InvestingWithBrandon

Retail investor: I trade credit spreads. Defined risk, I always know my max loss.
Me: & what's your max GAIN?
Retail investor: Capped too. That's the tradeoff.
Me: So on a company you're bullish on, you bought a leg that caps your own upside... to hedge a drop on something you wanted to own anyway?
Retail investor: ...I never framed it like that.
Me: You're paying to hedge against your own conviction. If you're bullish, BE bullish. I sell portfolio secured puts & buy long duration calls to magnify the best setups. No cap on the good stuff.
Retail investor: So stop paying to limit my own winner

Retail investor: I'm always in & out. Gotta stay active to make money in this market.
Me: How's all that activity working out?
Retail investor: I'm busy for sure. Returns are kind of meh though.
Me: Because activity isn't progress. There isn't deals every single day worth capitalizing on...
Retail investor: But doing nothing feels lazy...
Me: Doing nothing on great companies is the hardest & most profitable thing in investing. I make ONE good decision & let it compound for months/years.
Retail investor: So less trading, more holding?
Me: The best investors are barely doing anything. They own t

Retail investor: I buy cheap out of the money calls. Tiny risk, massive upside if they hit.
Me: How often do they actually hit?
Retail investor: Honestly? Almost never. But when one does, it's huge.
Me: So you're bleeding small losses over & over, praying one lotto ticket covers all of them?
Retail investor: ...when I add it all up I'm probably way down.
Me: That's the trap. "Small risk" 50 times in a row is a massive risk. When I'm ultra bullish I buy long duration calls on great companies & give the thesis real time to play out.
Retail investor: So fewer bets, but actually give them time and

Retail investor: I'm 52. Feels too late for me to start with this stuff.
Me: You planning to die at 60?
Retail investor: ...no. Hopefully 85, 90.
Me: So you've got 30+ years of compounding left & you're calling it "too late"?
Retail investor: I guess I always thought investing was a young person's game.
Me: The best time was 20 years ago. But money invested at 52 still likely doubles a few times before you need it. & selling portfolio secured puts pays you income NOW, not just decades out.
Retail investor: So I can build AND get income along the way?
Me: Exactly!
Don't talk yourself out of 30

Retail investor: I run poor man's covered calls. Buy a LEAP, sell weekly calls against it.
Me: So you're capping the upside on your own LEAP every single week?
Retail investor: But I'm collecting premium on it.
Me: So the company finally rips & your short call chokes the LEAP you actually wanted to ride. You strangled your best trade for a little weekly premium.
Retail investor: ...I have gotten burned on big green days.
Me: I buy long duration calls to MAGNIFY my most bullish setups. I don't sell calls against them & cap the upside. That defeats the whole point.
Retail investor: So just let t

Retail investor: I'm waiting for rates to drop before I get back in.
Me: & what if they don't?
Retail investor: Then... I guess I keep waiting?
Me: So your whole plan hinges on predicting the Fed, something the smartest people on Wall Street get wrong constantly?
Retail investor: When you say it like that it sounds dumb.
Me: It's not dumb, it's just a losing game. I don't predict rates, elections, or any of it. I buy great companies for less than they're worth & sell portfolio secured puts whenever the price is right.
Retail investor: So you never wait for the "perfect" moment?
Me: The perfect

Retail investor: I tried selling puts once. Got assigned, freaked out, & sold the shares at a loss. Never again.
Me: What'd you sell the put on?
Retail investor: Honestly some random stock with a fat premium.
Me: There's your problem. You sold a put on garbage you never actually wanted, then panic dumped it the second you got it.
Retail investor: ...so the assignment wasn't really the problem?
Me: The COMPANY was the problem. I only sell puts on elite companies I'd be thrilled to own. If I get assigned, I just got a great business on sale & I happily hold it for years.
Retail investor: So assi

Retail investor: I keep most of my money in a high yield savings. 4% & it's totally safe.
Me: Safe from what?
Retail investor: From the market crashing. I sleep fine.
Me: Inflation runs 3%+. So your "4% safe" is really about 1% after it eats your buying power... while the market did 10%+ without you.
Retail investor: But at least I can't lose it.
Me: You're losing it slowly. Just quiet enough that you don't feel it. That's the most dangerous kind of loss.
Retail investor: ...I never looked at it that way.
Me: Keep your emergency fund in cash, sure. The rest? Buy great companies & sell portfoli

