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When Investing Stops Feeling Like Building [Raw Session]

June 17, 2026

When you are investing with a little, it can feel like hope. You put a bit of money into something, you learn, you watch it move, and it feels like you are building. Even if it drops, the loss hurts, but it does not feel like it can change your life. But when the numbers get bigger, the same investment can feel completely different. $2,000 in a risky stock can feel like possibility. $20,000 in that same stock can feel like pressure. Same company. Same percentage move. Completely different mindset. In this raw session, I’m thinking through the difference between investing when you are trying to build something and investing when you already have something to protect. That connects to athletes losing money after retirement, lottery winners, inheritance, quiet wealth, lifestyle creep, and the strange stress that can come with having enough. This is not financial advice. It is more of a personal reflection on money, risk, fear, discipline, and trying to keep the lessons from having less while building something more stable. Chapters: 00:00 When investing feels like building 01:32 The penthouse and basement idea 02:59 Investing with little 04:08 The lessons from having less 05:05 When bigger numbers feel different 05:58 Why having more can make decisions harder 07:27 Athletes, lottery winners, and inheritance 09:10 Quiet wealth and living below your means 10:45 My own version of this 12:26 Spending on what actually matters 13:29 Quality over quantity 16:01 How this ties back to investing 16:55 The middle path 18:26 Final reflection 19:47 More money, heavier decisions

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Transcript

When Investing Stops Feeling Like Building [Raw Session]

00:00 — When Investing Feels Like Building vs Protecting

Hey, welcome back to So Builds. I’ve been thinking about the idea lately. When you have a little,

investing feels like building. When you have a lot, investing sometimes feels like

protecting. I guess the best way to do it is, I was thinking, let’s just say there’s a stock

and you think about putting in it. Let’s just take SpaceX for example to start with. So if you put,

say right now like if you had very little and so $2,000 you put 2k in that feels like

Hope you have hope that 2,000 will turn into something great now

Let’s say you have a fair amount of money. So you want to put in like you’re looking at

$20,000 well that

20,000 more or less feels like a risk

there’s a little bit of your worryness of is that money gonna grow or am I gonna lose it and

I think that explains a lot about money stress because we usually assume that having more money makes investing easier and

In some ways that obviously does because you have the money to put in

If you have more money you have more options you have more margin you can absorb mistakes better

You can get access to things other people can’t but emotionally I don’t think it’s it’s that simple because once you have something to lose

The whole feeling changes. It’s not just about getting ahead anymore. It becomes more about not falling backwards

01:32 — The Penthouse and Basement Idea

You know, I got this from I was watching Bloomberg this morning and a rod was on and he was talking about

from the penthouse to the basement and

And that really hit me like thinking about it. And that’s what made this whole video come about

So he’s talking about like as a superstar and athlete. He basically lived in the penthouse

his big paycheck, he was treated like a superstar, but then when he retired and he had to move

into the business world, he’s not starting from the lobby or the third floor.

He said like I’m starting from the basement.

I don’t have any contacts.

I don’t have any room.

I got to learn from the beginning.

I’m starting from nothing really because that is really what money can feel like.

If you start with very little, you are trying to climb.

If you’re trying to get from the basement to maybe the main floor, then maybe one day

to somewhere better.

But if you already have a lot, or if you have built a lot, the fear changes.

You’re not only looking up, you’re looking down.

You’re thinking, “What if I mess this up?

What if I lose what I’ve built?”

You trust around people, you make the wrong choices, you take the wrong risk, and you

end up back where you started.

completely different emotional game in my mind. Climbing is stressful but trying

not to fall is more or just as stressful in a different way.

02:59 — Investing With Little

So when you’re

investing with little, investing can feel more hopeful. Not easy, it’s not

painless, but there’s always that hope, that glimmer of someday hopefully I’ll

make it. You put a small amount of money, maybe 25, 50, 100, maybe you buy one ETF

Maybe you buy a few shares.

Maybe you’re just starting to learn about investing.

And every little bit feels like proof that you’re moving.

You’re building something that was not there before.

You’re not managing a fortune.

You’re not building, but you are building the habit.

You’re trying to learn the languages.

You’re learning how to take the risks and how to manage the risks.

You’re learning what it feels like when the market goes up and down.

You’re building confidence, one small decision at a time.

in the dividends, when a dividend comes in, it’s like a yay, like I made the right choice.

