InvestingWithBrandon

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You own $200k of index funds. You've never touched options before.
A great company drops 15% on a bad quarter. Business is fine, profits still growing, price just got hit.
You tell the market: I'll buy 100 shares at 10% below where it is now in a year.
$4,000 hits your account today in cash flow.
(this is selling a portfolio secured put)
Now.. three things can happen.
1. It recovers. You keep $4,000
2. It sits flat for a year. You keep $4,000
3. It drops to your strike price. You buy a company you wanted at a discount...
All of these outcomes are a win.
Wanna know the best part too?
Your index
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I'll make a bet with any covered call seller reading this.
Show me your last 5 years. Every premium you collected, added up.
Then show me every position that got called away & what those shares are worth today.
Then compare your total ROI vs the SP500
I'll bet most got smoked vs the brainless $VOO
Nobody does this math because the premiums show up on your statement every month & the called away upside shows up nowhere. Hard to beat the SP500 doing things like this as your primary strategy...
Run the numbers on your own account & tell me I'm wrong.
I hope I am wrong... but for most I am likely
Retail investor: I just buy and hold index funds. Slow and steady.
Me: Good. Seriously. That's the base. I do the exact same thing with $VOO and $Q
Retail investor: Wait, you hold index funds too?
Me: Of course. The only difference is I don't let them just sit there. I use them as collateral and sell puts against them for another 15% ish on top.
Retail investor: So you're not replacing index investing… you're stacking on it?
Me: Exactly. You're doing step one perfectly. You just stopped before step two.
Retail investor: What if he market crashes with he portfolio secured put?
Me: Ratios are al
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HOW TO BUILD A CASHFLOW MACHINE WITH $200,000 in 2026:
(works at almost any size)
$80k $VOO
$80k $Q
$40k high conviction companies
That base compounds ~11% a year & NEVER gets sold. Not in a crash, not ever.
Then sell puts secured by that base. Not cash.
Every sold put has to pass all 5:
1. Company is below fair value TODAY
2. Real moat & pricing power
3. Profits growing for years
4. Strike 10% below current price
5. 1 year duration minimum
Premium hits the same day & buys more $VOO + $Q + Elite companies.
Bigger base secures bigger puts. Bigger puts pay more premium. That loop is the entire s
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Find the "right time to buy" on this $Q chart
Down 29% in about 4 weeks. They closed the economy. Circuit breakers halting the whole market over & over.
Every day of that COVID drop, buying felt insane. Every headline said worse was coming.
Then it recovered in roughly 5 months & never looked back.
Here's what I want you to actually see. There was NO moment on this chart where it felt safe & cheap at the same time. At the bottom it felt like the end of the world. By the time it felt fine, the discount was gone.
That's every crash. The "good feeling" & the opportunity never show up together. Ev
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Walk into a bank with $100k.
Buy a CD, collect your 4%.
Then ask to ALSO use that same $100k as a down payment on a rental property...
They'll laugh you out the building.
"You can't have your money in two places at once."
But that's exactly what I do every single month.
My shares ( $VOO / $Q ) sit there compounding ~11% a year.
Those SAME shares secure the puts I sell for another ~15%.
Same money. Two returns. Never on margin. Ratios always in check.
That's how 10% quietly becomes 25%.
And 25% is the difference between $1M and $61M over time.
Portfolio secured puts will change your life.
This
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🔴Your crappy strike price is why you get smoked with options...
(how to fix it right now)
Most retail investors sell puts with a strike price 5% ish below the current market price to "build a margin of safety"
They usually do this with monthly contracts.
Here's the BIG problem.
5% is not a good enough margin of safety, especially with a 1 month contract where you have no tailwinds of growth behind you.
(as EPS climbs, the stock will follow that up)
The solution is to sell 1+ year puts.
You can pick a strike price 20% below the money, get great premium, build a MUCH better margin of safety, ha
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So many people think more trades = more money.
That couldn't be further from the truth.
Think about Warren Buffett at $BRK.
He's one of the most "boring" investors of all time yet he is viewed as the best investor of all time.
Why?
Because he buys great companies at good prices & simply waits.
Does nothing.
Let's the revenue grow.
Let's the EPS grow.
Doesn't panic over every single headline.
& over the course of years, the stock will flow the fundamentals.
This again is why I NEVER do short duration plays, especially with options.
You don't have the tailwind of growth behind you... Don't make
When the market "CRASHES"
Everyone says "Buy the dip"
But do you know what it feels like to actually buy during a "meltdown" as an average retail investor?
- Your portfolio is red.
- The news says the world is ending.
- You second guess everything.
- You end up panic selling... at the exact wrong time.
HAPPENS EVERY CYCLE TO MOST RETAIL INVESTORS.
Smart investors will:
- Buy shares while they are on sale.
- Buy calls when nobody wants them. (cheaper)
- Sell puts when the herd is paying top dollar for them. (selling for max premium)
I always say the emotional aspect of investing is what crushes
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Please... Just STOP.
