Alexa Von Tobel is the founder of LearnVest. She dropped out of Harvard Business School to found the company in her early twenties, and the company was acquired for hundreds of millions of dollars in 2015 to Northwestern Mutual.


Alexa is now the managing partner at Inspired Capital. She is the author of Financially Fearless and most recently, her new book, Financially Forward.


On a personal note, when I was in my cubicle, flirting with the idea of potentially starting a business, wondering how I could do something different with my career… I was so lost.


I would sit at my desk at my 9-5 job with one earphone in and listen to YouTube videos of Alexa sharing her story of founding Learn Vest. She stunned me both with her mastery of her business’ focus (personal finance) AND her vision and perseverance as an entrepreneur.


It wasn’t long before I decided she was “who I wanted to be when I grow up.”

Tune into this episode to hear:

  • How Alexa found the courage to pivot away from (Harvard) Business School and venture out on her own.

  • Her advice about finding courage (this is a must hear!)

  • The “must-learns” about the future of finance and how to use it to get ahead NOW.

Hear from Alexa Von Tobel, founder of LearnVest and author of Financially Forward, about her journey to creating her multimillion dollar business.
Podcast Episode  

Transcript of Episode

Leah Gervais:

Hey visionaries. Welcome back to the your biggest vision show. I’m your host Lee Bay and I could not be more excited and I’m honored to have our guest today Alexa Von Tobel. Hi Alexa, thanks for being here.


Alexa Von Tobel:

Hi, good morning. So happy to be here.


Leah Gervais:

Alexa is the managing partner of Inspired Capitol a firm she founded just this year. She is the founder and former CEO of LearnVest and is the author of the New York Times bestseller, Financially Fearless. Alexa enrolled in Harvard business school and just a few months later, dropped out to found LearnVest in 2008, which was acquired by Northwestern mutual in 2015. Her new book Financially Forward will be released here shortly, at the time of this podcast this week. Alexa is a mother of what will be three when this airs. So thank you again, Alexa. As you know, I’ve looked up to you for years and I’m so excited to share your story today.


Alexa Von Tobel:

Thank you so much. I’m so happy to be here. Above all of those feats, I think the multiple children has been the most fun and the most effort, but that’s why they make kids so cute. They’re so cute.


Leah Gervais:

Oh yeah. You’re super woman. I can’t imagine. Okay. So my show is all about your vision and I know you’re such a visionary, you built a huge business when you were quite young and if you could just take us back a little bit to your childhood. Did you envision your life to turn out the way that it has? Did you know that you had this huge thing in store for you?


Alexa Von Tobel:

It’s so interesting you say that because I think we all have this like inner little voice, what we think we want our lives to be and obviously doesn’t always turn out precisely as what’s in your head. But I do think the more that we can kind of tap into, like, what is that voice in there? Are you supposed to be a dancer or chef or, you know, what is that vision? I always had a vision which was that I knew I wanted to… I loved business. I’ve always loved putting creative structures together and making customers happy. So, I kind of always knew I wanted to be a business person. I actually think CEO’s of companies are more exciting than like, you know, a big rock star or like a big pop star, like Brittany Spears or somebody like that. I would always be fascinated and so I think at some point, at a young age, maybe in my early teens, I kind of knew that I wanted to go do really unique things in business. I’m, you know, somebody who just loves to create and build and our latest venture inspired capital is just yet again, something I’m so excited to build and it’s really a home for the best entrepreneurs in the country to show up in and get help from people who love to build companies. I the punchline is I have no idea how life would ever unfold, but I always knew that I was going to put a lot of effort into doing something, hopefully exceptional in the business world.


Leah Gervais:

So yeah. So it sounds like you have the belief that everyone sort of has a big vision or sort of a voice inside them, leading them to something big. And for you that was business, but you think that, you know, most people do have something that really lights them up. I’ve heard you talk about that inner voice before when you’ve made really hard decisions. How do you get clear with that voice? Because if someone’s listening to this and they’re like, I don’t have that voice, where they’re like, I don’t know how I should follow this sort of gut feeling. Is there a way that you’ve over the years gotten better at following your gut?