The stock goes down, you’re feeling down on yourself, but then all of a sudden, ch-ching,

it’s like, oh, well, that’s a little bit of a win.

So when you’re starting with little, the first win is not the return.

The first one is becoming someone who invests.

And that’s a great way to look at it, I believe.

04:08 — The Useful Lessons From Having Less

But then the useful lessons from having less, coming from less can teach some useful things.

always healthy things but useful. You learn to watch prices, you learn to wait for sales,

and you learn to ask if something is worth it. You learn that money represents work.

You learn that a dollar is not just a dollar, it’s time, effort, it’s stress. It’s a choice

you had to make. So when you invest, you pay attention to it. You do your research. You’re

You may not assume the person in the nice suit knows more than you do.

You may be forced to develop your own filters.

And so having less can make you careful because carelessness is very expensive

and you don’t want to go through that.

You, you work hard for your money and you want to be careful for where you,

where you put your money to work for you.

05:05 — Investing With More

Um, but when you have more, the numbers change.

And even if the percentages are the same, the motion weight is not the same.

losing 10% of a thousand’s a hundred.

That hurts, but it’s very survivable.

Losing 10% on a million, that’s a hundred grand.

The same percentage, but it hits a little different.

And that is where investing is stopped feeling

like building and starts feeling like you’re protecting,

you’re protecting the numbers,

you’re protecting the lifestyle, the future,

you’re protecting your family.

The version of yourself that feels like

you finally made progress and you don’t wanna lose that.

That can make people more careful.

very risk adverse, but can also make people more anxious.

And anxiety does not always create better decision.

The math may be percentage based,

but the fear is dollar based.

05:58 — Why Having More Can Make You Worse

And why having more makes you worse.

That’s a weird title to have.

This is the part people do not always talk about.

Having more money can make you better equipped,

but it can also make you worse if you’re not careful.

because now there are more doors open.

More people want to pitch you,

more people want to devise you.

There’s more private deals that show up all of a sudden.

More business ideas sound possible.

More people around you seem successful.

And when everyone around you is talking in bigger numbers,

bigger risks, those risks and the advice they’re giving you

and everything, it kind of starts to feel normal

and that’s dangerous because the size of the opportunity

distract you from the quality of the decision.

Bigger money can create bigger mistakes.

It creates more access,

more access does not mean better judgment.

More confidence can turn into overconfidence pretty quickly.

You think everything you do is a winner.

You everything you touch turns to gold.

But really, you need to be very careful about those decisions

and continue to do the research and the due diligence

that you were doing when you had nothing.

More advice can become more noise

and more opportunity become more temptation.

And that’s a big problem.

You’re tempted to be part of everything,

but you need to be selective.

Having more options is only useful

if you still know how to say no.

07:27 — Athletes, Lottery Winners, and Inheritance

And this brings up a couple of different things

about like athletes and lottery winners and inheritance.

So, and this is why those old stories

about athletes going broke after retirement hit differently.

I’m careful.

I’m careful with the exact stats about this because some of the numbers people

repeat are probably not clean, they’re not true, but the pattern makes sense to

me. Someone makes a lot of money in a short window, the lifestyle grows, friends

and family depend on them, advisors show up, business opportunities start coming

out of the woodwork, and put them the career ends. It could be an injury, it could be a

trade, it could be any number of reasons, so the income stops, but that lifestyle

stop. You’ve built up this lifestyle and dependency and that’s not just a spending

problem that’s an identity problem. Same with lottery winners. The money arrives

before the skill. The money arrives before the habits were built and the

money arrives before you’ve had spending boundaries because now you have an

abundance of money that you didn’t have before. You used to live within your

limits or as close as who knows maybe you were living outside of them and that

lottery win is just a it’s going to continue those bad habits someone who

was used to thinking and hundreds or thousands of something expect to make

decisions and millions and that is not normal same with inheritance you can

inherit the money without inheriting the discipline that’s built with it you can

receive receive the result without receiving the scar tissue that goes along

with building that wealth. Money without habits is very, it’s fragile.

09:10 — The Opposite Problem: Quiet Wealth

And the opposite problem,

quiet wealth. But there’s another side to it too. Like some people do the opposite. They save

everything. They spend almost nothing. They build wealth quietly. They never look wealthy.

