25 Years Of Founder WISDOM In 55 Minutes (ft. Jason Fried)

Summary

In this engaging podcast episode, the host, a founder, delves into the dynamics of risk-taking in business, reflecting on his own experiences and the lessons learned from observing the hedge fund industry. He discusses the importance of maintaining a balance between innovation and stability, the challenges of the entrepreneurial journey, and the value of loosening control to foster growth. The conversation also touches on the significance of copywriting skills, the impact of luck in success, and the pitfalls of chasing the latest trends without considering long-term implications.

Takeaways

• 🧑‍💼 The founder's role is to inject risk into the business, taking advantage of ownership to make bold moves that others can't.
• 🤔 A significant portion of the audience prefers a guaranteed 7.5% return on investment rather than the potential for higher but uncertain returns through active investing.
• 🎓 The importance of recognizing that at any point in life, a consistent and guaranteed return on investment is a smart choice for most people.
• 💡 The realization that even with significant resources and expertise, as seen in hedge funds, beating the market consistently is challenging, highlighting the folly of overconfidence in individual investment abilities.
• 🎷 A metaphor of loosening grip on a drumstick or any instrument to improve control and performance can be applied to various aspects of life, including business and parenting.
• 🤝 The value of transparency and open communication in business partnerships, as demonstrated by sharing personal financial goals and expectations early on.
• 👶 Raising children with the understanding that they are their own people, encouraging them to find their own way while providing guidance and support.
• 🎲 The acknowledgment of the short-term nature of success or failure in various aspects of life, including business, and the importance of long-term perspective.
• 🤖 A reminder that in the rapidly changing world of technology and business, not everything requires immediate attention, and the importance of not falling into the trap of 'must-know-now'.
• 📚 The benefit of revisiting historical perspectives, such as through old newspapers or podcasts, to gain insights into how predictions and certainties of the past have played out.
• 💡 The emphasis on creating useful things and the joy of turning ideas, even those that started as jokes, into reality that benefits others.

Q & A

What is the main theme discussed by the Founder in the beginning of the transcript?

The Founder discusses the concept of risk in business, contrasting the guaranteed 7.5% return on investment with the potential for higher, but less predictable returns from actively investing in individual stocks or starting a business.

What was the surprising result of the Founder's Twitter poll?

The surprising result was that 40% of the 300,000 followers chose the option of actively investing with potential high rewards and risks, over the guaranteed 7.5% return.

Why did the Founder choose option A in his Twitter poll?

The Founder chose option A because he values the guaranteed 7.5% return with no effort, considering it a no-brainer given the consistency and compounding potential over time.

What did the Founder learn from visiting hedge funds in New York?

The Founder learned that even with advanced software and significant resources, hedge funds and their highly paid employees often struggle to consistently beat the market, which made him question the ability of an average person to outperform these professionals.

How does the Founder view the importance of business in one's life?

The Founder views business as a practical way to manifest dreams and realities, and as a spiritual journey that can have a significant impact on the world.

What personal development lesson did the Founder learn from playing drums?

The Founder learned the importance of not gripping too tightly when starting a new activity, as it leads to faster fatigue and less control, which is a metaphor for various aspects of life including business.

What is the Founder's perspective on the business world's tendency to absorb lessons from other fields?

The Founder questions why the business world is often seen as a recipient of wisdom from other fields rather than a source of it, suggesting it might be due to the business world's willingness to pay for advice.

How does the Founder describe the early days of a company?

The Founder describes the early days as exciting due to the energy, hope, and the unknown possibilities of building something from scratch.

What challenges does the Founder face during the middle phase of a company's lifecycle?

The Founder faces challenges such as maintaining motivation during periods of stability, dealing with internal politics, and managing the transition from a creator to a maintainer role.

How does the Founder approach injecting risk into the business?

The Founder approaches injecting risk by initiating new projects, exploring different business models, and allowing the company to be 'off balance' in a healthy way to maintain excitement and prevent stagnation.

What personal project did the Founder undertake outside of his main business, and why was it exciting for him?

The Founder created a website called 'samslist' as a fun side project, which he found exciting because it started as a silly joke and turned into a useful service that solved a problem, and it was something he could accomplish by himself.

Outlines

00:00

🚀 Founder's Risk and Investment Philosophy

The speaker, a business founder, discusses his role in introducing risk into the business and reflects on a tweet that posed a hypothetical investment choice between a guaranteed 7.5% annual return or the option to invest actively in individual stocks with no guarantee of returns. He expresses surprise that 40% of his followers chose the risky investment option, highlighting the misconception that individuals can consistently outperform market averages. The speaker also shares his own preference for the guaranteed return due to the significant risk already present in his business ventures.

05:01

🎶 Life Lessons from Playing Drums and Business

The speaker transitions from discussing his recent foray into playing drums to drawing parallels with life and business. He observes that beginners often grip tools too tightly, leading to fatigue and reduced control. This realization prompts him to consider the importance of loosening control in various aspects of life, including business management and parenting. He suggests that loosening one's grip can lead to better outcomes, allowing for greater finesse and adaptability.

10:02

🤝 The Art of Letting Go and Effective Communication

The speaker delves into the importance of letting go of the need to always be right, particularly in arguments. He contrasts his past combative nature with his current approach of seeking understanding and being open to different perspectives. The conversation touches on the idea of recognizing one's own fallibility and the value of not clinging too tightly to one's viewpoint, which can impede effective communication and personal growth.

15:03

🌱 Capitalism and the Business of Life

In this section, the speaker ponders the role of business in society, questioning why lessons from various fields often find their way into the business world. He challenges the notion that business is merely a drain for these ideas, suggesting instead that it could be seen as a conduit for manifesting dreams and ideas. The speaker argues that business, despite its flaws, offers a practical avenue for making an impact and turning visions into reality.

20:04

🔄 The Ebb and Flow of Entrepreneurial Enthusiasm

The speaker reflects on the different stages of a company's life cycle, from the exhilarating early days filled with uncertainty and potential to the challenging middle phase, often marked by a need for reassessment and maintenance. He acknowledges the emotional impact of these phases on founders, particularly the feeling of detachment that can arise when a company becomes self-sustaining and no longer relies heavily on the founder's day-to-day involvement.

25:07

🛠 Founder's Role in Injecting Risk and Innovation

The speaker identifies his role as a founder as one of injecting risk into the business, a task that becomes more crucial as the company matures. He contrasts the risk-averse nature of most employees with the freedom and necessity for founders to take bold, sometimes unorthodox, risks. The speaker shares his excitement about launching multiple new products and embracing a state of 'healthy off-balance,' which he views as a source of renewed energy and purpose.

30:07

🎉 The Joy of Side Projects and Independent Creation

The speaker recounts the experience of creating a website called 'Sam's List' as a personal project born out of a simple tweet. He describes the joy of turning a light-hearted idea into something useful and the satisfaction derived from independent creation. The speaker emphasizes the importance of maintaining a sense of fun and ease in one's work, even as one tackles more serious and challenging endeavors.

35:09

🤝 Navigating Business Partnerships with Transparency

The speaker discusses the dynamics of his business partnership, highlighting the importance of early and honest conversations about values, goals, and expectations. He shares the unique approach he and his partner took to align their personal and financial goals, which involved sharing detailed financial information and discussing their individual drivers and lifestyle preferences. This transparency, he suggests, has been key to their harmonious and productive partnership.

