What Are YieldMax ETFs — And Are They Better Than Running the Wheel?
Hey everyone! It’s been a while since my last update, and a lot has been happening behind the scenes. I’ve been actively trading, keeping a close eye on the markets, and continuing to build out my very own trade tracking application. If you’ve been following along, you know HL Financial Strategies is centered around the Wheel Strategy — tracking trades, optimizing returns, and systematizing everything to make this approach repeatable and scalable.
That core focus hasn’t changed — but recently, a new player caught my attention: YieldMax ETFs. What exactly are these funds? Are they just pre-packaged versions of the Wheel? And if so… should I just buy one and call it a decade?
Let’s break it down.
💡 First Off — What Are YieldMax Funds?
If you’ve come across tickers like $MSTY, $TSLY, or $APLY, you’ve probably seen the crazy yields they advertise — often in the 25–50%+ annualized range! These are part of the YieldMax ETF family, a group of actively managed funds that aim to generate high monthly income using synthetic covered call strategies on popular stocks like MicroStrategy ($MSTR), Tesla ($TSLA), and Apple ($AAPL).
Sounds a lot like the Wheel Strategy, right?
Not quite.
Yes, YieldMax funds generate income through options — just like the Wheel. But the core difference is this:
YieldMax funds don’t preserve capital. The Wheel does.
These ETFs are built to maximize monthly yield, even if it means slowly eroding the fund’s value over time (called NAV erosion). Because they cap upside, don’t own the underlying stock, and constantly roll options, their long-term performance often trends down — even as they pay out those tempting monthly dividends.
🔁 Why I’m Using YieldMax (Carefully)
I’ve started building a small, tactical position in $MSTY — but with clear intent. This isn’t a long-term hold. I’m using it strictly as a short-term yield play, harvesting high monthly income and then funneling that income directly into long-term assets like $VOO and capital for my Wheel Strategy account.
Yes, to be clear: MSTY is not replacing the Wheel Strategy. Not even close!
Why? Because the Wheel lets you manage positions on stocks I choose and believe in. That’s the beauty of the Wheel:
You control the stocks, the strikes, the timing — and ultimately, your exposure.
With YieldMax funds, you give up that control. You don’t get to pick the underlying stock. You don’t get to decide how options are rolled. You’re buying a packaged strategy with no input — and with that, you also inherit the risks of NAV erosion and capped upside.
That’s not necessarily bad — but it’s very different from what the Wheel allows you to do.
So yes, I’ll continue to use MSTY as a supplemental income source, but the foundation of my strategy — and the reason I’ve been able to validate a path to financial independence — still rests on the control and compounding that the Wheel Strategy gives me.
📊 Running the Numbers: Validating Financial Independence
Lately, I’ve been running the numbers — and the path to financial independence is no longer just theoretical. After years of trading, saving, and investing, I’m finally at a point where stepping away from the W-2 grind isn’t just possible — it’s realistic. Not decades away and maybe not even years. But soon!
This isn’t traditional FIRE in the “retire early and live frugally” sense. But it’s something similar, even better imo:
Owning my time. Living on my terms. No longer needing a paycheck to survive.
Over the past few months, I’ve been modeling different paths:
Monthly income from the Wheel Strategy
Layering in my paycheck, company bonsues + stock options, some real estate cash flow, and HYSA reserves
Forecasting changes, healthcare and lifestyle expenses
I’ve done this over and over and am still in disbelief that it is still within reach. Here’s the bottom line:
Thanks to the foundation I’ve built around the Wheel, I’ve validated a real, sustainable path to early independence — one that generates income, preserves capital, and gives me complete flexibility.
It’s not about being rich. It’s about being free — and knowing that can do that on a system that lets me live life on my own terms.
🛠️ What Else I’ve Been Building
Aside from trading and planning for financial independence, I’ve been building something I’ve always wanted: a dedicated app to track my Wheel Strategy trades.
Sure, spreadsheets work — and if you’re trading, you absolutely should be tracking your positions — but I wanted more. Coming from a software engineering background, I knew I could build something better: a tool that tracks trades, calculates performance metrics, logs activity, and supports the full lifecycle of Wheel positions.
So in my spare time, I started building it. Introducing: The Wheel Trade Tracker App 🚀
It’s fully functional and currently includes:
A clean, validated trade entry flow
Separate tables for open vs. closed trades
Position lifecycle tracking (including partial and full closes)
Portfolio metrics to monitor capital usage and performance
It’s been a fun project to create from the ground up — and while it’s still a work in progress, I’ll definitely be using it for my own trades moving forward. If you’re interested in trying it out, I’d love to share it and hear your feedback.
🧭 Where This Is All Going
So that’s what I’ve been up to lately — researching YieldMax funds, modeling out early retirement, and developing the Wheel Tracker app from scratch.
But more than anything, I’ve been spending my time doing things I genuinely enjoy — on my terms, free from the pressure of a paycheck or the constraints of a corporate job.
This journey started as a way to trade more effectively. It’s become something bigger: a way to build a life around freedom, intention, and ownership of my time.
Thanks for following along!
-HL Financial Strategies