Sam Simmons on Disrupting Travel Planning, Leading Under Pressure, and Business Lessons from Professional Poker
In Brief: Sam Simmons, CEO and Co-Founder of MintPass (mintpass.com), joins host Dan Freehling. Sam and Dan discuss MintPass, a web3 travel app that rewards users for sharing and discovering trusted travel recommendations. Sam explains the use case of web3 and NFTs in creating incentive alignment in various industries, using travel as a prime example. Sam also shares insights from his experience as President of PokerGo, the world’s leading poker content network, where he led the company’s pivot from 24-7 linear TV network to a subscription video on-demand service. Sam and Dan also explore leadership lessons from poker and World of Warcraft, the importance of embracing chaos, and the potential for gamification in business.
Recommended Reading: “Musashi” by Eiji Yoshikawa, “Actionable Gamification” by Yu-Kai Chou, “Atomic Habits” by James Clear.
Transcript
Dan Freehling (00:02):
Welcome to Forward-Looking Leadership, a podcast for visionary leaders building future ready organizations. I'm your host, Dan Freehling. I'm the founder of the coaching and consulting practice Contempus Leadership, developing the leaders and teams you want in charge through cutting-edge approaches and common-sense solutions. I'm honored to be joined today by Sam Simmons. Sam is the CEO and Co-Founder of MintPass, a Web3 travel app for sharing, discovering and rewarding, trusted word of mouth travel recommendations powered by NFT digital souvenir collecting and partnered with the likes of Expedia, Skyscanner, and Coinbase. Sam has positioned MintPass at the forefront of mainstream web3 adoption through a compelling travel use case. Previously, Sam was president of PokerGo, the world's leading poker content network where he led the company’s pivot from 24-7 linear TV network to a subscription video on-demand service and won multiple industry awards for live events and original programming production. Listeners, you're in for leadership insights on technology, risk-taking, and so much more from this conversation. Thanks for joining me on Forward-Looking Leadership, Sam!
Sam Simmons (01:04):
Hey Dan, thank you so much for having me and I'll say that is a much better introduction than I could have introduced myself, so thank you so much for that. Glad to be here.
Dan Freehling (01:14):
Sometimes it takes that outside perspective of what you're doing, doesn't it? So first, could you please share with listeners a bit about MintPass and your journey to get there?
Sam Simmons (01:24):
Yeah, sure. It is a long windy road and you alluded to some of it in that introduction there. MintPass is a web3 travel rewards network. So the whole premise is we discover our best travel booking decisions based upon often the word of mouth recommendations from other travelers. We know and trust, that's friends, family, and people we might be familiar with in our network who we respect as travelers and we seek out their advice and recommendations when planning our own trips. And we believe that that information, despite how valuable it's is, quite hard to access. So we basically want to create this cool web3 powered application interface where you use your mobile phone to authenticate your travel experiences, to create experience lists which can be shared with friends. And then when those friends book based upon your lists, when you share them as recommendations, you earn rewards from it.
(02:16):
And there's a lot of other implications to that around social graphs and giving reputational ratings to one's travel recommendations based upon how many cool things they've done in travel. Because as you'd expect, the more someone's traveled likely the better their recommendations are. But all that being said, we'll get into some of the specifics of that as we go along. We're just trying to create this cool tech powered solution for people to share, discover, and earn rewards from their great travel recommendations. And what led me to that is not at all travel, not at all tech, not at all. web3, very different world as you mentioned there. I previously worked in gaming media, so worked with a company PokerGo that you referenced doing streaming production distribution of live tournaments and events like the World Series of Poker and others. And over the course of several years and spending a lot of time there working on a lot of different live events, original programming productions, I really developed an aptitude for super serving passion audiences.
(03:20):
And I mentioned not being from the web3 space, that's what got me into web3 initially is this NFT industry in particular, obviously a very silly space, but there is a lot that the technology has to offer in bringing together human capital over shared interest and shared passions over a certain thing and being able to form digital communities and share in that passion together. So that's really what led to MintPass and eventuality after that long winding road, I wanted to create some cool NFT powered experience for travelers at the time and out of Covid when people weren't able to travel, there was a longing to better connect and reconnect with one's past travel memories. And so we asked ourselves, why can't we do that digitally and do that with digital souvenirs? And that's what led to the creation of MintPass. So I guess I went in the reverse order there. I started off with what we're doing now and got there with what I was doing before, but hopefully out of the box. That all makes sense.
Dan Freehling (04:17):
Thanks so much for sharing that. It's such a cool journey and we'll definitely be poking at different parts of that and then your insights and learning from them as we go through our conversation today. For sure. Starting off, you've alluded to some of it on web3 and NFTs in particular and how you see their use cases. And just as someone who's not really fully in this space, they have such a kind of a mixed reputation and there's a lot of silly use cases as you've also mentioned here. How do you think about these differently than many other people do?
Sam Simmons (04:51):
Yeah. Well first I'm going to answer that question with how I think of them. In many cases, the same. I'm self-aware enough to know that there's people that go out of the world and pitch their NFT or pitch their crypto and oftentimes it's with a certain negative connotation in mind. And I always just boil that down to a singular word which is speculation. And much of generally industry, much of the, for better or worse, the incentives are tied to financial outcomes tied to moneymaking and in many cases getting other people to buy what you're selling such that the thing that you're selling goes up in price as there's more demand for it. And that's not what this is. I want to be very clear about that off the rip, where we believe that web3 is best used for as I like to surmise it for incentive alignment.
