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Angel Investor (And NFL Hall of Famer) Joe Montana Scouts Y Combinator Startups (Q&A)

Joe Cool looks over the field at Demo Day.

Lauren Goode / Re/code

Joe Montana is known around the Bay Area for bringing home the hardware — the former NFL quarterback won four Super Bowl rings with the 49ers in the ’80s and ’90s. Now, Montana is looking to add new hardware to his collection — or software, depending on your startup’s business idea.

The NFL Hall of Famer was arguably the most famous attendee at Y Combinator’s semi-annual startup demo day Tuesday. Along with his wife, Montana is an active angel investor with equity in multiple YC startups from each class since 2012, although he’s still known more for his right arm than his business prowess.

That could change, of course, if recent bets on Y Combinator alums like CoreOS (open source operating systems) or flower delivery company BloomThat go the way of other YC legends like Airbnb or Dropbox.

Those kinds of success stories are what fuel an event like Demo Day, where 70-plus startups get two and a half minutes to wow a room full of potential investors. With a building full of nervous, eager entrepreneurs decked out in their startup T-shirts, Montana lived up to his nickname, “Joe Cool.”

“I want to see all the nervous people presenting today,” he said with a laugh, “because I know how that feels!” Like any good quarterback, Montana came prepared, arriving early with iPad in hand and a short list of potential investment opportunities.

Re/code caught up with Montana to talk investing, his history in tech and the shiny new 49ers stadium. What follows is a lightly edited transcript.

Re/code: What brings you to Y Combinator? Are you into the investment scene here?

Yeah, we started investing a few years ago through Ron Conway and SV Angel, and we still invest with him and started doing some things on our own. I think it’s exciting. It’s one of those things where it’s 50-50, maybe a little bit better chance that people are going to go, but you obviously see the excitement. Demo Day’s nuts. Meeting all the young companies, seeing where the future is going and what people are thinking about and the problems they’re trying to solve is always fun.

How often and for how long have you been investing?

We do a handful of investments in each of the YC’s [since 2012]. At some point hopefully we’ll be able to do more, but for now we’re just trying to learn all the ins and outs and just trying to not make too many mistakes. [Laughs]

I think our first [YC] class, we invested in three startups; now we’re doing about five or six. Hopefully as we get more comfortable with it, that’ll grow. You know, our accountant’s always going, “You know that’s extremely risky!” [Laughs] Yes we do, we do. We understand that part, but it’s also exciting because you get to see all the new ideas. Some are just fixing old problems, but that’s why you mix them around. I’m learning.

What are you most excited about?

We’re looking at a bunch of different things. From some bitcoin stuff on the edge, to some fun things like Backpack (peer-to-peer international shopping). We’re looking at some more traditional things like Unwind Me (on-demand massages).

In the sports world, you’re one of the most recognizable guys in the Bay Area. In the tech world, do you feel like you can fly under the radar at all?

Part of what makes it so exciting for me is when I first retired I got involved in a business with [former 49ers] Ronnie Lott and Harris Barton. It was a fund of funds in venture, leveraged buyout, hedge and real estate. I ended up leaving early because my boys were starting to play sports, but it was about $900 million under management. So I really enjoy the space.

I grew up with Doug Leone (Sequoia Capital VC) coaching my kids in baseball. I only knew Doug as a baseball coach, and went to my first meeting and he was there and I was like “there’s no way!” [Laughs] We’ve known a lot of the people in this space for a long period of time since I played here so that transition is a little bit easier.

What do you think of the new 49ers stadium? I know they’re trying to make it a very tech-friendly environment.

I think it’s a great idea to do that, I haven’t been in the stadium. Right now, I’ve been kind of crazy, doing [angel investing] right now, and I still have my son [Nick] playing at Tulane. At some point in time I’ve got to get that done.

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