Your Portfolio Is Working. You're Not.

You've built something. Maybe it's a tech company generating seven figures. Maybe it's a consulting practice with recurring revenue. Maybe you've sold a business and you're sitting on capital that needs to work as hard as you did to earn it.

And now you're stuck in the same trap as every other successful entrepreneur who transitions into serious investing:

Your money is parked in index funds earning 8-10% annually while you watch Wall Street insiders generate monthly income that looks like a full-time salary.

You know there's a better way. You've heard about options trading. Maybe you've even dabbled—bought a few calls, watched them expire worthless, and sworn off "risky derivatives" forever.

Here's what nobody told you: You were playing the wrong side of the trade.

The Silent Wealth Transfer Happening Every Month

Every month, millions of retail investors buy options. They're betting on direction, timing, and magnitude—three variables that have to align perfectly for them to win.

The statistics are brutal: 90% of options buyers lose money.

But here's the part they don't advertise: for every options buyer losing money, there's an options seller collecting premium. Consistently. Predictably. Month after month.

Professional traders—the ones managing billions at proprietary trading firms—aren't buying options. They're selling them. Specifically, they're selling puts on high-quality companies, generating income while positioning themselves to own stocks they'd be happy to hold long-term.

And they're doing it with a success rate that's the inverse of retail traders: 70-80% win rates, not 10%.

The $15,000/Month Strategy That Flips the Script

Selling cash-secured puts is the most misunderstood wealth-building strategy in the market.

Here's how it works in plain English:

You identify a high-quality public company you'd be happy to own—let's say a stock trading at $150 that you believe is worth holding for decades. Instead of buying shares immediately, you sell a put option at a $145 strike price and collect a premium.

You've now been paid to wait.

If the stock stays above $145, you keep the entire premium (usually 1-3% of the capital you committed). Rinse and repeat next month. That's $1,500-$4,500 per $150,000 in buying power.

If the stock drops below $145, you're obligated to buy it—at a price you already decided was attractive—and you got paid to do it.

Either way, you win.

Scale this across multiple positions with $500,000 in capital, and suddenly you're generating $15,000+ monthly while building a portfolio of companies you actually want to own.

This isn't speculation. It's engineered income generation with a margin of safety.

The Position Wall Street Pros Never Take (And Why It Matters)

Here's the secret that separates amateurs from professionals:

Wall Street pros almost never sell naked puts at-the-money on stocks they don't want to own.

Read that again.

Retail traders get seduced by the highest premiums—the juiciest payouts—which almost always come from at-the-money or out-of-the-money puts on volatile, questionable companies.

They're chasing yield. Professionals are building positions.

The elite traders I've studied follow a different framework:

1. They only sell puts on stocks that meet their long-term quality criteria If they wouldn't buy and hold the underlying stock for 10+ years, they don't sell puts on it. Period. This filters out 95% of the "high premium" garbage that eventually blows up.

2. They sell puts 5-15% out-of-the-money, not at-the-money This creates a margin of safety. The stock can drop 10%, and they still don't get assigned. Meanwhile, they're collecting 0.5-1.5% monthly premium on capital—which annualizes to 6-18% on top of any underlying stock appreciation.

3. They treat assignment as a win, not a loss Getting assigned shares isn't a failure—it's the whole point. They just acquired a high-quality asset at a discount and got paid for the privilege.

This is the position amateurs never take: using options not to bet on price movement, but to systematically accumulate quality at advantageous prices while generating income.

It's not sexy. It's not exciting. But it's how you build an eight-figure portfolio while generating five-figure monthly income.

The Compounding Effect Nobody Talks About

Here's where it gets interesting.

Let's say you're generating $15,000/month in premium. Most people treat this like income and spend it. That's fine—it's real cash flow.

But what if you reinvested it?

$15,000/month is $180,000/year. Reinvested into the same strategy, you're now deploying $680,000 in year two (assuming you started with $500K). By year five, you're operating with $1.4M+ in capital—without adding a single dollar from outside sources.

