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Founder Files


From The Founder Files – the podcast that’s like eavesdropping on a conversation with a successful entrepreneur over a fireside chat. Join Cameron Coutts for unfiltered stories and insights from scaling founders around the globe, as they share their ups, downs, and everything in between. With practical tips and real-life experiences, The Founder Files is the most authentic podcast for entrepreneurs looking to scale their own businesses and learn from those who have been there before.


Cameron Coutts (00:02):

For many entrepreneurs, one of their core goals is getting to the point where they can successfully exit and sell their business. But my main question to you is, so what? Let’s say that you achieve that; what does that measure of success mean for you as a person, and for your business, as well as for your stakeholders? And what it is that you’re trying to achieve?

I’m going to leave that question hanging because our next guest is going to give some really good insights of his own experience in terms of exactly that question. This is Mark Ross-Smith, who is the founder and CEO of StatusMatch, which is a customer loyalty program for Global Airlines.

He’s got an interesting journey and story that I’m going to let him tell that’ll probably make you contemplate mostly two things. What does the word successful mean in successful exit of a company? And secondly, just the non-linearity of a career, especially for entrepreneurs, and how many different angles that this road can take you down.

Mark Ross-Smith (01:04):

Airline loyalty is highly profitable. In a lot of cases, the loyalty program itself can be worth more than the whole airline in terms of valuation on the market. And that’s, quick 101, because the loyalty programs are marketing tech companies. The way they’re valued on the market is very different to an airline aviation business.

Cameron Coutts (01:29):

This is The Founder Files, real stories from real entrepreneurs about the joys and challenges of leading people and business.

So Mark, thank you very much for joining The Founder Files. It’s great to have you on here. You are my first international guest from Australia on the show. It’s going to be a good conversation. I think without giving too much of a preamble on you, because I can worry about that later, why don’t you just introduce yourself to our listeners.

Mark Ross-Smith (01:56):

Good day, mate. From Australia, not living there anymore. I think the accent is a bit worldly accent. You live overseas for a while, your accent blends from different cultures and you don’t really know what it is anymore so I don’t even know if I’ve got Australian accent. But anyway, it’s not the point.

Yeah, Mark. I’m CEO, co-founder of It’s a startup, it’s about two years old now. We started in the travel industry in the middle of the global pandemic, the worst time to ever start a travel startup, in the whole of human history I think. And we thought if we can survive global pandemic, we can survive out of a pandemic, we’ll thrive out of a pandemic. So it was a really good test to start then. We worked with Global airline brands and hotel brands to help them acquire new high-valued customers in new and innovative ways that they traditionally have not been that amazing at doing.

We work with nearly 10 airlines right now that we’ve signed up in the last sort of couple years. And anyone in the travel industry knows that doing deals with big global dinosaur airlines is pretty difficult. I think we’ve managed to get through that. Business is doing pretty well.

Prior to that, I had a thought leadership blog, Travel Data Daily, it’s free, you could read it. It’s all about how to monetize data and make money out of loyalty data, especially in the travel and telco industries.

Prior to that, in the telco industry, had a social network that me and a buddy created in Australia. We had that for seven years, had an exit in 2013 out of that. So there’s this entrepreneurial theme in my career with a couple of corporate gigs mixed in there. So, keen to discuss more about this.

Cameron Coutts (03:52):

And I think the biggest theme going through that besides the entrepreneurial side is obviously just the customer loyalty. I think those two go hand-in-hand because I mean you can’t be a successful entrepreneur without loyal customers, otherwise you’re constantly chasing your tail.

But you mentioned about the social media and the social network that you started. Whenever anyone hears that, they just think immediately, all right, Facebook, Instagram, Twitter, TikTok, WhatsApp, all these giants. But people tend to forget what social networks actually are in their essence.

And that was a successful exit. You sold that to a listed company. Tell us a bit about that. What was that like?

Mark Ross-Smith (04:31):

Yeah, so in my young, innocent, youthful days, me and now my buddy, we were working jobs in another company, decided to leave. The old MySpace was the big company at the time. They’d just sold to, I can’t remember who they sold to. It was like six, $700 million or something. And we looked at it and thought, “Yeah, we want that too. We want that 700 million bucks. We want to champagne every day, every meal for breakfast the rest of your life. That sounds great. Let’s do that. Let’s create a social network and sell that for 700 million to Microsoft as well.”