They never act wealthy. And sometimes that is impressive. But sometimes it raises another

question. Do they control the money or did the fear control them? I had a friend growing up whose

family look like they were just getting by. Mother worked in the cafeteria, father was

the school bus driver, old cars, same old house, a very small house, hand-me-downs,

and nothing crazy. Just normal life from the outside. And I say that because we all lived

like that back then. And we all went to the same school and we all had like, I’m not going

to say it was a mix between blue collar and white collar, like low white collar.

We grew up not hand-to-mouth, but we grew up within our means.

But then later, like in my friend’s situation, her parents passed.

And all of a sudden, people realized her parents had serious money.

She was instantly a millionaire because it was all left to her, an only child.

And that made me think because from the outside we thought they had less, but really they

were living far below what they could afford.

And maybe that was wise, maybe some of it was fair, maybe both were true, maybe they

were just going off what they were taught and just putting the money away.

And there’s a difference between not having money and not spending money.

10:45 — My Own Version of This

And my own version of this, this is the way I feel.

I think about this in my own life because in a lot of ways I still like, I live like

And my wife especially lives like that. We look for sales

My wife will return something and rebuy it just to save a couple dollars

She does not like paying full price unless the values there. Well, we will pay for value where it’s deserved

We have older vehicles that have been paid off for years

15 16 years old vehicles repairs are annoying, but they usually still cheaper than having monthly payments

we have a small lease car that we

Really hate the car, but it gets the job done. It’s cheap. It’s reliable and

It’s within warranty so anything goes wrong the kids drive it everyone’s happy

It’s from A to B and that’s it and we don’t like the car and we hate the car, but it’s cheap

Our house is not fancy

Compared to new houses probably feel small outdated not modern

We do have an in-ground pool, but like a defense that goes around my yard

It looks like it’s falling down from the outside the gate the gate

I don’t even know how we got past inspection with the gate for the pool the deck

It’s a bit slanted and some of the boards need to be replaced and when you took an aerial picture of our backyard

It needs to be painted pretty bad

and honestly the

Deck probably needs to be replaced

But it’s still standing and it still works and we’re not trying to win some imaginary lifestyle competition

12:26 — Spending on What Actually Matters

But we do spend at the same time. We do spend money. We spend money on trips. We spend money on memories

We spend on things we actually care about we put we put that in ground pool and because my wife loves to swim

I love to swim I do my laps in the mornings

My love my wife loves going out between her calls at work and she’ll be altered till 7 doing her swim dance

She loves being in the pool

So for us that that matters to her that adds something real to our lives we explore we travel

We build moments with the family, so it’s not about never spending. It’s about knowing why we are spending

We could do both we could take the trips have the pool upgrade the house buy newer vehicles and still probably be fine

But just because we can afford something does not mean it’s worth buying it just because money is available

does not mean it needs to be used.

We could spend more and still be fine,

but being fine is not the same as being wise.

Some of these things AI puts in, I love.

13:29 — Quality Over Quantity

And quality over quantity.

I think this is where, for us,

it’s not just with the stuff, it’s with life also.

More things does not automatically mean a better life.

More expensive does not automatically mean better.

Newer does not, I mean, meaningful.

A bigger house might be nice.

A newer car would definitely be nice.

A clean deck, a deck that we’re not afraid

is gonna fall over, it would be awesome.

But every upgrade has a cost.

Like we have appliances we need to replace.

We’ve had a microwave that, it’s a built-in microwave

and it’s been broken for years.

So we use it as like another cupboard.

Our stove, the main big burner has been broken for five, six years.

So we’ve learned to deal with three burners.

Our fridge doesn’t make ice anymore and now it’s leaking.

But they’re going to give out pretty soon.

But they work.

So we’re fine with that.

And we’ll live with it.

And I’m not saying we have to.

It’s more or less we can’t find what we want.

We’re not just going to replace it with just something to replace it.

As long as we can get by, we’ll get by until we find what we want.

And we’re willing to pay for what we want, but we’re not willing to settle.

We’re not willing to just put whatever in there.

So the things we buy, we care for.

We take care of them.

We don’t break them.

We don’t throw them out.

We reuse them.

We donate them.

We try to sell them.

And we try to keep them as long as possible.

If something breaks, even if it’s out of warranty, we will make the phone call to see if we can

get some compensation. It’s happened right now with one of the things in the pool.