40:10

💼 Cultural Attitudes Toward Money and Success

The speaker explores cultural attitudes toward discussing money and material success, drawing from his own Midwestern upbringing and experiences with his family. He contrasts his family's reticence to discuss financial matters with his own approach to openness and transparency, particularly with his children. The speaker also reflects on the broader implications of these attitudes, considering their impact on personal relationships and societal values.

45:12

🧐 The Importance of Recognizing Luck in Success

In this segment, the speaker acknowledges the significant role of luck in his success, a realization that came with maturity and self-reflection. He recounts a past instance where he dismissed the concept of luck, expressing regret for that earlier stance. The speaker emphasizes the importance of sharing this understanding with his children, to ensure they recognize the role of fortunate circumstances in their lives.

50:12

🕵️‍♂️ Avoiding the Trap of Urgent Necessity in Learning

The speaker advises against the pressure to constantly stay updated with the latest trends, particularly in the fast-paced world of technology and AI. He suggests that the sense of urgency often promoted in learning new things is misplaced, as many 'must-know' topics may not be as critical in the long run. The speaker recommends a more reflective approach, allowing time for new information to be validated and for trends to stabilize.

55:14

📚 The Value of Historical Perspective in Biography Reading

The speaker shares his method of reading biographies alongside historical newspaper archives to gain a more accurate understanding of the subjects' lives and the context of their times. He discusses the importance of avoiding revisionist history and gaining insights from primary sources. The speaker also reflects on the common tendency for people to be wrong in their predictions and the value of patience in observing how events unfold.

🤔 Reflecting on Expertise and the Pace of Technological Change

In the final paragraph, the speaker contemplates the current landscape of expertise and the rapid evolution of technology. He expresses caution towards those who assert certainty in their predictions and advises taking a step back to observe developments over time. The speaker encourages a balanced approach to engaging with new technologies and ideas, rather than rushing to adopt every new trend.

Keywords

💡Risk

Risk, in the context of this video, refers to the potential for loss or danger in business decisions. It is a central theme as the founder discusses the importance of embracing risk in business, especially when starting a company. The script mentions injecting risk into the business as a way to drive innovation and growth, contrasting the typical aversion to risk that employees might have.

💡Guaranteed Return

A guaranteed return is a term used in the script to describe a situation where an investor is promised a specific rate of profit over time without the possibility of loss. This concept is brought up in the discussion of investment choices, highlighting the appeal of a secure financial outcome versus the uncertainty of actively managed investments.

💡Compounding

Compounding in the video refers to the process by which an investment grows exponentially over time due to interest or returns being added to the principal amount. The concept is mentioned to emphasize the long-term benefits of a consistent, guaranteed return, illustrating the power of compound interest in wealth accumulation.

💡Copywriting

Copywriting is the process of writing persuasive content, often for advertising or marketing materials. In the video, it is highlighted as a pivotal skill set that the speakers believe significantly impacted their business careers. The script discusses the importance of effective communication in selling products and ideas in a business context.

💡Innovation

Innovation is the introduction of new methods, ideas, or products. The script touches on innovation as a key driver for business growth, particularly when discussing the founder's role in injecting risk and the excitement of starting new projects, which can lead to innovative outcomes.

💡Entrepreneurship

Entrepreneurship is the process of designing, launching, and running a new business. The video discusses various aspects of entrepreneurship, including the challenges and rewards of starting a business, the importance of taking risks, and the personal growth that comes from entrepreneurial endeavors.

💡Investment

Investment, in the context of the video, involves committing money with the expectation of generating income or profit. The script explores different investment strategies, such as guaranteed returns versus active investing, and the psychological aspects of choosing between them.

💡Market Performance

Market performance refers to how well a particular investment or asset is doing in the market relative to a benchmark or index. The video discusses the difficulty of consistently outperforming the market, even for professional investors and hedge funds, emphasizing the unpredictability of market outcomes.

💡Hedge Funds

Hedge funds are a type of investment fund that pools capital from accredited investors and invests in a variety of assets, often using complex strategies. The script mentions hedge funds as an example of professional investment management, contrasting their sophisticated approaches with individual investors' strategies.

💡Luck

Luck is the occurrence of events that are beyond an individual's control and can significantly influence outcomes. The video discusses the role of luck in success, suggesting that it plays a larger part than many people are willing to admit, including in business and financial achievements.

💡Personal Finances

Personal finances refer to an individual's income, assets, and expenses. The video touches on the importance of transparency and communication regarding personal finances, particularly in the context of business partnerships and family discussions about wealth.

Highlights

The importance of injecting risk into a business as a founder, especially when compared to the risk aversion of other employees.

The concept of guaranteed returns versus active investment with potential for high reward or loss, and the surprising survey results regarding public perception.

The fallacy of believing in one's own exceptional ability to outperform the market, especially when compared to professional investors with significant resources.

The experience of visiting hedge funds and observing the stark contrast between the reality of investment work and the popular perception of it.

The idea that consistent, guaranteed returns can compound significantly over time, making them an attractive investment strategy.

The metaphor of loosening grip on the stick in various aspects of life, including business and personal hobbies, to improve control and experience.

The realization that as one gets older, it's healthier to mellow out and argue less, allowing for more open-mindedness and less tension in interactions.

The impact of the 'overview effect' experienced by astronauts, which can lead to a profound shift in perspective on the insignificance of many earthly conflicts.

The value of stepping back from the urgency of the moment to reflect on past predictions and the importance of not being overly reactive to current events.

The paradox of business being both a source and a sink for great lessons, and the importance of recognizing its role in manifesting dreams and visions.

The comparison between the early and late stages of a company's life cycle, and the different types of excitement and challenges each phase presents.

The personal struggle with the feeling of uselessness during the stable phases of a business, and the importance of finding purpose and action.

The role of a founder in maintaining a company's momentum by injecting risk and innovation, even when the business is stable.

The joy of creating something useful and having fun with the process, as exemplified by the creation of a new website, samslist.com.

The importance of transparency and shared values in maintaining a healthy and long-lasting partnership, both in business and personal life.

The impact of luck in success and the importance of acknowledging its role, rather than attributing everything to skill or hard work.

Transcripts

my job as a Founder it's to inject risk

into the business you can get away with

certain things that other people simply

can't because you own the damn

[Music]

