The Stuart MacDonald Approach: Strategies for Marketing Success

Posted by Anant January 11, 2023

Stuart was the former CMO of Freshbooks, and previous to that he was the CMO of Expedia and the founder of He also runs the Mesh Conference, which gathers together leading thinkers and talented innovators who have done great digital work.


→ History and impact of Expedia Dossier, a Canadian arm of Expedia

→ How Expedia Dossier changed the way Canadians book travel

→ The challenges of travel booking before the emergence of online travel agencies

→ How Expedia Dossier aimed to empower consumers by giving them the tools to find and book the trip

→ Putting customer first and removing barriers to find their desired trip

→ Recognition that customers find planning travel fun and enjoy exploring options

→ Providing smart tools and good options for customers

→ Goal is to help customers find their desired trip at the price they want

→ What is Mesh Conference

→ And a whole lot more


Stuart’s LinkedIn

Mesh Conference



Bronson: Welcome to another episode of Growth Hacker TV. I’m Brian Taylor and today I have Stuart MacDonald with us. Stuart, thank you so much for coming on the program.

Stuart: How are you?

Bronson: I’m great. I’m so glad to have you here. You’ve done some really interesting stuff here. The form here. Yeah, absolutely. You’re the former CMO of FreshBooks. And previous to that, you were the CMO of Expedia and you were the founder of Expedia Dossier, kind of the Canadian arm of Expedia. So we have plenty to talk about. And you’re also the co-founder of a conference. You have a consulting gig. You do. I mean, you kind of you’re all over the place here. But let’s start with Expedia. All right. So you founded Expedia dossier and essentially you changed the way Canadians travel. I mean, it sounds like hyperbole, but that’s actually what happened. So tell us, what was travel like before Expedia dossier and kind of what do you do there? What was that like?

Stuart: Well, I mean, the travel before well, if you sort of say travel before online, it kind of sucked. And I and I do mean that the actual travel process, the travel itself, like getting on aircraft and stuff like that is probably worse now than it was back in those days. But, you know, we’re talking about a time when when connectivity and sort of the digital realm was just getting going. And so planning and purchasing travel typically involved picking up the phone, being on hold to talk to somebody who really didn’t know very much and probably didn’t like you very much and wasn’t being paid a lot, but somehow they had this magic box and you had to talk to them. And so I just knew that that that didn’t make any sense. I thought there had to be a better way. I really had this strong sense that that travelers were being, you know, were being are being taken advantage of. And, frankly, the the the channel was being set up was in a certain way, the value chain was set up that the trade was all about itself, and they didn’t think about the traveler. And so from my perspective, I just thought there had to be a better way. And the and the gravity to sort of move from a a phone based or going into a going into a strip mall or whatever, to sit across the table from somebody to move to an online self-serve model where where the traveler themselves could could find the trip they wanted and give them smart tools. It just made all the sense in the world.

Bronson: Yeah. So would you say that the key insight was that you just actually put the customer first instead of the value chain of all the people taking their cut?

Stuart: You know, as crazy as it sounds, that was sort of it. A lot of people have asked whether this was whether it was about trying to do an online travel thing. Well, you have to remember, at this time, online travel didn’t really even exist when we would talk about online travel. I mean, I would go to the proverbial cocktail party and talk about online travel. People looked at me like, you know, a dog watching television. It’s like, what is this thing? Are you selling books about travel or. So the key insight was that if you could, I really believe that if you could plug smart tools and in and and good access to great options and make it easy for people to use and just get the other people out of the way of put this in front of them that there were lots of people who would feel much better being able to drive that. And so that it was it was really never about creating an online self-serve travel thing. It was always about trying to find a way to make it better for travelers to be able to find the trip that they wanted. And, you know, one another key insight here was that I had been in and around the travel category for a long time. And so I had known that people a lot of people sort of see the planning part of it of of of a trip as part of the trip itself. They see that as some of the fun. Now, some people not so much they want other people to take care of them. I’m actually a big believer in traditional travel agents, by the way. If you’ve got a traditional travel agent that you feel good about, for heaven’s sake, they’re worth their weight in gold and stick with them. But, you know, there’s there for for a lot of people. They enjoy digging in. They enjoy sort of looking at the options. It’s part of the fun. And so they they think that the trip starts when the planning starts. And so, you know, give people smart tools and give them give them good options and let them go. Yeah. And if you just if you just say, you know, I believe in you, I’m going to center something around you and make sure that it’s it’s you that I’m concerned about. You know, I we we’re building this. We never built it for the early adopter geeks with, you know, on their dial up at 2800 baud back in those days or whatnot. I mean, we built it for the for the moms in in the suburbs and who really what what they what they were when what we were. On it for them was that when they thought about planning a trip, this is how they do it and that and that they it wasn’t about this really cool technology. It was about they found the trip they wanted at the price they wanted. And the fact that this really cool technology was there was completely secondary. Now, obviously, it was core to what we were doing, but it was all about delivering that thing so people could have a really great trip.

