Harrison Rose of Paddle

Founder Coffee episode 034

Christian Owens and Harrison Rose, Paddle co-founders.

I’m Jeroen from Salesflare and this is Founder Coffee.

Every three weeks I have coffee with a different founder. We discuss life, passions, learnings, … in an intimate talk, getting to know the person behind the company.

For this thirty-fourth episode, I talked to Harrison Rose, co-founder of Paddle, a leading subscription and commerce platform that helps SaaS businesses grow faster.

Harrison started Paddle with his co-founder when they were 17, going on 18, right when they were due to join university. They dropped out before it even began.

At first they built a marketplace for businesses, much like the App Store, but when it turned out nobody wanted another marketplace, they dropped the customer facing aspect and kept the platform for payments and the like.

We talk about how he builds a solid team while hiring 100 employees in a year, why he gets up at 6am, how he keeps his high energy up, and why you need to keep learning faster than your organization.

Welcome to Founder Coffee.

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Jeroen:

Hi Harrison, it’s great to have you on Founder Coffee.

Harrison:

Hey Jeroen. Thank you very much for having me.

Jeroen:

You are co-founder of Paddle. For those who don’t know yet, what do you guys do?

Harrison:

So Paddle is a platform for software businesses to run and grow their own business. So by ‘run’, we mean removing all of the operational burdens out of selling software, really letting these companies unlock their potential, selling where they want, how they want and to who they want. And the ‘grow’ piece of that mission is using all of the data that we gather on these software companies and how they’re performing, to try and deliver some kind of strategic insight as to how they could sell better, or go to market, and more.

Jeroen:

Right. So I’m trying to understand what you guys do. Can you be a bit more specific about some of the challenges you guys are addressing?

Harrison:

Sure. Yes. I mean selling software is hard, and gets increasingly hard, I think, as companies age. So people will set up a bunch of payment gateways to start with, and then they’ll plug them all into a subscription management platform. They might struggle then to handle fraud and implement tooling for that. And when suddenly, they get traction globally, they also have to handle taxes. They set up a bunch of bank accounts and entities to avoid foreign exchange charges, and to receive invoices and wire transfers in those currencies.

Things basically get complicated really, really fast.

We’re really trying to remove that complexity, allow software companies to integrate with a single platform that’s ready to scale with them. You want a new currency, turn it on. You want to accept a new payment method, tick a box. It’s better than people having to build out this internal infrastructure, and internal expertise. Does that make sense?

Jeroen:

Yeah. And how do you guys then compete with Stripe or Braintree? Are these services that integrate with Paddle?

Harrison:

No. So they take care of a very small part, I guess, of the buying process or the selling process for a software company. They are fantastic products individually. The types of infrastructure that Paddle will be built on top of, to some degree, makes it very easy to accept a credit card payment, for example. When in reality that’s just a small piece in actually selling software. But you do need to accept multiple currencies, offer additional payment methods, handle the tax, deliver the product to the customer and also have some reporting requirements.

They’re very good products that are a very small part of that journey, I guess, of the transaction.

Jeroen:

So, are your customers mostly the smaller SaaS companies or the bigger ones?

Harrison:

So we’re working with about 1,500 software companies who are placed all over the world. We’re working with people who are just getting started, all the way through up to people doing tens of millions of dollars annually in revenue.

So there’s a real broad spectrum there.

Our real sweet spot is software companies that have reached some scale. They’ve built out a lot of tools and internal jobs and expertise, and that’s starting to creak. And perhaps as they’re going through a change, as in their moving up the market or trying to internationalize for the first time, they’re having to update the infrastructure or build out a whole new set of tools and jobs internally. It’s often at that point they migrate to Paddle, to simplify what they were doing previously, but also enable their next stage in growth, without having to build out all the infrastructure again themselves.

Jeroen:

Right. How does someone start building a company like this one? Did you have a SaaS company before this?

Harrison:

Yeah, it’s a question we get asked a lot. So this is my first job, actually. We’ve been going for seven years now. I started this when I was 17, going on 18, with our CEO, Christian, and I met him actually whilst he was building software and selling it himself. He was trying to build and sell and some invoicing software.

We realized quite quickly that he was great at building the software and creating a great product. But actually selling it globally, because you think in selling software you can be global from day one, he realized that was actually really tough. And so we dabbled with some ideas as to how we can make that easier for these people building software.