Retail investor: I trade off the news. Buy when headlines are good, sell when they turn bad.
Me: So you're acting on info AFTER millions of people already read it?
Retail investor: I mean... it just came out though.
Me: By the time a headline hits your phone, the price already moved. You're buying the top of the excitement & selling the bottom of the fear.
Retail investor: ...that's exactly what keeps happening to me.
Me: News is noise. I don't care what a stock does this week. I buy great companies for less than they're worth & only do options to magnify ultra compelling setups.
Retail invest

Retail investor: I always take profits when I'm up 20-30%. Lock in the gains.
Me: On your best companies too?
Retail investor: Especially those. Don't want to get greedy.
Me: So you sell your WINNERS... the elite companies actually carrying your portfolio?
Retail investor: I mean, a gain isn't real till you sell, right?
Me: & then it triples after you're out, you pay taxes on the sale, & you're sitting in cash wondering what to buy next.
Retail investor: ...I've literally done that.
Me: I never sell my winners just to sell them... I often hold them for years & sell portfolio secured puts to pu

The first $100k is the hardest money you'll ever make.
Not because of the math...
Because of YOU.
$10k in the bank? "Let's book the Caribbean."
$50k? "Time for a new car."
That stuff is easy to buy and produces NOTHING.
Once you can stare at $99k and NOT blow it, you've already won the hardest battle.
After my first 100k, every 100k after that came easy.
Stop trying to make $100k.
Aim for your first million.
You'll think completely differently about how to get there.

HOW TO INVEST $100,000 RIGHT NOW IN JUNE 2026:
(works on any amount though)
$40k $VOO
$40k $Q
$20k individual companies
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.
- I keep ratios in check so if I ever get assigned, my base por

There is a HUGE problem with your covered calls right now...
I bet many are ITM and you are rolling up and out like you follow the herd to do...
The problem with the CC roll is that you are rolling in the direction of the EPS growth.
Why does that matter?
Because EPS growth is very strong right now & where EPS goes is where the stock price usually goes...
So getting your CCs to expire worthless is tough now.
Upside is capped.
Downside was never actually protected.
Bullish to buy the shares/
Bearish to sell calls against them and cap upside.
You are betting against yourself in a way...
So now w

THE STOCK MARKET WILL MAKE YOU WANT TO DO THE WRONG THING AT THE WORST TIME.
(this crushes most people)
When stocks are expensive and ripping, you feel like buying everything. (usually more risky)
When stocks are cheap and everyone is scared, you feel like selling everything. (usually a better deal)
When a great stock goes sideways, you feel like replacing it. (a big upside move could be close)
When your plan is finally about to work, you mess it up...
The market is not just testing your research/thesis.
It is testing your patience, discipline, & emotions.
Most people do not lose because they

Here's a secret the wealthy will never say out loud:
They don't sell their best shares. Ever.
I plan to hold my core $VOO & $Q until I die.
My kids inherit them at a stepped up cost basis... meaning all those gains? Taxed at basically zero.
Meanwhile I'm selling puts against those same shares for cash flow the whole time.
Income now. Appreciation forever. Taxes drastically reduced.
Selling portfolio secured puts let you generate the income WITHOUT ever touching the golden goose.

Retail investor: I buy puts to protect my portfolio in case of a crash.
Me: How often does that protection actually pay off?
Retail investor: Almost never honestly. But I sleep better.
Me: So you're paying a bill every month for insurance you almost never use, and it drags your returns the entire time?
Retail investor: …I never really did the math on it.
Me: I don't buy puts. I SELL them. I'm the one collecting that fear money instead of paying it out.
Retail investor: But what protects YOU in a crash?
Me: I only own great companies I bought for less than they're worth, I'm never over leverage

Retail investor: I'm gonna learn to day trade. That's where the real money is.
Me: How's it going so far?
Retail investor: Up some days, down others. I'll get there though.
Me: 94% of day traders lose money long term. You really think you're in the 6%?
Retail investor: I mean… somebody has to be.
Me: Sure. Somebody wins the lottery too. I stopped trying to be the exception. I simply buy great companies for less than they are worth and use long duration options to magnify ultra bullish setups.
Retail investor: So you're not glued to charts all day?
Me: I check things maybe 10 minutes a day. T
h

People hear "options" and think gambling.
Then they go buy weekly calls and lose their whole account.
So yeah, fair.
But that's not what I do.
I sell 1+ year portfolio secured puts on the best companies on earth when they're cheap.
I get paid up front.
And the worst case is I own a great company at a discount.
Same word. Completely different game.
One version is a slot machine.
One is a way to actually beat the market in the long run.