October 12, 2025 • 29 mins
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.”
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David Kong (00:01):
Greetings.
I'm David Kong, the founder andprincipal of Its Personal
Stories.
We are the only podcast focusedon hospitality leaders telling
their personal stories.
Today, I'm delighted to welcomeRaha Ali.
He's a person that actuallyneeds no introduction because
most of us know him.
He is the founder and CEO ofskit.
(00:23):
Skit is the go-to.
Business intelligence platformfor the industry.
Many of us use it.
I, in my previous have, usedSkift for research and the
latest news.
So it's really an honor to haveyou Raffa,
Rafat Ali (00:37):
of course.
Thank you, David.
And I know our team has.
Spoken to you when you wererunning Best Western.
I've been following your podcastsince right when you launched,
and it's great to be on it.
David Kong (00:48):
It's great to have you.
Now, Raffa, you have a veryinteresting career journey.
You started as a journalist, youfounded paid content, and then
13 years ago, you founded Skift.
I was wondering if you'd be kindenough to share the choices and
risks that shaped your path.
Rafat Ali (01:08):
Yeah, I was born in uk, but grew up in India.
My father was a professor.
In those days, and this is trueeven now for Indian families,
parents want their kids to bedoctors, engineers, and lawyers.
My elder sister became a doctorand I was the second in line,
and so I had to become anengineer, even if I didn't want
to.
My parents pushed me into it.
(01:29):
I don't mean it in a negativeway.
That was the last time theypushed me.
And for all the choices that Imade since, they were hugely
supportive of it, which I'mhugely thankful for'cause it was
a big risk for me.
I went to school for, actuallybecame a computer engineer.
Engineering degree that I didwas in computers.
It was early days.
1992 is when I started thecourse.
(01:52):
The four year B Tech and cameout in 96.
And so back in those days, thecoders of the developers weren't
the rock stars that there aretoday.
And back in India in those days,you, we would basically be
working at an outsourcing firm,coding, which didn't sound very
(02:12):
glamorous to me, didn't soundvery fulfilling to me.
And so the choice that I madethen was that I wanted to go
into creative field, and so Icame across some advertising
copywriter that came from Delhito 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 bookson advertising in the university
(02:36):
library, all the classics ofgilian advertising, bunch of
others and moved to Delhi andtried to get a job.
Nobody took me seriously becauseI was a computer engineer.
So what are you doing inadvertising copywriting?
Why do you wanna earn one 10ththe salary that you would get as
a computer engineer?
And I went into PR at some PRagency as a junior person.
(02:57):
My job was to deliver printpress releases to media offices
back in Delhi and I got exposedto the journalist on the other
end and I said, oh, that's whatI wanna do.
I want to be a journalist.
Forget advertising copywriting.
So I applied.
I was one of the few journaliststhat really wanted to be in B2B
journalism,'cause youngjournalists or people who are
(03:18):
gonna school want the glamor ofthe big magazines.
Obviously things have changednow, but I was the one that
wanted to go deep into a sectorand focus on just being
hopefully being the mostinfluential force in the sector
that I choose.
And for me it's the one, one ofthe choices I guess I've learned
over the years is like, goingdeeper is better than going
(03:39):
wide.
You read as wide and you absorbas wide as you can'cause how
else will you then know theworld?
And then connect the dots deepinto the sector in travel.
And it reflects, I'm sure you'veseen it reflects in how we look
at the world of travel throughskit, which is everything
affects travel.
Travel affects everything, andwe have to look at it from a
(03:59):
wide angle lens and then godeep.
And so I think I learned thatover a period of time in my
career.
So I went into this trademagazine in India.
Web 1.0 was happening all overhere in Silicon Valley and U.S.
And I started writing internetstories about the internet scene
in India.
Early days realized the actionwas in us.
(04:22):
I applied for further studies inUS Masters and I got into
Indiana University, which iswhere I went for my master's,
Bloomington, Indiana.
There was a new media fellowshipthey had.
So I got a full ride, which I'mhugely thankful for.
My parents couldn't affordsending me to US.
That was the only way I could.
And that really set my careerand I stayed here, worked at a
(04:45):
couple of dot coms.
As a writer, like news mediacompanies and then started my
blog Paid content, which youreferenced that turned into a
media company.
So paid content was probably theearliest blog that turned
professional, as in bloggers inpajamas creating media
companies.
Wired did a story on me back in2003.
(05:07):
I think blogging for Bucks wasthe headline.
I didn't expect to become anentrepreneur, just had our
family, had no history of itwith academic family.
So I learned everything on thejob and lo behold, what is it
now?
2025.
So 25 years later, intoentrepreneurial media slash
(05:28):
information businesses that havecreated.
David Kong (05:32):
Wow, what a story.
Rafat Ali (05:33):
Yeah.
My story in a small way is onlypossible- for all the problems
that there is in America, isonly possible in America.
I still believe it.
David Kong (05:42):
Amen to that.
The world has changed a lot inthe last 13 years since you
founded skit, what was youroriginal vision for Skift and
how has that evolved over time?
Rafat Ali (05:54):
One of the earliest pitch decks that I wrote was we
want to create the Bloomberg oftravel.
So news, research, conferences,and cutting across different
sectors.
So as you very well know, sinceyou've spent your life in this
industry lots of hotel trades, alot of airline trades, et
cetera, et cetera, but nobodywas connecting the dots across
all these sectors.
Certainly nobody was looking atconsumer behavior and how that
(06:16):
was changing in an age ofdigital and mobile, and now
obviously ai, et cetera.
So my contention was there needsto be a Bloomberg of travel for
this age.
And so that original vision hasdefinitely played out.
Meaning we wanted to raise themetabolism of coverage in the
industry for being as big and asinfluential as it is.
(06:38):
You very well know this.
From a policy perspective on geoparticular perspective, it
punches below its weight in allpossible ways on a global scale,
on a national scale, on aregional level, et cetera.
In fact the lack of travel as inclosing borders and visas is
what everybody leads with, asthese days, unfortunately.