Sounds good. A little bit harder than that in reality, but we started there. It was called SMS Fun in Australia. It was all based around texting on your mobile phone. You could send free text messages from a website that we’d created. And this is back in the day when text message, you actually had to pay for these things. It wasn’t like iMessage and WhatsApp these days, where it’s all free. This is back in the day, it was 20 cents to send a text to your friend that was still limited in characters and T9 keyboards and all this kind of stuff.

We started there, built it out into a full-blown thing with chats, forums, photos. Our claims of fame is we were the first to create a Dislike button on something. That was our big thing.

Cameron Coutts (05:48):

Was that you? That was all you, eh?

Mark Ross-Smith (05:50):

Totally, 100% all me. It was actually very interesting when we first introduced that, it split people basically. People, they either liked a lot of stuff or disliked a lot of stuff, categories. And we had open feeds where you know could have your friends’ feed and you see what your friends could do, but then you could share the feed with the entire network and there was just one massive global feed. If you could imagine hundreds of thousands of people on there just sort of updating their status and stuff like that, and you just see everyone’s. It’s just a crazy “drrr…” The Matrix screen and the chats, you just see all that stuff. They were fun days.

So that was in the telco industry. We worked with some of the big carriers there in helping them get new customers, into subscriber base. Really effective and made a lot of money. It was a lot of fun, actually.

Cameron Coutts (06:44):

So you sold that business. Tell us a bit about that journey because you’ve really glanced over this because for a lot of entrepreneurs and in startup space, that’s the goal. Getting to the point where I’ve scaled my business to the point where it’s a sellable asset, someone’s going to buy it, I’ve exited this, I’ve made it as an entrepreneur.

And you just been brushed that aside. It’s like, “Oh yeah, yeah. We did that.” That was quite cool and interesting. Give us a bit more detail. What was that exit like? What was that experience getting up to that point? And what was it like exiting your business that was so much fun at the time?

Mark Ross-Smith (07:21):

Looking back, the most memorable moments was not the sale at all. In fact, that was probably the worst. There’s a bit of money involved but you take you that out, and that was actually the real worst because you’ve got all these crazy contracts and due diligence stuff and lawyers and just handover documents and all sorts of stuff that as an entrepreneur, you don’t think about it, you don’t really want to do it.

You want to build something, it’s sexy. Maybe you like the coding part, maybe you like the management part, whatever, there’s something you like about the business. You start something from scratch. It’s your little baby and you see it grow, you see it flourish, you see it do more cool things and you really get attached to it.

It was referred to as my girl on the side. My girlfriend at the time, she’s like, “You’ve got a girl on the side?” It’s actually my wife, is the business. So my real girlfriend was actually the girl on the side.

You get really emotionally attached to these things and one day you sell it. It’s kind of like, I guess, like your kids leaving home. They get to a certain age. It’s like, “I’m leaving now, I’m going to go live with my friend.” It’s kind of like that. They’re leaving and you feel quite sad. I felt a bit lost to be honest. What do you do now? You’ve been working for so many years towards this goal that you don’t really know what the goal is. The goal is, as an entrepreneur, deep down back of your mind, you think, “I’ve got this tech business, I’m going to sell a lot of money, it’s going to be awesome. Going to get a yacht, I’m going to do all this stuff.”

I don’t think that’s actually what you want. It’s actually the journey that’s far more… Looking back, the journey is far more exciting. It’s the small moments. I remember after I think a couple years in, our burn rate was just astronomically high. We were running on banner ads and emails and traditional sort of media income at that point. But our burn rate was, I don’t know, a 100,000 a month or something like that at that point, mostly on sending text messages to people because they cost more money still and we were giving away for free.

It gets a point, “Well, I actually can’t afford it next month. What do we do? Cash is not coming in.” Navigating those moments, looking back, was actually really fun because it’s kind of challenge. You knew it was going to work out, but you weren’t a 100% sure. Obviously we survived it thanks to credit cards. They made it work.

