Chris Sacca: Highly Leveraged
How he made and lost millions while in his 20s.
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Chris Sacca is a lawyer, entrepreneur, and venture capitalist known for his appearances on ABC’s Shark Tank.
Much of his wealth initially came from a $25k investment in Twitter back when the company had just barely 100 users in 2006. Most don’t know that this was about all the money Sacca had to his name.
Here’s why.
“When things are going up it’s because you are a genius and when you're down it's because you are unlucky.”
In 1998, starting out with $10-$20k left over from college loans Chis Sacca found a loophole in online brokerages that allowed him to trade with essentially infinite leverage. Using this loophole, Sacca placed highly leveraged long positions on 1-2 stocks and turned that $10-$20k into nearly $12 million over the course of 18 months. As the dot com bubble popped, Sacca watched his paper millions turn into close to $4 million in debt.
With the dot com bubble burst and the fun squarely over, Sacca was staring down seemingly a lifetime of debt. After deciding that declaring bankruptcy would be too damaging to his career he had to just earn his way out.
“Imagine a mortgage on the biggest house that you’ll never get to own.”
Sacca eventually made his way out to Silicon Valley by way of the the law firm Fenwick and West. Sacca, who managed to scrape together a JD from Georgetown, was working at the firm during the day while doing more contract legal work at night in effort to pay off his massive debt. He worked at Fenwick and West for a year or so until he was laid off just days before 9/11.
Still with a mountain of debt, Sacca had to keep hustling, doing contract legal work, consulting and even voice acting until he finally decided to rebrand himself.
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He created a fictitious consulting firm called “The Salinger Group” which was basically just a lot of bullshit and an email address.
Now with a great business card that said we and instead of I, Sacca began to get flooded with offers for consulting work.
Sacca became the embodiment of “fake it, ‘till you make it,” while the Salinger Group became a successful consulting firm.
Eventually Sacca made his way over to hold executive roles at a startup called Spidero which is where he claims to have became “lethal.”
After Spidero, Sacca obtained a role at Google which gave him the opportunity to pay off his debt and ultimately paved his way into angel investing and venture capital.
Takeaways
Staring down the pipe of $4 million in debt only to turn it around and become a billionaire is a story unlike any other. If you aren’t yet satisfied with where you are in life, remember that many of the people that you currently look up to were in similar, or in Sacca’s case, much worse situations than the one you are in when they were in their 20s.
Check out this interview that Chris Sacca did with Jason Calacanis⬇️