“You don't need to be doing something every single moment or every single day to feel accomplished. Actually, the best times of creativity come when you have nothing going on.” – Alex Simon
Alex Simon left a career in investment banking to start the travel app Elude, where he's the co-founder and CEO today. Elude is focused on helping people find and book incredible travel experiences. It's the only resource where you can simply input your max budget, your local airport, and how many days you'd like to be gone to find incredible destinations around the world that fit those parameters. So you can ask the question, where can I go next week for $1000?
In this episode, Alex shares why he's been fascinated with crystals, the three mentors he's learned the most from, and why one of them has continually pushed him to simplify Elude's design and user experience again and again and again. We discuss why he wishes he always trusted his gut instincts as much as he does today, and he shares his two favorite books, World Travel by Anthony Bourdain and The CEO Within by Matt Mochary. Finally, he talks about how and why he meditates at the end of each day.
Chapters
In this Playbook episode, we cover:
- 00:00:00 – Introduction
- 00:02:02 – Alex’s recent fascination with crystals
- 00:03:47 – Networking as a superpower
- 00:04:50 – Guidance from leaders at Lyft, Priceline, and Kelton Global
- 00:07:18 – Always trust your gut
- 00:09:11 – Building a startup is about marketing, tech, and everything business
- 00:10:39 – Alex’s favorite books to recommend
- 00:12:17 – Why daily meditation is a non-negotiable
- 00:17:13 – Jiu Jitsu as an outlet and creative source
- 00:18:34 – Why enjoying your daily work is so important
Books Mentioned
The following books came up in this conversation with Alex Simon
- World Travel: An Irreverent Guide by Anthony Bourdain
- The Great CEO Within: The Tactical Guide to Company Building by Matt Mochary, Alex MacCaw, and Misha Talavera
Selected Links
Transcript
Daniel Scrivner (00:06):
Hello, and welcome to another episode of our 20 Minute Playbook series, where each week we sit down with an elite performer from iconic founders to world renowned investors and bestselling authors to dive into the ideas, frameworks, and strategies that got them to the top of their field all in less than 20 minutes. I'm Daniel Scrivner. And on the show today, I'm joined by Alex Simon who left a career in investment banking to start the travel startup Elude, where he's the co-founder and CEO today. Elude is focused on helping people find and book incredible travel experiences that help them escape and see the world. It's the only place where you can simply input your max budget, your local airport, and how many days you'd like to be gone to find incredible destinations around the world that fit those parameters. So you can ask the question, where can I go next week for $1000?
Daniel Scrivner (00:53):
In this episode, Alex shares why he's been fascinated with crystals, the three mentors he's learned the most from and why one of them has continually pushed him to simplify Elude's design and user experience again and again, and again. Why he wishes he always trusted his gut instincts as much as he does today. He shares his two favorite books, which are World Travel by Anthony Bourdain and The CEO Within by Matt Mochary. And he talks about why he meditates at the end of each day and how he includes reflection on how the day went into that routine.
Daniel Scrivner (01:25):
You can find our episode guide and the full transcript of this conversation at outlieracademy.com/109. That's 109. And you can follow Alex Simon on Twitter @Al_elude. With that let's dive in. This is 10 questions in 20 minutes with Alex Simon of Elude. Alex Simon, welcome back. Thank you so much for joining me on 20 Minute Playbook. In the next 20 minutes, I'm going to ask you 10 questions. I'm going to try to draw out I think, get to know you a little bit better or get to know what makes you tick. Thank you so much for coming on. Let's get started.
Alex Simon (02:01):
Let's go.
Daniel Scrivner (02:02):
First question, I always like to ask if you can share a recent fascination, so just something, can be anything can be travel related, related to Elude or not. What can't you stop thinking about? What's been fascinating you recently?
Alex Simon (02:15):
To be honest, and this is going to sound a little bit like woo hoo, but like crystals, I've been very much dabbling into crystals. I have like small little Buddhas and things like that around, but I genuinely feel like the energy behind crystals is definitely the same type of thing with intentions and things like that. I've definitely been getting into crystals a lot more than I would like to admit.
Daniel Scrivner (02:38):
I mean, I love it. I have to also ask the noob question as someone who hasn't dabbled into crystals. What is maybe a surprising thing that you've learned or what would you, I guess, share for someone, just a high level tidbit about crystals?
