Chris Sacca of Lowercase Capital - TWiST

Chris's interview was so incredible that we couldn't contain it in just one episode, so today is only part one--you'll have to check back soon for part two!
1:00 Welcome everyone! Today on TWiST we have Chris Sacca of Lowercase Capital.
2:30 Thank you to Hiscox for supporting the show. Everyone go to hiscoxusa.com/smallbiz to get a free quote online in less than 15 minutes.
5:00 Chris, welcome to the show.
6:15 What is it that you do on a daily basis?
9:15 Chris: There's a lot of garbage getting funded today.
10:00 What does it mean to be a founder in your book?
12:15 Is fearlessness a good trait?
14:45 Has it become too easy to become a founder?
19:15 How did you wind up being an investor in companies like Facebook, Twitter and Uber?
20:00 Chris shares the story of how he found himself in a huge financial hole.
25:30 Thank you to Stamps.com for their support of the show! Everyone go to stamps.com and use the code TWIST for your free, 4-week trial.
28:15 Chris resumes his story of how he gambled and lost big.
29:45 What happens when people come to collect on the debt?
34:30 What was Speedera's business?
35:00 How did you land at Google?
38:15 Chris: My first angel investment was in Photobucket.
40:00 Is it right that you once took over on the secondary market for most Twitter shares?
44:30 True or false: people in the Valley tend to be like "dude, I got you,"--until the money comes in.
47:45 Has VC behavior gotten better or worse in the last decade?
50:30 Tell me about Garrett Camp of Stumbleupon.
51:45 Twitter, some would say, is screwing over the developers that helped build it. What's your take on that?
1:00:00 Are you slowing down on angel investing right now?
1:01:45 Chris reveals the existence of the fund Lowercase Stampede.
1:03:30 What gives you the ability to look at a new space with fresh eyes?
1:05:30 How did you get involved in Hollywood?
1:07:00 What do you think the impact of Kickstarter is on the entertainment business?
1:10:15 This concludes part one of Jason's interview with Chris. Party two is coming soon--stay tuned!
Support This Week in Startups and independent media by joining the TWiST Producer Program at TwistList.co!
Want to support TWiST another way? Use bit.ly/twistamazon when you shop and a portion of your purchase will go toward helping keep independent media like TWiST on air!
Keep up with the latest from our sister company, LAUNCH:
Google's Fiber 'Proof of Concept' is Anything But
www.launch.co/blog/googles-fib...
Good to Great to Excellent: A Roadmap
www.launch.co/blog/good-to-gre...
Building a Better Techmeme
www.launch.co/blog/building-a-...
LAUNCH Looking for an Awesome Full Stack Engineer/Developer
www.launch.co/blog/launch-look...
Live Blogging LAUNCH Education & Kids - Day Two
www.launch.co/blog/live-bloggi...
FOLLOW ON TWITTER
Jason: @jason
Chris: @sacca
Hiscox: @hiscoxsmallbiz
Stamps.com: @stampscom

[@essentialdang]

Someone needs to make a movie about Chris Saccas life, it's such an amazing story

[@devt0n]

+invalidusername Have you seen the 4 hour (!) Fireside Chat with Mr. Sacca. Available here on YT by Pandodaily. Super interesting.

[@essentialdang]

+Martin Iwanowski I haven't, thanks for that I'll check it out!

[@devt0n]

+Saan Saelee I second that, though I haven't seen "the lost interview" :). I need to correct myself however. I recently revisited the interview and noticed it was closer to 3 hours, not 4 like I previously thought.

[@paparangipirini8443]

Plug = Fortafy 🐐

[@dharamsochfulcafe8999]

I was 21 when this episode was recorded, today it is making an addition in my thing. Thanks, Jason and TWIS.

[@pngoc256]

I'm digging up all interviews, articles, and blog posts around Chris Sacca to learn about venture capital. And this interview is definitely one of the better ones to get the important details around Chris's journey.

[@startups]

Thank you so much Nathan.

[@azotidjr]

This is the definition of authentic content! Great interview. Thanks.

