Neil Vogel, the CEO of About.com. Courtesy of Neil Vogel

Update: About.com announced on Tuesday, May 2 that it'd be changing its name to "dotdash' after 18 years operating under another name. In our April podcast with CEO Neil Vogel, he explained how he arrived at that rebranding decision after two years of observing media trends and making the wrong choices.

Here's the interview, which was first published in late April, below.

About.com launched in 1997. It used to be one of the world's most visited websites.

Today, internet entrepreneur and investor Neil Vogel has been tasked with saving the IAC-owned dot-com brand from extinction.

"I got a phone call from Joey Levin, who is the CEO of IAC. He asked, 'What do you think of About.com?'" Vogel said during a recent interview with Business Insider. "My answer — in perfect arrogance — was 'I don't.' Who thinks of About.com? Nobody."

Levin persuaded him to come in for a job interview anyway, and Vogel walked out convinced he could help turn the company around. Now he is CEO of About.com, and to save it he's trying something that sounds crazy.

He’s shutting down the entire website in early May. In its place, he's launching a half-dozen new sites.

"This is either going to work and be a great success or we're going to crash the plane as we're flying it and this is going to be a horrible failure," Vogel says he told IAC.

So far, the radical plan seems to be working. We spoke with Vogel about the turnaround, and, before that, how he founded the Webby Awards, which have been dubbed "the Oscars of the internet."

On an episode of "Success! How I Did It," a Business Insider podcast about the careers of accomplished and inspiring people, Vogel also explained how a cross-country road trip in a Ford Bronco changed his life.

Listen to the full episode here, or listen later with the buttons below:

Subscribe to "Success! How I Did It" on Art19 or iTunes. Check out previous episodes with:

Following is a transcript of the conversation, edited for clarity and length.

Alyson Shontell: About.com is a 250-person media company that you've revived. It was a dot-com baby, founded in 1996.

Neil Vogel: Nineteen ninety-six. We're 20 years old. We're not a baby — we're not even adolescent. We're like a full-fledged millennial.

Shontell: You've been a venture partner at Firstmark Capital. You've created a company that made awesome events like Internet Week and the Webby Awards, which have been called "the Oscars of the internet."

Vogel: I've done a lot of things. I'm old, man — I'm old.

Shontell: Let's go back to when you were young and hungry. How did you start this career? Investment banking, right?

Vogel: I listened to your podcast with [Bustle and Bleacher Report founder] Bryan Goldberg and he talked about this, but when I got out of college, which was in 1992 — I went to Penn — the only things seemingly you could do were become an investment banker, a consultant, or a brand manager somewhere. And I didn't do any of those things.

For a year I took an internship at IMG, the big sports agency, which I was terrible at, and I hated it. After seven months, I went back to my roots and was an investment banker. I was a banker for five or six years. I very quickly learned that I admired and respected my clients a lot more than my bosses. I did not want to be some dude eating Chinese food in the office on Sunday night at 7:30 making a model for someone else's business. That, to me, seemed stupid. It seemed to me like I wanted to be the guy the model's being made for, which makes some sense.

I ended up leaving and going to work with a couple of guys who started a company called Alloy — or Alloy Media Marketing, for you internet 1.0 people. I was the sixth person there. We ended up growing to be a $300 million-revenue business — very profitable. It went public and had a really good run.

Shontell: What was it like back in the dot-com days for people who might be too young to remember?

Vogel: It's hard to describe. We were kids. We were 27, 28, 29 when Alloy went public. We were just playing business with other people's money. And it felt irresponsible, but we tried really hard. We worked incredibly hard.

The founder of the company, Matt Diamond, was incredibly smart. He was always very focused on building a business that made money. We always made money so we didn't have the outcome of a lot of 1.0 guys. We ended up being pretty successful. But it just was crazy. Everything was at hyper speed. Nobody knew anything. We were the first at everything we did. It was really fun.

Ultimately, I wanted to run my own thing. I left, took a year off, and, with a partner, started a business called Recognition Media. We ended up owning and producing nine or 10 different award shows and events, including the Webby Awards, and we started Internet Week, which we subsequently sold.