place all right today's episode we're

going to talk about things that interest

us one thing that I tweeted out the

other day I wasn't surprised by this

result but it still made me sad I

tweeted out I said if you could

guarantee a 7 a half% real return for

the rest of your life every year

guaranteed but you can't invest in any

individual stocks forever however you

can start your own business and I think

I even said you can but you can only

invest $10,000 into that business or you

can invest actively you can't really buy

the index but you can invest actively

and do whatever you want some days maybe

or some years maybe you'll get plus 50%

some years you're going to get minus 50%

which would you choose option A or B 40%

of my 300,000 followers selected option

b and you replied and you said option A

all day easy what why did you select

that well to get 7 7.5% like with no

effort and you're

guaranteed it's a no-brainer it's an

absolute no-brainer for me I mean um now

I've got a business I have a lot of risk

in my own business so that might be part

of it as well like I don't I have all

the risk there so let me ask you this

were you intending this to be like

someone who's 21 years old straight out

of school never invested before has

nothing else going on or is it just like

at any point in your life I think at any

point in your life that's still the

right decision I still turn that switch

on in a second yeah that's a ridiculous

return uh in a good way uh and a

consistent return I mean the way that

would compound over time would be

fantastic and there's nothing boring

about that that's an incredible I mean

it's boring actually but also an

incredible thing so yeah would you think

that the the the survey was going to

produce did you were you surprised by

The Ratio or I'm surprised that the

average Joe I mean and my followers are

probably above the average showe in

terms of income maybe IQ maybe not I

don't know but for they're they're

typically a higher good looks for sure

they're they're up there they're very

goodl looking it's a very high like I

would imagine it's a high educated

castal uh crowd and and so anyway I I I

would have thought that they would have

seen the fallacy that they probably

can't beat all the others particularly

the other people who have a much better

advantage and so the idea that although

everyone else fails at getting this

return I in my little office in

part-time with just me can somehow beat

all the others and I and I thought that

that was shocking to me that that they

thought that they were exceptional at

that that's what I was surprised at yeah

well that's pretty common I think

everyone thinks they're exceptional in

some way I mean the thing people don't

take in into consideration is is is uh

is risk so like they they might go well

if I just buy Nvidia or apple or

whatever Shopify I mean and the thing is

in the short term you almost certainly

can over the next two or three years you

get lucky pick one pick a winner but the

rest of your life that's the question so

here's what I've done lately I've been

spending time in New York because I've

got family here and I cold emailed and

did cold Outreach I randomly met a bunch

of people who work at hedge funds and

I'm like hey like I'm not like a

competitor you don't ever have to worry

about me I'm just like a a passionate

interesting uh interested person can I

just like see your office and just like

can I just sit at your computer and you

just show me your software and like I

just want to see like what you do all

day and you go to some of these offices

and you know I would have thought like

they were like Wolf of Wall Street where

it's like buzzing and like the phones

are ringing it's really just a bunch

it's pretty quiet and it's usually just

like a bunch of nerds like looking at a

computer screen but they got like four

screens and they've got like incredibly

complicated software and the average

show is getting paid hundreds of

thousands sometimes tens of millions of

dollars to be good at this one thing and

then I think about like how is like

Bobby Lee in whatever Missouri where I'm

from on his Robin Hood app possibly GNA

have like an edge on all these resources

and these people with all these

resources they're still not that good

you know I talked to a guy who worked at

Bridgewater recently and I was like

bridgew I've read up raid doio aren't

you guys like the best he's like

sometimes we're the best but the last 15

years we've sucked we've underperformed

the market and I'm like that's insane

that 1500 employees tens of billions or

hundreds of billions under assets you

all paid like the best there is you

still can't beat it and so that kind of

like that's kind of where I'm coming

from yeah it's also like Vegas you go to

Vegas and you know you you're on a hot

streak for for 30 minutes and you know

the longer you play the less you're

going to win you're going to lose like

that you're going to lose the house is

going to win over the long term so

people I think have this idea of

short-term performance in the market

feeling like I can I can do this forever

just like in Vegas you can't do that

forever and you will begin to lose and

the same thing is true in the market so

yeah lock it in what's this thing about

loosening the grip on the

stick oh yeah so I got I got a drum set

recently I I used to kind of want to

play drums I kind of did for a little

bit I stopped for many years and I kind

of just picked it up recently my office

is a bit of a mess so I got to find

better place for but right now it's in

the

corner and as I've been playing I I I

been I learned this very quick lesson um

and actually it's true when I try to

learn how to play guitar I say try again

because I'm I'm not very good at these

things but I I enjoy them is when you're

new at something you tend to hold things

too tightly like I I hold the drumstick

too tightly I hold the neck of the

guitar too tightly anyone who's played

any instrument will understand kind of

where I'm getting where I'm coming from

here I used to play drums I know what

you're talking about okay so you you

hold the stick really really hard and

then you fatigue faster you don't have

as much articulation on the stick you

can't get certain ghost notes and tones

out of things because you're always

hitting too hard and too firmly and you

just there's no finesse and it kind of

dawned on me recently that um this is

very very true for most things in life I

think especially business I kind of some

ways I feel silly always bringing this

back to business anyway I realized that

like by simply loosening my grip a bit

by lightening up um you end up having

better control you end up playing better

you end up working better you can do it

longer um and you allow other things to

happen that weren't possible when you're

gripping so tightly I think this is true

for business I think when you're

starting a business you have a really

tight grip on things typically and it's

best at some point to loosen up a little

bit and let the rest of the organization

expand into itself versus you trying to

control every last thing and I run into

a lot of entrepreneurs who I think have

not learned how to let go of the stick I

think that that's also a young man's

thing to do right like you learn this

with age

what are you saying what what you what

are you trying to say well what I'm

saying is you you have a couple decades

of uh of experience and and like and so

do I and I think that as I'm getting

older which I'm not old but neither are

you I'm learning it is okay to loosen up

that's what they say a lot about uh men

they say oh well he used to be intense

but he's mellowed out he's mellowed out

and that's usually what they're

referring to yes that's a good point

yeah the mellowing out um it's nice

though in in a different realm of

something to to find a metaphor and in

my head now I am kind of thinking about

this like loosen like loosen up your

grip a little bit and what parts of life

well I'd say business I would say also

like with my kids a little bit I

I I would say there's a way where I I

kind of wanted wanted them to do certain

things a certain way and I and it just

it it creates this conflict like they're

their own people I'm my own person um

and you know I want to encourage them to

do certain things in a certain way but I

also got to loosen up a little bit

around that and let them find their own

way um and that that's something I kind

of learned pretty early in parenting um

uh so there's there's a lot of things

but I just in general I just feel better

when I'm not gripping things so so

tightly and um when I look out there uh

you know on on Twitter or or anywhere

LinkedIn or whatever and I'm I'm looking

at these like business stories there's

just I'm I'm reading a lot of grip I'm

reading a lot of tension uh that that

you know people are trying to op over

optimize and paying attention to every

last little thing in a way where I feel

like just loosen up a little bit like

pay attention to a few things that

matter and let let it let things just be

a little bit more all right look the

question that Sean and I get asked

constantly is what skill set did we

develop early on in our careers that

kind of changed our business career and

that's an easy answer it's copywriting

we've talked about copywriting and how

it's changed our life constantly on this

podcast and we've give a ton of tips a

ton of techniques a ton of Frameworks

and throughout all the podcast well we

decided to aggregate all of that into

one simple document so you can read all

of it you can see how we've learned

copyrighting but you can see the

resources that we turn to on a daily

basis you can see the Frameworks the

techniques we use it's in a simple

document you can check it out in the

link below all right now back to the

show the best example that I've

experienced this in my real life is

arguing with people and so before it was

like every word that I like what I

learned to talk it was like it was fight

was the first was the first thing that

came out you know like my early words

were I wanted to fight and so if I met

someone with a different political uh

perspective it was you're wrong for

these reasons that you're really stupid

for that um when I lived in San

Francisco I I was it was I was

significantly more combative than I am

nowadays as I uh I've been lucky that I

was raised in Missouri and that I um

lived in San Francisco lived in New York

lived in Texas and that has shaped me a

bit politically but also that it it

bleeds to other points of life which is

like instead of someone saying something

when someone says something that I

disagree with it's more so instead of

fighting it's uh well why do you feel

that way uh that that's that's a really

interesting perspective tell me more

about why you feel that way and I think

I I don't know if this is just a

clickbait thing but Kiana Reeves had

this quote where he was like I used to

argue with people now I never argue you

could say one plus one equals 5 and I'll

say well I hope you have a really good

day um and and that's a little bit about

how how it's been where I I just want to

argue a bit less and I I'll still catch

myself arguing but uh Dale Carnegie in

this book how to win influence to how to

INF Win Friends and Influence People

he's got many famous lines but one of

the famous teachings is basically just

don't argue with people because you no

party typically walks away happy or

satisfied and so loosening the grit for

me is arguing less where it's I'm not

even going to judge you and I'm just

gonna I can recognize that you think

this way and I think this way and it's

cool it's a great example actually uh I

hadn't thought about that but that

that's another great example of just

like holding on it's not even holding on

too tightly to a perspective because you

you can have a perspective that you

really believe in but it's it's it's you

know it's like don't clench where you're

not even able to listen you know I think

the the point about like being too uh

grippy is is you're you're you're it's

like you're a spring under tension and

if someone says something to you that

you disagree with like you're going to

Boom expand and like explode right which

is kind of what an argument can be

versus just already taking some of the

tension out of that spring and just like

bouncing with it listening versus

exploding out of it I think that's a big

difference have you ever read there's

there's this term I'll have to figure

out what the term is but there's this

term where astronauts go to space and

they see the Earth from far away and

many of them have reported to have a

lifechanging perspective where they

think to themselves the fact that we're

fighting over religion is ridiculous the

fact that we're fighting over borders is

ridiculous now let's Zoom down to the

smaller things the fact that we're

fighting over someone saying something

rude to us is absolutely crazy because

we're all just a bunch of monkeys on

this like floating thing and it's like

monkeys with cars we are yeah and we see

like this this abyss and then we're just

this silly blue thing in the middle of

it and and and it's like a lot of

astronauts say it changes their

perspective and it Mellows them out and

I think that when I read about that

years ago it kind of helped me calm down

a little bit more to where you think not

this the stuff that I thought mattered

doesn't matter for example I remember

when Co happened and I was like we're

never going to a concert ever again and

then three years later I'm like [ __ ]

