← The Messy Parts
The Messy Parts
Rafat Ali Plays the Long Game: This Internet Pioneer Says You Should Stop Rushing Your Career
00:36:40
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- [00:00]
A
How did you know that was a moment to push through versus to say, like, I'm gonna call it. Cause sometimes there's a moment you should call it.
- [00:07]
B
Yeah. In hindsight, some of the lessons that have sort of crystallized, if you will, the ways to look at phases in life, Give it two years. Like, if you're starting a new business, give it two years. If you're starting a new relationship, I mean, if it lasts two years, that's great. So for me, increments of time have helped. Like I give myself X months.
- [00:30]
A
That's good. Adv.
- [00:32]
B
Foreign.
- [00:38]
A
The messy parts we have on Rafat Ali. He's the CEO and founder of Skift, which is a travel media platform that's global. He looks like he's had an incredible ride if you go to LinkedIn. He sold his first company after having moved from India to Indiana, where he was a night fellow and just had a hockey stick ride in the world of media today. But when you get him on the couch, there's a lot of messy pivots and turns along the way and he opens up in a way that apparently he's never done before. Can't wait for you to actually listen to Rafaeli. I'm so excited for this conversation. You and I got to know each other when I was at Hyatt and obviously you had skiffed. And I remember being so impressed with the media platform that you had built. I said then, and you can correct me now because it's been many years that you were kind of like fast company for the travel industry. It was a much more innov innovative, forward looking media platform. It's so great to have you on because the thing I love is that I might know you, but then I get to do lots of research on you, which you know is good and bad for you. What's interesting is we have a bit of similarities in our background, which you may or may not know because you haven't had, you know, three days of research. And you know, I grew up in Iran. You grew up in India. You grew up in an Indian family, a Muslim family. Like all Iranians, they want us all to be computer scientists, doctors or engineers.
- [01:59]
B
Exactly what happened.
- [02:01]
A
And you actually did listen, which I did not. You listened to your parents first and last time.
- [02:06]
B
No, not first, last time. Not first time. Last time.
- [02:08]
A
Okay. And you know, we know a lot of people who do. And you go to study computer science and engineering and somewhere in year two you have this existential crisis and you think, what am I doing? I actually want to do something more creative.
- [02:22]
B
Yeah.
- [02:23]
A
Why don't you tell me a little bit about that? Because that had to have been complicated.
- [02:26]
B
I always had the sort of daydreaming part of me that wanted to do something creative. I mean, this was. I was young, didn't know what that meant. In hindsight, that seems like what it is. Wanted to go into geography, which if you come full circle, I'm now in travel, so we can talk about that. I wanted to do English, which is why I guess I became a journalist at some point. So I met a copywriter who had come from Delhi to the small town that I lived in. And it seemed just so glamorous. Kind of like Mad Men visions.
- [03:00]
A
Advertising was glamorous in those days.
- [03:02]
B
Yeah. Like the actual copywriting. Yeah, part of it. And I said, that's what I want to do. I wanted to do an MBA in advertising so at least it would take care of some of their aspirations of MBAs, engineering, MBA. But I would have my love for advertising applied to a couple of schools that were good in India. Got wait listed in one. So there was one trade magazine in India for advertising. It was called A and M, which is short for advertising and marketing, basically the ad age of India. And I was reading it to learn about the industry. So I said, okay, I couldn't get into this MBA program. I should apply to be a writer for this magazine. I wrote a letter to the editor. In major parts of my life, I've written my way into something or written my way out of trouble.
- [03:49]
A
Were you a writer as a child? Like, when did the pen become your thing?
- [03:54]
B
I used to stammer till I was 17 year old. Stutter. What they call here, stammer, I guess is the British word. And I was a weak kid because I had asthma as a kid as well. So asthma, stammer. So low on confidence. For me to speak and not stutter a certain word, I had to come up with an alternate word. So my vocabulary as a result increased. I think that that had at least a contributory factor to me being quiet. So I would express myself in writing.
- [04:22]
A
Part of how we do the podcast is, you know, you have this interesting career, right. And if I look at it on LinkedIn, it's like a hockey stick up and to the right. It looks great. Perfect.