To be fair, paying 20% interest on a credit card is actually not a bad deal considering when you know you’re going to get the money back in a few months and if you sell it’s totally worth it. It’s kind like a bridging load in some ways. So that kind of worked out.

There was a point when we knew in that business that our limitations, I mean we were young, early twenties, guys starting this. We’d got a few other people around us on board doing different things and you realize what you’re good at, what you’re not good at. You’re young, you’ve got aspirations of other things you want to do as well.

And so we realized that this business would be better in someone else’s hands, once you get to this certain sort of level. Now, a few years later, I know what I’m good at and that’s getting from zero or not making money to being profitable. So that, we’ll call it an early, mid-stage business. But once it’s ticking along and profitable and trajectories itself, at that point I sort of look and go, “Is my job done now? Maybe it’s time for someone else to take over, someone that actually is just good at this next part.” Because I know what I’m good at. I’m pretty good at that early stage, actually.

We didn’t realize that in that business. We weren’t that self-aware of who we are. We were just a couple of kids that started something and did pretty well at it. So selling it was a bit of a letdown, actually. Even though it’s actually the thing you think you’re striving for. I don’t think it is. I don’t think, looking back, it was the thing we were actually trying to get to. But we got there fortunately, went through that process, did that transaction.

It was pretty good. It was sort of a cash deal. We walked away from that with a bit of a handover time. After that, what do you do now? Basically unemployed and just coming out of business. You think, what do I do? Do I go get a job now? I don’t know. What do I do? Do I just start another thing? I’ve signed these crazy documents say I won’t start something similar, so that takes you out of that game.

So for me, it took a while to figure out what’s next and I thought, “Okay, I’ve done the telco media business there.” I was always traveling around the world as part of that business, quite a lot. 150 flights a year kind of thing, conferences and meeting people and stuff. I loved that and I thought, “I’m spending all this money on flying, how do I get cheap flights?” So I thought, “I need to get in the airline business because airline staff get cheap flights. They get cheap business and first class. Why not? That’s the next goal.” That kickstarted the next process of moving into the loyalty in the airline space.

Cameron Coutts (12:53):

So I want to dial it back a moment just towards that exit point because also what stuck with me in the way that you described it is so many entrepreneurs, what the biggest thrill and rush is solving the most complex problems when your back’s up against the wall. So many entrepreneurs, that’s what the thrill is. People talk about adrenaline junkies, I’ll call them entrepreneurial junkies. That’s the high that we look for in business.

But there’s quite an existential nature to the way that you’re explaining what this exit was like and the vision I have in my head is about the fact that, “Yeah, I’ve sold it.” But then you get to almost like this edge of a cliff and there’s just fog in front of you and you almost stood there, or maybe even sat there with your legs dangling off the edge, and you were like, “What now?” And your pockets are full of cash, you’re looking over into this view. It’s like, “I’ve achieved this goal that everyone wanted to.”

What was that experience like for you as a person having achieved everything you thought you wanted to?

Mark Ross-Smith (13:56):

I remember the day that, you call it the handover date, the contract date that I stopped. It just so happened to align with my whole life at that point. I’d planned this two-week trip with my girlfriend at the time to Europe and just happened we were departing the following day. It was a Saturday. So this contract was a Friday and then the Saturday we were flying off. And I’d booked this six months prior on points. So it was a redemption trip that I couldn’t change, couldn’t cancel and I’d booked a long way in advance. So it was a bit good timing that worked out in those days.

I remember getting on that flight. I’ve got my phone and the emails stopped. And suddenly it was like, “I don’t have to worry about anything anymore. I don’t have to talk to anyone, I don’t have to do anything. I can just do whatever I want.” And it’s like, “What do I want to do now? I don’t know.” So you feel a bit lost.

Literally, it was a morning flight that next morning and we’re at the front of the plane. I thought, “Well, I’m just going to invest in champagne for the next day or so when we fly there.” That’s my immediate investment. I think having that holiday there, that vacation, just relaxing, zero work, which is something… You work in a business. Having holidays is, for us, pretty rare. Everything you do, you think about business 24/7. You’re out on the weekend doing something with your family, you just can’t stop thinking about the next product, or, “What if we did this?” Or, “How about this?” Or, “That’s a new way I could approach this client.” There’s just stuff that’s just always going through your head. I can’t turn off. I find it very difficult to.