that I forgot all about that do you know

what I mean totally have you have you uh

to that point about astronauts have you

um read that great passage from Carl

Sean the pale blue dot what's he say no

I mean it's one of the most beautiful

I'm not going to say it because I want

you to read it I want you to have the

experience of read it's short it's a

paragraph it is one of the most

beautiful passages I've ever read but

it's it's exactly kind of what you were

talking about with the astronauts like

looking back at the Earth it's all about

all the things that have ever happened

I'm going to really generalize here cuz

I want you to read the words but all the

things that have ever happened every

leader every religion every point of

view every argument every whatever right

beautifully in beautiful Pros happened

on this Speck of dust basically I think

he calls it like a moat of dust it's

such a beautiful passage and it brings

tears to my eyes and I try to read it a

few times a year because it's so

right it's so spoton right and it's

exactly what you're talking about in the

most beautiful poetic way which is all

the stuff that we're worried about all

these things like very few of those

things matter although of course they

matter in your day-to-day life so like

they're real for you but they really

don't matter that much and it's just a

good reminder that you know all the

things we're just so fired up

about who cares well it's a it's a

paradox of like caring by not caring um

why do you not like comparing this up to

business and I'll afterwards I'll tell

you my reason why I think it's good yes

so this is an undeveloped thought of

mind that's been sort of on my

mind and I don't know if it's a good

idea or not so just run with me here I'm

gonna I'm going to kind

of this is undeveloped it seems like

every great lesson is then applied to

business by someone so for example a

Navy SEAL learns all the stuff in the

military and they come and they like

then consult for companies about how to

like run teams or some great coach coach

is a great team and then they come and

they bring it to the business world it's

always like bringing it to the business

world and I'm like what does the

business World deserve the best lessons

from things that are completely

unrelated in many ways to business but

why does it always come to the business

world and the main reason is why in my

opinion is because the business World

pays for that advice it's not that it

deserves the advice it's not even that

it's advice that's applicable but that

it pays for the advice and the way I've

been thinking about it is not as this

this this this shining beacon on a hill

that business deserves all the greatest

things but actually as the drain that

all these ideas drain down through

business because business sort of just

is willing to pay for it uh and and

listen to it and sort of have this this

this um it's sort of insecure in a way

so like it's it wants to listen to the

Navy Seals it wants to listen to the

great double or n NCAA coach it wants to

listen because it it's insecure in its

own way um and also there's this there's

a sense of like um these other places

and people they know better than us so

we're going to we're going to just you

know bow down for their advice and I

don't again this is a little bit

unformed

but it's something that just bugs me a

little bit I don't know does that make

any sense or is it is it is this a weird

idea no it makes sense but my argument

would be instead of the image that

you've had you've just painted is you've

painted a upside down triangle with all

of this beautiful stuff draining down

into this bad thing thank I would turn

that turn that upside down and say it

all is going up to this amazing thing

and here's why because I think that

whether you like capitalism or don't

like capitalism you cannot deny that

it's here to stay at worst it's here to

stay in the lifetime of everyone who's

alive maybe America will change maybe

maybe the rest of the the majority of

the world will change but I I I wouldn't

bet on that happening anytime soon

therefore I think that capitalism and

thus business building is the most

practical way to manifest a dream or a

reality and often times you could say

well what about art and I would agree

with that but at the end of the day

you're still making stuff that people

want and you're still selling tickets

you're still trying to make some type of

money off of your art so you can

continue doing it or you're just going

to have a rich person who funds you so

you are are able to do it and so my

opinion business is the most practical

way to actually kick a dent in the world

or to manifest a vision and so I think

of business as a very P like I'm very

passionate about it being a little bit

of a spiritual journey of like turning

dreams into reality that's an optimistic

point of view which which I I do

understand here's my

question if this thing called business

is absorbing all of these

lessons from all of these other Realms

right and they're all like either

filtering down or filtering up but

they're filtering

too and maybe I'm wrong about this but

why aren't the Navy Seals asking CEOs

for

advice sometimes they are if you look at

like I don't maybe they are like uh Jack

Welsh's book Six Sigma like a lot of

different types of organizations outside

of business like view that book I don't

really like that book but they view it

as like the rules of the game yeah okay

yeah I might be uninformed in in a sense

of like what who the military is

listening to and who you know sports

teams are but there's something it's

like you would imagine this this this

entity this business thing that has

absorbed everything would then be the

definitive source of this wisdom but I

wonder is it a one-way Street or is it a

two-way street and it seems I think

you're more right than you are wrong

that's for sure it's definitely more one

way yeah no I just wanted to give I just

wanted to give one example but I was

frankly that's a nitpick example totally

I I don't I don't know again I don't

know if this is a good idea or not it's

just it's been sort of floating in my

head for a bit so I it's fun to air

these things out what was more fun early

days or late days of the company oh man

that's a really good

question

um they're very fun in very different

ways so I me it's a bit of a cop out but

it's it's true um but they're fun in

different ways what's exciting about the

early days is there's a certain energy

that you can never capture again which

is the the there's so much more unknown

like you're you're you're go you're

starting from zero and you're building

something and you don't know where going

to be and where it's going to go and

what's possible and what isn't and how

long it's going to last and all those

things now you don't know how long it's

ever going to last in a sense but

there's this there's this hope there's

this possibility there's this birth and

you know it's like boom we're out in the

world and here we are and this is an

incredible thing and that's super fun

and then you get a lot of new attention

and you're kind of burst on the scene

and that's exciting really exciting um I

think what's what's hard actually is the

middle we've gotten to a place now being

having done this for 25 years it's

become really fun again in a different

way but I would say like 15 years in is

a different story uh because that at

that point it's like we've been doing

this for a while I don't know how much

longer it's going to last like you're

kind of in this sort of Maintenance

thing um were you big enough at at 15

years where you're like like payroll is

not an issue like were you out of like

any type of uh uh outside pressure where

it was like things are fine I so it's

like I feel weird that I have I'm

complaining but this feels weird yeah

and I'm I'm not really complaining about

it but yeah yeah it's more like you know

Scott SC Scott bsky wrote a book called

the messy middle yeah I have not read

the book actually but I understand the

idea of it and it's kind of what I'm

trying to get at which is like the

middle of it is it's like what do we

want to be now and and where do we want

to go now and are we going to be a big

company are we going to stay a small

company there's all these opportunities

that are surrounding us now and swirling

around us versus when you're starting

you're just like you're just going

you're just moving then you get to this

play place where

like kind of evaluating and now we're in

this place where we're just sort of

mellowed in a sense to your point

although we're actually getting very

ambitious again because we have the

sense of like we've been doing this so

long now that like if we took some crazy

bets or made play some crazy bets and it

just totally all fell apart like I don't

want that to happen but I'd be okay with

that too like we're at the place where

it's like we've done plenty and we've

had an incredible run and if it all

ended with a bang because we tried some

crazy stuff that didn't work like I'd be

okay with that too so I feel like I'm at

that place now where I wouldn't have

been at 15 years that makes any sense

what's your sense I mean you started a

bunch of stuff my sense is that um so

none of my things have have been as big

as yours but they've been big enough

where we've had dozens or you know 50 60