Bronson: Yeah. Did your thesis turn out to be true that by putting the customer at the center, not technology, not other things, but really putting the customer at the center, that Expedia, that CAA, you know, have a lot of growth at that time.

Stuart: Yeah, I mean, it’s kind of ridiculous, actually. But you have to remember, this was also an interesting moment in time. There were a bunch of things going on. I mean, broadband was just coming. There was lots of pressures in the industry. The idea of e-commerce was really getting going. People were just getting comfortable with using their credit cards online. I mean, there were a lot of once only things that were happening at that time, but without a doubt, when there were people out there who were just like, Hallelujah, where have you been all my life? And and once you once they wanted to have somebody that, you know, somebody a brand, a thing that they could trust that was easy for them to use. That could be their go to and really sort of said, we believe in you. And everything that we did and everything that we built was really centered on this idea that we believe in you. You, you know, we the copy of the first the first ad that we that we ever ran, which was in a a color ad in a newspaper. By the way, back in those days, the copy was something along the lines of Who do you think would be better at planning your next trip? Someone who doesn’t know you at all or you who knows you quite well. We’re betting on you. Right. So it’s very much about empowerment and and and get it out of the way and and like it was you you could have said, hey, you know what? We’re going to let you do this on your own. And good luck with that. But like, there’s there’s no there’s no heart there. And it doesn’t it doesn’t put the people forward. And it’s funny, as I’ve gone on in the work that I’ve done with lots of different companies and lots of different founders and lots of different folks, that core issue for that core start point of who are you for and what’s the problem you’re trying to solve, putting that first and then building that and having everything centered around that. I swear that’s the difference between success and and a heck of a time ever getting to success.

Bronson: Yeah, and that sounds almost obvious. Why is it overlooked so often? I mean, why do people come to consultants like you for them to tell them the most obvious thing ever, which is know the problem, know the customer, and make it about them. Well, why is it missed, I mean, in your opinion?

Stuart: So so first off, with a lot of great companies, it’s not best and that’s kind of awesome. And even great companies run into challenges and even great even great leaders and founders and founding teams run into problems. But I would say that the biggest challenge is if you have a primarily technical group of folks who have amazing technical chops and perhaps have and just love the thing that they’ve built, they are they are less folk. First off, the idea of marketing and me marketing is profitably solving customer problems. I mean, that extreme marketing in business is very, very I mean, there is very little difference in my to my way of thinking. But for a lot of folks, the idea is that marketing is we’re going to issue a press release and we’re going to, you know, we’re going to SEO optimize our stuff or we’re going to look at our channels and blah, blah, blah, blah, blah, as opposed to it is really how all these things come together centered on being very focused and targeted on solving a specific problem. And I would say that for for companies and people for whom they have no background in this sort of stuff, technical background is a really common thing. Engineering background. It’s not that they don’t have sort of a broad appreciation that that of the of a user but it’s typically they’ve built some they’ve spent a ton of time and they’ve built this thing and now they’re like, Who am I going to sell it to? And so that’s where that’s where a lot of people run into problems is that is that they’re invested in a product that they have created that maybe has sort of fallen out of something else. And now they’re trying to find a round hole to put that round peg in, as opposed to who are you for? What’s the problem you’re trying to solve? How are you going to make their lives better, and how are you going to demonstrate to these people at all points of the compass, both in both in terms of the product experience that the look and feel, the visual identity, all the messaging, all of it, everything about this, about it’s the way you priced it the way it is. How are you going to do this? How are you going to demonstrate to these folks that you actually get there? And what you’re trying to do is is is really your entire life’s work is centered on making this thing better for them. And and that’s that can be really hard for people who already have this thing. They’ve built it. Maybe they’ve got a patent on it. I mean, the number of times I’ve spoken with people who are like, I don’t care that you have a patent, that’s awesome, but a patent isn’t going to do anything for you if it’s not actually part of some. So some improvement you’re making for somebody where they’re going to be willing to pay you for something right now. So I think that that’s the that’s the biggest that’s the bigger issue. It’s not that there isn’t a broad belief that that that’s sort of doing things for users matters. But there isn’t as deep an understanding of starting with a problem, starting with an insight, and then building everything around solving that. They typically have come at this and they’ve got something already and now they’re trying to figure out how the heck to, you know, Jimmy so that it’s going to fit.

Bronson: Yeah. And I think the advice you just gave is so important because the barrier to entry to create these startups and is just so low right now that if I have an idea by lunch, I can have a prototype. And by, you know, tomorrow I’m going to try to market it so I can do that cycle over and over and over so quickly that it feels like I’m doing something important when really I’m just not learning that I need to start with the problem, start with the customer and not start with. It’s so easy to build it. Let’s just build it. Sometimes you got to step back one step from that.

