Tim Ferriss

Chris Sacca — How to Succeed by Living on Your Own Terms and Getting into Good Trouble (#790)

“I’m starting to believe more and more that trouble is actually one of those things that informs all the other things that we do.”
— Chris Sacca

Chris Sacca is the co-founder of Lowercarbon Capital and manages a portfolio of countless startups in energy, industrial materials, and carbon removal. If it’s unf**king the planet, he’s probably working on it. Previously, Chris founded Lowercase Capital, one of history’s most successful funds ever, primarily known for its very early investments in companies like Twitter, Uber, Instagram, Twilio, Docker, Optimizely, Blue Bottle Coffee, and Stripe. But you might just know him as the guy who wore those ridiculous cowboy shirts for a few seasons of Shark Tank

To purchase Chris’s ranch, schedule a viewing at FivePondsRanch.com.

Please enjoy!

P.S. This episode features a special, one-of-a-kind introduction that Chris recorded of yours truly. 🙂

Listen to the episode on Apple PodcastsSpotifyOvercastPodcast AddictPocket CastsCastboxYouTube MusicAmazon MusicAudible, or on your favorite podcast platform. The transcript of this episode can be found here. Transcripts of all episodes can be found here.

#790: Chris Sacca — How to Succeed by Living on Your Own Terms and Getting Into Good Trouble

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Want to hear the first time Chris Sacca was on this show? Listen to our conversation here, in which we discussed early-stage investing advice, traits of successful founders, two differentiators that shifted the nature of Chris’ business, what Chris looks for when hiring, and much more.

What was your favorite quote or lesson from this episode? Please let me know in the comments.

SELECTED LINKS FROM THE EPISODE

  • Connect with Chris Sacca:

Website | Instagram | Five Ponds Ranch

SHOW NOTES

  • [00:06:47] Chris introduces me.
  • [00:11:07] Some Sacca background.
  • [00:18:32] Raising pre-teen gamblers and tailgating troublemakers.
  • [00:19:54] Conscious changes and rethoughts since our first interview.
  • [00:26:12] The personal and professional influence of Rich and Sarah Barton.
  • [00:30:18] Property management and the Zen of Kevin Rose.
  • [00:35:12] Zillow Gone Wild.
  • [00:36:58] Simplifications.
  • [00:45:03] Remaining optimistic despite being in the business of saying no.
  • [00:51:33] Living in the finite without +1 obligations.
  • [00:56:54] “Wait, what’s hustle culture?”
  • [00:59:48] The (lack of) trouble with kids today.
  • [01:09:53] Raising kids to solve problems and eschew smartphones.
  • [01:14:15] Rawdogging? You keep using that word. I do not think it means what you think it means.
  • [01:16:05] An Andy Goldsworthy aside.
  • [01:16:30] Taking advice from R. Buckminster Fuller GPT.
  • [01:19:13] Assigned reading.
  • [01:20:10] Humans vs. AI.
  • [01:26:20] What happens to people stuck between AI job displacement and a broken social contract?
  • [01:42:38] Counting on the human craving to convene and connect.
  • [01:56:30] What kind of business would a younger Chris start today?
  • [02:00:44] The prescience of The Medium is the Massage.
  • [02:01:39] What does Lowercarbon Capital do?
  • [02:08:44] Projects Chris is most excited about.
  • [02:18:59] Youthful mischief and flim-flammery.
  • [02:24:51] The premise for Chris’ upcoming No Permanent Record.
  • [02:35:25] Cultivating the ability to face (and maybe win over) a tough crowd.
  • [02:39:19] Chris expresses some concerns about this episode.
  • [02:40:24] Recommended reading.
  • [02:45:07] A worthwhile purchase of $100 or less.
  • [02:48:03] Deez Crocs.
  • [02:50:48] Sabotaging potential dates with authenticity.
  • [02:59:11] Parting thoughts.