We actually started with the idea of a marketplace, because marketplaces or places like the App Store do make it a little bit easier for software developers, taking off the burden around payments and customer support from people.

Long story short, it turns out people didn’t want another marketplace. We dropped the customer-facing element to that, which we built, and then just started to sell the infrastructure B2B. And now folks just use Paddle to actually sell their own products.

Jeroen:

That’s really cool. So, you started this straight out of school?

Harrison:

Pretty much, yeah. I was due to go to university, and the summer in which I was due to go, we raised money to do Paddle, and since then, we haven’t looked back. So seven years on, we’re now 140 employees, here in London. We’ve raised $25 million in funding, and got over 1500 customers all over the world. So it’s been quite the journey.

Jeroen:

Are you still planning to do university at some point? Like let’s say you sell Paddle at some point, would you go back to university, or would you continue building more products?

Harrison:

That’s an interesting question and one that I’ve been asked before, and I think I’ve answered it poorly. I’ll probably do so again. I think I love learning. I’m pretty obsessed with continuous improvement, both as a company in terms of our process and our people, but also myself. There’s a lot of me that wants to learn many different things.

I think if I was to go back to university, it would be to learn something entirely outside the scope of what I’ve been doing, I guess, for the last seven years. Like learning English literature or doing something that offers a fantastic experience. But it very much would be, I think some form of escapism, or just to try and do something new, as opposed to directly related to what I’m doing day-to-day, I think.

Jeroen:

I see. It’s also this yearning for learning that made you start a company at this early an age. When did you actually decide to start this all? When you were 17, right?

Harrison:

Yeah, we did it when we were 17, nearly 18.

Jeroen:

How did you decide to then start a company?

Harrison:

I guess it’s the belief in the pain that it is that you’re solving. We’re very fortunate to have been trying to solve this problem ourselves, Christian and I, as 17-year-olds, trying to sell our own software and so on and so forth. Realizing how difficult that was, speaking to lots and lots of other people building software, and hearing the pains that they’ve gone through, and then receiving backing before we were even trying to solve this problem full time, gave us a lot of confidence that there was a market for us, and people that wanted help.

I think it frustrates me even to this day that whether a software product could be more successful than another could be based on the internal infrastructure they built themselves to be able to enable the selling of that product, as opposed to the product quality. And we want to give every software company the opportunity to sell to whoever they want, however, they want, and really succeed based on the merit of their product rather than the internal infrastructure and expertise that they’ve built.

And we have that quite grande plan, or vision, I guess. We got to it pretty early to try and deliver that solution. Yeah, it’s been quite the ride.

Jeroen:

Definitely must have been. Is this your very first project then as well?

Harrison:

Yeah, pretty much. I am lucky enough to mentor a few folks. We have a very close portfolio from each of the investors who have done our various rounds. So talked to an awful lot of other founders. I think that’s one of the ways in which I stay sane, but this is certainly my first full-time and successful gig. Same as Christian. Our CEO.

Jeroen:

Yeah, but projects could be anything. Like you could have built out some kind of organization in school or built websites in your free time. Did you do any of these things, or this is just like you are in school now, all of a sudden you decide to build Paddle?

Harrison:

No, I had many, many projects at school, and got distracted many times. I’m sure many of the listeners did. Everything from trying my hand at some graphic design and logo design, which I’m sure I would wince at, or be terribly ashamed of if I looked back on it today; through to selling software bundles and flash deals and software. Yeah, we tried all sorts of stuff, but all of this really did build our understanding of, I guess, how difficult it is to succeed as a software company, and how one of those big problems is actually getting your product out there, or getting money for it in the first place. Which funnily enough, is pretty important to these companies.

Jeroen:

So if I may ask, what kind of software companies are seeing the problem you’re addressing?

Harrison:

This is interesting. I think even our own understanding of the scale of the problem that we’re solving has really evolved over time. In our early days, we felt the infrastructure we were building out would maybe just be appropriate for smaller companies, who didn’t have the internal resources to build a team that handles tax globally, for example.

And it was our belief that at some point it made sense to do those things in-house, when, in reality as we’ve grown and got larger and larger customers over the last seven years, no matter how big your software company is, development time and hiring people, or building the skills and expertise internally, are often some of the blockers to what it is that you’re trying to be.