Alexa Von Tobel:

That’s a good question. Such a good question. So I think that we all know what our gut says, I think sometimes we just don’t like what it says. So it’s not so much that my gut gets clear over time maybe. But I honestly think I’m just more brave to listen to it over time. What I mean by that is I think your gut kind of tells you. You know if you’re doing something you shouldn’t. You know if you’re hanging out with people that you shouldn’t. You know if you’re in a situation that doesn’t make sense for you. I think it just over time, actually by the way, a really fun fact is that listening to your gut, we always think it’s kind of this like very intuitive thing, but actually, apparently there’s like special nerve endings that run from your gut to your brain. So your gut really is meant to be one of the earliest places where the data that you’re collecting in your brain can begin to signal some sort of synthesis of an opinion. I read something a long time ago about that and that kind of made sense to me. Just a very early indication of some data that you’re computing. So I think the punchline is when I was in my late teens, early twenties, my gut would talk to me and often I didn’t like what it would say. It would be like, you know, go be bolder, go take this big risk. I often just didn’t totally feel like I had maybe the courage to do it or I didn’t want to do it. Or you know, when you’re dating somebody you know you shouldn’t be dating because you’re like, this isn’t working. And it’s saying hard things and I think just as I’ve gotten older, I’ve gotten better at saying, you know, what am I really thinking? And then just being like, you only get one life, so you’ve got to live it the way you want to. I even said to my husband last night about something else, I’m like, listen, we only live once, you know, let’s enjoy this thing. And this isn’t the dress rehearsal, this is your only shot and you get in life and you want to make as many good decisions that make you enjoy that life as humanly possible.


Leah Gervais: Amazing. I love all of that advice. I love that you share how the gut actually, you know, it’s not just an abstract theory. So it sounds to me like you feel like you’ve gotten a lot braver over the years, you’ve found a lot more courage to listen to that gut. And I love that it comes from this sort of, you only live once frame of mind, but someone that could be listening to this could think, well, you’ve built a multimillion dollar company before you’ve reached your mid thirties and so it’s “easy to be brave”, but you know that’s not the truth because this wasn’t always your reality when you started out, you didn’t have this track record, you didn’t have all these things going for you. So how did you stay brave when you didn’t really know that things were going to work out in those early days?


Alexa Von Tobel: Yeah, again, great question and for everyone just to quickly give some background. So I was born in Kentucky. I grew up in Jacksonville, Florida. My dad was a pediatrician, my mom was a nurse. Sort of normal, average family financially. My dad passed away when I was little, so I actually had a single mom raise me starting at age 14. So, and you know, working mom who was a nurse. So from 14 onwards, single parent and my mom has three kids. I did go to Harvard undergrad, which obviously is a place that gives you some confidence, it’s a great school. But then, you know, I ended up going and a starting business where I put all my savings into it and it was a big amount of savings for me. It was all my savings. At the end of the day, could my mom have helped me if something went really sideways? Sure. But I wasn’t about to let my mom help me. So, I basically just want to be clear that there wasn’t this picture of a bazillion golden parachutes that were around me that I could’ve jumped into. Right. Also, you know, when I dropped out of Harvard business school, it was December 18th of 2008 which was pretty much the lowest day of the worst recession in 81 years. I just knew if I was going to go make this bet, I had to go build this company at a time when America really needed to learn this financial planning software. Our whole strategy was how do we help make American families get access to a financial plan? So just punch-line: super scary time to start a company. I did not have an endless opportunity of things that could make my life easier. But  I really, really believed in myself. So, one thing I would just say to everybody, and I’m kind of noodling on this *not transcribable* right now, which is courage and bravery are free, like they really are. We all can have them. I love to think about advice I can give to people that everybody can have, right? Everybody can be positive and optimistic. Everybody. You may have to like trick your brain into being more optimistic if you’re naturally really cynical, but, you can figure out a way to be like, okay, rather than starting with the no’s today, I’m gonna start with the yes’s and why this could work. Or, I’m going to start with a better attitude and I’m gonna keep my negative thoughts to myself. So I love telling people like, attitude, it is truly a secret weapon. It’s an underrated skill set because everybody can do it. The other thing is bravery. You know, to your point, it’s easier to be brave when you have less risk. But then it’s really all relative, right? Because you know, maybe people who have other cushions, maybe they’re taking equivalent risk to where their situation is, right? But punchline, we can all be brave. It’s another debate where it’s like we can have the courage to stand up for people or say the right thing or take the bet or et cetera. I’m a big fan of calculated risk. So that’s the other thing I would say. I don’t believe in bravery, which is like jump off the cliff and have no idea what the heck you’re going. I’m a big fan of, and in particular when I left business school, you know, I had started Learnvest a year and a half before.