MORE CHRIS SACCA QUOTES FROM THE INTERVIEW

“I feel very lucky to have grown up in a place where I had opportunities to commit small misdemeanors. And I had more than one detention. I definitely appeared before the principals on many occasions. Just some light mischief.”
— Chris Sacca

“The American social contract is that if you show up, you will get yours. And when you don’t give somebody that opportunity or you take it away from them and you take that ownership away from them and you take their house or you take their store and you take their farm, then you get the pitchforks.”
— Chris Sacca

“The number one thing you can be in this business is unpredictable. … I am known as mercurial. I burn bridges. I will not hesitate to fucking fight you. I wear the stupid shirts. I don’t give a shit about much. I’ve been known to just light it on fire. And guess what? People take me seriously as a result.”
— Chris Sacca

“Most climate investing and green investing … had been basically charitable, concessionary … But we started to actually see the math change to where the unit economics of making shit in climate, making shit clean, were starting to pay off.”
— Chris Sacca

“I think the biggest danger of raising kids with privilege is that they turn out to be assholes.”
— Chris Sacca

“The shit you own does own you. Every single object, at some point, has commanded some of your attention.”
— Chris Sacca

“I’m starting to believe more and more that trouble is actually one of those things that informs all the other things that we do.”
— Chris Sacca

“It just turns out that digging up and burning old dinosaur bones is fucking expensive, and using the sun to power the economy is just fucking cheaper. And that’s not a political statement.”
— Chris Sacca

“Clean, abundant power that is almost free is single digit years away, so that’s fucking great. I don’t even bother fighting with the oil and gas people. It doesn’t fucking matter. In fact, I actually want them to work with us more on carbon capture and sequester, putting more carbon back into the ground. Because they’ve got the trucks and they’ve got the pipes and they’ve got the engineering know-how, and they’re great at it. And so we do a lot of work with oil and gas companies going in reverse. I don’t have political battles with those guys.”
— Chris Sacca

“When you take away agency from somebody, you back them into a corner. So now do that for all the fucking white collar employees. Do that for everyone who stayed in and did their fucking homework and went to college and took out all those fucking student loans and who feel like they have played by the rules. They are the pride and joy of their families, who actually got their degree—in some cases, a master’s degree—who saw their career path laid out for them. And now they see that their life’s work is obviated by a machine that’s just better than them this fucking fast and costs $20 a month.”
— Chris Sacca

PEOPLE MENTIONED

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Comment Rules: Remember what Fonzie was like? Cool. That's how we're gonna be — cool. Critical is fine, but if you're rude, we'll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration.)

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Larry L Johnson Jr
Larry L Johnson Jr
10 months ago

I wish you had included the people Chris Sacca mentions he follows/reads in the show notes. “No Opinion” I’m assuming is Noahpinion, pretty sure Tyler Cowen is the guy writing on Marginal Revolution. “DK Thompson” I’m having trouble finding

Mitchell Luti
Mitchell Luti
10 months ago

I suspect from the political context, Tyler Cohen referred to Brian Tyler Cohen, a popular left-wing YouTuber.

Robert Glen Fogarty
Robert Glen Fogarty
10 months ago
Reply to  Mitchell Luti

In the notes under “People Mentioned,” these are the three droids you’re looking for, Larry. 🙂

Amy Chan
Amy Chan
10 months ago

Loved this episode. Thank you.

ChrisW
ChrisW
10 months ago

Okay, this merits a comment: When you guys were talking about mullet wigs, I first thought I heard “Mullenwig” as in Matt Mullenweg. Someone should patent this. And the ad should include the words “Wherever fine wigs are sold.”

You’re welcome.

Rachel
Rachel
10 months ago
Reply to  ChrisW

ahhh hahaha! I thought he said that too! And then I couldn’t stop thinking about what a Matt Mullenwig might look like

Mary D.
Mary D.
10 months ago

Now I understand why Chris receives “legend” status. He has great insights, is so down to earth and loves his life and family. Thanks for another great episode. I’ve learned a lot.

anony
anony
10 months ago

glad to see this episode

Gita McCutcheon
Gita McCutcheon
10 months ago

This was a fun one. In Chris’s “raw dog” challenge, I am acknowledging that I usually spend any or most flight time with no screens or inputs. The longest I did this was from US to Australia and back. Everyone thought I was completely nuts. I was so happy to have total peace. ✌🏼✨🤍

Billy Partankslovich
Billy Partankslovich
10 months ago

Thanks for this podcast. I was using it to procrastinate, but it was so insipid and insulting that I turned it off and got to work on what I had been avoiding. Just what I needed.

Aric Jones
Aric Jones
10 months ago

Love the episode and what you do! I think Joel Salatin from Polyface Farm would be a great guest for the show. Some of the environmental discussions with Chris reminded me of his work.

Rugilė
Rugilė
10 months ago

Beautiful conversation. Thank you both very much.

