2016-09-15



“My argument is, there’s another way to build a company. It doesn’t have to all be about the worship of bigness.”

On a recent episode of Recode Media with Peter Kafka, Skift CEO Rafat Ali explained how to start a media company without losing your soul.

You can read some of the highlights from his interview with Peter at that link, or listen to it in the audio player above. Below, we’ve posted a lightly edited complete transcript of their conversation.

If you like this, be sure to subscribe to Recode Media on iTunes, Google Play Music, TuneIn and Stitcher.

Transcript by Celia Fogel.

Peter Kafka: I’m here with my guest Rafat Ali, who is a two-time digital media entrepreneur. Welcome, Rafat.

Rafat Ali: Thank you, Peter.

Many of you know Rafat for paidcontent.org and your new company Skift. Am I pronouncing Skift correctly?

Correct, yes.

What does Skift mean?

It’s an old English word that means the first layer of snow of the ground. Nobody uses it anymore.

I thought it was a Finnish word or Norwegian word.

It’s also a Norwegian word for shift. So English and then Norwegian. So essentially for all intents and purposes, we own the word as it relates to travel.

You took a word that either isn’t a word or most people don’t know and you said, “This is going to be the name of my new travel site.”

Yeah. I bought the domain like five years before I started Skift.

So what is skift.com? What do I learn if I go to that site?

It’s the business of travel. So airlines, airports, hotels, destinations, online travel, cruises, between all these subsectors in the world’s largest industry by many accounts. Certainly the world’s largest employer of people. And there wasn’t one source when we started to understand the business of travel in a big-picture sense. There were obviously trades that have existed in various parts of travel, for decades, years, nothing that cut across all those sectors.

It’s a trade magazine, trade website, trade publication for people in the travel business. It’s not for business travelers, right? You’re not going to tell me how to upgrade my models.

No, we had plans for that initially. The idea was we create a B to B to C company, both sides, once we become experts. Once we become experts in the eye of the industry, then take that and translate it for the business travelers, certainly that was part of it. We just discarded it along the way as we realized what our focus is to be as we build a company.

Yeah, I wish you would give me some good business travel tips. Maybe you can give me some at the end.

You’ve emailed Jason questions and stuff.

Yeah! I know a guy that runs a travel site, I should ask. I want to know: LaGuardia or JFK?

Well I officially always have the line open so you can keep emailing me or Jason.

I went to Italy, I wanted help booking that. You’re really not helping me a lot, Rafat. [RA laughs] So I want to talk to you a bit about that site and why you created it. I want to talk to you about why you made PaidContent as well. I’ve known you a long time, I think you were doing PaidContent in what? 2005?

When did I start it? 2002. So Gawker and I started the same month. Coincidentally.

I happened to have interviewed Elizabeth Spiers here. It’s old home week at Recode Media.

So they took the model, the blog model, they took it in the consumer way, we took the industry news way.

So PaidContent, you can’t really find it now, right?

No, it’s dead and gone.

It got bought and sold.

I’m going to say it’s six or seven thousand stories I wrote over a 10-year period; except for archive.com, it doesn’t exist anywhere.

So there’s a percentage of people who are listening to this that would have seen this because they were in the media business for a while, if you didn’t get it in the Times, the Journal, you were getting it from PaidContent. You were an early prototype of a business blog, very influential. I want to talk about how you started that. But let’s go even further back. How did you launch that site? How did you get to the point where you wanted to launch a business site?

Well certainly I did not grow up thinking about going into business at all.

You group up where?

I grew up in India. I was born in U.K., grew up in Denver for the first six years and then we moved back to India and I grew up there from like 6 to 24.

You moved to the U.S. then?

And then from 24 I moved to the U.S. to do my master’s.

And the plan was what?

The plan after the master’s?

Yeah.

Was to come to New York and start covering the internet economy.

You got a master’s in journalism.

Journalism. From Indiana University Bloomington.

“I want to write about the internet in New York City.”

