Jonathan was told to approach a certain company in a sector that he already had invested in before and did well. Since he did not want to let an opportunity pass, he met with the owners of the company and discovered that they wanted to sell the business.

John’s worst investment happened when, despite being an expert in investing, he started believing that he could time the market.

Sal as an angel investor is always looking for startups to invest in. it’s no surprise that his worst investment ever was missing out on a good deal. Sal got to learn about a company called Love Pop that makes greeting cards that open up and a magnificent sailing ship or airplane pops out.

Dustin’s worst investment ever was his first home, a condo in Florida. In Florida, back in 2007/2008, you literally could buy a piece of property, and it would go up by $100,000 or $50,000, depending on where it was.

John found himself in the middle of the internet bubble in the 90s. Being a smart investor, he’d seen the internet bubble coming, and so he got out of technology stocks. This saved his wealth and so he was sitting on his high horse as he watched others lose their investments.