- [04:33]
B
Yeah.
- [04:33]
A
I don't know exactly. That's how it looks on social media, as we know and yet we know there were many moments that were messy. I. I like to say most of the moments were messy. And then there's these Moments that are real pivot moments. And then you decide journalism is your moment and you get a night fellowship and you end up at Indiana University.
- [04:52]
B
Yeah, from India to Indiana, not like each other.
- [04:54]
A
India to Indiana.
- [04:55]
B
Yeah.
- [04:56]
A
I say from Tehran to Paris to Lafayette, California, which is not Indiana, but, you know, it was.
- [05:02]
B
Yeah, this is 99. And for me, cable TV had just come into India like a few years before I left. So literally this, this sounds so ridiculous when I say this, but like to me, us was Baywatch.
- [05:14]
A
For me it was Brady Bunch. So, yeah, the Osmonds.
- [05:17]
B
Yeah. So the first six months were miserable. When I got there, hard adjustment coming from India. My parents at that point were living in Saudi, came to Indiana, and within the first few weeks, I said, this is ridiculous. I want to go back. And as a Muslim brown kid from India who didn't drink party, it was hard for me to adjust. I remembered that I broke down on the phone talking to them and my mom got worried. And my dad was the strong and silent types, sort of the professor, professor in biochemistry in India. The most he ever talked to me was he wrote this letter to me, which is a seven page letter that I discovered that I rediscovered like 2017 or something in my house back in India. The gist of it was, you are lucky that you've left India. You should make your own way of life, way in life, as opposed to depending on others to fill it. I had forgotten about this letter until I rediscovered in 2016, 2017.
- [06:26]
A
You block things out.
- [06:27]
B
I do block things out. I mean, isn't it a great skill to have?
- [06:32]
A
I recognize that in you because I do that myself.
- [06:35]
B
It's a great skill to have.
- [06:36]
A
Yes. Because I can hold on to all those things.
- [06:38]
B
Compartmentalize.
- [06:39]
A
I guess compartmentalized.
- [06:42]
B
Is the better word. But where was I? You get the letter? Yeah. When I rediscovered it in 2016, 2017, and my dad was still alive then, I knew I was going to be very meaningful to me when at some point he passes away, which he did in 2019. Turns out all the stuff that he asked me to do, either consciously, unconsciously, I have lived 20 plus years after.
- [07:09]
A
I went and read that letter because I came across this.
- [07:12]
B
Yeah, I posted it.
- [07:13]
A
Yeah, you did a medium piece. And I actually wrote down a couple of the lines. He said, stay focused on your goals. Don't get distracted by temporary setbacks. You have been given an opportunity. See it through even when it's hard. Create your own space, make your own meaning into your daily existence. And take the bull by the Horns. I mean, it was kind of a prolific letter, but it was definitely also like, I was like, he's tough.
- [07:40]
B
Yeah.
- [07:41]
A
I mean, there wasn't like a lot. I mean, there was empathy mixed in, but this sense of like, you've been given an opportunity, focus on your goal, go do it. Yeah.
- [07:50]
B
And a lot of like a Indian parent.
- [07:52]
A
Yeah.
- [07:53]
B
Type mentality. Yeah.
- [07:54]
A
The story for me goes that my mom, I was an accident. So I was. She had me when she was 20 and she had gotten a scholarship for a graduate program at Northeastern. And so she leaves her one year old and her new husband and comes to study by herself in Boston, very lonely. But there was this sense that, like, you were given this opportunity, like you had to do something with it and you did.
- [08:20]
B
Yeah.
- [08:20]
A
You toughed it out.
- [08:21]
B
Yeah. I didn't want to disappoint my parents. I think that's the main part of it. The thing that journalism school gave me, not so much that the academics was great, but it was my entry point into America. Right. For me, learning the culture of America, one of the things I did, I found this one friend, Greg. He was from Louisville, Kentucky, so from Indiana to Kentucky. A self professed redneck himself. Not my word. I had to learn what redneck meant. I said, like is your. What does it mean? Like, your neck is red. He was my guide into the American culture. We were watching the late night shows together. So you start with Jay Leno and then you sort of graduate to Letterman, sort of in terms of edginess of humor and edginess of commentary. And also as a student of media, learning about the American culture by how people react to what's on tv. It's changed now, but back in the days, it was still the age of mass media. So how people react to what's on TV is. There was a surefire way of learning what American culture was. I was very much. I wanted to learn as much about American culture in my year and a half that I was there.
