Having spoken in over 30 countries on six continents, rock-and-roll-roadie-turned-entrepreneur Richard Mulholland is a natural-born maverick and independent thinker. Richard, who is the founder of presentation powerhouse Missing Link, believes in challenging the status quo. He believes that doubt inspires the absolute best investments – of any kind. So he was a natural choice when we were considering who should be our first guest for our online series, IFSA Prosperity Sessions.

As far as best investments go, Richard has written three books: Legacide, Boredom Slayer, and Story Seller. He was voted top 40 under 40, and one of the top 300 South Africans to take to lunch. Apart from designing better ways for clients to connect to the audiences they serve, he is also the co-founder of 21Tanks and The Sales Department. Mostly though, Rich is a husband, father, son, brother and uncle.

During the first IFSA Prosperity Session, held in February 2022, Richard chatted to IFSA CEO Frikkie van Loggerenberg about his best investments and critical business insights over the years and what role doubt has played in securing quality returns.

Here, we share some of the insights that came out of their conversation.

On the topic of best investments, where were you born and what did you study?

Ha! So I come from Glasgow, Scotland. I moved to South Africa when I was nine years old. I studied absolutely nothing. Basically, one guy did worse than me in school and the guy that did worse than him, failed. So, glad you’d have me. I didn’t tell you this beforehand – just in case.

Tell us about why you invested in starting your company, Missing Link.

What inspired me to start the company wasn’t passion. But instead, absolute frustration. I used to work in rock and roll. I toured with bands like Iron Maiden and Def Leppard. But in South Africa, people don’t go to concerts in the winter, which is funny to me. Because if people didn’t go to concerts when the weather was bad in Scotland, then there would never be a concert. But, what happened was, we all had to go out there and get work [in winter]. And one of the easiest places to get work was in corporate.

I would go to these CEOs, get people all excited and say: ‘We’re going to help you to make your conference like a rock show,’ and they’d be all like ‘yes, we want some of that,’ and so I would get the lighting and the sound and the AV and the staging, and still – it didn’t matter.

The thing is, it didn’t matter how much of a show you put on, because if the CEO came up and stood up on stage and gave a terrible performance – then it was terrible. If it was brilliant, then it was brilliant. So, it all came down to the presentation. And so, I quit my job and founded Missing Link at 22. Not because I loved presentations, but because I hated them enough to fix them.

I believe that the best investments in life occur on the other side of a presentation. I want to make it better for people to have a better chance at the other side of that presentation.

Is finding the best investments as simple as connecting a solution to a challenge?

Yeah, for sure. Look, entrepreneurs are fuelled by doubt – other people’s doubt. That’s where the opportunity exists.

For me, an entrepreneur either fixes a problem or fills a gap. You can’t have people start businesses from things like love.

I mean, you could, but… Here’s an example: I love board games. If I started a board game store, it’s a tricky biscuit. Wherever there is market saturation, things become tricky. But if you look for something that doesn’t work, you work under the assumption that it wouldn’t work for other people as well. And therefore, there is a need, and that need becomes the opportunity.

Don’t worry about doing what makes you happy. Worry about making others happy (albeit not irrationally), and in doing so, you will find your happiness.

How and where do you invest the earnings from your business?

I invest in other entrepreneurs who I believe are onto something. One of the biggest mistakes I made early in my career was thinking that investing in myself would be good enough. But as it turns out – it wasn’t.

If I could go back in time and change anything, I would start investing earlier.

The truth is I tried to diversify as much as possible, because of my lack of knowledge in this space. I also invest in some big ticket items, some private equity, and property. Again – I take a couple of ‘swings’ as well.

Do you have any practical advice for making the best investments?

Think of investing as a much wider term than you have been thinking. It’s not nearly just about the financial aspect of the game. Time would be a better thing to focus on. Now that is really something you cannot make any more of. But also, on its own, not good enough. It’s about being wide open and holistically awake.

Is investing in private business better than vanilla-type class investments?

