Chamath Palihapitiya and Natalie discuss their California residency despite billionaire tax fears, his post-Grock sale depression, and their "red-pilled" political shift after media distrust. They detail marriage dynamics, including Natalie's communication advice and Chamath's silence, alongside high-risk biotech investments grounded by her financial oversight. The episode also features Jason Chang managing household logistics to counter disorganization, skepticism regarding Elon Musk's UFO claims, and a review of Jamie Simons' "Art Thief," concluding that successful agency requires both personal resilience and strategic partnership. [Automatically generated summary]
You went from being a large Democrat donor to now a very outspoken proponent on the other side of the aisle.
How did you get there yourself?
For me, it was an evolution where I was like, I can't believe I'm being lied to by this group of people whose sole responsibility is to hold truth to power.
That, I mean, red-pilled me, I guess, in a way.
At the end of last year, I had an incredible thing happen.
This business that I helped start 10 years ago.
Grock.
And, you know, we sold it to NVIDIA.
$20 billion.
Incredible validation.
All of this success.
Katie, I felt super like down.
Like the entire internet was celebrating you and saying Chamath must be having the best day of his life.
I have felt the happiest before something great has happened.
And then afterwards, I feel worse than before.
When you guys met, was he this outspoken about his viewpoints?
When I met him, he was very opinionated.
That was there for sure.
That meant a lot to me because it showed me what it meant to be fearless in the market of ideas.
Instead, I've always wanted to be more measured.
That's why I always win the arguments.
Hi, everyone, and welcome to this week's episode of the Katie Miller podcast.
We're so excited to be in Palo Alto today, joined by Chamoff and his beautiful wife, Natalie.
Thank you so much for doing this.
Thank you.
Thanks, Katie.
So we're sitting here in Palo Alto.
You have been incredibly outspoken in recent days about all of the wealth moving out of California.
Your home is beautiful.
Thank you.
Do you think that you guys would also too leave California if the billionaire tax passed?
I think that is our big fear.
It's sort of the nightmare.
We're kind of going through the phases of denial, acceptance, grief, however you call it.
But I mean, right now we're committed to staying and trying to show people why this is a really terrible idea.
You went from being a large Democrat donor to now a very outspoken proponent on the other side of the aisle.
When you are so influential to other VCs and other people with high net worth here in California and you've really shaped their public opinion and public perception, how did you get there yourself?
Was there a moment you woke up and you're like, okay, it's all different?
There was.
This is not about politics for me.
It's about the truth.
There was a moment where I was basically like everybody else and pretty brainwashed.
My media diet was very much the same as everybody else's.
I read the New York Times and the Wall Street Journal.
I watched a little bit of CNN, a little bit of CNBC, a little bit of MSNBC, a little bit of CBS.
Economist, every now and then you encounter it on a plane and you think you know what's going on.
And I had a perception of Donald Trump initially from the moment he walked down the staircase in Trump Tower to announce.
And then over the course of seven, six or seven years, I realized that some of those fundamental things that I was told about him were just totally false.
And there was enough content online where I was almost afraid, but it started with Charlottesville.
I was almost afraid to look at it because I'm like, I think I was lied to.
And then I saw it.
I saw what he said, but then I saw the portrayal.
I had originally believed that portrayal until I saw the truth.
And then I just started to go down that rabbit hole.
So for me, it was an evolution where I was like, I can't believe I'm being lied to by this group of people whose sole responsibility is to hold truth to power.
The key word there is truth to power, not your perception or your desires.
And I just think that that, I mean, red-pilled me, I guess, in a way.
When you guys met, was he this outspoken about his viewpoints?
Because I think most people don't know that you're an accomplished businesswoman, Natalie, amongst yourself, and that you've done a lot in your career prior to the two of you meeting.
Sure.
I love my job.
I love working, but I still think there's much more to accomplish.
So I would tone down the adjective, but thank you.
When I met him, he was very opinionated.
That was there for sure.
Sometimes, I think it's a question of instinct.
Some people just instinctively go.
And what he taught me was the capability of iteration, iteration.
When I met him, my views were softer.
Well, they still are.
I try always to keep optionality to be wrong, to weigh probabilities, to weigh out the risks.
He had no idea of what risk meant.
And that meant a lot to me because it showed me what it meant to be fearless in the market of ideas.
And in this way, I've noticed this journey.
I've noticed him change.
I've noticed him integrate a lot more of the things that were important for me, like measurement, judgment.
But he factored them in with experience instead of starting off from the idea of wanting to be right.
Instead, I've always wanted to be more measured.
That's why I always win the arguments.
How did you guys meet?
This is an incredible story.
There was a period in my life where I had a pretty traditional investment business.
And I had a pretty talented career, but there was a moment where I felt like something was missing.
And there was a person that I hired to work for me whose whole goal was to scale the business.
And the way that he perceived it was create a patina.
And he was Bill Clinton's son-in-law.
And he was a very good person and tried to do a lot with us, has gone on to be very successful at a different firm.
But he's the one that connected us.
And he said, you know, these guys are a great family.
They're based in Italy.
And she's going to be here, the CEO of the holding company.
And I was like, well, what time?
And he's like, 9 a.m.
And I was like, yeah, that's too early for me.
And then he's like, no, but listen, this is a pharma business and they're incredibly important.
I think he's a good person.
So at a certain point, Mark and I were friends and he definitely overplayed the situation.
