Skip to main content
Sahil Bloom

Sahil Bloom

Entrepreneur

Nov 3, 2026

NickHOST
1:04
So take us back to the moment you made that life-changing decision.
1:10
Yeah, I mean, I think the context that's important around that decision is my whole life I had operated under the same assumption that you're saying other people would have around that number, which is to say like 500K, like my life will be perfect.
1:25
Everything will be great.
1:26
You look when I had no money when I was graduating school and I was going to go get my first job.
1:30
And I think my first salary was like $70,000 a year.
1:33
I remember thinking like 100k a year, I'm going to be set.
1:37
Everything's great.

16 MINS LATER

NickHOST
17:33
oh no
4:57
So what have you learned in some of the other statistics or things that you've done through your walk that have gained some light on you know, how many times we're going to see that parent or how many times we're going to be, have summers with kids or anything like that, that you're taking a heart in your, in your world.
5:19
You know, I think there's the two sides of this, right? There is the aging parent side, which we talked about that moment of realizing how few times I had with my parents.
5:27
And then there is the juxtaposition of that with this period of having these young kids in your life.
5:35
And the truth with children and the statistics around this is a terrifying one.
5:39
I did this research for the book.
5:40
I went through the American Time Use Survey.
5:42
It's this incredible rich data set of tracking how people spend their time over the course of their lives.

24 MINS LATER

29:37
So what's been
20:03
So tell us about her and your story.
20:08
Yeah.
20:09
Um, Elizabeth and I met, uh, actually, I think 18 years ago today, um, I got a Facebook reminder.
20:19
It's not our anniversary.
20:20
It's an even funnier story.
20:21
Uh, I got a Facebook reminder of one of those like 18 years ago today.
20:24
Uh, because, uh, She was a freshman in high school.

23 MINS LATER

43:50
So now let's dive into five types of wealth and how all-encompassing each one, like each pillar really is, and give us a tangible takeaway that we can enact today to work towards our goals.
speaker_1MODERATOR
0:19
I want to start with a
0:20
question.
0:22
This question.
0:24
If you were the main character in a movie of your life, What would the audience be screaming at you to do right now? If you were the main character in a movie of your life, what would the audience be screaming at you to do right now? We've all been there, watching a movie or television show.
0:42
We just want to jump through the screen and grab the main character, shake them, right? Say, chase the girl to the airport, don't go down in that basement, look out behind you.
0:53
Whatever that thing is, you are that main character in the movie of your life, and there is something the audience would be screaming at you right now.
1:02
So what is it? What is that thing that is so blindingly obvious from the outside looking in that you are either choosing to ignore or have yet to create enough perspective to see? I want you to think about that question in the few minutes that I have with you this evening, and then in the days and weeks ahead.

37 MINS LATER

Jeff HaleUNKNOWN
38:03
Hale, there's a great story about how you met Tim Cook, Apple CEO, I think, right? Is that you? Can you maybe tell the guys that story? I thought it was pretty neat.
3:24
Um, Talk about that a little bit as far as the value of, number one, listening to your body and then actually taking action, and that action was tied to failure.
3:37
I think that, look, we live in this social media age.
3:41
Everything is about highlights and wins and success stories and achievements, and that's all you see.
3:47
And as someone with a platform, And a platform that in large part has been built talking about things that are going well in different ways in my life and things that I'm learning and experiences that I'm having that have for the most part been good things, making sure that you share the L's that you take along that journey is very important.
4:06
And I feel a responsibility to do that because as you know, and as we all experience, those failures and the L's are what shape you for successes.
4:19
And what I have often thought about and what I remember learning from my grandfather and from my father is like, what you're trying to do is avoid...
4:28
the failure that truly knocks you out like you can take the glancing blows right like if you take the punch but it's just a glancing punch versus the straight knockout blow that takes you out you can survive those just survive in advance just take the next step and now you know i i felt like i was in a position where if i stepped off then um i can go and run another marathon in a month when it's cooler and i can go and show the fitness that i feel like i have or i i can try to grind this out in this moment maybe end up in the hospital maybe end up with an injury and now i'm not able to run for months um and i think that all of us need to take lessons from elite performers in these ways i i saw recently a whole um thing from Elliot Kipchoge, one of the greatest marathoners of all time.

8 MINS LATER

13:29
A
21:49
That's all you can think about
21:49
... you get the flu.
21:50
You're like, you can't remember how good it felt to just feel healthy when you woke up in the morning.
21:55
It's the only thing that you can think about.
21:57
And so I just think that for most people, where we have gone awry when it comes to health advice, and this is really the entire w- entire world of, of, like, health gurus and health advice that you see on the internet, is overcomplicating what it means to be healthy.
22:17
And you and I have talked about this in the past.
22:18
Like, I, I think the most powerful thing that you can do is remind people that the basics of becoming a healthy person are freely accessible to anyone.