A life-changing, yearlong road trip in a Ford Bronco

Shontell: Before we get into that, I want to discuss the time you spent in between jobs. You did a cool soul-searching experiment in which you bought a truck and you drove across the country.

Vogel: I did. I took, like, almost a year off.

Shontell: Tell me about this crazy road trip that changed your life.

Vogel: I don't know — I was 32, single, and we just had this reasonably good outcome. I had no responsibilities and no expenses. I had a dumb rental apartment. So I bought an old Ford Bronco, took the roof off and drove around for a summer.

My father gave me great advice. He said, "Look, you're in a position where you don't have kids, you don't have anything. Go get yourself bored and figure out what you want to do."

For a couple of months I was trying really hard to think about it and figure it out. Then I decided to not think about anything. Believe me, I know it's an incredible luxury to be able to do that.

I didn't think about anything, and then everything became clear. It's an amazing feeling to have no responsibilities. Just "What am I going to do? Oh, I'm going to drive here and visit my friend." Or "I'm going to get on a plane, go to Europe, and hang out." It was amazing.

I was at the beach with some friends before Labor Day weekend in 2004. I hadn't done anything for the whole summer. I wasn't even checking email. I panicked because I had hit maximum boredom. I got in this truck and I drove back to Manhattan on the Thursday before Labor Day weekend. When everybody was going out to go the beach and have fun, I got on a plane, flew to LA to where my business partner was, and we wrote a business plan, and that became the business that was the Webby Awards and Recognition Media.

I tell people it was the best thing I've ever done in my whole life.

Shontell: You're on the beach, you realize "Oh my gosh, I actually miss work. I want to do more. I want to do something." You have this idea. Had you done anything with events before?

Vogel: No, nothing. Zero things.

Shontell: You just thought it would be a fun thing to start.

Vogel: We actually started the company by buying a very small business. Before I dropped off the face of the earth, I talked to a lot of smart media people I knew. And a guy called us with an opportunity. He said, "You can buy this thing called the Telly Awards," which was a little award show based in Ashland, Kentucky.

He found this business in an ad in the back of The Wall Street Journal. He read it, then he clipped it and faxed it to me. I took a look and said, "Wait a minute. This is a database of creative professionals who are all doing internet things and need recognition for their work." If you make TV commercials, who says whether you are doing a good job or not? You need third-party validation.

We did some research, found out there were a million of these little awards around. If we bought this first one and figured it out, we could probably do a bunch more and make this work. That's what we did. I flew to LA to do the work on this Telly Awards thing that we then raised a little bit of money and bought a few months later.

Building the Oscars of the internet, the Webby Awards

Foursquare cofounder Dennis Crowley at the 2011 Webby Awards. Flickr/Eddie Codel

Shontell: What exactly are the Webby Awards, and how did they become this glamorous thing?

Vogel: We bought the Telly Awards and we'd had some success with it. Then, we found out the Webby Awards were owned by IDG, the big media company. They started this award show in the '90s in San Francisco that got some traction. But it kind of went out of business. For two years they didn't have the show. But they had the brand. We approached them and said, "Guys, we want to buy this from you."

The business model is, people pay to enter, and we get lots of corporate sponsors and have a show. The first year we had 800 entries, mainly all from the United States. By the time we were done with it [seven years later] it was about 14,000 entries from 60 countries. It's the award, the Cannes Lions, or the Oscars for people who do internet stuff.

We built a brand really, really stealthily. We did it by just making sure the brand was impeccable, that the most important, most influential people liked it. And we did it all online at a time when that felt really weird to people.

Shontell: So it's a once-a-year event. How much money can you make from an event like that?

Vogel: I can't really tell you exactly how much. You can figure out the math. The more people who enter, the better off this thing is. Then you're connecting really big corporate sponsors with very tight, very engaged audiences that are super valuable. We can put you in front of 2,000 people who make the best stuff in the world every year. That's a really valuable thing.

Shontell: Was it ever hard?

Vogel: Everything is hard. It's impossible. It tells as a super-elegant story. No, but this is impossible. Everything was a disaster. We had eight offices. We couldn't get anything right. We made so many mistakes. The nature of the internet is it's very forgiving. You can't really make that big a mistake.