So part of the mission washonestly, because I came as an
(07:02):
outsider was this naive visionof we gotta raise the
metabolism, the industry and putto its rightful place in the
world by the virtue of coveringit, instead of a forward
digital, forward, less jargon,more designed forward, more
experience, forward coverage ofthe industry.
(07:23):
If I can humbly say so.
I think we've done our part init.
I think it's still a lot to gofrom a policy and global
influence of travel industryperspective.
But we certainly, that's aunderlying mission, even if it's
not a direct part of what I talkof what we talk about elevate
the industry.
Additionally, we wanted to alsogo into the cons, let's first
(07:45):
try B2B media news coverage ofthe industry, and then we will
create a consumer site that isaimed at prosumer travelers,
business travelers, people whoare expert travelers.
That part didn't happen.
We just got too busy with the,with just creating the industry
(08:06):
information thing.
But how we write in a lessjargon, more forward looking
way.
We do have readers who are notfrom the industry, but it's not
a business for us.
We don't get any money fromthem.
We don't aspire to get any moneyfrom them.
So that part got put by thewayside.
We tried initially to createsome data services.
We didn't know what we weredoing and this was early days of
(08:29):
social media, and so we had someindex of which brands were best
as social media and then thesocial media companies clammed
down on free access to theirAPIs and all this other stuff
happened.
So we failed at that.
We moved into the business ofrestaurants, Skift Table.
We acquired this smallrestaurant tech newsletter with
(08:49):
an idea that, what we've done intravel, we'll do in the f and b
world.
Lots of connections, at least onpaper between f and b and
hospitality particularly didn'tsucceed.
We did for about a year and ahalf, and I shut it down in
summer of 2019.
We also moved a little bit intobusiness of wellness.
We started a newsletter with anidea that travel, restaurants
(09:12):
and wellness is the business ofleisure where disposable income
is spent on paper's.
Not like great idea.
It's just that there's so muchto do in travel that in
hindsight, that was the rightdecision.
For us to just go deeper anddeeper.
So it's changed.
We've done things that work,things that didn't work.
And as any company does.
David Kong (09:33):
That's great.
You try new things that didn'twork, you move on and you learn
from it.
I always believe that ourhardships and setbacks are
actually great learningopportunities.
So in that vein, would you mindto share some of the toughest
challenges that you have facedin building Skift and the
lessons that taught you aboutresilience and leadership?
Rafat Ali (09:54):
Yeah.
Oh man.
Oh my goodness.
as you already know, our lessonsare as much travel industry
lessons as it is skiff lessons.
'cause obviously we are ahundred percent focused on the
industry, but early on we raisedsome venture funding.
So we raised about$3 million aseed when we started the
company, Jason, who's myco-founder, and I launched it
(10:15):
back in 2012.
And so we raised some seedfunding with an idea that will
create news and this consumerthing that I just mentioned and
these data services, and we'llraise more money to do more and
scale quickly like any venturebacked startup.
We failed at raising the nextround series A.
I was out on the road 2013 or2014, pitched, I don't know, 50,
(10:39):
70, 80 investors.
None of the investors believedin our vision.
There are investors willing toinvest.
We just couldn't get a lead.
As it is in all startups.
You find a lead and then otherswill follow.
Didn't happen.
At some point in 2014, we justdecided to bootstrap from there.
And so I call Skift, TheBootstrap plus company as we did
(10:59):
raise a little bit of money, butit's been 13 years in and we do
have investors, but again, theseare small amounts and investors
beyond a certain point.
I don't have a board that had ahuge effect in how we build a
company, which is you have toessentially, eat what you kill.
This is a Zuckerberg phase.
'cause apparently Zuckerbergonly eats animals that he kills
(11:20):
himself.
And I forget the whole contextof it.
The creativity that comes withnot having tons of resources, in
my opinion, outweighs anythingthat with tons of money you can
do.
And so that's always been ourphilosophy.
Like one step at a time, twosteps at a time.
We take risks.
And the ability to take risks islower in the sense that we just
(11:43):
don't have that much cash.
But then you become creative andthey risk in different ways.
So certainly that was a hugepart.
And since then I've become a bigadvocate of not raising too much
money for startups in generalthat don't need to, particularly
media information companies.
Creative type startups'causethey may not be venture backed
(12:04):
businesses to begin with, right?
They may not have the venturereturns that venture capitalists
are looking for.
So certainly that was a big one.
COVID was another one, obviouslyfor all lessons that you learned
during COVID, we learned duringCOVID as well.
I had to lay off one third ofthe staff.
That was tough.
We were 60 people down from 40.
These 20 people, 21, 22 peoplethat we laid off were laid off
(12:27):
for no fault of theirs.
We had to survive.
We had a very senior HRconsultant that was working with
us to help us set up HR moreformally after many early years.
she was the former HR head ofNew York Times.
So a lot of the experience.
So as we're trying to figure outhow to come up with the list.
We cut the office, we cut thesoftware, we cut everything we
could cut before we came to ourteam.
(12:50):
And she had this idea let'sinclude the people as in ask the
team for voluntary furloughs.
I've heard this in many largercompanies, but as a small
company, it was very meaningfulbecause a bunch of people raised
their hands.
I'll go one, I'll go three daysa week.
I'll go four days a week etcetera, et cetera.
(13:11):
So that was really we stilldidn't save us enough.
We still had to lay off a bunchof folks, but initially the
furlough and then we had to letthem go.
But including people in yourdecisions was really a big part
of how I learned it from likeinstead of top down, including
people even in the harddecisions.
It was one of the biggestlessons I learned from that
(13:32):
bunch of other crisis is we,Silicon Valley Bank, if you
remember happened Oh, yeah.
Two years ago.
David Kong (13:37):
Yeah.
We
Rafat Ali (13:37):
had every cent of our money in Silicon Valley Bank.
David Kong (13:41):
Oh no.
Rafat Ali (13:43):
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 comparedto Silicon Valley Bank.
Every cent of your moneydisappearing.
We had$7 million in the bankaccount and it went to zero.
We tried to get our money outand we were too slow.
(14:03):
Then money came back'causePresident Biden, whatever said,
you have to rescue thesecompanies and the bank, et
cetera.
We didn't know.