We hired a hundred people in 2018, and that wasn’t something that I’d wish upon anyone. So no matter how big you are, resources are always tight, and you should be focusing on the highest impact things you possibly can make, which normally are the unique selling points for your particular product.

So I think over time realizing that massive companies still have this problem has inspired us, certainly. But yeah, I guess our own understanding of this has probably evolved over time, would be the short answer to your question.

Jeroen:

Is there anyone that particularly inspired you seven years ago, when you started Paddle? Or anyone that inspires you today, that you look up to and think, I want to be more like that person?

Harrison:

In terms of particular CEOs and folks that I look up to, there’s so many amazing people and pieces of advice out there. So to start with, I definitely wouldn’t limit this to CEOs, but also coaches, mentors, VCs, et cetera. And I think surrounding yourself with these people, particularly having not done this before, is an absolute requirement in order to have any degree of success, or even to stand a chance.

In the UK, I really admire Tom Blomfield at Monzo. He is doing some really amazing stuff, as a company, as a product, and even really forward-thinking stuff in terms of diversity and inclusion. Heroku and GoCardless have an amazing story too. I would encourage people to read about him if you haven’t already. Elsewhere, great friends with Patrick Campbell, ProfitWell, he’s an awesome human being, and absolutely mad. Great guy. And Mathilde at Front, some of the stuff that Point Nine has covered on her, and how she approaches work and internal process and discipline have been really, really inspiring as well.

Jeroen:

Who was the last person?

Harrison:

I think Mathilde at Front.

Jeroen:

Mathilde Collin? Yeah, I also listened to a podcast with her this week. It’s pretty interesting. The way she built a culture in Front, keeps delivering this great product, it’s all pretty cool.

Harrison:

The thing I like about her advice is that it feels really practical. So hearing about the types of emails and things she’s sending out, at the start of the week, at the end of the week, are just really useful, actionable things that you can implement to make an impact. I have heard some cool stuff from her.

Jeroen:

Me too. So what is it that you are actually working on right now, personally?

Harrison:

At Paddle, myself? My day to day feels like it changes every three weeks or so. I think founders probably have to embrace this. So we’ve been growing like crazy. We hired a hundred people last year. We’re the fastest-growing software company in the UK, and when you’re growing at that trajectory things break a lot, and I think that there needs to be an obsession with continuous improvement and efficiency to even make that possible.

So in terms of what I do, I tend to sit in a role as a chief customer officer. So looking at the experience of the people using our product end to end, working closely with our go-to-market teams. There’s a real emphasis on customer success and sales, but also product too, and being as close to the customer as possible. So at the moment, I’m tending to jump in alongside whichever relevant executive necessary, across those teams, on improving whatever there is that needs to be better or putting out the fire that exists in that team.

That’s very much going to change. So later this year I’ll be tasked with opening and launching our first international office over in the US, some time in Q4.

Jeroen:

Awesome! Are there any of these things that keep you up at night, particularly lately?

Harrison:

Yes. Lots of things, I guess. I think there’s always something you’re working on, right? I think there’s a real skill to try and shut off from that and relax a little bit. I think the big things that I’m thinking about the most when I put my head on the pillow and try and get some shuteye would be ‘how do I build out the right leadership team, that maintains our values, that will inspire our organization?’ Because they’re mistakes that you don’t want to make.

And, then finally, yeah, the logistics and the execution of rolling out that first international office, are going to give me lots of additional thoughts and things to do, I think.

Jeroen:

Yeah. What are some of the lessons you’ve already learned when working on that first topic, like building out that leadership team?

Harrison:

I think there’s a lot of things we could touch on. There’s when you go from being 30 to 130 very quickly, or even as you’re going through hyper-growth, there’s a temptation to just constantly promote people into managerial positions, just because they’ve been there for a long time. And I think an understanding and being able to identify who’s the right fit for management and who’s not, and actually giving people other pathways and progression, other than becoming managers, is quite important.

Often, you know you’ve made the right hire if the person that you do hire as a manager, who’s coming in above someone who’s perhaps been there longer, if that person you’re bringing in is truly exciting that individual, they’re very confident they can learn from that person and the whole organization’s excited about how much they’re going to drive the business forward. That’s when you know you’ve made the right hire. It’s a really good measure of success, I think.