So I dropped out December 18th of 2008. I actually founded Learnvest May of 2007. So it was a full year and a half of effort. So I had a year and a half of early small data points that I knew I wanted to build this company. I’d wanted small business plans, so competition, which kind of indicated to me like somebody does not think I’m an idiot. We used one person to validate this to be a good idea. I started to collect just a few other people’s opinions and they said you could be onto something. So again, then I had a financial plan, a small little safety net to say, okay, if this goes sideways, what would I do? I started to figure those things out and I’d put some mini infrastructure in place. So that also when I no longer had a school or a job, because I was working for myself, day one, I had a little bit of a plan so that I wouldn’t freak out also so that I wouldn’t like go into panic mode of like, what did I just do to my life? And by the way, I still cried. And then I said, okay, well I have no other plan now, so I’ve got to get going to work. And I think that gives you a sense of like thoughtful, measured, calculated risks. Don’t just jump into traffic. That’s not a good plan. Having a thoughtful way to cross the street is what you need.


Leah Gervais: Beautiful advice. Thank you for sharing kind of you, where you grew up from, the things that happened to you when you were younger because I just think it’s so important for everyone to know that, that listens to you or anyone that looks up to you, that they most likely started where you are right now, if not even a little bit behind you. So you can do this. Like that’s just the message I always want to send to people is that they can do it if they start and that everyone that they’ve looked up to also started at zero, sometimes even less than that. So thank you for being honest with that. So I love that you talk about mindset and the mentality part of it and I think that that’s sort of like one of the most under talked about things in entrepreneurship and in entrepreneurial resources. And is there sort of a daily habit or anything that you do to keep your mindset strong and to keep you positive that you want to share?


Alexa Von Tobel: Yes. It’s called get up, dress up, show up. Literally, get up, dress up, show up. What does it mean? It’s literally my internal motto, which is get up early. You always just feel better if you’re not rolling out of bed at 9:30, but now I have little kids so the getting up early is at a whole new level. Dress up. What I mean by that is simply just putting on clothes that make you feel a little bit better. Just taking the time to do your hair, a little bit of makeup, whatever it is that makes you feel your best. It really does change your attitude. And then show up is show up with a positive attitude. One motto that I always had when I was going to Learnvest and now at Inspired Capital which is you have to bring 120% every day. When you get out of bed and when you show up to whatever the thing that you’re doing or committing your time and love and effort to, you’ve got to bring 120%. Sometimes I always say if your day’s going really badly, you can end early, but you got to show up with a full cup of positivity and attitude. I really just think people are attracted to people who are really positive. You can will more people into your vision and it’s just a really underestimated quality, which is just having an optimistic outlook.


Leah Gervais: And like you said- it’s free. That’s awesome. So you built a personal finance startup, you’ve built it very successfully. You learned everything you needed to know about personal finance and that brings us to today, your new book. I’d love to hear a little bit about how this is going to be a game changer for the digital world that we live in. If you want to share some of your favorite things or whatever you’d like to share about it.

Alexa Von Tobel:

Wonderful. So first I love this community and I think that it is precisely the community that I wrote this book for. So it’s called Financially Forward. It’s all about money is such a incredibly important tool for all of us. Money… I have always said I never strive to be rich. I just strive to never worry about money. I just don’t want money to be something that my family would worry about or stress about. Losing my dad when I was younger, I’ve just always said to myself, I just want money to be something that is not on the table in the everyday worry list. I think what’s really important about that for the book that I wrote, which is we are all super digital. We all stare at our phones for multiple hours a day and I am a very practical person who says, how do I make technology work for me? So, this book Financially Forward walks through one eight, the basics of a financial plan. So every single person in America, not even down the old, male, female, doesn’t matter. Income level doesn’t matter. This is a full financial plan of what you need to know in straight, in one place, in plain English. Then what we layered into it and what I did a lot of work to come up with every major tip that can just help make your life better. So everything from where to automate things, how many credit cards should you have? How do you think about your retirement savings in plain English as simply as you can. The best shopping hacks that’ll see truly thousands of dollars a year based on kind of what type of things you’re shopping for. How to just make sure that you keep more of your money in your own pocket so that it works for you. So kind of think of it as this super smart digital toolkit or you know, all of the best hacks to making the most of your money, for that really smart technology driven millennial, which we all are. So that’s the book. It comes out May 14th. I’m super proud. We have some really amazing people who have supported the book from some friends like Rachel Ray and Daphne Oz. To some really big names who just really think that the financial advice is what everybody in America needs. I wrote the book just to help people. I kind of did it in my free time because I really believe that if you can help give someone a good financial foundation, you can actually change your life.


Leah Gervais: I cannot wait to read it and for those of you listening we are going to be doing some giveaways of this book. I will have read it by then. So thank you for writing this Alexa. It seems more relevant than ever and I just think it’s going to be a hugely helpful book for our generation. So that sounds great. My final question for you is just anything, any last things people can look out for me for from you next? Or anything that you want to share about what’s coming up for you?


Alexa Von Tobel: Yeah. So first I would just say, for the audience, if you’re going to ask me three things that you need to do really well in your twenties.I would say three things. Number one, just believe in yourself. I think it’s an underrated quality. Just have confidence in your own ability and to listen yourself, to trust yourself. What’s really great, cause I’m now 35 which feels really old. By the time you get to your thirties, you kind of really know who you are and it feels amazing. You just really become settled in your traits and your qualities and so in your twenties just start to listen to that person because that person is pretty cool and you’re going to really like that person in your thirties if you don’t already. Maybe you know, you’re already there and that’s wonderful. Then number two, I would say is do not ignore your money. In your 20’s, if you simply, and again, you know, with the book Financially Forward that’s coming out. If  in your 20’s, you just simply pay close attention to the basics of money and money is not hard guys. I know it seems like a ton of math, it’s so simple. That’s what this book does I literally put it in plain English and maybe we’ll even do a live webinar and answer questions for you guys at some point if you guys want to have me back. But basically the takeaway there is don’t ignore your money. So if you wanted to do just two quick things in your 20’s one you would learn the basics, so that’s the book, buy it. Two, go ahead and contribute to a retirement savings in your 20’s. It’s not a topic for your thirties. The earlier you start the better. Then the third thing I would say is don’t feel like you have to figure out what you want to do with your life. Start figuring out what you don’t want to do. It’s actually easier to start shutting doors and saying, okay, I’m not interested in, you know, I don’t want to do real estate and I’m not interested in art and I’m not interested in cooking, but I really am interested in engineering and I want to go be an engineer, right?


So like start figuring out the things that you know you want to do, and start closing the doors on things you don’t want to do. Cause that’s almost an easier way to get to and I’ll kind of end on this… a really great mentor of mine said, the sooner you can figure out literally what you love to do, where you also have the skill sets to do it, the happier life will be. It’s so true, which is if you can figure out something that do have passion for and that gets you out of bed and where you have incredible skill sets to do it. So both, where you’re actually going to be good at it and you love it. That is like where you become alive in your career and you have so much fun doing work because you’re really good at it and it’s something that you’re really interested in. That takes a little bit of soul searching and a little bit of like listening to that inner voice and also listening to other people giving you feedback. But those are the things that end on that I think everybody should just begin to think about and get better at.


Leah Gervais: Amazing. I love the tip on shedding away things that aren’t part… that just circles back to this show about your vision is if you don’t know what your vision is, that’s okay. You can with what it’s not. So I love that you shared that and thank you. It’s such good advice. Well, thank you so, so much, Alexa. It was wonderful talking to you. I’m very excited to read your book and I’m sure others will be too. We’d love to have you back at some point and we wish you a lot of congratulations with your new baby.


Alexa Von Tobel: Thank you so much. I appreciate it. Best of luck to everybody. So honored to be here and I absolutely love your community.
Leah Gervais: Aw, thanks Alexa. All right, we’ll talk to you soon. Thanks, visionaries.

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