And the lesson I learned, and Iwrote about it too was that you
have to take emotions out insuch a short time if you make
these big decisions.
There was a grief period, likethere was one time where I
(14:24):
called my president.
Called her and I just brokedown.
I cried.
I said, we're done 11 years ofwork, it's over.
And I did not know about bankrescues, et cetera.
Didn't have the history ofunderstanding that it was gonna
be okay.
'cause at some point thegovernment generally steps in.
I didn't have that concept.
(14:44):
What I wrote is if there isgrief for a period of time, shut
down your emotional brain andthen shift to your execution
brain.
We created a virtual war room asin a zoom group of the five, six
people in the company.
We figured out how to do thepayroll.
The next payroll.
And then by the time we had tofigure that out, it was all
(15:06):
happening on a weekend.
Nobody else in the team, in thecompany of like at that point
must have been 70 people orsomething, had any idea.
They were reading the news.
Our team didn't understand ordidn't know we had a bank
account in Silicon Valley Bank.
Some of the salespeople knew, etcetera, et cetera.
But not everybody knows, likewhy would editors know that we
have a bank account in SiliconValley Bank?
(15:28):
So at some point, you have toinsulate people in your company.
You have to shield them fromcreating panic.
Those are some of the thingsthat I learned over the years.
David Kong (15:40):
Thank you so much for sharing those challenges and
the very valuable lessons thatyou learned from them.
Wonderful lessons! Now let'sswitch gears.
You have interviewed many veryrespected and accomplished
leaders, and you've alsointeracted with many others.
What are some of the qualitiesthat set apart the truly
(16:02):
exceptional leaders?
Rafat Ali (16:04):
I have a bias for founder led companies.
Founder led companies have adifferent level of passion and
intensity.
A lot of us are intense people.
You meet Brian Chesky you areoverwhelmed in half an hour
talking to him because he'screated something iconic out of
nothing.
so I have a affinity to founderled businesses.
(16:26):
He came out with the foundermode philosophy last year that
became viral of like as big asthe company is, the founders
have to be hands on and how canthey not be chief product
officers of their companies?
He didn't mean literally, but itmetaphorically meant that you
have to be hands-on with theproduct.
I have an affinity for hotelierCEOs.
(16:49):
People that rose through theranks and many of them, as you
very well know, have risenthrough the ranks.
And hotelier CEOs, particularlythose on the sort of luxury end
of the world, just have adifferent feeling of how they
run their companies.
'cause they've learned thecustomer first ethos through
their careers that then theybring to their leadership as
(17:12):
well.
And the companies run by it.
If you're in the luxury worldwhere it's very high touch, it
lends itself to it.
I've seen a lot of the CEOs intravel very much in touch with
the frontline workers.
Travel has a lot of frontlineworkers, hotels, airlines, all
types of businesses, have a lotof frontline workers.
(17:32):
You have to be out there,experiencing what the frontline
people are experiencing for youto come back and then be able to
do it.
This is not directly in travel,but definitely related to
travel.
Dara Khosrowshahi who was theCEO of Expedia went to become
the CEO of Uber.
He's done interviews with us andalso to other media on how when
he started driving himself as anUber driver, did he really
(17:56):
connect the problems, thedrivers and the issues that
drivers have with Uber.
And was at least from a productlevel and was able to then come
back and say.
Guess what?
This problem has been there foryears.
Why didn't we solve it?
So I feel that understandingonly happens when you are the
front lines yourself.
How can you not be the chiefcustomer service officer in many
(18:17):
ways?
And so I embodied thatphilosophy myself, but I've also
seen that in a lot of people,accessibility matters,
particularly in this day andage.
I've talked about this before aswell.
Like you can't sit on an ivorytower and not be on, for
instance, social media, etcetera.
I do respect people who havezero social media just because
(18:40):
it's such a cancer in general.
If you're running a consumercompany, people see it through
very quickly, and so you have tobe communicating, I think those
who communicate in their ownlanguage.
I won't give an example of whathappened at the Global Forum,
like there was a bunch of CEOsand I interviewed many CEOs last
(19:01):
month at our goal forum.
I won't mention the one CEO, whodidn't come across well because
this person was very scripted,versus the CEOs who talk, in a
non-scripted way, and their PRpeople are scrambling by the
way, to pick up all the pieces.
I think you have a betterrespect for people who speak
their mind than people who and Iunderstand public companies have
(19:22):
responsibilities and you have toobviously, stay within certain
boundaries.
All the stuff I totallyunderstand.
But CEOs and leaders are as muchstorytellers as they are,
business leaders, decisionmakers, et cetera.
Last thing I'll say, the speedof decision making does matter.
(19:43):
In a day, you're making millionsmall decisions and I've always
said action over intent.
Always.
Always, and this is true for ourcompany, for my philosophy, but
it's also true for a lot ofother, general in any business
action or intent.
And businesses that I've seen dowell have, embodied that in many
(20:04):
ways.
David Kong (20:05):
Thank you for sharing all those very important
qualities that you want topossess as an exceptional
leader.
I totally agree with you oneverything that you said,
especially being genuine andaccessible and making decisions
expediently and being grounded.
Those are just wonderfulqualities.
Thank you for sharing all that.
(20:26):
Talking about exceptionalleader, you've always been
respected in the industry as aforward thinking, progressive
leader.
And I was wondering if you canshare some of the habits and
practices that help you staygrounded, creative, and
empowered.
Rafat Ali (20:43):
Yeah.
we're in the travel industry.
Travel is amongst the mostprogressive expressions of human
curiosity, like what is aroundthe corner?
Isn't that the most elemental ofhuman instincts?
I'm sure this was same for youwhen you were running Best
Western even now.
The most energized I am aboutSkift is when I'm out meeting
(21:04):
people, and bring back tons ofideas.
My team knows Rafat is on theroad.
He's gonna come back with 10ideas and our life is about to
get harder.
And also, one of the things I'velearned quite a bit every time
when I'm some distance awayfrom, 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 NewYork if I'm traveling, I still
(21:28):
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'mworking there, I'm away from
work.