And then equally, really trying to cut the balance between the person that you need right at that moment, and what that person is going to need to look like in 24 months or so, as well. Because you want that person to grow with the business, and you do need to be forward-looking there, and sometimes that’s really difficult.

Jeroen:

Where do you think you should ideally strike that balance?

Harrison:

Yeah, I think the 24-month mark is about right. Beyond that, you might not have someone who can get hands-on and deal with the areas for improvement that you have today. But you also want to have enough runway there that they have the chance to grow and develop, and they can also fix the problems of the future, which could look super, super different. I’m sure this is going to be very different from individual to individual.

Jeroen:

Right. What is the next thing that’s on your plate, that you’re looking to delegate?

Harrison:

Yeah, I’m trying to almost make myself as redundant as possible from the day-to-day operations at Paddle right now. I’m going to be heading out to the US and launching the office there. I expect to be back here a lot, and spend an awful lot of time on flights, where I’ll be feeling very sorry for myself, I’m sure. But really trying to remove myself from any day-to-day operation, to ensure that I don’t become a blocker, or time zones don’t become an issue for us.

Jeroen:

What is the last thing you now have to remove yourself from?

Harrison:

We recently hired a chief commercial officer, actually, to come in and take on some of the people who are still directly reporting to me. Some quite senior folks. So getting that person up to speed and onboarding him is the latest thing, but very excited about the impact it’s going to have. Very fortunate that the individual we’ve hired there has mentored me for two years and is now going to come in and really drive the entire business forward, and the entire business will get to benefit from some of the great advice I’ve received from that person.

Jeroen:

That’s cool.

Harrison:

Yeah, it really feels like a stamp of confidence and belief in what we’re doing, with that person being with us on that journey as well.

Jeroen:

Yeah, that’s very cool. Talking about cool, what is it exactly that gives you energy when doing this work? What do you feel drives you forward?

Harrison:

I have a lot of energy. I’m sure I’m already speaking way too fast than most of your listeners would prefer, which I apologize for, and I hope you’ve got a fantastic app that allows you to slow me down whilst you’re listening. Yeah, I’ve got tons of energy.

I think a really great piece of advice I’ve got, and now try to share as much as possible, is that do try and enjoy your work day-to-day. As much as it will always feel like there’s something that you need to fix, or something on fire, or whatever, I think the way to really make that energize you and term that positively is to be someone who enjoys identifying the area for improvement. You need to enjoy putting out that fire and then enjoy moving onto the next and continue leveling up yourself and your organization like that.

Unless you enjoy that process of constant improvement and iteration and the need to do so, it would be very easy to get down in the dumps about how things are breaking or how they’re not working. Instead, really try and flip that on its head. Celebrate the fact that you’ve spotted the thing that can get better, have a plan to fix it, and you’re going about doing so. Because if not, in these organizations which are growing so quickly and improving all the time, I imagine it can quite quickly get overwhelming, I guess.

Jeroen:

So you’re saying enjoy the fact that you’re working on it, enjoy the fact that you’re fixing it, enjoy the fact that you’ve seen what you need to fix?

Harrison:

Yeah, exactly. Exactly. Because there’s always going to be something.

Jeroen:

People are like, “Oh, it’s all broken.”

Harrison:

Yeah. Exactly. There are articles you read where everything seems completely breezy, and everything’s great. I imagine behind the curtain there are some people running around trying to fix some stuff for them too.

Jeroen:

Yeah, for sure. But that’s not super easy to do, right? To always keep believing that, because there’s seeing what to fix, and then there’s working on it. Then there is also keeping the belief that a certain thing you’ve been trying to fix for a long time is now going to get better.

Harrison:

Yeah. I think the real danger that you can fall into, beyond that becoming overwhelming, and a new feeling ‘down in the dumps’ that everything’s broken, is apathy. At any point, and I’m glad the organization snapped out of it quickly, a problem arises when people become very good at spotting the problems. Why? If you don’t follow them up with, “Great, what’s your plan for it? What are we doing about it?”, and encouraging and empowering people to contribute, it can be very dangerous. You just point out the areas for improvement without excitement about the plan to fix it, or the empowering of your people to actually solve that problem. That’s not good.

Jeroen:

Yeah, definitely. That’s some good advice. How do you keep this amount of energy? Is it sleeping a lot of drinking a ton of coffee?