Alex Simon (02:53):
Yeah. So depending on like what you're looking for in general, I think like there's different crystals for everything. So I'll give an example. I just recently had brain surgery about a month and a half ago and I'm on yeah, I'm on blood thinners. And again, this is a lot of information for the details, but there's actually specific crystals that could help with your blood flow. And so again, I mean, there's specific crystals for kind of all over the place, but definitely do your research, do a little bit more digging, but what's unique is that there's kind of a need for everything.
Daniel Scrivner (03:24):
So cool. It reminds me, super random, but I remember a couple of years ago reading a story about Robert Downey Jr who's also really into crystals and apparently he even has them sewn into his suits and he has them sewing into the Iron Man suit when he plays, which I thought was fascinating.
Alex Simon (03:40):
Yeah.
Daniel Scrivner (03:41):
So for anyone wants [inaudible 00:03:42].
Alex Simon (03:42):
I haven't gotten there yet. I haven't gotten there yet.
Daniel Scrivner (03:44):
You're not sewing them into your clothes. That's going to be the next,
Alex Simon (03:47):
No, not yet.
Daniel Scrivner (03:47):
Step. Or maybe that's a few more steps down the road. When you think about business and leadership, what do you think your superpowers are and how do those show up day to day?
Alex Simon (03:56):
Yeah. So I'm definitely great at networking. In general, I think being able to connect the right people at the right times, I think is a really big powerful tool. And then also too, I think for me specifically, I don't need to understand everything at kind of the detail oriented level, specifically as a CEO, but I like to look at it more macro. And so whether it's from the tech side, or the marketing, or the product, right, like I think as a founder and specifically a CEO, you need to have that high level overview at all times and think about the business kind of on a recurring basis, but not necessarily get too detail focused. Because I think a lot of founders get way too into the details and then they can't really scale or operate on a higher level. And so I definitely say that that is my strong suit is not understanding everything to the fullest degree, but understanding enough where I could ask the right questions and kind of push back to the right teams.
Daniel Scrivner (04:50):
Yeah. It's like you understand the topography and how it all relates and how it all interconnects and that's the area that you're focused on. It's super interesting. What mentors or figures shaped your approach to business and leadership and what mark did they leave on you? And this can be anybody, it can be an explicit mentor. It can just be someone you worked with.
Alex Simon (05:08):
There's three in particular that I've worked with closely. One is Sachin Agarwal who was over at Lift as well as he was another one of the founder teams over at Twitter. The second, which is Tom Bernthal and his partner Gareth. They've been incredibly helpful in terms of how to look at businesses in general and kind of operate as a whole. And then the third is Jeff Hoffman, who I mentioned earlier was one of the founding team over at Priceline. When it comes to the travel space, there's really nobody else like him. And I think again, as a new and up and coming travel brand, we need to be associated with the right individuals that kind of open the right doors. And that's been really valuable for us.
Daniel Scrivner (05:49):
Yeah. Is there any tidbit, quote, little lesson you can share that you've taken away from one of them?
Alex Simon (05:57):
I think this is a quote that I personally like abide by and it's by Napoleon Hill. It's basically whatever the mind can conceive and believe it can achieve. The one thing that I'll relate there to something that Sachin has actually been very like basically pressing us on is making certain that the design is simple because users look for simplicity. And I think like, whatever you do, whether it's in travel, whether it's in product, whatever the actual industry or sector is, it needs to be simple enough that you could describe it and that people are willing to go through the process and do it. And so he's been pushing us to get it very, very refined. And I personally love that because having that kind of back and forth and iterative process is always good.
Daniel Scrivner (06:47):
Yeah. I mean, that's a great voice to have around the table, and it's great to have somebody from the outside looking in that understands it with enough nuance, but also has an outsider's perspective to just say, Nope, still not simple enough. Just really quickly on that, my theory on simplicity is that it gets more valuable every day, because I think over time, our lives all feel more complicated, they feel more noisy. And so I guess one maybe belief I have is that simplicity has a compounding advantage, if you can get good at it too.
Alex Simon (07:18):
I love that. I love that.
Daniel Scrivner (07:18):
This is a little bit of a weird question, but I always like asking it and so if you want to think about it for a few seconds, feel free. But if you can go back to the beginning of your career, so you started as an investment banker and whisper words of wisdom, a quote, reminder in your ear that you would have benefit from over the course of your career, what would that have been? What advice would you give your younger self at the start of your career?
Alex Simon (07:41):
It probably sounds very general, but like, as you're saying that again, this is the second time now on the podcast that I'm getting goosebumps, but like, I wished that I told myself this, and it's trust your gut. A lot of people say that, but a lot of people don't actually trust their gut. And they'll go ask for a lot of opinions. And even me personally, like I was mentioning around the advisors and getting insights from all these other trusted sources.