So if I'm in Rome, which I waslast week for four or five days,
I have a renewed appreciation ofthe work that our team does
'cause I'm less hands on forthose four or five days.
(21:50):
And when I'm just readingstories from the outside or the
research from the outside, Isay, wow, this is really good
work our team does.
So I have a better appreciationof that.
The act or travel makes youcreative.
And grounded in the, in oh, wehave achieved something.
I have three young kids who aresitting downstairs quietly only
because they've been, they're ontv.
(22:11):
I have a 10-year-old and a6-year-old and a 5-year-old.
And I'm coming back from theGlobal Forum after all the
biggest CEOs I gathered bonetired and like I come home and
the three kids.
Jump on me and do not care a bitabout what has your dad done for
the last three days and you getgrounded because this is the
(22:31):
reality, as in I gotta make themdinner or, or, focus on them, et
cetera.
So certainly that keeps megrounded.
The other thing I'm very intouch with my heritage as an
Indian, origin person who wasn'tborn there, but my family's
there.
And and also I'm a practicingMuslim, so I think those two
(22:54):
personal parts of my existence,not that I keep them front and
center in my work, likeexplicitly, but it's a huge part
of my existence.
I think the immigrant mentalitythat I'm sure you will identify
with as well in this case inIndian immigrant certainly keeps
me grounded and I go back toIndia, so I just realize yes, we
(23:17):
have mobile phones there, weprobably have more mobile phones
and more cars there than USthese days, but we're still
taking bucket showers.
And the electricity still goesout.
Like the power still goes outfor an hour, two hours there.
And like the hawkers that usedto be there, selling vegetables
are still there.
(23:37):
And so it's incredible.
Like it's a whole differentexistence.
I fly 14 hours and I'm in awhole different world.
And so that keeps you grounded.
And it's just the joy of travelas we talked about, but also
just the incredible diversity ofthe world keeps you grounded.
David Kong (23:53):
You are absolutely right.
Thank you for sharing that too.
I don't want to keep you awayfrom the children for too long
'cause I know they haven't seenyou for a while and they're
gonna lose patience very soon.
Rafat Ali (24:04):
No.
So I'm gonna ask you
David Kong (24:05):
one last question.
Our show is about selfempowerment.
Rafat Ali (24:09):
Yeah.
David Kong (24:10):
What is the final advice that you can share with
our.
Rafat Ali (24:15):
Something I didn't do as much when I was younger,
primarily because I couldn'tafford 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 notpolitical, but listening to
contrarian ideas that you don'tagree with is an art developed
(24:40):
over a period of time.
You and I as young we're oh weare right.
Nobody, everybody else is wrong,but just listening to contrarian
ideas.
Or things that you don't agreewith or people that you don't
agree with.
Our country is a prime exampleof not listening to the other
person.
It does open up your mind.
(25:04):
One of the other things Ilearned about America when I
first came is ask and you shallget, if you don't ask, you won't
get it.
Which is a very interestingconcept coming from a Indian
culture where you have deferencefor authority.
Generally, you don't ask outtarespect.
But early on you gotta ask forthings.
(25:25):
Asking is a proxy to initiative.
And in our company, people whohave shown that they can paint
outside the lines, if you will,and raise their hands to do
things even though they may notbe part of their job
description, are the people whohave risen through the ranks
and, the last thing I'll say,and this is not an original
(25:48):
advice, but again, I'll go backto Dara.
Dara, the CEO of Uber did aninterview with LinkedIn, some
video thing that he did a fewyears ago.
And he had this concept ofcareer compounding, which is a
concept he borrowed from thefinancial compounding as in you
save money over a period of timeand then with interest and
stuff, it becomes, it's one ofthe most powerful concepts as in
(26:09):
finance and his concept ofcareer compounding is that what
young people do is they'rejumping from jobs to jobs to get
raises, et cetera.
His is that stair while in acompany, if you like it, and the
and learn the craft and.
(26:29):
Staying early in your career,staying at a company long enough
and early in your career willthen have exponential benefits.
We have examples in our companywhere Anne, who's my chief of
staff and also SVP of Growth isa live example.
She was at some other companyfor a year and a half before she
joined us, 23 years old backthen and has been with us for
(26:51):
eight years and has risenthrough the ranks, did sales, et
cetera, et cetera, and showedinitiative.
She is now one step away fromC-Suite at Skift or anywhere
else she wants to go if shedecides to.
It's only eight years of a lifein a long life yet to come and
(27:11):
she's 30 ish or whatever, andalready at the cusp of C-suite
in our company it's a greatexample of, in a small company,
if you like your job and if youput roots in and learn different
things over a period of time,you can then use that as a
catalyst for so many things.
(27:33):
So I was very taken when Darasaid this,'cause unconsciously I
was trying to do this with ourteam and then he put a name to
it, which was just great.
David Kong (27:42):
I absolutely love it! Love that career
compounding.
Rafat Ali (27:45):
It's such a great it's such a great advice and
it's contrarian and as likethese days everybody wants to
jump fast.
David Kong (27:52):
Yeah, it's worked for me.
Certainly if you look back at mycareer that is, and hospitality,
and
Rafat Ali (27:56):
by the way, I'm very impressed by, in general and
hospitality people have longcareers.
Many of the CEOs have been atthese companies for decades.
David Kong (28:05):
Yeah, that is true.
Your four pieces of partingadvice is so unusual.
I have not heard any one of themmentioned in my previous
interviews, but all four are sovaluable.
I like the career compounding.
I like ask and you shall receivebecause as immigrants we are
taught to just work hard andthings will take care of itself.
(28:26):
Yeah.
But it never does.
Have to be proactive and I likethat.
Travel broadens your horizon.
It is so true.
Everything that you said as yourfinal advice, it's just
fabulous.
Thank you.
Regrettably, we're coming to theend of our show, Rafat, thank
you.
I am most grateful that you'vetaken the time to be with us
(28:47):
today.
Rafat Ali (28:48):
Alright, thank you David.
David Kong (28:50):
Thank you.
And to our audience, if youenjoy this show, we hope you'll
join us on our website.
It's personal stories.com.
You'll find many otherinterviews on this website.