(05:41):
And that is looking at various, no matter what industry, it's rather vertical agnostic. And you could find use cases across all industries looking at various ecosystems of value and rewarding those who contribute to that ecosystem being sustained. And that all sounds very vague, but let me zero in on what we mean in travel and how we're trying to help that admit past. Going back to what I mentioned earlier, looking at how we get our most important source of travel, booking decisions being word of mouth, recommendations from friends, family, people we trust. There's a stat that we love that 84% of travelers made their last destination decision based upon a word of mouth recommendation. And if you think about how much value is being driven to travel operators off of the recommendation from loved ones, again, friends and family and get those friends and family get nothing in return so to speak, for driving that booking.
(06:40):
And what I'm not saying either is we're not trying to create an affiliate mechanism for travel booking where everyone has links and they're creating lists and trying to get you to buy this hotel or this tour or this or that because it undermines the premise of all of this, which is the intrinsic value of sharing recommendations. But what we're trying to do is utilize reputation, utilize rewards to aid in the discovery of these recommendations because we know that the space is, the recommendation space let's say is very fragmented, very offline, very peer to peer in nature. It necessitates friends and family. Having collected notes in Apple Notes is what my wife uses. In fact, spreadsheets, camera rolls, other sorts of offline means for documenting what one does when one travels. And so we want to bring that information online and for our purposes bring that on chain and then allow for this open ecosystem dynamic of discovering travelers like you travelers you can trust based upon their proven experience and rewarding those travelers for their contribution to this global network of recommendations based upon the bookings that come off the back of the recommendations that they share.
(07:50):
So it's this cool and this again this not to continue to sell what we're doing, but there's this cool means of incentive alignment where everyone wins. And that's where I think the best part of web3 is and where the best use case lies is when what we segment them as is travel planners. So those that are looking to make their booking decisions, travel taste makers, those that have had great experiences and long to share those with others, and then travel operators, so those who can drive incremental revenue off of those discovering these recommendations and being able to book at the point of recommendation as opposed to needing to take to Google and other sources to seek out other means for booking these experiences, accommodations and so on. So that's why I love web3 thinking about incentive alignment and how can all parts of the value chain benefit from the incentives that the ecosystem can offer. And that's what we're doing with travel and that's what web3 can offer a number of different industries across different verticals.
Dan Freehling (08:53):
It's so cool to hear. So it sounds like a lot of this is on this incentive alignment leading toward basically can you get people to all be working toward a mutually beneficial way of interacting on this, in this case, in the travel space of pulling people away from all of their different kind of discrete ways of making recommendations and the sort of hidden negative incentives that might be there for leaving a review, for example, at a particular place or having an affiliate deal set up with a particular place and bringing them all toward this common goal of helping the rest of the community travel in a way that's trusted and better.
Sam Simmons (09:29):
Absolutely. And you mentioned reviews there. Another stat that we like to cite is that, what's the stat? There's a 20 times increase in AI generated fake reviews since 2020. There's a lot of twenties in that sentence, but the point is, especially in the post chat GPT era, let's call it, there has never been a less authentic source of information than online reviews. And so while we don't necessarily, I think we can be honest with ourselves, the total number is close to 10% of reviews have proven to be fake. There's actually been in the news recently some legislation out there that bans a lot of the mechanisms that go towards the aggregation of fake reviews, which is a good sign. But what's always been the case is that we trust recommendations from friends more than online reviews. Even if it's 10,000 people rating something four and a half stars on TripAdvisor against one friend who says, Hey, I took this trip to Florence last year, you got to check out this restaurant.
(10:30):
We found time and time again that the recommendation from that friend that you know and trust is going to be more valuable than the 10,000 strangers online. The problem is, again, that information is very hard to access. So what we ultimately want to do is create this trust layer of travel recommendations where think about planning a trip and being able to go to this interface and say, Hey, who of my friends has been to Florence? When did they go? How many times have they been there? And then what recommendations do they have from their time spent while there? And that doesn't exist today. It's again, very, it requires you to reach out to those friends. You're kind of asking around, you're hearkening back to, Hey, I think this person posted something from Florence six months ago, maybe I'll check in with them and see if they have a recommendations list.
(11:10):
And all that being said, you're just hoping they even have that list because oftentimes if they haven't taken the time to accumulate that information, they just won't. So that's where the network sharing the ecosystem contribution comes into play because historically there's really been no incentive to store that information as you travel, but we want to be that layer where we make it easy, we make it fun, and we make it rewarding to store that information for the purposes of others' travel inspiration. And again, when you inspire those other experiences amongst the network, you're rewarded for that contribution.
Dan Freehling (11:42):
Such an important use case here and it just obviously helpful to people traveling. It's funny you picked Florence. We haven't talked about this yet, but we're actually there last summer, my wife and I on a trip. And it was very much the same kind of a situation where she had done a study abroad there when she was in college and it was kind of like remembering these different places, reaching out to friends to remember 'em, getting back in touch with other people who've been more recently we're passing on our recommendations and something like this sounds really, really just useful to be able to look at trusted reviews and suggestions and recommendations and all of that kind of stuff from people. And then to be able to be part of this community and be engaged in it.