21 MINS LATER

43:29
And to me, those are, those, they have like different connotations in my mind, and I'm curious if you think about like what it means to be happy.
3:57
So can you take us back to that moment and like what that realization was and why it hit you so hard?
4:02
Well, I appreciate the kind words.
4:04
I really spent the first 30 years of my life marching down what I would think of as the most traditional path to a successful life.
4:13
I convinced myself from a young age that all of my happiness, my contentment, my fulfillment.
4:19
It was like on the other side of something, right? Like some achievement, some bonus, some promotion, some title.
4:24
I was gonna get that thing and I was gonna wake up and just feel great, right? Like it's that idyllic land of success that sits off in the distance.
4:32
And unfortunately, all along that way and along that path, while I would go and get that thing, I would start to see other areas of my life falling apart.

19 MINS LATER

24:00
And how do you think about it? And how are you kind of creating your LifeRaiser?
19:37
What, what are some examples of some of the questions?
19:39
Each type of wealth has five statements.
19:42
You answer for each statement from strongly disagree to strongly agree.
19:46
So under time wealth, one of the questions is, "I am in control of my calendar and priorities." That is a very essential piece of time wealth.
19:55
If you don't feel like you are in control, you could be making $10 million a year, but if you have zero control over how you're spending your time, the meetings you're in, the things you're thinking about, you are not very time wealthy.
20:06
I have plenty of friends who are like that.
20:07
Tremendous financial wealth, but if they have to answer a phone call from an angry client at 11:00 PM on a Sunday night, they don't have a lot of time wealth by the definition that we're talking about.

17 MINS LATER

37:20
Can you talk about how to even assess whether or not the work that we're doing is aligned with our purpose or the life that we're living is aligned with our purpose? I believe the question for that is what would your 10-year-old self say about your life today?
10:40
Sure.
10:41
I, I do think that, um...
10:42
Look, I've experienced this very recently in a pretty r- visceral way in my own life, that like I was in my office a f- a few weeks ago just before the launch of this book, and I was working on something, very focused, locked in on something for the launch.
10:57
And my son, who's two and a half years old, came barging into my office and started doing two-and-a-half-year-old things.
13:46
Yeah.
13:46
It's what allowed capitalists, free markets to grow, all of these things, commerce.
13:50
Um, but unfortunately, it is clearly not the sole measurement of building a good life.
13:57
[gentle music]
19:59
Old, old movies, man.
20:00
Old movie.
20:01
I love it.
20:01
Yeah, like Ron Howard, you know, Academy Award winner for it, I think.
20:05
But, um, there's this scene at the very end of it, like climactic scene.
20:08
They're like trying to enter back into the atmosphere, and basically they, they find out that if they come in too steep they're gonna like blow up, and if they come in too shallow they're gonna like skip off like a rock on a pond and just be like floating in space until they die.
20:20
And they have to come in at the perfect angle, and they're like they have to do it without computers.

