
Hanging up my spurs - gfitz
https://lowercasecapital.com/2017/04/26/hanging-up-my-spurs/
======
dmitri1981
Chris Sacca's background story is little known and he talks about it at length
with Jason Calacanis. The part about him losing millions while still at
university is as shocking as his recovery from the setback is amazing. Check
out
[https://www.youtube.com/watch?v=6VOQnK7O2To](https://www.youtube.com/watch?v=6VOQnK7O2To)

~~~
dmix
[sploiler] For those who want a TLDR of this story, here it is from his
Wikipedia:
[https://www.wikiwand.com/en/Chris_Sacca](https://www.wikiwand.com/en/Chris_Sacca)

> During law school, Sacca used his student loans to start a company which was
> unsuccessful and used what was left to start trading on the stock market. By
> leveraging trades for significant amounts (discovering a flaw in the
> software of online trading brokers)[15] he managed to turn 10–20 thousand
> dollars into 12 million dollars.[15] Eventually, when the market crashed,
> Sacca found himself in debt with a four million dollar negative balance. He
> negotiated to have it reduced to just under 3 Million and by February 2005
> it was completely repaid. [15]

[15] [http://www.financemagnates.com/forex/brokers/chris-
saccathe-...](http://www.financemagnates.com/forex/brokers/chris-
saccathe-4million-negative-balance-salinger-group-twitter/)

~~~
chickenfries
What was the flaw? Also, isn't starting a company with your student loans
illegal?

> He says he managed to graduate without attending class. In order to obtain
> class notes, he threw an annual keg party where entry required classmates to
> dump their notes in a bin.

I sure wouldn't want that guy as my lawyer.

~~~
jonwachob91
> Also, isn't starting a company with your student loans illegal?

I don't think he meant using the money he was loaned to pay for classes but
using the money the loan provides for living expenses. That money is
completely up to you to figure out what to spend it on.

I could be wrong about that though...

~~~
chickenfries
I'm not sure that federal or private loans could be used to start a company,
even if you listed that one of your "living expenses" was "starting a
company."

There isn't a lot of policing of what students use their student loan living
expenses for, but I don't think that means you're free to do whatever you want
with it legally.

Also, it's amazing how the child a doctor and a professor would be praised for
cheating the government at a grand scale while our society is busy watching
what poor people buy with EBT (food stamps) at the grocery store.

I don't find these details of Sacca's story admirable.

~~~
Spooky23
If he had flamed out, we'd probably hear a sob story about the oppression of
student loans.

~~~
redm
He could have taken the easy way out of his problems and declared bankruptcy.
I think most would have, but he paid back all his debts, the hard way; that
seems admirable to me.

------
luhn
I just started listening to the Startup podcast, which features Chris in the
first episode. He seems to be a very intelligent and talented guy while still
remaining grounded. I wish him well with his future endeavors.

Also, ten minutes after reading the article, I just realized the pun in the
name "Lowercase Capital."

~~~
arikr
What's the pun?

~~~
fortenforge
"Capital" is a synonym of "Uppercase," so the name sort of means "Lowercase
Uppercase"

------
canistr
Has anyone else noticed that a bunch of people leaving the investing
scene/liquidizing in the past year are part of the same circle? Specifically
Sacca, Tim Ferriss, and Richard Branson?

I'm certain there might be more people.

~~~
melbourne7
Well, perhaps. But Sacca is great at it. Ferriss pulled out because he's no
good at it. (Easier to be a charlatan in books rather than investing).

~~~
graeme
>Ferriss pulled out because he's no good at it. (Easier to be a charlatan in
books rather than investing).

Can you elaborate on that? He's spoken about his startup portfolio being a
disturbingly high portion of his net worth because it's grown rapidly and is
illiquid.

~~~
ReligiousFlames
That is proof of poor investing common-sense: startups, without a sensible
inbound qualification pipeline, is just about the riskiest kind of investing.
Would anyone want a foolish investor (apart from not caring situations) or
rather have a shrew investor whom can add value?

------
ryandrake
Wow, 42 years old, huh? Hard not to be a little jealous. Being pretty close to
his age, it's maddening to think that with a different roll of the dice I
might have been that person. Or I might have been unemployed and a heroin
addict in Appalachia. Life seems so random and non-deterministic.

Good on him. I sometimes wonder why more people who are insanely rich don't
just retire and spend the rest of their lives doing something else...or doing
nothing. I think of the C-level execs in my own company--they each have so
much that they and their families for generations could literally do nothing
for the rest of their lives and still continue to get richer via interest. Why
go on working?