Yeah, so back when I was in India, in Delhi, I was working for the equivalent of an ad agent in India where I was covering internet advertising. Realized the action is in the U.S., how do I get to the U.S.? I say I’m gonna apply to journalism schools. I got through Indiana —

This is 1990 …

1999 is when I came here. So I was covering it in like the peak of ’97-’98. Obviously the peak days of the Web 1.0 boom. India was also starting that. And when I finished school from Indiana, I moved to New York, worked at a couple of dot-coms, for Silicon Alley Reporter, Jason Calacanis’s previous company or first company, I don’t remember.

He was probably selling something out of the back of a truck in Bay Ridge before that.

Something when he was doing with Sony. And then actually before that I was at Inside.com, the then-famous and now nobody remembers media site.

There was a period that anyone who was anybody either worked at Inside.com or aspired to work at Inside.com. All gone now.

All gone now. I mean, there were a lot of famous, well-accomplished people, so that was my two companies, two sites that I wrote for. Both of them closed down eventually.

So traditionally the route is, you get your journalism degree from Indiana and you go work for these sites, I’m assuming at the bottom of the masthead, and then you work your way up. Either those sites or you get to a bigger media company.

Yeah, I applied for all of them. I mean, the Wall Street Journal, Roger will tell you how many times I applied to the Wall Street Journal. Street.com back when it sort of was poeople knew it.

A place you wanted to go.

And then CNET. CNET was my dream job back then, it really was. Jim — who I still remember — used to break every freakin’ story about Yahoo. This was even probably before Kara was breaking stories about Yahoo. So I really wanted to go to CNET. And so I applied to all of these and did not get through.

Because?

I was not a citizen and then I later became a citizen so there were some visa issues that I sorted along the way. But I also came out at a bad time out of school. The Web 1.0 implosion had already happened. So nobody was hiring. So when everybody was running away from digital media slash internet because everybody said, “Look…” I don’t know if they exactly said it was a fad, but …

Right, because there was a period where everyone sort of said, “The internet? What’s that?” And everyone said, “Oh! The internet is great! Let’s hire everyone with a pulse, they’ll all come work at our internet site, they’ll all become internet millionaires.” And that went as you’d expect it.

Yeah, I was still in school then.

And you were in school so you missed out on that boom.

I missed all of that. Yeah, timing-wise I have some issues in life. And so when I came out it was that weird time between sort of first dot-com bubble had burst and September 11th hadn’t happened. So that weird one year in between where we felt like things were just getting a lot worse, it’s going to get a lot worse. So that’s when I came out and had issues in terms of applying to these companies, nobody was hiring, visa issues obviously were there. So I started a blog. I had been blogging for a while — as soon as I came to the U.S., I discovered blogs when I was at school. And starting personal blogging as like an Indian guy into America, my learnings of what I’m learning as an immigrant. And so then I started aggregating news — media news — as a way to show here’s what I can do as a journalist, please hire me.

Okay, so you were using it as sort of a work product.

As a resumé.

And you had a very specific style which was, “Hey, the New York Times wrote this, the Wall Street Journal wrote this, and I think that’s right or I think it’s wrong, or they’re really missing the real story,” and you would add little bits of commentary and then I think more and more reporting.

Yeah, it started initially because I was still employed full time at Silicon Alley Reporter. I was doing it on the side. And Jason to his credit never discouraged me not to do it even though, obviously, it was taking up my time. And initially I started carefully just commenting on what was happening just because I was reporting on the industry anyway. And then I started reporting on it when I lost my job. Then I just started reporting on the industry, essentially a phone and an internet connection was all I needed.

So you lost your job, and then did the light go off?

From New York I moved to London. London I was still looking for jobs for the first four or five months. I was a British citizen, born in the U.K., just never lived there. Nobody gave me a job again because the economy was pretty bad there as well. And so I almost got a job at Mining Magazine. I went through many copy editing tests, I’m so glad I’m not an expert at mining industry. And I just started the blog really while hunting a job — my distraction from hunting a job was to go in the internet cafe in East London and sit and blog.