Erik M
Erik M
10 months ago

Why is Chris pushing so hard for folks to have kids when he’s despairing about what kind of lives/careers will be there for these same kids when they’re grown? Bit of a contradiction here. I’m in Tim’s boat, a couple years older, never married (10 yr relationship), no kids, wanting both, but am 100% torn about bringing a child into a world where AI rules and unless you’re already in the top 1%, you’re most likely going to be f’d. Tim’s kids will survive if they can’t find employment one day. Mine may not be as lucky. I’d love for Chris to explain why he wants us to be having children (other than it’s been a cool ride for him and that they’re his best friends – also not sure I agree with having your kids be your best friends, although sure, bonus) and how are these kids going to survive in an AI world? Government handouts?

Andy
Andy
10 months ago

I thought this was going to be really good and it wasn’t. The podcast meanders all over the place. Not in a good way. Chris seems to dodge most of Tim’s questions and redirects. As a conversation between two friends it’s easy to listen to. I like Chris as a speaker. Maybe 15-20 mins of useful meaningful conversation.

Al B
Al B
10 months ago
Reply to  Andy

Interesting, I loved this conversation. Want to listen to it again. I always find it fascinating that we all have such different experiences with the same content. I think the best podcasts (and I include this one) are when Tim has a relationship with the person. Seth Godwin’s, Derek Sivers, Kevin Rose, and this one come to mind.

JHS
JHS
10 months ago

Tim, all of the “fucks” were so exhausting that I couldn’t hear the information he was sharing. I listened to the whole podcast, but the language wore me out. It distracted from what he was saying. Less “fucks”, more engagement. A comment for good. Love your show!

Subbu
Subbu
10 months ago
Reply to  JHS

+1 🙂 . Tim patiently prodded Chris to try and answer what “Lower Carbon Capital” does. And probably gave up on that pursuit after a few tries. Concur on your point on Tim F — am a huge fan of the show and have gained a lot over the years!

Last edited 10 months ago by Subbu
Tom
Tom
10 months ago

The whole episode was fantastic. One of your best! “Hustle Culture” was my favorite. He is spot on and his approach to life and how he is raising his kids was super refreshing! Thanks

Carol Steinfeld
Carol Steinfeld
10 months ago

I like hearing from Chris Sacca and thanks for making this podcast—BUT let him know he has to be factual.
The claim that Sierra Club fights controlled burns and promotion of defensible space was off. They conducted public info events about both after the 2018 fires in Northern California.
It would have been so easy to check that.
And so that clouds his other comments.

Hannah Fame
Hannah Fame
10 months ago

Kids these days right? Obviously, we need the one-button phone with an AI assistant that can look things up, manage a calendar, take dictation for text/email, and a maps feature, that’s it, I can track my kid, and he can dictate a text to me. Everyone (not just kids) needs to get off these damn social apps and this is a brilliant solution. Hopefully, this would help resolve some of the isolation issues, get people interacting with each other, which then leads to skill-building through old-school conflict resolution (a punch in the face?)

Then I think Chris is right, the standards the left imposes on people to understand so many complex topics and behave accordingly is destroying everything. We need a platform for more inclusive leftist ideology where the discourse is respectful and mostly about caring for each other as a society on a planet. How are we supposed to sell being kind and open-minded when we are running around being the opposite toward anyone who thinks differently (even if it’s because they’re dumb)

Overall great episode, so relatable, I feel like I just went for drinks with old friends. 5 starssss

Andrew
Andrew
10 months ago

Great discussion; thank you both!

Did you see these two items?

Why kids need to take more risks: science reveals the benefits of wild, free play

Studies reveal how risky play can benefit child development. But encouraging it can be a challenge for parents.

https://www.nature.com/articles/d41586-024-04215-2?WT.ec_id=NATURE-20250109

And from Phil Knight’s excellent book, “Shoe Dog.”

“I hadn’t smoked a cigarette, hadn’t tried a drug. I hadn’t broken a rule, let alone a low. The 1960s were just under way, the age of rebellion, and I was the only person in America who hasn’t yet rebelled.”

Mitchell Luti
Mitchell Luti
10 months ago

Been looking forward to this since I listened to the first collab (I was late to the TimTim party, found the OG episode around 2019). Chris, if you’re looking for a great book on rabblerousing, consider reading Bill Buford’s Among the Thugs. I enjoyed raising my hand to each degenerate experience you mentioned.