That was the first moment where I thought, “I have to turn off. I’ve got nothing to think about now. That’s gone. That business, I’ve kind of broken up with that one.” Or, “That kid’s left the house,” kind of thing. It’s that kind of thinking. I think it was really good to go through that because how else would I have learned to switch off?

It’s getting very deep now, is it? I don’t know how I would switch off. So I think it’s a pretty good life lesson to go through, just to recalibrate and help ground yourself, get ready for the next adventure.

Cameron Coutts (16:20):

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And what was the next adventure? You packed your two suitcases, hopped on a plane, then ended up in customer loyalty for airlines. What happened? What was the next step in-between that while your natural entrepreneurial mind was constantly looking for what customers experience in our businesses could do better?

Mark Ross-Smith (17:27):

I was already flying around a lot. I was one of Qantas, the Australian airlines, one of their top customers. I got to meet a lot of management team and they treated me really well. They’re very good at what I’ll call customer engagement, customer retention stuff. It’s one of the top flyers. They’ll just shower with gifts and experiences. One thing I did learn from Qantas as a customer is when they do things for you that you can’t buy yourself, there’s this really strong emotional connection to that thing.

I’ll give you example. This is not something every company could do every day, but they launched this new super VIP tier, it was called Platinum One at the time. This is for the top of the top customers, their very best customers. They wanted to give these people experiences and so they invited me to fly with John Travolta on his 707 aircraft at the time. It was painted in the Qantas’ livery and the theme, the colors and stuff. He was actually the pilot of that flight. I think it was about 10 of us on board. It was just a joyful flight, champagne, cocktails in the sky, couple hours. Obviously, pilots ae not drinkers, they [inaudible 00:18:44]. It was a lot of fun, and you can’t buy that. You know what I mean? There’s no website you’re going, “I want to fly with John Travolta on his plane and take photos.” I wish there was, be kind of cool. Damn expensive, though.

So because you can’t buy it and you’ve got this brand, Qantas in this case, it’s a “money can’t buy, once in a lifetime” type thing. What’s that worth? What’s that really worth? I don’t know. I don’t know the price to that. But the emotional connection I had to that, the emotional connection I have to the brand now, to Qantas, the brand, is through the roof. I don’t live in Australia, but I still talk a lot of really good things about Qantas as the airline.

What happened is they’d actually, without me knowing it, turned me into a bit of a brand ambassador because of this connection that they’d built through these kind of experiences and events and things that they were inviting me to. It was all free, obviously, because you’re a good customer. I took a bit of that knowledge and I thought, obviously I wanted two flights moving forward, so I picked up my bags, moved to Hong Kong, that’s where Cathay Pacific is there, that’s the main airline in Hong Kong. And I asked someone there for what’s called a status match, which is I said: “I have this elite status level with this airline here, and if you give me the same with your airline,” the gold levels, the platinum, this kind of stuff, these are things you got the lounge access, the priority boarding, all these kind of perks. “Basically if you give me the same with your airline, I’ll switch my business across to you. I’ll start flying you instead of the other guy.” That’s status match. Been around for about 35 years, this concept.

And the airline at Cathay, they said no. I thought it was a bit weird. Why don’t you want someone that just moved to another country? I need a bank account, I need a credit card, I need a new airline to fly, I need all the right things. And they’re basically saying no to someone that has proven themselves with a competitor. Why wouldn’t you want this customer? That was a bit weird. So I asked Singapore Airlines the same question, because I think it’s the same region. They said no. And I thought, this is messed up. Why don’t airlines want high-value customers that are coming to them and saying, “I want to spend money with you.” “I don’t want you.” Why is that?

That’s when I decided this is what I’m going to do next. I’m going to do a status match. And this was in 2014. And so I started attending industry events. I just paid my way along just to learn more about how the business of airlines and airline loyalty worked. Had a lot of fun at these events. Started a blog in that industry, fast-forward a few years and then had a call from Malaysia Airlines one day and they said, “Do you want to come down and run our loyalty program?” And then I said no. I said no first, actually. Got a good life in Hong Kong, not interested. They said, “Just come down, meet everyone.” So I flew down, met them, said yes. It’s not [inaudible 00:21:52], you get these kinds of opportunities to pretty senior role in airline like that.

