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After Pointy windfall, Heaslip beds down in the fields of Flenders

Ireland's former rugby star is building an increasing portfolio of investments. Adrian Weckler meets Jamie Heaslip to find out about tech, schadenfreude culture and switching from sport to investing


On the ball: Former Ireland rugby player Jamie Heaslip has made a series of successful startup investments

On the ball: Former Ireland rugby player Jamie Heaslip has made a series of successful startup investments

On the ball: Former Ireland rugby player Jamie Heaslip has made a series of successful startup investments

Siri, who is Jamie Heaslip? "Jamie Heaslip is a technology, media and leisure sector investor... who once played sport."

A sneak preview of the former Leinster and Ireland rugby player's Wikipedia timeline in 2025? Perhaps.

The six-foot-four son of a brigadier general is well on his way.

Heaslip, 36, is becoming a textbook example of how to transition from sport into modern business.

Eschewing the role of a corporate mascot, wheeled out on game days to entertain cigar-chomping clients, Heaslip has chosen the role of tech investor and promoter, meeting young startups to see whether they're worth a punt.

Some are. One of his earliest bets has just paid off spectacularly. Pointy, the retail listing startup co-founded by Charles Bibby and Mark Cummins, recently announced its acquisition by Google in a nine-figure deal. Heaslip is understood to have made a six-figure sum from his initial investment.


Jamie Heaslip playing for Ireland

Jamie Heaslip playing for Ireland

Other bets, such as the analytics firm Kitman Labs, look promising for a significantly augmented return in the near future too.

And if tech hits another bubble, he has a few Dublin pubs to fall back on, such as The Bridge 1859 and Lemon & Duke, as well as a job at Google he could probably return to.

But Heaslip doesn't think that startup tech is going south any time soon. He has just taken a deeper role in a fintech firm, Flender, that has created a new online platform to match lenders with small businesses who want to borrow sums up to €300,000.

Adrian Weckler sat down with Heaslip to ask him about tech, trends, culture and the transition from sport to investing.

Ireland's former rugby star is building an increasing portfolio of investments. Adrian Weckler meets Jamie Heaslip to find out about tech, schadenfreude culture and switching from sport to investing

Adrian Weckler (AW): Why did you initially choose tech?

Jamie Heaslip (JH): I wanted to work at something that did things at scale and that was based out of Ireland. I looked at aviation leasing, a huge industry which is largely based on the Shelbourne Road in Dublin. But that was just too much travel for me. So I chose tech.

AW: We often see well-known sporting figures taken on by businesses as brand ambassadors. Sometimes it can almost seem that they become mascots, rather than full executives. Was that ever a danger for you? Do you ever feel like one now?

JH: Yeah, it's a line that you have to be careful with. But at Google, for example, that just wouldn't fly. Most people wouldn't have recognised me. And that was half the attraction of going there.

AW: You've just made a very substantial return from your early investment in Pointy, bought by Google for over €100m. How and why did you pick that company to invest in?

JH: I didn't know much about SEO optimisation or retail, but I understood the opportunity and the potential scale.

I understood the problems facing a company like Google, who we think never has any problems, versus what Amazon is doing. And that the person losing out is the SME or the corner shop. I also invest as much in teams as in the idea.

With Mark [Cummins] and Charles [Bibby, Pointy's co-founders], you could see a dynamic in the way they carried themselves and how they do business.

AW: You now have a fairly sizeable portfolio of investments, from pubs to media to tech. Would you say you've had more hits than misses?

JH: I know how lucky I am to be in a time and place when you meet good people.

You make your own luck a little bit by being curious and going out and meeting these people. But it's a bit like sport. I've often been asked why, for years, I never got injured. It was blind luck.

AW: While all this was going on, you worked as a regular staff member at Google for about a year. Why there?

JH: I had invested in a couple of tech companies that were scaling and doing OK. I thought that I might go into one of them. But that seemed too easy in a way; I'd just be going in as a name.

So I wanted to pick a company where I wouldn't go in as a name, where I would just have to learn the trade effectively. And that's what happened in Google.

AW: What exactly did you do at Google?

