Shortly after we invested in Jake Tyler and Natalie Cartwright’s startup Payso, we interviewed the co-founders to learn more about where the business idea came from, how they met, challenges they’ve faced, and the mentors and people who support them.
Q&A With Jake Tyler & Natalie Cartwright
Where did the idea come from?
Jake: I lived in London for a long time and did a lot of trips with my friends. When you live in London you always want to leave to somewhere sunnier, so I organized a lot of trips and would rent a house for a lot of people — for 18 people in Spain, for example. I’d have to pay it all myself and ask everyone for money back, which was always a painful process.
Eventually I moved to Spain to do an MBA, and we had a similar problem where people were always out socializing and splitting bills, which was always a messy pain in the backside.
I was also coming out of London at a time when Fintech was really starting to heat up. So I started by MBA thinking about this problem. Then, of course, I came up with all sorts of wildly complicated solutions which were all terrible. I spent 12 months working through these before I cut it down to the simplest possible solution, which is what you see now with Payso.
IE Business School has a startup incubator program that Nat and I were both part of, working on separate projects at the time. We both shared the ‘best startup’ prize in our MBA class and Nat was clearly a super-star so post-graduation I did my best to poach her. Our team was myself and our CTO Guru — real name — and we were looking at where the best market would be to launch Payso. Nat, I think jokingly at first, said she’d jump on board if we came to Canada. I’m very much of the school that awesome people can make anything happen and Nat is awesome people, so we packed our bags and headed over.
Nat: I didn’t expect that he would move to Canada. At the time I was like, “Let’s move to Canada!” And being a crazy Australian he said, “Sure!”
Jake: That all happened outrageously quickly. About a week later I was on a plane to Canada. That was on the first of November. I arrived with one suitcase, one bike bag, and one snowboard, minus one suit that I lost on the plane.
How did the business evolve after IE?
Jake: Payso was the simplest possible solution to the problem of splitting a bill, be it sharing expenses with flat-mates, or dividing up the tab at dinner. Getting to that – cutting everything out – took me a lot of time and a lot of iterations. Other people in the market have more complicated versions, like Tilt, and there were different versions of that in Europe.
Nat: We launched in beta on December 15, but even last night we were talking about, “What can we take out?” It’s like the writing process: simplifying it as much as possible to get the best out.
You want to create something like Snapchat or Instagram in terms of simplicity. We want it to be a social app with payments in the background. It should be delightful. It should be social. You’re sharing a moment. We see ourselves more as the Instagram of payments than a better version of your banking app. If people had asked, “How do I use a digital photograph?” when they were converting from analogue to digital, no one would have said, “I Snapchat a photo of my coffee and put a filter on it.” You’ll see the same change with sharing money and how people do it.
Jake: I also hate lining up for the ATM.
Nat: And cheques should have been taken care of a long time ago. Three years from now, wherever you want to share money is where you’ll be sharing money. You won’t be forced to share it in a banking app or bricks and mortar – you’ll be sharing it over Twitter or Facebook, or wherever you want to share it.
How is Payso different from emailing money from your regular bank account?
- It provides a great experience, is fun to do, and you’re sharing your money in the background.
- You can share within groups.
- We send automatic reminders over two week periods.
- You can see who’s paid and who hasn’t.
- You can send up to $130 like a text – we replace cash for small transactions. We can actually do up to $500 per transaction, but over $130 you have to do 3D Secure, so it’s a bit more painful.
- You don’t need to top up your Payso account before you start.
- Money can sit in your Payso Wallet, or you can cash it out right away.
- It doesn’t take three days to load up your Payso Wallet, which is what it takes with PayPal. You’re ready to roll right away.
Any advice for selecting (and working with) a co-founder?
Nat: It was a bit of luck and serendipity for us. We were in separate classes in the MBA program so it wasn’t til later in the MBA when our accelerator teams were working together that we became friends. Jake was one of the most impressive people in the program. I told him, “Jake of anyone in the class, you’re my horse.” I honestly wasn’t sure if I’d ever see him again – he was an Australian and I was a Canadian – but I knew he was going to do great things.
I was looking for an opportunity here and nothing was fitting. Jake’s previous co-founder had found a full-time job. We were both looking for someone and we both respected each other, and Jake was crazy enough to move to Canada.
Jake: We aren’t dating, by the way. We do spend an outrageous amount of time together. We basically don’t have any other friends.
Nat: No, we don’t have any other friends.
Jake: We live in the same house with Nat’s parents.
Nat: We basically live in our bubble of Payso. We try to talk about Payso with everyone… and we try not to talk to Payso with each other.
Jake: You have to work with people who are awesome and who you can get along with really well. If not, you might as well not do it. I’ll move to Canada to work with people who are going to be awesome.
Nat: One day we have a senior VP from a bank calling to offer us a really interesting deal, and the next day we’re not sure if Jake is going to get kicked out of the country. At the end of the day, you need a sense of humour and need to be able to roll with it and occasionally go for a drink and laugh things off.
My previous job was working with the UN. I learned that if no one is going to die, then it’s light enough that you get the work done, and make the best of it. It’s all going to be OK.
Have you had any mentors?
Jake: Nat’s brother Jon Cartwright, and also Zolo.ca.
Nat: From day 1, the Zolo team said, “Come sit in our office.” It’s a baller team. Ryley Best, Jason Billingsley, Barry Allen, and my brother Jon is now working with them. For a few months we were squatting in their office, and they gave us advice, were super helpful, gave us introductions… they’re great with honesty in a helpful, constructive way. They’ve provided us with an incredible amout of support.
Jake: Jon has been amazing. Not just because he’s Nat’s brother, but also everyone else – people in the ecosystem here – really want to see teams be successful. We’ve had an outrageous amount of support from the local ecosystem. We haven’t met anyone who didn’t want to meet for coffee or make an introduction. I think that’s the first generation of successful entrepreneurs really investing in the pay-it-forward culture.
Nat: I don’t know how we would do it without that. We have the co-founding team and about 100 people who are routing for us.
Jake: Startups are a lot about trust, but your investors need to know people who know who you are, so you need to network in… and the only way to do that is to connect with new people, and go for coffees.
What excited you most about joining the HIGHLINE family?
Nat: HIGHLINE has an extremely good reputation. It was so exciting to be recognized as a team that was at a stage and of potential to be accepted into HIGHLINE. That was one of the highlights – we really hold on to the successes, and that was a great validation for us. And all of the support that comes along with it: sitting here and telling our story, and getting support with media, and having a team behind you that’s really making sure you’re successful. And being able to leverage all the experience from the other founders.
Jake: Also, we’re not in cohorts. We can just start now, right when we’re ready, and HIGHLINE builds support around what our needs are, rather than squeezing us into a structured programme. And we love the specializations. If you look at some of the latest investments – Control, Koho, Payso – there are a lot of startups in the fintech space. HIGHLINE also gives us access to a Canadian and North American support network.
Nat: And the fact that HIGHLINE is building partnerships with the Canadian government for Startup Visa. We’re building an international business and HIGHLINE is the best accelerator program in Canada for thinking big.
What are you focused on now? What are you ambitions for 2015?
Nat: We want 25% of 18-35 year-olds unable to live without our app. We would love to provide a better user experience for sharing cash – a free way for sharing cash.
Jake: We want to turn sharing cash into a social app. And by the end of this year we want to have won a large part of the market in Canada. One of our potential investors described us as a moonshot.
Nat: That’s perfect. That’s it. If we do this, it’s going to be huge. It’s a risky business, and the only chance we have is to be incredibly aggressive, and that’s our approach.