"You'll Never Regret That You Tried": Paul Bragiel on Taking the First Step

In this interview, Paul Bragiel, Founder of Golden Gate Ventures and an early investor and advisory board member at Uber, traces his path from selling his first game company to Capcom at 21, through a failed social network startup, to 13 years of investing in founders like Uber's Travis Kalanick. He explains why he believes execution matters more than ideas, why founders should fail with honor and transparency, and why taking risks costs the least when you're young.

Hi, everybody. My name is Paul Bragiel, an engineer turned founder turned venture capitalist. In general, I like to work with and get involved with cool companies around the world, especially really interesting entrepreneurs. We've invested in companies like Zappos and Unity.

What I'm really well known for, probably here in Silicon Valley, is that I was an early investor and advisory board member at Uber. I joined the company when it had fewer than ten people working there. The valuation was puny, so it was an amazing exit, and seeing that company rise has been one of the highlights of my career. In terms of multiples, it's over 2,000x, so things have gone pretty well there, right? It was a small check, but still life-changing. 2,000x is pretty ridiculous.

I built three companies, two of which were in Silicon Valley, and I sold two of those companies. For the last 13 years, I've been investing in young startups. In general, my thesis is to invest in companies started by really interesting and amazing entrepreneurs.

I graduated from school in 1999, so 24 years ago. I was playing games when I was quite young, but I got really into programming and tech in 1994. That's when I first started doing my early programming.

When I started my first company, there was no word for startup, no word "entrepreneur," no word "entrepreneurship." That word didn't exist yet, right? That's just how old I am, sadly. But people knew what I was doing because it's pretty simple. I was able to explain to them, like, "Hey, I'm pursuing a dream." "I played games. I'm an engineer." I had a couple of other friends, artists and other programmers, and we wanted to make a game, right?

People at first thought, "This is dumb and insane." My mom was really disappointed. She said, "Paul, you graduated one of the top two universities in America for engineering, why are you not getting a job?" And I said, "Well, I can make more money," right? People were a bit confused or surprised that I needed to get a really high-paying job.

About nine months later, I remember we signed our first contract. I signed a really big deal with a Japanese company called Capcom, you might know Capcom, they made a game called Street Fighter, and they decided to publish one of my games. I was 21 years old, and I made more money than my parents made in two years.

People very quickly changed their tune, like, okay, he might know what he's doing, right? Initially, people were sad or confused because entrepreneurship and startups weren't a thing. That has obviously changed in the last 25 years. Now it's a really hot thing, but it was a crazy idea when I started doing that type of stuff.

I'm not the most eloquent person. I like to get to the point. First, don't overthink things. Like, I told you with all my adventures, if you overthink things, you will usually talk yourself out of it, right? But once you take that first step, the second or third step is much easier, right? There are always hard steps and big hills and mountains along the way, but once you start going, the hardest part is just starting. It's really simple, but it's the hardest thing to do, a lot of times.

I don't know why; for me, it's not that hard. But I know a lot of people have that issue, right? I think it's a combination of things. It's really hard to get started because, one, you're comfortable in life; you have a nice job, right? Or two, your parents or family say don't do that, right?

Or it's really hard to start because it seems scary, right? All these things are out there, but the reality is that's all bullshit, right? It doesn't really matter what other people think or how hard it is; it's what makes you excited, right? Starting should not be so hard; it's just all these outside factors, society, culture, and family that change our minds, right? I think the biggest thing that holds most talented people back is other people giving them bad advice.

So my advice is, don't listen to them; just get started. If you want to do something, if you're dreaming about something, do that. Because otherwise, if you don't, you'll regret it. You'll look back in 10, 20, 30 years and think, I wish I'd tried. Just try. Worst comes to worst, you fail; at least you tried. You'll never, ever regret that you tried.

If you're younger, take the time where you're at your parents' house, and it's really cheap to live, right? You don't have much cost. Build stuff. Just start tinkering, start creating things, get your friends together. Because you're able to test a lot of things, you're also able to test working with people in a low-risk environment.

When you get to 30 or 40, you might have a girlfriend, wife, kids, mortgages, whatever. It becomes harder, right? I'm not saying it's impossible. But when you're young, you're 17, 18, 22, what happens? What's the worst thing? You fail. You move back home with your parents, right? Just take the risk; you have almost nothing to lose when you're young.

With my first company, I was on top of the world. I sold it and made money, and I was super young. The second company was a little bit different. We were trying to build something way bigger. The game stuff was big, and we sold hundreds of thousands of copies. We had some really big projects, but still, we had other people, like publishers, around us.

This product, we were trying to build one of the first social networks. The game industry already existed, even though the games we made were original, but with our second company we tried to build a brand-new industry. The idea in 2004: what is a social network? That didn't exist. Facebook didn't exist. Myspace, we all started within a couple of months of each other.

The company failed for a couple of reasons. One, it was a brand-new industry, which was very hard. Two, if I look back at myself, honestly, maybe I was a bit cocky. I had done so well with my first company, so maybe I thought everything I touched was gold, maybe that. The third, we just missed the timing on some things; it was a very competitive game, and only one winner would happen.

It wasn't like there'd be ten winners in that space; either one person won, aka Facebook, and everyone else died. While we did well, we had millions of users, we raised money, we had awesome engineers, the team was great! We just didn't win. I learned a lot from that. I got punched in the face a bit, but it was a good learning lesson, and I was able to take all those things and apply them to my third company.

Failing sucked, right? After my first company doing so well, the reason it sucked, obviously one, it sucked because I want to win, I'm a very competitive person. And two, it sucked because I had a whole team of people relying on me to raise more money or lead the company. And when I had to let go of people, or when we didn't get money, I remember there were days I cried into the pillow.