He was like, oh, she's a very important pharma in Europe.
You know, multiplied by 10.
And Shamat was like, still no.
And then at the end of the day, he was like, look.
He was so exasperated.
She's really hot.
She's super hot.
And so he showed me, he showed him a picture of me.
And Shamat looked at the picture and said, so we did not meet.
So we did not meet.
Katie, it was really early in the morning.
It was 9 a.m.
And he's like, nobody in California, you know, you work till 2.30.
I agree.
The work culture in Palo Alto is significantly different than 2, 3, 4 a.m. in the morning.
Fair.
The before and after, I now wake him up at 5 a.m. because I work with a European business.
And so I want to start my days early.
I have to start my days early.
So those times are long past behind us.
And it's just charming.
But anyways, that's not how we met.
That's how we did not meet.
But then that night, we were both at the same restaurant.
We struck up a conversation.
She came to the office the next day.
And I had an all-glass office in Palo Alto.
Every room was all glass.
And I remember her saying, I need to leave to fly back to Italy, but can we just talk for a few minutes about some of these things that I've just learned about sitting here with you guys?
And I walked in behind her into an all-glass room and couldn't close the door.
I just looked at her and I was like, and I kind of like lost myself, became very nervous like a child.
I just kind of sat there, like nervous, like a, and, and she's like, this is really weird.
He's like acting nervously.
The door isn't closed.
But that's, that was the moment.
I didn't realize it at the time, but very subconsciously, I think that that's when I was.
So what he's missing from the narrative is that from that moment, also nothing happened for like nine more months in which he also set me up with other people.
Like when I say nothing happened, it's not that, you know, that moment gets deep into you and something really motivational shifts.
No.
And then we became friends and then we talked about everything possible and life continued.
And then many, many, many, many months later, I realized, well, actually, we had lunch together in a place and suddenly he leaves me in the middle of lunch and says, sorry, I need to go by.
And this was also sudden.
And so I was preoccupied.
Now we're talking like, I've been knowing him at that point for like six, nine months, I can't remember.
So a significant amount of time.
I'm like, what's going on?
I just got up.
We were at the Dorchester or something, Berkeley, at the Berkeley Hotel, having lunch.
And in the middle of lunch, I literally got up and I'm like, I'm feeling sick.
I must go.
Goodbye.
And I just walked out and I went to my room.
So I texted him later and I said, are you okay?
And he said, well, I really felt like I was sick.
I just needed to vomit.
And I'm like, oh, I'm so sorry.
Do you have a bug?
And he's like, no, it's like, I realize I think I like you.
It was like high school.
I was really like high school.
And I was like, it's a terrible idea.
I don't think that's accurate.
And we moved on and another month passed.
And then you guys, how long was it from that point did you end up having kids together?
Oh my God.
Well, then like a month later, we started dating.
And then, honestly, like within 10 months.
When we kissed for the first time, I think after a few months, then we kissed.
It's not clear how that happened because the idea was like, this is...
And then I moved to California for business reasons.
And seven days later, I got pregnant.
That was nine years ago, eight and a half years ago.
Well, yes.
And one of not really thinking about things twice and then ending up to be lucky.
Yeah.
Ended up working out beautifully because now you're married and have a house of five children.
It's incredible because, you know, I was coming off of a divorce.
So it was, you know, I had like zero self-confidence and self-esteem at that point.
And I also didn't know like how to be in a relationship because clearly the first time didn't work.
And so I've learned a lot from her.
It took a long time because I, you know, you're just, nobody's trained.
There's no, there's no playbook that says, here's how to be in a relationship.
And then here in Silicon Valley, it was all kind of platitudes, you know, like what it means to be in a couple that works.
And like, you know, it just, it was all BS.
So I've learned a lot actually how to do it.
It's been a negotiation for sure.
Have you brought in lessons from your last marriage into this one that you can help tell other people who are either going through a divorce or who are trying to do this again about how to make a successful marriage and relationship the second time?
Well, I mean, I think what I learned from that is there is an incredible amount that can go unsaid that must never go unsaid.
And it's like, you just got to put it all out there and talk about it.
And look, I grew up in an Asian household, right?
And so these are stoic people.
They don't say anything.
They just internalize everything.
And the anger and the resentment builds.
This one over here.
Well, me instead.
She'll throw shit, like, I mean, she's not afraid.
I think some people have warehouse where to store resentment.
I don't have that warehouse.
It's just missing.
So I give it back on the table.
And this is very, I think it's very useful if you have to deal with somebody as special as Chamachmat is truly, truly special.
He's got a very, very big heart.
But he's sometimes unaware.
He is not very, very empathetic.
Say what you really want to say.
He's dumb as hell.
No, I'm kidding.
This is like the constant thing.
She's like, you're so incredible.
She always says, you're such a genius, but you're an idiot.
No, he.
What's the dumbest thing he's ever done?
Oh, gosh.
Are you serious?
Yeah, dude.
Let's go.
Oh, God.
I would have to think about it because it's so many, like, you mean today or in the last week, I would have to focus on like a narrow window.
Hold on, what's the last super dumb thing that you did?
You did, like, what was the last time we had...
A huge fight?
Yeah.
Yeah.
We used to have these.
Like, we used to have, like, so I didn't know how to fight.
I don't know if you know how to fight, but I do.
You do know how to fight.
I do.
It's a really important thing to know how to do with your spouse.