So I went down and I took the entrepreneurial thinking. I took the “I’m a frequent flyer” thinking and tried to pack that into their existing loyalty proposition, and basically try and run it like a startup, basically. Try and run the loyalty program like a startup, do new things. How can we make more money? How can we create new products really easily? This is a corporate job. Coming from the entrepreneurial world where you’ve had your own businesses, you’re your own boss, things generally work pretty fast-paced in your own business, coming to very highly bureaucratic government organization with eight levels of approval to change the spelling of a word on an email that’s going out next week. That was a fun challenge.

Cameron Coutts (22:53):

It sounds like it. And what I’m super curious about is this experience that you’ve had right at the coalface of customer experience and on all sides of this table in terms of being from the customer’s experience, being from the person that does a loyalty program, being an entrepreneur yourself, generating customers. You’ve had that experience there. From a customer retention, customer loyalty perspective, getting this John Travolta-level of experience, for most startups that sounds amazing, but it isn’t necessarily feasible. But what you described there is that emotional connection to the company and to the brand as a customer. What are some of the things that other business owners could do to at least try and emulate that to an extent? Or what should they at least think about in trying to vet up something like that?

Mark Ross-Smith (23:53):

So I’ll share a couple of things. For any businesses out there thinking of some sort of loyalty proposition, it’s super critical to start with the end in mind. What does success look like for a loyalty program? Because you shouldn’t launch one just because your competitor John has one. That’s the worst idea. You want it for a real reason. That might be to sell more stuff, to grow their shopping cart or basket size. It might be to increase the share of wallet. And share of wallet actually is the number one metric that good airlines use to measure loyalty. Might be to reduce churn or attrition, or just attract incremental business.

Generally, you want to pick one of these as your hero goal, the one thing you want to do. I’ll talk to share wallet quickly because airline loyalty is highly profitable. In a lot of cases, the loyalty program itself can be worth more than the whole airline in terms of valuation on the market. That’s, quick 101, because the loyalty programs are marketing tech companies. The way they’re valued on the market is very different to an airline-aviation business. An airline-aviation business, at best six to eight times profit earnings ratio is the kind of market value-ish on that. Whereas marketing tech co, what, 20, 30, 40 times, hence loyalty programs can be worth more.

So the number one metric is share of wallet. This is really how loyal is someone to your brand. I’ll just give you an example in an airline context and I think you can see how this applied to other industries. Let’s say you only fly once a year to visit grandma. You’re doing two flights, that’s it. That’s 100% of your loyalty for flying, you’re not doing anymore. So if airline A gets those two flights, you’re 100, you’re a real loyal customer. You always fly this one airline, you love this airline, you love the peanuts, whatever it is. You’re into that, 100% share of wallet. Whereas your cousin over here, he’s an ultra frequent flyer, 50 flights a year. He’s in first class, he’s spending tons of cash, but he’s splitting his business between two airlines, because he can, for whatever reason. He’s actually less loyal to that airline than you are because that airline’s only getting 50% of his share of wallet, whereas they’re getting 100% of yours.

So in terms of marketing CRM, what you should target and how you should target, they shouldn’t target you to try and get more business out of you because you are already really loyal. Whereas your cousin, he’s spending more. So when you look at it go, “This is one of our top customers, this is really great.” But actually, his ability to spend even more than that is double. Whereas they’re only going to get $200 a year out of you for your two flights. But your cousin, he’s spending $20,000 but he could spend another $20,000. So if you can figure that out, if you can figure out what sort of share of wallet you’re getting out of each customer, you start treating them a little bit differently. It changes the way your CRM and everything behind that because it may be that your best customers are actually where there’s sort of more headroom to grow the business and capture more share of wallet out of them.

Cameron Coutts (27:23):

That’s really insightful. So, where are you at now? How are things with Status Match? How are things in your very non-linear career and interesting path and journey? What does the present look like? What does the future look like?