JH: It was called 'large client services'. Some of Google's top clients, big-name brands, are spending a lot of money. So it's a more hands-on service. I was a senior account manager, looking over a couple of different clients. I got to work with loads of different businesses and different advertising models. I learned a lot.

AW: But of all your investment companies, you've picked one to run with in a deeper way - Flender.

JH: Yes, they came to me as they were scaling very well. I was already an investor. They've gone from one million originations in 2017 to four million in 2018 to just under 13 million last year. It's the fastest-growing digital lending platform in Ireland with fast finance to SMEs. Our average loan size is about €100,000.

AW: This isn't regulated in the same way as Bank of Ireland or another lender?

JH: No, they're unsecured loans. There's risk, like any investment. But our default rate is less than 1pc.

The real attraction is speed. You can upload your information and get a decision today and then your money tomorrow. A bank will take anywhere from six to eight weeks, which may even be a slow no. We have split it into retail and institutional lending.

Retail is where you and I can come on to the platform, put 50 grand in and decide who you want to lend to.

But that is actually becoming a smaller part of the business. We secured a €75m credit line in the fourth quarter of last year of institutional money. That's institutional money which wouldn't be on the market and that goes to business.

AW: So that means you have up to €75m to lend out?

JH: Yes, we want to loan €100m this year. We're about to hit 20 million worth of business loans since starting. That's a big milestone for us.

AW: What happens regarding a default situation?

JH: We have teams that manage that.

AW: Does that mean you knock on someone's door at 1am in the morning?

JH: Nope. Luckily, it's not something we've had to deal with a lot.

My job is to step into a leadership role and help that team scale. For me, it's going from such a big global company [Google] and seeing their processes and how they orchestrate things. And it's also looking over to Kitman and Pointy and seeing what we might learn from them.

AW: With your increasing dive into the tech world, have you ever worried that you might become part of a 'tech bro' culture?

JH: I'm not sure what that is.

AW: In some tech companies, there have been problems of toxicity, and where the culture has resulted in female staff being marginalised. Companies like Uber have had significant challenges with that.

JH: I haven't seen that in any of the ones that I'm involved in. Flender is very small, but there are more men there than women.

But in terms of having a diverse group, you definitely need that. Without it, you'll get blind spots and group-think.

If you don't create a place where people feel safe to work, where they enjoy working, they'll leave.

AW: What about tech, in general? The industry used to be described in terms of being a plucky disrupter, a business model with a moral compass and a conscience.

Now it's often painted as an agent of cynical manipulation and moral decline. Do you think the 'tech is evil' narrative holds any water?

JH: I'm not sure. I'm still undecided about things like smart home technology.

You insert this device into your house for convenience but then you give up more data.

On the one hand, it's your data you're giving away free. But then again, I walk around with a smartphone.

AW: Let me ask you about your former occupation. What did you make of the schadenfreude in some parts of the press and on social media when Ireland were beaten by Japan and New Zealand in the World Cup a few months back?

JH: I don't know why some people were revelling in the failure of the team to get past the quarter final.

I can't speak for them. Maybe they just, you know, didn't like all the hype that was around the team in the first place.

AW: There was definitely a strain of opinion out there that rugby is a private posh boys' sport. There were quite a few who seemed to really enjoy the defeat, maybe from a position of resentment or social division.

JH: There are clearly people who don't feel connected to this team. Maybe there's something we have to do about that, to look at where the majority of our players are coming from in terms of clubs, schools and catchment areas.

AW: But in terms of the schadenfreude and the revelling, as a former player, how did you feel about that?

JH: If we all had the same opinion, it might be very boring.

You need people who have a different voice, who question and maybe go against what is the common or easy narrative at the time.

But we shouldn't get really carried away. This is just a sport. There are some other properly serious things going on.

AW: What about pay TV and rugby? Do you think it would hit the game's popularity?

JH: I believe it would. I think you have to keep the national events, like the Six Nations, on free-to-air TV. Rugby is still quite a niche sport.

To hear a full podcast with Jamie Heaslip, listen to The Big Tech Show on Spotify, Soundcloud or on independent.ie/podcasts this Friday lunchtime

Ireland's former rugby star is building an increasing portfolio of investments. Adrian Weckler meets Jamie Heaslip to find out about tech, schadenfreude culture and switching from sport to investing

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