From napkin notes to term sheets: A chat with Inspired Capital’s Alexa von Tobel

The next iteration of fintech is upon us, according to Inspired Capital’s Alexa von Tobel.

“Fintech 1.0 was very much, ‘Let’s take what already exists and let’s do it better,’” she said in a recent appearance on Extra Crunch Live. Consumers are shifting away from Chase Bank and migrating to no-fee trading platforms like Robinhood; instead of booking an appointment with a tax advisor, people are registering with TurboTax.

Von Tobel, who founded financial-planning service LearnVest before joining Inspired Capital, said fintech’s future involves bringing infrastructure and support into ecosystems created by services like Robinhood and Betterment. It’s one of the many sectors that her generalist firm, which closed a $200 million debut fund last year, is interested in.

Our hour-long chat included tips on how (and when) to pitch her, breaking into VC and using vulnerability as a competitive advantage. Don’t just take it from us: Watch or listen to the entire conversation after the jump, or read some of the highlights below.

Should founders reach out to venture capitalists before they have a product to show?

At Inspired Capital, we do seed and Series A. We are literally the first money in on the napkin. and [we look for] a founder who has done everything in their power to articulate [their] vision. That may be a deck. In my case with LearnVest — and again, nobody should do this, it is the silliest thing I ever did — I wrote a 75-page business plan. Nobody read it. But it was for me and it just got everything on paper. It was almost like my thesis statement on income in America and how do we help everyone’s wallet and the evolving wallet of the American population?

Again, super nerdy, really boring, but I had it and I think it’s those sort of assets, a deck that walks you through it, literally a 20-page screenshot that you’ve drawn of what your vision is … maybe be more like Jeff Bezos. The Amazon way is only five to six pages, but I wrote 75 and it was just because I was getting it out of my head. Do everything in your power to say, “This is what my vision is.” Because you want to bring somebody into the boat with you. You help them see where you want to go in whatever form you can articulate.

If you’re a designer, do it in Figma, if you’re an engineer, build the quick prototype. If you’re a business-oriented founder, draw it out and write it out, whatever it may be. But I’m looking for somebody to use their communication skills to show me where they want to go and why they’re gonna win.

The future of restaurant and hotel tech

Six months ago, we were thinking about restaurant tech and we are deep in restaurant tech. We are super interested in anybody out there. Because let’s think about it, restaurants are here to stay. At some point, nobody wants to do my cooking anymore because it is so bad, including my own kids.

We’re always going to want good, healthy, quality food that is safe, efficient and affordable. There’ll be different versions of how we want to eat. A restaurant owner is an entrepreneur and they need better tools to be able to do [their job]. So we’ve thought a lot about that. The categories that are getting pummeled are the categories we also want to spend more time thinking about. Nothing is off limits and there’s no such thing as like an out-of-vogue category either. You know, I think we’re looking for killer entrepreneurs and a killer entrepreneur will find its way to value, almost no matter what.

Her tips for breaking into VC

I actually did a stint at Insight Venture Partners and I helped build a company that ended up getting acquired by Facebook. Then I dropped out of business school to build LearnVest. Then I was actually responsible for running a venture fund at the company that acquired LearnVest, Northwestern Mutual, and I was doing a lot of active angel investing.

So my path to getting into [venture] was, I actually started on the investing side. It was really early and I was just obsessed with entrepreneurship. For everybody out there that wants to learn more first, feel free to just follow me on Instagram. I’m @Alexavontobel. You can DM me and I actually answer those all myself and so I’m happy to, you know, direct you to a book or direct you to some sort of good podcast.

I think you’ve just got to start … really developing your own points of view. What are the categories you love. You can’t boil the whole ocean. Inspired Capital is a generalist fund, but we all have topics we love and we’re also overnight learning.

What is the future going to look like now that COVID has happened? And we said, “Wow, what does the global health connected network look like? How do we go get really smart on that rapidly? And the future of the suburbs now that this has happened, what does that look like?”

You just have to have a learning mindset. So I would say find areas you love. Have a learning mindset. Find a few mentors. You’ll find people like me. I want to pay it forward. I want to help as many people as I can. There’s only 24 hours in a day, but I’m always willing to say, “Hey, do this, read this, know about this, check this out. Here’s a person you should be friends with.”

As a certified financial planner, I would not say start spraying your own money around before you can take care of the basics of your own bills and your credit card debt and savings and things like that. But I think there’s ways for you to get into the flow of the learning stream, get attached to a fund, become a scout. Then just remember, it’s a job where if you work really hard, and what I love about venture in some ways, you can have great results if you just outwork and really put your head down and have the vision before anybody else has it.