Just type.

Yeah.

And when did you realize, “Oh, this is actually my job now”?

When somebody invited me to speak at a conference in Germany in this random small town outside Frankfurt. And they were giving 2.5 thousand euros which for them to me was like, “Shit I can move out of my aunt’s basement in London and actually get my own apartment.”

They read your stuff on — was it then PaidContent.org?

On PaidContent.org, yeah.

Worst name ever but this is a good lesson, right? You can start something with a terrible name and still succeed.

I know, seriously. Well, I mean I’ve changed. My new company has different lessons on that front. But yeah, it was not meant to be a company at all. It just ended up being one and once that came and then I started asking some industry friends of mine who were running software companies to “send me your banners. I’m going to put it on the site for free for like a month.” As soon as I put it on the site and the newsletter — and I had the foresight to understand the value of newsletter… I didn’t have foresight, I saw the value of newsletters at Silicon Alley Reporter. Daily, touchpoint to your reader, that Jason had done very well through his life early on. And so that’s what I started, a blog and a newsletter. People for a long time knew PaidContent as an email newsletter because I used to essentially take all the copy of every story, put it in a newsletter. And so that worked.

So over a couple of years, you turned this thing that wasn’t a job into a job. And then it’s —

Enough money so that I could live. I mean, I was young and single and living in a crappy room-share in East London. I could afford it.

And do you think you were good at what you did or did you think you were the only one doing it and by default you become the one that was the best at it, or both?

Both, I think. I mean, shit, what should I say about myself? Both in the sense that I guess I became… Now I’m reading some of the old stories and realized how naive or how over-confident I was about everything I thought I knew.

Well, it helps not to know anything, right?

Yeah. So I think that helped tons. Naive about calling names to people. Not calling names, but like being opinionated about companies, at 28, two years into your writing career, you shouldn’t be that opinionated. Turns out by being on the blog, with my own complete freedom, I was able to learn that.

Eventually you started building up a staff. And from the outside it seemed to me like you had figured out this thing — whether you intentionally did it or not — where you were writing for a relatively small community of people and you were the only one doing it so they all read you, they were giving you tips, you get this awesome feedback loop where you’d read Rafat, you’d send Rafat…

And the community was not online. The community was all offline. Email, phone and then eventually conferences as well. So when the world was talking about, “Oh, comments on blogs and trackbacks,” remember? I’m sure you remember. None of that was happening at PaidContent because it was an industry that did not have time to go into comments and discuss.

And again, because you’re writing about media, other high-profile media people are reading about you, talking about you. I remember going to an event where you had Arthur Sulzberger.

Yeah, that was the first New York event, New York Times’ David Carr wrote an article about it.

Yeah, and I think one of the benefits about being in that business is you get to sort of punch above your weight influence-wise, right?

Yeah. Media writing, media, you know this very well. [laughs]

Don’t tell people my secret, Rafat. And then at some point you take on some venture money as well?

Yeah, so Alan Patricof who had just exited his previous private equity firm, Apex Ventures, started a fund. And we were his first investment, second exit.

Were you looking for money?

No, I just literally used this story where I was in LA sitting at my desk writing, the phone rings and says, “I’m calling from Alan Patricof’s office.” I said, “Oh that. Silicon Alley 1.0 days, I remember Alan, sure I’m going to take the call.” And I talked to him and he said, “Are you coming to New York?” I said, “Well, I’m coming to speak at a conference next week, let’s meet.” And that’s how the investment happened. We raised a comically low half million series A, which you know, who does that in New York?

At the time it seemed like a lot of money. I remember reading about it.