They’re gonna send me a new motor for free to let me try. So it’s not about

it’s not about like I said it’s it’s it’s it’s quality over quantity and like

every upgrade has a cost so we’re careful with what we do upgrade. It’s not

just the price the cost is also more pressure maintenance expectations money

leaving every month, the mental load of having to make the payment. So the question becomes,

does this actually improve our life or does it just make the outside look better? And

that’s where money can either serve you or start managing you. I do not want, I do not

want we can’t afford it to become the reason for every decision.

16:01 — How This Ties Back to Investing

And how this ties back

to investment. And this is all, it’s all about investing really, because investing is not

only about picking the right stock or ETF or business to put your money in, it’s about

what kind of person you become around money. If you are careless when you have little,

more money will probably make you more careless. If you are fearful when you have little, more

money may not fix the fair. It’s definitely not going to fix the fair. If you spend for

image more money gives you more image to buy. If you save from panic more money

gives you more to protect. So the real work is not just building portfolio the

real work is building the judgment to handle the portfolio. The hardest part

about having more money might be keeping the lessons from having less.

16:55 — The Middle Path

And that’s

true. The middle path is probably what I’m trying to figure out. I don’t want to

live from fair. I don’t want to hoard every dollar. I don’t want to save so much

that life passes by but I also don’t want to drift into lifestyle creep. I

don’t want to spend because other people would. I don’t want to invest in things I

don’t understand just because someone with confidence says it’s a good deal or

a great idea or it’s not gonna blow up. I want the money to create options. I want

fewer payments, less pressure, more freedom. I want more ability to take care

I want more ability to make memories. I want a more ability to help where it actually makes sense and

That is different from trying to look rich. I don’t want to be house poor. I

Do not think I want money so I can look wealthy. I want money so life has more room

I love the people a lot of people like when I show up there’s a all I look he looks homeless

I drive an old Jeep that looks like it’s beat up.

My pants have, I wear shoes that are falling apart

and my pants have holes in them.

I don’t look like, I don’t walk around like,

I don’t try to look like I’m rich and I’m fine with that.

I don’t want that stigma.

And I don’t have any reason for anyone

to try to impress anyone.

I have the people in my family around me

and we all know each other and my friends know who I am

and that’s what matters most to me.

18:26 — Final Reflection

So from the final reflection here,

so when I hear that line about the penthouse

and the basement,

I think the goal is not just escape the basement.

It is to not forget about the basement,

what the basement taught you,

because coming from less can teach you value.

It can teach you patience.

It can teach you to be cautious.

It can teach you how to stretch money.

But you also have to be careful

not to carry the fear forever.

And if you ever do build something

inherent something or receive a windfall or reach a point where you have enough

the question changes. Is it no longer just can I build? It becomes can I protect

without panicking? Can I spend without showing off? Can I invest without

gambling? Can I save without hoarding? Can I use money without letting money

become the whole of my whole identity? That is the part I’m still trying to

think through. Maybe having little makes investing feel like hope and having more

feel like responsibility. I think it makes it feel like risk. The other one is

easy. They are just different but I think the danger is assuming that more money

more money automatically means less stress. It does not. Sometimes more money

just gives you a different kind of stress. A quieter one. A much heavier one

to be honest.

19:47 — More Money, Heavier Decisions

And not that I have a lot of money. No, I’m still worrying about like can I

ever retire. I’m hoping for that day sometime. I’m hoping some of my stocks and some of my

picks and some of my investments are going to pay off someday. And even then I think

I still want to work. I don’t want to stop what I do. I enjoy what I do and I love it.

And I want to build and create and that’s a beautiful thing in my mind. So I don’t,

Even if we had money tomorrow, I don’t think I would stop what I’m doing.

I might take a little less more time off because I don’t take much time off at all.

But anyway, back to it.

More money does make your decisions in your life a little more heavier sometimes because

now you are not only trying to build a life, you’re trying not to lose the life.

And maybe the real goal is to keep the useful parts on both sides, keep the hunger from

having keep that hunger from having less keep the caution keep the respect for

money that’s the big one you got to respect money but also learn to enjoy

the parts of life that money is supposed to support when you have little

investing feels like building when you have a lot investing feels like

protecting and maybe the work is learning how to do both without letting

fair or ego make the decision.

I hope you like this one.

Thanks for sticking around.

Bye.