Angel investor & founder: Maia Bittner

Published

October 10, 2024

We're happy to finally be sharing one of our favorite angel investor interviews - featuring Maia Bittner!

Maia is a total rockstar when it comes to helping out founders, her unique view of the world has led her on an incredibly coloful journey as an angel investor and an entrepreneur.

In this interview, we discuss with Maia how she started angel investing, her journey from founders to investor, and how that's changed her relationship with people.

Highlights:

Maia was a VC scout for Sequoia
Her relationship with founders has changed since she’s become an investor
Maia is an investment partner at XFactor Ventures
She co-founded Rocksbox and Pinch

What inspired your first angel investment?

I co-founded Rocksbox and when you found a company, other founders naturally reach out to you to get advice or talk about what they want to do. I was doing a lot of coffee chats with people and giving them advice and trying to build their companies. Through these coffee chats, Sequoia invited me to be a scout for them, which was great because at that point in my career I didn't have any money.

I barely had enough money to pay my rent, and I lived in a dining room and shared a two-bedroom apartment in San Francisco with six other people. So I wasn't exactly what you think of as somebody who can be angel investing. But that's kind of how I got started, with Sequoia, and it was really helpful.

Do people now see you more as an investor rather than as a fellow founder?

Yes, it kind of changes your relationship a bit because there's a bit of formality in asking someone to invest.

Now you're an investor in their company, and they're worried. Maybe they're worried about impressing you or they're trying to hide things, and so there's downsides to it as well.

I have a reputation as an investor and people explicitly reach out to me asking to pitch.

It's much worse to be pitched by lots of different people than to have people who think I did similar things to them and reach out to get my advice because they genuinely respect me and they're trying to build a big business and use all the resources available.

It also means that most of the meetings I take, I end the meeting saying “no, I don't think this is a good fit for me as an investor.” I'm so bullish on entrepreneurship in general.

I want to encourage so many people and it sucks that now almost every meeting I have with an entrepreneur, I end it with a no. Almost like “best of luck, but I'm not going to be a part of your journey.”

Did you get any benefits from being a founder and also angel investing? Did it help strengthen any relationships?

I think it did help me as a founder, not so much with relationships, but rather to keep going. Like I said, I really like entrepreneurship. I really like meeting people and stuff like that. It gives me energy to talk to new people who are fundraising.

They are so jazzed up and they're so energetic. I like fundraising myself. I think I'm pretty good at it. But the person I am when I'm fundraising, I'm not that person 100% of the time as a founder, most of the time as a founder, I think it's kind of a slog. Most of the work you're doing is work that is much lower level than any employer would pay you to do, right? It's like you do everything from the ground up and you're coming up with it from scratch.

It's easy to get pretty demoralized as a founder and so meeting with jazzed up early stage entrepreneurs who are so confident that their business is going to be big and successful, it gave me energy to go back to my business and keep pushing it forward.

What’s the most important factor for you when deciding to write a check?

Sometimes it feels a little bit like playing a board game, right? There's all these different factors you need to pull and there's all these rules. Do I like the founder? How big is the market?

But similar to board games, when you're evaluating an investment, you're necessarily taking a pretty simplified view of it.

I don't know all the problems with an industry. I don't know all the nuances. But sometimes that ignorance is also helpful. One of my best performing investments did a massive pivot one month after I invested.

It was one of the few non fintech companies I invested in and it ended up pivoting to become a fintech company, which is pretty funny. I think having that high level view is risky because that means you don't understand why an investment may or may not be successful.

You’re making your decisions based on the founders, who they are, how they're approaching the problems, how they think about the space and the opportunity, and how they're chasing it.

Even if the market and the product and all that changes, what doesn’t change is how the founder approaches it. In that sense, I think it's okay that I don't necessarily deeply understand the market of every investment that I make because I'm looking at how the founder approaches it right now.

I do evaluate the market, but only more as a reflection of the founder than because I'm dead set on the success of a company building in that exact market space.

What was your experience like being a VC scout for Sequoia?

You can choose to make investments and Sequoia backs those out of a separate fund that they have. I think the name implies a lot of collaboration with Sequoia and them sort of teaching you how to evaluate deals and stuff like that.

It's not really like that though, you kind of make decisions on your own and so it’s really like being an investor. One of the resources that Sequoia provided that was awesome was that their lawyers review all of the deal documents. I wasn't very interested in that at the beginning, but it was very cool and I learned a ton about evaluating term sheets and evaluating documents.

The lawyers would review things and they usually said something like, “hey Maya, this is a standard safe note downloaded off of YC's website. They removed the MFN clause. Here's the implications of that in the following three situations.”

It was so valuable to get their take and understanding of the terms of a deal and how it might play out in different situations. Since then, I've read some books that are also really helpful. The deals of a term can really screw you in a way that makes the investment not worth the risk.

Two angel investments that you're proud of?

I'm proud of my Pretzel investment, which went to zero somewhat recently, but still proud of it. And Show Drop, which is really cool. What they're doing is vending machines that do sampling so you can get a free sample by giving them your email address, and then the brands that you sample get to retarget you over email. I think it's cool because I love stuff that encourages entrepreneurship.

I feel this is tackling a big problem with D2C brands today, which is how to get distribution and how to get brand awareness in a really different way.

Anything that you could have invested in and you didn't, but that you now wish you had?

Athena - it does compliance training, I wish I had invested in them. There's another company called Pogo that does surveys, and I think my biggest one is Unit 21. I talked to the founder right when she was getting started and gave her some advice. I love female founders doing really deeply technical stuff. So I talked to her founder friend and gave her advice and I thought “should I try to invest in this?,” but I didn't.

BlockFi is another one I wished for a long time I had invested in, although now it’s gone to zero, which goes to show you never know who your winners really are until the very end.

What do you take pride in with regards to your identity as an investor?

I tweet a lot of advice and promote my portfolio companies, and I'm very good at helping people in the very early days of founding a company to find their path through the forest.

Like I said, it's so big and so unstructured and it's literally asking “what are we going to do today?” You wake up at 07:00 a.m. and you shower and you're going to go to work as a founder. What are you going to do? I think that I am very good at helping people figure that out and be efficient at choosing the right things.

Another thing is recruiting, which has been surprising to me. But I get a lot of people coming to me saying they want to join a startup, and so I get to funnel those to my portfolio companies.

I also like to riff on product strategy and stuff like that. I don't actually think that's necessarily that helpful but it’s fun.

Any angel investors that inspire you?

One is Nicole Wischoff. I feel like she's similar to me. She’s just a straight shooter, and she's crushing it. I love the way she evaluates deals. She's great and I really admire her.

The second one is Heston Burkeman. He was an angel and a VC for a long time. We really like the same types of founders, and I really look up to him, he’s excellent at maintaining relationships with people, and I think that benefits him a lot.