Stuart: Yeah, it’s and I talked to a lot of people and and so first off, I mean, I’m an entrepreneur and I have I have deep love and affection for entrepreneurs and the sickness that is entrepreneurship sometimes. So but but the number of people that I talk to who can’t sort of everybody I talk to, I actually have this stuck over my shoulder here that’s there. But you know that a real business is profitable, sustainable and matters to customers. The number of people that I talk to for whom that’s actually not true of the thing that they’re doing is really, really high, which is a shame because they’re like, what you want to be doing is something that you can either you can see how you’re going to make money at it, you can see how you’re going to be able to keep going with it, and that the customer is at the core of the thing and you’re trying to make their lives better. I mean, if you do this right, I’m getting somebody to pay you something for. It is is that is the least of your worry. It’s because because it actually becomes this amazing, validating thing where it’s like, where have you been all my life? Thank you so much for doing this. Of course, I’m going to buy this from you because you get me and you’re solving this for me and you know, rather than, okay, let’s try this, let’s try this. Now, that’s not to say that testing and and and and and measurements and all that sort of stuff doesn’t matter. But I’m just talking about the core start point. If you don’t have something that is profitable, sustainable or you know, and you can see how it could be profitable if you’re waiting for some magic thing to happen that somehow money is going to fall from the sky. Maybe it will, you know, but gosh, maybe it won’t. So, so just answer those questions and then you know that you have a business and you don’t have like a feature or you don’t have something that, frankly, is going to be extraordinarily difficult to get traction with.

Bronson: Yeah, I need to hang that up over my shoulder, too. That’s great advice. So after Expedia dossier, you became the CMO of Expedia at large. So you went to Seattle, you became a CMO there. What did you learn from Expedia, that CAA that really informed your decisions as the CMO because you’re there at kind of a startup level, beginning something new, and then you find yourself overseeing the whole thing. In terms of marketing, what did you kind of roll into that?

Stuart: I’d say that it was the same sense of deep customer empathy. You know, it was that it was different because it because it was much bigger because you’re dealing in tens of millions of unique visitors in the run of the month. And and all the numbers are higher. But, you know, at the it’s it’s a it’s like you’re rowing the same boat. It’s just that that the you’ve got to row at the same way, whether it’s a little boat or it’s a big boat, it’s basically it’s still about who are you for, what’s the problem you’re trying to solve and how are you going to resonate in a way that is going to that that’s going to that’s going to make it more likely that people are going to really like what it is that you do. I mean, the the U.S. market is a very different market from the Canadian market. And so especially in the travel category. And so there was a bunch of stuff you had to do. You had to park much more competition in the U.S. You had to be very, very aware of that, that in Canada we were fortunate because over time, frankly, we just won the other folks. I mean, Travelocity sort of drifted. I mean, they’re still around, but they kind of drifted away. Orbitz never came. Like, it’s just a very different market, us much more competitive. And the stakes were much, much higher, but the principles were very much the same. It’s how do you find a way to to deliver something that is going to resonate and make a difference and, and really demonstrate value for the for the for the customer? I mean, it’s the that’s what I was saying before. For me, when you talk about marketing and you talk about business, the people that don’t get it that it’s the same thing or people that don’t know what marketing actually is. There are folks who think that marketing is a press release and some and some SEO buys marketing, as I say, as profitably solving customer problems. They have to know who you are. They have to like you, they have to trust you. And then when all that said and done, then they’re ready to buy. And so it’s constantly working. That funnel, they come out the bottom here in the trust, bring them back down, return the trust, bring them back down. Make sure that they know that you’re there. I mean, but but it was it was a it was a it was a it was a big, challenging time for sure in in the online travel category. But in many ways, it was also the heyday of the online travel category because the big sort of third party guys, it was just booming at that stage.

Bronson: Yeah, I love that funnel you just gave us. I want you to walk us through that a little bit, okay. Because you’re in the CMO is Expedia. You’re having to deal with competition in America, like you said. And you have to find a way to help them know who you are to trust you and eventually buy from you and then start the whole process over. How did you do that? How did you get them to initially know who you are and then how would you walk them through that funnel in any any actionable tactics would be awesome. You could give us because there’s so many people watching this that they have to recreate that funnel and do that. And that’s the hard part.