employees and it it we got outside of

the like existential crisis moment where

it's like things are working

my and everyone talks about focus focus

is a very common thing and it's

something I I firmly believe in but as

someone who likes to make things for my

skill set a company outside like maybe

let's say 3 million in revenue or maybe

maybe five million in Revenue I've

noticed consistently a five million in

revenue and like 15 employees something

like that I'm like I don't know what to

do with my hands like I'm just sitting

here like what how do what do I do I

feel useless and I feel like uh

sometimes a general behind the scenes

just pointing

and I've noticed something that I I I

really dislike but I think it's normal

is a company es and flows and I've

noticed that this EB and flow carries

over to the rest of my life where uh I

just had a child and I'm like I'm in

this uh quiet time for a moment where I

have to be present whereas there's other

times where you're dating or something

like that and you're like I'm in I'm I'm

in war mode a little bit where it's like

there's it's action constantly or like

I'm on top of my game and I got to be on

top of my game same with business where

it's like we're launching this new thing

we're we're out fighting uh with the

troops we're in the trenches and then

there's other times sometimes this I

think can last for years maybe where

it's just like we're just doing the same

thing over and over and over again and

that period can be a little depressing

even though everything is going well

it's a very saddening period because you

lack action uh it's basically like what

they say with a lot of great investors

uh I think uh uh Manish said this on our

uh uh paba on our last podcast he was

like if you can watch paint dry you're

going to be a good investor the problem

with that for a lot of in uh a lot of

entrepreneurs or a lot of like

go-getters is that's a really sad place

to be in even though everything is going

well it's really uncomfortable to be in

that feeling and so have have you guys

had a lot of have you had a lot where

you're like man I just got to kind of

unfortunately have to do nothing for

maybe years yeah I can totally identify

with that and I think I think what

you're getting at is with entrepreneurs

is that what you're describing is in the

early days you are very important as

founder yeah then there's a point where

you build an organization and then the

organization is able to in some ways in

a good way run without you to some

degree and at that point you kind of

feel a little bit less valuable yeah to

your own thing that you made it's a good

thing but for you it's a good thing

because it means there's some stability

and you're not the bottleneck and you're

not the only person that matters here

anymore obviously but but for you

personally it feels a little bit like

you've become detached from this thing

that you made and you you're now further

away typically from like the the the

creation phase and now you're more in

the maintenance phase of something and

and you're dealing with internal

politics and personalities and hiring

and you've got some great people who

just left and now you got to find new

people and the culture is changing and

like that's a pretty tumultuous

turbulent time for a founder and I've

gone through that many times um and it

it it comes comes and it goes what I

found

is that what I kind of discovered

actually recently is that my job as the

founder I'm still a Founder I still

started this company I'm still in it 25

years my job as a Founder what I've

realized is is it's to inject risk into

the business most people Everyone pretty

much at your company's job is to manage

risk to some degree to keep their job to

not push too hard or too far

ultimately um you can get away with

certain things that other people simply

can't because you own the damn place you

are the original person so what I found

a lot more joy and and um and excitement

in is is revisiting this idea of

injecting risk and for us that means and

by the way I I don't think you could

change that I think like for a long time

I was like why aren't these people

taking risks I got to force them and I'm

like it's impossible that's impossible

to change even if you hire a great great

CEO to replace you as CEO like they're

they just don't have that they they

might be Inc an incredible see CEO great

executive executing things trains are on

time incredible but there's that thing

that's present in a Founder simply

because they were there from the

beginning that they they have an extra

ounce of it's not even that they're

they're not better than they just have

an extra ounce of latitude that allows

them to take risks that nobody's going

to say no to maybe if you have a board

maybe someone's going to say no but

they'll still give you more latitude

than a Hired Hand basically in a sense

so my my sense is the way I found to

return to this sort of Flow versus the

the ab is

like is to inject more risk which for us

means we're going to build a lot more

products like this year we're going to

do four products we're going to we're

going to begin we we're about to start

working on two products simultaneously

which we've never done before um we've

never built two things at the same time

and like this there's a lot of stuff

going on we got different models we got

once we got SFS we got all these things

we're going to do multiple versions of

multiple things and different different

business models and we're we're going to

we're really off balance in a really

healthy way at the moment um because

like we're doing a bunch of new stuff

and that gets me excited now it makes

some people internally nervous

understandably so it's like well this is

different now we're kind of off balance

a little bit and we're trying new things

but that's how I have to run the

business um otherwise I will become

bored and at that point um it won't

serve me or the business well if I'm in

charge and board that that's not a good

good that's not a good thing for my

professional life or for my main company

that's like the main 9-to-5 thing um for

Hampton I've not I do inject rist but I

have a CEO and so uh I try to I have to

like respect uh I got to respect that

relationship and so yes on my nights and

weekends I um I created a new website

for fun I created this website called

samslist it's samslist doco nice and the

reason I did it was I tweeted out like

who's got an accountant that they love

because I just needed an accountant for

something I got like 300

replies and I was like wait something's

interesting here because this tweet got

so many bookmarks like a lot of people

bookmarked it and someone was like oh

I'm saving this for later to find an

accountant so I was like this is

interesting so I spent a few months

calling every accountant on the list

finding out how much they charged what

services they provide what services they

don't provide who the ideal client is

who isn't the ideal client whatever and

then I created a website called Sam's

list where I reviewed or I uh like put

all the information from all my research

for all these accountants created this

website I think I got 8,000 people to

come in the first week and then I uh

started figuring out how to monetize it

and so this month the first month that's

been live it's May 22nd when we're

filming this I think it's done 20,000

this month and the $20,000 that I've

made from that is more dopamine than

let's say a million dollars a month or

two million a month that I've gotten

from other things it's a total rush and

I love it why is it why do you think

that why do you think that's so exciting

for you it's a total rush because what

started it's so fun it's so fun for

things that start as silly jokes like uh

like just stupid like the calcul like

the the logo that we have is a

calculator that has three numbers and a

Q and it looks like clippy it looks like

clippy from Microsoft like waving at you

it looks like Mickey Mouse and I just

used chat gbt I said make a logo that

looks like clippy but it's a calculator

and it's so fun to take silly jokey

stuff and turn it into real things that

actually solve problems and I find that

to be almost like part trolling part

like [ __ ] eating grin like scheming like

I love that like isn't it would it be

hilarious if we made this a thing and

then actually seeing it become a thing I

find to be so exciting uh I also think

that when you're when you have a idea

even if it's like a serious idea and you

start seeing customers truly like it

that's a very invigorating feeling it's

the best and we we have this internal

saying we don't say it that much we we

I've said it before and we kind of try

to feel it which is that cool wears off

but useful never does and what you've

made is something that's useful and that

is one of the most beautiful things I

think you can do for Humanity is to make

something useful um and and to have fun

with it and to screw around and not like

take it so seriously this is going back

to thing your your grip is loose on this

you know you're having fun with it you

ask chat GPT to make a logo and you're

goofing around the name is just your

name it's like it's just have some fun

and and it's a reminder that that's what

this should always feel like as much as

possible it is totally valuable to do

hard things absolutely but not

everything should be hard there should