Sam Simmons (12:23):
I love that. I tend to use Florence as a personal favorite. My wife and I did our honeymoon there now two years ago, so it's got a special place in our heart. And I'm sure across both of our trips we had some intersection of activities as it was then. I know for us we did the Tuscany wine tasting thing and all of that. And similarly it's these trips that come to mind as the times that I needed what we're creating, the times where I was hoofing it, putting up the Instagram story of hey, heading to Florence, who's got recommendations or asking around to friends or looking at all these different information sources online. But what I find time and time again is that what we don't need is more information. What do need is better information and that's information from people that we know and trust and we want to be the infrastructure layer for that.
Dan Freehling (13:13):
It's a small world. Ours was our delayed honeymoon, we called it, and we did a brunello wine tour, which was awesome. Turning to this PokerGo experience with the pivot from linear TV to streaming, that's really fascinating to me. Could you share a bit more about that for listeners?
Sam Simmons (13:28):
Yeah, absolutely. So to give, I mentioned earlier I was formerly worked at that company PokerGo when my tenure wrapped up. I was president, which I had been in that role for a couple years and it was a interesting road over the several years of being there to get to that position, and a lot happened during that time. But essentially I joined the company in, I think it was 2014 originally and basically an entry level role. And at the time we actually, the company was entirely different name. It was called Poker Central. And we had set out to be a 24-7 linear TV channel for poker content, much like you would think about the golf channel, but for poker. And so a TV network for those that may not know the industry, you make money off of your network from the ads that you sell via commercials and the commercials only have value if you're able to prove that people are watching those commercials.
(14:23):
This seems obvious, but it's to set up the difficulty of this model. However, there is a limited amount of distribution channels that you can access to prove that viewership. And when I say prove, I mean the form of TV ratings. And so you look to the likes of DirecTV as it once was, I think there's Spectrum now, but Time Warner Cable, all of the major cable and satellite operators to gain carriage on their networks or on their channels, their airwaves, to then sell those eyeballs that they bring in to advertisers to then sell commercials to then have your network make money. However, that's not an easy thing to do. And I quickly came to find this that those conglomerates have a lot of power in the industry and to be frank, a lot of times it's a bit of a pay to play type scheme where you have to have the carriage to grow the audience to sell the ads, and they realize that.
(15:26):
And so they leverage that to basically require you to pay upfront to access those audiences. And so it becomes a very upfront cash intensive business because you're paying for the bandwidth, you're paying for the content, you're paying for the distribution and all of these things, and it takes a lot of upfront investment. So we had tried to do things more organic, we weren't doing any pay to play type stuff. So it was an uphill battle and there was a lot of just selling and selling and selling and trying to get this foothold in the industry to give us an audience substantial enough to effectively sell ads against it all the while. So this is around this time, this is 20 14, 20 15 evening back to sort of that era of content, which is approaching 10 years ago now. There was Netflix, there was Hulu, and that was about it.
(16:14):
Streaming was a thing, but it wasn't certainly as prevalent as it is today when you consider what's in the market now between Apple TV plus and ESPN Plus and Paramount, Peacock, all of the others that many listening might know of at this point. So there was this dichotomy really of our strategy swimming upstream to get carry on the cable and satellite players while everyone already on cable and satellite was in a way going downstream, no pun intended, launching their own streaming networks. And so myself being young in my career and someone who had never bought cable or satellite basically asked, well, hey, why are we doing this and why wouldn't we bring the content to our viewers where they are, which is already streaming as opposed to kicking and screaming our way into cable and satellite. And so for all intents and purposes, we tested both, and I won't go into the details of the test, but let's just say we took an event, we put it on TV and we put it on streaming.
(17:21):
And streaming did very well. In particular, we streamed it on Twitch as sort of a very low effort, high upside type ab test of sorts. And at the time we broke the record for a live poker event on Twitch. And so basically overnight decided, hey, there's something to the streaming thing. And we pivoted to go fully into that distribution model. We gave up the linear TV side, went full SVO streaming, and that became what Poker Go is today. And so that kind of kicked off my career on that side of things and I had the luxury of learning very quickly a new industry for me. It's not like I majored in media or did anything TV prior to working there, but it kind of just came instinctually from this is the content I like to consume and this is how I like to consume it, and now let's create an offering for that.
(18:08):
And there was a lot of learnings along the way. I became the VP of content right around the time we made that pivot, and then that became the president role at a future point. And I ended up leaving right around when Covid hit for a variety of reasons. But it was a blessed opportunity for me of being maybe right place, right time and having it be very formative to my career to date, as I mentioned earlier, in regards to the direction that took me in with the media, digital communities, gamification and all of these things combined.
Dan Freehling (18:40):
What a cool experience. So with that PokerGo experience and with MintPass more recently, how would you say you approach when you're going into a new field in business where you don't really know the field, know the industry, how do you approach deciding on a course of action, analyzing the industry, all of that kind of stuff?
Sam Simmons (19:02):
So maybe to a fault, my co-founder at Mint Pass name's Aaron, I always introduce him by saying way smarter than me, but he actually gets on me for saying that because I say it too much. But the point is that it speaks to my mentality, which is surround yourself with people smarter than yourself and always be willing to know what you don't know. And so I am obsessed with finding the people who know what they're doing, and even if they don't necessarily know what they're doing all the time, they have a relentless pursuit towards figuring it out. And I think it's a healthy mentality for anyone, but especially those entering a new industry is never think more than certainly the incumbents, but then the next guy or girl period. And frankly, I think having that mentality gives you an advantage over incumbents. And I found this now in a way doing this twice when it was earlier in my career going into television.