- [09:28]
A
So you graduate, but there's a moment where you actually decide to push through and then you do. How did you know that was a moment to push through versus to say, like I'm going to call it, because sometimes there's a moment you should call it.
- [09:40]
B
Yeah. In hindsight, some of the lessons that have sort of crystallized, if you will, the ways to look at phases in life, give it two years. Like if you're starting a new business, give it two years. If you're starting a new relationship, I mean, if it lasts two years, that's great. So for me, increments of time have helped. Like I give myself X months. That's good advice, particularly from a business perspective. Like even in our company, if we launch something new, it takes two years for things to establish. Conferences usually takes between two and three years for it to be established on the circuit. This was a thing for me that took some time to learn. What does that mean? That means that people put in the calendars every year, because otherwise, if it's just a new conference and you move from topic to topic, like one year it's this conference, the next year it's a totally different topic. There's some value in the novelty of the idea, but the reality is the world works in many ways on inertia, repetition. Your goal is to be part of that repetition. My first company, Paid Content, if you remember, was a blog that turned into media company. From blog it turned into first a newsletter. Email newsletter. Email newsletters are now a very known thing. Back in those days, I learned the power of the daily email landing in your inbox. I worked briefly for this magazine here in New York or Silicon Valley Reporter. I'm jumping ahead a little bit. I saw the power of what a newsletter can do, the daily habit that it becomes. And if you're good enough, people read it, open it every day. What is now called a parasocial relationship, which is you as a podcaster. People identify with you almost like they're part of your network. Email had that intimacy. Still has.
- [11:30]
A
Well, one on one, somebody can reply.
- [11:32]
B
Yeah. And so I saw the power of that married to the metabolism of the blogs and that the promise that every time you come on the blog, there'd be something new. And so for me, that was very powerful in terms of creating that daily habit with people. And so your goal with Skift and my previous company has always been how do we become of daily utility value to our readers? The biggest thing is from nice to have to must have.
- [11:59]
A
You're.
- [11:59]
B
You've learned this lesson, I'm sure, in every company you work with. How do you go from nice to have to must have?
- [12:05]
A
And there's a lot of options now.
- [12:06]
B
There are tons of options. So you know my love for B2B media, which is unlike a lot of other journalists who dream of working at magazines or back in the days, now has changed. I always wanted to be in B2B media.
- [12:21]
A
Why?
- [12:22]
B
Influence. I don't know how that came about, but I wanted to be the most influential force in a specific sector.
- [12:31]
A
I think most people go broad and you picked a niche. That was actually part of your strategy. When I look back over your history, having done the research, I saw these threads, you didn't just start businesses, you started businesses and had a blog on the side at the same time.
- [12:45]
B
There's no shortcut in life. I know it's such a cliche to say, but I have family and friends who are always looking to either get rich quick or have success fast. I just know no other way than to take the long way into anything. By the way, my travels also reflect that unconsciously, which is that I always want to take the long way only because it's just a lot more interesting. I have this travel philosophy, which my wife laughs at, but it's like when you land in an airport, if everybody's taking a right, you take a left, you will end up probably coming around in a loop to the right. But it's just like, literally, I can trace Iceland the exact same. When I travel Iceland for the first time, when I travel Mongolia for the first time, everybody goes to west Mongolia. I went to east Mongolia first.
- [13:37]
A
What do you think it is about you? Because you are a bit of a contrarian.
- [13:41]
B
Yeah, I don't know. Contrarians can sometimes be douchebags. Like, you know, they're professional.
- [13:46]
A
You're not a douchebag. I can say that with certainty.
- [13:48]
B
You know, some of the writers that you and I know could be called contrarian douchebags. It's like my quest to be different, but not for the sake of being different.
- [14:00]
A
Well, you know, it's interesting because I think you are also an outsider, and.
