Talking problems, people and perseverance with Christian Owens, Founder and CEO of Paddle.

What got you started on your journey?

I taught myself to code when I was 14 and started building websites. One of my customers asked me for an invoice and I had no idea what to do! So I googled “how to make an invoice” and quickbooks came up. It was maybe £8 a month and I didn’t want to pay that, so I built an invoicing product. I realised I really enjoyed building products as opposed to creating websites, so I started focusing all of my energy on building that invoicing tool.

I taught myself to code by talking to other software developers and people who were building apps that I liked. I enjoyed ripping apps apart and understanding how they worked and decided to start a business bundling different pieces of business software together, with my invoicing product bundled in.

I was 15 when I launched that business and it did reasonably well - $300,000 / $400,000 in sales in the first week. That was enough for me to be able to convince my parents to let me drop out of school when I was 16 and I then started scaling the business, achieving $2m or $3m in revenue in the first 12-18 months. I realised I was spending all of my time on stuff that wasn’t building a product anymore and was instead handling lots of complex stuff to help me with selling - taking payments, dealing with taxes, selling internationally. I was already sick of the fact I wasn’t building anything else, so I hired someone to run that business and focused all of my energy on solving the problem of selling software internationally.

That was the impetus. I didn’t want anybody to be in the same situation I was, where they really loved building software but then ended up focusing all of their time and energy on stuff that wasn’t building a product. So I started to Paddle to try and solve that problem for everyone else, by creating a subscription and commerce platform to help software founders do what they love, build great software.

What was your vision back then and what does it look like now?

I think it’s broadly the same, but the breadth has widened.

When I first started Paddle we were building a platform for people just like me - individuals or small teams building a software product and taking it to market. The unique thing about software is that it can be in any country immediately, there are no barriers. So initially it was the same vision and mission that it is today, providing our clients with the operational and commercial infrastructure to allow them to focus on building a great product and delighting their customers, not building that infrastructure for themselves.

I soon realised that, even as a company grows and has more resources, the problems of how to sell internationally and deal with commerce, finance and operations get way more complex, with far higher stakes and it doesn’t matter if you have 2, 200 or 2,000 in your company, the problem is still the same. Suddenly we realised Paddle could be genuinely applicable to every software business in the world. So that’s the vision: to help every software company focus on doing what they love, building great products and growing fast.

Attending WWDC for the first time opened my eyes to the scale of what we could achieve

We initially started by selling to people like me. I started building software for the Mac, and the only real way that we knew how to go to market was to talk to mac and apple developers.

One of the big inflection points was the first time we went to WWDC (the Apple developer conference) and started making a name for ourselves. Fast forward a couple of years and we were the no1. provider of e-commerce infrastructure for Mac and Apple. We recognised then that we needed to focus our efforts on an industry and build something really valuable and if we did that there was no limit to our ability to sell to different sizes and different types of software companies.

Before that, we had focused on people who were building simple pieces of software for individuals, not businesses. When we started selling to businesses building software for other businesses - companies we really admired and never thought we’d be able to sell to - we gained confidence that the problem we had identified existed in software companies of all shapes and sizes.

Hiring game changers is hard!

I think I was quite lucky early on in realising that 1) I had no idea what I was doing and 2) early on I found a couple of people who were really great.

Fortunately I’m self-aware enough to realise that I need to hire people who are absolutely better than me at the thing they’ve chosen to do in their lives.

I’ve tried to make this a common thread through all of the people I’ve been involved in hiring. I ask myself, “can I learn from this person?” or “ from the last ten people that we’ve hired, could I feel like the most stupid person in the room?”. As long as that remains true, we’re constantly raising the bar.

Some of the hardest hires to make have been in the exec team and leadership roles, where, make no mistake about it, I’m hiring for people who are significantly better and more experienced than me. Trying to convince someone with 20 years of experience, who has built companies of a much greater magnitude than where we are today, to believe in a 24 year olds’ view of how the world should be is challenging in a lot of ways, but it’s how you get some of the best people. They need a mix of experience and skills in order to do the job, and you can assess for that. But there are other things that matter to me: they’ve got to be a little bit crazy, crazy enough to think that we can deliver on our vision, and crazy enough to gloss over some of the imperfections of the organisation as it is today. They have to have the belief and confidence in their own ability to come in and help shape and fix things.

Hiring has been and remains to be the hardest thing we do. Crafting a good team and finding great people will always be incredibly tough.

I’m constantly doing things I’ve never done before

Company wise, there is something challenging to deal with every week. I’ve never had a job before, so just being employed is one thing that’s challenging for me but also constantly doing things I’ve never done before.

For a lot of first or second time founders, a challenge that you may have is the interesting dynamic that you have with a board.

If you’re hiring a senior person for example, let’s say a VP Sales and you’re going through this list of candidates and you’re discussing a candidate with the board, you may think they’re the best person you’ve ever seen but you get feedback of ‘oh they’ve never done this before, they haven’t managed a team this big’ etc. Part of me thinks, ‘shit neither have I, what makes me qualified to do that, in spite of having no experience?’. I think that’s a difficult thing, managing the expectations of yourself, when the bar is so high and when the expectations from others are so high.

Plenty of horrible things have happened along the way. There is a really funny anecdote, which always sticks in my mind and gave us a first taste for how things can go wrong. We got sued for trademark infringement before we even launched the company. It was a great baptism of ‘ah shit, this is going to be harder than we thought’.

My favourite moment (it’s funny now, it wasn’t at the time) was we were just hiring our first senior person (Hugo our CFO). There were only 7 of us in the company at the time, and we’d just done $26,000 of revenue in the last month and it was the best month we’d ever had. I distinctly remember the point when we were about to hire him, it was all going well and he was super excited about joining, and then we had a call with our largest customer who was $22,000 of our $26,000 month and we’d paid for these cupcakes, branded with their logo, to celebrate their launch with us.

We were on a skype call with the DHL guys behind us, delivering these cupcakes at the same time as the customer was firing us. It was just a really funny moment in Paddle history, but the funnier moment was calling this amazing CFO candidate shortly after that and telling him we’d gone from $25K revenue last month to next month $2K and asking if he still wanted to join. Fortunately, he said yes.

There are so many examples like this, where you go from the highest of highs to the lowest of lows, sometimes within minutes. Sometimes, during these moments, we wondered why we were even bothering but then the next day something amazing would happen, to make you forget all about it and just tell funny stories about it instead. It’s a constant reminder that it doesn’t matter whether you’re particularly smart but that perseverance throughout all of these things is one of the most important traits to have.

Surround yourself with founders on similar journeys

Having a group of people who are in a reasonably similar situation helps. One of the things about doing this is that you’re always thinking about how the business can be bigger, and better and more successful than it is. You have all of these challenges along the way, but they’re rarely unique to you and someone else has probably gone through them before. So you should surround yourself with those people, people who are 6-12 months ahead of you on this journey.

If you go to dinner with them and spend two hours moaning about things that are wrong, you will see that everyone is struggling with the same things or has just overcome them and it’s helpful to know that.

Never forget that it is the people who are the most important thing on the journey.

You can have the best idea and more money than anyone else in the world, but if you don’t have a supporting cast of world class people, you’re