(20:06):
And that was the spirit of what happened was I worked with some very, very talented, very experienced media executives at the time who for by the strategy and just by asking like, Hey, wait a minute, is this the way of doing things? This doesn't make sense to me. The answer was always yes, this is how we do things, this is how we've always done things, this is how media works. And you kind of take a step back and realize, wait a minute, that's probably not the optimal way of doing things. And so that's ultimately what led to that big pivot. And so as I now enter this new space of travel, which is about as legacy as legacy industries get from just an old school mentality standpoint, relationship driven, this has always been way of doing things. I've actually, well, it gave me a lot of insecurity early in my career to say, I have no idea what I'm doing. I actually use that to my advantage now, and I'll proudly say I have no idea what I'm doing because in a way I am unshackled by the precedent of an industry, especially one that's old school like travel, where the only perspective we have is a fresh perspective. And I think with that comes a position of strength in figuring things out and finding your way within a space like this.
Dan Freehling (21:19):
So both respecting people who have been there and know what they're doing in it, and that first principal's thinking of being willing to ask, why do we do this? Rethinking the way things have always been done, and that combination gives you a real advantage.
Sam Simmons (21:33):
Yeah, absolutely. I want to underline the point you mentioned because I kind of glossed over it, but not turning away from, I keep using the phrase, but old school expertise. I think there's a way to combine and pull advantages from both. And so we have at admin pass an advisory board, a very smart, very talented individuals from the likes of United Airlines, from Via or TripAdvisor, from Expedia, from Caesars, Virgin Voyages, all of these legacy in varying ways, travel companies, and they're indispensable to us just for us navigating this industry. We need that on our side and we need what their brains have in them in terms of that industry expertise, but we take that with our fresh perspective in mind, and I think that's what ultimately gives us strength.
Dan Freehling (22:28):
Do you personally play poker or were you just involved on the business side?
Sam Simmons (22:32):
I used to play more, I still play a little bit actually as of this recording this past Saturday we did a big crypto poker tournament at our studio, the PokerGo Studio here in Las Vegas. And so it was my first foray back to poker in quite some time and actually the stream’s on YouTube for anyone that wants to look up my name and Rare Evo was the name of the conference. So Rare Evo with my name and you'll probably find it. But yeah, I still very much like to play and I enjoy a lot of the facets that poker offers as a game and how it can be applied to business relationships and life in general.
Dan Freehling (23:08):
On that note, what kind of business leadership lessons do you take away from poker?
Sam Simmons (23:14):
There's so many, and I'll try to just sprinkle them into the rest of this conversation because we'd be here for the next hour if I were to just itemize them one by one. But I think if I were to boil it down to a singular phrase, even more so a singular word would just be risk management. And poker is inherently a risky game, but it's all built on calculated risk. And I think that's where a lot of people wrong is subjective, but I think maybe some people go wrong in life by not taking enough risks. But I also think some people go wrong in life by taking too many risks and seeing the bad outcomes of what can be on both ends, whether it's the overly risky or overly conservative line. And so that's where poker at any given time comes into play. Where as I think about it, it's about decision making at a moment in time with imperfect information.
(24:09):
And that is the essence of everything that poker is. You have two cards in the game of Texas, hold them, there's five more cards to come. Do you think that as some function of the bet that you make and the cards that come out that you can win the hand that you're about to play, and the question becomes, do you continue to play or do you fold that hand? And that is no different than life at any given time, there's perhaps a opportunity to proceed or to fold if you will, and you don't know what's going to happen with either of those things. Decisions could work out for the better or decisions could work out for the worse, but you use that imperfect information to make the best decision at hand at any given time, whether it is risk on or risk off. And I'd say second to that and somewhat adjacent to that, I would throw in a need to not be results oriented and almost an acceptance of back to the phrase imperfect information where at any given time you make the best decision you can based upon the information that you have and that decision won't always be right, but having a willingness to not commiserate over those decisions and understand that you made the best choice that you possibly could given expected values and other factors of unknowns.
(25:24):
And there's really no point in going back and questioning certain decisions because the outcome at the time was unpredictable. So, and retrospective in nature where forward-looking, it's allowed for just better decision making in general, but also retrospectively having comfort in past decisions, just knowing and understanding that you're never going to have perfect information, so there's no use in commiserating over not knowing what you didn't know at the time.
Dan Freehling (25:50):
Yeah, the second one is really counter-cultural. I think for a lot of people I've read and listened to a lot of books, interviews with people who've applied the poker lessons to life and this idea of so much of the time we say, okay, that worked out well for that person. They must be a genius or That didn't work out. They must be stupid. And it's like, no, what was their information at the time? What was their decision making process? And that being much more important than just looking at the results of that one hand.
Sam Simmons (26:21):
Yeah. Another analogy that I love to delve further down the gambling road, I forget what book it was and I hate that I can't properly credit it, but there's this interesting phenomenon in say roulette where it's natural human instinct. You very calmly put your bets out. You may have your numbers in mind, in your head of where you want to place your chips in the middle, and then you get really nervous when the wheel is spinning and that ball is bouncing around because you want your number to hit. But in fact, it's actually when you're placing your bets where the nerves should take hold because that's the only time where your actions can have impact on the outcomes. Once that ball is spinning, the outcome is pre-ordained, your bets have been placed, the ball is in motion, there's nothing else you can actively do to change what's about to happen.