The premiums compound. The shares you acquire through assignment compound. And if you've filtered for high-quality companies that appreciate over decades, the stock positions themselves compound.

This is how serious wealth is built: premium income + stock appreciation + reinvestment = exponential portfolio growth.

It's the same principle I use when investing in high-quality public companies that compound over decades. The difference is I'm getting paid monthly while I wait for the compounding to work.

What This Actually Looks Like in Practice

Let me show you a real example.

Target: High-quality tech stock trading at $200/share Capital allocated: $100,000

Strategy: Sell 5 put contracts at $190 strike, 30 days out

Premium collected: $750 per contract = $3,750 total

Scenario 1 (70% probability): Stock stays above $190

• You keep $3,750

• Repeat next month

• Annual return on committed capital: ~18-24% with zero stock ownership

Scenario 2 (30% probability): Stock drops to $185

• You're assigned 500 shares at $190 ($95,000)

• Your effective entry: $190 - $7.50 premium = $182.50/share

• Current price: $185

• You're essentially break-even with a 5% margin of safety built in

• Now you own a stock you wanted anyway, at a better price than today's $200

This is the game professionals play. They're not gambling on direction. They're systematically positioning themselves to win regardless of short-term price action.

The Three Mistakes That Destroy Put Sellers

Before you rush into this strategy, understand where amateurs blow up:

Mistake #1: Selling puts on garbage companies for higher premiums High volatility = high premium. It also = high risk of catastrophic loss. If you wouldn't hold the stock for 10 years, don't sell puts on it.

Mistake #2: Over-leveraging The math works beautifully until you're forced to take assignment on five positions simultaneously during a market crash and you don't have the cash. Professionals never commit more than 40-50% of their liquid capital to put-selling strategies.

Mistake #3: Panicking during assignment Assignment isn't failure—it's part of the strategy. If you've filtered for quality and selected appropriate strikes, getting assigned means you're acquiring great companies at good prices. This is the feature, not the bug.

Why This Strategy Fits Entrepreneurs and Investors

If you're reading this, you're probably not a day trader. You're a builder. You've created value through businesses, and now you're looking for asymmetric ways to deploy capital without staring at screens all day.

Selling puts is perfect for entrepreneurs because:

• It's systematic, not speculative - You're following a repeatable process, not gambling on hunches

• It generates monthly cash flow - Like recurring revenue, but from your portfolio

• It aligns with long-term wealth building - You're accumulating quality assets, not flipping trades

• It requires 30-60 minutes per month - Once positions are set, you're mostly hands-off

It's the closest thing to "recurring revenue from investing" that exists.

Watch the Full Breakdown

I've recorded a complete walkthrough of this strategy, including:

• The exact screening criteria I use to identify put-selling candidates

• How to calculate position sizing so you never over-leverage

• The strike selection formula that maximizes premium while minimizing risk

• Real portfolio examples showing monthly income generation

• How to handle assignment and turn it into portfolio advantage

• The tax implications and account setup considerations most people miss

Watch: $15K/Month Selling Puts - The Complete Strategy →

This isn't theory. This is the exact approach I've used to generate consistent monthly income while building a portfolio of high-quality companies that compound over decades.

Join The Sprint Club

If you're an entrepreneur or investor who's serious about systematic wealth building—without the chaos of day trading or the passivity of index funds—join The Sprint Club.

Inside, you'll find:

• Monthly portfolio reviews where we analyze real put-selling positions

• Access to screening tools and frameworks for identifying quality companies

• A community of entrepreneurs who've sold businesses and are now deploying capital intelligently

• Weekly breakdowns of market opportunities and position management tactics

This isn't for gamblers. It's for builders who want their capital working as strategically as they built their businesses.

Your move.

P.S. - The biggest objection I hear: "But what if I get assigned?" That's when I know someone doesn't understand the strategy. Getting assigned at prices you selected, on stocks you wanted, while having been paid to wait... that's not a problem. That's the entire point. Watch the video—you'll never look at options the same way again.