Yeah, I don’t think we ever disclosed … it was like “less than a million,” people kept saying, “less than a million.” It was a half million. And it was delayed six months because I didn’t have any balance sheet or anything. My CFO who is my CFO at my company now, Michael Cunniff, he remembers, he tells this story to everyone, he came to my apartment in LA, he asked me where’s my stuff. I said, “Here, this is the shoe box, here take it.” And he literally had to create a balance sheet that then led to the investment. Because obviously they had to have all the stuff and taxes and everything.

So you raised money from Alan Patricof, you were right place right time, you’re working your ass off, and then the moral of the story is you make a gazillion dollars and live life happily.

Yeah, there are many lessons, but also did not sign an incentive-based exit, but that’s a whole different conversation we can have.

We should get to that conversation sometime. I try to get people to talk candidly about what happens when you sell your company.

What happens when you sell a company is a switch goes off. And I tell this to every entrepreneur who I met, there’s going to be a switch that’s going to go on in your head. You cannot control it. The only thing will happen is you don’t know when it’s going to happen. And when it’s going to happen, it’s over.

A switch that made you build that business. The engine that made you build that business will go off at some point.

Yeah, Henry Blodget, who’s tied up for ten years, at some point between zero year and ten year, the switch is going to go off and he’s going to leave. Turns out Arianna Huffington has not yet had that switch turn off. It just turns off. Or maybe it has.

We tried to work together years ago, or we talked about working together. So now here we are, selling socks.

I know, seriously. A lot of people I talk to along the way, I realize, oh wait, Nicholas Carlson, we did talk to him when he said, “I have an offer from Silicon Alley Insider.” I said, “If you’re going to play us on the offer, go work for Silicon Alley Insider,” and it was great for him!

It’s cool that we get to do this, because you were very influential for me. I was reading you when I was writing about media over at Forbes and again, you were really the only one doing it online. It was a big deal to me that you’d created your own business. That was pretty influential. And even when I went to go work with Henry Blodget, who we were just talking about, and Dan Frommer, and I think the original idea was to create a PaidContent-style blog.

Just not about media, and more geographic and stylewise it was very much like, “This is what was in the New York Times, this is what was in the Wall Street Journal, this story is wrong, also we have our own reporting.” But I was very influenced by what you had done, that style of commenting on what people had created. You get to take credit for generating a style of reporting and commentating.

I think bringing some human language into business reporting, bringing the fluency of blogs to business reporting, I think that’s probably the only thing I can claim to have brought to some extent.

Pretty cool, you built a thing, and you sold to the Guardian. I think that didn’t work out as well as either side wanted, which is a pretty common result.

Yeah, pretty common occurrence. Obviously I knew that because I was reporting on the industry, M&A was our bread and butter. I used to break tons of stories back in the day. We used to compete on a bunch of stuff too, but we thought we were going to be an exception.

If everyone knows that M&A generally doesn’t work, especially this kind of media M&A we’re talking about, why do people keep doing it?

The money’s great. Everybody makes money except for the buyer.

Why is the buyer doing it? The buyer is theoretically not a dumb person, not a dumb company, some of them are dumb, but many of them are accomplished, smart people. Why do they think the acquisition they’re going to make is going to work out?

So they’re hedging bets. I think smart, eminent people know that they have to… it’s not unlike VC. You buy a portfolio company, some work, some don’t. And so in media’s case, it’s obviously larger than just the corp dev person or the team, it comes hopefully from the top. And sometimes they’re buying innovations, sometimes they’re buying product. In media, it’s particularly difficult because media isn’t rocket science. Media is sensibility or brand or a lot more amorphous things that you’re buying. So in most cases cultures don’t work or we’re too small for it to work, which is the case with us. We were too small and we were too far.

When you were at PaidContent and got bought by the Guardian?

Yes. And Guardian was a giant company back then, even now it’s still very large, they had big plans in the U.S. This was like the third time trying to break into America. They failed the first two times, they failed with us as well. And to their credit, obviously they took the chance and did it. We were raising money at that point. Had we taken the venture funding, we would have been dead probably earlier than that just because the market was brutal. A meta media company in 2008/2009 had no business being in existence.