- [14:03]
B
A lot of that are looking in.
- [14:04]
A
Yeah, you were an outsider looking in. And when I look at your business and sort of your trajectory, I'm also struck by how you had the ability to see global landscapes versus just us landscapes.
- [14:15]
B
I just didn't realize there was this much therapy involved in this. In this podcast. In this podcast. I'm a little unnerved, but.
- [14:23]
A
Yes, you were never unnerved. That is just not with me.
- [14:27]
B
No, I was not expecting to have to, like, go into the crevices of my brain to come up with.
- [14:34]
A
But think about it. How can we be useful? We've both sat in these crazy seats that look amazing and successful from the outside. We. We both know how hard it is. I say to people all the time, there's not a person who doesn't come on this couch, who doesn't just work just crazy hard. Right? That's the baseline. And then there's luck and a bunch of other things involved. But the point of doing the podcast to talk about the messy parts is to open up what we learned from the journeys as tips for other people. Because there's somebody listening who's either been laid off or decided to step away from a business or had a bad deal or who could use a little bit of the actual how did you put one foot in front of the other? Because I'm curled up like a ball and I can't get out of my bed just now. Moment.
- [15:18]
B
One of the biggest lessons I've learned in hindsight, again, the power of longevity, both in terms of my own company. I'm 13 years into the company, which in Internet terms is a long time.
- [15:31]
A
Dog years.
- [15:32]
B
Yeah. And I still have investors in my cap table who've been very patient. My first company, the blog, turned into a media company, paid content, got sold to Guardian at some point.
- [15:44]
A
And then you took two years off.
- [15:45]
B
And then I took two years off, lasted about 11 years. I was there eight years. But the company lasted about 11 years. It was sold to Guardian, Guardian sold to somebody else. That company shut down. I'm also the same fan of longevity of people who stick with me in my company. So I don't know if you know Dara, your Dara Kostroshavi this year. Uber was at Expedia before, so we know him very well from the travel industry. And Uber still is in travel. He said something on some LinkedIn interview with the CEO of LinkedIn. He did this thing, this concept of career compounding, which is a term that stuck in my head since I heard it a few years ago, as in compound interest of the very powerful phrase in finance and applied to careers, as in what the young people do today is they jump from job to job early, you know, quick year, two years, in an attempt to climb the ladder. His advice is the total opposite, which is don't be in a rush, put your roots, hone your craft. When you're ready to fly the cooperation, then you're in exponential position to jump way ahead than others who've been jumping from ladder to ladder, which is something that I've taken very seriously and very internally with my team.
- [17:07]
A
You have people who've worked with you.
- [17:08]
B
Repeatedly for many years from the start. But I'll give one example because examples will hopefully be helpful. Anne, who's my chief of staff but is now SPP of growth, must be in her early 30s, came out of Yelp, was like a year and a half. Started us as a junior salesperson, has stayed with me for eight Years, which is I think more than one fourth of her life, maybe one third of her life. When she joined, must have been 25 people now, or almost 100 people. Has learned pretty much everything, has seen everything, by the virtue of sticking around and raising her hand at different times to say, rafat, I can do this. Beyond her current job, has put herself in a position where she's one level below sea level today and will be very soon in the C level. She's early 30s. She leaves Skift. She'll be a C level anywhere she wants to be. Anywhere. Point is that career compounding is such a powerful concept. As in like 5, 6, 7, 8 years in your 20s to early 30s will set you up. Of course, assuming this is a nurturing company, this is a company that you.
- [18:12]
A
Think you like to say. As I hear you talking, I'm like, I had a career column and somebody was like, how do I know when to leave a job? Who's toxic? Right? I mean, there's many versions of this equation.
- [18:23]
B
Yes. I can only talk about my company.
- [18:25]
A
As in, already you're nurturing enough that you're saying, here's a pathway. I know you've tapped out here. So I would say if you can work for somebody who cares and is willing to care about you beyond just.
- [18:36]
B
And smaller companies generally.
- [18:38]
A
Yeah.