Thank you again for joining us.
Greetings.
I'm David Kong, the founder andprincipal of Its Personal
Stories.
We are the only podcast focusedon hospitality leaders telling
their personal stories.
Today, I'm delighted to welcomeRaha Ali.
He's a person that actuallyneeds no introduction because
most of us know him.
He is the founder and CEO ofskit.
(00:23):
Skit is the go-to.
Business intelligence platformfor the industry.
Many of us use it.
I, in my previous have, usedSkift for research and the
latest news.
So it's really an honor to haveyou Raffa,
Rafat Ali (00:37):
of course.
Thank you, David.
And I know our team has.
Spoken to you when you wererunning Best Western.
I've been following your podcastsince right when you launched,
and it's great to be on it.
David Kong (00:48):
It's great to have you.
Now, Raffa, you have a veryinteresting career journey.
You started as a journalist, youfounded paid content, and then
13 years ago, you founded Skift.
I was wondering if you'd be kindenough to share the choices and
risks that shaped your path.
Rafat Ali (01:08):
Yeah, I was born in uk, but grew up in India.
My father was a professor.
In those days, and this is trueeven now for Indian families,
parents want their kids to bedoctors, engineers, and lawyers.
My elder sister became a doctorand I was the second in line,
and so I had to become anengineer, even if I didn't want
to.
My parents pushed me into it.
(01:29):
I don't mean it in a negativeway.
That was the last time theypushed me.
And for all the choices that Imade since, they were hugely
supportive of it, which I'mhugely thankful for'cause it was
a big risk for me.
I went to school for, actuallybecame a computer engineer.
Engineering degree that I didwas in computers.
It was early days.
1992 is when I started thecourse.
(01:52):
The four year B Tech and cameout in 96.
And so back in those days, thecoders of the developers weren't
the rock stars that there aretoday.
And back in India in those days,you, we would basically be
working at an outsourcing firm,coding, which didn't sound very
(02:12):
glamorous to me, didn't soundvery fulfilling to me.
And so the choice that I madethen was that I wanted to go
into creative field, and so Icame across some advertising
copywriter that came from Delhito 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 bookson advertising in the university
(02:36):
library, all the classics ofgilian advertising, bunch of
others and moved to Delhi andtried to get a job.
Nobody took me seriously becauseI was a computer engineer.
So what are you doing inadvertising copywriting?
Why do you wanna earn one 10ththe salary that you would get as
a computer engineer?
And I went into PR at some PRagency as a junior person.
(02:57):
My job was to deliver printpress releases to media offices
back in Delhi and I got exposedto the journalist on the other
end and I said, oh, that's whatI wanna do.
I want to be a journalist.
Forget advertising copywriting.
So I applied.
I was one of the few journaliststhat really wanted to be in B2B
journalism,'cause youngjournalists or people who are
(03:18):
gonna school want the glamor ofthe big magazines.
Obviously things have changednow, but I was the one that
wanted to go deep into a sectorand focus on just being
hopefully being the mostinfluential force in the sector
that I choose.
And for me it's the one, one ofthe choices I guess I've learned
over the years is like, goingdeeper is better than going
(03:39):
wide.
You read as wide and you absorbas wide as you can'cause how
else will you then know theworld?
And then connect the dots deepinto the sector in travel.
And it reflects, I'm sure you'veseen it reflects in how we look
at the world of travel throughskit, which is everything
affects travel.
Travel affects everything, andwe have to look at it from a
(03:59):
wide angle lens and then godeep.
And so I think I learned thatover a period of time in my
career.
So I went into this trademagazine in India.
Web 1.0 was happening all overhere in Silicon Valley and U.S.
And I started writing internetstories about the internet scene
in India.
Early days realized the actionwas in us.
(04:22):
I applied for further studies inUS Masters and I got into
Indiana University, which iswhere I went for my master's,
Bloomington, Indiana.
There was a new media fellowshipthey had.
So I got a full ride, which I'mhugely thankful for.
My parents couldn't affordsending me to US.
That was the only way I could.
And that really set my careerand I stayed here, worked at a
(04:45):
couple of dot coms.
As a writer, like news mediacompanies and then started my
blog Paid content, which youreferenced that turned into a
media company.
So paid content was probably theearliest blog that turned
professional, as in bloggers inpajamas creating media
companies.
Wired did a story on me back in2003.
(05:07):
I think blogging for Bucks wasthe headline.
I didn't expect to become anentrepreneur, just had our
family, had no history of itwith academic family.
So I learned everything on thejob and lo behold, what is it
now?
2025.
So 25 years later, intoentrepreneurial media slash
(05:28):
information businesses that havecreated.
David Kong (05:32):
Wow, what a story.
Rafat Ali (05:33):
Yeah.
My story in a small way is onlypossible- for all the problems
that there is in America, isonly possible in America.
I still believe it.
David Kong (05:42):
Amen to that.
The world has changed a lot inthe last 13 years since you
founded skit, what was youroriginal vision for Skift and
how has that evolved over time?
Rafat Ali (05:54):
One of the earliest pitch decks that I wrote was we
want to create the Bloomberg oftravel.
So news, research, conferences,and cutting across different
sectors.
So as you very well know, sinceyou've spent your life in this
industry lots of hotel trades, alot of airline trades, et
cetera, et cetera, but nobodywas connecting the dots across
all these sectors.
Certainly nobody was looking atconsumer behavior and how that
(06:16):
was changing in an age ofdigital and mobile, and now
obviously ai, et cetera.
So my contention was there needsto be a Bloomberg of travel for
this age.
And so that original vision hasdefinitely played out.
Meaning we wanted to raise themetabolism of coverage in the
industry for being as big and asinfluential as it is.
(06:38):
You very well know this.
From a policy perspective on geoparticular perspective, it
punches below its weight in allpossible ways on a global scale,
on a national scale, on aregional level, et cetera.
In fact the lack of travel as inclosing borders and visas is
what everybody leads with, asthese days, unfortunately.