Stuart: Yeah. And it’s, it’s not easy. And I mean, I was lucky because I also had $300 million to spend. But, you know, I had $300 million to spend at a time when paid search was just getting started. Right. So, I mean, it was a very different time from a communications perspective. We also had incredible, incredibly talented engineers and and and people on the inventory side. I mean, it was a it was a it still is an amazing organization. And the reason that they’ve been so successful is because of how all that stuff comes together. But essentially, any business, be it a B2C business or a B2B business, there’s a whole and you’re running that funnel all the time. And at the very top of that funnel, that’s consideration, right? That is where people are. If people are thinking about a certain thing that you’re one of the things that they think about. And so that very early stage consideration, that’s incredibly important because I can guarantee that if people don’t know you, they’re not going to find you. And if they don’t find you, they’re not going to trust you. And if they don’t trust you, they’re not going to buy from you. So, you know, you can you can try and compress that. But at some point, people have to know who you are. And so there’s lots of things you do up at that consideration stage. That’s the that’s the land of PR and sponsorships and and paid media of sort of all types. That is sort of the marketing communication level. That’s the social level that is, that is sort of getting, getting yourself out there. And then, yeah, and then with all the different sort of paid things that are, that are, that are part of that as well. But I mean that’s like building up your email list and partnering with others to go on their email list. That’s basically that’s starting to build that level of awareness so that people know that you exist, know what you do, and typically they would be the what you want. There is that if somebody were to say to you, give me the name of an X, that you’re one of them, right? And so that is what you want to do. So that at least sort of gets you in the game, then you start to work down. There’s multiple points where you get older, where you sort of remind people so that when they come, they try to kick your tires. You know, in the early days of Expedia, you couldn’t run a flight search without joining the site. Like, it’s sort of crazy to think about it now. And it’d be like somebody walking up to the door of a Kmart and it’s like, No, you can’t come in here to shop unless unless you give me all this information. So, you know, how do you how do you promote trial? How do you get people to experience what you’re about? How do you get them to sort of kick the tires and understand and come to know you a little bit better? So they’ve learned a bit about you. They’ve done something to actually show up at your site, by the way. All this stuff translates to any other situation that you want to talk about. They show that they now learn more about you. There’s another. No, it does does that. What they’re learning about you when they’re on your site and when they’re trying to use your product or whatever, be it, you know, in in modern, more sort of current day stuff, if it’s a web app or it’s some kind of whatever it is, is, is the thing that they’re now experiencing. Does that line up with what you’ve told them at the at the top? Right. So so all the way down. You’re just sort of that. Yeah. That’s again, that’s what they said they were. Yeah. It turns out that is what they are. That’s what these other people said they are now. They’re still doing it. Yeah. They’re not bad. And then when they and then when the time comes for that person to actually pull the trigger, you’re well-established, you’ve built some degree of trust. And then when it comes down to actually closing that deal, you want to be one of the ones that they’re that they’re using. Where, you know, you want is when you’ve gone from from consideration and work your way down and you now have what’s called preference, right? Which is they’re my guys or they’re my gals. That’s where I go. That’s where I do this stuff. There’s none of this sort of hunting and pecking and searching or whatnot. You just go there because because they’re the folks that I trust. They’re the folks that I go to when it comes to this stuff. And and whether it’s going to your barber because you think you’re barbers awesome or it’s going to an online service provider of some description because. Because you think they’re awesome. They’re, they’re qualities and characteristics and the way they are and the way they price and all that stuff. It all works for you. It’s it’s all the same thing. And it comes over time and then, you know, then once you’ve got that, once you’ve got that deal, once you’ve closed that deal the first time, then what do you do to sort of keep earning that trust? How do you stay in touch? How do you continue to demonstrate value? How do you remind them that you’re still there? Had you continue to show that you’re trying to make their lives better and, you know, and that gets different depending on the frequency of the purchase. Depending on the nature of the of the service or the product that you’re selling. But the principle is all basically the same. You’ve got to know people have to know that this thing exists, know that you’re one of those things come to come to like you, come to trust you, and then you’ve got a shot at getting the buy.

Bronson: Yeah. Thank you so much for walking us through that funnel. That’s really insightful as the CMO there. You know, you did so much right over your tenure there. What do you think was maybe the single best move you made as CMO? Maybe it was a partnership, maybe it was a tactic. Maybe it was something you did for the customers at the, you know, the user experience, the site, what’s maybe the one thing you point to and hang your hat on and say, I’m glad I did that.