- [18:39]
B
I mean, my bias is towards one private sector, two smaller companies. And as a small company, it's not like I have path for everybody in the company because it's just not humanly possible. So many of them we go up to and say, I think this is, you know, this is over. I think it behooves us for them to, to go. Even if we lose the talent immediately, we have to find somebody else. So I've done that many times with people in our company. I think they will remember that for the rest of their lives.
- [19:06]
A
It's like you're an accumulation of your experiences and also your network. Right. So if you're good in that moment to somebody, they will remember that when they move on to the next thing, it becomes like an extensive alumni network.
- [19:19]
B
In our case, some of them end up at other travel companies and then they spend money with us in advertising or research or subscriptions or whatever else it is.
- [19:27]
A
So since you're generally good at looking around corners, if you were starting out now or if you were in mid career, what would you want to do?
- [19:34]
B
Not be a journalist, not be in media, not be a journalist. Whenever I got a chance, I used to go to journalism schools to give lectures because I felt like I was giving them a hopeful version of what you can do if you look beyond sort of the traditional careers. The last year, two years, it's been hard for me to go in with a straight face and say things will be great. It's just, it's bad as you know.
- [20:02]
A
Do you think it's bad for media or just for journalism?
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B
I think journalism particularly, there are no jobs or I mean this is. I'm talking even pre chatGPT coming in. Now obviously with GPT coming in it's hard unless you super specialize in a subject matter. The good part is obviously as an entrepreneur you can do a lot more because everything exists upstack, everything else. You know, tons of tools available, tons of ways to break through YouTube. We're just talking on this podcast that is breaking through on YouTube. Like how can you not have audio video these days as part of what you're trying to do?
- [20:40]
A
The barrier to entry is much less than when we started. I mean when we started you wrote for the New York Times or you didn't have a job. Yeah, right. I mean there weren't that many places.
- [20:48]
B
Today is a totally hits driven business.
- [20:51]
A
So you have kids, let's assume your kids were going to college and you're going to do what your parents did but in a different way. What is it you're going to tell them to go study? Not your computer science and engineering.
- [21:03]
B
So I mean look, I have a soon to be 11 year old boy, a 6 year old boy and a 5 year old girl. The two younger ones are too young. The 10 year old yesterday 11 year old almost said to me yesterday, randomly said boom, only seven years, six, seven, eight years away from college. He's very interested in aviation because he draws planes with like a lot of detail and so without pushing him into it, I want to guide him towards it.
- [21:34]
A
Do you think he should follow his passion? Like you know that age old adage that they tell you like follow your passion, not the money.
- [21:42]
B
I don't know, I mean like I followed my passion.
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A
You, I think you. I perform better when I care.
- [21:49]
B
One of the ways I think about it, if I can put my arms around a topic, I don't know if this is certainly not a scientific way of doing it, but if I can put my arms around a topic, I can focus on it and I can be a success on it. The example being at skift, we tried to expand beyond travel into the business of restaurants and wellness. Beyond a certain point I did not give a shit about the business of restaurants or wellness, and we fail at it. And the way I rationalize it, I just couldn't put my arms around those topics.
- [22:20]
A
This idea that there's riches in the niches of, like, hyper focusing is definitely something you've done a remarkable job at.
- [22:27]
B
Yeah. I think that going deep into a subject and becoming the most influential for. So I consider myself an instinctive entrepreneur versus data led entrepreneur. If you sort of broadly categorize, it's instinctive entrepreneurial, as in working on your instincts versus using data to make decisions somebody has to use inside the company. So my co founder does. He's led by data, which I'm glad he does. But I'm very instinctive. I think I have an instinctive sense of people's media consumption habits, particularly in the business world. I have an instinctive sense of where the story lies.
- [23:08]
A
I'm gonna go back to. The thing that strikes me is that you were always interested in influence.
- [23:13]
B
Yes.
- [23:14]
A
Not money. You never said money, but you were always interested in influence.
- [23:17]
B
Yeah. Money for me is. I'm gonna say, not important. I mean, clearly my first job, I didn't go into computers, so money was not an issue for me. It's like, if I don't have the money now, I'll figure out ways to get it later, like. Or if I lose money now.
- [23:32]
A
And I will say, you've done perfectly well for yourself, by the way.