Except my husband, and I will say this, and like, I know he'll get mad when I divulge this because he doesn't like when I divulge our personal life on air, but I make other people do it.
But no, when we fight, he typically goes quiet, which is not the interpretation that he would give off publicly, is that he does not fight back.
Yeah.
He just goes, like, he's very respectful and quiet.
And that makes me more mad and more upset.
And I think we're very similar in that.
So I don't have that.
I just came up with two things.
Okay, great.
Let's go.
Sorry, as you were talking, you inspired two things.
One is the playful thing.
So when Shamath has nothing to do, like the classic weekend, his mind is fixated on how do I get her to snap.
So he organizes traps, like organize.
He starts one day, and this can be a long con.
The whole purpose is to get me to snap and to call him by his birth name, Chamath, versus how I normally call him.
I call him Amore.
When she calls me by my name, it's like when you call your kids by their name.
They know.
They know they're, you know.
They know that you mean business.
And this is what I live for on the weekends.
If nothing's going on.
How long does it take for her to call me by my name?
And so he just wants to, what are her trigger points?
And he will start saying things that he doesn't even really want.
Like, let's say we've been out for a whole week.
We've been traveling.
We've been working late and we've been out.
I don't like to eat out too many times during the week.
It doesn't make me feel good.
I feel I lose a little bit of control over my calorie intake or sugar intake, whatever.
And he knows that for me, it's a sensitive spot.
Losing Control Over Sugar Intake00:09:16
And so he'll say, even worse, even worse, like, oh, you've heard about this incredible restaurant.
But really nice to go with our friends.
Unless you feel like, I mean, you don't have to say yes if you have psychological problems.
But otherwise, it would be really nice.
And it's like, what?
And this is like the fifth time.
And he will like say small things like, actually, I've heard this menu.
Have you ever heard about this place?
And we'll say three, four times.
Then he will invite other people on the con and it's like, hey, Mark or whatever, come home.
And then can you name this restaurant a couple of times, please, until she gets the message.
And so until I finally say, look, I've been here.
I've been doing everything you wanted all week.
We've been to four restaurants already.
Now, can we avoid this fifth?
And then I start laughing.
But when we fight seriously, he goes into silent mode, which I take as punishment.
And he doesn't need to do anything because I self-punish very well.
And he will then call me things like, you're so histrionic.
Like, it doesn't, the idea is not to say something which is really bad.
It's to say something that is so subtle that it'll haunt me for the rest of my days, even though he never thought it.
Totally, I totally appreciate this.
We fight very similarly, where finally I'll get so triggered that I will lose it.
And then the other person just sits there quietly and he was like, no, you're the one that's.
By the way, can I tell you where it comes from for me?
Where?
Like, I, you know, just growing up the way that I grew up, didn't really have a lot of friends.
Parents fought a lot.
I was always very afraid of, I don't want to be rejected by Nat.
And so I would just never, so even in a real fight, like when we're not playing around, I get very quiet because I do get in this mode of like, what if she leaves?
And I, and I get really, and then we kind of like sort it out, but it takes a while and she has to lead.
If she didn't lead, we wouldn't have resolved anything.
Normally what happens in our fights is that he gets a little insecure by a something.
Could be anything.
Could be an email, could be a tweet, could be a piece of news, anything really.
And then he feels smaller.
And so he wants to make me feel smaller and he makes me feel smaller.
And because I have different kinds of insecurities, I don't think I'm structurally insecure at all, but I will feel small.
And in those moments, I feel a little insecure for five, six minutes.
And then I think, why did he do this to me?
And so I snap back and I get mad at him.
And then I always have the responsibility to de-escalate my getting furious and understand that he's the one who's really hurt and try to unpack that with him.
So I'm like, okay, sit down.
Okay, what happened?
Tell me everything from the beginning.
Sounds like a very healthy marriage, though.
I will say that as like, it's a very healthy conversation.
I'll tell you, she has to do this a lot for me, which I think is like, it's a gift.
At the end of last year, I had an incredible thing happen.
This business that I helped start 10 years ago.
Grok.
And, you know, we sold it to NVIDIA.
$20 billion.
Incredible validation.
All of this success.
Katie, I felt super like down.
And she could feel it.
So she could feel it.
And her father felt it on the phone.
And her father says to her, he just seems like he's a little down.
And I was trying to figure out like what is going on.
And I'm like, I'm like, I said to Nat, I think I'm depressed.
And she's like, this, okay, why are you depressed?
I don't know.
You know, I think about all the things that didn't go right.
And then, you know, and she, and then she kind of like helps me navigate it to a much simpler explanation, which is like, you know, there's just a lot of other stuff going on.
And we're really in the middle of a bunch of important things that you've invested your whole life in doing.
And it just doesn't feel like you've gotten to the end of it, but you've made a lot of progress if you actually look back.
And she's like, you got to just take the win here, buddy.
Like the entire internet was celebrating you and saying, Chimoff must be having the best day of his life.
He's so drock.
He's made so much money off this initial investment.
I felt like this.
Isn't that crazy?
It is.
I think for how many people who are out here who are trying to get into venture or are investing and who only hit to hit it as big as one time as you did, could they ever be so lucky?
Yeah.
I mean, while it's so fascinating to see the flip side of that.
It's like every, like, it's weird.
Like I have felt the happiest before something great has happened, before the Facebook IPO, you know, before the Warriors won a championship, all these things that I've been lucky to be involved in, before the Slack IPO.