43 MINS LATER

63:31
The quest.
11:51
So when it comes to wealth, one of the things I wanted to kinda bring up, because this is under attack as well, is it better to gather your happiness at home or at work? Because a lot of people who've been remote, they're being forced to go back to the business.
12:02
business.It ca- it is completely up to you.
12:07
And the reality is, uh, what you don't wanna do is try to tie your happiness to some destination.
12:13
That is what most people do.
12:15
You know, you, you say, uh, "I'm gonna be happy when I get X," or, "When I get this promotion," or, "When I get that amount of money," or whatever that might be.
12:23
You create this, like, conditional equation on your future happiness, and that is a recipe for disaster because it's called the arrival fallacy.
12:30
What happens is you get that thing, you have this momentary blip of euphoria, and then immediately feel this dread of not doing enough.
13:21
Yep
4:03
How did that happen for you?
4:04
Yeah.
4:04
I'll say a few things here.
4:06
Um, we all actually know these things.
4:10
Uh, this is a funny thing for me to say.
4:11
This is a self-improvement, self-help book, and, um, at the very beginning of the book, I say, "This book will not give you the answers for your life," because you already have the answers within you.
4:23
You just haven't asked the right questions yet to reveal them.
8:38
Tiny.
55:24
Absolutely.
55:25
Um, has sort of been lost.
55:27
I mean, now we, we have this, this, it's sort of become a meme of like, you should work smart, not hard.
55:33
And my take on that in general, especially for young people when they bring that up is you cannot work smart before you work hard.
55:42
Uh, and for one actually very simple reason, which is when you are young, the only asset that you have is time.
55:48
That is literally your only asset because you don't have money.
55:51
You don't have networks.
57:06
What would you say to them? What do they need to know?
23:14
Hmm.
23:15
And it's exactly as you said.
23:16
I think that ultimately, your outputs are a result of the structure of your inputs, and your ability to create a clear structure around your inputs is how you create outputs over long periods of time.
23:27
And in order to do something for 10 plus years, you have to have clear pathways to do that.
23:31
I, I try to tune into my energy.
23:34
And so what I would encourage everyone to do is over the course of a day or over the course of a week, think about the type of energy that you feel during different windows of the day.
23:44
What I mean by that is you are going to have a window of time during the course of the day when you feel most creative, when you feel like you could sit down and actually create things, when you feel that spark of creative energy.
26:21
Mm
17:02
Is this fair?
17:03
That's a fascinating thought exercise and thought experiment.
17:07
And it actually draws upon something that I've thought about recently, which is To just consider and audit how much of your quote-unquote desires are being influenced and heavily formed by your environment, by the people around you.
17:25
I've often written or spoken about the fact that it is very difficult to play this game of creating your own scoreboard, of living differently.
17:35
when you are surrounded by people who are trying to live one way.
17:39
The most classic example of this to me is like, if you were trying to live a simple life grounded in core, really what I would view as moral values, family and spirituality and religion, principled values, and you're living in New York City, a place that really glamorizes wealth and status and you know, where you send your kids to private school and where you vacation in the Hamptons.
18:04
And like, that's how we measure self-worth.

7 MINS LATER

25:34
So define for me, Sahil, your definition of a successful life.
2:06
... and how you transitioned from what you wanted to do when you were younger into now, and then we can talk about the economy.
2:13
Yeah, I took, uh, you know, out of, out of college in particular, I basically took the path that is, like, the straight and narrow path to what we all think of as the successful life.
2:24
Like, I, I had sort of gotten indoctrinated into this belief that my journey to living a happy, content, or fulfilled life was, uh, to make money and, uh, you know, accumulate fancy things, like build status, get those pats on the back.
2:38
I, I figured that I would just, like, do that enough that I would wake up and feel good about myself.
2:42
So I took the job out of school that, you know, was gonna sound good for the LinkedIn post rather than maybe the job that I actually, actually wanted.
2:51
Uh, and I sort of just marched down this path for seven years to start my career, um, convincing myself that I was always just one bonus or promotion or title or fancy bottle of wine away from feeling fundamentally different about who I was.
3:05
You know, feeling like I was enough.

16 MINS LATER

19:22
How do we, as citizens of this AI world, add value to society when so much of my job could be automated? How do we build wealth, going back to your book, Five Types of Wealth?
8:27
And so I went, "Oh, well, maybe this is possible." Yeah, I think that's the main piece.
8:32
You know, the thing that I think is so powerful about this book in particular, and I was saying this to you before we started recording, but I think it bears repeating here, is I've read hundreds of books within this category of, you know, self-improvement, personal improvement broadly.
8:47
I obviously wrote a book in this category.
8:49
The thing that I think most suffer from that we often fail to acknowledge is they are about efficiency at all costs, productivity at all costs, productivity maxing, right? Optimizing all areas of your life.
9:04
And in particular, when it comes to habit formation, behavior change, you lose something if you focus on productivity at all costs.
9:13
It is possible to optimize the life out of your life.

40 MINS LATER

49:16
No big deal, but I can still keep with my plan."
49:18
plan."It all sort of relates to this embrace of the ordinary that I absolutely love.
22:23
How much has it impacted your personal and work life and what kind of made you feel the need to write about it? For several years,
22:31
I have felt that social media in general and the media more broadly creates this very negative skewed view of reality.
22:42
So there's this meme that I came across several years ago that I absolutely love of a guy in a rain jacket with an umbrella over his head looking really sour, staring at a TV screen with a bunch of storms on it.
22:54
And then you see this like bright sunshine over his head.
22:57
And so it's this idea that that is all of us.
22:59
We're watching the news.
23:00
We're reading and consuming things that are telling us the world is all dark and stormy.