Well, yeah. When I started my business, I believed that if I could reinvest any profit back into the business, that would be the best investment I could make. But then, I was investing in a CEO, which was me. Now, if I had to choose and line myself up to Bill Gates, Steve Jobs or whoever was important at the time, and say – who would I rather invest in, for some reason, I always picked myself, which was technically not a great strategy. Look, I think you need to back yourself enough, but hedging on other CEOs’ expertise is a good idea too.

I think, I started investing late, but not too late. In other businesses as well. I invest partially back into the business and, funny enough, that’s not because I want to make more money, it’s because I believe in our business and I want to scale our impact. So, we have to invest to scale our impact.

The place where I plan on making money actually is my other investments. My purpose, my passion, and the paying of our salaries and my day-to-day life will come from my business. But for me, my future, my proverbial nest-egg, is coming from my investments.

Do you find doubt coming to the forefront more often these days?

No. Because it was consistently there. All your future best investments exist in doubt. If there is certainty, then you are too late. One of my most significant losses was when I invested in something that I thought was a surefire thing. I bought shares in some US stocks and thought that the growth I’d been seeing would continue. It did not!

Instead of taking a go when there was still doubt, I waited for things to feel certain. It’s been one of my biggest losses to date. In doubt there is opportunity. In the shadows of uncertainty – that’s where it lives.

It’s my belief that if you wait for certainty you are missing most of the opportunity. That’s why I see this pandemic as a good thing also. When a state of disaster was declared, I lost nearly all of my business. Just a short while later, I wrote a post on LinkedIn saying that this might be the best thing that ever happened to me. And definitely the best thing to ever happen to my business. Shortly after writing that blog, we experienced the best month ever.

Can you use doubt as a motivator for transforming challenges into prosperity?

Completely. But what other motivator than doubt is there? If you’re sitting there at home, on the toilet, going through TikTok videos, you know – how big a problem do you have? That’s why I think Africa is such an amazing place to identify the best investments for yielding optimal returns. Because there’s work to be done. Especially because there’s doubt and things we have to fix. It’s a beautiful place to be in that regard.

We need to become fuelled by these doubts. We need to understand that doubt means there is a problem. Again, for me, doubt is the god particle of curiosity. And curiosity is the mother of innovation.

My friend Nic Haralambous built his entire thought process around the idea of curiosity being the catalyst for everything meaningful. I fundamentally believe that. I believe that curiosity comes out of doubt. Those moments you look at something and think ‘come on’.

Do you think there are many people who ‘get’ the benefit of doubt?

Some people choose to not go to doubt at all. They choose to skip doubt and go straight into disbelief. ‘That can’t be true. No. I refuse.’ And then they research things that apply to that bias. That’s not the best kind of investments, at all.

I look at it and think, sure, you’re having a go. But I also look at it and try to figure it out a little bit. And then, my doubt fuels my curiosity and my curiosity fuels my knowledge, and only then am I able to create an opinion. That’s the process I’d go through to get to new opportunities.

On my arm is tattooed: ‘Reclaim yourself, question everything.’ And the only way I think we can reclaim ourselves in any situation is to question the biases we have internally.

How does IFSA’s mantra ‘In Doubt We Trust’ resonate with you?

Well, I mean – you’re speaking my language. I love the idea of ‘In Doubt We Trust’ because I think that is really what we should be trusting in.

I can’t think of anything that I’ve done that is of significance that didn’t stem from a position of doubt. At all. The difference is that people jump into that pool of doubt and see that as a negative place.

I have always seen doubt as a positive place. In fact, one of our biggest challenges is dealing with when we find ourselves on the OK plateau. When you’re sitting in your business and you’re looking around and you think everything is working so well; this is good… this feels good… this is a nice, comfy stair! That’s when I get antsy and worried.

That’s also when I get bored, because I do find business relatively boring in general. Or more specifically, I find the operational aspect of my business boring. Luckily I have learned to outsource that part of my business. Now, I no longer have that problem.