Harrison:

I’m not sure. I’ve always been a bit mad, kind of. It’s no surprise to anyone in the organization if I’m running around, running back to my desk, singing at the top of my voice, walking around. I’m quite lucky that I think I’m quite naturally energetic, or positive, I think.

You’ve got to enjoy what you’re doing, right? And I really hope that manifests itself around the organization, and people can see all that, and it makes them look forward to coming to work each day as well. Although I’m not sure my singing would be making that many people happy, on reflection.

Jeroen:

So you sing well?

Harrison:

Absolutely not. I was chatting with a colleague just this weekend. We do a great thing for our staff, and that is giving everyone a learning and development budget. We use a fantastic SaaS product out there, called Sunlight in order to do that. And we let people spend that money on whatever they want.

So we’ve got one employee in sales who spends his budget on improv classes, and I went to go and see one of them, and he was awesome. He actually explained that it has really helped him in his day-to-day tasks, even at work. But the person I spoke to at the weekend said that he’s using his budget to get better at singing. And he said that the level he wanted to get to when speaking to his teacher was just that it was acceptable for others to hear it. I think I should probably be going off for some similar lessons, maybe.

Jeroen:

Yeah, you could join him. What is it actually that you do when you’re not working? Or do you only work?

Harrison:

Work/life balance is an interesting one. And I’ve heard a lot of people on the show talking about this. It’s great to hear lots of people’s perspectives on this. I’m a huge workaholic. I can take on big workloads, problems, work for long hours, without an impact on health or wellbeing, at least that I know about right now. But I think that’s truthful because it’s all I’ve ever known.

I’ve been working on Paddle and Paddle related problems since I was 17. I’m now 25. But I do know this doesn’t work for everyone. Each individual needs to work very hard to get that right balance for themselves. It is something I’ve got better at too, probably. In the early days, it wasn’t uncommon that I’d work every day and into the night, and then I stopped doing it on Saturdays as much as possible. And now I do much less on the weekends, but yeah, I work a lot but enjoy it, which is really important.

Jeroen:

Yeah. Well you’re still young, so you don’t have all the little things that older people get, but you’ll discover, I suppose.

Harrison:

Yes, I imagine so. I’m very grateful for the patience that people have around me – family, friends, girlfriends, attribute saintly. I think the number of times I’ve asked, “Can I just send a quick email before we head out?” to these people, and they’ve said, “Yes.” I am eternally grateful for them, but yeah. It gets increasingly difficult with family and kids and things, I’m sure.

Jeroen:

I was not just talking about that. I was talking about health issues.

Harrison:

Okay. Yeah, yeah.

Jeroen:

The older you get, it starts popping up left and right. Having to go to the physiotherapist, and the hospital, and all those kinds of things. Things you would never have imagined.

That’s when work/life balance becomes even more important. When you’re young, you can just keep going for as long as you want, but then at some point, you start hitting some limits.

Harrison:

Yeah. You’ve got to be true to yourself, right? You can’t do everything. And then I think we all need to be real with ourselves about how much actually can wait until tomorrow, sometimes. Everything feels urgent, but yeah.

Jeroen:

Yeah, definitely. Where do you put the limits nowadays? Do you put limits on the weekends?

Harrison:

Yes, I try. The way I kind of run my day is that I’ll get up early, do most of my work from home before heading into the office because I’m normally hit by a barrage of meetings and requests and calls and things. But I start the morning with some alone time, before the rest of the organization gets up, I guess, to write down a list of all the things I need to do that day in chronological order. And you can take some satisfaction once that list is finished, and definitely go home when you’re expected to or need to, but sometimes you don’t quite get there, and I guess that needs to be okay.

Jeroen:

What time do you get up?

Harrison:

Early. So I’m normally at my desk by seven, half seven, and I’ll work on my own individual work and tasks, and writing that list, I guess and setting up my team members for success with things they need to know, or do, till about nine-thirty. And then I’ll walk into the office. I’m lucky enough to not be too far away from it.

Jeroen:

Okay, so you get up at around six-thirty or so then?

Harrison:

Yeah, six.

Jeroen:

That’s not too bad. So you have two hours of undisrupted working time?

Harrison:

Yep, exactly. It’s going to be interesting to see how this changes with the time zone change. But I’m sure I’ll work something out.

Jeroen:

Do you live alone right now?