So part of the mission washonestly, because I came as an
(07:02):
outsider was this naive visionof we gotta raise the
metabolism, the industry and putto its rightful place in the
world by the virtue of coveringit, instead of a forward
digital, forward, less jargon,more designed forward, more
experience, forward coverage ofthe industry.
(07:23):
If I can humbly say so.
I think we've done our part init.
I think it's still a lot to gofrom a policy and global
influence of travel industryperspective.
But we certainly, that's aunderlying mission, even if it's
not a direct part of what I talkof what we talk about elevate
the industry.
Additionally, we wanted to alsogo into the cons, let's first
(07:45):
try B2B media news coverage ofthe industry, and then we will
create a consumer site that isaimed at prosumer travelers,
business travelers, people whoare expert travelers.
That part didn't happen.
We just got too busy with the,with just creating the industry
(08:06):
information thing.
But how we write in a lessjargon, more forward looking
way.
We do have readers who are notfrom the industry, but it's not
a business for us.
We don't get any money fromthem.
We don't aspire to get any moneyfrom them.
So that part got put by thewayside.
We tried initially to createsome data services.
We didn't know what we weredoing and this was early days of
(08:29):
social media, and so we had someindex of which brands were best
as social media and then thesocial media companies clammed
down on free access to theirAPIs and all this other stuff
happened.
So we failed at that.
We moved into the business ofrestaurants, Skift Table.
We acquired this smallrestaurant tech newsletter with
(08:49):
an idea that, what we've done intravel, we'll do in the f and b
world.
Lots of connections, at least onpaper between f and b and
hospitality particularly didn'tsucceed.
We did for about a year and ahalf, and I shut it down in
summer of 2019.
We also moved a little bit intobusiness of wellness.
We started a newsletter with anidea that travel, restaurants
(09:12):
and wellness is the business ofleisure where disposable income
is spent on paper's.
Not like great idea.
It's just that there's so muchto do in travel that in
hindsight, that was the rightdecision.
For us to just go deeper anddeeper.
So it's changed.
We've done things that work,things that didn't work.
And as any company does.
David Kong (09:33):
That's great.
You try new things that didn'twork, you move on and you learn
from it.
I always believe that ourhardships and setbacks are
actually great learningopportunities.
So in that vein, would you mindto share some of the toughest
challenges that you have facedin building Skift and the
lessons that taught you aboutresilience and leadership?
Rafat Ali (09:54):
Yeah.
Oh man.
Oh my goodness.
as you already know, our lessonsare as much travel industry
lessons as it is skiff lessons.
'cause obviously we are ahundred percent focused on the
industry, but early on we raisedsome venture funding.
So we raised about$3 million aseed when we started the
company, Jason, who's myco-founder, and I launched it
(10:15):
back in 2012.
And so we raised some seedfunding with an idea that will
create news and this consumerthing that I just mentioned and
these data services, and we'llraise more money to do more and
scale quickly like any venturebacked startup.
We failed at raising the nextround series A.
I was out on the road 2013 or2014, pitched, I don't know, 50,
(10:39):
70, 80 investors.
None of the investors believedin our vision.
There are investors willing toinvest.
We just couldn't get a lead.
As it is in all startups.
You find a lead and then otherswill follow.
Didn't happen.
At some point in 2014, we justdecided to bootstrap from there.
And so I call Skift, TheBootstrap plus company as we did
(10:59):
raise a little bit of money, butit's been 13 years in and we do
have investors, but again, theseare small amounts and investors
beyond a certain point.
I don't have a board that had ahuge effect in how we build a
company, which is you have toessentially, eat what you kill.
This is a Zuckerberg phase.
'cause apparently Zuckerbergonly eats animals that he kills
(11:20):
himself.
And I forget the whole contextof it.
The creativity that comes withnot having tons of resources, in
my opinion, outweighs anythingthat with tons of money you can
do.
And so that's always been ourphilosophy.
Like one step at a time, twosteps at a time.
We take risks.
And the ability to take risks islower in the sense that we just
(11:43):
don't have that much cash.
But then you become creative andthey risk in different ways.
So certainly that was a hugepart.
And since then I've become a bigadvocate of not raising too much
money for startups in generalthat don't need to, particularly
media information companies.
Creative type startups'causethey may not be venture backed
(12:04):
businesses to begin with, right?
They may not have the venturereturns that venture capitalists
are looking for.
So certainly that was a big one.
COVID was another one, obviouslyfor all lessons that you learned
during COVID, we learned duringCOVID as well.
I had to lay off one third ofthe staff.
That was tough.
We were 60 people down from 40.
These 20 people, 21, 22 peoplethat we laid off were laid off
(12:27):
for no fault of theirs.
We had to survive.
We had a very senior HRconsultant that was working with
us to help us set up HR moreformally after many early years.
she was the former HR head ofNew York Times.
So a lot of the experience.
So as we're trying to figure outhow to come up with the list.
We cut the office, we cut thesoftware, we cut everything we
could cut before we came to ourteam.
(12:50):
And she had this idea let'sinclude the people as in ask the
team for voluntary furloughs.
I've heard this in many largercompanies, but as a small
company, it was very meaningfulbecause a bunch of people raised
their hands.
I'll go one, I'll go three daysa week.
I'll go four days a week etcetera, et cetera.
(13:11):
So that was really we stilldidn't save us enough.
We still had to lay off a bunchof folks, but initially the
furlough and then we had to letthem go.
But including people in yourdecisions was really a big part
of how I learned it from likeinstead of top down, including
people even in the harddecisions.
It was one of the biggestlessons I learned from that
(13:32):
bunch of other crisis is we,Silicon Valley Bank, if you
remember happened Oh, yeah.
Two years ago.
David Kong (13:37):
Yeah.
We
Rafat Ali (13:37):
had every cent of our money in Silicon Valley Bank.
David Kong (13:41):
Oh no.
Rafat Ali (13:43):
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 comparedto Silicon Valley Bank.
Every cent of your moneydisappearing.
We had$7 million in the bankaccount and it went to zero.
We tried to get our money outand we were too slow.
(14:03):
Then money came back'causePresident Biden, whatever said,
you have to rescue thesecompanies and the bank, et
cetera.
We didn't know.