- [23:35]
B
Yeah.
- [23:35]
A
So you cannot prioritize it. You can be focused on influence and still do. Okay.
- [23:40]
B
Yeah. And one of the other things that I guess Indians Eastern mentality teaches you is delayed gratification. Right. We're all living, saving for that day when we will be. We'll have enough. Right. This is what life in India was certainly when we were growing up in the 80s and 90s. And as an entrepreneur, that equity is the delayed gratification that at some point you will build a company that will sell and you'll be rich enough.
- [24:07]
A
And you've had that once so far.
- [24:08]
B
I had that once. And long story short, wasn't that great. But this time we'll be fine. Yes.
- [24:15]
A
Because Skift is doing nicely.
- [24:16]
B
Skift is doing well. Yeah. Yeah. If we don't screw it up.
- [24:19]
A
So why influence?
- [24:22]
B
Again, a question. I don't know why nobody has asked me before.
- [24:25]
A
Apparently I'm good at asking you questions nobody's asked you before.
- [24:27]
B
No. But it's an obvious question. Right. I think that's why people don't ask, because it's such an obvious question.
- [24:33]
A
But it's a deep question. Because it's the thing that drives you.
- [24:36]
B
I don't want people to like me because that's. Because influence could also mean liking.
- [24:40]
A
Right.
- [24:42]
B
But respect. I think that outsider looking in respect and understanding that as a journalist, if I have an opinion, I'm speaking from a position of knowledge. That's what I want the other side to. To feel.
- [25:00]
A
I'll try and be introspective, which is actually, I will say to you, hard for me because I compartmentalize and half the time don't remember the difficult things. But I think for me, as the outsider looking in, I wanted a seat at the table, you know, like, I wanted to be part of something that went somewhere and I was. I was motivated by impact.
- [25:21]
B
I've written about it. Like, as long as we're making small but permanent dents in the universe, we've done something.
- [25:27]
A
Yeah, right. Better than you found it.
- [25:30]
B
Yeah. It doesn't have to be a big dent as long as these are permanent dents, as in people that worked for me, that when I die, they will remember, say, oh, yeah, he did something for me. In my career, I've started thinking about legacy. I mean, surely emotional, mental, financial, et cetera. But I've also begin to think about physical legacy. And by physical, I mean what am I leaving them? That's in a world where everything is becoming digital and virtual. What is the physical thing I'm leaving them? So I've started asking them to come to my events. As a result, they can actually physically see their dad. I work from home. I can't call them to office. My office is my house. They're in there all the time. So they come to my events.
- [26:12]
A
But that's kind of an amazing thing to share. It's like bring your child to work day.
- [26:15]
B
Yeah, it is amazing. And then my elder son, you know, he's 11, so I want him to see what I do for a living. 2024, we just gift India forum in Delhi. First conference in India.
- [26:27]
A
That had to have been great.
- [26:28]
B
It was amazing. Like, it's a lot. It's a lifelong dream to do the conference. And then my mom came and it was very emotional for her. Very emotional. It was emotional for me, but it was emotional for her in a different level. My parents did not understand what I did since I left. You know, I went into blogging. Can you imagine trying to tell my mom and dad in India?
- [26:52]
A
I'm seeing her describing you to people at her home.
- [26:54]
B
Yeah. So she didn't know. When I brought her to the conference, it was Ramadan. And so she was fasting and my sister's like, there was a. It was about 500 people and there was a Rafat family table. She was supposed to be there for two hours and then she was crying the whole day because I was on stage multiple times and she wouldn't go because I wanted her to go because she's older and she's fasting.
- [27:21]
A
Oh, but that has to have been an incredible moment.
- [27:22]
B
It was an incredible moment. The US Ambassador to India was speaking there and I was intervening him. He also acknowledged her from stage, which was a huge deal for her. Oh my God. And by the way, that type of like family thing is only possible in our cultures. Back in India, like in us, everybody look at you. Weird. But in India, that was so great. She said, I didn't understand a word. Like I didn't understand what, what the subject matter was, but just that my son is on stage.
- [27:49]
A
You shared your influence.
