Inc. named Aereo, the broadcast TV subscription service, and viral-media startup Upworthy among our Most Audacious Companies this year, their bold navigation through the opportunities and perils of the media landscape being perfectly in tune with all we've celebrated throughout our 35 years. But those perils snagged Aereo founder Chet Kanojia in late June, when the Supreme Court KO'd the company's service. He joined us, along with Upworthy's Eli Pariser and Suroosh Alvi of the streetsmart Vice Media, to discuss his next moves--and much more.

In a conversation with Jon Fine.

Vice began 20 years ago as a free publication, the Voice of Montreal. What were your ambitions then, Suroosh?

Suroosh Alvi: We launched an English magazine in a city with a shrinking English market that already had two English-language weeklies. The economics did not make any sense whatsoever. I thought it would be a single issue, and I'd be able to say, "Hey, I did this." Or maybe this thing could be huge. We were on welfare and eating beans and rice for years, but we'd still joke, "We're gonna take over the world"--that us-versus-them global domination thing. But it was hard to visualize what that would look like.

Chet, you sold your ad-targeting firm, Navic Networks, to Microsoft [reportedly for $250 million]. Aereo didn't start like Vice.

Chet Kanojia: Suroosh is lucky. He's still doing what he started doing. If you end up selling a company, I think that's unsuccessful. People don't understand how much of a loss it is for the people who live and breathe it every day. The bank balance looks nice, but that feeling is fleeting. You get back to the angst of, I want to do something again. There were technical reasons for Aereo, but a lot of it was a personal reason: an unfinished story. One side benefit of an exit is people trust you and invest in your ideas. But I don't think any founder who really cares about what they started can say, "I'm glad I sold it."

"I don't think any founder who cares about what they started can say, "I'm glad I sold it."Chet Kanojia

Anyone with a new idea is told "you can't." Were you, Eli?

Eli Pariser: With us, it boiled down to, You can do meaningful media for a small audience or reality TV for lots of people, but there's no space in between. Our story was, there is space. Lots of people love to know about important topics but aren't well served by existing media. Most people said we were out of our minds.

Kanojia: Anytime you deal with an established industry, you gotta convince your talent to see the world completely differently. And it is easy to get distracted. There's always a shiny object--some deal with some major company that will take you down a different path.

Pariser: The hardest thing is maintaining your contrarian way. Because you hire great people from great organizations, and they say, "This is how we do it. These are the rules."

Alvi: We've had shiny objects placed in our path. But they can be positive. We ended up with cameras in our hands in 2007 because an executive at Viacom said, "If we gave you money to make a DVD, what would you do?" Had we not diversified, Vice would still be, like, eight people in a south Williamsburg loft.

"We were unemployable. We pretty much had to make this work.Suroosh Alvi

Pariser: Suroosh, I'm two years and change into my project. Across your 20 years, how did you learn what to change?

Alvi: It's only in the last five to 10 years that things became a little more strategic. Our first couple of years were not like yours, Eli. We were a couple million dollars in debt after we moved to New York [in 1999]. Only in the last year or two have we felt kind of comfortable, and not living with the fear of financial insecurity.

Pariser: So prepare for 18 years of hardship? [All laugh]

Alvi: Eli, did you plan to be where you are two years into it?

Pariser: No. There is a story line that's always like, We had this brilliant idea and through great determination and our own strength of will, we made it happen. But the reality of success is often about tapping into something much broader than your vision. When the thing that you're excited about meets history in a good way, you're able to get a lot of traction. It's as much the external stuff as the internal stuff that made it happen.

"We were on welfare and eating beans and rice, but we'd still joke, "We're gonna take over the world."Suroosh Alvi

Alvi: After the Supreme Court, Chet, what's next?

Kanojia: The question is, do we see the litigation all the way through? There's a lot of interest in our technology. Do we partner with somebody?

The broader theme is that people want different kinds of content. Different voices, sensibilities, and styles. My hope is that Aereo survives and participates in that, in some way. I can't watch cable TV news. It's infuriatingly dead to me. The same story, over and over again.

So Chet wants to start a cable news network...

Kanojia: [Laughs] No. But I desperately hope Suroosh does.

As Suroosh said, Eli, Upworthy launched with much early success. Still, what did you believe coming out of the gate that turned out to be completely wrong?

Pariser: We didn't want to do a normal media business model. We had this idea that, after you watch something, you would have a chance to actually do something about an issue. It was nice to have that connection--it just didn't work as a business model. But we realized that we were getting pretty good at drawing attention to a lot of social issues, and that we need to build a business model based on that. I will say, though, it's so hard to say, "Yup, we were totally wrong." It took some folks from the team saying "This just isn't working"--probably longer than I wish--until we all clued in.

Kanojia: I have never operated with a co-founder. How do you manage conflict?

Pariser: I started the company with Peter Koechley, who'd been managing editor of The Onion. We thought, Peter more oversees editorial, I more oversee business and the external piece. But we spent a lot of time commenting on each other's realms. An internal mantra--which we didn't create--is one of the big pieces of our culture: "Strong opinions, weakly held." Take a strong stand, have a point of view, and be convincible if someone has a better idea. If Peter and I were strong opinions, strongly held people, it would be a lot harder.

What would you tell the younger version of you?  

Kanojia: It's really tough to do something causing change in an established medium--a.k.a. Aereo. The stakes are so high that you don't have the time to gestate your product and vision. If you're passionate about something very small but purely futuristic, that has a better chance.

Alvi: Don't worry that you've never done it. Ignorance was a good thing, in our case. And, frankly, we were unemployable. We pretty much had to make this work.

From the October 2014 issue of Inc. magazine