And then afterwards, I feel worse than before.
And now I think she's kind of, and that's been helping me kind of shape an information.
I think that the story is a little larger.
And there is a story of the single shot that people can see or assume or there's the one story.
But then Jamath has had a very wide range of stories.
So while something is more in the face of other people, there's just a lot of other stories in the background.
And those other stories might be less successful or less easy.
And even the stories that become successful, what did it take to get there?
And what is the backside story?
So I think that he said it once and it became a meme, but it's actually a good, accurate way of depicting it, which is when you're in the arena trying things, like I am in the arena trying things and he is.
So there is no space to just like wrap the whole package and say, okay, this is a judgment.
This is the end because you're in the middle and there's like five things that are broken and there's five things that need to fix, need to be fixed.
So yes, if one thing goes, it's really important to make sure that we can focus on that and make sure that that's celebrated, but that takes nothing away from all the things that instead need attention and need his constant energy and modality.
And modality is an important one because he needs to be really with his head down, just in the engineering, in the machine room, really focused.
And sometimes all of the world of X and Instagram, the world outside, sometimes gives you a sensation of being high or being low for whatever reason.
And this is what Jamatha and I try to work a lot to be shielded from because it doesn't change the everyday.
How do you handle, you know, you are so public.
You make a lot of public comments on X. How do you handle the, I would say, legacy media news machine that comes from that?
How does that affect you?
Do you guys read it?
Does it, I'm sure you're reading the negativity.
We all see it, but it's how do you handle it when it comes your way?
And how does it affect you?
Well, I'll take this because Jamath is a star in this.
He does not care.
Me, on the other hand, not so good.
So I actually look it up and I don't look it up because I want to be hurt or I want to hurt him, but because I really trust sentiments.
And sometimes if you read a lot of negative comment, I want to understand where it's coming from and divide.
Sometimes it's a lie.
Sometimes people have an idea which is based from something that is utterly untrue, 100% untrue.
But truth doesn't come in black or white.
It often comes in shades.
And so I'm always seeking for opportunities to improve.
And sometimes we talk about it and he's very definitive.
I'm like, I don't want to talk to you.
This is completely wrong.
And then slowly, slowly you can see that like a door is opening.
Do you ever tell him to delete a tweet?
Oh, God.
Oh, my God.
The funniest thing.
I'll tell this story.
I'm pretty like, I tweet what I want, or I post what I want to post.
Sure.
I've been triggered very rarely.
And then one time I got triggered by this person.
And he had been writing me.
I just couldn't and I couldn't get him off me.
And then finally, I basically called him fat and stupid.
Okay.
I said, you're fat and you're stupid.
That's what I said to his reply.
I said, you're an idiot, you're fat and you're stupid.
Something like that.
And it was like 7.45 in the morning.
And I know this because then I started my workout and I felt great.
I'm like, yes, I put this idiot in his place.
Let me go start working out.
7.46, my phone rings.
And she's like, take it down.
And I'm like, what?
She's like, I'm like, you're monitoring my posts?
She's like, no, but something in the universe told me to check Twitter.
I saw this thing.
It's unnecessary.
Calling Him Fat And Stupid00:05:43
Take it down.
And I'm like, oh, fine.
So I'm sure I didn't say that.
I'm sure I didn't say unnecessary, but yes.
That was a chance.
I don't check his tweets.
I don't, and I don't look at it often.
But sometimes, you know, when you, I don't know, you wake up and you're like, hmm.
And I think I was in a meeting, so I wouldn't normally use my phone to go somewhere else, but I had a feeling.
And that's when I checked.
And it was not good.
Yeah.
What's the smallest investment you've made back or made for a company where you felt very personally invested that did well that actually gave you that sensation that we just talked about of feeling fulfillment and joy comparatively to what I would consider a grok being a huge deal that's made you lots of money and is a giant success story and you're not feeling that same comparison joy?
I think that the tension that I've always struggled with is the things that I do aren't always the things that I think I should do.
And the latter is a bunch of high-minded ideas about how the world should just be better and more rational.
The problem is that doing those things are very difficult because the amount of money that it takes to do those things or the amount of regulatory change or the amount of other people's support is so large as to be basically for every other human being other than Elon impossible.
Okay, but what's the deal?
So I did like a breast cancer thing where a third of all breast cancer surgeries or like lumpectomies are ridden with an error, which means that if you for every 10, three women have to get another lumpectomy because they leave cancer behind.
Of those three, another one.
And so we built a machine that uses a type of imaging that is 10 to 1,000 times better.
We just got FDA approval.
It's like a very small thing.
Makes me feel like really like I've done something.
Yeah, you've done something for the world.
Yeah.
And it's technical.
It's hard.
It took us three years.
Yeah, like I like that kind of stuff.
The company actually that the basis of Starlink is a company that Elon acquired called Swarm.
And it was a guy from Apple and his co-founder, Sarah Spangelo.
We were the original capital in this thing, working out of our office, incubating these little satellites, sending them up in little planes out of Palo Alto to test them.
And then, you know, he scooped it up and it just became a huge part of Starlink.
So to see that success for them, so those kinds of things make me really happy.
Like you've changed the world.
It's like, well, I'm like a little part of it.
You know, I'm a little part of this big story.
So I'm sure when someone sees you now, you're more recognizable than you used to be ever since the podcast.
What is a successful pitch look like for somebody who comes up to you on the street?