(27:12):
So what is the point of being concerned or worried about those outcomes? And so again, it's maybe a silly analogy to use for when you think about it in the gambling context, but if you think about business and leadership and decision making at large, just how we tend to worry about things in real time as they're playing out perhaps after a decision has been made is not aligned with what actually should be the case, which is deep thought and attention to making the actual decision itself, which includes that risk analysis that I referenced earlier, expected value and all of those things. So it's cool how, again, it seems obvious, but you start to apply it and it's like, wait, this is actually not that intuitive for most people. And that's, again, I say this from a place from not always doing it, this is stuff I remind myself to, so it's not like I can sit here and preach about if everyone would be happy if you just did this because it's a lot easier said than done. But again, practicing this in a gameplay setting in poker has been instrumental to being able to deploy these strategies in the battlefield, so to speak, of business.
Dan Freehling (28:19):
Yeah, thanks for sharing that. It's so interesting to think about where your stress should be, and it should be on the decision making rather than hoping it works out once you've made, it's just misplaced for a lot of people and leaders. On that same note, you've led during a lot of high pressure situations, I imagine with live events and all of that kind of an environment. And then launching your new business here, what advice would you have for leading in high pressure situations?
Sam Simmons (28:50):
Yeah, so when someone figures it out, let me know. It's easier said than done. Sometimes I do it better than others. I think I've been, at the time it was miserable, but in hindsight, it was privileged that I was thrust into a lot of uncertain situations early in my career. In that world of live production, I think especially when you consider the game of poker, I'm just going to rattle off a few examples of just WTF type moments in a management role. In some of our broadcasts, we'd obviously we'd highlight big personalities at the poker table, but as by definition, poker is a game where you have to rely on people to come into a room and put a hundred thousand plus dollars on the table to gamble with other people. And we would spend as a content company, much like a big price fight, we would spend days, if not weeks, promoting these big bouts of gameplay between high level and very famous poker players, but there's really no obligation for 'em to show up.
(29:54):
And for that matter, we had times where we had hitched a marketing wagon, a whole campaign to a certain player, and then the morning of they just decide, eh, I'm not going to go, or I don't want to fly to Vegas, or I found a better game in Macau, so I'm going to stay put and not come play. And so we're kind of left holding the bag promotionally of like, well, heck, we've just sold a bunch of subscriptions to watch this specific person play poker and they're not now going to come in and play. So it becomes a bit of a last minute scramble drill. It's like, how do we fill this line up? How do we make it comparable? How do we make good on those who have come in to watch this specific event? So you kind of had some chaos like that.
(30:33):
We did a lot of live productions with PN for the World Series of Poker. One year we had an earthquake, which earthquakes never hit Vegas, but it was the one in the past 10 years that actually was a sizable earthquake. The rooms were shaking. You have poker players with towers of chips in front of them, and you can imagine with the shaking and the hustle and bustle of people trying to get out of the room, all the chips go flying and the production shuts down and it's like, well, we have to give ESPN content. They had banked on that, so you can't just stop producing. So having to figure stuff like that out on the fly, which some of it being some of it being active God, some of it being perhaps active individuals who treat themselves like they're gods, there was a lot of uncertainty in a number of instances.
(31:22):
And I think really what my learnings were, and they continued to be is just embrace the chaos, find peace in it, understand that chaos will happen and know what's in your control versus out of your control. Be solution oriented, worry less about the problem itself, more about the resolution to that problem, which again, seems like all these platitudes, but when you're in the moment and you feel your heart rate increasing and you're just kind of in, what the heck are we going to do about this crap show that's unfolding? It's easy to just get caught up in the problem itself and start spiraling. And so it's again, easier have been done. I've had many years of problems with it, but just trying to focus on how do we resolve this as opposed to why is this happening? And then obviously it's then translated into the startup world really just keeping focus on what you can control and worrying less about the possibilities of what could go wrong around you or could continue to go wrong in some instances. But just putting laser focus on what can I control, and B, how can I control it to the best of my ability? And understand that anything outside of that ultimately boils down to not really mattering
Dan Freehling (32:43):
Such great points and great advice. And you're right, easier said than done in a lot of these, but it's a great reminder for people to follow these. And I think we've all seen or had leaders, managers, bosses who have not followed that in a lot of settings and during the middle of a crisis situation are trying to cast blame and it's just completely counterproductive to solving the issue. And you can figure out the retrospective later and what happens and how do you go upstream and fix that, but in the moment, so your whole goal is providing a solution, especially during a live event or something like that.
Sam Simmons (33:17):
And there's sometimes too, to use that negative example again, there's just sometimes where there's nowhere to point that finger. The example of the earthquake, this problem is just the problem. It's just a reality that we have to face. It's somewhat easier when you could point fingers because you can deflect and it's easier because it makes you feel better. Whereas where blame becomes an outlet and becomes almost cathartic, where when the problem can't be controlled or can't be attributed to an outside resource or outside source, there really isn't anything to do about it except for resolve it. So it's a different kind of issue. And certainly I find it easier to just treat all problems like that, whether it be, let's say user error or influenced by a member of the team or outside the team, whatever the case may be, as tempting as it can be to assign that blame and then take action on the blame itself and almost try to inflict punishment on the source of the pain point. What's much more productive is treating it like the act of God where it's like, okay, this is just the problem. Is the problem outside of us all, let's resolve the problem as opposed to trying to, I guess take it out on the source for lack of a better way of phrasing it.
