, you're wrong, like, passionately, you're wrong. And so you can kind of get a sense of 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 not the senator of Arizona, but I, my husband, I became good friends with him. He taught me this amazing story about when his wife, Gabby Giffords needed surgery. He didn't 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 is 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 room set up properly so that you get to the right answer. That is

David Novak 47:31 

that is a great story. You know, Alexa, there's 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?

Alexa von Tobel 47:43 

Entered energetic, optimistic. And a believer. I'm a believer in entrepreneurship.

David Novak 47:50 

What's your superpower?

Alexa von Tobel 47:54 

My energy.

David Novak 47:56 

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?

Alexa von Tobel 48:03 

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 dumpster. And I don't have

David Novak 48:15 

one. Oh, no, you kind of remind me of the what is it? Black Widow or whatever. Where she does a little toes 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?

Alexa von Tobel 48:30 

I would love you know what, I would love to be one of my great grandmother's. And somebody I didn't really know and just get, you know, there why I'm here and people who paid for it 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.

David Novak 48:49 

What's your biggest pet peeve?

Alexa von Tobel 48:52 

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 patients every day. It is it is a meditation.

David Novak 49:01 

What's something about you that few people would know?

Alexa von Tobel 49:06 

I live for like, I I live for singing if my and I'm the least talented singer you've ever met in your life, just like not one ounce of talent. And my husband and I both like we would do anything to be able to be phenomenal singers because we just admire it so much.

David Novak 49:27 

Do you have any hidden talents? You're not a singer but you have a hidden talent? Yes, I

Alexa von Tobel 49:31 

can. I can whistle with my tongue alone. I mean, I have a bunch of random hidden talents. But no, I was a platform diver. I was an elite gymnast. I I can so I can cross stitch. I mean literally I've got a lot of random craft talents in my in my DNA.

David Novak 49:53 

What's the favorite thing you'd love to do in your spare time?

Alexa von Tobel 49:58 

I like to build things and And it really took me into the last few years that my favorite thing did my kids is sit and build anything I we can build Legos we can, we can build, you know, 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.

David Novak 50:15 

You know, I was really nervous election about doing this podcast with you because you're you're a phenomenal podcast or your own right, you know, with your founders project and partnership with Ink Magazine. You know, do you like doing the podcast,

Alexa von Tobel 50:29 

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 you know, I love doing it. And it's so fun to get to understand how somebody thinks,

David Novak 50:48 

yeah, I love that too. That's exactly exactly the case for me. Now, I gotta ask you this. Just a couple more questions here. Do you miss running a real business that sells something every single day? Is? Is there another startup in your future?

Alexa von Tobel 51:04 

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 year. So you

David Novak 51:28 

have these founders? Do you kind of view yourself as a CEO? And in the sense that you're invested in helping each of these founders build their business? And you're in it?

Alexa von Tobel 51:39 

Yeah, no, 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. And I very much feel like we're on the journey with them. And that's extremely authentic.

David Novak 51:57 

You know, I'm going to wrap it up here with this question. What's the one thing you tell any aspiring leader that they've got to have to be successful?

Alexa von Tobel 52:09 

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 we want, 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.

David Novak 52:46 

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 hear how you think and you're inspiring and inspire capital is that sounds like the perfect place for you to be.

Alexa von Tobel 53:04 

That's so kind of you, David, thank you so much. I've been a fan from afar for a long time. And just truly grateful that you have been honored to be here today. Thank you.

David Novak 53:20 

You know, when I listened to Alexa story, it reminded me of 2008 When I was a director of JPMorgan Chase. And when we had the financial crisis, where everybody thought the whole world was turning upside down, you want to talk about uncertainty. And 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 and action. Then I saw Jamie Dimon, 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? Will 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.