Not who gets a meeting, who's sitting in your office and pitching you, but when you said, okay, fine, you can have my number.
The single biggest determinant of success is the agency of the person.
And the reason is that you just go through so many trials and tribulations.
I remember like before Sarah and Ben sold Swarm to SpaceX, we got a cease and desist letter from the FCC.
I mean, look, when you're a young 28-year-old founding team and not a lot of money in the bank and you get a cease and desist from the United States federal government, you basically shut down and go home.
But they didn't.
And that's an internal decision.
So the thing that I care about, oftentimes what I ask people is, tell me about how you grew up.
Tell me about your relationship with your parents.
What did your parents do?
What are your siblings like?
And all I'm trying to figure out is if there was hardship somewhere where you just had to decide, you know what, not me.
I'm going to make it.
And that's the skill.
You apply it to any market.
That person is more likely to be successful than in the most obvious market.
That's the successful pitch.
It's just that sense of like this MFer is going to make it.
They're just going to figure it out.
Being around those people is intoxicating.
You briefly dipped your toe in politics.
We all think Gavin Newsom is doing a terrible job mismanaging California.
I'll go two places on this because I'm interested in different things.
Would you ever run for office?
I know you briefly discussed it.
Would you ever consider being a politician's wife?
We'll start there.
I think that there is a point in our career where I would really like to explore it, meaning 20 years from now, 30 years from now, and to just completely say, take the collective wisdom we have and give it entirely back to the people.
Now it's not even feasible.
It's just completely unfeasible.
Nat and I are like, she's building a pharma business.
I'm building this new AI business.
We are just in the throes of it and we're in the throes of frankly raising our kids.
And I think like we enjoy it.
So I think the best thing that I can do is probably be influential.
You're both immigrants to this country.
What do you view the current push to deport all illegal aliens who are here in this country?
Do you agree with it?
Do you think it's gone too far?
Especially as people who came here legally who saw how hard that is to do.
Yeah, I came here legally.
Nat came here legally.
I came on an H-1B.
I think at a time when the H-1B is different than it is today, I don't think there was nearly as much scale and abuse.
Challenging The Patient Journey00:04:51
I think it's very important for people to follow the law.
I think that there's a complexion of how you start and how you deal with these problems.
And where you need to start is first you got to get all like the actual hardcore criminals.
And then you have to clean up parts, frankly, certain elements of the legal immigration system as well, so that you can reestablish trust.
And then I think in that, you can find a way to deal with all the people that are in the gray.
But those to me would be the order of operations.
What do you think is the biggest issue facing the pharma industry in the United States today?
I think we can, I would rather flip the question and say what's the biggest opportunity in the pharma industry.
There has been incredible innovation, 360 degrees round, and not the sector hasn't necessarily picked it up.
And this is the first time that instead the regulatory agency is taking it seriously and it's trying to course correct the trajectory when it relies to the clinical trials, the information, how it's gathered and so on.
It's been long due and this is typical.
The industry changes and then eventually the regulatory agencies move along.
And the biggest interesting challenge right now is to understand what is the massive change that is unraveling beneath this in the next two decades or three.
So what we've started seeing is how mathematics and digitalization can redefine the same information that we have today.
And we can see that you can boost it.
It can be more rapid.
It can give faster responses to patients.
But also what we are now really realizing is that the whole ideation to patient journey can be challenged, which means that today you have animal models, for example.
Is there a future and where do you put that moment in time where those animal models are replaced by encylical models?
And when we talk about trials, can you understand the same things with fewer populations and more rapid results?
If that happens, how can you lower the barrier and let more participants in, more people with good ideas?
And if that happens, is there a moment, and this is what a lot of people are preaching, but what is not happening tomorrow or in five years from now, slightly later on where exactly I don't know, will this not matter?
Because all these kinds of problems will be solved.
And so what is the relationship between the pharma industry and the patient?
And so how will that be different?
What is the future pharma?
What will they be supplying to help patients have a better quality of life?
How will it be more designed for their needs?
Do you think they earn the boogeyman title that they're currently given by patients in the United States in terms of increased costs, not knowing where the money's going, pushing medicines on us via advertising, you know, things that like say Bobby Kennedy is very passionate about versus that a lot of the companies are understanding where the consumer is going and working to get there on their own?
I think you always have to look at different setups to really understand one thing.
Sometimes when you're in one thing, and that's the only thing that you're seeing, you have a narrative.
And sometimes when you just take a step back and look at what happens in the rest of the world, you have a different narrative and it adapts to the perspective.
So in every industry, there's parts that are dysfunctional and there's parts that need to be optimized.
And having people that through data can train that model to be better has to be welcomed.
Because in a world where we don't talk about these things and we don't have an opportunity to improve them, what happens that they stagnate and then the problem becomes 90% and overcomes the opportunity.
That's what we don't want.
At the same time, the industry, the regulatory landscape, the nations evolve so that they can be adaptive.
And as long as there is that tension and that tension can be held and there's competition, I think that the trajectory is positive.
Chamof, you're a true rags to riches story.
You went from working at Burger King to leading the instant messaging team at AOL to an early executive at Facebook to running your own venture capital firm.
Professional Jealousy And Industry Disaster00:14:46
Has money changed you?
Yeah, it has.
I think that it's changed me mostly, well, I mean, obviously it has.
It's allowed me to be more free.
It's allowed me to say what I think.
But it's also distracted me.
