Mistakes I've made with money

Every year since about 2010, I sit down with a written document I call my life plan. I rate out of ten how I am doing across family, health, work, personal time, and finances. The finance score is usually where I lie to myself the most. I look at spreadsheets, add up the supposed value of illiquid startup shares, factor in the house, and give myself a solid eight. Then January rolls around, a sudden tax bill arrives or an actual brilliant investment opportunity appears, and I realise I have almost no cash. It is a specific, recurring stupidity I have spent over a decade trying to unlearn.

Buying a seat at the table

To understand how I lose money, you have to understand why I part with it in the first place. When Fredrik Bage and I were building Mediapilot in Stockholm, I was entirely focused. We grew that company over roughly seven years, created more than a hundred jobs, and the metrics of success were simple: revenue and survival. But after you step away from an operating role, the quiet can be deafening. I remember sitting in meetings later on, holding a bit of cash, and feeling this sudden urge to stay in the mix. I started writing angel cheques. I told myself I was diversifying. I was actually just buying a feeling. I wanted the coffee meetings with ambitious founders. I wanted to read investor updates and feel like I was still in the arena.

The easiest way to lose money is to treat investing as an entry fee for feeling relevant.

I backed ideas I barely understood because the founder was charismatic and I wanted to be part of the group backing them. My old friend Fredrik originally convinced me to go into commission-only sales because he told me I would be good at it. It turns out, being a salesman makes you incredibly susceptible to a good pitch. You respect the hustle so much you forget to underwrite the business. I put money into early-stage companies without demanding board seats or proper reporting, simply because I wanted to be liked. Most of those investments went to zero. The cash evaporated, and the coffee meetings stopped immediately. The financial loss stung, but the pattern behind it was what bothered me. I was using my bank account to medicate my own boredom.

Rich on a spreadsheet, sweating the actual bills

That ego-driven investing led directly to my second favourite mistake: chronic illiquidity. Because I viewed cash sitting in a bank account as lazy, I threw it at private companies and property. By the time I moved my family from Sweden to Marbella in 2018—a move that was only supposed to last two years—my net worth looked very healthy on my laptop screen. But you cannot buy groceries with secondary shares in a startup. I have had periods living in Spain where my paper wealth was at an all-time high, yet I was checking my current account before taking my family out for dinner. Being completely illiquid at the exact wrong moment is a uniquely humiliating feeling. It forces you to pass on genuinely great opportunities because your capital is buried in assets that might take three years to sell. When a real chance came along to back something I deeply believed in, I had to sit on my hands.

I have not entirely cured myself of this. I still put money into property, and I still make a small number of angel investments alongside building Anchor and Substrat. Startups are inherently illiquid. But the filter has changed. When someone pitches me now, I force myself to wait a week before responding. I ask myself if I want to own a piece of the business, or if I just want the founder to think highly of me. I am finally learning to hold cash, letting it sit there doing absolutely nothing, so that when a real, undeniable opportunity appears, I am actually ready for it. I still review the life plan every December. I just judge the finance score by what I can actually spend, rather than what my ego tells me I am worth.