- [27:51]
B
And also like she. All of these people have seen me, my sisters, my brother have seen me grow up, stammering, underconfident kid. And sure, they've seen me successful over a period of time, from far, but had not seen me in action. I'm very comfortable on stage, which now that I think about it, like my 17 year old self or 16 year old self to say that I'm, for me, stage has become so natural.
- [28:17]
A
Now what would you have said to your 17 year old self, knowing what.
- [28:21]
B
You know now, in the end it all works out.
- [28:24]
A
After a lot of mess.
- [28:26]
B
After a lot of mess. But if it's still a mess, that means it's not the end. Right? So there's an Indian saying or whatever. I don't know. I'm sure that every culture has a version of the saying which is that in the end it all works out. But if it's not worked out yet, it's not the end. The other thing I've learned, and I'm sure you've, I think you've said a version of this before, is like every setback, and I'll give you an example, a small example of like crucial people leaving in your company, right? Then you know it's a setback. Oh my God, it's a small company. And then one person leaves. Almost always you find somebody who will do a better job.
- [29:04]
A
Every setback can be an opportunity, is.
- [29:06]
B
An opportunity for a reset or something better comes off it a hundred percent. I know it sounds ridiculous. In the moment.
- [29:15]
A
No, in the moment it's overwhelming, quite honestly.
- [29:18]
B
Yeah.
- [29:18]
A
Like Covid, that was a huge setback, particularly in your business in travel.
- [29:22]
B
And, you know, because you were in travel. We came three weeks from running out of money, and somehow we crawled our way out of it without raising any external money. We did get the PPP loans and then the Silicon Valley bank crisis, which, if you remember, two years ago, two years ago, we had every penny of our money in Silicon Valley Bank. And so for three days, the worst three days of my professional life, certainty, because we lost all of that money. And I thought, we're done.
- [29:55]
A
That had to have been terrifying.
- [29:56]
B
That was terrifying. And as soon as it happened, I called my president. I've never cried in front of her. And I totally broke down. I said, this is over. Because for me, like, bankruptcy means you get pennies on the dollar after. But turns out bank bankruptcies are different than regular bankruptcies. But I didn't know that, you know.
- [30:17]
A
In that moment where you had this second, I mean, second that we can talk about existential moment. Right. You think this business that you've built, that you put your heart and soul into is gone, of no fault of your own, frankly. How did you, like, get up the next morning and go to work?
- [30:33]
B
There's a time to grieve, and then you turn off that brain, and then you focus on rescue plan or execution or action.
- [30:42]
A
How do you turn that off?
- [30:44]
B
How.
- [30:45]
A
How do you do that? I know how I do that.
- [30:47]
B
Tell me how you do it.
- [30:50]
A
I have a way of compartmentalizing, and I throw myself into the work. If I get anxious, what you'll find me is opening up the laptop.
- [30:57]
B
For me, it was work, but also playing off the energy of my immediate team. So similar with COVID what I said was, when we were trying to rescue the company three weeks away from shutting down, my co founder, Jason and I felt like we were in early days of skift, as in, we were going back and forth, say, oh, we turned this on. Can you check what this looks like? This is all happening virtually. If it wasn't existential, it would be exhilarating. But I think that also action over intent.
- [31:29]
A
Yeah. And I would say chaos is my sweet spot. Like, I run towards that and I like making sense out of it. Right.
- [31:38]
B
Yeah. And for me, I've learned over a period of time, like, I don't take notes. Like, I'm not a very organized person. I don't take notes. But in my brain, I compartmentalize. If it's important, I'll remember it. If it's not important, it's meant to fall off because Otherwise you go nuts.
- [31:53]
A
I don't remember things.
- [31:54]
B
Otherwise you go nuts. Right. There's too many things.
- [31:57]
A
Well, I also having worked in tech, I found they loved frameworks. They wanted to understand how I did things. I was like, just by instinct.
- [32:03]
B
Yes, yes, exactly. All of these are cliches, but the cliches for a reason. Like your gut instinct usually is. Right?
- [32:11]
A
Okay, we're almost done. You're almost out of your therapy session.
- [32:14]
B
This is more painful than I thought it was going to be.