I loved your comment on discussing politics in a Bozeman bar without getting popped. Keep fighting the good fight, reaching across barriers, and staying true to your roots – not a lot of blue collar mentality on the podcast, awesome to have you in the mix.

Last edited 10 months ago by Mitchell Luti
Mike Winslow
Mike Winslow
10 months ago

I think Chris is a Prophet.

Theresa Bergholz
Theresa Bergholz
10 months ago

Loved this episode and the one with Seth Godin I just listened to. I am 99% engaged and appreciative of what they and you are sharing. That makes sense considering I am the 99%. Like when Chris talked about buying land in climate safe areas… guys, we can’t work at your hospitals and schools and utility companies and restaurants if you’re buying it up. The Seth Godin moment was somewhat similar. Anyhow, you are an insightful interviewer, have a great laugh, and seem like an actually nice guy. Your team is perfection. There was one other podcast I listened to regularly until one day he made a brief, dismissive comment and punched down. Either you don’t do that or you have excellent editors.

Theresa Bergholz
Theresa Bergholz
10 months ago

PS I used to follow you on Twitter but got kicked off. I guess that’s for the best. Join us at BlueSky!

John Clemons
John Clemons
10 months ago

I actually enjoyed this episode quite a bit. I do think Chris is being hypocritical when he loves to talk about all the data, he has to back up his climate change agenda, and he simply ignores the data when it comes to living together before marriage and how the statistics are clear that the divorce rate is higher than those who do not live together. I think he has a lot of insight, but it is hard to take him seriously when he doesn’t look at everything honestly and objectively.

Michael S
Michael S
10 months ago

I would be very curious to know Chris and Tim’s thoughts on WHY people should be having kids. It came up specifically related to Japan and Korea. Obviously, there is the cultural preservation component to ensure your entire country doesn’t cease to exist. However, with Chris’s focus on the environment, couldn’t there be an argument that not having children could be better for the planet by reducing the strain placed on all its resources?

David Pierson
David Pierson
10 months ago

In regards to Bourdain, always liked his TV and writing, but man, did he screw when it came to that Asia woman, I wrote on Medium, he should have put the Stones Let It Loose on repeat, great song about heartache and pain when a woman screws you, got plastered, woke up the next morning, shined her out of his life and got on with living.. cheers David

Brian Crotty
Brian Crotty
10 months ago

In this episode you made a couple references to Dune. I am rereading the series now and thinking alot about why the Duncan Idaho is brought to the forefront, in particular because he represents unpredictability and free-choice. That is what the Tyrant needed to retain humanity and what Chris recommends to retain innovation in the investment and innovation spaces. I couldn’t agree more and heard it over and over in this conversation. Thank you – was very interesting and a healthy dose of impertinence with a push forward with personal drive is exactly the right combination. Thanks as always to you both.

Justin Trefgarne
Justin Trefgarne
10 months ago

This show is the great oasis I crave, and this episode is yet another massive rehydration at that oasis. Sorry for the clumsy metaphor. I admire Tim Ferriss so much. He just steers the path, and it’s a miracle he’s protected himself from being siloed in the culture war that’s gobbled up so many other podcasters. (Tim is much more than a podcaster obviously). Anyway, what absolutely seals the deal for me is the quality of the show notes. They are peerless. But then again, so is Tim. Yes I love this show.

Justin Trefgarne
Justin Trefgarne
10 months ago

I’m adding one more specific comment. I am considering a move from London to rural Switzerland. And everything Chris says about community, smartphones etc rings true to me. Nagging question for me is what is going to fund me (I am a screenwriter and director) if the robots take over. I know I may have to reskill. I’ll never, ever stop writing, but to put bread on the table, I may have to pivot. But to what?

Ryan Poole
Ryan Poole
10 months ago

Hopefully I’m going to get myself into the “good trouble” with this comment..

I’ve been working on something that might be right up your alley—a bit futuristic, a bit absurd, and just this side of illegal 😅

It’s an experiment in AI authorship and creativity. I spent the past year refining a project that takes what GPT knows and pushes it to places it probably shouldn’t go.

Would love to hear your thoughts—want to see what AI you had to say?

Last edited 10 months ago by Ryan Poole
Fred Siegman
Fred Siegman
10 months ago

Chris needs to read your book, The 4-Hour Workweek! It will give him 66 extra hours every week.

