CHRIS SACCA: Who would you say is
the most successful investor on Shark Tank? Maybe Mark Cuban or Richard Branson? Well, there’s no
question that these 2 are the richest Sharks but they’re not really successful investors,
they’re successful entrepreneurs. In fact, you could say the same thing about every single Shark
that’s ever been on Shark Tank. They all made their fortunes as entrepreneurs and investing
is something they do basically post retirement except for Chris Sacca. You see, Chris is not just
an investor for TV but an investor in real life. In fact, he was able to turn an initial investment
of $8.4 million into multiple billions by being early to Uber, Twitter, Docker, Kickstarter,
Instagram, Medium, Streak, Stripe, and Twilio just to name a few. In fact, many VC veterans describe
Chris’ fund as the best performing VC fund of all time which is not surprising given that Chris
generated an extraordinary 250x return. In other words, for every $100,000 that Chris invested,
he generated on average $25 million, but all of that only tells half the story. You see, Chris
isn’t just the most successful Shark but also the most successful Shark Tank contestant because the
initial investment wasn’t even his own money, it was actually other people’s money. Essentially,
he convinced other Sharks to give him a crap load of money so that he could go out and be
a shark himself. Aka, Chris’ entire career is playing both sides of Shark Tank and he became
a billionaire doing that. This isn’t to say that Chris is the most successful business person on
Shark Tank but he’s by far the most successful investor and investee. But it wasn’t always like
this. Before getting into VC, Chris was actually a lawyer and early Google employee. And before that,
Chris was personally underwater by $4 million by being the world’s first degenerate Robinhood
Wall Street Better. So, here’s how Chris Sacca got rich after all that and why
he’s arguably the most successful investor not just in Shark Tank history but in VC history.
LOSING IT ALL: Taking a look back,
Chris’ story takes us back to May 12, 1975 to a suburb of Buffalo, New York called Lockport. Chris
was born to an upper middle class family. His mother was a professor at the local university,
SUNY Buffalo State, and his father was an attorney. From a very young age,
Chris’ parents pushed him to always be curious and search for answers. In fact,
Chris would regularly be pulled out of school to go to science museums and book readings. Hearing
this, I don’t think you’d be surprised to hear that Chris would eventually make it
into Georgetown University, one of the most prestigious law schools in the world. There,
he would earn a bachelors in Foreign Service and a law degree, graduating cum laude both times. But,
honestly, graduating was the least notable part about Chris’ college journey. It seems that
despite being led in this academic direction, Chris always had a calling for investing,
and let’s just say he really leaned into that. If you follow the modern investing community,
you’re probably familiar with the infamous Reddit group: Wall Street Bets. These guys are the self
proclaimed degenerate investors behind investments like GameStop, AMC, and Dogecoin. Chris would’ve
fit perfectly into this community because he was doing the exact same thing just during
the 1990s. You see, Chris didn’t have any money, so he would start trading with his student loan
money of $10-20,000. Already a pretty stupid idea but Chris would turn up the risk 100X from there
using margin trading. If you’re not familiar with margin trading, it’s when you borrow money from
your brokerage to trade using your deposits as collateral. So, essentially, Chris was borrowing
money on borrowed money, but it get’s even worse. You see, brokerages will only lend you so much
margin for obvious reasons. They want to make sure that neither of you end up with losses that you
can’t afford, but this was in the 1990s and online brokerages were just starting to be built up,
meaning that there were some loopholes in the code that calculated margin. Essentially, if you close
trades before they settle, which takes 3 days, you could bypass the margin requirements. Fun fact,
Robinhood would have a similar glitch over 2 decades later. But anyway, Chris figured this
out and he would soon start trading with millions of dollars worth of brokerage money even though
he personally only had $10 to $20 grand which was also borrowed money. Looks like he was a
pro at trading other people’s money from day one. And it wasn’t like Chris was investing in strong
blue chip companies either. He was investing in speculative garbage, but this was during the peak
of the dotcom bubble, so it seemed like Chris was a genius. He would turn about $300,000 worth of
borrowed money into $12 million within just 18 months. He could’ve just cashed out right then
and there and been set for the rest of his life but just like any other Wall Streets Bets degen,
Chris was always betting it all on bigger and bigger trades with margin and eventually the music
stopped playing. When the bubble burst, Chris would lose everything on just 2 stocks and before
he knew it, he owed his brokerage $4 million. This would’ve been a good time to throw in the
towel and file for bankruptcy, but Chris didn’t do that. He figured that filing for bankruptcy
would make him unhirable as a lawyer. So, instead he negotiated the balance down to $2.125 million
and embarked on likely one of the biggest repayment plans in retail investor history.
COMEBACK OF A LIFETIME: The good news was that unlike
most Wall Street Bets degens, Chris actually had a strong academic background as a lawyer. He would
find a job at a Silicon Valley law firm called Fenwick and West, but this didn’t last long.
As the dotcom bubble burst and investors pulled funding, Silicon Valley naturally pulled back hard
on their legal expenses. As such, Fenwick and West would do mass layoffs and Chris would be let go.
