30 for 30: Big Shot

One of the recent Tycoon Playbook enrollees tipped me off to this program last week. If you’re fascinated by deal-making and enjoy good caper flicks as well, you should get a kick out of this.

Pretend that it’s 1996 and you’re a 32-year-old businessman who’s just discovered that the once mighty New York Islanders are up for sale. The price tag is $165 million. It’s been your dream ever since you were a boy to one day own a major sports franchise. Nothing says that you have made it in America louder than ownership of an NFL, NHL, MLB, or NBA team. The only problem is that your net worth is just south of $200,000 which means that, in theory at least, you shouldn’t have a hope in hell of being taken seriously by anyone.

So what do you do? Most people would pass on the opportunity because an exercise in futility is just that, an exercise in futility. So why embarrass yourself?

Continue reading →