Stuart: I would say that the big well, there were there were a bunch of things and it was a busy, busy time. Paid search was just starting. I mean, think about that, you know, so there was there were a lot of there were a lot of things that were just emerging. But I think that the single biggest thing that we did was start to think about start to think about what the inventory that we were selling as bundles as opposed to discrete items. And so now, you know, when you think about an online travel service, you think about bundles, you think about buying a hotel and car together, buy your flight and hotel together. You know that you’re going to save money, you know, so so that this idea of thinking about the entire trek and trying to get as much wallet share. So at any given trip there’s going to be for any given trip, they’re going to spend so much money and that money is going to be spent on a bunch of different things. And you want to get as much of that as you possibly can. You want to be of service to the extent that you can. So how do you how do you make it easy for them to pull different things together and frankly, work with suppliers in a way that means that they’re able to get some kind of preference and you’re able to get preferential pricing that you can pass on to your to your customer, but then make it easy for them to buy more than one thing at the same time. And we also started in we started adding in more services, like you’re going to New York. Well, do you want to buy tickets to a Broadway show? Do you want to buy hop on for. Hop off this. You want to buy travel insurance? So? So basically thinking more holistically and getting everybody to think more holistically and frankly, building incredibly difficult code to support all these different permutations and combinations and present elegant options to customers. Because, you know, the travel business is a is a very demanding category. It’s in many ways it’s a fairly tight margin category, although there’s certainly variability there. And and Expedia and the other online travel agency types have been a big part of creating some of that variability. But the but but the idea of sort of we’re better together and we’re going to really deliver something that is easy and, and and install more stuff around that entire trip. That was certainly a big thing. The other thing, frankly, was that with the emergence of paid search, just really getting sharp around, around at work optimization and really sort of tracking what was happening and starting to apply smart metrics around those sorts of things. The third thing really was, you know, I had my doubts that banner and buttons worked at all. And and there was a big part of me that just wanted to turf out, say, we’re not going to do those anymore. But really coming to realize through data that banners and buttons serve an important role as a reminder mechanism. It’s sort of like the the billboards of the of the interwebs that remind people that you’re that you’re there. So, you know, I would say that I would say that those are the things. But like the the the reality is television was really, really important to us. And if you’re in a big consumer category, even in this day and age and you’ve got the budget and you’re not thinking about television, even now, you’re you’re crazy.

Bronson: Yeah. Now, that’s good insight. Tell me a little bit about bundling, because I know you were actually the lead of kind of products and bundling those things there as well. Do you think that that’s a strategy that other startups watching this could utilize? We know now in 2013 that bundling works for travel. Now that’s a known thing, right? But we still may not know that it works for other start ups. Can you know, other kinds of industries, other kinds of verticals, should they be thinking about bundling? Do you think it’s something that’s under-utilized or are they wise to ignore in a lot of categories?

Stuart: So the trade, it’s a tradeoff between where you are in your stage of business and and the complexity of what it is you’re trying to do. So if it’s really early, then I would say focus, focus, focus. What’s the one thing that you can do and do it really well? And when and you’ll know you do it really well. When somebody who looks exactly like the type of person that you’ve designed this for shows up and says, Hurray, perfect. Thank you. Okay, that’s the result that you want. Now, if you’re able to bring in a bit more complexity, the ability to add to sort of have to have bundles, upsell, cross-sell, be able to sort of do more stuff within the your service offer can really work because options really work. Right. So, so rather than take it or leave it, it’s like door number one, door number to door number three with different inclusions, these sorts of things. And there’s lots of ways that you can build those sort of options that aren’t just around, that aren’t just around sort of functionality. It can be there can be lots of ways to build these sort of points of difference, but that lets you try different pricing models, that lets you try sort of tweaking things with AB tests. These people see this bundle, these people see that bundle. So I mean, I’m all about learning and I think that’s sort of what’s included in that offer. What’s included in that mix is, is one great way to be able to sort of test results. The but but I would say if you’re a very early stage company and you’re really just getting going, take the time that you could spend to try and develop code to do bundles well and spend that time understanding your customer better and being and being clearer and making sure that all the way up and down that funnel, everything you’re doing is designed for them that’s going to pay off for you much more than taking that kind of development bandwidth and putting it against some other product thing. Now that’s also going to be really hard because for more technical leaders and more technical founders, they’re going to go to the product thing because that’s what they know. Mm hmm.

Bronson: Now, that makes sense. You just mentioned how with the with giving them options, with giving them bundles, that you can bundle things and give them options, not based around functionality alone. Explain what you mean by that, because I’m used to seeing the three columns package, ABC, and they’re all about functionality. Every bullet point in every column is some feature, some thing that I can do that I can’t do with option A or B. So. What’s a non functional thing that you can kind of bundle?

Stuart: Access to training. Access to a higher level of of of customer service. A some some personal connection of some of some nature. There are there are lots of things that you can do. I mean, it’s different because where it depends really sort of what the product or the service is. But there are lots of things that you can do that are not just about rings, ring fencing features, but are about but are about changing the experience in some way. You can vary it by by duration, you know, X amount of time versus Y amount of time. You can vary it by like lots of different things. Access points. Like there’s, there’s, there’s so there are so many things that if you that if you start to think about. That are that are elements of value and what it is that you do that aren’t just about what’s baked into the code. And again the that so for for for more technical founders and like and trust me, I have, as I say, much love. Right? I couldn’t call my way out of a paper bag. So like I have I’ve got nothing but love and respect for for that. You can’t do it without that. But for more technical founders and founding teams, the what I challenge them to do is find somebody who has who is as much of a sort of business ninja, business marketing ninja, who gets that stuff as strongly as they do around the code side and see what you can do to bring those two things together. Because I guarantee that there are multiple ways that you can that you can frame any sort of service offering or any type of product. You know, why is why is a black something $10 more than a white something? Mm hmm. Because they’ve decided it would be right.

