Investing Philosophy
How I actually think about money, what I've learned the hard way, and why boring is the whole point. This isn't financial advice. This is me trying to be honest about a topic most people fake expertise on.
No tickers, no specific numbers, no "trust me bro" recommendations. Just frameworks and hard-won lessons.
How It Started
My first real investment wasn't stocks. It was a condo. I was in my mid-twenties, the numbers were absurd (17% cash-on-cash returns at the time), and it taught me something I still believe: when the math works, move. Don't wait for perfect conditions, don't overthink it, just run the numbers, understand the downside, and go.
For years, I was all-in on real estate. I read The Millionaire Real Estate Investor cover to cover, listened to probably 300 episodes of the BiggerPockets podcast, and genuinely believed the majority of my long-term wealth would come from slowly and consistently acquiring rental properties over decades. Buy, hold, cash flow, repeat. That was the plan.
Around 2020, I shifted away from that strategy. The market had changed, the numbers stopped working the way they used to, and I pivoted to the general stock market. Not because stocks are better in some absolute sense, but because the math told me to go where the math was working. I'm still open to real estate if the right opportunity shows up, but I'm not forcing it anymore.
And then I started picking stocks, where I promptly learned a very different lesson: I am not good at this. More on that later.
The Real Estate Plot Twist
Before 2020, real estate in a growing market like Wilmington was a no-brainer. You could find properties where the cash-on-cash returns were exceptional, appreciation was steady, and the math just worked. I built a small portfolio on that thesis and it served me well.
That equation has completely changed. When I run the same numbers today, rental properties are often a loss before taxes. They've essentially become inflation hedges rather than wealth builders. Even if the market only returned 4% annually for the next decade, you'd still be better off in a low-cost S&P 500 or global index fund than buying a rental property at today's prices. That's wild. I never thought the real estate market would shift this dramatically, this quickly.
This is why I keep coming back to the boring answer: index funds. Not because real estate is bad, but because the math changes, and you have to be honest about when a strategy that used to work doesn't anymore.
Where I Actually Learned This Stuff
I didn't learn about personal finance from a degree or a financial advisor. I learned from YouTube, books, and making expensive mistakes. The single biggest influence on how I think about money is The Money Guy Show, hosted by Brian Preston and Bo Hanson. They're financial advisors who give away their entire framework for free, and it's better than anything I've gotten from anyone I've actually paid.
Warren Buffett's philosophy runs underneath all of it: invest in what you understand, think long-term, and don't try to be clever. His famous bet that a boring S&P 500 index fund would beat hedge fund managers over a decade (it did, by a lot) is the kind of thing that rewires how you think about this stuff.
Between the Money Guy framework and Buffett's "be boring on purpose" approach, I've landed on a philosophy that's simple: follow a clear order of operations, automate everything, remove emotion from the equation, and let compound interest do the work while I go live my life.
The Financial Order of Operations
The Money Guy Show's Financial Order of Operations (they call it the FOO) is a 9-step system for what to do with your next dollar. It's not sexy. It's not complicated. That's the point. The whole idea is that personal finance has an actual sequence, just like math, and doing things out of order costs you money.
Step 1: Cover Your Deductibles
Before you invest a single dollar, make sure you can cover your insurance deductibles. This is your financial floor. If you can't survive a car accident or a burst pipe without going into debt, nothing else matters.
Step 2: Get the Employer Match
If your employer matches 401(k) contributions, contribute enough to get the full match. It's free money. Literally a 100% return on day one. Skipping this is like leaving cash on the table and walking away.
Step 3: Kill High-Interest Debt
Credit cards, personal loans, anything with a high rate. This debt is actively working against you. Every dollar you throw at it earns you a guaranteed return equal to that interest rate.
Step 4: Build Emergency Reserves
3 to 6 months of expenses in a savings account. Not invested. Not "accessible." Actually sitting there, boring and liquid, so that when life happens you don't have to sell investments at the worst possible time.
Steps 5-6: Max Out Tax-Free Growth
Roth IRA, HSA, then max your other retirement accounts. Tax-free growth is the closest thing to a financial cheat code. The earlier you do this, the more powerful it gets.
Step 7: Hyper-Accumulation
The Money Guy target: save 25% of your gross income. This is where wealth actually gets built. Automate it. Make it boring. The goal is to get to a point where your "army of dollar bills" is working harder than you are.
Steps 8-9: Prepay Low-Interest Debt + Enjoy
Mortgage payoff and other low-rate debt. Only after everything above is handled. Then: enjoy your wealth. The whole point of building this machine is so you can actually live.
The key insight: Every dollar invested at age 30 has roughly a 23x wealth multiplier by retirement. At 20, it's 88x. At 40, it's around 7x. The math is ruthless about time, which is why the order matters so much. You don't want to be optimizing stock picks when you haven't even captured your employer match.
What I Actually Believe
The stock market captures innovation. That's the whole bet.
Here's the mental model that simplifies everything for me: the stock market is basically a bet on whether humans will keep innovating. AI bubble or not, it doesn't matter. Innovation gets captured in the market over time. Do I think there will be money made on innovation in the next 10, 20, 30 years? Yes. That's the whole thesis. A mix of U.S. and global index funds means I'm buying a piece of all of it without needing to pick which company wins.
Boring is the strategy, not the fallback
Index funds. Automatic contributions. Rebalancing once a year. That's it. The people who get rich slowly aren't the ones picking hot stocks. They're the ones who set up a system and then went to live their lives. I want a portfolio I can forget about for months at a time.
Automation removes the one thing that breaks it: me
Every behavioral finance study says the same thing: the biggest risk to your portfolio is your own emotions. Automating contributions, automating rebalancing, and never looking at my brokerage account during a downturn is how I protect myself from myself.