I think in many moments it's made me not the person that I am.
It's made me waste a bunch of time.
It's made me way more insecure.
It's made me think of everything I didn't have.
So it's a mixed bag.
What's something you each splurge on without guilt?
Oh, I can tell you what I do.
There is an incredible, I mean, I don't even want to say it, but I'll say it because she deserves it.
There's this woman, Olivia Landon.
It's called Long Hill Wagyu outside of Austin.
And I'm probably her largest and best customer.
And I buy it.
I make it.
I grill every Sunday for the family.
It's probably our most favorite meal.
Please say us.
No.
Yes.
It's not cheap because the cost of, I mean, all beef has gone up.
Right.
But man, it is excellent.
Excellent.
And then the second one is wine.
Those are my two things.
She is wonderful, amazing.
And honestly, I love Sundays because we get to do this together.
And it's the only time that Shamath provides some health in the household.
So it's magic.
It's pure.
And it's, I can't splurge on anything because I need to set the example because he would like to splurge on everything.
And so I need to counterbalance.
And so I try to normalize it and bring some groundedness to the family, which is, it seems extreme and it's like, oh, boring.
It's necessary.
It's a necessary medicine.
What's the craziest thing you've ever spent money on?
Oh my God.
I mean, I shouldn't really say.
I mean, I think it's in Wikipedia, so I can just say it.
But, you know, I had been obsessed with planes.
And then there was a moment where President Trump and Trump won in 45 passed a bonus depreciation in a moment where, you know, we had a success.
And so I did it to take advantage of it.
And I rationalized every decision.
And she was like, I want to take my distance.
She's like, she's like, this is the stupidest decision.
I was very sad.
I was very sad.
We're going to regret this.
So what was it?
I bought a global 7500.
Okay.
It was so.
But, and in my defense, it was during COVID, so I got a good deal.
So honestly, if you're going to say this, I'm going to say the rest.
No, no, no.
But like, yeah, say the rest.
But like, it was a disaster.
And it started, it was the point at which everything stopped working.
But I started making a whole series of horrible decisions.
My ego got out of control.
I was led by insecurity.
I stopped thinking critically about investments the way that I used to.
Is this that SPAC timeline?
This was like a bunch of the SPACs where, you know, and she was like, what are you doing doing these biotech spaces?
Like, you have no, you know, knowledge of these things.
She's like, why are we doing them?
And then she was like, you know, these things are wrong size.
They're too big.
She was right about all of it.
I kind of marched forward anyways.
But that was the biggest splurge, but it was a huge.
It was a huge disaster.
Huge disaster.
I don't find it funny.
And I cried all my tears trying to stop him.
I felt responsible for the kind of face that you have in a moment that you are not capable of coming up with all the opportunities in the world to help the person who's in front of you.
And then you have an albatross that put, and that's the word I use.
And remember us fighting hugely over the word albatross.
Yeah, she's like, that thing is an albatross.
And it'll drag us down.
And then a very specific moment in time happened, which the market shift.
And I remember it specifically.
March of 22 when Russia invaded Ukraine.
Because it was called like the Silicon Valley bubble, it collapsed.
And because he was so vocal, he was the face of the collapse.
And There was, at that point, there comes a moment in life, and I think we all get through some of those moments.
If you have the luck to be in the arena for long enough, every single thing goes under the microscope.
And what happens is that you realize that you made some good decisions, but you were not a genius because you also made some bad decisions.
difference is that in moments where you have tailwinds you don't really feel it until you have headwinds and then it's all a disaster and so obviously we I'll tell you a great story about this process She was like, we need to confront this.
And we need you to find structural change.
She's like, like me, like how you approach your daily job.
How do you keep your head down and be in the engine room?
There would be Saturdays where we'd sit in bed and she would go to Reddit and she would read me the negative feedback.
And it's brutal.
Because my point is that sometimes he says something and then it becomes a meme.
You live in your own ecosystem of positive feedback instead of hearing the negative.
Exactly.
But not even, not even that.
I think the point was more he says something that then has a negative impact on his life or our lives.
And my point is like, are you saying it because you really think about it and you really want to say it?
Or are you see it out of instinct and emotion and because you're feeling insecure?
And I just wanted to divide those into two different categories.
What's the craziest thing you've ever seen somebody else spend money on?
More than him?
Yeah, I mean, I think the biggest one was a friend of mine, really great guy.
He bought an island.
And then, you know, like everything is triple the price, right?
So then like you have to build the houses and this and the that.
And it's like, it was a disaster.
And then his business changed and it was hugely negative for him.
All right, now we're going to play the best game ever called Would You Rather?
You both answer.
Would you rather?
At the same time?
You can do it at the same time or one after the other.
Okay.
Dealer's choice.
Would you rather have one extravagant date night in Paris or a quiet weekend at home with no phones?
Oh, this is, we know this is a little bit more.
There's seconds.
Like B, 100% B. Would you rather be the smartest person in the room or the most self-aware?
B. I'm trying to be self-aware here.
Okay, let's see.
I mean, you both know.
She said, she said it's a desire.
She said, would you like to?
That's a desire.
She's asking it, what do you want?
Would you rather lead a movement or quietly mentor the person who does?
A.
I would love to have A, but I know that this life will preserve for me, like will give me an opportunity.
The maximum I have close to that is a B, and I'll take it happily.
Would you rather never fail again or never feel pressure again?