Bronson: Yeah. Thanks for clarifying that for us. That’s great. Now, after Expedia, you became the CMO of FreshBooks. And FreshBooks is kind of famous for their their culture. They have a good brand in the industry. People respect them. Tell me, what did you learn from their culture and their philosophy, their way of doing things while you served as a CMO there?

Stuart: FreshBooks is is amazing. And one of the things that’s most amazing there is the when we talk about sort of understanding of the customer, that customer empathy and really sort of being able to stand in their shoes, these guys do that like nobody’s business. There is no there is no doubt among anybody there from from the Deb side through to the service and through to the marketing team, through to the finance team, you name it. There is nobody there who doesn’t really understand who they’re for and what the problem is they’re trying to solve. You know, if I was going to say, what’s the what’s the culture? Well, you know, you can there’s there’s sort of lots of neat things around around sort of visual identity in dogs in the office. And we’re having a great time and and and all that sort of stuff, which is really true. But I think that if you sort of distill it down, it’s that really deep belief that that deep understanding of who it is they’re for, what they’re trying to solve, and everybody working towards that shared objective and that type of, you know, for me, that is that is culture, a culture. The rest of the stuff, the foosball tables and the dogs and the office and that and the beer on Fridays are awesome. And and trust me, I would I would not be I wouldn’t turn my back on any of that stuff. But at the end of the day, it’s it’s really about it’s really about this this this sense of of actually caring and and demonstrating that at all points, both in terms of how, you know, how elegantly the the the the the thing is designed through to the level of attention and and enthusiasm of the support crew, through to, you know, just just this the the clear way in which the code is being built that is really sort of trying to go to be simple for an audience that really needs the really need simple and really needs help. So, you know, for me, that’s the that that’s that’s the that’s the secret sauce there.

Bronson: Yeah, that’s great. Now, one of your biggest obstacles there, I’m assuming being the CMO of FreshBooks is really getting the conversion rates up. You have a lot of free users. You’re trying to get them over into the paying plans. And now I know you can’t give us the details of how you did that. We actually had Mike McDermott himself on, and he wouldn’t even tell me either all the secret pieces of what they did there. So I don’t expect you to but talk at a higher level because there are so many people watching this that have a freemium model. They’re trying to get users over to the paid stuff. And what are some of the high level strategies? What are some of the the mindsets, the things they need to be thinking about to make that happen in their startup?

Stuart: So I’m going to go. So I’m going to go back to. So, yes, right there. The secret sauce will stay stashed squarely over here. But, you know, when when I came in, the business, the FreshBooks business was exclusively a freemium model. There was no point at which people were asked for their business. So we started by opening tests that ultimately moved to a move to a trial model. So, you know, people can still use FreshBooks forever for free as long as they’re, you know, very, very small. But everybody who comes in starts on a trial. They, you know, they have full use of the product. They can they can do all the things that they want to do. And then at the end of it, it’s like, okay, so what do you think? Because, you know, the. There’s a there’s sort of a belief, I think, especially, again, among people for whom technology maybe is their strength as opposed to the business side, that sales is just really kind of an icky thing. Right? So but here’s the magic of sales. When you ask somebody for the business, they have to make a decision. And just by asking them for the business, a higher percentage of them are going to say yes than if you never ask for the business. So, you know, as basic as it is for for two to sort of think about, ask for the business, it’s like, hey, so you’ve tried this thing. What do you think? Would you like to buy it now? Like, it’s it’s it sounds really it sounds really sort of simple. And I have to tell you that we you know, we were very cautious and we tested our way to it. But but, you know, that was that was a that was a core change that resulted in a in in in a in a significant change in the in the frequency whereby people actually bought the stuff just because you asked them if they’d like to buy the stuff. Yeah. And, and so the message there is don’t be shy to ask for the business. There’s, you don’t need to let people use it for free, you know, just because just because you’re, you know, maybe you’re early in your career, you’re a recent college grad, whatever, you don’t have any money. And so you’re going to try and do everything for free. Here’s the thing. There’s lots of people out there that are more than happy to pay. If you ask them for it and they can see that you’re actually doing something that matters to them. So don’t be afraid to ask for the business. The second thing is, remember that. Remember that funnel of, you know, who are you? I know you. I like you. I trust you. I buy from you. So don’t expect that somebody is going to come to your web app having never heard of you before. But they happen to click on some link somewhere, arrive on your page, say Eureka and buy from you instantly. Yeah. So you should expect that that’s not going to happen. You should expect that that more than 90% of people are just going to go away because you’re you’re expecting people to go from I’ve never heard of you to I’m going to buy from you in one fell swoop. And some of them will invite more of those people and love those people and get as many of them as IBM as you can. But remember that that that their what else are you giving them to do so that they can learn about you? So that they can so that they can come to know you more so that when the time is right for them, then you’re in that consideration set. You’ve already earned some trust. You’ve got some familiarity. When it comes time for them to buy, then you know, you’re you’re in the game a lot of a lot of of early stage companies, especially in in in the digital space. You know, they’re trying to go from by meeting you at a bar for a drink to I’m going to take you home tonight, which, you know, once in a while that does happen. But typically it doesn’t result in a marriage of any meaningful significance. So how do we how do we ease people through? And how do we how do we get them to come to know us? How do we nurture those relationships and how do we demonstrate value along the way so that when people really do get a better sense of who we are, they’re more ready to buy from us when the time is right for them.