And the lesson I learned, and Iwrote about it too was that you
have to take emotions out insuch a short time if you make
these big decisions.
There was a grief period, likethere was one time where I
(14:24):
called my president.
Called her and I just brokedown.
I cried.
I said, we're done 11 years ofwork, it's over.
And I did not know about bankrescues, et cetera.
Didn't have the history ofunderstanding that it was gonna
be okay.
'cause at some point thegovernment generally steps in.
I didn't have that concept.
(14:44):
What I wrote is if there isgrief for a period of time, shut
down your emotional brain andthen shift to your execution
brain.
We created a virtual war room asin a zoom group of the five, six
people in the company.
We figured out how to do thepayroll.
The next payroll.
And then by the time we had tofigure that out, it was all
(15:06):
happening on a weekend.
Nobody else in the team, in thecompany of like at that point
must have been 70 people orsomething, had any idea.
They were reading the news.
Our team didn't understand ordidn't know we had a bank
account in Silicon Valley Bank.
Some of the salespeople knew, etcetera, et cetera.
But not everybody knows, likewhy would editors know that we
have a bank account in SiliconValley Bank?
(15:28):
So at some point, you have toinsulate people in your company.
You have to shield them fromcreating panic.
Those are some of the thingsthat I learned over the years.
David Kong (15:40):
Thank you so much for sharing those challenges and
the very valuable lessons thatyou learned from them.
Wonderful lessons! Now let'sswitch gears.
You have interviewed many veryrespected and accomplished
leaders, and you've alsointeracted with many others.
What are some of the qualitiesthat set apart the truly
(16:02):
exceptional leaders?
Rafat Ali (16:04):
I have a bias for founder led companies.
Founder led companies have adifferent level of passion and
intensity.
A lot of us are intense people.
You meet Brian Chesky you areoverwhelmed in half an hour
talking to him because he'screated something iconic out of
nothing.
so I have a affinity to founderled businesses.
(16:26):
He came out with the foundermode philosophy last year that
became viral of like as big asthe company is, the founders
have to be hands on and how canthey not be chief product
officers of their companies?
He didn't mean literally, but itmetaphorically meant that you
have to be hands-on with theproduct.
I have an affinity for hotelierCEOs.
(16:49):
People that rose through theranks and many of them, as you
very well know, have risenthrough the ranks.
And hotelier CEOs, particularlythose on the sort of luxury end
of the world, just have adifferent feeling of how they
run their companies.
'cause they've learned thecustomer first ethos through
their careers that then theybring to their leadership as
(17:12):
well.
And the companies run by it.
If you're in the luxury worldwhere it's very high touch, it
lends itself to it.
I've seen a lot of the CEOs intravel very much in touch with
the frontline workers.
Travel has a lot of frontlineworkers, hotels, airlines, all
types of businesses, have a lotof frontline workers.
(17:32):
You have to be out there,experiencing what the frontline
people are experiencing for youto come back and then be able to
do it.
This is not directly in travel,but definitely related to
travel.
Dara Khosrowshahi who was theCEO of Expedia went to become
the CEO of Uber.
He's done interviews with us andalso to other media on how when
he started driving himself as anUber driver, did he really
(17:56):
connect the problems, thedrivers and the issues that
drivers have with Uber.
And was at least from a productlevel and was able to then come
back and say.
Guess what?
This problem has been there foryears.
Why didn't we solve it?
So I feel that understandingonly happens when you are the
front lines yourself.
How can you not be the chiefcustomer service officer in many
(18:17):
ways?
And so I embodied thatphilosophy myself, but I've also
seen that in a lot of people,accessibility matters,
particularly in this day andage.
I've talked about this before aswell.
Like you can't sit on an ivorytower and not be on, for
instance, social media, etcetera.
I do respect people who havezero social media just because
(18:40):
it's such a cancer in general.
If you're running a consumercompany, people see it through
very quickly, and so you have tobe communicating, I think those
who communicate in their ownlanguage.
I won't give an example of whathappened at the Global Forum,
like there was a bunch of CEOsand I interviewed many CEOs last
(19:01):
month at our goal forum.
I won't mention the one CEO, whodidn't come across well because
this person was very scripted,versus the CEOs who talk, in a
non-scripted way, and their PRpeople are scrambling by the
way, to pick up all the pieces.
I think you have a betterrespect for people who speak
their mind than people who and Iunderstand public companies have
(19:22):
responsibilities and you have toobviously, stay within certain
boundaries.
All the stuff I totallyunderstand.
But CEOs and leaders are as muchstorytellers as they are,
business leaders, decisionmakers, et cetera.
Last thing I'll say, the speedof decision making does matter.
(19:43):
In a day, you're making millionsmall decisions and I've always
said action over intent.
Always.
Always, and this is true for ourcompany, for my philosophy, but
it's also true for a lot ofother, general in any business
action or intent.
And businesses that I've seen dowell have, embodied that in many
(20:04):
ways.
David Kong (20:05):
Thank you for sharing all those very important
qualities that you want topossess as an exceptional
leader.
I totally agree with you oneverything that you said,
especially being genuine andaccessible and making decisions
expediently and being grounded.
Those are just wonderfulqualities.
Thank you for sharing all that.
(20:26):
Talking about exceptionalleader, you've always been
respected in the industry as aforward thinking, progressive
leader.
And I was wondering if you canshare some of the habits and
practices that help you staygrounded, creative, and
empowered.
Rafat Ali (20:43):
Yeah.
we're in the travel industry.
Travel is amongst the mostprogressive expressions of human
curiosity, like what is aroundthe corner?
Isn't that the most elemental ofhuman instincts?
I'm sure this was same for youwhen you were running Best
Western even now.
The most energized I am aboutSkift is when I'm out meeting
(21:04):
people, and bring back tons ofideas.
My team knows Rafat is on theroad.
He's gonna come back with 10ideas and our life is about to
get harder.
And also, one of the things I'velearned quite a bit every time
when I'm some distance awayfrom, 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 NewYork if I'm traveling, I still
(21:28):
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'mworking there, I'm away from
work.
