We are going to transform urban transportation," Robin Chase told Inc. in 2001, shortly after co-founding Zipcar, the car-sharing company that disrupted the auto rental business. Since then, Inc. has tracked the growth of a class of entrepreneurs who aren't white men as they spawned entire industries and busted glass ceilings. These five leaders joined us to discuss the unique and continuing hurdles facing women founders, and to share their passion for the opportunities that await those willing to discard the concept of failure.

In a conversation with Kris Frieswick.

I'm thrilled to be surrounded by so many people who invented entire industries. Kay, you came up with the model for original content on cable. How did you do that?

Kay Koplovitz: I worked in the satellite business. I worked in the cable business. I wrote a master's thesis on satellite technology in the late '60s, but we had to wait seven years to get approval to use satellites in our industry. I was a television producer during college. I put together the skills that I needed, but more important even than that, I worked to be introduced to and know, on a working basis, the key players in those industries. It was really important to know the people whom you had to know before you needed to do business with them.

Jennifer Hyman: I agree, especially in my industry, where we've had to persuade designers to sell us inventory, and have it be rented at the exact same time that it's sold at department stores. That's all based on relationships. There is no data that I was able to give them beforehand to say, "I'm not going to ruin your company." They had to trust me. They had to like me. The almost 300 designers we've brought on--every single one has been about lunches and dinners and drinks and relationships.

What was your pitch? What the heck did you say?

Hyman: That we were going to introduce the next generation of women to designer brands. I'd come from the travel industry, and I had seen that when a couple honeymoons at a specific hotel brand, loyalty explodes. People will tend to go back to that hotel every single year. So I thought, "What are the other moments in someone's life when you can create brand affinity?" The original pitch was, if we can get someone into Carolina Herrera at her bridal shower, she will take photographs, and those photographs will be up on Instagram and Twitter and Facebook. She will remember it forever, and many of those customers will end up converting.

Robin Chase: It reminds me of what I would say to the car manufacturers. I'd say to them that 40 percent of people sell or avoid buying a car upon becoming a Zipcar member, and then when they leave the service, 40 percent go on to buy a car. And which kind of car do they decide to buy? Well, clearly, ones that they've been driving with us, because they're always clean, well maintained, and never break down, because we're dealing with that. People are thinking, "These are fabulous cars."

Lexy, you started out as an artist. Why go from that to running a retail company?

Lexy Funk: It was the conflict of wanting to do art and wanting to be creative but having a very difficult time making a living. That was really the spirit that we put into Brooklyn Industries--which is, how can we form a design company that is also a corporation that is also a retailer that is also a place where we make things and sell things? But that can maintain an artistic spirit?

It sounds like you jumped from the frying pan into the fire when you went from art to entrepreneurship.

Funk: Somebody asked me when I was 8 what I wanted to do. I said I wanted to be an entrepreneur. It just sounded like a very nice long word. It sounded better than ballerina, which I wasn't very good at.

Hyman: I can't believe you knew that word when you were 8.

Funk: What I liked about being an entrepreneur is it's a lot of risk-taking, which I think is cool. I like the math aspect, and I like the people. I like the idea that you can build something that's alternative, that you can create your own culture, and that you don't have to be part of the system.

We have a lot of risk-takers in this group, but we keep hearing about how women are afraid of risk. What has been your experience?

Koplovitz: I want to push back a little bit about this idea that women don't want to take risks or women are afraid. Women aren't afraid. Women need to have an ecosystem that supports them. We've had women who are eight months pregnant come up and pitch at our [Springboard Enterprises] events. Women are excellent at taking the right risks, and when you look at how women entrepreneurs manage their capital, they are much more capital efficient. They make better choices. Maybe they don't make them as fast as some investors want to see them make them, but the track record is better in the long run, and the liquidity events are higher. We should start talking about this, rather than saying, "Oh, women are afraid." Women aren't afraid. They just need to have a pathway and understand what the challenges are.

Hyman: I personally hate the conversation that makes it feel like starting a business is this big scary thing. What is the risk of wasting your life doing something that you hate every single day? Failure is just part of the process, and we have to start teaching people that if they have a great idea and they go after it and it doesn't work, they just try something else. Get up and start over again.

