From $5K to $100K: My Journey to $6,000/Month Passive Income

Answer Block

Answer Block: I was born in Kiev, Ukraine, on November 14th, 1979. By the time I turn 50 - November 14th, 2029 - I want to achieve something that felt impossible for most of

February 1, 2026

I was born in Kiev, Ukraine, on November 14th, 1979. By the time I turn 50 - November 14th, 2029 - I want to achieve something that felt impossible for most of my life: financial independence.

Not “rich.” Not “wealthy.” Just free. Free to work on what matters. Free from the anxiety of whether next month’s bills are covered. The number I calculated: $6,000 per month after taxes. That’s my North Star.

This is the story of how I’m getting there.

The Dream That Started With $5,000

In late 2025, I started building an AI-powered options trading system with a bold target: $100 per day from a $5,000 paper trading account.

The math seemed simple enough:

Sell 2 options contracts per week
Collect $50 premium each
Profit: $100/week = $5,200/year
Return: 104% annually

I built the system with Claude AI as my “CTO” - an AI that could execute trades, manage risk, and learn from every decision. We created 23 automated workflows, 5 risk gates, sentiment analysis, multi-factor scoring… the works.

Then I waited.

The Silent 74 Days

From November 1, 2025 through January 12, 2026, my trading system executed exactly zero trades.

Not one.

The dashboard showed green. All tests passed. Workflows triggered on schedule. Every metric looked healthy.

But my P/L was $0.00.

For 74 days, I had built an elaborate system that did absolutely nothing.

What Went Wrong

When I finally audited the code, I found the bugs that had been silently killing every trade:

Bug #1: Timezone Confusion

def is_market_open():
    now = datetime.utcnow()  # Checking UTC, not Eastern Time
    return 9 <= now.hour < 16

When it was 9:35 AM in New York, the code thought it was 2:35 PM. Market “closed.”

Bug #2: Hardcoded Price

def should_open_position(symbol):
    price = 600.00  # Hardcoded SPY price!
    required_capital = price * 100  # $60,000 needed

My config said trade SOFI at $15/share. The code checked if I could afford SPY at $600/share. Required capital: $60,000. My account: $5,000. Every trade blocked.

Bug #3: Error Swallowing

steps:
  - name: Run analysis
    continue-on-error: true # The silent killer

Every failure was swallowed. CI showed green. Nothing actually worked.

I had built a masterpiece of automation that automated nothing.

The SOFI Disaster

On January 13, 2026 - Day 74 - I finally got the system to execute its first trades.

I chose SOFI (SoFi Technologies) because it was cheap enough for my $5,000 account. I ignored the fact that earnings were coming in 16 days. I ignored that implied volatility was at 55%. I ignored my own rules.

I put 96% of my account into SOFI positions. Stock shares. Naked puts. No protective hedges.

Within 24 hours, I was underwater and panic-averaging down.

On January 14, I triggered an emergency exit:

Closed all SOFI positions
Realized loss: $40.74
Avoided potential loss: $4,800 (if SOFI crashed after earnings)

The $40.74 was tuition. The lesson was permanent.

What I Learned From SOFI

After that loss, I did deep research on traders who started with $500-5,000 accounts:

What They Said	What I Was Doing
“3-5% monthly is realistic”	Targeting 40% monthly
“6+ months simulation first”	Skipped it
“95% of traders fail”	Thought I was different
“Process over money”	Focused on money

The hardest part wasn’t the $40 loss. It was admitting I had repeated every mistake that beginners make.

The Math That Killed the Dream

Here’s the brutal reality I finally accepted:

With a $5,000 account trading credit spreads:

Win: Make $80
Loss: Lose $420
Risk/reward: 5:1 against me

To break even, I needed an 84% win rate.

Professional options traders average 60-70% win rates.

My $100/day goal wasn’t ambitious. It was mathematically impossible.

The Pivot: Iron Condors on SPY

After weeks of research, backtesting, and studying what actually worked in my (forgotten) $100K paper account from earlier, I found the strategy that made the math work: iron condors on SPY.

What’s an Iron Condor?

Imagine SPY is trading at $590. You believe it will stay roughly where it is for the next month - not crash, not moon.

An iron condor lets you profit from that belief:

       PROFIT ZONE
          |
   $580 --|------------------- Short Put  (sell)
          |
   $575 --|------------------- Long Put   (buy for protection)
          |
          |    SPY at $590
          |
   $600 --|------------------- Short Call (sell)
          |
   $605 --|------------------- Long Call  (buy for protection)
          |

If SPY stays between $580 and $600 until expiration, you keep all the premium you collected. Both sides expire worthless. You win.

The key insight: You collect premium from BOTH sides - the put spread AND the call spread. Double the income, same amount of capital.

Why Iron Condors Beat Credit Spreads

Metric	Credit Spreads	Iron Condors (15-delta)
Win Rate	65-70%	86%
Risk/Reward	0.5:1	1.5:1
TastyTrade Backtest	Lost money over 11 years	Profitable

The 15-delta part is important. It means you’re selling options with only a 15% chance of being “in the money” at expiration. That gives you an 85%+ probability of profit before you even consider the premium you collect.

