Alexa von Tobel: Founder of Learnvest & Inspired Capital

Episode 347

In this episode, Alexa von Tobel, Founder of Learnvest and Founder and Managing Partner of Inspired Capital shares some of her learnings from being an entrepreneur building and selling a successful startup. We learn all about her journey including her switch to investing in startups with her company Inspired Capital. She shares what she believes it takes to build the startup of the future and so much more! This is another inspiring episode that you won’t want to miss! On this episode of #TheKaraGoldinShow.

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Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be I want to be, you just want to make sure you will get knocked down. But just make sure you don’t get knocked down knocked out. So your only choice should be go focus on what you can control control control. Hi, everyone and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs, and really some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. Hi, everyone, it’s Kara Goldin from the Kara Goldin show. And I’m so thrilled to have my next guest. Here we have Alexa von Tobel, who is the founder of a company that you may be familiar with learn best, but she’s also the founder of an incredible, incredible new venture called inspired capital, which we’re going to get into. As I mentioned, she is the founder of learn vest, which was acquired by Northwestern Mutual and in 2015. It is, I believe, today one of the biggest FinTech acquisitions of the decade. And she went on then to found inspired capital out of New York, and it’s an early stage VC firm, which she is the managing partner of. And she’s also a New York Times bestselling author of the books financially fearless and financially forward, such an incredible human being as well. And fellow female entrepreneur that I am so thrilled to have on our podcast today. So without further ado, welcome, Alexa.

Alexa von Tobel 1:48
Hi, thank you so much for having me. Thrilled to be here.

Kara Goldin 1:52
Super excited to have you here. So let’s start a little bit at the beginning, I listened to another interview where you said you were a nonconformist. I loved that. And I’d love to hear a little bit more about Alexa growing up, like what did you think you were going to be doing? Did you think you were going to be an entrepreneur? Did you think you were going to be a VC?

Alexa von Tobel 2:13
Well, so a few things I grew up, I was born in Kentucky, and I grew up in Jacksonville, Florida. And I think from an early age, it was it was you know, I have always had a ton of energy. I’ve always been a builder. I’ve always been interested in building things. I was one of these kids who just always was up to something. And it really took until I got into college. When I really realized like, I’m an entrepreneur. That’s, that’s what I am. I’m an entrepreneur. At certain organizations, I’d started a tutoring organization. And I remember building businesses felt sort of natural for me even before I knew how to online but I was doing. So at a young age, the sort of things that like I actually said out loud I wanted to do, for example, in first grade, I told my librarian that I wanted to be the first female president of the country, which was an interesting thing that I deeply remember her saying. And, you know, later, I was really interested in medicine, my whole family is in medicine, everybody in my family minus means a doctor or nurse. And I was really interested in taking care of people. My name, Alexa literally means help our mankind it’s why Amazon picked it for the Alexa. And I think just the sort of value orientation my parents gave me Young was to take my God given talents and make the world better and help other people. And so I kind of knew I want to do something, help people. And then when I realized I could actually do that with entrepreneurship, just like my lights went on in my head, if that makes sense. So I think I always knew I was entrepreneurial. I just didn’t know how to actually describe it. And then, you know, so a lot of harebrained things as a child.

Kara Goldin 3:55
So funny, or was there an entrepreneur that kind of inspired you early on to say, like, wow, that sounds so cool. I’m gonna go and do that.

Alexa von Tobel 4:05
I mean, I just went member at an early age, you know, other people were interested in like pop stars and athletes, and I always was really interested in business leaders, like, who was the CEO of Hershey. And it just, it was like, an interesting way my brain worked, where that’s who I was fascinated by his people who were building big organizations. And that’s who I was fascinated by. So, you know, there wasn’t one entrepreneur that stood out, I will say I come from a very entrepreneurial family. My dad was an entrepreneur. His dad ran a lumberyard called the von Tobel. lumberyard, which is like a Home Depot of Indiana. I have other people that have been very entrepreneurial and my family, my brother’s an entrepreneur. So I don’t know if there’s something deep in that. But obviously, the underlying you know, I’d actually probably say that the entrepreneur that influenced me most was my dad who was an entrepreneur and I went to work with him ever Some are in some running his own business. And it just felt very comfortable to me to do this. Well, you

Kara Goldin 5:05
have an amazing journey. And obviously, you founded a company called learn fast, you want to just describe learn bass, like what it was like, how did you decide that this was something that needed to be launched in the market?