~~~
vacri
> _Why go on working?_

Money isn't everything.

~~~
badpenny
And, conversely, to some people money is everything and they can never have
enough of it.

------
jtraffic
It's interesting to think about this decision in the context of Nassim Taleb's
writing. If you have a large sample of investors, some of them would be good
just by chance. It's possible that Chris Sacca is not good just by chance, but
we can't really know, and that is an excellent feature of walking away at this
point. Most people will just tell themselves that Sacca "beat the game" and
left. It could easily be that he got super lucky and realized it.

~~~
oxryly1
True, and the only way to know more about the quality of his decision-making
is to wait another 20 years and see where he's at.

~~~
tyrust
If he is as successful as he sounds he has probably liquidated enough to last
for far more than 20 years.

------
padobson
tldr - compulsive gambler who won the Twitter lottery vows to quit playing the
lottery and move on to making podcasts and buying political influence

~~~
tommynicholas
Chris won the Twitter lottery.... and the Uber lottery.... and the Instagram
lottery..... and a bunch of other lotteries. Had arguably the best run of seed
investing in history.

~~~
socrates1998
Is there proof he got in early on all these and made money?

I think it's been pretty established he got in super early on Twitter and made
a ton of money, but I don't know about the Uber or Instagram.

I sound like a hater, but just because you "invested in" those companies
doesn't mean you made money or were a smart investor.

~~~
tommynicholas
1\. He only invests early, so yes. 2\. His fund for those investments went
213x

[http://fortune.com/2015/01/08/exclusive-is-this-the-best-
per...](http://fortune.com/2015/01/08/exclusive-is-this-the-best-performing-
vc-fund-ever/)

Possibly the best VC fund of all time.

------
angersock
_> As a rich white guy, being an activist/loudmouth in the #resistance often
means taking up political positions that are against my own apparent self-
interest. These oppressive zealots in the White House..._

 _> You mean beyond fighting a despotic regime..._

 _> I assure you, that’s not going to happen. Nevertheless, I am spending a
great deal of time meeting with all of the beautifully spontaneous and
decentralized organizations that have been popping up in the wake of our
electoral calamity as well as dozens of candidates at all levels of
government. I find so much hope in the new wave of leaders and builders who
are standing up during these times and I want to be there to support them. I
will have more to say about this in the days ahead, but, you know the drill._

I'm sure that this is a common sentiment out in the Valley, but it's really
kinda distressing to see people with access to so much capital writing with
such melodrama.

There's so much wrong at the local level--homelessness, education, people
broke with medical problems--and yet these folks seem a lot more concerned
with a strawman oppression.

~~~
Thrillington
With most people, I'd agree with you that local engagement would be more
effective. Doubly so in the homeless hating bay area.

However, Chris' access to capital, which equates to power in America, makes it
more successful for him to fight on the federal level. trump in the white
house has emboldened local behavior that threatens our education/healthcare
systems, the homeless and countless other social safety net related issues.
There are plenty of us left who can bring the fight on the local level. I'm
coming around to the idea that winning the larger fights is also important.

I've not heard of Chris Sacca before reading this article. He appears to be
that rare person with an understanding of the social obligations of wealth and
the means to build some larger communities around that.

~~~
angersock
I'm unconvinced that somebody who made their money in many cases exploiting
the little guy (
[https://lowercasecapital.com/posse/](https://lowercasecapital.com/posse/) )
is suddenly finding religion here in any meaningful way.

Action at the large levels is remote and indistinct, and boils down to status
signalling and rich people games.

Paying for housing and food and shelter and schooling and grants and libraries
and hospitals goes a hell of a lot farther...just see the good works of
Carnegie and Kaiser, to name two.

Here's an interesting read you may enjoy along similar lines:
[https://www.theatlantic.com/politics/archive/2016/10/how-
dem...](https://www.theatlantic.com/politics/archive/2016/10/how-democrats-
killed-their-populist-soul/504710/?single_page=true)

------
pdog
"As fate would have it, Jay's status appears to be at an all-time high,
perfect time to say goodbye."

[https://genius.com/Jay-z-encore-lyrics](https://genius.com/Jay-z-encore-
lyrics)

~~~
thesmallestcat
That retirement lasted all of what, a month?

------
jpeg_hero
This looks like a really easy marker that we've topped out on unicorn/big
secondary market.

When the smart big players start to take their chips off the table you can be
sure this thing has peaked.

~~~
ryanSrich
These types of comments are always hilarious. Really? You think we've topped
out on 1bn dollar companies in the year 2017? AI, Self Driving Cars,
Improvements to Flying, SPACE!? You honestly think there's nothing left to
invest in?

~~~
sbierwagen
Useful AI and SAE 5 cars are multiple years away, and this leg of the business
cycle is already 9 years old.

As for the other two categories, only SpaceX is relevant in the spacelaunch
world, and I don't think they're going public anytime soon. I don't know of
any startups that I would say have a decent chance in commercial aviation.

