Alan Smith

I don’t watch a lot of TV anymore, but regularly find myself going down rabbit holes on YouTube! One person I always enjoy watching is Michael Saylor. AS CEO of major US public company, Strategy, Saylor is one of the world’s most successful entrepreneurs and like many founders, he’s a voracious reader. And there’s one work he regularly recommends: Will and Ariel Durant’s The Story of Civilization. It’s not exactly a light holiday read. Eleven volumes. Around 13,500 pages. Roughly four million...

Florence, 1397. A banker named Giovanni di Bicci de' Medici opens a modest counting house on a narrow street near the wool markets. His business is unglamorous: currency exchange, deposits, and loans. When a merchant needs cash before a shipment sells or a harvest comes in, Giovanni doesn't ask him to sell what he owns. He asks him to pledge it instead - gold, goods, sometimes fine art - held as security against the loan, and handed back the moment it's repaid. It wasn’t Giovanni's idea....

You spend 20 or 30 years building wealth partly to give your children a better life. Then, if you're successful enough, you face an uncomfortable question: could giving them too much actually make their lives worse? A few years ago, I was talking with a founder who’d recently sold his business for a life-changing sum. I asked him the question I often ask people in that position: what's the plan for the kids? He didn't hesitate. "I don't want to give them too much. It would rob them of their...

What happens when you achieve everything you've spent your adult life chasing? All the things that seemed unimaginable when you were starting out are suddenly yours. The house. The car. Financial security. Time. Freedom. What happens then? I'm currently in Scotland, spending time with my family, and I've been having long conversations with my dad, who's 85. He was a successful property developer who retired in his fifties. He'd earned the right never to work another day in his life. He bought...

Why does your business exist? Not the mission statement version. Not the answer you give investors or put on your careers page. The real answer. The one you’d explain if you gave yourself the time and space to think about it deeply enough. I'm currently on our annual family holiday on the Aegean coast in Turkey. It's somewhere we've been coming to for years—a place where I genuinely decompress. I read, walk, swim, sail, and think. Mostly think. I believe deeply that if you're in business, you...

Every year, my family comes back to exactly the same place. Same coastline, same restaurants, same walk along the beach. My children have grown up and spent every summer holiday here. Friends often ask why we don't try somewhere new. The truth is, once you find something that works, you should probably stick with it. Sitting on the balcony this week with a coffee and a book, I was struck by how reading works exactly the same way. The books that have had the biggest impact on my life aren't...

The $2 Hot Dog and the Art of Service Excellence. Two weeks ago, I wrote to you from somewhere over the Atlantic, heading west, telling you to go and do the thing on your bucket list before life gets in the way. This week I’m writing to you having done exactly that and now home and reflecting on an epic trip to America to see the FIFA World Cup. Scotland didn’t advance from the group. But we sang ourselves hoarse in Boston and joined the Tartan Army on the beach in Miami – and my 17-year-old...

At 17, Sam Smith took on a two-week sandwich round at her grandparents' bakery in Wales. She set up her stand each morning. Worked out what people liked. Made it look better. Came back the next day and improved it again. Simply because she loved it. A month after finishing, her aunt mentioned, almost in passing, that Sam had doubled the takings during those two weeks. She didn't fully understand what that meant until years later. But looking back, it was all there: the instinct to iterate,...

A short one this week. For a good reason… I’m writing this somewhere across the Atlantic, heading to the USA for the World Cup to see my home country, Scotland, in action. By the time you read this, I'll already be in Boston, sitting in a pub somewhere near Fenway, almost certainly still hoarse from last night. Scotland played Morocco at the World Cup on Friday. I was there with my 17 year old son and a group of friends I've known since I was 12 years old – a fireman, an air traffic...