Alexa von Tobel 5:22
Sure. So it’s really simple and learn best was think TurboTax for financial planning. So in under 60 seconds, you can build a financial plan for any American family in that in, you know, of all income levels. So, very importantly, it wasn’t designed for the wealthy, learn best had a huge mission, which was that financial planning should not be a luxury product, it should be something that’s accessible to everybody. So that’s what we built TurboTax for financial planning got acquired by Northwestern Mutual. And my story of why I built it was really simple. I was Harvard undergrad, always had been very good at math, love math, growing up, really loved math, like nerdily very passionate, and realized pretty quickly, that I couldn’t believe I was graduating from from undergrad with zero education in personal finance. And there was got a big job, going to Wall Street. And I remember thinking, here I am, like, responsible and capable of helping make decisions with millions of dollars. Yet I couldn’t tell you what credit card I should have, what I could afford, and rent, practically, I didn’t know how to think about what my means were all these really critical decisions, pretty important choices, and literally had no idea how to get educated on them outside Googling them. And I just said, This is absurd. And so I was that passionate about going and building learn best. And I also lost my dad when I was younger. And my mom overnight became a single mom with three kids. And I remember having to think about our finances. And I remember being like, I’m always going to be good at my finances, because I never want to have a moment where I don’t fully have a command of how to be empowered in my own existence. And so that’s sort of why I decided to start learning maths. And then I wrote two books on the category as well that New York Times bestselling.

Kara Goldin 7:13
So was that your first like job? I mean, did you have a job prior to actually starting the company.

Alexa von Tobel 7:19
So I spend, I’d spend time at Insight Venture Partners in venture, again, back to like that early thirst for loving to look at startups and companies. And then I, my, my, I spend time at Morgan Stanley. And then I helped to build a company that got acquired by Facebook. And then I went back to Harvard Business School, so I had some other jobs. But I started learn bass nights and weekends, when I was 23. And so and then finally, I actually was one of these kids who I had a job I literally worked in my dad’s office, his medical practice, literally 1213 every summer. So I was one of these kids that like my parents took me to work. And I had a job and I add tours. And so I really worked my whole life. Interesting. So

Kara Goldin 8:06
looking back on those early days at Learn vest, did you have any idea what you were doing? I mean, were there a lot that you had this great idea. And I always tell people that ideas, obviously are so important, you want to find a solution, you think you have a solution, and you’re going to start a company, but there’s so many little things that come up along the way that you’re just like, whoa, like I had never thought I had to deal with employee benefits, things things along the way that are really, really critical and building a building a company. But did you feel like that, you know, you ever had these walls up that you didn’t know how you were going to ultimately be able to scale what you were doing? I mean, were there challenges along the way that you just thought, oh, my gosh, I just have to somehow get through this.

Alexa von Tobel 8:55
I mean, I would say that everything felt hard. And it’s why I just have so much empathy for every entrepreneur that Tolstoy said, I was completely grinning. I was brand new, I was trying to figure out I’d never been a CEO there. I was sort of first time founder at age 23. The business model was we were sort of, I mean, the FinTech was in a category of care, I literally went off and when we went to go start building it, the word FinTech had not been used. And so I was now navigating a regulated environment, we had become a registered investment advisor. So regulatory compliance from the get go, and then figuring out our business model, which is really clear mission which is let’s, let’s give everybody in America who wants it, even if their income is $50,000 access to a world class financial plan that you’ll get when you are worth millions of dollars. That that was the premise was simple, which is let’s bring that quality down to everybody. And how we would make that profitable That was probably a question that was one of those things where we were like, how do we make this work? And quickly, we started realizing we can charge for financial planning and we can bake in margin. And so it, we ended up figuring it out. But I always tell people, one of the best things about learn bass in the rearview mirror was that was actually ratably complicated and hard business. So I look for businesses that are a lot easier than learn best, you know, learn best turned out that had a very successful exit, and actually is now the core financial software for all of Northwestern Mutual, which is incredible thing. And it’s, I’m so proud of how they’re using the platform for millions and millions of families. But I ran a really far business. So yeah, I joke. There wasn’t ever a day where I was like, God, this is easy. Yeah, never once. And so I always joke I earned every wrinkle I have. Because I just there were there were very few things that were not complicated.

