It's Personal Stories, A Hospitality Podcast

Rafat Ali_ CEO_Founder_ Skift_ interviewed by David Kong (1)

• David Kong

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Rafat Ali shares his journey from engineer-turned-journalist to serial media entrepreneur, reflecting on the choices, setbacks, and grit behind building Skift. We explore the most admired leadership qualities, founder-led passion, and customer empathy. Don’t miss his parting advice on career compounding, travel, embracing contrarian views, and the power of “ask and you shall receive.”

David Kong:

Greetings. I'm David Kong, the founder and principal of Its Personal Stories. We are the only podcast focused on hospitality leaders telling their personal stories. Today, I'm delighted to welcome Raha Ali. He's a person that actually needs no introduction because most of us know him. He is the founder and CEO of skit. Skit is the go-to. Business intelligence platform for the industry. Many of us use it. I, in my previous have, used Skift for research and the latest news. So it's really an honor to have you Raffa,

Rafat Ali:

of course. Thank you, David. And I know our team has. Spoken to you when you were running Best Western. I've been following your podcast since right when you launched, and it's great to be on it.

David Kong:

It's great to have you. Now, Raffa, you have a very interesting career journey. You started as a journalist, you founded paid content, and then 13 years ago, you founded Skift. I was wondering if you'd be kind enough to share the choices and risks that shaped your path.

Rafat Ali:

Yeah, I was born in uk, but grew up in India. My father was a professor. In those days, and this is true even now for Indian families, parents want their kids to be doctors, engineers, and lawyers. My elder sister became a doctor and I was the second in line, and so I had to become an engineer, even if I didn't want to. My parents pushed me into it. I don't mean it in a negative way. That was the last time they pushed me. And for all the choices that I made since, they were hugely supportive of it, which I'm hugely thankful for'cause it was a big risk for me. I went to school for, actually became a computer engineer. Engineering degree that I did was in computers. It was early days. 1992 is when I started the course. The four year B Tech and came out in 96. And so back in those days, the coders of the developers weren't the rock stars that there are today. And back in India in those days, you, we would basically be working at an outsourcing firm, coding, which didn't sound very glamorous to me, didn't sound very fulfilling to me. And so the choice that I made then was that I wanted to go into creative field, and so I came across some advertising copywriter that came from Delhi to this town where I grew up and sounded very glamorous to me. Advertising copywriting. This sounds very cool. And so I read up all the books on advertising in the university library, all the classics of gilian advertising, bunch of others and moved to Delhi and tried to get a job. Nobody took me seriously because I was a computer engineer. So what are you doing in advertising copywriting? Why do you wanna earn one 10th the salary that you would get as a computer engineer? And I went into PR at some PR agency as a junior person. My job was to deliver print press releases to media offices back in Delhi and I got exposed to the journalist on the other end and I said, oh, that's what I wanna do. I want to be a journalist. Forget advertising copywriting. So I applied. I was one of the few journalists that really wanted to be in B2B journalism,'cause young journalists or people who are gonna school want the glamor of the big magazines. Obviously things have changed now, but I was the one that wanted to go deep into a sector and focus on just being hopefully being the most influential force in the sector that I choose. And for me it's the one, one of the choices I guess I've learned over the years is like, going deeper is better than going wide. You read as wide and you absorb as wide as you can'cause how else will you then know the world? And then connect the dots deep into the sector in travel. And it reflects, I'm sure you've seen it reflects in how we look at the world of travel through skit, which is everything affects travel. Travel affects everything, and we have to look at it from a wide angle lens and then go deep. And so I think I learned that over a period of time in my career. So I went into this trade magazine in India. Web 1.0 was happening all over here in Silicon Valley and U.S. And I started writing internet stories about the internet scene in India. Early days realized the action was in us. I applied for further studies in US Masters and I got into Indiana University, which is where I went for my master's, Bloomington, Indiana. There was a new media fellowship they had. So I got a full ride, which I'm hugely thankful for. My parents couldn't afford sending me to US. That was the only way I could. And that really set my career and I stayed here, worked at a couple of dot coms. As a writer, like news media companies and then started my blog Paid content, which you referenced that turned into a media company. So paid content was probably the earliest blog that turned professional, as in bloggers in pajamas creating media companies. Wired did a story on me back in 2003. I think blogging for Bucks was the headline. I didn't expect to become an entrepreneur, just had our family, had no history of it with academic family. So I learned everything on the job and lo behold, what is it now? 2025. So 25 years later, into entrepreneurial media slash information businesses that have created.