~~~
ghaff
"Useful AI" is vague enough that you can probably make any sort of statement
about it. If you mean things like an Echo that can take "understand" and take
actions on the level of a slightly dull personal assistant, you're probably
right. (Which is at least correlated with SAE 5.)

Of course, there's all sorts of machine learning and related AI-ish things
that are potentially useful in the interim.

Fully agree on the other points.

~~~
rhizome
The Amazon Echo having a 60-item case statement is not how "AI" is typically
promoted.

~~~
ghaff
You may have misunderstood my point. I'm saying that being able to interact
with a digital assistant (I only used Echo as an example) the way I would with
a human admin and have it take appropriate actions is many years away. It
would be an interesting application for many of us, but it's not close.

~~~
rhizome
I agree that it is many years away.

------
downandout
The problem I have seen play out with friends that have tons of relatively
easy money fall into their laps is that it saps ambition. Waking up every
morning knowing that you have enough money for a hundred lifetimes can be
freeing, but also means that you aren't _required_ to do anything at all. Many
people in that situation choose exactly that.

My understanding is that Chris isn't the nicest guy in the world, so perhaps
he's doing entrepreneurs a favor by backing other VC's. Some of his capital
will still be out backing startups, but their founders won't have to put up
with him personally.

------
winter_blue
_> I am spending a great deal of time meeting with all of the beautifully
spontaneous and decentralized organizations that have been popping up in the
wake of our electoral calamity as well as dozens of candidates at all levels
of government._

Does anyone know where (or how) to find these organizations?

I'd love to get involved in some of these organizations that are trying to
build a better future for our country, and try to contribute/help in any way
that I can.

~~~
jmcgough
[https://www.indivisibleguide.com/act-
locally/](https://www.indivisibleguide.com/act-locally/)

------
jakelarkin
the 2010-2015 era of generous outcomes for early-stage startups is over. No
more easy follow-on rounds or acquisitions. Being VC becomes a lot harder so
all these non-institutional personality guys - Sacca, Tim Ferris, Ashton
Kutcher, and Russ Hanneman types are going to move on.

~~~
s73ver
Well, Russ Hanneman is already in the Three Comma club, so he doesn't need to
that much.

~~~
snarf
If Forbes is accurate, then so is Sacca, although I imagine some non-trivial
amount of that is in Uber, which is facing downward pressure on its private
market valuation.

------
sremani
A very nice write up ruined by very partisan ramblings in the end. There is
nothing wrong in believing in liberal cause, but to consider the other side as
devil incarnate is a bit disturbing.

~~~
exclusiv
It's very disturbing but it's a leftist thing, not a liberal thing. Based on
what he writes, he's a leftist. How productive can any conversation be when
you have such a backwards and unfair starting point that the other side is
evil? Leftists also assume minorities can't do certain things and that only
they can save them because they are the enlightened ones. Leftists are far
removed from being progressive and tolerant.

I've noticed that my liberal friends have even gravitated toward this leftist
propaganda that the other side is made up of bad people. It's part of their
core and part of their strategy to divide and conquer. If the other side is
made of bad people - then your side will never leave you. In fact they won't
even engage in discussion with opposing viewpoints.

~~~
hsod
The problem with your worldview is it leaves you totally unprepared for the
scenario when the other side genuinely elects an evil or destructive person.
It presumes there's always a rough moral equality between the two sides.

We have historical examples of evil and destructive regimes being legitimately
elected. It's not impossible.

Sacca claims we are observing another example, right now, in America.

~~~
anthuswilliams
I don't think it presumes there is moral equality at all. Rather, it's
perfectly possible for an evil and destructive regime to be elected by
misinformed or desperate people, and you might be wrong about voters' motives
when you assume that they voted the way they did out of pure hatred and
malice.

------
theprop
Fantastic!! I feel that one feels most alive when you're involved in some
struggle. And if you've really achieved a high level of excellence in your
field...may be the right time to trying something new! Michael Jordan tried
baseball!

That said, I feel getting involved in political issues is mostly a losing
situation because your power (even the power of the president as we've seen
perhaps thankfully in the past 90 days is highly limited) to get something
accomplished is so limited. Also, the solution to most problems is not new
laws or new politics. I remember a professor at my college spent years getting
the exam dates shifted three days earlier from a Tuesday to a Friday...that's
the speed & work of politics, frustrating.

------
brianzelip
Always loved this website design whenever links to it get shared here.

------
animex
I think he's hinting at something political but not running for office. I'm
guessing some sort of involvement in the 2020 Presidential Campaign for some
Dem or Alt candidate.

------
forgottenacc57
Wish I was hanging up my spurs.

------
lacampbell
I didn't know venture capitalists had to wear spurs.