Alex Simon (08:07):
At the end of the day, if you don't feel like what you're doing is enough for you, you need to make that change and nobody's going to do that for you. You have to do it for yourself. And so in those early days when we were starting and even down to like my early investment banking days, like I always felt like I should be doing something a bit more. And I wanted to have something in my hand and travel in those type of areas. And I wish I just trusted my gut a little bit more back then. Now, I'm learning to trust it over time in a much more quick format, but I wish I would've told myself just trust it from then.
Daniel Scrivner (08:43):
Yeah. Like develop that trust early on. Don't discount it.
Alex Simon (08:46):
Yeah.
Daniel Scrivner (08:47):
Listen when you feel something.
Alex Simon (08:49):
And even when everybody else is telling you your a little bit nuts, like again, early on in the investment banking days when I was making the leap into entrepreneurship, everybody, friends, family, loved ones, I mean, they were all telling me, why are you giving up a career to go and do this travel thing. And so like just owning that confidence and making that jump is what I wish I told myself.
Daniel Scrivner (09:11):
Yeah. I love that. If you had to distill down your philosophy of building a company into just a few words, how would you describe your approach? And I think what I'm trying to get at there is like philosophically, culturally, how do you think about what you're building at Elude and some of the principles behind that?
Alex Simon (09:29):
I'm much more of a tactical person. And so right when you say that question, my mind goes to like three words, which is marketing, tech, and then everything business. And basically like, that's how I live my life day in and day out. Like it's in those three buckets. Like tech, I don't quite understand. We have our CTO who helps manage that. Marketing again, I don't quite fully understand. I have our CMO and my co-founder Frankie.
Alex Simon (09:57):
And then business, everything else when it comes to accounting and things like that, like you have to kind of find these buckets that make the most sense for you as a founder, but I think operationally, having your hand in each one of them and understanding what the impact is and really like, you can't run a business without all three of those. You can try, but most likely it's going to fail if you don't have those kind of three legs. And that ironically, I've heard that from other founders, as well as like, there's this constant ebb and flow of maybe one week or one month, it's not going to be marketing. Right. And that's going to be two months from now, but focusing on the tech and kind of having these cycles is definitely how I've operated.
Daniel Scrivner (10:39):
Yeah. Well, and that's also an aspect of what's so challenging about being in the founder role and in the CEO role is you have to constantly be ebbing and flowing between very different things, which can be really uncomfortable to be able to do that. Is there a book, article, or paper that you love that you think more people should read?
Alex Simon (10:57):
Okay. So I have two. One is I actually always have this by me, is the Anthony Bourdain, World Traveler. And so again, I'm a huge, huge fan of Anthony Bourdain, strongly suggest. These are just top destinations that he's been to. And so as a fellow traveler, I always like to suggest it because even if it's like not business related, it's getting people to encourage, going and seeing the world. And then the second, more on the business front, it's called The CEO Within. And I always have that as a reference point as well. Everything from board meetings to marketing spend, I mean, they literally cover it all in terms of how you should start to approach it if you haven't done so already. And I always go back to that book, if I'm like being dealt with a scenario or a situation, even down to like employee conflicts or problems or whatever it is like, they really handle a really good job of having like a rule book basically.
Daniel Scrivner (11:55):
Yeah. No, I would totally agree. And I would second that book because it's not the end all be all. There's a lot of great books about business, but when you become a founder, when you become a CEO, nobody hands you an overview. And that book I think, is a wonderful overview. It just covers a lot. And you can go and zoom into kind of a particular area.
Alex Simon (12:14):
Yeah. It definitely creates a foundation. Yeah.
Daniel Scrivner (12:17):
Yes, yes, yes, yes. A foundation and in a lot of ways it's yeah, if you suddenly find yourself and you need to have that difficult conversation, how do I do that? Go back to the book. It's got at least a good breakdown of how to approach it. Switching tacts a little bit, what tiny habit or practice has had the biggest positive impact on your life?
Alex Simon (12:37):
Positive impact for me has been from a personal level, meditation. I do that every single night and that's definitely something that's like a non-negotiable for me. And then when it comes to business in general, actually, like I know that this is going to sound very minuscule, but start small. So like every single morning again, like making my bed, doing the dishwasher, doing laundry, things that are kind of like smaller tasks that you can kind of complete on a grander scale. That actually starts to make or break your routines from a much more like weekly and monthly basis. And so my strong suggestion is find those small little things that you can do on a daily basis. And that will really have a direct impact into how you actually operate on a day to day when it comes to business.
