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What was your first experience of investing?

The first investment I ever bought was a company called Parseq. I didn't have my own trading account at the time, so I did it through my father's stockbroker. 

The company was a penny stock, and I recall the broker saying something along the lines of, "I don't really know that business, but it's your money." The company specialised in digital mobile payments and it was a very early mover in the space. 

It secured a significant contract with O2 to develop and manage their mobile wallet and soon after was acquired by a group led by its own chief executive. 

I don't remember how much I made, but it was enough to convince me I was a good investor, which, as it turns out, wasn't the best lesson. 

Has there been a person or resource you have found most helpful in your investment journey?

I remember MoneyWeek always being on the kitchen table at home. It was instrumental in my introduction to finance and investing years before the world was opened up with online resources. 

What has been the riskiest investment you have made, or considered?

I own a vehicle that underwrites insurance at Lloyd's of London. The potential for losses technically exceeds more than 100%. 

Have you had any investments that have performed extremely well or extremely poorly? If yes, what were they?

Looking at my portfolio right now, Admiral has been my best-performing investment of the past decade. Insurance is a market I am familiar with, and I appreciate the company's dividend policy and its tradition of distributing stock to staff each year. BP Marsh, the early-stage insurance investor, has also been another winner. The mistake I made there was selling too early. 

The worst-performing investment in my portfolio today is Diageo. It's made some mistakes, but as someone who writes about whisky in his spare time, I know the value of the brands is stronger than ever. 

What’s next for your investing journey?

It's never-ending! There's always something to learn and there's always something exciting on the horizon. 
  
What would you tell your 20-something self about investing?

You're not Warren Buffett. You will make mistakes. You need to find your way.

Thanks Rupert!

This interview is for information only and it is not investment advice. It is for use in the United Kingdom only. Investments and/or investment services may not be suitable for all investors. Capital is at risk and past performance is not an indicator of future performance.

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