Henry's Toolkit
I'm not going to recommend 20 books I never read. Everything on this page is something I've actually read, watched, or used. If it's here, it helped me.
Some links on this page are affiliate links. If you purchase through them, WheelYield may earn a small commission at no additional cost to you. I only recommend products I've personally used or genuinely believe in. Full disclosure
Trading & Market Books
These shaped how I think about markets, risk, and decision-making.
Options as a Strategic Investment
Lawrence McMillan
“This is the bible. It’s dense and you won’t read it cover to cover, but it’s the reference book I keep coming back to when I need to understand a strategy at a deeper level. If you’re serious about options, own this book.”
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The Intelligent Investor
Benjamin Graham
“This book changed how I pick stocks for the wheel. Before reading it, I was chasing high IV tickers. After, I started asking ‘would I hold this for 10 years?’ That one shift made all the difference.”
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Trading in the Zone
Mark Douglas
“I read this after losing 80% of my portfolio in one day. If I’d read it before, I might not have been in that position. This book isn’t about strategies — it’s about the space between your ears. The section on thinking in probabilities rewired how I approach every trade.”
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A Random Walk Down Wall Street
Burton Malkiel
“A healthy dose of humility for anyone who thinks they can consistently beat the market. It made me appreciate why selling premium and collecting theta works — you’re not trying to predict direction, you’re selling overpriced insurance.”
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The Psychology of Money
Morgan Housel
“Short chapters, brilliant insights. The chapter about getting wealthy vs staying wealthy hit me hard. The wheel strategy is a ‘staying wealthy’ approach — slow, consistent, boring income that compounds. This book validated the path I was already on.”
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One Up on Wall Street
Peter Lynch
“Still working through this one, but Lynch’s idea of investing in what you know and understand is exactly how I pick wheel stocks. I trade Amazon because I understand the business. I trade Qualcomm because I understand the chip cycle. Buy what you know.”
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The Options Playbook
Brian Overby
“On my list. I’ve heard great things about the visual approach to explaining 40 strategies. If you’re more of a visual learner, this might be a better starting point than McMillan.”
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Thinking in Bets
Annie Duke
“On my list. A professional poker player’s approach to decision-making under uncertainty — which is exactly what options trading is. Multiple people I trust have recommended this one.”
View on AmazonMindset & Discipline
Trading is 80% mental. These books built the discipline I bring to every trade.
Can’t Hurt Me
David Goggins
“After losing $15K in one day, this book’s message hit different. The idea that suffering is a tool, not a punishment, is what got me to sit back down at the desk and trade my way back. Goggins doesn’t know anything about options, but he knows everything about not quitting.”
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Make Your Bed
Admiral William McRaven
“Small disciplines compound — in life and in trading. Start with the simple things. Stick to your rules. Don’t skip steps. This is a one-hour read that stays with you for years. As a military guy, this one resonated on a personal level.”
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Living with a SEAL
Jesse Itzler
“Hilarious and motivating. The lesson underneath the entertainment is about getting comfortable being uncomfortable — which is basically what selling options feels like when you’re new to it.”
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The Power of Broke
Daymond John
“I started trading with $6,000 and built WheelYield with no budget. This book explains why starting with nothing can actually be an advantage — it forces creativity, hustle, and resourcefulness. It’s the same energy that drove me to resell on eBay and Amazon during my active duty years.”
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Be Useful
Arnold Schwarzenegger
“Arnold’s approach to vision + relentless work ethic applies to everything. The chapter on seeing your goal clearly before you achieve it is exactly how I approached the $231K milestone — I could see it before I got there.”
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Alone at Dawn
Dan Schilling & Lori Chapman Longfritz
“The story of TSgt John Chapman, the first airman to receive the Medal of Honor since Vietnam. As an Air Force NCO, this one is personal. It’s about courage, sacrifice, and doing the right thing when nobody is watching. Not a trading book — a life book.”
View on AmazonYouTube Channels I Actually Watch
I learned more from these two channels than most paid courses.
In The Money — Adam
800K+ subscribers
“Adam is the best options educator on YouTube, period. His explanations are clear, visual, and practical. His covered call and CSP videos are what got me started with the wheel. If you watch one channel, make it this one.”
Best for: Options fundamentals, wheel strategy, Greeks explained visually
Watch on YouTubeBrad Finn
“Brad’s approach to selling options for income is straightforward and no-BS. He shows real trades with real numbers and doesn’t sugarcoat the losses. That honesty is rare on YouTube.”
Best for: Real trade examples, income strategy, wheel execution
Watch on YouTubeReading & Note-Taking Gear
The hardware I actually use to read, annotate, and journal trade ideas.
Kindle Scribe
11" display with AI notes
“If you’re going to read any of the books above, get a Scribe. I highlight passages, write margin notes on trading concepts, and journal trade ideas directly on the screen. It replaced a stack of notebooks for me. The AI tools summarize your handwritten notes — perfect for reviewing trade journal entries. No notifications, no social media, just reading and thinking.”
View on AmazonKindle Scribe Colorsoft
11" color display + AI notes
“Same Scribe but with a color display. Color-code your notes — green for winners, red for losers, gold for lessons learned. The color makes charts and book covers look great too. Worth the upgrade if you’re a visual note-taker.”
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Obviously biased, but I built these because nothing else was good enough.
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