be plenty of easy things in your life

too things that flow things that you

have fun doing things that don't feel

hard you don't need to pile up and

collect only hard things and so while

some of your business ideas might be

harder to pull off for other reasons

this one is so light-hearted and easy

it's healthy it's good for you and you

ReDiscover like why you do this sort of

stuff and it's also fun I think there's

something probably I'm guessing there's

something probably in this that like

you're like I did this by myself yeah

that's like the feeling of

accomplishment and go I you know I can

still I can still do something by myself

like really by myself and that's useful

is is is very rewarding and and hard to

come by sometimes when we all think we

need to have partners and co-founders

and teams and stuff to pull things off

do you and your partner get along like

beautifully we get along really well

we're not like we're we're friends but

we don't see each other very often we

live in the same town and we don't see

each other I see them once every I don't

know couple months we're very good

partners um and we're friendly but we

just don't we don't hang out like our

families don't hang out um not that we

wouldn't enjoy it we just like we just

don't there was um there was a a study

where they looked at uh the most common

uh reasons why couples get divorced the

most common reason was contempt and the

most common the most common reason for

divorce was contempt the most common

reason for staying together was you

admir the other person ah I hadn't heard

that but it resonates like resentment is

just bad and I think a lot of business

partners resent each other actually have

you you've been in business with others

I'm assuming yeah I've got uh the most

I've had bad relationships I I'm

currently in a very harmonious

relationship with my co-founder Joe that

I could see lasting a lifetime what

feels different about it so when we

first started together we uh we we

invested in startups together and we had

a great time and he previously helped me

with uh my old company the hustle I cold

emailed them and he was like Hey if

you're in New York tomorrow just stop by

the office and we could talk and I was

like yeah I'll be there and I like flew

out there and like hung out with them

and uh that's how we became friends and

then we invested in startups together

and then I was like I took like a really

formal conversation with them I was like

Joe I love working with you um something

I did with my wife early in our

relationship when we were like thinking

like hey is this something that we want

to like make real and like get married

and have a family and I sat down with my

wife and I was like let's just like walk

through our life values and like what

type of Life do we want to have and

let's see if like they kind of align and

that's okay if things change eventually

but let's just say let's just see if the

direction is is is similar and so I sat

down with Joe and we said uh hey let's

just outline like what sacrifices are

you willing to make what sacrifices are

you not willing to make what's a perfect

day look like for you what are you

driven by and like for example for me I

was like you know I'm driven by ego like

I it bothers me that people think I'm

not good enough so like I always want to

prove that I'm uh as good as I think I

am or I'm driven by money uh I was like

I work only 40 hours a week I don't

really want to work more than that um

I'm not willing to sacrifice traveling

um I'm not I'm not going to like get out

of my house often if I have a family and

he like named all of his things and we

looked at the all the things and we're

like how much money do you want to have

how much money do I want to have we

looked at all of the things and we're

like uh for everything that is agreed

upon awesome for everything that's not

agreed upon do we think that that's like

a deal breaker and we they weren't and

we were like cool we like did a really

good job of being very honest upfront

about our wishes and now it's much

easier to address like any issues we

have because it's like hey you uh he'll

be like hey we got to get this done and

I was like Yeah but I but but he'll be

like uh but you told me that you don't

want to like grind on a Saturday so I'm

not even going to ask you it's all good

we we agreed to this uh things like that

and that makes the relationship really

nice um is that we uh respect one

another and we had those conversations

super early on do you feel like uh um

the list or the conversations you had

about that

um turn out to be true like are those

really the things that that that you

guys share together or is that sort of

what you imagine iMed you would share

yeah for example for for the money let's

just do the money one that's a really

easy one we actually shared each other's

personal finances with each other and

interesting yeah we were like super

transparent we're like here's all of our

finances uh what matter like I would

like to go here one day where would you

like to go it's like all right well to

go there we're going to need like let's

say that my goal is less than your goal

let's hit your goal then and if we need

to hit your goal here's maybe what the

numbers would need to look like and

here's what we'd have to make so like

that you know is that like something we

both agree upon do you know what I mean

like we were very transparent with each

other that's wild I mean this is I know

you and I were talking on Twitter a

little bit about like how I'm super

uncomfortable talking about money and

you're like sharing your personal

finances with your founder and kind of

it's it's interesting you don't do that

with your partner you don't do that you

don't do that with your partner like

well you guys your guys' finances are

probably so tied together but you know

they are tied together I mean yeah

basically all of our you know

essentially the vast majority of our net

worth is tied into our business so we

know what our distributions are and all

that stuff but yeah we don't I we don't

talk about that ever um but um it's

interesting like I also like you're

midwesterner I'm a Midwestern like I I

feel like my my thing is like don't talk

about it I don't know why like it's

ingrained in me were you were you like

that a one point or and did you change

or I was always open about it because I

saw my family like that and I was like

that's so unhelpful for me because

you're not telling me you're not giving

me a road map you're not I don't have

anything to strive for because I don't

even know what's possible my father

owned a produce brokerage company which

like uh it's like a small business but

they sell like let's just say over the

course of his 30 or 20 year career he

sold like a $150 Million worth of onions

but like I'm like how much is a lot of

Buddy is a lot of Buddy like 50 Grand a

year or like $300,000 a year like I I

have no I have no clue about this and so

I and I always regretted that that they

weren't open with me so I was like I'm

just GNA be open about it it's so

interesting my my folks never talked

about money I don't still to this day

don't know if

they're middle class wealthy I don't I

don't really know you're kidding me do

you really you have no idea that's weird

do you support them I have supported

them I I gave them a big chunk of money

at one point but um they they like

regretfully took it they didn't really

want it um then I don't think they need

it and I think I'm going to get it back

when they pass kind of thing like

they're not going to use it you know

they've always been very frugal um we

don't talk about it my dad was an

entrepreneur worked for himself like a

small business owner he was a Trader so

he traded stocks on own uh he wasn't a

broke I think he started out as a broker

for a little bit but then he was on his

own individual investor basically I

think he did well for a while I think he

didn't do well for a while I think you

know that's that's a tough road in a lot

of ways um he wasn't a day trader but

there wasn't anything we couldn't have

but we also didn't strive for anything

that we couldn't afford it just I don't

really know parents have always been

careful with this so I I kind of

absorbed that like just don't really

talk about it and um it didn't limit me

though it's not like I I just felt like

we we were everything was sort of fine

as how it felt to me what are you going

to do with your what are you going to do

with your kids I struggle with this um

like my parents never really talked

about it we we don't talk about it but

we certainly act differently than I than

my parents that growing up you know we

own a few homes um you know we've a

couple nice things you know so it's like

it's it's it's kind of obvious that like

we can afford things um and do things um

but uh we just don't we haven't talked

about it I think that's that's an

incredibly Midwestern and a incredibly

uh more traditional older set of values

um my family had very Midwestern values

and I think a lot of those values are

great hard work don't complain um don't

don't make people work for you like uh

like I remember going to like a

restaurant and like we ordered a pizza

and they brought us like a chicken salad

and I'm like yeah we're not going to

we're not going to inconvenience you

whatever just give me it uh like I will

eat that exactly yeah that's like ude