David Kong:

Wow, what a story.

Rafat Ali:

Yeah. My story in a small way is only possible- for all the problems that there is in America, is only possible in America. I still believe it.

David Kong:

Amen to that. The world has changed a lot in the last 13 years since you founded skit, what was your original vision for Skift and how has that evolved over time?

Rafat Ali:

One of the earliest pitch decks that I wrote was we want to create the Bloomberg of travel. So news, research, conferences, and cutting across different sectors. So as you very well know, since you've spent your life in this industry lots of hotel trades, a lot of airline trades, et cetera, et cetera, but nobody was connecting the dots across all these sectors. Certainly nobody was looking at consumer behavior and how that was changing in an age of digital and mobile, and now obviously ai, et cetera. So my contention was there needs to be a Bloomberg of travel for this age. And so that original vision has definitely played out. Meaning we wanted to raise the metabolism of coverage in the industry for being as big and as influential as it is. You very well know this. From a policy perspective on geo particular perspective, it punches below its weight in all possible ways on a global scale, on a national scale, on a regional level, et cetera. In fact the lack of travel as in closing borders and visas is what everybody leads with, as these days, unfortunately. So part of the mission was honestly, because I came as an outsider was this naive vision of we gotta raise the metabolism, the industry and put to its rightful place in the world by the virtue of covering it, instead of a forward digital, forward, less jargon, more designed forward, more experience, forward coverage of the industry. If I can humbly say so. I think we've done our part in it. I think it's still a lot to go from a policy and global influence of travel industry perspective. But we certainly, that's a underlying mission, even if it's not a direct part of what I talk of what we talk about elevate the industry. Additionally, we wanted to also go into the cons, let's first try B2B media news coverage of the industry, and then we will create a consumer site that is aimed at prosumer travelers, business travelers, people who are expert travelers. That part didn't happen. We just got too busy with the, with just creating the industry information thing. But how we write in a less jargon, more forward looking way. We do have readers who are not from the industry, but it's not a business for us. We don't get any money from them. We don't aspire to get any money from them. So that part got put by the wayside. We tried initially to create some data services. We didn't know what we were doing and this was early days of social media, and so we had some index of which brands were best as social media and then the social media companies clammed down on free access to their APIs and all this other stuff happened. So we failed at that. We moved into the business of restaurants, Skift Table. We acquired this small restaurant tech newsletter with an idea that, what we've done in travel, we'll do in the f and b world. Lots of connections, at least on paper between f and b and hospitality particularly didn't succeed. We did for about a year and a half, and I shut it down in summer of 2019. We also moved a little bit into business of wellness. We started a newsletter with an idea that travel, restaurants and wellness is the business of leisure where disposable income is spent on paper's. Not like great idea. It's just that there's so much to do in travel that in hindsight, that was the right decision. For us to just go deeper and deeper. So it's changed. We've done things that work, things that didn't work. And as any company does.

David Kong:

That's great. You try new things that didn't work, you move on and you learn from it. I always believe that our hardships and setbacks are actually great learning opportunities. So in that vein, would you mind to share some of the toughest challenges that you have faced in building Skift and the lessons that taught you about resilience and leadership?

Rafat Ali:

Yeah. Oh man. Oh my goodness. as you already know, our lessons are as much travel industry lessons as it is skiff lessons.'cause obviously we are a hundred percent focused on the industry, but early on we raised some venture funding. So we raised about$3 million a seed when we started the company, Jason, who's my co-founder, and I launched it back in 2012. And so we raised some seed funding with an idea that will create news and this consumer thing that I just mentioned and these data services, and we'll raise more money to do more and scale quickly like any venture backed startup. We failed at raising the next round series A. I was out on the road 2013 or 2014, pitched, I don't know, 50, 70, 80 investors. None of the investors believed in our vision. There are investors willing to invest. We just couldn't get a lead. As it is in all startups. You find a lead and then others will follow. Didn't happen. At some point in 2014, we just decided to bootstrap from there. And so I call Skift, The Bootstrap plus company as we did raise a little bit of money, but it's been 13 years in and we do have investors, but again, these are small amounts and investors beyond a certain point. I don't have a board that had a huge effect in how we build a company, which is you have to essentially, eat what you kill. This is a Zuckerberg phase.'cause apparently Zuckerberg only eats animals that he kills himself. And I forget the whole context of it. The creativity that comes with not having tons of resources, in my opinion, outweighs anything that with tons of money you can do. And so that's always been our philosophy. Like one step at a time, two steps at a time. We take risks. And the ability to take risks is lower in the sense that we just don't have that much cash. But then you become creative and they risk in different ways. So certainly that was a huge part. And since then I've become a big advocate of not raising too much money for startups in general that don't need to, particularly media information companies. Creative type startups'cause they may not be venture backed businesses to begin with, right? They may not have the venture returns that venture capitalists are looking for. So certainly that was a big one. COVID was another one, obviously for all lessons that you learned during COVID, we learned during COVID as well. I had to lay off one third of the staff. That was tough. We were 60 people down from 40. These 20 people, 21, 22 people that we laid off were laid off for no fault of theirs. We had to survive. We had a very senior HR consultant that was working with us to help us set up HR more formally after many early years. she was the former HR head of New York Times. So a lot of the experience. So as we're trying to figure out how to come up with the list. We cut the office, we cut the software, we cut everything we could cut before we came to our team. And she had this idea let's include the people as in ask the team for voluntary furloughs. I've heard this in many larger companies, but as a small company, it was very meaningful because a bunch of people raised their hands. I'll go one, I'll go three days a week. I'll go four days a week et cetera, et cetera. So that was really we still didn't save us enough. We still had to lay off a bunch of folks, but initially the furlough and then we had to let them go. But including people in your decisions was really a big part of how I learned it from like instead of top down, including people even in the hard decisions. It was one of the biggest lessons I learned from that bunch of other crisis is we, Silicon Valley Bank, if you remember happened Oh, yeah. Two years ago.

David Kong:

Yeah. We

Rafat Ali:

had every cent of our money in Silicon Valley Bank.

David Kong:

Oh no.

Rafat Ali:

And so when the collapse happened, I think it's two years now. Those three days were the worst. COVID was bad. But it was still slower compared to Silicon Valley Bank. Every cent of your money disappearing. We had$7 million in the bank account and it went to zero. We tried to get our money out and we were too slow. Then money came back'cause President Biden, whatever said, you have to rescue these companies and the bank, et cetera. We didn't know. And the lesson I learned, and I wrote about it too was that you have to take emotions out in such a short time if you make these big decisions. There was a grief period, like there was one time where I called my president. Called her and I just broke down. I cried. I said, we're done 11 years of work, it's over. And I did not know about bank rescues, et cetera. Didn't have the history of understanding that it was gonna be okay.'cause at some point the government generally steps in. I didn't have that concept. What I wrote is if there is grief for a period of time, shut down your emotional brain and then shift to your execution brain. We created a virtual war room as in a zoom group of the five, six people in the company. We figured out how to do the payroll. The next payroll. And then by the time we had to figure that out, it was all happening on a weekend. Nobody else in the team, in the company of like at that point must have been 70 people or something, had any idea. They were reading the news. Our team didn't understand or didn't know we had a bank account in Silicon Valley Bank. Some of the salespeople knew, et cetera, et cetera. But not everybody knows, like why would editors know that we have a bank account in Silicon Valley Bank? So at some point, you have to insulate people in your company. You have to shield them from creating panic. Those are some of the things that I learned over the years.

David Kong:

Thank you so much for sharing those challenges and the very valuable lessons that you learned from them. Wonderful lessons! Now let's switch gears. You have interviewed many very respected and accomplished leaders, and you've also interacted with many others. What are some of the qualities that set apart the truly exceptional leaders?