The interesting thing about a business that is an award show is it's once a year. Now, at About.com, we can make changes that are instant tomorrow. At the Webby Awards, you make a change, it takes a year to see if that worked. You learn how to manage businesses differently because you have a full-year cycle, which is often very annoying. We made every mistake a startup can make.

Shontell: Despite that, someone did come in and buy a big chunk of it.

Vogel: Yeah, we were happy. I'm still on the board. Then I transitioned to Firstmark Capital, where I have a bunch of friends who are investors.

Shontell: They've got early-stage investments and things like Pinterest, Airbnb, and Draft Kings.

Vogel: I spent probably a year hanging out with those guys, and I learned so much in that year from just sitting and listening to their process. The first thing I learned is I'm a terrible investor. I like the quick wits of running businesses. But the long lead time and thoughtfulness required to have a thesis and invest against it and follow up is just not my jam.

A radical plan to save About.com — shut down the URL and start from scratch

Neil Vogel is an internet entrepreneur and the CEO of About.com About.com

Shontell: So you started to get bored and then IAC called you. IAC owns About.com.

Vogel: Yes. So About.com was owned by The New York Times. They owned it for five or six years. IAC — Barry Diller and crew — bought it for about $300 million at the end of 2012.

Shontell: Significantly less than The Times paid for About.com.

Vogel: It is less than The Times paid, which is less than Prime Media paid before them. I think it's widely known, but About was a mess at that point. It was still one of the 20 biggest sites on the internet, but there had been a lot of neglect.

IAC, who's very opportunistic in buying things, said, "OK, this still does a lot of revenue. It has 100 million users a month. We're pretty sure we can do something cool with it." So they bought it.

Shontell: There was a bidding war for it too. Answers.com wanted it.

Vogel: There was a very quick bidding war that they won. I think the entire cycle was seven days, which is crazy when you think about how that works. Probably five or six months after they owned it. I wasn't there, so I can't say this definitively, but I can guess. I think it was a bit of a bigger mess than they thought.

I got a phone call from Joey Levin, who is now the CEO of IAC. He might deny it went this way, but it very much went this way. He calls me — Joey's a very direct character — and he says, "What do you think of about.com?"

My answer — in perfect arrogance was — "I don't. Who thinks of about.com? Nobody. It's a thing with these blue links on it. I don't think about About.com."

He says, "Come in and talk to me about it." I go in and talk to him about it. I thought he wanted me to help him find someone to run it. I went into his office, and the next thing I know, I'm going home with a stack of information.

I'm thinking, "Ugh, I'll look through it, I guess."

By the time I got through it, I had a full mental turnaround on what this thing could be. I was definitely like the 25th person they talked to.

Shontell: It was founded in the search era, right? There was no social or Facebook driving a ton of traffic. It was all the good old days of Google search traffic.

Vogel: It's all Google search. The model was — this is important to note because it took us a bit to figure out — the model was the same thing as AOL, or the same thing as MSN, or the same thing as Yahoo. It was a big general information site. In our case, we made the content ourselves with experts. They made content different ways. But it was a big general information site. I decided I would ... I'm like, "OK, you know what? I'm going to do this." I went and I signed up to do it, and a little bit of the reason was the "you can't fall off the floor" reason. I'm not going to be the guy who ruined About.com. It's already ruined, so this is all upside here.

What Marissa Mayer and Yahoo did wrong

Shontell: What do you think of Marissa and Yahoo?

Vogel: We can actually talk about that. We have point of view on that, which is part of how we decided to do what we did. We actually have a strong point of view on that. I'll make this story a little shorter here.

I joined, and within a year we took the employees from 150 to 250. Every person, with the exception of one or two above senior director was new. We have 250 people now, and there are probably 10 who were there before we got there. When I got there, I couldn't tell you how many ads we served the day before. I couldn't tell you how many visits we. It was just a mess.

We got there and spent the first year building a data-science team so we can understand what was going on. Building a sophisticated programmatic ad stack because our site kind of looks like crap. It's very hard for us to sell premium stuff. So we're going to start selling programmatic things like moving away from some other monetization things. We used a lot of Google ads and we have to not do that. Users don't really like that at scale. Hired a bunch of smart people. I basically went and drove the "A-Team" van around New York and was like, "I know you, you're great. We've worked together. Come join us!" I think people got excited about the chance to fix an iconic internet.