Dan Freehling (34:40):
What a great reframe for that. And I think there's so much on, I talk about optics versus actually solving things a lot of the time. And I think this is such an example of that, of are you looking for what's going to make you look good? What's going to make you feel better in the moment or what's actually going to solve the problem and do what needs to be done for the team?
Sam Simmons (34:58):
Yeah, absolutely.
Dan Freehling (35:00):
So you did your undergrad in business, remind me, was it an accounting undergrad or was it a different kind of business degree?
Sam Simmons (35:07):
Technically speaking, it was a business with accounting minor, but I was full bore down the accounting track regardless of the full state of the degree.
Dan Freehling (35:17):
Gotcha. So with all that you've learned as an executive, as a founder, what changes would you make to business education based on your experience?
Sam Simmons (35:27):
That's a great question. I think for me it would be less learning, more doing, and I will take some personal blame as we talk about not assigning blame. I'll take some blame for my own personal life of maybe not doing this well enough and taking advantage of the resources that my collegiate experience had provided to me of actually taking my skillsets into the real world, whether it be through internships, whether it be through school, credit programs, study abroad, stuff like that. And I say this whether it be to students or entrepreneurs, perspective, founders, whatever the case may be, nothing has been as instrumental to my own learning journey then just going out there and doing it. And I think that's what tends to paralyze anyone in the number of facets of life, but certainly businesses, the uncertainty of feeling like you have to have all the answers before you get started.
(36:26):
And I've been in this trap very recently. I frankly waited too long to start passes a business after having the idea in 2021, I really didn't start moving in a concerted way on it until early 2023. So I was in that spot of like, okay, now I have to learn the ins and outs of the travel industry. I have to read all of the leadership books, all the business books, I have to read all of the YC entrepreneur and founder content to learn how to do this the right way. And then you just wake up one day a year and a half later and find out you actually feel like you know less because as you learn more, you realize how much you dunno, which creates this weird sort of double-edged sword where you almost convince yourself out of it over time. And so basically hit a point of stop everything.
(37:14):
I'm just going to go do it. And I think that's where, back to the college side of it, I think that's what I would endorse for any business learning journey of get out of the classroom, pursue, pursue what it looks like in practice. And obviously there will be classroom application to be had, but I wish it was more weighted on the collegiate level. It was less like, let's sit for 80% of the time in a classroom and then 20% of you choose to do so go get internship. I think the optimal business school experience is about half and half where even if you don't exactly know what you're doing, you're just kind of put into the world and counted on to figure it out along the way. Because nine times out of 10, from my own experience as well, you end up just figuring it out as you go.
Dan Freehling (38:00):
I totally agree with that. And I think there's this perfectionism that comes into play with a lot of people when they're thinking about, do I take on that next level of role where I'm going to be at a leadership or executive level and in charge of things or do I found this company? And it's something where you can't really be a theoretical leader sitting back and having this perfect preconceived notion of what it's going to look like in the real world and then making that happen. It's just not how it works. And I think it's kind of great that that's not how it works. It's much more fun the other way too, but you're so right. You have to just get into it and learn along the way and you can't sit back and wait to have everything perfectly lined up before you go in.
Sam Simmons (38:41):
Yeah, no, that's exactly right. And it's a whole different ballgame once you're out in the real world of, and there's things I couldn't even begin to fully digest on air the crises or issues that we had to deal with or I had to deal with during my time at PokerGo and even today, and none of these things couldn't be found in a business book. It's just the BS that life throws at you and the soft skills and propensity to find a way to handle it and to find a way to field these things as opposed to needing to figure it out scholastically or academically with A equals B type solutions. That's just not how life works. And I think that we talked back to incentives. I think the incentives of traditional education are incongruent with the incentives of the real world where it's not about answering these problems correct to get a positive result. It's about fielding these unknowns in real time and trying to harness them into a positive result when there is no clear right answer at any point in time.
Dan Freehling (39:50):
So right, theoretically the professor has the answer ahead of time and you're just trying to get as close to that as possible. And it's something where it's when nobody knows what the answer is because there is no exact right answer. It's such a different way of looking at it. And I think you're also so right on developing the soft skills of being ready to adapt and change and lead and all the kind of personal foundation of this too, of being prepared to be a leader and being in a leadership role or where the real value is, and not so much on the kind of preconceived, overly simplistic solutions or overly complicated solutions in some cases too, where it's like that's not really what's needed here. It's much more of how are you showing up to this and how are you problem solving right
Sam Simmons (40:38):
Through it. Absolutely couldn't agree more.
Dan Freehling (40:40):
How do you think about gamification and what do you see as its applicability to other businesses?
Sam Simmons (40:47):
Yeah, I think I'm a big believer in gamification and business and life and everything in between. I grew up playing a lot of World of Warcraft, like a gross amount of World of Warcraft, and a lot of my foundation for how I think about the world is through whether I realize it or not, through the subconscious lens of what I did there. And if you think about why, this sounds like an overly hypothetical and meta question, but why do we do the things that we do? And that could be everything from in gaming, in life, in relationships and everything in between. I always think back to, okay, I would spend hours upon hours, I'm going to throw out some references to World of Warcraft. Those who understand them will appreciate them, those that will not just trust me that they're just, they make sense. I would spend hours in the Barons collecting feathers from plane striders so I could accomplish this quest to get experience and thus level up and get new weapons and get new armor and be able to fight bigger bosses.