Rafat Ali:

I have a bias for founder led companies. Founder led companies have a different level of passion and intensity. A lot of us are intense people. You meet Brian Chesky you are overwhelmed in half an hour talking to him because he's created something iconic out of nothing. so I have a affinity to founder led businesses. He came out with the founder mode philosophy last year that became viral of like as big as the company is, the founders have to be hands on and how can they not be chief product officers of their companies? He didn't mean literally, but it metaphorically meant that you have to be hands-on with the product. I have an affinity for hotelier CEOs. People that rose through the ranks and many of them, as you very well know, have risen through the ranks. And hotelier CEOs, particularly those on the sort of luxury end of the world, just have a different feeling of how they run their companies.'cause they've learned the customer first ethos through their careers that then they bring to their leadership as well. And the companies run by it. If you're in the luxury world where it's very high touch, it lends itself to it. I've seen a lot of the CEOs in travel very much in touch with the frontline workers. Travel has a lot of frontline workers, hotels, airlines, all types of businesses, have a lot of frontline workers. You have to be out there, experiencing what the frontline people are experiencing for you to come back and then be able to do it. This is not directly in travel, but definitely related to travel. Dara Khosrowshahi who was the CEO of Expedia went to become the CEO of Uber. He's done interviews with us and also to other media on how when he started driving himself as an Uber driver, did he really connect the problems, the drivers and the issues that drivers have with Uber. And was at least from a product level and was able to then come back and say. Guess what? This problem has been there for years. Why didn't we solve it? So I feel that understanding only happens when you are the front lines yourself. How can you not be the chief customer service officer in many ways? And so I embodied that philosophy myself, but I've also seen that in a lot of people, accessibility matters, particularly in this day and age. I've talked about this before as well. Like you can't sit on an ivory tower and not be on, for instance, social media, et cetera. I do respect people who have zero social media just because it's such a cancer in general. If you're running a consumer company, people see it through very quickly, and so you have to be communicating, I think those who communicate in their own language. I won't give an example of what happened at the Global Forum, like there was a bunch of CEOs and I interviewed many CEOs last month at our goal forum. I won't mention the one CEO, who didn't come across well because this person was very scripted, versus the CEOs who talk, in a non-scripted way, and their PR people are scrambling by the way, to pick up all the pieces. I think you have a better respect for people who speak their mind than people who and I understand public companies have responsibilities and you have to obviously, stay within certain boundaries. All the stuff I totally understand. But CEOs and leaders are as much storytellers as they are, business leaders, decision makers, et cetera. Last thing I'll say, the speed of decision making does matter. In a day, you're making million small decisions and I've always said action over intent. Always. Always, and this is true for our company, for my philosophy, but it's also true for a lot of other, general in any business action or intent. And businesses that I've seen do well have, embodied that in many ways.

David Kong:

Thank you for sharing all those very important qualities that you want to possess as an exceptional leader. I totally agree with you on everything that you said, especially being genuine and accessible and making decisions expediently and being grounded. Those are just wonderful qualities. Thank you for sharing all that. Talking about exceptional leader, you've always been respected in the industry as a forward thinking, progressive leader. And I was wondering if you can share some of the habits and practices that help you stay grounded, creative, and empowered.

Rafat Ali:

Yeah. we're in the travel industry. Travel is amongst the most progressive expressions of human curiosity, like what is around the corner? Isn't that the most elemental of human instincts? I'm sure this was same for you when you were running Best Western even now. The most energized I am about Skift is when I'm out meeting people, and bring back tons of ideas. My team knows Rafat is on the road. He's gonna come back with 10 ideas and our life is about to get harder. And also, one of the things I've learned quite a bit every time when I'm some distance away from, even though we don't have a physical office post COVID, we're a fully virtual company. If I'm and I live here in New York if I'm traveling, I still feel like I'm away from work. Even though, we're all virtual. So I can work from anywhere. When I'm away from, even if I'm working there, I'm away from work. So if I'm in Rome, which I was last week for four or five days, I have a renewed appreciation of the work that our team does'cause I'm less hands on for those four or five days. And when I'm just reading stories from the outside or the research from the outside, I say, wow, this is really good work our team does. So I have a better appreciation of that. The act or travel makes you creative. And grounded in the, in oh, we have achieved something. I have three young kids who are sitting downstairs quietly only because they've been, they're on tv. I have a 10-year-old and a 6-year-old and a 5-year-old. And I'm coming back from the Global Forum after all the biggest CEOs I gathered bone tired and like I come home and the three kids. Jump on me and do not care a bit about what has your dad done for the last three days and you get grounded because this is the reality, as in I gotta make them dinner or, or, focus on them, et cetera. So certainly that keeps me grounded. The other thing I'm very in touch with my heritage as an Indian, origin person who wasn't born there, but my family's there. And and also I'm a practicing Muslim, so I think those two personal parts of my existence, not that I keep them front and center in my work, like explicitly, but it's a huge part of my existence. I think the immigrant mentality that I'm sure you will identify with as well in this case in Indian immigrant certainly keeps me grounded and I go back to India, so I just realize yes, we have mobile phones there, we probably have more mobile phones and more cars there than US these days, but we're still taking bucket showers. And the electricity still goes out. Like the power still goes out for an hour, two hours there. And like the hawkers that used to be there, selling vegetables are still there. And so it's incredible. Like it's a whole different existence. I fly 14 hours and I'm in a whole different world. And so that keeps you grounded. And it's just the joy of travel as we talked about, but also just the incredible diversity of the world keeps you grounded.