So if I'm in Rome, which I waslast week for four or five days,
I have a renewed appreciation ofthe work that our team does
'cause I'm less hands on forthose four or five days.
(21:50):
And when I'm just readingstories from the outside or the
research from the outside, Isay, wow, this is really good
work our team does.
So I have a better appreciationof that.
The act or travel makes youcreative.
And grounded in the, in oh, wehave achieved something.
I have three young kids who aresitting downstairs quietly only
because they've been, they're ontv.
(22:11):
I have a 10-year-old and a6-year-old and a 5-year-old.
And I'm coming back from theGlobal Forum after all the
biggest CEOs I gathered bonetired and like I come home and
the three kids.
Jump on me and do not care a bitabout what has your dad done for
the last three days and you getgrounded because this is the
(22:31):
reality, as in I gotta make themdinner or, or, focus on them, et
cetera.
So certainly that keeps megrounded.
The other thing I'm very intouch with my heritage as an
Indian, origin person who wasn'tborn there, but my family's
there.
And and also I'm a practicingMuslim, so I think those two
(22:54):
personal parts of my existence,not that I keep them front and
center in my work, likeexplicitly, but it's a huge part
of my existence.
I think the immigrant mentalitythat I'm sure you will identify
with as well in this case inIndian immigrant certainly keeps
me grounded and I go back toIndia, so I just realize yes, we
(23:17):
have mobile phones there, weprobably have more mobile phones
and more cars there than USthese days, but we're still
taking bucket showers.
And the electricity still goesout.
Like the power still goes outfor an hour, two hours there.
And like the hawkers that usedto be there, selling vegetables
are still there.
(23:37):
And so it's incredible.
Like it's a whole differentexistence.
I fly 14 hours and I'm in awhole different world.
And so that keeps you grounded.
And it's just the joy of travelas we talked about, but also
just the incredible diversity ofthe world keeps you grounded.
David Kong (23:53):
You are absolutely right.
Thank you for sharing that too.
I don't want to keep you awayfrom the children for too long
'cause I know they haven't seenyou for a while and they're
gonna lose patience very soon.
Rafat Ali (24:04):
No.
So I'm gonna ask you
David Kong (24:05):
one last question.
Our show is about selfempowerment.
Rafat Ali (24:09):
Yeah.
David Kong (24:10):
What is the final advice that you can share with
our.
Rafat Ali (24:15):
Something I didn't do as much when I was younger,
primarily because I couldn'tafford 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 notpolitical, but listening to
contrarian ideas that you don'tagree with is an art developed
(24:40):
over a period of time.
You and I as young we're oh weare right.
Nobody, everybody else is wrong,but just listening to contrarian
ideas.
Or things that you don't agreewith or people that you don't
agree with.
Our country is a prime exampleof not listening to the other
person.
It does open up your mind.
(25:04):
One of the other things Ilearned about America when I
first came is ask and you shallget, if you don't ask, you won't
get it.
Which is a very interestingconcept coming from a Indian
culture where you have deferencefor authority.
Generally, you don't ask outtarespect.
But early on you gotta ask forthings.
(25:25):
Asking is a proxy to initiative.
And in our company, people whohave shown that they can paint
outside the lines, if you will,and raise their hands to do
things even though they may notbe part of their job
description, are the people whohave risen through the ranks
and, the last thing I'll say,and this is not an original
(25:48):
advice, but again, I'll go backto Dara.
Dara, the CEO of Uber did aninterview with LinkedIn, some
video thing that he did a fewyears ago.
And he had this concept ofcareer compounding, which is a
concept he borrowed from thefinancial compounding as in you
save money over a period of timeand then with interest and
stuff, it becomes, it's one ofthe most powerful concepts as in
(26:09):
finance and his concept ofcareer compounding is that what
young people do is they'rejumping from jobs to jobs to get
raises, et cetera.
His is that stair while in acompany, if you like it, and the
and learn the craft and.
(26:29):
Staying early in your career,staying at a company long enough
and early in your career willthen have exponential benefits.
We have examples in our companywhere Anne, who's my chief of
staff and also SVP of Growth isa live example.
She was at some other companyfor a year and a half before she
joined us, 23 years old backthen and has been with us for
(26:51):
eight years and has risenthrough the ranks, did sales, et
cetera, et cetera, and showedinitiative.
She is now one step away fromC-Suite at Skift or anywhere
else she wants to go if shedecides to.
It's only eight years of a lifein a long life yet to come and
(27:11):
she's 30 ish or whatever, andalready at the cusp of C-suite
in our company it's a greatexample of, in a small company,
if you like your job and if youput roots in and learn different
things over a period of time,you can then use that as a
catalyst for so many things.
(27:33):
So I was very taken when Darasaid this,'cause unconsciously I
was trying to do this with ourteam and then he put a name to
it, which was just great.
David Kong (27:42):
I absolutely love it! Love that career
compounding.
Rafat Ali (27:45):
It's such a great it's such a great advice and
it's contrarian and as likethese days everybody wants to
jump fast.
David Kong (27:52):
Yeah, it's worked for me.
Certainly if you look back at mycareer that is, and hospitality,
and
Rafat Ali (27:56):
by the way, I'm very impressed by, in general and
hospitality people have longcareers.
Many of the CEOs have been atthese companies for decades.
David Kong (28:05):
Yeah, that is true.
Your four pieces of partingadvice is so unusual.
I have not heard any one of themmentioned in my previous
interviews, but all four are sovaluable.
I like the career compounding.
I like ask and you shall receivebecause as immigrants we are
taught to just work hard andthings will take care of itself.
(28:26):
Yeah.
But it never does.
Have to be proactive and I likethat.
Travel broadens your horizon.
It is so true.
Everything that you said as yourfinal advice, it's just
fabulous.
Thank you.
Regrettably, we're coming to theend of our show, Rafat, thank
you.
I am most grateful that you'vetaken the time to be with us
(28:47):
today.
Rafat Ali (28:48):
Alright, thank you David.
David Kong (28:50):
Thank you.
And to our audience, if youenjoy this show, we hope you'll
join us on our website.
It's personal stories.com.
You'll find many otherinterviews on this website.
Thank you again for joining us.
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