James Lenehan is founder and chief executive of WinWin, which offers reward and incentive solutions. Over the past two decades, he has built, grown and exited companies across the loyalty and rewards space. He is currently focused on expanding his restaurant platform, EarlyTable. Are you a saver or a spender?I’m disciplined enough when it comes to investing and business, but I really like using money to create family experiences, and I’m happy to splash out on those. But Ireland has become more expensive, so I am definitely more conscious of our family outgoings now.What was the first job you received money for, and how much were you paid?I cut people’s grass one summer as a teenager. I remember turning up at a house with a two-acre garden. I was given their old push mower – remember the ones with no engine, just elbow grease? It took me five hours and I was paid €2 per hour. It almost broke me. Do you shop around for better value?Yes, but I’d describe it more as looking for value than just the cheapest price. I’ve spent most of my career thinking about how to create value for customers and employees, so I naturally look for it in my own decisions, too. What has been your most extravagant purchase, and how much did it cost?Our family home. It’s by far the biggest number attached to anything I’ve bought but it doesn’t feel extravagant, more like an investment in how we live day to day. That’s how I tend to justify most big purchases, to be honest.What purchase have you made that you consider the best value for money?Spotify is right up there, an endless library of music for the price of a few coffees each month. I love music so it still feels like incredible value. More recently, I bought a 3m x 2m laminated world map for the kids. They love rolling it out on the floor and picking cities and countries they want us to visit. It cost very little, but it’s probably delivered more curiosity and conversation than anything else I’ve bought in the past year or so.Is there anything you regret spending money on?Yes, backing the wrong people in business or not asking the right questions early enough. Financially those decisions can be expensive, but the real cost is the distraction and time lost. You tend to remember those lessons more than any financial gain.Do you haggle over prices?Not in everyday life here, but whenever I get the chance on holidays I love a good haggle. Do you invest in shares and/or cryptocurrency?Yes, I invest in shares, mainly growth companies, which can sometimes feel like a white-knuckle ride. I enjoy understanding businesses and backing them over time. I own some crypto, but I tend to prefer investments where I can get my head around the underlying value.[ How to invest in crypto, CFDs and private equityOpens in new window ]Do you have a retirement or pension plan?Yes, I do, but most of my focus has been on building businesses rather than a traditional pension. My original strategy was along the lines of building something meaningful and figuring the rest out after, but now I’m more focused on contributing to my pension. What was the last thing you bought, and was it good value for money?I was in denial about my need to wear reading glasses but eventually agreed to buy a few cheap ones online to see how they felt. My goodness, I didn’t know what I was missing. I have built a nice collection of €20 glasses but I really think it’s time for a trip to the optician.Have you ever lost money?Yes, many times. If you’re building businesses, it comes with the territory. You need to speculate to accumulate. I also lost money on property during what I term the Great Financial Crisis. Are you a gambler, and if so, have you ever had a big win?I never place bets; I’d see business as enough of a calculated risk without needing to add gambling on top. That said, I’ve definitely had days in business that felt like I was gambling, albeit with much larger stakes.What is your best habit when it comes to money? And your worst?My best habit is thinking long-term and focusing on value rather than short-term gain. My worst habit is moving too quickly sometimes, particularly when I get excited about an idea. This has happened more often than it probably should.How much money do you have on you now?I never carry cash. If you asked me 20 years ago, I’d probably have had €50 in my pocket and a very clear plan for how to spend it. In conversation with Tony Clayton-Lea