No, I'm happy to fail.
And I love pressure.
I think we have one life.
Yeah, I agree with that.
Would you rather live in Lake Camo or Lake Tahoe?
Neither.
Oh my gosh, neither.
Yeah.
Neither, not our vibe.
No.
They're both nice for different things.
Too beautiful, pretty, but the rhythm is not the rhythm.
Like, I know you well enough to understand that you and I have some similarities and one is the rhythm.
And I don't know if it happens to you, but when I, my pace, like let's say it's the 15th of August and everybody in Italy shuts down or something like that happens, pace goes down.
I get a little sad.
Does it happen to you too?
No, I feel like I need to find something to go do.
Okay.
Like I can't, I can't just have a quiet day.
Like somehow I end up messing up.
I need to go find something to like.
I just say like stop or like I need to like.
When pace goes down instead, I genuinely feel a little depressed.
So I don't like it.
What's your daily routine?
Mine is we wake up, depending on when Nat has calls with Europe, between she'll wake up at 5.30, but normally we're up by 6.30.
Kids run into bed, except on Mondays where our four-year-old sleeps with us and Thursdays our six-year-old sleeps with us.
The older kids do not sleep in the bed with us.
16-year-old was a little tired.
Got a little dicey.
We go downstairs at seven.
We eat breakfast together as a family.
What do you eat?
I have the same thing.
Cottage cheese, chia seeds, flax seeds, dragon fruit, and blueberries.
Oddly specific.
And then I have, and then I have a latte.
I have it every day.
Same thing, every day.
Whole milk, raw milk, whole milk?
Whole milk.
And then by 7.30, I mean, this is TMI, but I have certain biological things that I have to get done instantly as soon as I eat.
And then I brush my teeth and then I work out from 7.45 to 8.45.
And then I shower and then I go to the office.
That's me.
I have been working throughout all those.
She's been working this whole time.
She's been working since 5.30.
But she does, no, but she does always make, she always makes breakfast between, meaning eats breakfast with us.
If I can.
But she's in between meetings though.
So you guys eat dinner together as a family?
Yeah.
Always.
Every day.
And do you guys are home to put the kids for bed or how does that work?
It works that he is passive in the room.
And that's the time where I really try my best to teach them Italian and like read Italian books.
Oh, hold on a second.
I'm just going to tell this story.
I was like, oh, I'm going to read these Italian books.
And I thought, God, this is me.
Look at me.
I'm stepping up.
What a great dad.
And then she's like, the accent.
She's like, Amore, stop.
And I'm like, why?
Your fucking accent.
This sucks.
And so, what is the point?
You're speaking in this English accent.
I was so hurt because I have invested eight, nine years to learn this language that is shrinking in the number of people that speak it.
And so I don't, and now I just sit there while she speaks Italian.
The kids speak perfect Italian and I speak this English accented Italian.
He's a very sad pants story, so don't believe it.
He knew Italian when I met well when I met him, he knew a little bit of French from growing up in Canada.
And so he switched to Italian marvelously well because he's very, very, very smart.
But he didn't spend time actually trying to learn Italian, except one year.
He did one year of like lessons to try to learn Italian.
But yeah, honestly, I don't want our kids to have an Italian accent when they're speaking English and I don't want them to have an American accent when they're speaking Italian.
So she told me to shut up.
So I sit in the bed.
I sit in the bed like a lump and then she sits there with the kids beside us and that's the nighttime routine.
And then they go to bed.
What's been the best part of hosting the all-in podcast with the guys?
Honestly, the, the, it's, it's, it's strangely brought us all closer together.
There was, um.
Were you guys originally all close?
Well, me and Sachs, me and Sachs have known each other for 22 years.
Me and J. Cal, maybe for 25, but we hated each other for the first five.
I couldn't stand Jason.
He was like an executive at AOL when I was there.
And I thought, this insufferable guy.
And then somehow we kind of started bonding in the early mid-2000s, became friends.
Freeberg joined our friend group maybe in 2012 or 13.
So this was just your friend group that you guys were like, let's do a podcast together because we're all bored with COVID.
Yeah, we were like losing our minds.
So what's been the worst part about doing it?
We cannot agree on anything.
So the thing has not really evolved.
Meaning, you could say, guys, you should prepare more and it should have 40% business, 20% politics, 10% tech.
We could never get an agreement.
You would say, hey guys, we should be in a studio.
It's a better vibe.
Can't get anybody a degree.
Hey, guys, XYZ person wants to be interviewed.
It's honestly, Katie, it is like four people in four different directions.
Has it brought you guys closer together or further apart?
Closer.
Yeah.
Would you do it again?
Yeah, yeah, yeah.
Yeah, it's been great.
Has anyone ever asked to be of a fifth member of the gang?
There are people that we call the fifth besties who are like the people that we rely on, like Brad Gerstner.
He's been a fifth bestie a lot, Gavin Baker.
But the funniest and the most tilting thing is that our moderator, Jason, is he takes the moderation job very seriously, but he's also incredibly tilted by Andrew Ross Sorkin.
I think it's like a professional jealousy thing.
So me and Freeberg are in this long-term game of every time in the pod.
I didn't tell you this, in the group chat, we always text like, oh, Sorkin would be great at this.
Well, Sorkin would be great at this.
Set your control.
Set your control.
We're in a long-term troll of Jason.
Who's the spontaneous one and who's the planner?
Between the two of us?