Bronson: Yeah, you know, you’re the second person on the show, to use the analogy of dating and marriage, to talk about the process, the long term process of courting a user and making it a great experience all the way along to have a sustainable marriage. So I think there might be something they’re hearing in a couple times now. Yeah. So you were.

Stuart: And we talk about we talk about lead nurturing. I mean, that’s sort of a hip and trendy topic about lead nurturing and nurturing relationships and content marketing. We’re going to do this. We’re going to do that. It’s about building some kind of degree of of understanding on the part of the prospective buyer of who you are, what you’re about, and then sort of thinking, yeah, you know what? These folks are kind of for me, I can see this, right? And so, yeah, there’s lots of names that go around this, but essentially it’s about it’s about building that relationship.

Bronson: Yeah, that’s great. Now, as if all this wasn’t enough, you’re also the co-founder of the mesh conference that I mentioned earlier. So tell us real quick, what is the mesh conference mesh?

Stuart: We’ve been doing this for going on eight years now. And it’s a it’s a it’s a it’s an event that happens every spring in Toronto, Canada. And it’s really it’s it’s really become Canada’s digital conference. So it’s about the impact that the digital world is having on how we live and work. And so it can be what’s happening, what it means for society, what it means for business, what it means for startups, what it means for media. And it’s changed a lot over the years, but we bring some really smart thinkers and we spend a couple of days going deep on some cool topics and and it’s just a whole lot of fun. And it’s I do it with. I do with. Partners. And as I say, we’ve been we’ve been there for going on eight years now. And it’s a it’s a labor of love. And it is actually happening in in mid-May. So May 15th and 16th in Toronto, Canada.

Bronson: Yeah. You know, as I was looking at the speaker list coming up and it kind of talks from the previous years and the ones we’re thinking about having this year, it seems like it’s almost like a TEDx for entrepreneurship. That’s the vibe I got like you guys on the bleeding edge, but it’s very similar technology, entrepreneurship. Is that a fair comparison? If people try to figure out what mesh is.

Stuart: I’d say that’s a big part of it. I mean, it’s sort of I call it like the thinking person’s tech conference because it is it does have that sort of make you think element that Ted has. But we definitely do go deep on entrepreneurship. We’ve we’ve talked a lot about venture capital. We’ve talked a lot about you know, we’ve we’ve done we’ve done sort of town hall type things with folks that are different stages of developing their business. And we’re just we all just sort of sit in a room and we and we talk about stuff. And and so without a doubt, there’s a there’s a strong element there that is about the early stage business with very strong support for for technology businesses. And and that’s but I mean, it comes from a natural place because if you start to look at the folks that have been behind this, we all in some way, shape or form or have been in this world. And one of the things that we saw is that there weren’t a lot of there weren’t a lot of venues where you could have these sorts of conversations and get fairly cool people together who’s sort of been there, done that, and and really and really spend time together. The other great thing about it is that is the people meeting each other. You know, it’s not just about I talk and you listen, but there’s been some really cool connections that have been made at this thing over the year that over the years have resulted in in different businesses starting up, that that have resulted in all sorts of interesting things happening. So, you know, it’s a I think TEDx for entrepreneurs is a huge element. But there’s also this idea of what does all this mean? You know, and and and so we said, are you guaranteed, Ted, guaranteed to come away with a bit of a mind expansion happen?

Bronson: Yeah. Now, seeing how mesh is sort of on the forefront of all these trends and how you yourself have been on the forefront of trends, you know, you disrupted the travel industry in Canada. What industry is or what verticals do you think are next in line? Who has their head on the chopping block to be disrupted? So the people watching this can kind of, you know, be a few steps ahead of competition. So they know kind of ahead of time, like, okay, that thing’s going to change. Let me be a part of changing it.