31 MINS LATER

54:04
But for that to be something that you wanted to dedicate time to, I feel like I need to dedicate some time to it here as well.
27:47
So it's really brought me into like a pretty like risk free zone, I guess.
27:59
I think the fundamental recognition here is that there are two types of priorities in life.
28:06
There are the priorities we say we have, and then there are the priorities our actions show we have.
28:14
And oftentimes in life, there's a big gap between those two things.
28:19
I was living that gap.
28:21
If you would come to me in 2020 and asked me what my priorities were, what I really cared about, I would have said a bunch of great sounding things.
28:29
I would have said my family.
22:31
No.
22:31
So these two famous American authors, Kurt Vonnegut and Joseph Heller, they're walking around this palatial garden estate of this billionaire in the Hamptons, and Vonnegut turns to Heller and he says, "Joe, how does it feel that just yesterday the owner of this home made more money than your most famous book, Catch-22, made in its entire lifetime?" And Heller thinks about it and says, "Yes, but I've got something that he'll never have." And Vonnegut says, "Oh, yeah? What's that?" Heller replies, "The knowledge that I've got enough."

6 MINS LATER

29:18
Hmm
29:18
... sending the text is infinitely better than doing nothing.
29:21
Like, getting together with the friend for the little coffee date, calling your mom for the 10 minutes, infinitely better than doing nothing because it compounds in that same way.
29:31
But when you talk to ambitious, high-performing people in particular, one of the worst habits we all have is we constantly allow optimal to get in the way of beneficial-
6:17
But focus for a moment on that comment about your parents and the fact that they had very high expectations for you, yet in the support of you, which you are quite vocal about them being exceptional parents to support you, they could never get you to dismissing that sense of either insecurity or not being enough.
6:38
Yeah, you know, I have this belief that like the two pillars of strong relationships are high expectations and high support.
6:46
And that is high expectations to say, I have very high expectations for what you are capable of achieving.
6:52
I believe you are capable of excellence in everything that you do.
6:56
But importantly, pairing that with high support, which is to say, I am here to lift you on my shoulders to help you go and meet those high expectations that I have for you.
7:05
The reason the two are important together is because high expectations without high support manifests as resentment.
7:12
Like we all know someone like that in our lives who seems to have high expectations for us, but then they're nowhere to be found when it comes to meet those expectations.

10 MINS LATER

16:52
How did you end up putting the family first?
3:56
We're going to go right
3:56
into it.
3:57
I love it.
3:58
Those words hit me at a moment in my life that was pretty interesting because it was a time in my life when from the outside looking in, I was winning the game.
4:09
I was doing the things that you're supposed to want to do.
4:12
I was... 30 years old, I had the fancy sounding job, the title, the money.
4:19
I had the markers of quote unquote success as we typically think about it.

17 MINS LATER

20:56
Tell us more about your views on a rival fallacy and the pitfalls there.
47:48
So talk to us about relationships and in the context of entrepreneurship, what we need to keep in mind.
47:54
There are going to be long periods of loneliness on your entrepreneurial journey, and that's okay.
48:02
That is a necessary cost of entry to the personal transformation that you are trying to create in your life.
48:10
Because literally what happens is you start changing and growing as you were with the things you were building, the things you were focusing on.
48:17
And your environment that you previously existed in has not changed.
48:21
And so there comes to a moment when it feels like you are actually speaking a different language than the people that you used to be close to.
48:28
And they will not understand the way you were living and the things you were doing.

14 MINS LATER

62:01
Do they exist already? Are you creating these companies? What is it typically like? What's the structure typically look like?
56:13
I'll use yours too.
56:20
That dislocation between the external perception of how things are going and how you feel things are going is such an interesting scenario to find yourself in.
56:31
And really at the start of COVID into the end of 2020, I started to feel that in such a pronounced way.
56:39
That from the outside looking in, I was winning the game.
56:42
I was doing the things that you're told you should want to do.
56:45
Make money, get the promotions, bonuses, the titles, like the fancy things that you're told represent what a successful life looks like.
56:53
And under the surface, internally in my own life, I had started to feel like a lot of things were falling apart.

13 MINS LATER

69:51
Mm-hmm.
1:42
Tell our listeners about that.
1:44
Yeah, this was in May of 2021.
1:46
And just to set the context, I had spent the seven years leading up to that marching down what I would define as the most traditional path to a quote unquote successful life.
1:57
I had a job that was a job you would be told you should want, high paying, impressive sounding job.
2:05
I was doing the things that you're supposed to want to do.
2:09
And by the time that period rolled around, COVID started in 2020 and 2021 came around, I had started to have this sensation that I was winning in one very specific domain of life, making money and starting to see cracks and losing in all of the others.
2:28
And it all came to a head with this single conversation.

22 MINS LATER

24:38
Related to that, what's happiness? What makes you happy?

Scroll for more appearances

We value your privacy

We use cookies to understand how you use our platform and to improve your experience. Click “Accept All” to consent, or “Decline non-essential” to opt out of non-essential cookies. Read our Privacy Policy.