Koplovitz: That is a big difference from 15 years ago. When we started Springboard back in Silicon Valley in 2000, that's something that we did have to teach women--that starting and trying is better than not starting at all. And now, I think that more women are beginning to understand that.

Hyman: The one thing that's really important, though, is, what will companies do to support women through life stages?

Caterina Fake: One thing I learned recently is that the better a company is in supporting women, the better it becomes in supporting men. My startup [Findery] is only 12 people, and we have our first person going out on maternity leave and a vice president's wife is also pregnant. We decided that it was really important for us to extend paternity benefits to men. It's very tough to do when you're a startup. You have very limited capital, you have very limited funds, but creating those kinds of things is important. It trickles down to benefiting the entire organization.

Chase: The real glass ceiling is at home. Until men are as completely confident and capable of taking care of children or aging parents as women are, that's what we need in order to have equality of numbers. And until that happens, we will continue to have women who, when forced to make a choice, will stay with family.

Hyman: I see these young women graduate from college, and they come to Rent the Runway, and they feel like they can have it all. Sometimes, I feel like the debate that's happening at the level of a Sheryl Sandberg or an Anne-Marie Slaughter is destroying the confidence of the younger generation. I don't necessarily feel like gender has been an impediment to me, or to women who are entrepreneurs of my age group who have had great ideas.

Chase: But it's a real issue. We women here today have a special über-bond with one another because we are women CEOs, a bond that we would not have with male CEOs. It's not that we're denigrating the male CEOs; it's that we have a special, faster bond. And white male VCs evaluate people with an eye to the special bond among their white maleness. One day, I was early to a meeting in a large venture fund office. I was sitting in the reception area. I was watching the interactions among the VCs who worked there and the receptionist, who was a woman.

All the VCs were male. The VCs were talking to one another in the reception area, saying, "Oh, did you go see this guy? Did you talk about that deal? Were you in that morning meeting? It was so great." The only interaction these men had with the woman receptionist was, "What's the bathroom code? What is for lunch?" and "Those are nice recycling bins you have going." As I sat there, I could feel palpably how the men are thinking that the women entrepreneurs coming in are just a little bit dumber, and they know a little bit less stuff. So it's clear to me, even though, Jennifer, you know smart women, I think that those men, working exclusively in their male VC world, think all the people they're talking to who are smart are men and primarily white men, with a few Indian and Asian men thrown in there.

Koplovitz: In the Springboard portfolio, two of our later-stage life-sciences companies raised all of their capital, in excess of $50 million, from family offices and individuals, because VCs did not even tune in to what they were doing and didn't believe they could do it. They're going to be big exits, and VCs will have no part. They didn't understand it.

Hyman: I think all the stats would confirm everything that Kay is saying. Fewer women get funded. Fewer women actually even ask for money to start out with, and of course the natural inclination is to fund and to hire people who are like you. That being said, it is so important for all people with any diversity whatsoever--whether women, African Americans, Latinos, anyone who just doesn't look like the standard--to keep on going to the door. There is going be bias and discrimination, but unless people are raising their hands and saying, "I'm here; listen to me," no one's going to listen.

Koplovitz: The VCs are going to start saying, "How did we miss that company? We are going to listen to more of these women." If they see that women are building big companies, they are going to come in with their money.

Switching gears, what would you say is the biggest challenge or obstacle you still face?

Fake: The companies that I have been building are innovative, cutting edge, new business models, and new ideas. Getting the money has been the largest roadblock, and persuading people that the vision I had for where the future is going is indeed where the future is going.

Hyman: I think my biggest obstacle has been learning how to lead a company while it's growing at more than 100 percent year over year.

Funk: Aside from the money, my challenge in being an entrepreneur is deciding if this is the right path versus being an artist. I don't want to go back to the starving artist days. But on the other hand, there's something about the freedom of that that I really miss.

Koplovitz: My biggest challenge is to narrow down the possibilities to things that can be executed and to find enough people who want to execute these things.

Fake: I have this issue as an investor, too. It's one of those "90 percent no, 10 percent yes" kinds of jobs, and it's a problem when you're an optimist. I say, "I see how this idea's going to be great, and there are huge possibilities behind this."

Koplovitz: We have the greatest time in the history of mankind, in terms of what's available to us today and the opportunities. I wake up every single day and I want to do them all.

To hear more from the conversation, watch the video below.