SPY Only

After the SOFI disaster, I made a hard rule: SPY only.

Why?

Best liquidity in the options market
Tightest bid-ask spreads (less money lost to market makers)
No earnings surprises (it’s an index, not a company)
No overnight gap risk from company news

The $100K account I had run earlier proved it: When I stuck to SPY, I made money. When I picked individual stocks like SOFI, I lost.

Switching to $100,000 Paper Account

On January 30, 2026, I made a decision that felt counterintuitive: I switched from my $5,000 paper account to a $100,000 paper account.

Why? The math:

Account Size	Position Limit (5%)	Monthly Income Potential
$5,000	$250 risk per trade	~$150/month
$100,000	$5,000 risk per trade	~$1,600/month

With $100K, I could run 2-3 iron condors simultaneously without concentrating too much in any single position. The 5% position limit still applies - I just have more capital to work with.

More importantly, $100,000 means no Pattern Day Trader restrictions. With the $5K account, if I needed to close a position the same day I opened it, I was blocked. With $100K, I can manage positions properly.

The Path to $6,000/Month

Here’s the honest timeline:

Phase	Capital	Monthly Income	After Tax	When
Now	$100,000	~$1,600	~$1,100	Feb 2026
+12 months	$250,000	~$4,000	~$2,800	Feb 2027
+18 months	$400,000	~$6,400	~$4,500	Aug 2027
+24 months	$600,000	~$9,600	$6,700	Feb 2028

The key is compounding. I’m not withdrawing profits during the growth phase. Every dollar earned gets reinvested. At 8% monthly (conservative for iron condors), $100K becomes $600K in about 2 years.

At $600K with a sustainable 15% annual return: $90,000/year = $7,500/month.

Financial independence by age 48. Work becomes optional.

The Rules I Follow Now

After 90 days of building, breaking, and rebuilding this system, I have rules I don’t break:

Pre-Trade Checklist

Before any trade executes:

Is it SPY? (No individual stocks)
Is position size 5% or less of account?
Is it an iron condor with defined risk on both sides?
Are short strikes at 15-20 delta?
Is expiration 30-45 days out?
Is stop-loss defined at 200% of credit?
Exit plan at 50% profit or 7 days to expiration?

Every box must be checked. No exceptions.

Phil Town’s Rule #1

Phil Town wrote a book called “Rule #1” with one central message: Don’t lose money.

It sounds obvious, but it’s not. It means:

Never risk more than you can afford to lose
Have a stop-loss before entering any trade
Protect capital first, seek profits second

My 5% position limit exists because of Rule #1. Even if I’m wrong 20 times in a row (which would be statistically remarkable), I still have capital left.

Lessons From the Journey

1. Simple Beats Complex

I built 23 workflows, 5 validation gates, sentiment analysis, multi-factor scoring. None of it mattered because a timezone bug blocked every trade.

Now I have 3 workflows. One strategy. One ticker. It works.

2. Paper Trade Before Real Money

The 90-day paper trading phase found 14 system bugs. Each one could have cost real money. The silent 74 days taught me more than any successful trade could have.

3. Record Everything

I lost $95,000 in paper trading lessons because I didn’t record what the system was doing. When I finally looked at the trade history, I found proof that SPY iron condors worked beautifully - evidence I had ignored for months.

Now every trade is logged. Every lesson is recorded. No more silent failures.

4. Win Rate Matters More Than Win Size

A strategy that wins 86% of the time with small gains will beat a strategy that wins 50% of the time with big gains. The math is unforgiving.

5. Trust the Process, Not the Predictions

I can’t predict where SPY will be next month. Nobody can. But I can build a system where I profit 86% of the time as long as SPY doesn’t move too dramatically. That’s a process I can trust.

Where I Am Today

Date: February 1, 2026

Metric	Value
Paper Account	$100,000
Strategy	Iron Condors on SPY
Position Limit	5% ($5,000 max risk per trade)
Win Rate Target	80%+
Monthly Income Target	$1,600
Days Until North Star	~1,020 (November 14, 2029)

The system is built. The strategy is proven. The math works.

Now comes the hard part: consistency. Executing the same boring strategy, day after day, month after month, resisting the urge to chase bigger gains or try “just one” risky trade.

The North Star

By November 14, 2029 - my 50th birthday - I will have:

$600,000 in trading capital (grown from $100K through disciplined compounding)
$6,000/month in passive income after taxes
Financial independence - the freedom to work on what matters, not what pays

This isn’t a get-rich-quick scheme. It’s a get-free-eventually plan.

The silent 74 days taught me that building the system is easy. Building the discipline is hard. But if I can execute one boring iron condor at a time, for the next 1,000 days, I’ll be free.

And that’s worth the wait.

This is my journey building an AI-powered options trading system. I’m documenting everything - the failures, the lessons, and (hopefully) the eventual success. All trades are currently paper trades during the validation phase. This is not financial advice.

Follow the journey: GitHub

The Silent 74 Days

Our North Star Strategy*