Harrison:

I live with my girlfriend, and she’s very patient with me, and fortunately a very deep sleeper. So she can let me get up, have a coffee and crack on with some work.

Jeroen:

Do you do anything to stay mentally and physically fit, or also nothing so far?

Harrison:

This is exactly the type of thing, I guess, that I’ve even noticed I’ve needed to get better at along that seven-year journey, which is still a short amount of time compared to many people in the industry.

But prior to Paddle, I played a ton of football, or soccer, depending on who’s listening to this, I guess. Played an awful lot. And then I neglected that part of my life, and fitness I think, for quite a while. I’m quite fit naturally. I walk around everywhere in London, but recently it’s been really important to me to get back into my running again, just to feel healthy and good within myself. It also solves my want to learn and read. You can kill two birds with one stone there, which is quite good.

I convinced myself I’d try kickboxing, much to a lot of people’s amusement in the office. But I haven’t quite gotten around to it yet.

Jeroen:

Great. Let’s say you sell Paddle now, in a few months, for a ton of money. You can spend your life the way you have always wanted. What would you do?

Harrison:

I’m sure I’d make myself busy pretty quickly. I’m really, really bad at chilling out and doing nothing. So I’m sure I’d sink my teeth into some problem that I spotted at some point. I don’t think I’d be able to resist.

Jeroen:

Yeah. I think you won’t be able to get your team because you’ve sold the company, so you would have something in your contract that says you cannot get your team along. So you start all alone?

Imagine the situation. You would start a new company from zero? Or would you spend a little time to think about things? Or would you take a long sabbatical?

Harrison:

Yeah, that’s an interesting question. I think I’d try and take a break. Knowing myself, I’m not sure I’d do more than about three weeks. I’m very lucky and enjoy the fact that I get to chat with, consult with and mentor a ton of great companies that I’ve met along the way. It’s always very interesting to hear about their problems and help them along their own journeys, and learn from one another, more importantly.

So I’m sure I’d be tempted to team up with someone that I’ve met along the way. Although having only done this as a founder, I imagine it’ll be a really interesting, and probably difficult experience for me to come into something that isn’t your own baby, I guess. It’s probably good learning for me to have, at some point.

Jeroen:

To join some other company?

Harrison:

Yeah.

Jeroen:

It would be, yes. So you said you’re based in London. Is that a good place to have a startup?

Harrison:

Yeah. I love it here. There’s an amazing, diverse, rich set of talent. I’m super proud of the fact that we are a company that’s 60% non-British. So we have a ton of great folks here from the UK, but an incredibly rich and diverse team, which helps us deliver better experiences to our potential customers, basically.

So you’ve got a lot of talent here, you’ve got access to capital, and some incredible investors who I’m also very grateful for. It’s the absolute right cocktail of ingredients you need, I think.

Jeroen:

Yeah. And where are you guys based in London? I was recently in London. I didn’t see any startups. I don’t know where they were hiding.

Harrison:

We are a very stereotypical kind of British startup. We’re based in Central Shoreditch. It’s near the Moorgate station, for anyone who knows London pretty well.

Jeroen:

Oh, okay. What other cool startups are located next to you, for instance?

Harrison:

We’re really lucky that there’s quite a few around. So Monzo, who is the challenger bank, is on the same road as us. You’ve got Busuu, which is a language learning startup, just around the corner. GoSquared have been around for a long time, and they’re just around the corner. There’s quite a lot in this little central area, actually. We’re quite fortunate.

Jeroen:

Cool. Slowly wrapping up, what is the latest good book you’ve read and why did you choose to read it?

Harrison:

There are two I probably want to mention. It’s maybe not the latest one, but one that’s probably been the most interesting to me recently.

About eight months ago we started working with an executive coach for the first time, and once you get to a stage where that’s viable, it’s something I’d definitely encourage other founders and CEOs to do. It’s been really, really transformative actually. And I was quite skeptical at the start, to be completely candid, but it’s been amazing.

And two books they’ve introduced me to, one which I loved, was a book called StandOut. It was kind of like a Myers-Briggs test, I’m not sure if you’ve ever done one of those? It is a personality type test. I never liked Myers-Briggs too much, I was never super fond of it. My answers always seem different, and apparently I’m doing it wrong, but I’m not sure. But this is an alternative to that, and it really helps you identify how you might be perceived, actually within a working environment, both good and bad, and being able to spot some of those behaviors in yourself, to make working with you an even better experience, I guess, or a better experience, has been really useful. So I’d certainly recommend that.