Kara Goldin 10:59
Yeah, but on the other hand, if it was so easy, there probably would have been a lot of other people who were, who were doing it, or who had done it before. You decided to start this too? Absolutely. Absolutely. Yeah. And I know that you were definitely I know how hard that business was, I mean, hence the company that I found it to also incredibly hard. The front end looks like it’s really easy. It’s like water and fruit. But there’s a lot in the process of actually making it that is very, very technologically, you know, a little bit more difficult. So I totally, totally understand that. So how did you get the word out about it? Here, you’re launching a product, what was kind of the first thing that you did to actually get the word out about learn best?

Alexa von Tobel 11:44
Well, so times were really different. Kara, this was December 18, of 2008, is when I officially went full time for learn bass. And, you know, when we started the business content, email newsletters were a new thing. Um, there’s a company called Daily candy at the time that had, you know, millions of followers. And remember, social media didn’t exist, there’s like all these do all these other things that didn’t exist yet. Facebook was relatively new. And so we started with content, we started with building a following and email newsletter that by the end had millions of people on it, where we can help people every day, learn a little bit more about their money, and built a brand really organically with content, we actually focus the brand early on women, because I was writing the content. And I became a certified financial planner and pass all the tests and said, If I’m going to do this, I got to do it all the way. And from there, we started very quickly launching our products off this email newsletter. And then the newsletter became the way that we stayed in touch with people. And from there then became a subscription service on our website and the beta mobile app, etc. But it all started from building a voice and a brand and a trusted place for people to manage their wallets.

Kara Goldin 13:02
So interesting. Do you think that your business would be built? If you were launching that business today? Do you think it’d be built the same way?

Alexa von Tobel 13:08
No, I mean, I think if it were built today, a few things would change first. Fintech is much easier to build. There’s so many more infrastructure layers, there’s so many things you can sit on. There’s so many things you can integrate with API’s you can use where we had to build so much ourselves, we had such heavy lifting. WordPress exists, you can sit on top of all these content players. So it’d be a lot cheaper to build a lot easier. The compliance and regulatory peace is so much clearer now. You’re one of the first sort of early digital regulated entities, RAS. And I’ll give you an example. And in compliance, like my book had to go through compliance. We were like, God, there’s got to be an easier way. Like how’s the book have to go through Tarek compliance arm. And the book was just the basics of money. So it just gives you a sense of know so many things about musea, which is now I run with my my co founders and partners inspire capital. And we’re an early stage venture fund focused on generalist categories here in New York. But with FinTech being a big category. You know, I love backing companies in the FinTech space today, because just so many things are so much easier.

Kara Goldin 14:28
Yeah, much, much more simple. So, although simple, but I would think that there’s still regulations around it that are more challenging than other categories, for sure.

Alexa von Tobel 14:39
Yes. It’s still more challenging because it’s regulated, correct? Yeah,

Kara Goldin 14:43
exactly. So you are obviously a founder you have your company inspired capital, where you’re seeing a ton of ideas. When do you know if a an idea should actually become a startup? And I’m sure you get lots of pitches. I’ve gotten lots of pitches myself where you’re in a you think that it’s not ready, right in some way. But what is it that makes you kind of think this is a great idea, but maybe it’s not ready to actually become a company or whatever? What is that gleam that you see that you make those decisions based on?

Alexa von Tobel 15:23
Sure, we ask ourselves this all the time, which is this idea of concept of feature or business, a long, scaling, durable business, and uninspired we like to back long scaling, durable businesses. And I think one of the things that you can get confused by is, wow, this is a really great idea, this is really interesting feature. That’s very different than this is a really great idea. This is a really unique and advantaged business that will create economic value. And that has a business model, that long term accrues value to it. So I’ll give you an example. We like to back businesses that as they get bigger, they get better, their advantage strengthens. That may be because they have a technical moat. That may be because they have an unfair data advantage. So you know, you think about AI, open AI today, you know, they’re certain you build an early chat and GTP, you get it out in the world, more people use it, the machine gets smarter, the machine gets better. And over time, your data advantage gets better. Those are the sort of things that we like to think about. And we really like to think about long term Moats. And then finally, you know, we are at our at our core finance experts, right, that’s one of the one of the things we are extremely good at. And so we also like to think about business models and unit economics. And is this a company that over time, the business model gets better. So those are things that should be businesses, big, long term, iconic businesses tend to have traits like that. Not all the time, by the way, that’s like, you know, there’s always exceptions. But that gives you like, a strong sense of of things that we look for.