A year and a half into it, we launch a brand-new site and rewrote every line of code. We had code from the '90s in there. We put forth the new About.com and everyone was excited. We stopped the decline. We started to make more money, traffic stopped going down. We could go to a cocktail party with a straight face and say, "Look at this things." We had some pride in what we were doing and it was making some sense. We felt good, and then six months later we're still in the exact same spot and we're like, "Ugh, why is this not growing?" Again, at this time, everyone's really happy with us. IAC is happy with us.

Probably a year after we launched, we went back to IAC, and this was the scary moment, this was like the big move, and said, "Guys, everything we did was wrong. We're doing it wrong."

Shontell: How did you come to that? It just stalled?

Vogel: It goes back to your Marissa question. We realized that our fundamental model of what we were doing was wrong. Our value is we have this great content that advertisers will like and consumers like, but nobody cares about a general-information site anymore. You have three constituencies when you're a publisher: advertisers, consumers, and people who send you traffic (basically algorithms). And it turns out that if you play tennis this weekend and hurt your knee, you don't want your "why my knee hurts" advice from About Health. You want it from WebMD or Everyday Health. We're like, "Oh, point." If your router breaks at home, you don't want that from About Tech; you want that from EnGadget or The Verge or someone how to fix it.

Advertisers? We heard this constantly: "Your data is great, your scale is great, we like your content, but you're not endemic, so we're not working with you." They want head-of-household moms, and they make computers, but they would not give us any money. And then the other problem was algorithms. Google and Facebook and those guys no longer knew what to make of us. You can't have, "Symptoms of Colitis" content on the same domain that you have "How to Unclog My Drain." On the same domain you have, like, "How to Cook Beer-Battered Chicken" and "How to Fix My Tendinitis."

Shontell: It kind of works for Wikipedia, though.

Vogel: We'll talk about that in a second. It's a little bit different. For a site like us ... Wikipedia's traffic is going down, by the way, from search, because they're not specific. If you have colitis, you'd rather go to a colitis-specialty place than Wikipedia. They're losing also.

We came to the realization that we needed to do something. We went back to IAC and to that meeting and said, "Here's what we're going to do: We're going to turn this place from AOL or Yahoo or MSN, and I'm going to turn this into Condé Nast or Vox. And that's what we're going to do. This is either going to work and be a great success or we're going to crash the plane as we're flying it and this is going to be a horrible failure. But we're betting, because our content is good, because we still have search traffic, because we know how to play social, that we're betting that we can do this."

And IAC — because they're not a media company, they're an internet company; it's a huge difference that I've learned — they basically said "Do it. Do it. Go ahead, take the chance. Roll the dice and do it. We'd rather have the outcome that you are the next Condé Nast than have the outcome that is now, which is we're going sideways."

'We could have literally gone to zero"

Barry Diller, head of IAC, knows how to take risks. Michael Seto/Business Insider

Shontell: That sounds like it makes a lot of sense. But there is huge risk involved with a move like that.

Vogel: Existential risk. We could have literally gone to zero.

Shontell: Yes, because you have, what, over 100 million people visiting About.com?

Vogel: Yeah, about that.

Shontell: And you're talking about all these new properties that have to start from scratch, right? Then what's left for About.com?

Vogel: What we said was, we're going to take pieces of About.com, we're going to break them off and make these new brands, and then when we're done, About.com is going to go away. As of May 2, we're announcing a new brand name for all of overarching brand for our brands, and About.com is going away.

Shontell: This site that had 100 million-plus readers, you just canned.

Vogel: We didn't can it yet, but we're canning it in six weeks. Again, because we've now made five different, sites that if you add them up have more users than About.com had. That was the trick.

Shontell: How long did that take?

Vogel: We've done it over the last 12 months. The story of the first one is an easy one to tell.

Shontell: Within a year you've built four new brands that now are bigger than About.com ever was.

Vogel: In aggregate, when you add up all the things, not ever was, because that was humongous, but we are — our traffic now, we have more traffic now with four of our five brands launched. So four brands in the market, one brand still under the About.com name. We have more traffic now than we had a year ago, two years ago, when we were just About.com.