Jeroen:

Is that StandOut from JP Marky?

Harrison:

I think it’s Marcus Buckingham. Let me just search that for you. Standout, yep, Marcus Buckingham, StandOut 2.0. And then the next one I’m reading is What Got You Here Won’t Get You There, which is by Marshall Goldsmith. This one is around what we were just talking about. How all of those different character traits that you have, or all of the things that you’ve been doing day to day, which have allowed you to grow a business to a certain scale, how over time those need to evolve, or mold in order to set you up for the next level of success.

Again, it’s really talking about the behaviors that you have as a leader, and how to use those as effectively as you go to the next stage of growth, I guess.

Jeroen:

Cool. Is there anything you wish you would’ve known when you started out with Paddle or building startups in general?

Harrison:

Everything, I guess, having not done this before. I don’t know. The things that have become really obvious to me, I guess, is that every six months or so you will look back on your previous self and think, “How on earth did I function? What was I even doing, or thinking about?” And that’s okay.

I think we always need to strive for that learning trajectory. You, as a founder, need to be learning at the same rate your company is growing, if not faster, whilst also surrounding yourself with folks who know better than you, of course.

I think to go into this with that knowledge or that expectation from yourself is probably really important. I think I’d really be disappointed, or probably make some tough calls if I ever felt like I wasn’t growing at that rate any longer. I think that’s quite motivating, and something, yeah, I think it would be useful to know about going into this experience.

Jeroen:

So you’re saying that you have to keep learning faster than the organization. That’s what you wish you would’ve known when you started out?

Harrison:

Pretty much, yeah. I think that would be the most useful advice I could give to anyone, cracking on. Or to get really, really practical, thinking about mistakes we’ve made or areas for improvement, rather than a reflective self.

We’re 140 people now. We hired a hundred people in one year, and I think the thing that I’d have loved to know going into that experience is just how difficult knowledge sharing is, and how difficult that becomes when you have more new folks in the organization than old, and how you really need to optimize for that really early.

That is definitely a mistake we made, and it slows you down for a period before you accelerate again and benefit from all of those new individuals. A much more practical thing that we could have done better.

Jeroen:

How are you fixing that now?

Harrison:

Slowly, I guess. I think just being very purposeful with how you do this. We have much, much greater documentation internally, and use tools for that. We have a much larger people and talent team, who own learning and development at Paddle. And it’s just constantly encouraging a culture of learning within the organization.

We run afterschool sessions on SQL, Python. Every single person who joins the company runs through ‘how to build a Paddle checkout’ course.

Really instilling learning and sharing knowledge and feedback loops have to become a cultural thing. I think once you reach a certain stage and can’t all fit around a table, and tweaking your culture to reflect that, I think, is how we’ve gone about it. So it manifests itself everywhere.

Jeroen:

Okay. Final question. What’s the best piece of advice you’ve ever got?

Harrison:

Okay. I think, in the case of individually, I guess, as a founder, is about work/life balance, as we talked about today. It’s something along those lines. It is probably to not put the things off that would make you happier or more comfortable today, in case something might happen in the future.

I think talking to other founders like myself over the last seven years or so, I’ve realized we all have a habit of regularly putting things off, moving flat or committing to something like a holiday, in case a fundraiser happens during those months, or in case the move to the US happens earlier, or in case this big deal’s happening, X, Y or Z, you name it. We’ve heard all the excuses.

When you’re constantly planning for the future, and kind of neglecting the now, you’re making yourself and your life a lot more difficult than it needs to be. And you don’t even realize it. So to stop putting off things that would make you more comfortable or happy right now, I guess, for stuff that could happen in the future. I used to be very bad at that. I really benefited from concentrating on the now for both me and the people around me.

Jeroen:

Cool. That’s really good advice. Thank you again, Harrison, for being on Founder Coffee, it was really great to have you.

Harrison:

Thank you very much, yeah. It was amazing chatting with you!


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Jeroen Corthout

Co-Founder at Salesflare
I'm Co-Founder of Salesflare, the simply powerful CRM for small businesses. I love growth, automating sales, and building beautiful products.