This was most definitely rock bottom for Chris. He was millions of dollars in debt and couldn’t
even get a job despite having a Georgetown law degree. Out of desperation, Chris would start
a solo practice, handing out business cards at every networking event he could think of,
but the response he always got was “no”. Most would’ve quit right here, but Chris had one more
trick up his sleeve. Maybe he could use Silicon Valley’s big egos to his favor. He would rebrand
himself as the Salinger Group and set up a slick website. And whenever he met potential clients,
he would describe the Salinger Group as “we” instead of “i”. And funnily enough,
this would make all the difference. All of sudden, Chris’ big ego prospects who didnt’ want to seem
ignorant would say “Oh yeah, I’ve heard of the Salinger Group” (even though that’s physically
impossible). This strategy didn’t lead to massive contracts or anything but it did bring in plenty
of consulting work for the one man shop that was the Salinger Group. Pretty soon, Chris was able
to hire his law buddies who were also out of a job and the Salinger Group became a real thing. Looks
like Chris really internalized the Silicon Valley mantra of “fake it till you make it”. Eventually,
the Salinger Group would attract the interest of Google who would hire them all out for a
top secret project: taking on Microsoft. One of the main reasons that Google was able to take on
Microsoft successfully was because they were able to fly under the radar so well, and the main guy
to thank for that was none other than Chris Sacca. His entire job was to basically mask the growth of
Google from Microsoft. He would create a bunch of LLCs and corporations that couldn’t be traced
back to Google. And these fake entities would sign data center and server contracts instead
of Google making it extremely difficult for competitors to gauge just how big Google really
was. It wasn’t till Google went public in 2004 and started publishing financial reports that
the tech industry really understood just how big of a threat Google really was. But by this point,
it was not only too late to stop Google but too late to stop Chris. The Google IPO had
blessed Chris with enough money to pay back his massive debt and finally become a free man. Also,
Chris had worked his way into the inner circle of Google becoming friends with Eric Schmidt,
Larry Page, Sergey Brin, and Sundar Pichai. Chris was actually one of the first Google
employees to ever receive the Founders’ Award which is Google highest internal
honor. This would’ve been a great time to count his lucky stars, enjoy his nice gig at Google,
and ride off into the sunset. But Chris would decide to risk it all, all over again.
RISKING IT ALL AGAIN: Instead of storing away his Google
winnings for safe keepings, Chris would decide to bet it on speculative startups and one of his
first bets was none other than Twitter. Chris was Twitter’s 102nd user and he would start off with
a reasonable investment of $25,000 in 2006. Over the next several months, he would become friends
with Twitter co founder, Evan Williams, and he basically become Twitter’s investor mascot. He
would work closely with the founding team and try his best to raise more funding for Twitter,
but no one really took Twitter seriously, so Chris decided to take matters into his
own hands. You might be thinking, maybe he used his legal expertise to structure some sort of
200 IQ funding scheme or maybe he helped Twitter fake it till they made it just like he did with
the Salinger group. But, Chris didn’t do any of that. He actually had a much simpler solution.
He would simply liquidate his entire fortune and bet it all on Twitter. I’m telling you,
this guys’ risk appetite is insane and it doesn’t even stop there. After betting his entire fortune
on Twitter, he would quit his job at Google, the last node of stability that he still had,
to pursue VC full time. And keep in mind, it’s not like he had any more money to invest anyway
given that he already bet it all on Twitter. So, he had to find the money and the investments. The
silver lining for Chris was his Google experience which gave him a lot of connnections both on the
investor side and on the entrepreneur side. He would use these connections to raise $8.4 million
in seed funding and establish Lowercase Capital in 2010. From there, Chris would go onto have one
of the best tech investing runs in history. He would invest in Uber, Instagram, Twilio, Stripe,
Kickstarter, Docker, Streak, Lookout, Medium, and dozens more. With these sorts of names, it’s
no wonder why Chris was able to generate a 250x return and become a billionaire in the process.
Despite being one of the best tech VC investors in history though, no one outside the tech community
really knew Chris until after he retired. He would of course appear on Shark Tank, but that was just
his most notable role on TV. He has since done dozens of interviews and cameos all across TV.
For example, here he is on the show Billions playing himself, a VC investor. And ironically,
this is what made him famous, not his stellar investment record. But anyway, Chris officially
retired from VC in 2017. He didn’t shut down Lowercase capital, but he did stop raising money
and investing in new startups. Since then, they’ve really just been maintaining their investments and
slowly selling off their stakes. Chris hasn’t given up investing altogether though. Instead,
he has shifted his focus to sustainable investing efforts. In 2020, for example, he launched a
climate change VC firm called Lowercarbon Capital which does exactly what you would
think. They invest in startups that are fighting climate change. Chris is also involved in a water
charity that is looking to bring clean drinking water to every person in the world. And he has
also signed the giving pledge and with that, it seems that Chris’ story has officially come full
circle. From being in debt $4 million to being in a position to donate over a billion dollars,
that is the volatile story of Chris Sacca. If you're interested in deeper dives, interviews
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