~~~
forgottenacc57
Yes to ride their entrepreneurs.

~~~
lacampbell
Something about describing your retirement as "hanging up my spurs" bothers me
on an unreasonable level. Unless you actually were a cowboy. I mean when I
retire from IT work I hope I'm not going to tell people I'm "stowing away my
space helmet and locking my plasma rifles in the cabinet".

~~~
cthalupa
It's an English idiom meaning to retire.

I don't really understand why this is so objectionable.

------
gtallen1187
Beautifully written, thank you Chris!

------
brilliantcode
So smart money is leaving startup/VC/SV...it'd be interesting to see who's
been swimming naked all these years when the bubble bursts this Fall

edit: oooh, definitely a touchy subject around here ;)

~~~
mahyarm
I thought the bubble was going to 'burst' in 2012. I also thought the
Vancouver RE market was going to burst 10 years ago too in 2007. And it still
hasn't burst, it just flatlined and then kept on going.

Bubble prediction is a difficult game to play.

~~~
brilliantcode
Fair enough. But this year is the perfect recipe. Trump, China, EU etc....

Read Antifragile book

------
ghaff
>no better way to create technology than startups

How did the Koolaid taste? You certainly must have drunk enough of it.

~~~
staunch
Yes, I believe in this whole technology "koolaid" thing. I'm sure you don't
use anything created by startups in your daily life, like products from
Google, Apple, Microsoft, Facebook, Twitter, Reddit, YouTube, Tesla, Ford,
Amazon, etc.

~~~
ghaff
Apple and Google are startups now? Only in the sense that pretty much every
company in existence was a startup (in the broadest sense of the word) once.

~~~
staunch
Yes, exactly. You don't get the output of a big Apple or Google without them
existing initially as startups.

Mark Markkula funded Apple.

Andy Bechtolsheim funded Google.

These didn't happen by accident. They weren't inevitable.

~~~
ghaff
Yes. And pretty much _every_ product and service I use on a day to day basis
was created by a company that was once small and may have received outside
investment even if only friends and family. And just about every product and
service has some technology component or innovation that differentiates
itself.

But now you're just arguing that companies build the products we use and
companies start small which, while overwhelmingly true, is hardly a statement
about the output of _technology startups_ specifically.

~~~
sillysaurus3
pg answered your questions conclusively in
[http://www.paulgraham.com/growth.html](http://www.paulgraham.com/growth.html)

------
gfitz
Name another VC that wears spurs

~~~
Judgmentality
Sometimes I think people in the Valley don't realize they live in a microcosm.
I had never heard of Chris Sacca before Shark Tank, and I've raised venture
capital in the Bay Area before.

~~~
fao_
I had never heard of Shark Tank, or any of the people mentioned so far in this
thread until I stumbled upon a mispost somewhere on Hacker News. I don't get
why people would watch that. The investors came off as idiots.

~~~
Clownshoesms
Hadn't heard of it either. Sounds like a very greedy guy that just has to blog
about his trials and tribulations, and explain just how his greed is actually
"drive" and "working hard". This VC kowtowing is sickening.

------
kevinmannix
Chris Sacca is one of the few VCs that people outside of the SV bubble and
even the tech world know and associate with the valley.

He, along with Mark Cuban & potentially a few others will likely be part of
the few of this era remembered many decades from now when history gets
consolidated into a few figures, much like Gordon Moore of Intel & William
Shockley of the Mountain View of the 1950's.

~~~
jacquesm
Mark Cuban got rich of _one_ deal that probably shouldn't have happened in the
first place. He got very lucky.

~~~
ryanSrich
Anyone can get it. The hard part is keeping it. Cuban has made solid choices.

~~~
ebbv
> Anyone can get it.

Please get me a couple billion dollars if it's so easy. Thanks.

~~~
softawre
It's like saying "anyone can win the lottery".

------
staunch
He's in the extremely privileged position to fund ten thousand people's
potentially world-changing dreams. Instead, he's going to squander it
podcasting in his pajamas.

We need someone with the ambition Paul Graham had when he launched Y
Combinator.

Silicon Valley is still not a meritocracy. There are still tens of thousands
of ambitious people not receiving funding. There's still no way for the early
users of massive products to buy equity and lift themselves from the lower
class.

There is no greater lever in the world than technology, no better way to
create technology than startups, and no more sure way to create great startups
than by funding them.

~~~
kohanz
> He's in the extremely privileged position...

When you achieve a position by working very hard and risking nearly everything
you have, I wouldn't consider that a "privilege". He earned the right to do
whatever he wants.

~~~
s73ver
I can easily find a dozen or so people who work just as hard, and are nowhere
near as successful. While I won't discount what he achieved, privilege is
definitely the right word.

~~~
kohanz
I think "fortunate" is a more appropriate description. Of course part of his
journey was luck and those other people have not been as fortunate.
"Privelege" is generally something that is granted to you by another entity.