(41:50):
And if you think about the mechanics of that, it was called a grind when you were leveling and it was called a grind for reason because it was work, it was just like it was clicking buttons and it basically going from place to place, using your fingers and keyboard to attack something and then collect its loot and then go back and turn it into someone where it can be boiled down to a compilation of keystrokes, which would not look too different from say, data entry into a spreadsheet. And that could be considered someone's job. And I would venture to say that in most cases, someone would much rather be grinding and leveling a world of Warcraft by killing beasts and having a drop loot to bring back to Quest master. Then they would be just inputting random data into a spreadsheet in a similar type of fashion using the same tools and devices.
(42:40):
But basically the same thing is skinned as a game and gamification in the case of World of Warcraft as opposed to a job and work as it is for data entry. And that can be applied to taking out the trash that can be translated to all these different things that we don't want to do. So what is it about world of Workout that makes us want just to basically do work and not call it work? And it seems obvious it's games, but how you apply that game theory and those mechanics to other facets of life I just think are very interesting. And there's a lot of implications to that when you consider just motivations, incentives. That's where I've probably done most of my reading historically on business books and stuff, is this behavioral science of gamification and how we can create, whether it be for business purposes and building a product that includes game loops and positive outcome incentives that keep people coming back and engaged and thus drive retention just to life of just setting up people oftentimes set like atomic habits and building a foundation for day-to-day habits through gamification and setting up rewards triggers to incentivize yourself to do things positive on a day-to-day basis.
(43:55):
Understanding those will compound over time and lead to overall benefits and outcomes in one's life. So I think there's implications, well outside of business to it, and I think that there's a lot of power to it and sort of this weird sort of this hypnosis that can take shape whether you realize it or not, of perceiving something that you should be doing that could otherwise be perceived as work, going to the gym, doing certain tasks and chores and other things, but making that fun and engaging in a way that makes you want to do it and that benefits your life.
Dan Freehling (44:27):
Such an interesting way to look at it. And yeah, thanks for going there World Warcraft and bringing that background into it. Nothing has to be devoid of fun. It's a choice to make something not able to be enjoyed and fun and you can kind of bring this into it in life and business, and it's something to really think about. And I think it doesn't sound like business unquote, but there's some really deep and high level thinking that goes into this at the highest levels of business. And it's something that people should really consider.
Sam Simmons (45:02):
And I think a lot of, let's say non non-tech or that's non, I don't know the right way to frame it, but there's a lot of industries that would say, I don't need games. This isn't game, I'm an accounting firm. Why would I need gamification? But I just think there's a lot of ways to use hidden game loops, not in a way that's nefarious, but to benefit everyone. I mentioned just life habits. I literally use gamification to get myself to journal every day, and that's purely because if everyone is Duolingo, they know this experience, but you have your daily streak and you don't want to break that streak. So you keep going back to learn a language on a day-to-day basis. They are 10 people would probably cite Duolingo as one of those gold standard gamification case studies. And I think that those mechanics apply elsewhere where, like I mentioned journaling, I do this every day.
(45:59):
I journal, I put a check mark and every day I don't journal. I don't put a check mark and next thing you know, I've journaled for seven days in a row and I'm like, crap, I have to journal again today because I can't break my street and streak after seven days. So whether it be at the gym, whether it be other things, I think there's plenty of ways that that could be applied to the accounting firms of the world and other businesses. And so it's easy to just write it off you, like we're talking about all Warcraft, this is dumb. I have no application to this. But I think it would behoove those listening and others who may not be listening to consider gamification and how it could impact your business because there's actually some real interesting mechanics to drive retention, drive growth, whatever the key KPIs are, there's a gamification mechanism to enhance it.
Dan Freehling (46:40):
Yeah, thanks again for sharing that. You talked about a lot of your business book leadership, book reading, being around gamification, atomic habits for one. What other leadership books, other resources do you find yourself coming back to the most often?
Sam Simmons (46:55):
Yeah, so I'll say two. I actually have on that checklist I have for journaling, I have reading daily on that checklist. So reading does tie into gamification, not because I read gamification books, but because I hold myself accountable to read daily by gamification and tracking my streaks. So it all kind of plays in together. I mentioned earlier too, how I kind of got into the spiral of binge learning business in the time before Mint Pass and just in a career flux for a while there. I don't necessarily reject business books, but I found time and time again that I would read a business book and my life or my business efforts wouldn't change that much. And in fact, it's basically like a re-skinned version of the same platitudes just said differently by the author. And I think to be frank, the most successful business books are successful because an author finds a different way to frame something that maybe people understand better, but in fact, it's the same learnings that everyone else has had at different points in time or the same teachings I should say.
(48:02):
But it's just the ability to convey them in a easier to digest manner. So that is to say I'm just not that big on reading business books. However, what I actually have credited most to sort of, let's call it some function of business performance leadership style in some cases, mental wellbeing as it pertains to my life at work, I read a lot of historical, both fiction and nonfiction. And I think it's interesting learning from the past in a way that can impact the future and not from, there's obviously a lot of key moments in the world history that are important to learn from a geopolitical standpoint. But I think just about leadership and life lessons from people who have come and gone and how it can play into what the problem of the moment is. And I say this not only from across time, but across cultures and reading a lot about Asian history and learning and embracing a lot of the learnings from that world and how it can be applied to business and life. And like I said, I've found that a lot more beneficial than reading the same mix of platitudes out of a business book in recent years. So that's where I spend most of my time these days. And typically if want to ask me, Hey, what books do you recommend? That's what I typically go to.