I've never sent a dish back in my life

not a million

years steal whatever it's fun yeah and

so like I actually think some of those

values are great I think there's many

other values that are like I don't like

using this word because it's too loaded

but toxic bad uh there are a lot of

values that are bad for example I think

the stoicism that midwesterners tend to

have that you definitely have I think

that it's gotten you to where you want

it to go in a traditional success uh

perspective but also like not being

trans parent with certain people I think

I just don't want my family to be left

wanting more when I'm gone in the sense

of like I wish that they were more open

with me for example I've not seen photos

of my family really when they were

younger or like I don't have any your

parents you mean yeah my parents when my

parents were younger I'm like and I

don't even know their grandparents' name

I don't know I had to do 23 in me cuz

I'm like when I asked them what my

Heritage was they would just go we're

white I'm like yeah yeah okay but what

flavor like come on I need some more and

so or or I had to do ancestry.com in

order to understand like who my

grandparents were like what are you guys

hiding and I turns out I found out that

an uncle is actually uh my grandmother

was married previously and I'm like why

didn't you guys tell me this and they're

like oh we didn't want to bring it up

you know like little things like little

things like that and I'm like that's

weird just like just discuss it just

just tell me yeah yeah that's weird uh

so anyway I think that is actually bad

though and I pray that I don't fall into

that into that trap and so that's why

with my family I've been overly

transparent with a lot of things uh and

I just think that that like lightens

lightens things up a little bit I admire

that actually and and this is something

I actually also admire about David um

I'm sure you wouldn't mind me telling

you this um David used to when we were

in Chicago uh when we had an office he

used to drive to work in like incredibly

fancy cars yeah and my Midwestern

sensibility is like dude don't do that

he's like why not

like my sense was like it just it sends

a weird message and he's like he's like

what's the message I mean everyone knows

like everyone here who works like they

know we're doing well like why why would

I hide that from I agree with you on

that one by the way um and and I I I

it's so funny because he's right I think

have you seen the big Labowski he goes

you're not wrong dude you're just an

[ __ ] so like in my mind I'm like I

but I still struggle with it just

because of how I was raised and how I

was brought up and and and and and the

imagined messages like the whole point

is like I'm imagining that everyone's

looking at that and going what an

[ __ ] what it's like most people

probably don't care they don't care they

know this they know the score they're

fine with it and if they're not that's

their problem like David's point is like

if they have a problem with me driving a

nice car that's their problem it's not

my problem like I've earned this I enjoy

this car I buy this car because I I like

the car I'm not going to hide the car

and he's he's right but I I just have a

hard time with it still not anym with

with him this is like way back in the

early early years um but but it still is

something that's in there there's a

residual like struggle with that degree

of honesty around money in a similar way

that people like you know iner like

who'd you vote for like I don't talk

about who I voted I think Chris Rock has

a great bit on that it's it's so funny

um like when I see someone with a with a

political bumper sticker on their car

I'm like you're insane you're you're a

crazy person yeah and they're probably

like why I like this guy I like that guy

I like her like what why why am I have

do I have to hide my point of view and

they're right too you know so deep down

your point of view is healthier I still

have a hard time with it not and that's

probably my problem or may maybe it's

not I don't really know I don't really

know it's very interesting do you want

to change or do not care well I think

the truth is my kids have a or at least

my son who's older my daughter's five

she doesn't recognize any of the stuff

yet but my son does and my son's really

into like he seems to be into expensive

things he like has this craving for

expensive things so I mean he he's got

to know what's going on to some degree

he's not an idiot um do I want to sit

him down and go hey son we've got this

and we've got that and like I that isn't

how I would handle it it'd be more like

I've worked hard here's what we have we

have some things we're going to enjoy

these things we share these things with

friends this is not just our stuff um

and that's kind of how how I how I treat

for

example the house thing when I renovate

a nice old house and and I make it

better like it's our house but it's also

all of our friends house they free

people are free to stay there as much as

they want visit as much as they want I

have this property in Wisconsin This Old

farmh House 160 Acres it's beautiful

piece of land I've been working on it

for years my friends use it more than I

use it I don't use it anymore I'm not

even around there my friends can just go

up there whenever they want and use it

so it's it's about like we're fortunate

clearly fortunate and lucky and a big

part of this is you want to share these

things this there's there's you're not

fortunate if you hoard the things then

there's something I think kind of wrong

about it in from my point of view so

share as much as you can share these

experience with other people and uh and

and we're fortunate you know that's kind

of how I sort of left it at this point I

don't know we'll see um the the thing

that I tell my uh friends and family um

is I try to let them know I don't I and

this is something that I couldn't grasp

earlier on in my career I refused to

admit this one thing which was luck is

real and it has played such an important

part

of any type of financial uh uh like just

meeting the woman who you spend your

life with like just the fact that we are

in the same place at the same time luck

is such a bigger component than I ever

would have been willing to admit years

ago and I think and I think that what

I'll explain to my children is like look

I worked hard but I frankly didn't work

harder than many other people that's

right I'm smart but I'm not that much

smarter if at all than the average

person the truth is is that

I worked hard I had a skill but I got

like 50% of luck was like was like part

of that or maybe even more than 50% luck

is such a hug huge component and I hope

that I can uh put that on my family to

realize that luck was real it just

happened to work out uh because some

timing thing worked out like let's say

you started a business and you surged

during covid you're like dude I just

kicked ass cuz something I had nothing

which I did our business killed it

during Co I'm like I didn't know that

was going to happen that was just total

luck or you know what I mean like things

like that it's it's absolutely real and

I need and I hope my family will

understand that 100% with you and I

think it's way more than 50% I mean all

the way back to you didn't choose your

parents you didn't choose anything right

you didn't choose your mind um how' you

become the kind of person who is the way

you are like there's a million inputs a

billion inputs that you don't know about

all the

things one of the I don't regrets too

strong a word but one of the things I

regret most most in my career is getting

on stage at startup school so this is

like um y combinator startup school

years ago I forget when I was invited to

speak I was only invited once because I

was pretty anti- raising money yeah I

was say I thought I thought you're like

the opposite of their ethos I was but uh

Paul was kind enough to ask me to come

up on stage and and give a talk but you

and Paul seem quite similar to be

honest well I appreciate that I mean I I

have a lot of admiration for his ability

to to put is together and and think

things through what he's built um but he

invited me on stage and there was a

question from the audience about luck

someone's like do you believe in luck

I'm like hell no I don't believe in luck

wow like and I was such a prick how old

were you early mid 20s mid 20s I think

it was whenever it was and I was just

such a prick but a young punk prick you

know kind of

like and and it's so embarrassing but

you know like a lot of things are you

look back on like poetry you wrote in

college like oh my God I wrote that or

whatever like whatever it is you know

and and and you know it's like you just

realize like that's part of growing up

is is is totally misunderstanding the

world and your position in it and then

hopefully

hopefully uh you get to the place in

your in in your in your world where

you're you develop a bit more and you

have some self-reflection and you can

call yourself out on the [ __ ] that

that you that you thought but also like

that's who you were at the time and

that's that's that um last thing I

wanted to ask you about was this staying

off versus staying up you said imagine

all all the things you felt you were

falling behind on if you didn't learn

about them last year would it really