Alex Simon (13:24):
And so, and then the final thing, and this is like what I wish I told myself in some capacity of like routine is you don't need to be doing something every single moment or every single day to feel accomplished. Actually the best times of creativity come when you have nothing. Or when you have like three or four hours by yourself and just like walking around or doing whatever. It doesn't need to come with structured time. And I think I learned that the wrong way where I thought, especially as soon as I jumped into entrepreneurship, it was like, if I'm not doing something every single minute, if I'm not talking to an investor, or a product person, or the tech team, like nothing's going to get done. And you kind of have to trust that like that's actually not the case and the best forms of creativity come with those open times.
Daniel Scrivner (14:10):
Yeah. So well said. And totally agree on the practices. For me, I feel like, I try to work out every single morning and I do feel like on the days I can't do it, yeah, on the days I do it, I feel like I can do anything, on the days I don't I feel like sometimes I struggle. And so, yeah. It's like getting a win in early. I want to ask one other question on the meditation practice, just because it's interesting that you do it at the end of the day. Is that for you a way to decompress and kind of switch from work mode to being at home? Talk a little bit about like why end of day and what that gets you.
Alex Simon (14:42):
It's kind of more of less my point in time in the day to be able to understand what just happened. And so typically I find myself, it's typically like a guided meditation with just like music, not words. And a lot of the times it's like 15 to 20 minutes, but the first five minutes is me actually decompressing and kind of me asking myself the questions in my head of like, did I do well today? Did I do what I wanted to do? If not, what's still outstanding? And maybe I do that after the meditation. But it kind of is like this point in time for me to realize what has happened and really not do anything else.
Alex Simon (15:22):
And then the remaining of the meditation is much more of me to your point, like transitioning to a wind down, let me sit with my wife or let's have a cup of tea or something like that. Like where it's a little bit more of now I'm disconnecting from work. And I think, again, as founders, you're living, breathing. I mean, I haven't had a day off since the day I started Elude. Right. So like, but that's constant. And so like what keeps me grounded is those points in time to be able to say, okay, look for the next two hours or three hours, I'm not going to be doing anything work. Now on the days that I actually do need to jump back into work, okay I come back at it with a fresh set of eyes. But yeah, it's kind of just at that point in time.
Daniel Scrivner (16:03):
Yeah. Yeah. I love that it's like a looser practice and that a part of it is just reflection because I do find that that's really powerful. And if you don't build that in, I don't know, you miss out on something. And it's also something that I think just people, just everybody, I think criminally under prioritizes as if like thinking back and reflecting is invaluable.
Alex Simon (16:22):
What I think is actually most unique and again, hopefully other listeners can think about this, one day you may be feeling extremely anxious. Like I'll give an example. Like we closed our seed round back in November last year. That month was very heightened stress for me. I mean, we're talking about raising millions of dollars and like waiting for kind of the wires to hit and the people to get committed and all of that. But it's always a good point in time to now look back and be like, wow, okay. I was feeling anxious, but now I'm not. And like having those points of reflection and realize that over time, that's the ebb and flow of life and just kind of taking for what it is.
Daniel Scrivner (17:01):
Yeah. No, totally. So it's like a recognition of the moment in time you're in.
Alex Simon (17:05):
Yes.
Daniel Scrivner (17:05):
And also recognition of maybe what's just passed. It's like,
Alex Simon (17:07):
Yeah. What I'm not going through right now,
Daniel Scrivner (17:10):
Yeah, exactly.
Alex Simon (17:10):
Or vice versa. Yeah, yeah.
Daniel Scrivner (17:13):
Yeah. No closing a round is very stressful itself. I'm sure you're glad you've got that out of the way for now. Two last questions, and this one's totally out of left field. What is your favorite way to waste an hour? And what I mean by that is kind of, if you had that unstructured time where you could do anything, what do you do in that time that feeds you, that propels you, that kind of just fills you up?
Alex Simon (17:35):
So before the brain surgery, it would be jujitsu. That was incredible outlet for me to be able to really like, just not think about anything else, but the tactics at hand. I'd say now is much more about walks and that to me personally is a great way for me to just kind of zone out and like, again, I almost find almost all of my creativity comes when I'm actually on walks is like, it's this downtime that doesn't exist about work. And it's just kind of like walking up and down the streets here where I live. That's always a really good opportunity for me to just kind of check out. But yeah, I would definitely strongly urge anybody to consider jujitsu because that's, again like a very great mind fitness, but also regular, just fitness.