Stop selling CSP's
Stop selling covered calls on bullish stocks
Stop day trading
Stop doing short duration options trades
Stop getting emotional with your investments
Stop following the broke herd
Instead, do this:
- Build base portfolio
- Sell portfolio secured puts
- Use cash flow to buy more shares & some LEAP calls.
- Know what you own and why
- Accept volatility as opportunity
- Do 1+ year duration plays because they are easier
- Keep ratios in check
- Be patient
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HOW TO INVEST $100,000 RIGHT NOW SEPTEMBER 17TH 2026:
(works on any amount though)
$40k $VOO
$40k $Q
$15k individual companies
$5k leap calls
THEN:
Sell 1 year puts portfolio secured, (not cash secured) on companies that meet this criteria:
1. Must be below intrinsic value.
2. Must have a moat.
3. Must have pricing power.
4. Must have a durable competitive advantage.
5. I must be ok to hold for the long run in the event I get assigned shares, I can use the wheel strategy and patiently "get rid" of the shares if I want.
KEY NOTES:
- Portfolio secured, not cash.
- Ratios in check to be just fine
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🟢Before I sell ANY put.
All 5 MUST be a YES. No exceptions.
1. Elite company... moat, pricing power, competitive advantage
2. Valuation must be good
3. Strike ~10% below that. Discount on top of discount
4. A year+ duration... so EPS has time to grow
5. Ratios in check... my base could cover all assignments even after a 50% crash
This checklist is boring. It's repetitive. It's also why I've never been wiped out in 12+ years & actually beat the market... while the "exciting" traders restart from ZERO every 18 months
What's the difference between RIGHT NOW & the 2000 Dot Com crash?
Then the PE ratio was 100
Now the PE ratio is 21
Yes... we will experience volatility.
Yes... Iran, oil, rates, bond yields, fed, Ai, inflation...
ALWAYS something to worry about.
but right now is very unlikely to be a bubble like it was in 2000.
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Retail investor: I got a raise & I'm not sure what to do with the extra money.
Me: What'd you do with the last one?
Retail investor: ...honestly? It just kind of disappeared into life.
Me: That's the most expensive thing that happens to most people & nobody notices it happening.
Retail investor: Lifestyle creep, I know.
Me: Here's the thing... You were fine on the old salary. So the entire raise is free money you've already proven you don't need.
Retail investor: So put all of it in?
Me: Look at that chart. Every raise you've ever had could've gone in there & you'd have never felt it missing.
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Retail investor: I jump out when things get scary, then hop back in once it's safe.
Me: You know the best days almost always come right after the worst ones?
Retail investor: ...they do?
Me: Miss just the 10 best days over a couple decades & your returns get cut nearly in HALF... & those days cluster right in the middle of the panic you're running from.
Time in the market > timing the market
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UNPOPULAR BRUTAL TRUTH...
We will ALWAYS have something "bad happening" & something to "worry about"
Iran, Oil, Hormuz, Inflation, Fed, Trump, ect...
But the "this time is different" saying has yet to be correct 1 single time...
Continue to buy great companies for less than they are worth and only do 1+ year options to magnify ultra high confidence setups.
& guess what... the future is likely to look like the past. VOLATILE.
STICK TO THE PLAN.
I don't day trade... 99% of them lose. (see chart below)
I don't sell covered calls... they cap the exact upside.
I don't sell cash secured puts... I'm not parking six figures in dead cash.
I don't touch weeklies... nobody knows what a stock does in 5 days.
I don't run spreads... I'm not paying to bet against my own trade.
I don't watch screens all day.
Here's what I actually do:
Build a base of $VOO + $Q
+ Elite companies that I hold for the long run.
Sell 1+ year portfolio secured puts on great companies below fair value, secured by that base.
Premium buys more shares. Shares secure bigger p
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The first 25k is the hardest
but... the first $100k is is a little easier than the first 25k
but... the first $1M is a little easier than the first 100k
but... the first $2M is a little easier than the first 1m
One you get to one level, the next comes faster.
STICK WITH IT.
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Retail investor: Nike $NKE just hit a 52 week low. That's gotta be a steal at these prices.
Me: Maybe. Let's actually check instead of guessing.
Retail investor: It's Nike. Everybody knows Nike.
Me: Brand recognition doesn't matter... Pull up the earnings. Are profits growing or shrinking over the last few years?
Retail investor: ...I don't actually know.
Me: That's the whole question. A falling price with growing profits is a dip. A falling price with falling profits is a company in trouble...
Retail investor: So a 52 week low means nothing by itself?
Me: Nothing. It's a price, not a value. W
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NKE-2.33%
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Retail investor: Oil just went over $100, inflation's at 3.4%, & now they're talking about RAISING rates. I'm going to cash.
Me: Look at that chart. Point to where all of that started.
Retail investor: ...it's been building for months.
Me: Yet somehow the Nasdaq $Q is up over 22% in the last year...
Retail investor: I know. That makes no sense.
Me: It never does in the moment. So many people focus on every little headline and miss the big needle mover stuff that ACTUALLY moves the market.
Retail investor: What is that? So I just ignore all this bad stuff?
Me: EPS growth is VERY strong. The eco
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