CEO on the spot: 10 questions with GoFundMe’s Tim Cadogan

My aspirations evolved. I started as a product manager at a tech company in 1999. I learnt a lot about management in that role because I had to work with a lot of teams that I didn’t directly manage.

This means you’ve got to learn to be clear and to influence people in lots of different areas. That led me to general management and in the mid-2000s I thought it would be interesting to be a CEO.

My first CEO job was at a startup, bringing the company up from zero revenue, and I really enjoyed it. So while I wasn’t one of those people who grew up thinking they want to be a CEO, that desire has evolved over time.

Three reasons, really. Firstly, I spent more than a decade at my startup, OpenX, which had grown to a good size, but I was looking for something new. Frankly, it was an opportunity to learn at a new, fast pace.

Secondly, I wanted to get back to something that was consumer-focused.

Lastly, I wanted to do something at work that felt really good and had an impact that you could feel day in, day out. I was very lucky to enter the interview process for GoFundMe and come out of it with an offer to be the CEO. That third reason was the real big driver and differentiator.

You need to understand that leadership is a team sport. When you look at a lot of the literature on leadership, it tends to focus on the role of the individual; the person who makes important decisions in the big moments.

In reality, it’s much more of a group effort than is often portrayed and that’s my approach. Leaders need a good core team of three to seven people – probably not much more than that. These people need to be aligned and allowed to play to their individual strengths. You can then make the tough decisions together.

It’s also important to make the hard decisions early. When you lead and operate a company, you’re consistently faced with a lot of challenges. This means it pays to have time to think ahead and consider what tricky issues might come your way in the future. You need to try to anticipate the tough decisions, because the sooner you make them, the sooner you can give the whole team clarity and lay out the path forward.

It’s the same as a rugby team, you need lots of different people to make a winning team. You need tall people, short people, strong people and fast people – you can’t have just one type. You’ve got to find the right mix. 

So, for me, I need someone who’s great at marketing, someone who’s great at product technology and a great CFO. Each role requires different skills, so I need to find people who have good experience and talent for each role but who also share a common mindset and believe in the company purpose. That’s where the synthesis comes in. 

However, while difference is good, you still need to connect around a single sense of purpose. It can be hard to get the right mix but, once you’ve got it, you really can start to hit the gas.

Find the right balance between leaning into the new and relying on what you already know. This requires you to know yourself and how much risk you are willing to take. If you’re reasonably risk-seeking, you might want to spend 50% of your time on new business challenges and 50% on opportunities you have experience of and know you can nail. 

If you’re a more conservative person, your mix might be 80% things you’re confident in and 20% new challenges. There’s no right answer. You need to reflect, decide where you sit on that spectrum and then find opportunities that are about the right balance.

My first day in the role was 2 March 2020, right at the start of the pandemic. By Friday of that week, we decided to take the entire company remote. 

GoFundMe had a massive surge in demand from people who were impacted by Covid. Much of this was also around causes we’d not dealt with before. Many patrons were starting fundraisers for their favourite restaurant, bar or music venue. So it created lots of complexity.

At that point, I inherited a fairly light executive team. I didn’t have a CFO, head of product or head of marketing and I had 15 direct reports. This meant I had to act as the interim CFO as well as the CEO. 

That first year was very challenging, but we got through it. It forced me to gain a deep understanding of the business, while also navigating a global crisis and making sure that we were there for the customers who needed us urgently.

It gave me a great sense of duty and I understood the role the company had to play in solving these problems as quickly as we could.

At the root of what we do is the concept that someone has to be brave enough to ask for help. Most of us find this difficult, even if it’s from our family.

I think we have made progress in making this easier for people and that is a fundamentally important thing. It has been manifested in many different situations – in big crises but also for wonderful causes.

We just had a really lovely fundraiser for a new statue of  Terry Jones from Monty Python. His children set it up and it’s now raised the £120,000 goal. Michael Palin did the video for it and Eddie Izzard did the final donation to put it over the top.

I think that’s a lovely example of people coming together in memory of someone who did something amazing and it’s brought the whole community and multiple generations of comedians together in support of it. So I think that’s a great example.

There is a clarity of purpose that ripples through GoFundMe. We want to help people help each other. Having that objective every day to inform our decisions and our actions is enormously powerful.

I generally think most business books could have been an article. But one that I think is very good is Ben Horowitz’s The Hard Thing About Hard Things.

A lot of business books rely on hindsight and frame a glorious challenge that the leader overcame. This book presents a more realistic view of how much of a grind being a leader can be and the true challenge of making tough decisions. He does a really nice job of more accurately framing what it’s like. 

I spend a lot of time in the mountains and that manifests itself in a couple of different ways – it’s part of the reason I ended up moving to California.

A lot of people meditate or have a hobby that helps them to clear their mind. That’s my version of it. I can be trundling around the mountains for a couple of hours on a Saturday morning and suddenly realise I haven’t thought about anything except the thing I’m doing for 40 minutes.

I do trail running and have run a few ultra races, some of which were 100 miles in a single day. I’ve also run the Marathon des Sables, which takes place in the Sahara desert. That’s 150 miles but you run it over the course of a week. They’re a whole different kind of challenge. 

I’m also a volunteer search and rescue operator and I’ve been doing that for 15 years, which is pretty special.

I find that doing something physically demanding and being in nature is super helpful.