Yeah, because he is spontaneous to the point that he's very focused.
And we said he's very, very smart on the things he does.
But on other things, on other things, he's just like not good.
Like, for example, if I had ever asked him to book flights, he would book flights at midnight with children that are three years old.
And you're like, do you understand that this child will not sleep throughout the whole trip?
What happens when a child is sleep deprived after 24 hours?
They will start crying and crying.
It'll be harder for them to sleep and it'll be a nightmare.
But he thinks somebody else will manage that nightmare.
That somebody else is me.
And so I don't, yeah, he doesn't put many things together.
So the planning part is just really bad.
And it's so funny at the same time because it's so bad.
It is really bad.
But we have found that we have like five families that we all have very kids the same age.
We spend a lot of time.
Sleep Deprivation And Bad Planning00:06:00
And it turns out that.
Oh my gosh, Jason Chang.
Jason Chang, one of the husbands, is like the super planner.
So now the whole point is just to make sure everything we do, Jason.
Jason's involved.
He plans everything.
I didn't want to take on the planning role, but because he was not really just not even meeting the understanding of what goes around.
Like, for example, let's book a holiday for five children that have a specific schedule, the day off.
Like things like that, where you're like, okay, because he wants me to do that.
But it's the same thing when he's asked to contribute to the kitchen, for example.
Hey, can you help me do the plates?
And he starts saying like, where are the plates?
And in our house.
And then, and, and, and what a, sorry, what a, sorry.
Where are the glasses?
And at the end of the day, of course, you say, don't worry, I'll take care of it.
And it's a, it's all a strategy, of course, but I don't know how to get out of the thing.
So anyways, now we have this friend of ours who we've discovered is unbeatable.
So some things like- Spreadsheets, itemized lists.
I love that.
Like if you go and take ski lessons, he'll say, would you guys like a weighted cost for your hours?
Because you didn't actually use all of the time.
And you're like, who is this guy?
This guy's putting the children together, making sure everybody commits.
What's a conspiracy theory that you believe in?
The conspiracy theories are not, don't really blend in in my way of thinking.
So theoretically not.
But I would say that if I did end up believing in one, I would tell you that it's not a conspiracy.
It's facts.
So.
I think there are UFOs.
I think it's mathematically at this point inconceivable.
Do you know what I mean by this?
Do I asked Elon this question specifically in the podcast and he claims that there's no UFOs?
I think it's mathematically.
I typically believe what Elon on these things.
Yeah.
It's mathematically implausible that there are none, though.
But it's physically plausible, just because it's physically plausible that they may have burned up or we only have fragments.
Yeah.
But it's mathematically implausible that as vast as the universe is, with all of our different, like it's not as if many trillion light years away, it is also 2026.
Do you know what I mean by that?
They've been evolving at a very different rate of speed.
Okay.
I think it's a limited one.
If I had to go like with your fun one, because we are protected by the moon, like there's so many aspects that might make what you're saying 50% probable, 50%, like with my ignorance level, I would say that there's a high probability that you're wrong.
What's the last book you read?
What's the?
Last book you read.
Oh gosh.
I just bought this book called Art Thief.
Have you heard about this?
No.
There is a guy who over the course of 20 years stole $2 billion worth of art from various museums across Europe and he would keep them in his attic.
Did he give it all back?
And he got caught and his mom like destroyed half of it.
His mom went to jail.
He went to jail.
The girlfriend went to jail.
Then he got released.
Then it turned out that he stole a bunch more, went back to jail.
And this New York Times best-selling book is about that guy's life.
Oh, that's cool.
Yeah, Art Thief.
Ring.
A friend of ours actually.
By Jamie's book.
Yeah.
us this book and uh it's it's the story of ring Jamie Simov is the founder of Ring.
Yeah, but it's a story.
I love seeing perspectives of our friends in a different light and seeing their journey.
So the last question we ask everybody in the podcast.
If you could host a dinner party with three people, dead or alive, who's sitting at the table?
And what are you eating?
Okay, my people would be Winston Churchill, Descartes, the mathematician, and Michael Jordan.
What are you eating?
I would have Wagyu beef.
Well, okay, I would start with an Amuz bouche, something light.
I would have maybe like some taglia telli with white truffles, then Wagyu, really great pairing with wine.
And then I would have like sticky toffee pudding at the end, like really calorically dense because Churchill was into calories.
Those would be my three.
Who are your three?
In this moment in time, I think I would love to have Jesus at the table and just sense what it means to have faith and understand.
But he wouldn't be a fun conversation because I would guess he would ask a lot of questions and answer very widely.
So I would still want Napoleon and Cleopatra for opposite reasons.
Napoleon, I feel, is the epitome of something that I've observed very much in the Silicon Valley, and that's really an interesting fact.
Men with big insecurities that are incredibly successful.
There's something magic about how these two things that would otherwise be in collision actually provide the setup for great success stories.
And what are you reading?
Nothing.
No, she'd want like air.
No.
The meal would be like air.
I would have, actually I'm in, I don't know, a lot of small plates.
I would want fish.
I would want vegetables.
I would want a little bit of bread.
Terrible.
Middle Eastern taste.
I don't know.
Terrible.
Everything and nothing.
Basically air.
Thank you so much for doing this.
Thanks, Katie.
Thanks so much for watching this episode of the Katie Miller Podcast.
Don't forget we're available every Tuesday night at 6 p.m. Eastern where you get your podcast.