This is one of the problems of writing about media today: Is it as influential as it may be? Limited audience.

Yeah, nobody spends money. I mean, media businesses are hard, meta media businesses making money is terrible.

Shhhh. This is a meta media podcast!

So that’s what happened. They were laying off hundreds of people back home. We went from like 30 people to 11. We were cut to the bone. Editorial was still pretty strong but by that time your previous company had come in, was doing well, the previous incarnation of this company, AllThingsD, was doing well. So there’s a lot of competition and everybody was covering media. And New York Times and Wall Street Journal was very serious about covering the business and media. So it was very noisy. And I’m so glad not to be covering media today.

So you did a year, two years at the Guardian.

A two-year lock up. I was a year into it and the Guardian tried to sell us. Actually, my immediate bosses try to sell us but the CEO of the Guardian, who’s now the CEO of EasyJet, Carolyn McCall, she vetoed it. She said, “No, I read PaidContent every day, get value out of it, why haven’t you guys figured out what to do with it?” So they killed it. They killed the plan to sell. At that moment I knew nothing was going to happen. So I left like four months before my blog appeared. There was an earn-out involved that didn’t happen.

So you leave, and you think, “Alright, I’m done.” I remember talking to you about it, you said, “What I’m not going to do is create another B2B industry of vocation.”

I know. I was done with it.

And here we are, talking about your B2B …

Yeah, the lesson in life is don’t run away from what you know. But I had to take a journey to come back and learn: Don’t run away from what you know.

Just spell it out. Why didn’t you want to do the thing that you’d proven you were good at? Because from the outside it seemed like, oh you did the media, deal with something else.

Here’s why: There was a bit of a chip on my shoulder that people said, “Oh this was a fluke, prove yourself in a larger consumer thing.” And so I said, “Okay, that’s what I’m going to do.” And even to some extent with Skift, that was initially what I was trying to do.

To prove yourself.

To prove that I could do a larger consumer thing.

Right, so it’s not just enough to say, “That wasn’t a fluke, I’m going to do it again. It wasn’t a fluke, I’m going to do it better and bigger.”

And bigger. Certainly Skift is already bigger than PaidContent was in terms of revenue, in terms of audiences probably. But we are a business information company that talks about the business of travel in human language so people like you can understand, but I’m not trying to make money out of you.

So you go through a bunch of ideas and you end up at travel and you say …

Yeah, I almost went in sports, the business of sports. Because ESPN did not exist. And no, the business of sports. I thought Sports Business Daily, whatever it was called, was too old school. I could create something in the business of sports. I talked to Bankoff and he says —

Jim Bankoff, my boss.

Yeah. This was before.

My boss’s boss.

Yes. So he said, “It’s a great idea, let me introduce you to some people.” He introduced me to some people. Turns out I have no interest in sports. So that was an issue. [laughs] I do like Olympics but other than that I don’t know anything about American sports so that wouldn’t have helped. And I did go on the business of education, I looked at it quite seriously and realized education is local, this can be hard to do like a global play, whatever, international play. And so I did not do that. Also I did not have tons of interest in education, I didn’t have a kid yet. So travel is what I ended up with.

So you get to travel, you say, “I travel a lot, I have an affinity for that.”

I started learning about the business of travel by reading the trades.

And you say, “This is not just going to be a trade because we’re also going to have a consumer part of it and we’re going to have a data product and it’s going to be scaled up.”

Yeah, I said, “Politico has a consumer audience.”

So are these things that you wanted to do or are these things that you thought that VCs or other people wanted you to do?

Probably a mix of both. Now in hindsight, I was influenced by here’s how I can raise money for it. I’ve written about it, I’ve been pretty open about it, certainly the last year I’ve been open about it. VCs wanted to hear a lot of things. Data was one of them.

Because, again, if you say, “I’m going to create a B2B business publication,” they go, “That sounds good but that doesn’t scale.”

Yeah. I mean, it’s amazing. The VCs that said all kinds of sh— things to me …

You can swear.

