Henry

Why I Built WheelYield

Growing up in East Tennessee, I had lofty aspirations that lacked a stable foundation. But I had a few bedrock influences that shaped everything.

My father and I lived a five-minute bike ride from my grandparents' farm. My best friend lived on the other side of the road, about a mile away, and we'd meet halfway most summer mornings. We spent our days fishing, swimming, helping around the farm, or playing computer games — this was the early 2000s, and life was simple.

During those formative years, my grandfather taught me how competitive the world is and would become. He spent most days watching Bloomberg TV and Fox Business. His father had been president of a bank that was eventually acquired by Wachovia, which Wells Fargo later absorbed during the 2008 financial crisis. I spent hours sitting with him — listening, watching tickers scroll across the screen, and asking questions about markets and stocks that I barely understood at the time.

But I never brought myself to learn independently until years later.

Finding Direction Through Service

I struggled through middle school and high school — not with ability, but with engagement. The material didn't stimulate me, though I didn't understand that at the time. After graduation, I drifted through dead-end jobs and waited tables, trying to figure out who I was.

My aunt, a retired Army Colonel, pushed me to join the Air Force instead of pursuing a path as a deputy at the local Sheriff's Office. It was the best decision I never knew I needed.

I enlisted in the Air Force in 2012, and it was a natural fit. The military fostered my energy, competitive nature, and need for growth. More importantly, it gave me what I'd been missing — a sense of community and a team-first mindset. Just as I'd thrived in sports growing up, I began to thrive in uniform. I learned how to learn. The issue was never ability — I was bored with material that didn't challenge me. The Air Force fixed that.

During my active duty years, I also discovered a knack for finding deals. I started buying items at thrift stores, yard sales, and estate sales, then reselling them on eBay and Amazon. That side hustle built the nest egg I would later use to start trading.

I left active duty in 2016 and transitioned to the Air National Guard, where I now serve full-time as a Recruiting Flight Chief with the 118th Wing in Tennessee. I manage a recruiting team, conduct school and community outreach, and help the next generation of airmen find the same direction the Air Force gave me.

From $13 Bitcoin to Options

During my active duty time, I bought about two Bitcoin when it was roughly $13 a coin. I was a junior airman without much money, but I was confident in what I'd read about it. I ended up selling when it hit around $100 — a solid return at the time that I was proud of. In hindsight, those two coins would be worth over $200,000 today. That's a lesson I carry with me about conviction and patience.

That was my first real taste of markets, and I was hooked.

I started learning about options seriously in 2019, shortly before COVID hit. Like many traders during that period, I dove in headfirst. I discovered the wheel strategy early on but strayed from it — it felt “too slow” compared to the returns I was seeing from other traders online. So I dabbled in everything and became quite good at trading SPY 0-DTE options — zero days to expiration, the most aggressive form of options trading.

The Day Everything Changed

Shortly after my daughter Willow was born, I lost nearly 80% of my portfolio in a single day. Roughly $15,000–$16,000, gone between market open and close. One bad trade, one moment of overconfidence, and most of what I'd built was wiped out.

I went home that afternoon and spent the rest of the day on the floor playing with Willow, who was almost one at the time. No charts. No screens. No regret spiraling. Just her.

It was the most expensive lesson of my life, and the most important one.

The Comeback

After a week or two away from trading, I made a decision. I withdrew most of what I had left and committed to a disciplined approach: one SPY 0-DTE trade per day. I waited for the setup I believed in before pulling the trigger. Patient. Calculated. No revenge trading.

By the end of June, I had recovered 95% of what I'd lost.

But more importantly, I'd learned that I never wanted to be in that position again.

Why the Wheel

From that point forward, I went back to what I knew worked — the wheel strategy. I'd figured out early in life that consistency unlocks doors faster than home runs. The wheel gives you structure, income, and a repeatable framework for making decisions — exactly what I needed after nearly blowing up.

Since committing to the wheel strategy, I've grown my account from nearly $6,000 to $231,000 in approximately two and a half years. I've also paid close to $80,000 in taxes over the last two years, which is the kind of problem I'm happy to have.

I've taught several people in my life this method, and many of them have found success with it too. That's part of why I built this site — the wheel works, and more people deserve access to the tools and knowledge to do it right.

My Approach

The stock market is vast. There are countless ways to build wealth, and none of them are one-size-fits-all. But here's what works for me:

Understand options completely before selling one. Learn the Greeks. Understand time decay and IV crush. Know the terminology, and know when it's best to sell a call versus a put.

Don't get greedy. I avoid high-beta stocks — the ones that swing wildly in both directions. I focus on fundamentally strong companies that may be undervalued relative to their peers. My personal favorites recently have been Amazon and Qualcomm.

Ask yourself one question before every trade: Would I mind holding this stock long-term if I had to? If the answer is no, don't sell the put.

Have an exit plan. Know what your average-down strategy looks like. Know how you'll use it to exit a position earlier or start selling calls sooner. The wheel is a system — work the system.

Why Free

I'm the only one building and maintaining WheelYield. There's no team, no investors, no board. Just me, Claude Code, and a lot of late nights after my daughter goes to bed.

I made everything free because I know what it's like to want to learn but not have access to the right tools. When I was starting out, I couldn't afford premium platforms, and the free ones were either outdated or confusing. I wanted to build something that gives people a real edge — calculators, guides, stock analysis, a learning center — without asking for a credit card.

I think of WheelYield as a community, not a product. If these tools help even one person avoid the mistake I made or find the same consistency the wheel has given me, then every hour I've spent building this was worth it.

The People Behind Me

None of this would be possible without my wife. She keeps me grounded, supports the late-night coding sessions, and gives me the space to grow every single day. I couldn't learn, build, or push forward without her love and support.

And Willow — the reason I stopped, rethought everything, and came back better. She's the reason I trade differently now. She's the reason this site exists.

With my wife and Willow — shortly after she was born

Use These Tools Wisely

WheelYield gives you calculators, guides, stock analysis, and learning tools to make informed decisions. But please understand all the risks that come with investing and trading. Options involve substantial risk. Past performance — including mine — doesn't guarantee future results. Do your own research, understand your risk tolerance, and never trade with money you can't afford to lose.

— Henry