have mattered if you started today

instead watch out for the Trap of must

know now what's that mean right now this

is like in the AI World we're in right

now every once in a while like in my for

you uh feed and Twitter it's like 10

things you got to know or you're falling

behind it's like this this's just like

this everyone's falling behind meanwhile

this thing is brand new and moving

faster than any human can can pay

attention

like I just keep seeing these stories

about like if you don't know this and

they're doing that and if you're not on

top of this it's like no probably

doesn't matter that much um and all the

things that if you would have read that

feed a year ago that you were supposed

to know uh it wouldn't have mattered

that much if you didn't um most things

uh some things would be handy to know

but like it probably wouldn't have

matter that much if you started now

instead or waited a year in some cases

one of the things I was doing for a

while I'm not doing anymore but I should

go back to doing it again this was

actually easier to do during the

pandemic was to go back and so so today

is is is May 22nd 2024 is to go back and

all the podcasts I listen to and listen

to May 22nd

2023 so listen to podcasts that are a

year old and during the pandemic it was

great because you hear all these experts

talking about this and talking about

that and everyone's so certain of

everything and you go back and listen

you're like man we are so wrong about so

many things and so many of the things we

were worried about never happened anyway

in this political issue and that

political issue and if this guy gets in

office this is going to happen if they

get in office this is going to happen

turns out very very few things actually

happen and it's really a nice exercise

to go back and listen to Old podcasts

and old interviews of substance and

realize that like there's some stuff

that was right some stuff that was wrong

but man the the sense of urgency in

these podcasts is is so misplaced

because most things don't need to happen

right now you don't need to be up on

this right now and you shouldn't feel

bad about not being on The Cutting Edge

of X Y or Z especially an edge that is

recutting itself and resharpening itself

every few months so that's what I'm

saying I I try to stay a bit out of

things I don't want to be on the edge of

things i' like let things settle in a

little bit more before I really start to

dig in do you read any biographies a few

I've read a few um I I really love the

idea biographies I have a hard time

reading long books yeah um and most

biographies tend to be very long I've

got like a limit where it's like 500

pages or less um uh yes but I I'll do

long but I'll do a long one every once

in a while but and I read a fair bit not

because I'm in a competition it's just

an hour a night is typically a book a

week and um I read a lot of biographies

I I like business biographies I love

history so like a lot of the World War

II leaders uh a lot of the American like

Titans of Industry um a lot of just

random people I I love biographies and I

have this process of what I do I've got

this um spreadsheet where if I I only

read on Kindle and anytime I see

something interesting I highlight it and

at the end of the book I'll like insert

I'll create a timeline uh here's where

they were born here's where they uh died

and then anything that I highlighted

that happened in this year that happened

in this year and then what I do is I go

to this website called newspapers.com

newspapers.com has archived pretty much

every newspaper ever back back until

like the

1600s and what I like to do is let's say

um I read this biography about uh Ted

Turner Ted Turner is the guy who started

CNN he was a fascinating guy to me or

let's actually biggest land owner in the

United States bigest yeah and he's done

a lot of fascinating things and the

reason why I use newspapers.com is I

like to go back to my Kindle and my

spreadsheet and I see all right in this

year he decided that he wanted to buy

land you know I'm going to go read a

newspaper article that wrote about about

him during that period And I want to see

what he said about his interests why

he's doing it and like did he say it

like for example uh maybe he'll say like

one day I hope to own like 5,000 Acres

turns out he owns millions and millions

and millions of acres and so I like to

read what the predictions were as well

as what the people were saying about the

person at the time so you don't get

revisionist history and what you notice

when you do this is there's often times

that you'll read uh a biography and

you'll think this was obvious that this

person was going to do this or they're

OB who wouldn't have predicted that this

was going to happen and or here's

another example uh World War II Church

Hill was like basically he was like the

the world's going to end like we are G

to Die the world's over uh we felt that

way during covid but if you read a lot

of history there's been many times where

we have felt this exact same feeling and

we had this exact same prediction you

know I remember I I recently read JFK's

book and like with the Missile Crisis it

was like the world's over and I go to

newspaper.com and I'll go and read what

the predictions are and what you notice

is

that people are wrong more than they're

right is it and so what you're saying

about things moving too fast I I I I

read uh Henry Ford's biography about

cars um or Henry Ford's biography and I

so I got interested in cars and I went

and read like what people were saying in

1912 when the Model T was coming out and

like the predictions are just ridiculous

and it's so funny that you don't to to

reiterate on your point you don't

actually have to be that fast to pounce

on certain things uh it's really quite

fascinating and to put this in

perspective the Ford came out with the

Model T I think in 1912 or 1916 so the

internet right now is something like 30

years old uh so that is basically like

how old would you say the internet is or

like the modern day internet the the the

commercial internet yeah like 95 96 is

when like you know really Mozilla or

Netscape kind of came out really kind of

made it happen it's basically basically

it's older than that cuz it's a research

thing but yeah commercially yeah 35

years let's say it's basically like a

car company in

1940 uh do you know what I mean yeah

yeah yeah and so what's really

fascinating is to like read all these

biographies and use newspaper.com it's

one of my favorite things to use and to

see what are interesting uh predictions

and how have they come true because I

already know the answer but I want to

know what were they saying at the time

and so that's my version of what you do

with 2023 is podcasts love that that's I

didn't know that site existed too that

that's fascinating it there's um a a an

ex account I follow called like

pessimists archive or something like

that I love that one it's a it's a great

one to follow and just you know like and

the thing is the thing that's a little

bit interesting about right now the time

we're in is that um there's so many

people saying so many things all wearing

the expert uniform some people are

experts like there are experts in this

world but many people act and play as

one based B on just their ability to

communicate on platforms and uh there's

just so much um certainty uh layered

into their suggestions and requirements

and requests and demands that it's just

it's very healthy to go every time you

see that every time there's like a you

must I I always back up and go probably

not like the more forward they are about

being certain and right about something

sort of the less interested I am in the

short term and I'd rather just sort of

stand back and see how it plays out and

at the end of the day um uh you know

there's there's plenty of opportunity in

a lot of different areas you don't need

to just pounce on everything as it's

happening um and in many cases it's it's

best to wait a little bit and see how

things settle out I mean I just think

about like with AI like all the

companies that began to implement AI

stuff early on uh and and then open AI

just like wiped them out in a lot of

ways for a lot of different reasons and

when you build on other people's

platforms you're very very much um at

risk of things changing tectonic plates

shifting very quickly you might have

been better off waiting and seeing how

things shake out so anyway who knows I

wanted you to come on here and just talk

because I've read your work for years

I've been a fan of yours for years I've

seen you do a bunch of interviews and I

just wanted someone told me uh this guy

named Dylan just said you should just

ask people what's interesting to them

and that's what I wanted to do uh with

you because you're an interesting person

and I respect your opinion on so many

things and so I appreciate you just

coming on and just riffing with me and

just telling me what what's intriguing

to you and it's been a lot of it's been

very valuable for me just to see how you

think and what what grabs your attention

well thanks for the invitation it was it

was really fun and and as I mentioned

earlier I just I want to make useful

things and hopefully this is a useful

conversation for for us and for anyone

listening so thanks thanks for inviting

me and it was a real pleasure all right

that's the pod

[Music]