Here's what we did: The first thing we wanted to launch is we wanted to launch ... We launched a health brand called Very Well. We dove right into the pool. Health is our most valuable, most-trafficked, biggest vertical, so we came up with an idea. Our content is very much in the style of like WebMD or Everyday Health. But we thought those sites, we just didn't think they have served a market need. We thought that we could make a beautiful, kinder, gentler health site. You go to these some of other sites with a headache, you think you have a brain tumor. You come to us with a headache, we're going to make your headache feel better and explain why you had a headache and make it better. That was the thesis.

So we took our 100,000 pieces of health content of About.com, threw 50,000 in the garbage because they were old. We didn't like them. The other 50 [thousand] were read by our writers. If it was medical information; it was read by a doctor. We had 30,000 pieces of content read by physicians, edited, cleaned up. Built a brand-new site from scratch, a new taxonomy for our content, put it on the site.

We did that. We built this beautiful new site from scratch, everything from scratch. Took design, product, content, tech, everyone, walled them off. You now work for Very Well; you don't work for About anymore. You work for Very Well.

Shontell: The About people who remained were no longer able to write about beauty and health or about —

Vogel: Yeah, we moved the health stuff all to Very Well. Health is now gone from About.com, and we launched it in April.

Shontell: You see, instantly, a ton of traffic to About.com, I'm sure, go away.

Vogel: Terrifying. Really, you have to compare all of About.com to now About.com, plus Very Well, right? So here's what happens, a lot of, more, probably at the time, 70% of our traffic was from search. Three weeks after we did this —

Shontell: No search traffic, I'm sure.

Vogel: No, what you can do ... the trick is making the search traffic move to your new place. We built a new site with a new taxonomy so every URL over here gets redirected to one over here.

A month after we launched this thing, our health traffic, which is our most valuable traffic, was down. Traffic was in like 45% or 50%. But we're like, "OK, we're just going to hold on and we're already halfway done doing our next vertical." All of a sudden, Facebook, Google, all the domains figure it out. As of now, today, I think our health brand has — I'm going to get this slightly wrong because I always get numbers slightly wrong — I think we had 8 million uniques when we started a month, I think we have 17 million uniques now to Very Well. So we've pretty much doubled in size in 12 months. We're by far the fastest-growing thing in the health space. I think we're No. 4 or 5 on comScore on health because our bet was right ...

We knew that this would work. Then we launched something in the summer. Ran a very similar playbook on our personal-finance content called The Balance, which has pretty much doubled in traffic since we launched it this summer. We launched something called Life Wire in November, which is our evergreen-content tech site — how to fix my router, how to unbrick my iPhone. We launched three weeks ago, about a month ago something called The Spruce, which is the third-biggest home site on the internet, only behind HGTV and the Hearst Brands. We had such scale on About, that we're launching these new brands into the world that are new to the space with no legacy issues, look like start ups, but all of a sudden, like we're top 10 in comScore because we're coming with such scale. The market's like, "What? Where do you guys come from?"

And we have one more site to launch, called Trip Savvy, which we're launching right after we change our name. We're now going to change the name of the company May 2.

Shontell: So as a collection of sites, how much traffic do you guys have?

Vogel: More than we started. I think — I don't know — last month ... internally, I think comSquare was like 60 million last month or something. So we got a lot of scale. We're around the same size as you guys. I think internally we're like 100 million.

The future of media isn't about scale; it's about finding a niche

VeryWell is one of the new websites Neil Vogel has launched at About.com. Very Well

Shontell: So, for a while it was great to be a site that was all-encompassing, had all this scale, you know, the Yahoos, MSNs, and you. Are you're saying that that's no longer the case and that the future is to go niche?

Vogel: It doesn't work. Yeah, it doesn't. I just think everybody wants expert —

Shontell: The scale days are over?

Vogel: You see it in the mall, right? There's no place for a department store. People don't want that anymore. People want things that are specialty. I think the other people in our position —

Shontell: Except for Amazon.

