Chris Sacca is known today as an extremely successful venture capitalist, with stakes in Instagram, Kickstarter, Uber, Twitter, and dozens of other prominent startups. What’s less well known is the story that started his incredible journey, involving millions of dollars made and millions lost on the back of recklessly invested student loans.

Having succeeded in school his entire life but having no idea what he should do with his life, Chris took the natural step of going to law school. He quickly realized two things: Going to law school classes is entirely optional, and when the government sends you a student loan check, it’s possible to use that money for day trading.

Chris hit the stock market in 1998 and invested in several of the hottest tech stocks of the decade. Not only did he invest the bulk of his student loans, but he found loopholes in the terms and conditions of day trading platforms at the time that allowed him to leverage it thousands of times over. Sacca turned what we can only assume was tens of thousands of dollars in borrowed money into $12 million by 2000.

At this point, the still unsophisticated investor got caught up in the realities of human nature that make people attribute their successes to their personal genius while attributing failures to bad luck. In reality, he says, the exact opposite is the case. A very real consequence of this, was that it never occurred to Sacca to take profits. Instead, he continued to double down and did so with very little diversification.

Everyone can guess what happened next. Several of Chris’ stocks quickly plummeted with the declining stock market, and he found his paper net worth had fallen to $2 million in short order. Dejected and on the advice of some “stoner friends,” he decided to take a break and clear his mind, walking away from trading for several weeks.

While Sacca was traveling in Austria and not paying attention to the financial news, an off the cuff remark by Bill Clinton and Tony Blair in a joint policy speech tanked the remainder of his portfolio. The politicians torpedoed the notion of patents around genetic technology, which was core to his portfolio.

Given the extent of the margin he had taken to borrow stock, Chris was immediately $4 million in debt and had no means of paying it back. Nonetheless, he refused to declare bankruptcy and negotiated a workout plan with his creditors which reduced his total debt to $2.125 million.

Over the next five years Sacca completed law school, and got his hustle on. He “sold his soul” to a Silicon Valley law firm, from which he got fired 13 months later, and then took a few personal marketing and branding liberties to started his own consultancy. The journey took him through writing terms and conditions for online adult sites and a variety of other less than impressive tasks.

Remarkably, he managed to pay down the two-plus million dollars in debt at some point in 2005, so much so that he ultimately got a check back from Sallie Mae, when he overpaid his final payment by $28 and change. He never cashed that check, instead hanging it on his fridge as a reminder that, for once, the education lender was the one who owed him money.

The rest of Sacca’s journey, including stops at Google and his first angel investments in PhotoBucket and Twitter, are much better known. What few realize, however is that his success today very nearly didn’t happen. It was his tenacity and refusal to quit, even when reckless at times, that paved his road to becoming one of the most respected and successful angels in Silicon Valley.