I was like, "Fuck, I have to fail. I have to fire a bunch of people today," or "My God, how am I going to pay the rent and the bills for the team next month," right? There have been a lot of stressful times, but you get through them.

What was really amazing is that while we did fail, we had people who stuck around all the way till the end. We had a bunch of people who stayed even after I ran out of money for many months, and I love those people; they're part of my family nowadays. But it was rough. Admitting defeat in anything sucks, especially when you're a very competitive person. But you sit down, let it breathe a bit, take back what you learned, and move forward. You don't give up; you keep on pushing.

This is important when you're a founder. There are ways of losing your credibility, right? But failing isn't one of them; failing happens. We all fail.

The key thing is one: how did you fail? Did you fail with honor? Did you fail with transparency? Did you fail because you tried a million things that didn't work out, versus some people, they fail because they give up, or they fail and they go quiet and disappear, right? That's not honorable. But if you go out there and say, I tried this, this, this, and okay, I didn't do this, this, this. 

For my team, I said, "We didn't pay ourselves a salary for almost six months. We did everything we could to save the company." All of our investors knew this. I was sending an update every month: this is how much money is left; this is what we're trying, please. And people know, hey, these kids did everything they could, but it didn't work out, right? So we didn't get blamed for that.

They're like, hey, these people are good people, and if they try something again, we want to back them. Now that I'm an investor, I look at the same thing, too. I know some of my companies are failing. Right now, there are companies failing. And some, they disappear. Those guys will never get my money again. But some people are telling me what's going on; they're trying this. "Hey, respect. I will potentially invest in your next company," right? So it's really important to fail with honor. I guess you could say.

Honestly, a lot of the companies we invest in, they're great founders but not known founders. A lot of times, people start out from very humble beginnings. Let's say companies like Unity and Uber, these are cases where I know the founders are ready.

The founder of Uber, Travis, was a friend of mine, and, funnily enough. When my second company was failing, his second company was failing too. He lived maybe 3 or 4 blocks away from here in San Francisco, so every week or two we'd get together, have a beer, and say, "Fuck, this sucks." We just became friends. Then when he started his next company, which was Uber, he said, "Hey Paul, I need some help hiring engineers." So at first I joined as an advisor, because I hadn't even sold my company yet, right?

So I came as an advisor, and later I put some money in. A lot of the best deals I got into is because I just knew the people. right? I was friendly with them, or a friend of a friend. Somebody's like, "Hey, you got to talk to Paul. He's an amazing investor." So for me, we usually don't have to fight to get the deal.

We get invited to come in because now I've been doing it for 13 years; we have a good reputation; we've been in tons of cool companies; people actually reach out to us and want our money. I very rarely have to beg to get into a deal; if I'm begging to get a deal, then maybe I'm doing something wrong. Most of my best deals, though, were with people who were not famous, or nobody wanted to give them money; I was just one of the few people who believed in them first.

That's something my brother and I take a lot of pride in; we like to be one of the first to check in. We like to be money in first, and then other people come after us, it helps start the ball rolling. That's really important to us.

I have not exited Uber fully. I've sold some along the way, I sold some about a year before the IPO at a $50 billion valuation. I sold some throughout the pandemic, offloading to diversify my portfolio. But I still own about, I think, 30 or 40% of the shares I had originally 13 years ago. One big belief that my brother and I have is that we're super long-term investors: we like a company, we like the founders, we like the team, and we stick with them as long as possible, even post-IPO. Touched on this earlier, but some of the things I see in the best entrepreneurs: one, they're very persistent, and they don't give up.

Every company has hard times, so they know how to push through. And two, they're inspirational. When I say inspirational, it doesn't mean they're great at talking, like giving a speech from a balcony. No, some people inspire because they're very good engineers, and they inspire through the awesome code they made.

Some people are very inspirational because they're able to go out there and raise money really well. Or somebody is really inspirational because they're able to paint a very good vision and make a good design, right? The key thing is that the person is inspirational because they're able to go out there and attract other amazing people.

If you have those two skills, hard-working, never giving up, and inspirational, put those together, and it's a great foundation for an amazing entrepreneur. Everyone has an idea. Have you ever had that happen where you think of an idea, and two weeks later you hear somebody building it.

People coming together around the same ideas don't make it special. What makes it special is execution, the way you're building the company. Nobody wants your idea. You have to start building it yourself. No one's going to build the idea for you. You have to take ownership of your own ideas and build them. Ideas don't matter; it's the execution behind the idea that really matters. Bad execution is sloppy, behind schedule, and not hiring the right people for the right thing. I can give you tons of examples of people with bad execution.

Good execution means being on time, regimented, paying attention to detail, being frugal, and hiring people as needed, if at all. Put your head down, execute, and get through the hard times, and then it'll become easier. Also, when you start a company in a hard time, when it becomes an easy time, it's super easy. Right now, it's also easier to hire people, easier to go out and get resources.

Just put your head down, execute, don't complain. Be very, very efficient with your money, and you'll be fine.

Entrepreneurship is creating something out of nothing. You're manifesting something with limited resources; you're bringing magic to the planet. You're building something you've always wanted to see exist, and you make that happen. That's a beautiful thing. To go out there, have an idea, and bring it to reality, it's a beautiful, beautiful skill. I guess the key thing is, one, focus on humans, right? Always be curious about people. I'd say be curious in general.

What's cool about VC is you're paid to learn new stuff. Or you're paid to invest alongside people who are going to create or disrupt industries. Stay curious, stay humble. And what I mean by humble is don't put yourself above people, just be nice to people. I think everything else comes afterward.

As long as you're very curious, you're nice to people, and I'd say also hardworking, if you have two of those three, or all three skill sets, you'll do pretty well. But you have to listen, you have to understand, you have to absorb information and process it, and make decisions based upon that.