Mark Ross-Smith (27:35):

Yeah, Status Match is going really well. It’s a couple years old now. We’ve got a bunch of airlines on board. We’re growing. We’re profitable since day one. We’ve raised no money. It’s all self-funded, self-built as well, growing team. Got a team all around the world, different countries. In fact, our team has actually never all met together, ever. Between border restrictions and not being able to fly and just everyone’s everywhere, we’ve never actually met. So maybe there’s a Christmas party coming up where we should all meet or something. But business is good. Airline industry obviously very strong currently today. As everyone knows, it’s very expensive to fly to a lot of places right now. Airlines are totally milking it, which is great for them. They’ve been hurt last couple of years so they clipped a comeback there.

The loyalty program on the back of that, airlines are looking to acquire new customers to keep that going, and more high-value customers, which is where StatusMatch, our business, fits in. If you have a silver, gold or platinum status with an airline or a hotel, they’re the kind of travelers we help. We help them get that equivalent status with another airline or hotel, so it helps them move brands a little bit easier. It’s kind of like porting them over our phone from one carrier to another, except you actually keep both lines active in our case. So, it’s kind of cool. So you can have gold status for two different airlines. My friend was saying the other day, “What’s better than having a brick of gold? And that’s having two bricks of gold.” So it’s kind of what we do, we get you that second brick for a lot cheaper than you spent to get the first one.

Our business is looking really strong. We’ve got a lot of great partnerships coming up: banks, airlines, hotels, which is really fantastic as a startup. Applying some of the lessons learned from my early years into this, which you have to do it, otherwise you’re just going to go through the same motions again. So, applying a lot of learnings there. Lot to learn from corporate as well. Going back in corporate I think was a good move. Sort of plug some of those holes in the knowledge gaps and stuff. Just those little things that you don’t learn when you’re doing your own thing. So, quite helpful there.

Yeah, so we’re just seeing a lot of demand from people that are traveling, people who have elite status wanting to get more elite status because no one wants to lose the perks. Once you’ve tasted that business of first class, security line and the priority boarding, when they call first class and you walk past 300 other people that are in economy, it’s a pretty good feeling, “This is why I fly this airline so I don’t have to line up with everyone else.” People are pretty scared to lose their status and so we help people keep that status, at least with one airline or another.

Cameron Coutts (30:33):

Going back to what I said earlier about entrepreneurs loving these backs-against-the-wall complex problems, what are the ones you’re facing now? Because it doesn’t sound like your back’s up against the wall. Sounds like business is doing pretty well, you’re growing quite clearly. You’ve learned from the startup, you’ve learned from the corporate, like you said. So, where’s that kick? Where’s that next high that you’re getting in terms of solving business problems? What’s in front of you now?

Mark Ross-Smith (30:59):

We’ve been on the front foot with a lot of this trying to proactively get out there. So we are leveraging a lot of media stuff, real-world media, speaking events, I do a lot of that recently, to try and not have the chance to get our backs push the wall. Figure offense is better than… That kind of thing. So we’re just out there doing more of it. If anything, like any business, we’ve got a pipeline of airlines and stuff we’re talking to, very difficult to do business with some airlines. That sort of sales-pipe process, could take years, could take years. It’s not an industry I recommend if you’re thinking of creating a startup. And that’s me being connected already and our team being pretty connected in this space. So I think the big challenge we’ve got right now is some of the slower airlines, onboarding them as clients. That’s probably a big challenge, but we’ll get through that. Yeah, that’s a big one.

Cameron Coutts (32:01):

So Mark, what’s the one question that I haven’t asked you that I should have asked you, that you’d like to answer now?

Mark Ross-Smith (32:07):

That’s a good question. I think anyone listening to this is going to have their own question that I don’t know and you don’t know and they would love to ask me. So really the question is, how can anyone listening to this ask their own question to me? In which case the answer would be: add me on LinkedIn.

Cameron Coutts (32:25):

That was actually going to be my next point. If anyone wants to get hold of you, where could they go?

Mark Ross-Smith (32:29):

Yeah, that’s on LinkedIn. Reactive on LinkedIn. Otherwise, check out

Cameron Coutts (32:34):

Mark, thank you so much. All the best.

Mark Ross-Smith (32:36):

Thanks a lot. It’s been great.