Vogel: Except for Amazon. But there's always a place for that. There's a place for Amazon and Target and Wal-Mart, cause they're competing on price, or service, or something. Not on expertise. And that's more of like a retail thing. But in content, you generally want content from someone you believe is an expert in that. That trends toward being an expert in like, a domain of content, which trends toward being vertical. And I think different people have made really interesting decisions about this.

I think AOL has made a brilliant decision. We looked at our content and said, "All right, we make really premium content in these very premium areas." AOL looked at their type of content and said, "You know what, this is content that is probably going to be best served by programmatic ad selling." Cause of the type of content it was, not that it's good or bad, it just is. They built an unbelievable ad stack, they assembled properties that work like this. And it totally worked, and they crushed it. And now they're like Target. Like it totally works for them, and now that's why Yahoo makes sense. I think MSN didn't want to deal. And Yahoo made a different decision.

Like we looked at what we were doing and said, "We make money one way. We sell ads against content. And we're doing it wrong, but that's the fundamental model that works for us." Yahoo wanted to become something completely different, that I don't think anyone totally understands exactly what the thesis was. And I think that's why it didn't work. I think the AOL-Yahoo combo is gonna be great. It's gonna be great for advertisers. If it works it's gonna be like a legitimate third option to the big two. And I think they took the right approach to content.

Shontell: The big two being Facebook and Google. The Duopoly.

Vogel: The Duopoly. No media buyer in the world wants there to be only two places to buy stuff from. Look, it's really dangerous and they're growing like crazy but ... If you make valuable content, and you give people a really great experience, there is a place for you in the world. When you're general, like when you're the old About.com, there might not have been a place for us in that world. Because it just doesn't work. But when you're Very Well or The Balance, and when you're like a mutual-fund company that needs to advertise against people who are specifically looking for mutual fund information, we're an unbelievable resource for them. That's better than like guessing someone wants mutual funds on Facebook.

Shontell: So one thing you mentioned is that with AOL and Yahoo merging under Verizon, you think it'll be great. And could maybe challenge these guys. And that's a mega-merger.

Vogel: That's a big one.

Shontell: You know, all these huge companies coming together under Verizon. Do you think that's going to keep happening, and is that is your goal with About, to build it up to a point where you could join and be a power player in a big mega-merger like this?

Vogel: I don't know. I think if you look at the history of IAC they, you know, the market we have is $5 billion or $6 billion, but the value of the companies that have come out of IAC are, what, like $50 billion or $60 billion. So there is a history at IAC of being the builder, not the buildee. And if we do this right, we have a really interesting opportunity to build something great.

Shontell: So one kind of different question for you, what's Barry Diller like?

Vogel: First of all, he's great. He does not suffer fools. There's something incredible frustrating that happens when you deal with him in that you'll be in a meeting with him, or you'll get some feedback from him via email, or secondhand, or you'll talk to him directly. And he will say something to you that, at the time, you will be like, "I don't what?" Because you're like an arrogant CEO and you're like, "I ... I ... I know better about my business than he does. What's he talking about?" And then a day later, you're like in the shower, and you realize, like, "Ugh, he was totally right. He was a thousand percent right."

There's nothing he hasn't seen or been through, and he has this really unique way, which I think you do, when you sit in his perspective, of just looking at our problems or issues and just ignoring the nonsense, and like, bam. Like right to it. And sometimes by getting right to it you don't understand that right away, because you're too in the weeds, or you're busy running the business. But he just like, nails it. And he's great to work for. He does not suffer fools, there's not a lot of, like, nonsense. But it's awesome to work for someone that, and this doesn't happen a lot.

Shontell: Very true. So to wrap this all up, if you had to say the one thing you've had a lot of different lives in your careers. In all of them you've found success. So what do you think is the one common thread that has made you successful in all of these different areas and, ultimately, in your career?

Vogel: I'm annoyingly relentless when I believe in something. When I was a banker, I figured out that you'll be much better at doing something if you're passionate about it. And it's not saying like, "My great passion in life is to build publishing companies," or "My great passion in life is to build award shows." But if you believe in what you're doing and you can get excited about it, you're gonna be a thousand times better. And I'm really direct and I'm really honest with people, which doesn't always work that well. But if people always know where they stand with you, you will always know where you stand with them. And I think that's really valuable.