- [32:17]
A
It's not supposed to be painful. This is what happens if you're like you and me compartmentalizing, like.
- [32:23]
B
Yeah, no, I thought it was going to be a business conversation, but dude.
- [32:26]
A
That is all the conversations everybody already has. I could listen to that already. Yeah, yeah. I never go where other people go. If they go right, I go left. So we're basically the same person. So I'm just going to ask you some rapid fire questions and we'll do the best we can and you'll be, you'll be good at this. What would you tell someone to do before they're 35?
- [32:45]
B
Travel as much as you can if you can afford it. 100.
- [32:48]
A
What career myth do you think is a waste of time?
- [32:50]
B
That if you jump from place to place you will get a higher salary? I think that's a, it's a myth.
- [32:54]
A
What would you say you would never do again?
- [32:56]
B
I said I would never start a media company again after I sold my first company and certainly that didn't work out. I have said now that I don't want to do another startup.
- [33:05]
A
What is one piece of advice you would give to somebody who's looking for a job?
- [33:09]
B
Don't be in a hurry. This book that came out 2017, 2018 called 100 Year Life was very influential for me in terms of thinking about longer time horizons. And the books talks about it in multi phase life as opposed to three phase life. Education, work, retirement. In a hundred year life, that's not humanly possible. If you retire 60, even 70, you have freaking 30, 40 years to live.
- [33:34]
A
I like that your advice is to not be in a hurry. And yet as an entrepreneur we always have urgency. How messy would you say your messiest part has been in a scale of 1 to 10?
- [33:43]
B
Oh my goodness, more than 10. I mean personal life whose is not messy?
- [33:49]
A
Everything is messy. When was the last time you cried?
- [33:52]
B
Probably earlier this year in January, February.
- [33:55]
A
What made you cry?
- [33:56]
B
This is so much therapy. Oh my goodness. I went through a little bit of a mental breakdown.
- [34:05]
A
Why? It Looks so perfect.
- [34:07]
B
I don't know.
- [34:08]
A
What are you saying to me?
- [34:09]
B
We adopted a baby, we moved into a new house. Tons of change in my life, so I took a break from work.
- [34:18]
A
That was very millennial of you.
- [34:20]
B
But it coincided with us adopting a baby. And what my team assumed that I was taking parental leave, was basically a mental break.
- [34:29]
A
We all need a minute these days.
- [34:30]
B
Again. As you grow older, you realize what the trigger points are, and if you're lucky, you're able to catch it earlier. I've gotten better at it, but not. Not fully.
- [34:42]
A
All the compartmentalizing. It does eventually catch up.
- [34:44]
B
Yeah, it does catch up.
- [34:46]
A
Okay, last question. What is a mess that led to success?
- [34:50]
B
My first company was a totally accidental mess. As in, I was blogging because nobody was giving me a job. I had no choice but to create my own job company over a period of time that obviously turned out to be a success. As in, I built into the company. I sold it. That's fine. One of the ways I've found to manifest success is that I visualize things a lot. As a kid, I used to daydream a lot. So my parents used to say, what are you thinking about? Why are you lost all the time? So my son, my elder son, does this a lot like he. He lives in his head. If I want something to be a success, I'm going to launch a new thing or launch a new conference or launch a new product or launch a new company. The more that I can visualize it in my head what that success would look like, the more I'm going to be pushed to make it a success. As in, I'll corral the resources in my brain around me and my team, etcetera, to be able to. To make that happen.
- [35:53]
A
This is not surprising that you also rely on instinct as well as data to make decisions.
- [35:58]
B
Yeah. So if your kid daydreams and is lost all the time, there's some value to it later down the line. Don't beat. Beat that part out of them.
- [36:08]
A
No, it's the creative part. I can't thank you enough for coming on, particularly given how different it was than what you were expecting. But, you know, I like to say if you go right, I go left, which, you know, basically brings us full circle.
- [36:20]
B
Yes. Yes.
- [36:21]
A
Thank you for making it to. To the end of this episode of the Messy Parts with Rafat Ali. Remember, subscribe, tell ten friends, drop a review, and more importantly, tune in every week because we drop new episodes weekly.