Dan Freehling (49:23):
What an interesting perspective. I tend to agree on the blah business books with the seven habits of this, the 40 secrets of this kind of a thing on the history books, what are some examples of ones that you've found particularly helpful?
Sam Simmons (49:42):
So I'm in a Japanese history kick right now. So I read Shogun before watching the TV show, which is it's water Not Watered Down, but it's an extreme version of Japanese history from a non-Japanese author in the 20th century. So it's not truly representative, which actually then after that long read led me to probably a longer read, which I'm reading right now, which is Musashi, which many probably haven't heard of it, but it's considered the Gone With the Wind of Japanese culture and was written many years ago. I think it was in the authentic, the Japanese way of life in around the 17 hundreds turn of the 18th century. And I think it's interesting, this whole, I learned a lot about honor and duty and obviously the context of that then is a lot different than the context of that. Now this is just a side mission into my own life, but I'm actually expecting my first child in a few months.
(50:45):
So how those lessons apply to my life and sort of this transitional time for me, and not only with my family but in my business of creating the startup and how honor and duty play into that I found to be very helpful. And it's almost like cliche in today's society, but they really delve into the theme of karma. And there's many instances this has happened in Shogun in particular, where some crazy stuff happens, bad stuff happens, and one of the characters just say, ah, that's karma. And at least not in those words, but in the way that we would say it today. But whereas for us it's like, it's almost like a cliche for them. It was a way of life and just certain things are out of your control, certain things are just left to fate, and why fight that as opposed to just understanding that is my fate, is my fate. What's the point of stressing or worrying about it? One of those things a lot of you just have than done, but something I'm reminded of a lot and when things hit the fan on a day-to-day basis as they can often when it comes to the startup world, it's helped me be a lot better of having the same approach of like, ah, that's the karma. That's my karma where I can control it. So what's the point of being worried about it?
Dan Freehling (51:58):
Yeah, I can see all the tie-ins to the poker analogies too in a lot of ways. And something you wouldn't think that Japanese history and poker would have too much in common, but it's pretty fascinating how it's focusing on what you can control and not putting your attention at trying to control things that are beyond you. And it's just something where it's such a third line I'm hearing and everything you've shared today.
Sam Simmons (52:21):
Exactly. And it's kind of in the same way we talk about re-skinning the same lessons. I found it refreshing to have the same things that I know that I understand, but I sometimes need to do better. That and having those things reinforced in various ways. So obviously we look at poker and gamesmanship as one way, but then looking at history and influence from other cultures and icons and just people that are legends that I respect, that I appreciate retrospectively and allowing that to underline a point I think is valuable. And that's again, back to the question, that's where I get most value out of resources is finding different mediums to reinforce a lot of those same lessons that I find bring me the most value on a day-to-day, week to week, month to month basis.
Dan Freehling (53:13):
It's just great perspective and really appreciate you sharing it. So what's the latest with Pass? Where are you all in your company journey?
Sam Simmons (53:23):
Yeah, so we are, depending on when this is published, we are either heading into or have shortly launched or shortly before this launched our public beta. So we've been behind the scenes with a few hundred friends and family testing out the app over the past few months, getting great feedback along the way, finding out what's broken, being able to fix it without having too much egg in our face. And pretty soon we're going to be doing a pretty big launch activation, which if this goes up in the next few weeks, there should be still information out about, and that campaign should still be live, so we have a big partnership coming out. Best place to find us is at mintpass.com, or you can find us on X slash Twitter at MintPassTravel, and we're looking for users. So pretty much for anyone listening, if you travel a lot and want to give it a try, we're going to be in basically invite only basis. But if you want to reach out to us directly and say, you heard us here, I'm happy to give that advance access to anyone who might be listening and might want to give it a try, whether it be for upcoming vacations, upcoming business travel, anything in between, as a way to not only discover, but also store your future recommendations.
Dan Freehling (54:38):
Awesome. Well, thanks for sharing that. Exciting times ahead on the personal front and business front for you. It sounds like Sam, such a pleasure talking with you. Thanks again for taking the time and joining me.
Sam Simmons (54:46):
Yeah, absolutely. Thanks so much for having me. That was a lot of fun.
Dan Freehling (54:49):
Thanks to everyone listening, so if you've got something out of this episode, if you could please share it, a friend or a colleague, and take a second to leave a quick review. Even just the Stars is great on whichever podcast app you're using goes a long way in helping others to find the show. If you liked this episode, check out some of our previous ones on all things leadership, organizational culture, and career development with real deal executives and experts I respect and trust. Here's a clip from episode two with Amy Rupert Donovan, as sought after executive coach and one of the pioneers of professional coaching.
Amy Ruppert Donovan (55:18):
When the leader is invested in their own development as a human being, when they're able to manage and regulate their own emotions and understand themselves and have a high degree of self-awareness, I think that makes a huge difference for how it impacts the culture of the organization. Like it or not, when you are leading an organization, number one, you don't get to have a bad day. Every good leader, I know that's their philosophy. You don't get to have a bad day because you are modeling behavior for the entire enterprise and it certainly does trickle out through the whole culture. And so working on yourself as an individual. And I do people think, when I say executive coach, they sit there thinking, I'm working on them, putting together great strategies and budgets and blah, blah, all that stuff. No. A lot of times it's around this stuff and how do I gain more awareness for myself so I can bring more of myself to this role as a leader and make the organization better because of it? I think that is one of the hallmarks of a great leader.