[@KShattara]

one of the best interviews ever on this show. mega informative, appreciate the effort.

[@Mr.Chatbot.]

I love Chris Sacca. What a great story. You have inspired me again, thank you.

[@SatchiCreative]

Chris Sacca is an awesome guy - looking forward to watching this one!

[@lextmb87]

"Facebook is who you used to know, Twitter is who you want to know." Brilliant. Exceptional interview. One question: this is a show for adults. Why does it have to be censored?

[@SteveWasiura]

Sacca represents Buffalo's "I can dig myself out of a snowstorm" attitude. Inspiring, get out there and hustle, fake it till you make it, deliver value and you'll be more than allright :)

[@jordanfan954]

Great interview! I've learned so much from this. My first time hearing ***** and he's awesome. Very candid!

[@ladyjedi]

Best video. I learned so much from this interview. Great content and great motivation. Very honest and informative. Thanks Jason for giving us this perspective.

[@Djvili]

Uncle Sam for the plug 🔌 Finished the Travis episode 💥

[@mecircle2012]

Amazing Story.... Loving the fact both you guys kept going and there is a part 2!

[@MrJcomp22]

Epic interview. Only thing that might top it is kimdotcom as someone mentioned below. Please get him on Jason! Honestly an internet pioneer.

[@MoneyFIC]

Where's part 2? Best episode for a long time. I've actually watched it twice in a week!!!

[@pradeepkamasani3355]

Great Story and Lots of ups and downs.So hey guys are we ready for these risks? I dont think so..very very few !!

[@mixcocam]

It's amazing that this exists.

[@bgpage24]

Sacca. Like a boss! Great interview.

[@psabdulai]

jason ur tha man people talk shit about u but ur the only one helping and inspiring a lost generation thanks.

[@SatchiCreative]

Has Chris's 2nd fund 'stampied' I think pronounced got a website? TY around 1:01

[@Younessss_]

Legendary interview

[@thunderwh]

Loved the show! Btw, Jason, I think your email newsletter needs more love. I'd love to hear more from you in my inbox. Beats that 140 character platform for birds, in my opinion.

[@williamoliver8000]

Brilliant interview. Loving this.

[@immortaltq]

This episode definitely delivered and made up for a few recently weak ones. Life must be awesome when you are Jason C. and personally know all these outstanding personalities.

[@phillelyveld]

Great video!

[@wellwrittenwords]

Great interview Jason and Chris: Thanks for sharing.

[@mneer747]

This freakin interviewer interrupts so much, so annoying!!

[@picnicxyz]

Jason Calcanis the goat fym

[@HoosierHacker]

What a story!

[@cme2go]

Jason, Awesome, One of your top three!

[@BrendanMetcalfe]

This video was a major inspiration for me

[@Kaludify]

Love it!! Great one

[@Sinusoid-]

The Salinger group! Chris has a hilariously amazing success story.. I like this guy.

[@NitishUpreti]

when is the part 2 coming out?

[@martymoviemaker]

Great interview. Is there an unedited version? I don't mind Chris Sacca's language.

[@jasonmcalacanis]

oh yes!! we need to get Kim on ... love that guy

[@jasonmcalacanis]

working on it!!! I think it might happen!

[@jasonmcalacanis]

thanks pal

[@wontwoonetoo]

100% managing your own psychology

[@JDS042]

swear jar? lame. For an uncensored and honest conversation with the compelling Chris Sacca go to both the Kevin Rose and Time Ferriss podcasts. Top Shelf natural conversation.

[@hstlr4577]

This is a gem 💎

[@startups]

We think so too.

[@jasonmcalacanis]

Kevin Rose is an awesome interviewer.

[@NitishUpreti]

An amazing episode! Woot!

[@JasonCalacanis]

thanks Ben.... Sacca was in rare form--except he's always like that! :-p

[@quantumpotential7639]

I'm surprised more people don't subscribe to Jason's channel. Given the amount of deep insight one can glean from all of his shows, you would think in the land of opportunity people would value this channel over just about anything else that is out here, be it sports and entertainment, politics, stupid cat videos, or whatever. I think it's a sad commentary in how the entrepreneurial spirit has been somehow drained from the average person. C'mon folks we can do better. Get your lemonade stands out there and start being Americans again. Thank you. 😊

[@SeyiTaylor]

Too amazing for one episode. You can say that again!!