… when they pestered me and are now saying the exact opposite things today while funding other media companies.

They’re flexible.

So it’s amazing. I also tweet about it quite a bit on and off.

Do they ask about the Tweeting?

[laughs] I’m certainly very vocal on Twitter.

I have to confess, I muted you.

That’s fine.

But I do wonder why you spend the time that you do on Twitter.

I know it’s an addiction.

Is it an addiction? Because it occurs to me the most obvious reason is this is a way for you to either psych yourself up or psych your team up, and you make public announcements and you kind of paint yourself in a corner and you have to fight your way out of the corner, and maybe that’s an intentional technique.

Yeah. Obviously all my team reads Skift, they’re going to listen to this podcast as well. So it’s a big part of the culture, I think the underdog fighting its way is part of it.

Yeah, a lot of your Tweets and your essays as well are about, “We’re a small company, we’re doing it differently, all of you big companies are wrong, you VCs are wrong, we’re going to show you that you’re wrong, doom is coming for you motherfuckers.” I don’t think you say motherfuckers.

No, I’ve never said that.

I get it. You can sort of clench up, right?

Yeah, I think these people do say, “Rafat, you’re a contrarian.” I don’t know what that means. I just know that the way I want to do things is different. My whole life has been about if people land in a place and drive to the right, I want to drive to the left. I don’t know why, but that’s just how I was built.

It’s worked out for you so far.

It’s worked out. And so it’s literally all my travels are people land in a city, they drive to the right, I take a car and drive to the left. That’s my life. And so it’s worked out. I do think that lots of follies of media in general are their own doing. That’s I think a common thread. And that too many incompetent people run tons of media companies in this world.

And now you can say that with authority because you’ve been through the doors and the grinders. You’re not a 28-year-old guy who doesn’t know anything.

No. And so I think what professional blogging gave me was a voice to write about the industry. What Twitter gave me, even though I was late compared to some of the early media people, was sort of finding a voice of my own, in the larger world, and my place in the world. And I bring that to the company, it’s an integral part of the company. If you were following my Twitter you would see that tons of it, like the amount of time I spend on creating the right culture for the company, is probably 60-70% of my time. It’s just an inordinate amount of time. And part of it is also is us against the machine to some extent.

Just the regretful Tweeting that many people do on Twitter. “Oh I shouldn’t type that.”

No, I mean in general not really. But I’ve certainly pissed off some of my investors in some of the tweeting I’ve done.

Because you’ve tweeted about them?

No, but in general about the venture world that I’ve talked about quite a bit.

And they come back to you and say, “Could you cool it?”

They have said, “Oh, I wish you could not say that.”

[laughs] And you said you wish you could do that too but you keep doing it, it’s an addiction.

In general, I would like to figure out a way to get rid of Twitter in my life, but it also is a big part of our success in the sense that the amplification that Twitter provides in the larger media space is unparalleled. We would not have been where we are today as a company, Skift’s — I hate this word but I’m going to say it — momentum, in general, that has translated into business for us, would not have happened had Twitter not existed.

Because what? It’s famously too small to be a real media business, so how are you using it to do your business?

Purely on an editorial basis, amplification. A lot of the times when our stories get picked up it’s not because media people are following Skift, it’s because they’re following me on Twitter. So bigger stories that we break that then translate into larger stories from different organizations and stuff. So our amplification beyond the industry — which it has to a large extent — is only possible, not because of Facebook or Snapchat or Instagram that everyone else worries about.

That’s not your audience.

It’s not our audience. LinkedIn, not even that. Doesn’t have in-built amplification build in that Twitter’s has. So I think that’s why I love and hate it, because hate it because it just takes so much of my time. I also have a kid now in the last year and a half, so he actually does not like when I hold up the phone. So I’ve learned to not have it in front of him.

So Twitter didn’t exist when you built your first business. We talked about how you sort of initially wanted to build something that wasn’t like your first business and then you have. What lessons did you bring from PaidContent that are working for you at Skift?