Kara Goldin 17:10
Yeah, definitely. So you’ve hired a lot of people and built teams and scaled companies and sold them, and probably had to let some people go along the way, which is always really tough to let people go, I think it’s probably especially the first person that you’ve got to actually say, you’re fired, or, you know, your, this isn’t working out any suggestions, sort of knowing what you know about going through that process of not only recruiting but also, you know, figuring out that, that’s not going to help you to scale your company any further to keep that person on.

Alexa von Tobel 17:48
It was always really hard for me. In fact, it was with somebody that was on my management team for a decade, talking about this recently. And it was always really hard for me, I’ve at my core, I never got easier, but it never got better. Like, I had the words I had the skill sets, I had the tools, I knew what to say. But I never actually felt better about it. Because every time I was always so grateful anytime anyone joined our journey, or our platform or our mission, and I was so grateful for the trust that they were ultimately putting in me being leader. And anytime that that didn’t work out, i Those were the days where I didn’t get good sleep. So it is a skill set, though, that every entrepreneur has to get good at.

Kara Goldin 18:34
Yeah, definitely. And I think what I’ve learned along the way, too, is that there’s different stages of accompany to and sadly different skill sets and people that are needed along the way that I think people don’t really talk about when you know, they’re starting to build a company or hire people that, you know, they may not those people may not be there till the end, because there’s different things that really are needed for the company. So that was one thing that I really noticed along the way. So you’re a builder, like I’ve said a few times and a scalar. And you’ve launched a company from an idea to an acquisition, which is incredible. But building a team and continuing to up market fit, solve problems for consumers, raise money, billboards, you know, continue to have market fit, continue to build on the team. What are kind of the big landmines that you think are out there for entrepreneurs when they’re building? I mean, what where do you see things head south, for so many, that, you know, whether they’re friends or whether they’re people that you’ve read about or people that you’ve invested in along the way?

Alexa von Tobel 19:48
A few things. So first, I think the best founders have thought so deeply about their business that they are layer 678 Deep in topics and really Thinking about what they do. And I always gravitate toward founders who have put that level of thought into what they’re trying to do. Because once you turn the lights on and you start running, it’s really unfun. When you don’t know what your product market fit is, in, you don’t know where you’re going or who your customer is. And so when I like founders that tend to do a lot of that work upfront, incredible amounts of customer discovery, incredible amounts of market mapping, understanding their advantage, and why it’s a real advantage, etc. So it’s part one, things tend to go south when, you know, I think some of the best founders truly take feedback and it pretty beautiful and powerful way, and are constantly looking for people to give them tough feedback. So they can keep iterating towards the right place. And I think sensitive founder founders who, who are very defensive, that’s not helpful to being on that path. And so effectively, really great founders tend to have strong opinions, but are constantly pulling in data and information about how to get better. This environment, I think, one of the things that we’ve seen from Bounders, is you need to be extremely agile, this is a dynamic environment, the market went from basically zero interest rate to significantly increasing interest rates in a short period of time, which is the equivalent from completely changing the floor of the environment in urine, to black and white overnight. And I think the best founders, always keep one eye on the market and understanding what’s happening around them, so that they can have a good good sense of burn I what milestones are necessary. So places we often see people stumble is when they’re not forward thinking enough, they haven’t done the legwork on where they really want to go three years out five years out. People who don’t take enough feedback along the way to keep getting better. And then finally, you know, we’re in a dynamic environment. So very, very, very agile, strategically flexible entrepreneurs. That doesn’t mean you’re changing the plan every three months, it just means you’re constantly taking that micro feedback from what’s happening in the business into the budget and the KPIs on what you’re trying to achieve.

Kara Goldin 22:25
Definitely, I’ve talked to a bunch of founders over the last few months. And obviously, you just touched on this, but it’s it’s challenging, right, it’s challenging to go out and raise especially seed funds, you know, where you don’t, maybe your company doesn’t have a whole lot of traction quite yet. Any advice for people going out now, looking to launch their idea?