Daniel Scrivner (18:19):
Yeah. And I'm guessing at some point you'll be back to jujitsu. It's just a recovery period.
Alex Simon (18:23):
Yeah. Probably like another six months.
Daniel Scrivner (18:25):
Yeah. You don't want to be slammed on the mat anytime,
Alex Simon (18:27):
Yeah. Yeah. Probably not,
Daniel Scrivner (18:28):
Soon after brain surgery.
Alex Simon (18:28):
Probably not what the doctor ordered.
Daniel Scrivner (18:31):
No, I would think not.
Alex Simon (18:33):
Yeah.
Daniel Scrivner (18:34):
Last question. When you kind of think, we've talked a lot about this, so in some ways this is maybe an annoying question. I think it's interesting, we've talked about different advice, different lessons you've taken from things. When you kind of boil it all down, what is the most important lesson you've learned so far? And this can be in life, this can be in business, this can be in both. What is it?
Alex Simon (18:56):
Yeah. I love that. You have to enjoy what you love to do. Like, if you don't like what you're doing on a day to day basis, unfortunately, and I'm not going to be like, I'm not this grand master or guru, but it's going to come out and it's going to come out in other forms, whether that's you with children, or you with your work, or you with just downtime in general, you're probably not going to enjoy the things that you like if you don't really like what you do on a daily basis. And I think the quicker that you realize that or try to find, and this is the other thing too, like as a kid, we're always like, we're taught, like let's go and find 15 different things that you like to do and see which ones you resonate, right?
Alex Simon (19:39):
Oh, you don't like soccer, you go move to baseball and you don't like baseball, you go to football. Right. You have this kind of choice to go and find things that you enjoy to do. The second we enter into the workforce, a lot of that stuff dies. And unfortunately that's when over time, if you don't like what you're doing on a day to day basis, it can come out in a lot of other areas. And not to say, I hated my corporate world. Like again, I mentioned this before, I stumbled into entrepreneurship. I enjoyed my corporate world, but like this kind of intrigued me. And I think doing things that intrigue you like, those are always great ways to be a little bit more curious and like find what makes you tick. And again, for me, it's travel and I've kind of like scratched that itch if you will and it's definitely something that I've enjoyed.
Daniel Scrivner (20:26):
Yeah. No, that's so well said. I mean, I kind of think of life as ultimately a journey to become the best version of yourself. And I think to say that another way, if you don't find the thing that you're on fire to go and do and that you don't love doing, I don't think you can become the best version of yourself. It's kind of a prerequisite. Well, it's a perfect note to end on. Thank you so much for coming on again. This was so much fun. For people listening you can follow Alex @Al_elude on Twitter, and you can also find Elude, it's an amazing travel booking app, it's kind of search centric at elude.co and you can also download it on the app store. Thank you so much for the time. I appreciate it.
Alex Simon (21:04):
Yeah. Thank you so much.
Daniel Scrivner (21:07):
Thank you so much for listening to this episode. We hope you enjoyed it. You can find our episode guide and the full text transcript of this conversation at outlieracademy.com/109. That's 109. For more from Alex Simon, listen to episode 106, where he joins me on our founder's spotlight series to go deep on what he's building at Elude, which is a startup that's focused on travel search and discovery, including why travel is considered a startup graveyard and how Elude overcame those obstacles to build a big and completely new company in the space. How Alex and his team brought deep experience building Google search to build their own unique search experience for travel. We talked through all of the regulation in the travel space, why it exists and how it impacts companies. We discussed, why Elude wanted to become a merchant of record, owning the customer and transaction from end to end, rather than following the typical playbook of simply building a search UI, and then using affiliate links to pop visitors out to airline and hotel websites.
Daniel Scrivner (22:07):
And we discuss all of the lessons that Alex and his team has learned building Elude over the last few years and reaching more than 500,000 searches to date. You can also find the video version of this interview on YouTube at youtube.com/outlieracademy. On our channel, you'll find all of our full length interviews as well as our favorite short clips from every episode, including this one. So make sure to subscribe, to get notified whenever we share new videos. And if you haven't already, follow us at outlier academy on Twitter and LinkedIn, so you never miss a new episode. Thank you so much for listening. We'll see you right here next week on Outlier Academy.
On Outlier Academy, Daniel Scrivner explores the tactics, routines, and habits of world-class performers working at the edge—in business, investing, entertainment, and more. In each episode, he decodes what they've mastered and what they've learned along the way. Start learning from the world’s best today.
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