I think the tone and voice in terms of having an opinion about what you’re writing about. And an opinion based in actual reporting. Not like some of the other unnamed media reporters that happens tons without actual reporting. But us having confidence in our voice because we report on the industry so extensively. I think that was a thing that we brought with PaidContent.

So we know about this topic, we don’t have a neutral view on it, we’re going to express that view, we’ll tell you why we think that.

Our view of travel and the world is a very progressive view of the world. Like progressive in the real sense of progressive. Eclectic, diverse, intermingled, globalization, we’re all for it. It’s part of our DNA.

Something that should be good for you is the fact that AIrbnb is a giant company. Didn’t really exist when you were starting this thing up, or maybe it just sort of started.

It had started but it was not turning out.

But enormous effects and you can be the dominant chronicler of that.

Of Airbnb and what it begets in the larger sense.

Right. And what it does to the hotel industry, what it does to travel.

Tons of it. And so when people talk about us, and I wince when people say that, people in the travel industry, they say, “You are a disrupter.” Which I just wince at because one, it’s just so laden with so much meaning, but they’re saying it because we are chronicling the changes that are happening. Both in terms of traveler behavior as well as the companies that are disrupting.

Since there really aren’t a lot of dedicated Airbnb reporters, you guys qualify as the one. What’s your relationship like with that company?

Very complicated. Brian Chesky for a long time thought that we were out to get him.

That’s the CEO of Airbnb.

Yeah. It took a while for us to build that relationship back editorially. And then our business side, which is, I’m not involved with editorial, that’s run by my co-founder Jason Clampett who is the head of content and also the editor in chief, so we have talked business with Airbnb, nothing has happened yet. But it’s a complicated relationship because of our history with Airbnb. Silicon Valley companies in general, you know this very well, have a very thin skin about anybody asking them the hard questions. This is a playbook that you and I have seen with every hot internet company for the last fifteen years. It’s a playbook that’s playing out with Airbnb, probably with Snapchat, I don’t cover, but you guys can tell. So I think it’s a complicated relationship. They understand our place in the industry, we define the battle of Airbnb versus cities by looking at New York City, the famous story that we did that put us on the map.

Which was?

Which was New York City as a mirror to the larger issues with Airbnb. And we did a very deep dive, we did a data dive of New York City listings. We were the ones that put up that 75 percent of their listings are illegal.

This is the whole push and pull about what AIrbnb does to the real estate world, to the hotel world.

To the neighborhoods, to regulation, etc., etc. New York State tried to subpoena to get our data and we said, “We’re a neutral party, we’re not going to get involved.” They subpoenaed somebody else. And so yeah, that’s why it’s a complicated relationship.

How do you grow this business? It is an industry trade. At some point do you say, “Alright, we’ve nailed travel and now we’re going to do the standard thing which is create other verticals”?

When I was talking to VCs, the plan was to take the Skift model in ten different verticals. We’re not going to do that. What we’re going to do is what’s the next adjacent vertical to travel? It’s food and beverage. So F&B. So we are, I haven’t really hidden it, but we are going to launch something in the food and beverage world. So essentially the restaurant and eating out world. Which is always, as you can imagine, very intertwined with travel. So that’s our next step. It’s going to launch October/November time frame. It’s going to be part of Skift.

Okay. But if I want to learn about …

Restaurant tech. Not food tech, which is a larger world, but innovations in restaurants, technology, guest experience, all the stuff that we in a parallel way cover in travel, we’re going to cover in F&B.

Vox Media, where I work, Jim Bankoff has worked with you, one of the verticals is Eater, and they used to be a trade, right? It talked about what was opening and closing and what chef was doing what, and over time they’ve sort of moved away from that and become much broder and bigger intentionally. When you see someone doing that and you’re about to go and create a digital trade for the food and restaurant business, do you go, “Oh, maybe there’s a lesson I could learn from that.” Or do you go, “Oh, they’ve left an opportunity for me.”