[@grazihenke]

such a great opportunity to shut up and listen and yet the interviewer just can't hold himself shut for 10 seconds.

[@SpencerDailey]

Salinger Group FTW

[@luisger2]

Very cool. Perception *is* reality.

[@BryanWilson08]

Go watch the Kevin Rose / Chris Sacca interview on foundation.kr - Sacca explains how the banks had actually done some shady trading themselves and "traded for their own accounts and didn't give [chris] the best price" and they negotiated from $4m down to $2 1/8 million. The foundation interview does cover quite a bit of the same information as the TWiST interview but if you're interested it's worth a look.

[@jasonmcalacanis]

actually, it's more about the size of the itunes podcast files

[@sonnybrown4758]

That was fun

[@Okwegeddit]

Who’s here because of Sam Ratumaitavuki?

[@SCQT]

Love me some Sacca

[@FitnessChaos]

Damn very good video

[@startups]

Filip Todoroski Sacca is the best!

[@ddlszxcv]

What I don't understand is how Chris Sacca gets a $4M margin call and manages to pay it off in a few years??? He basically says he saved, worked a lot, scrimped for every penny, etc. He mentions working as a lawyer but even if he paid it off in 10 years, that's $400k/year which is still an enormous amount AND he even lost that job. I think he's hiding something....

[@ohmanny838]

Wow just wow more please

[@jasonmcalacanis]

thanks Jedi

[@jasonmcalacanis]

went to dinner with Sacca last night, so yes my life is awesome. i am a lucky bastard

[@davidpellum1221]

Jason Calacanis how did you get dinner with Chris Sacca?

[@johnhaden]

I dig that that Sacca calls a spade, a spade.... it's so frustrating to see all these wacky ideas getting funding. Then again, perhaps I'm jealous cause I'm not getting my shitty ideas funded :)

[@jasonmcalacanis]

in a week or so... we're editing.

[@sebastianwalls7001]

the interviewer needs to slow down, damn.. let him finish

[@ShawnDanielsMusic]

epic times

[@jasonmcalacanis]

thank you for saying that / f- the jayters!

[@shivangraisurana9955]

Well eLon musk has enough publicity now 😂

[@jasonmcalacanis]

because we don't want apple and youtube to give us an R rating

[@myhouse-yourhouse]

28:06

[@doprisi]

Interviewer: PLEASE DONT TALK SO MUCH AND DO NOT INTERRUPT: NEVER GONNA WATCH YOU AGAIN :) Bye. Chris yes, you, no.

[@romanmbwasi]

I wonder what he thinks about Twitter now.

[@19billdong96]

Roman Mbwasi "Twitter is the promising child who started doing drugs" from later talks

[@jasonmcalacanis]

we are trying.... please bait him with tweets

[@psabdulai]

a bloody mazinggggggggggg

[@JacobDunn]

Kevin Rose's interview with Sacca went into a lot of his past if you guys want to check it out. foundation.kr

[@_nitinsehrawat]

Oh god, why are people rooting som much in comments? It's all about how privileged he's, how much risk he could take, how he could gamble the millions on startups... dah . Sounds so silly in 2019

[@jasonmcalacanis]

xoxo

[@newyorkerik]

The Salinger Group😬😬

[@karanpuri06]

Who’s here from Velocity (iykyk)🤔

[@ElvinKaoNow]

Damn. What a way to leave it. Could of kept going instead of making another episode out of it. I mean, you make half a mill, don't have to milk the episode. LOL.

[@natnaeltekeste5305]

Look at Elon now 😂

[@dksangyoon]

What is with this interviewer...

[@manuelrocano1752]

Interviewer should speak 400% less and let the successful man talks.,

[@jasonmcalacanis]

thanks pal

[@jasonmcalacanis]

xoxo