One of Tyler’s memories from his first-year high school business class was that the teacher said that back in the 1980s he had received a tip to buy Microsoft stock. The teacher said: “I didn’t move on it. Had I done so, I would be worth millions.” Tyler never forgot that lesson and since them, all he could think was: “The first tip I get, I’m all in.” 

Giacomo’s story starts just after exiting one of his successful start-ups when he took those funds, bought a 12th-century Byzantine temple in Rimini, Italy, on the Adriatic coast, hired about 20 staff and set up Black Marketing Guru. They help start-ups and industries to increase business, revenues and clicks, and views.

In thinking about his worst investment, Erik said he had lost a lot of money in a variety of ways. He did a lot of damage with a raid into crypto almost at its peak. He has done quite a few “shitty” start-up investments. But he realized that his worst investment cost a lot more than money.

In mid-2008, David left New York to work for Fidelity Investments in Boston and what followed was a very difficult first year on the job from a market point of view. The market topped out in late 2007 while a lot of stocks hit their peaks in early 2007.

It was 2006. Clayton was working for Fox News’ The Daily Buzz program in Orlando, Florida, in the United States, when he caught the real estate bug. He had lived in and fixed up a one-bedroom condo on a golf course he had bought for US$75,000 since he moved to Florida in 2004 to work on the TV show.