Stuart: I’ll tell you, I. I went for a long, long, long time, like sort of ten years of, you know, mobile is the next big thing. And then another year ago it’s like, okay, so where the heck is mobile? Where the heck is mobile? Where the heck is mobile? Okay, I’ll tell you right now. Mobile is not just the next big thing. Mobile is here. Mobile is huge. And anything that. So, you know, if you want, you want sort of you want sorry. You want broad trends. You want something that’s really sort of prime for disruption. I think it’s anything where you can take a mobile first approach and have a user experience that is simple and elegant and lets them do something that they want to do wherever it is that they happen to be. And and, you know, that’s a that’s a broad bucket. I know. But they’re, you know, designing for desktop first. I say that’s not the thing anymore. Design for mobile first. Fine, you know, and b, b, be mobile centric, be constrained and what it is you’re doing and really crystallize your concept. And B because if you can crystallize a concept and have it come through in a mobile device in a way that when that customer has actually shown up, they get who you are, they get what you’re doing, and they see how it can benefit for you. You’re going to be awesome on the desktop, don’t worry about it. But it’s so I would say it is you know, it is absolutely mobile’s time to shine and whether it’s and whether it’s iOS Android or you know frankly I’m I’m still waving the BlackBerry flag or be it being a Canadian true Canadian. Yeah I I’m a no matter no matter what the device is, no matter what the form factor is responsive and and constrained. Mobile first is, is the way to go. And and so we look for things where the true power of the device can make a huge difference. You know how I’ll give a shout out to some some some friends of mine in a category that I’m very familiar with, you know, the guys are hoteltonight, for instance. So hotel space is a is an amazing application mobile first. I still don’t even know that they have a desktop version, but what do they do? They bring the look, they bring the locality which they can get through the device to this last minute thing that’s happening today and deliver it to someone in an elegant way for something that they really could use where there’s benefit for the seller, the hotel is being open to a market that they otherwise might not see the user because they’re getting this curated list. They’re seeing it at the at the to buy on the device in the place where they need it at the time that they need it. And it’s easy to use. So, you know, you want you want a broad sort of example of what the integration of taking mobile to to it’s sort of logical execution looks like look for those sorts of things it’s it’s not just a computer screen that happens to be in your hand. There are all sorts of other elements associated with this thing. How do you use all of that in a way that that that again, you get that result. This like, this is awesome. Where have you been all my life?

Bronson: Yeah. No, that’s great. Thank you for sharing those examples with us. So help me understand what you’re currently involved in, because on your LinkedIn profile, it says that you are in business strategy, design and leadership on demand. What does that actually mean? What do you do?

Stuart: I help I help businesses figure a bunch of this stuff out. Yeah, that’s what I do.

Bronson: So you do consulting, they come to you?

Stuart: Yeah.

Bronson: Yeah. So how does that work? Do you take a percentage of companies? Do you get involved at a deep level? Are they just paying you an hourly fee? Like how does that arrangement look like? Because people might hear this interview and say, All right, I need to get in touch with Stuart.

Stuart: It’s soup to nuts. I it can be it can be a an occasional phone consult with somebody who’s got a specific problem. I’ve done I’ve done work with with early stage businesses from South Africa to Australia and everywhere in between UK, US, Canada, you name it, Mexico. And and sometimes it’s, sometimes it’s very simple. They have they typically have had some kind of come to Jesus moment. And what I mean by that is something is not working anymore. They’ve been at it for ten years and they’ve hit some kind of plateau and there and they don’t know where to go or it’s a partnership. And some, you know, the dynamics between the team has changed and the phone is ringing is is as easily as it used to. They’ve had or, you know, they for some reason, some things just not working. And so depending it can be. I need some advice about this specific thing. Okay. I will give you advice about this specific thing through to I’m going to come and be with you a couple of days a month and we are going to you know, I’m going to roll up my st my sleeves and I’m going to like embed myself in your business and we are going to work on this stuff together. Typically it would be with a founding team or with. An owner. And, you know, sometimes it’s it’s sort of I’m introduced by investors who recognize that that maybe it’s a situation that needs a little bit of help. You know, I’ve got whatever I have left is getting gray on the sides. There’s a lot of the stuff that I you know, I have I’ve I’ve seen it, I’ve lived it, I’ve done it. And so for me, my great love is being able to take this tool kit that I’ve established over the years and and put it to use for other people who recognize that they’ve hit something and something’s got to change. And so I’m kind of the growth guy and the unblocked guy and you know, that the engagements can be to sort of figure stuff out. Here’s the template, go into it. But through two, I’m we’re going to do all that and I’m going to help you do it.

Bronson: Yeah. Well, Stuart, this has been an amazing interview. I have one last question for you. I think I might know how you’re going to answer it, but I’m going to ask it anyway. What’s the best advice that you can give to anyone that’s trying to grow their startup?

Stuart: And what do you think is going to be?

Bronson: Focus on the customer.

Stuart: Without a doubt. The best advice is focus on the customer. Don’t fall in love with your product. Fall in love with your user. Remember that your job is to make their life better and that if you’re doing that, money will follow. Money is the byproduct of being awesome, and when you’re being awesome, your customers know you’re awesome and they pay you for it.

Bronson: I want to get that quote on a T-shirt. Money is the byproduct of being awesome. That is the start of, quote, the best one of the show so far. So thank you for that, Stuart. Thank you so much for taking time out your busy schedule and coming on the show and really educating our audience.

Stuart: My pleasure.

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