You’re giving me too much credit, I haven’t thought it through. No. We have seen this, I have liked this sector for a long time. I think the sensibility of Eater and Vox and others, the larger sensibility, design, how they talk to sort of a crossover audience for a long time in a lot of their sites, I think that’s kind of what we learned. That’s one thing I learned from Vox very well and the gadget blog before that. But no.

So small is good for you. And I do want to go back to the big versus small because this is sort of one of your rants.

It is one of my favorite things to talk about.

Your argument, if I’m summing it up correctly, is you shouldn’t take money just to take money and you shouldn’t grow just to grow. And when it comes to media businesses you shouldn’t make big media properties. Am I fairly summing it up?

Yes. My argument is there’s another way to build a company and it doesn’t all have to be about the worship of bigness. I think that’s it.

Small is beautiful.

Small is beautiful. Small business is great, we are proud to be called a petite media company. We embrace it. But it’s not like two years ago I was there. I’m there now. And so it took me a while to come up to this place where small is great, we don’t need to raise more money, we’re unlikely to raise more money. We may at some point in the growth equity phase at some point. I just think that all the larger troubles that media is in today is chasing the next best thing and you and I wrote about this tons of times in the past.

You’re four years into it?

Four years, we just celebrated our anniversary. We were in Cuba for our retreat.

How many employees?

29. And four open positions. So at 33 we’ll be soon.

You have 29 employees, you’re making enough money to take them to Cuba, are you profitable?

Yes, we’re profitable. We’re profitable this year.

You have a profitable self-funding media business. Good job.

Yeah. We have the most amount of cash we’ve ever had in our bank account as of this month.

And now you’re going to spend it all on expanding your next vertical.

[laughs] No. But look, I don’t understand tons of finance. The only thing I understand is cash flow. And turns out most of the old-school business people you talk to will tell you the same thing. And so if I’m old school in that, that’s great.

It’s cool to be at this age where you can be a sage. You’re offering sage advice, right?

I don’t know anything about anything. I just pretend.

That’s where you started as a 28-year-old, not knowing anything. And now you’re a fortysomething?

42, yeah.

What I really wanted Rafat to do for me for years is provide awesome travel tips because he knows the industry back and forth. Like I’ve thought for years that if you’re going to book a trip for business, you book in the morning because that way you don’t get flight delays. Is that correct?

This is what my editorial tells me, because I’m not the actual person writing it, but there’s no way to game the system. You’re up against a giant machine that changes their ticket prices in milliseconds.

Your travel tip is there are no travel tips?

Hacking is not worth the time it takes. This is certainly true for leisure travelers. Like you and I going on a family trip. There’s no way to game the system. It’s just not worth it. If it costs you another $50 extra to buy a room or a flight, do it, it will save you three hours of saving $50. So trying to hack the system is a loser’s game.

Nooo, our audience lives to hack the system. They’re hacking their bodies, they’re trying to figure out growth hacking, there’s gotta be ways to hack travel.

And also, you know, loyalty is pretty much a scam for much of the brands.

Don’t get the credit cards.

Credit cards is the only way at this point. But like actual company loyalty, like airline loyalty, hotel loyalty at this point is pretty much moot. Unless you are a very very high-mileage traveler. At which at this point, unless you’re not, none of it will make any sense.

Carry on or don’t carry on? Pack a bag or check a bag?

So I’m of the school — this is me personally — I always check in.

You like hanging out at the luggage carousel.

I don’t like the feeling of being rushed. Sure, I have to pay for it, but might as well. And just get it off my mind so I can be more free while traveling, especially at the airports and stuff.

So Rafat’s travel tips after four years of experience are don’t game the system and check a bag.

Yeah, I told you I’m always “people go right, I always go left.” So that was my tip.

Rafat, thanks for coming.

Thank you.

I’ve been looking forward to this for a while, I’m glad we got to do it.

Alright, thank you.

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