Alexa von Tobel 22:48
First of all, the internet is incredible. You can find out so much about everyone you’re going to talk to and pitch to and companies they’ve invested in, do your homework, I think it always comes off as extremely thoughtful, when entrepreneurs know the partnership and what companies you’ve invested in, etc. So that’s part one, part two, figure out a way to get connected into those people the best way that you possibly can. And, you know, I’m a, as I said, I’m literally from Jacksonville, Florida, you know, navigating New York City and California venture funds when I was 23. I knew nobody, but constantly figuring out who can make an intro who can help you out and like trying to do your best job and LinkedIn exists. So use it. I think founders who come in humble and thoughtful are wonderful. And you know, I think there was a big moment a pipe Cara, in the last few years where it was like, I’ve got term sheets and I’m moving and things are happening. I think just hype doesn’t work. You know, your best investors are just absolutely interested in substance, real businesses, founders who it’s their life’s work and want to come build for 1015 years, just like you know, hints been your life’s work, Kara. And I think entrepreneurs and I, you know, keep your feet on the ground. One motto I have is that there’s no shortcuts in life. When it comes to building an epically unique business, everyday matters, and every day is a day of hard work. And I look for founders kind of really do have their feet on the ground in that capacity.

Kara Goldin 24:24
Absolutely. Well, one last question. So best advice you’ve ever received?

Alexa von Tobel 24:31
Kara, I’ve received so much good advice, man to think about one but you know, I think you know, so much of my success has been the success of just so many people, dozens of people who’ve helped me from my family, my brothers, my mom, my mentors, and everybody has given me advice. It’s made my life better. I’ll give you two just quick things that I love which has been the world zigzag when the world runs one place, run run the other Don’t follow the pack. And a second piece of advice. And this is probably the advice I wish I gave my younger self, I finally started adopting this in my 20s. But you got to live your life for yourself. And you can’t care about what everybody else thinks. And the sooner you can get good at that, the better you’re going to be. Because the only voice that should be in your head are people that you love the people that love you back. And the, the more you can not care about what other people think, the better your life is going to be. And I think that if you’re going to do something bold and big, a lot of people are going to not agree with you. And you have to be okay with that. And so I actually think being contrarian and standing up on my own two feet, and ignoring the noise around me, has become one of my best skill sets. But I wish I had it when I was 17 and 16. It would have would have gotten in served me better. So that’s my one piece of advice.

Kara Goldin 26:01
Yeah, the longer your journey, I think definitely you look back and you think, Gosh, I wish I would have had this confidence, this knowledge, for sure. And and, and definitely knew what you knew today back then. So I love that. So Alexa, thank you so much for coming on. We’re going to have all of the info on you and also inspired capital in the show notes. But I appreciate you and appreciate you sharing all of your lessons and and journey along the way. And thanks, everybody for listening.

Alexa von Tobel 26:37
Thanks so much, Kara. You’re amazing. I appreciate it.

Kara Goldin 26:40
Thanks again for listening to the Kara Goldin show. If you would, please give us a review. And feel free to share this podcast with others who would benefit and of course, feel free to subscribe so you don’t miss a single episode of our podcast. Just a reminder that I can be found on all platforms at Kara Goldin. And if you want to hear more about my journey, I hope you will have a listen or pick up a copy of my book undaunted, which I share my journey, including founding and building hint. We are here every Monday, Wednesday and Friday. And thanks everyone for listening. Have a great rest of the week. And good bye for now. Before we sign off, I want to talk to you about fear. People like to talk about fearless leaders. But achieving big goals isn’t about fearlessness. Successful leaders recognize their fears and decide to deal with them head on in order to move forward. This is where my new book undaunted comes in. This book is designed for anyone who wants to succeed in the face of fear, overcome doubts and live a little undaunted. Order your copy today at undaunted, the and learn how to look your doubts and doubters in the eye and achieve your dreams. For a limited time. You’ll also receive a free case of hint water. Do you have a question for me or want to nominate an innovator to spotlight send me a tweet at Kara Goldin and let me know. And if you liked what you heard, please leave me a review on Apple podcasts. You can also follow along with me on Facebook, Instagram, Twitter and LinkedIn at Kara Goldin. Thanks for listening