Maria
Maria
10 months ago

This guy! It’s so refreshing to hear someone share everything that crosses his mind without any filters. Not even for the fucks he doesn’t give! I’m from Europe, we still have some of the “politically incorrect” shit slip.
Thank you for letting him talk over 3h! It wasn’t an easy one for you Tim, too. To keep him on track and get your questions in, so kudos for that!
I sent it to all my friends already, especially the ones with kids. I have very similar observations about kids. Not to mention all the AI stuff – scary but I see it the same. In 2 years the world may change in an unrecognizable way.
PS. I just wanted to tell you (hope you read it) that I tried to help you with your family project a couple of times. Inviting you for a coffee when in Austin was one of those intents but of course, not an easy task to get your attention. So, I resorted to calling you an “asshole” and giving up. And then I thought about writing here lol…

JDH
JDH
10 months ago

As an experiment I am trying to get AI to pull out every book mentioned during this episode – even a few requests deep using the transcript (which I had to go find for it manually). Bots aren’t able to do it yet after testing three major models who should be half decent with research/analysis. So I am going to go back through, manually, with my real honest-to-goodness ears. I’m happy I get to do so.

Will be interesting to try again in a year.

Great episode, so engaging and thoughtful. Best episode of a podcast I’ve listened to in ages. Thanks!

Thomas DS
Thomas DS
10 months ago

Another interesting episode, although for me personally it induced anxiety on a scale I haven’t experienced before. I became worried by mention that we as humans are incapable of grasping exponential growth/change and that we’re just a few years before the point where the ‘curve of technological advancements’ starts forming a wall straight up. When researching this further via other media it became apparent that there is a lot of polarisation concerning the topic (which is not surprising). There seems to be little in between a very bright and a very dark future. I don’t want to be catastrophising, as I have experienced that doesn’t contribute to a healthy mind. So I’m interested in ways how we as humans can actively participate in shaping the future for the better, making technology work for all of us, as opposed to just big tech companies or a relatively small group of malicious people. Thank you so much for all your content. Cheers

Natalie
Natalie
10 months ago

I hope I’m not too late to the discussion here. I have two questions for Chris and the community:

1) How do you justify your daily chats with GPT while simultaneously emphasizing the need for more humanity and analog human experiences in our day to day life? It’s so easy and convenient to strike up a convo with the robot, so inconvenient, messy, and awkward to call up a human.

2) You call out South Korea and other societies with low birth rates to get busy, but simultaneously note that there will likely be serious medical advancements in the near future that could significantly/radically lengthen the human lifespan. Maybe they’re onto something?

Miguel-Marie Maher
Miguel-Marie Maher
10 months ago

Awesome episode. At least for Gen Xer’s. I literally sat down on the floor during my workout because I was laughing so hard during Chris’ riff on our “last feral generation.”
But some of Chris’ comments about the LA fires are misleading. We too knew someone who lost their house in the Eaton fire, so we’ve been focused on the issue. To paraphrase what Chris said (minus the F-bombs): They’re expediting the rebuilding of any of the houses that burned in those areas, but you can’t make any changes to them. …we just saw a bunch of tinderboxes burn up and it’s a great opportunity to build differently. Maybe different shapes, different ventilation, etc. More concrete, more shrubbery. But no. (And this is a direct quote: “Expedited permitting, if you build the exact same fucking thing you just had. ”
This just isn’t true.
The rebuilding limitations are:

  1. No larger than 110% of the original house size.
  2. Same general foot print. Same general location on the lot.
  3. Same usage. (e.g., if it had been residential, it can’t now be commercial.
  4. Same density. (e.g., If there had been a single house on the lot, you can’t rebuild the house plus build 3 ADUs.)

I looked, and didn’t see anything on the city site saying you were forced to use the same building materials, same roof, etc. Or that you had to have the same ventilation mechanism. And there certainly wasn’t anything discussing landscaping.
Looks like you could replace a burned down rickety wood shack with a concrete bunker if you wanted. As long as it wasn’t a lot bigger.
I understand the general frustration with humans not changing building patterns. I live in rural No Cal. Lots of folk are culpable. Home owners, city permits, builders, etc.
But misrepresenting the intentions of municipal governments torn between the “FIX IT NOW” cries of folk who lost their homes and the “BUILD SMARTER” cries from us on the sidelines isn’t helpful.


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Keep exploring.