David Kong:

You are absolutely right. Thank you for sharing that too. I don't want to keep you away from the children for too long'cause I know they haven't seen you for a while and they're gonna lose patience very soon.

Rafat Ali:

No. So I'm gonna ask you

David Kong:

one last question. Our show is about self empowerment.

Rafat Ali:

Yeah.

David Kong:

What is the final advice that you can share with our.

Rafat Ali:

Something I didn't do as much when I was younger, primarily because I couldn't afford it, which was travel early, travel often. If you can, and particularly, outside of the Western bubble that we exist in, right? Be open to. And this is certainly not political, but listening to contrarian ideas that you don't agree with is an art developed over a period of time. You and I as young we're oh we are right. Nobody, everybody else is wrong, but just listening to contrarian ideas. Or things that you don't agree with or people that you don't agree with. Our country is a prime example of not listening to the other person. It does open up your mind. One of the other things I learned about America when I first came is ask and you shall get, if you don't ask, you won't get it. Which is a very interesting concept coming from a Indian culture where you have deference for authority. Generally, you don't ask outta respect. But early on you gotta ask for things. Asking is a proxy to initiative. And in our company, people who have shown that they can paint outside the lines, if you will, and raise their hands to do things even though they may not be part of their job description, are the people who have risen through the ranks and, the last thing I'll say, and this is not an original advice, but again, I'll go back to Dara. Dara, the CEO of Uber did an interview with LinkedIn, some video thing that he did a few years ago. And he had this concept of career compounding, which is a concept he borrowed from the financial compounding as in you save money over a period of time and then with interest and stuff, it becomes, it's one of the most powerful concepts as in finance and his concept of career compounding is that what young people do is they're jumping from jobs to jobs to get raises, et cetera. His is that stair while in a company, if you like it, and the and learn the craft and. Staying early in your career, staying at a company long enough and early in your career will then have exponential benefits. We have examples in our company where Anne, who's my chief of staff and also SVP of Growth is a live example. She was at some other company for a year and a half before she joined us, 23 years old back then and has been with us for eight years and has risen through the ranks, did sales, et cetera, et cetera, and showed initiative. She is now one step away from C-Suite at Skift or anywhere else she wants to go if she decides to. It's only eight years of a life in a long life yet to come and she's 30 ish or whatever, and already at the cusp of C-suite in our company it's a great example of, in a small company, if you like your job and if you put roots in and learn different things over a period of time, you can then use that as a catalyst for so many things. So I was very taken when Dara said this,'cause unconsciously I was trying to do this with our team and then he put a name to it, which was just great.

David Kong:

I absolutely love it! Love that career compounding.

Rafat Ali:

It's such a great it's such a great advice and it's contrarian and as like these days everybody wants to jump fast.

David Kong:

Yeah, it's worked for me. Certainly if you look back at my career that is, and hospitality, and

Rafat Ali:

by the way, I'm very impressed by, in general and hospitality people have long careers. Many of the CEOs have been at these companies for decades.

David Kong:

Yeah, that is true. Your four pieces of parting advice is so unusual. I have not heard any one of them mentioned in my previous interviews, but all four are so valuable. I like the career compounding. I like ask and you shall receive because as immigrants we are taught to just work hard and things will take care of itself. Yeah. But it never does. Have to be proactive and I like that. Travel broadens your horizon. It is so true. Everything that you said as your final advice, it's just fabulous. Thank you. Regrettably, we're coming to the end of our show, Rafat, thank you. I am most grateful that you've taken the time to be with us today.

Rafat Ali:

Alright, thank you David.

David Kong:

Thank you. And to our audience, if you enjoy this show, we hope you'll join us on our website. It's personal stories.com. You'll find many other interviews on this website. Thank you again for joining us.