One of the most important achievements for an entrepreneur is learning to take on risk. Our next guest, Stephen Taylor is a general manager for Lyft’s Mid-Atlantic division, but his current position hides a non-traditional style and background.

ABERMAN: So Steven, draw an analogy for me. I understand that you started out as an naval aviator, landing in the middle of the night on aircraft carriers. How did that prepare you to become an entrepreneur?

TAYLOR: Good question! So, I went to college at the United States Naval Academy, and upon graduation, I was selected for the naval flight program, spent two years in the pipeline learning to become a naval flight officer. Then, I spent three years in Japan, flying E-2 Hawkeyes there. I was in Iraq in 2003. I think that the biggest parallels you can draw are the ability to make decisions in the absence of perfect information, the ability to lead people, not through intimidation. A common misnomer is, in the military, you can’t just tell people what to do, you really truly have to inspire a very diverse group of people around a mission, and convince them that this is something that needs to be done.

And that’s really important in entrepreneurship as well. And I think thirdly, risk. Oftentimes, when you’re sent on a mission, whether it’s innately a high-risk mission or not, flying an airplane around an aircraft carrier in unfamiliar territory is always inherently dangerous, and risky, and I think not too dissimilar—maybe not life threatening risky, but not too dissimilar—from being a entrepreneur, or an intrapreneur at a large company. Taking risks, and not having a roadmap, or not having a clear precedent on what to do, not having a manager who tells you how to get something done, I think those are the parallels.

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ABERMAN: I’m going to go to your current gig in a moment, but, before we go there—knowing about your background, one of things that struck me was, you’ve been a entrepreneur, you were involved in starting businesses after you left the Navy, but you’ve also been an angel investor. How do you see the two work together? How does somebody who’s a entrepreneur become an angel investor, and what’s the difference?

TAYLOR: So, I went the other way around. I actually started investing as an angel before I got into entrepreneurship, and even prior to that I was doing intrapreneurship at a consulting firm I was working at, PricewaterhouseCoopers. I think, once you have the bug of entrepreneurship, once that’s inside of you, that burning desire to create something and not just maintain—I don’t think it matters where you enter that world. I think at PWC I was given an opportunity to create a new service offering around organizational resilience, which was something that I did in the military. So, I was able to create a service offering at the consulting firm I was at, and then, with angel investing, it was sort of a next step in that direction.

I was able to insert myself as an adviser, as a consultant, to a small startup company to help them grow in scale. And then, when I moved to my current position at Lyft, I was able to take a well-funded startup—and at the time, this was 2015, I was employee number 400, we were well funded, but still, not where we are today—and able to take something from nothing. I mean, I was the first operations hire here in the D.C. area. I didn’t have an office. I didn’t have a team. All I had was a little budget, and I was responsible for growing that. So, I think that was my path, that’s my narrative, but I think as an entrepreneur, or a want-to-be entrepreneur, you can enter at any stage along that spectrum.

ABERMAN: Many people, when I talk with them about entrepreneurship, associate entrepreneurship with being the first employee, or the second employee, in starting a business. You just told me you joined Lyft when it had 400 employees. Explain why, and how, joining a larger company can actually still be an entrepreneurial activity.

TAYLOR: Companies need to innovate. Companies don’t just grow by doing the same thing over and over again. They don’t just scale because more people are aware of them, more people are buying their products and services. Companies remain relevant and resilient through changing times and changing markets by innovating. And so, you can’t just have people at large companies doing the same thing over and over again. You need to bring in creative minds, people who are willing to take risks, as entrepreneurs are, and try new things. And you have to have leadership at the top that are open-minded and willing to experiment, and invest in the people and resources to make those innovative changes.

ABERMAN: But, they don’t just have to hire people that are entrepreneurial. I’m assuming that you have to do things structurally to give people the ability be entrepreneurial. What are some of the ways that Lyft helped you to the entrepreneurial in a large organization?

TAYLOR: I think that the number one thing is to encourage people to be entrepreneurial. You encourage people to take risks, to think outside the box, to think creatively, and not be afraid of failure. It’s a common theme among startups, or would-be entrepreneurs, to say, move fast and break things, or fail fast. Those are those are trite things to say, but they’re really hard from the leadership or management perspective, to tell your employees to do, and then not fault them for failing. So, at Lyft, we have a really strong culture that’s driven by our leadership team.

And so, when the boss, my manager, says we need we use an unlock, we need to get more drivers on the road, or more passengers, or increase awareness, or grow market share in your region, he’s encouraging me to try new things. Not everything that we’ve done here in the D.C. region has worked, and when things don’t work, we take those lessons learned, we share them internally, as badges of honor. Like, this is a bold move we took, it didn’t work, but now you don’t have to repeat the same mistake. And when things do work out, you’re given the same amount of praise. The amount of praise of, like, this works, this is great, lat’s replicate, let’s scale, and let’s continue making big bets.

ABERMAN: At the end of the day, you can’t just not penalize people for failing, you also have to reward them for success. You compensate them, you promote them, pat them on the back. You touched on culture. It would seem to me that, particularly in the ridesharing industry right now, we’re seeing a lot of opportunity within it. But it appears to me when I look at Lyft that your company’s made a decision to have a particular type of culture, and have that be a business discriminator, right?

TAYLOR: Yeah. And this is not just in light of recent events. This has been part of who we are since the beginning. Lyft was founded in 2012, our mission was to connect communities. Our original motto was “your friend with a car.” We were the first on-demand peer-to-peer ridesharing service, and this understanding that it’s not a private driver that you’re getting to take you from A to B, you’re actually getting someone in your community. Your neighbor, your brother-in-law, your friend, your colleague, your coworker, to drive you. That’s really important, and foundational to what we are, and who we are. That’s also who we are as employees.

A lot of our first employees were drivers, a lot of the staff that I have on my team now are former drivers. I think that when you focus on community, and when you focus on inclusion, and you focus on diversity, I think you can accomplish really great things. It’s not just messaging. It’s true. I’ve been a part of the military, and nonprofits, and large firms, and startups. I don’t care what kind of organization you are, and what part of the country, leadership matters. Culture matters. They say culture eats strategy for breakfast.

ABERMAN: It really does. Well, Stephen, I really appreciate you coming on the show and telling us a little bit about your entrepreneurial journey. I assume it will be inspirational to many people who think that the only way to be an entrepreneur is to start something from scratch. Thanks for joining me.

TAYLOR: Thanks.

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