Time in the market beats timing the market
I know this is a cliché. I also know it's true. The money I've lost trying to "time" things dwarfs anything I've lost from just staying put. The wealth multiplier math is very clear: start early, stay consistent, don't touch it.
Understand the order before you optimize
Most personal finance content skips straight to "how to pick stocks" or "how to build passive income." That's like trying to paint the walls before you've poured the foundation. The FOO exists because sequence matters. Follow the steps in order and you'll end up ahead of most people who are chasing alpha.
My Actual Track Record
I write the stuff above because I believe it. But I also need a section on this page that keeps me honest, because knowing the right thing to do and actually doing it are two very different skills.
The truth is, I am an emotional investor. Specifically an emotional buyer. I tend to buy stocks when I want to feel like I'm taking control of something. And then I sell when I'm trying to simplify and optimize. Neither of those are good reasons to make financial decisions, and my track record reflects it. I am not good at trading. I should not be picking individual stocks. I know this. I still do it sometimes, and it almost always costs me money. This section is my reminder.
The Wall of Accountability
A running list of stock picks I've made with my own conviction. This section exists so I can look at it and remember that I should probably just buy the index. I plan to pull my full trade history from my tax records and put the complete carnage here eventually. For now, here are the highlights.
Made a "big bet" on a company competing with Topgolf right before COVID hit. Lost $6,000. The company got crushed during the pandemic, went private, and that money evaporated. Classic case of conviction without timing.
Bought in around $28 and $20 because I love The Witcher series and the hype was real. Then Cyberpunk 2077 had what might be the worst major game launch in history. Stock cratered to $4 or $5. Did I sell? No. I bought more on the way down because I was "sure" it would recover. I'm still holding, waiting for The Witcher 4 hype cycle to bail me out. This is what "emotional buyer" looks like in practice.
Bought about $4,000 worth of Disney at what turned out to be roughly the peak. Currently losing significant money on this trade. The thesis was fine (Disney+ growth, parks recovering), but the timing was pure emotion.
Full trade history from tax records is coming. There's more. It's not pretty. The pattern is always the same: I feel something, I buy something, the market doesn't care about my feelings.
The $70,000 Lesson
When I was 23 or 24, a Northwestern Mutual advisor convinced me to buy a whole life insurance policy as an "investment vehicle." The pitch was compelling: guaranteed growth, cash value, tax advantages. And I'll be honest: part of me knew it was probably wrong, even at the time. But they were really good salesmen, and I liked the idea of saving. It made me feel responsible. So I signed up.
Over the next decade, I paid into it and watched the cash value crawl. Multiple times I ran the numbers and thought about bailing. But every time I went back to the office, they'd walk me through the projections again and convince me to stay. It was a cocktail of sunk cost fallacy and ego. I didn't want to admit I'd made the wrong call. Nobody wants to look at a decade of premiums and say "yeah, that was all a mistake."
Here's what makes this sting: I didn't need whole life insurance. I was in my early twenties with no dependents. A term life policy would have cost a fraction of the price, and if I'd invested the difference in a basic index fund or even just REITs, that money would be worth roughly $70,000 more today thanks to compound growth. Instead, it sat inside a product designed to benefit the advisor who sold it to me.
I'll say what I think plainly: selling whole life insurance to a 23-year-old who doesn't even have a Roth IRA yet is, in my opinion, borderline predatory. There are very limited scenarios where whole life makes sense, and "young person with no dependents and no retirement accounts" is absolutely not one of them. The commission structure incentivizes advisors to put you in the most expensive product, not the right one. Young people get targeted because they don't know enough to push back.
This is why the Financial Order of Operations matters. If I'd had that framework at 23, I would have known exactly where that money should have gone: employer match first, then Roth, then index funds. Instead, I trusted a guy in a nice office and let ego keep me there for a decade. Expensive lesson. At least it only cost me $70K and not more.
Where I'm At Now
After years of learning, making mistakes, and slowly building the boring machine, here's the current state of the strategy. Not sharing specific numbers, but the framework is real and it's what I actually do.
What's Working
Maxing employer matches on both sides of our household. Maxing HSA contributions (and recently consolidated to a low-fee provider, because paying 1.7% in annual fees on an HSA is an insult). Backdoor Roth conversions every year. Automated contributions to low-cost index funds. The boring stuff is humming.
The Goal
Soft retirement somewhere around 45 to 50. Not "quit working forever" retirement. More like "never have to say yes to work that drains you" retirement. The goal is optionality: enough saved and invested that work becomes a choice, not an obligation. Design the life first, then let the numbers support it.
The Shift
I used to optimize aggressively. Chase the best returns, find the perfect deal, squeeze every percentage point. Now I optimize for simplicity. Fewer things to manage. Fewer accounts. Fewer decisions. The compounding benefits of a simple system that runs on autopilot beat the theoretical gains of a complex one that requires constant attention.
The Work In Progress
Understanding our actual spending. My wife and I have been running what we call "designed constraint" experiments: intentionally capping spending for a month to figure out which categories actually make us happy versus which ones are just convenience habits. You can't plan for retirement if you don't know what your life actually costs.
The Gambling Corner
OK, everything above is the "responsible adult" section. But I'm also a human being who thinks space is cool, and sometimes you want to throw a little money at something just because it's fun. So I keep a small, explicitly separate allocation for what I call "fun money." This is money I'm fully prepared to lose. It doesn't touch the boring portfolio. It doesn't break the FOO. It's just... gambling with extra steps.
The Space Bet
I have a small position in space-related companies. The thesis is simple: space infrastructure is going to be massive, and I want to own a tiny piece of the companies building it. I'm looking at you, Redwire. The real exit strategy? Hold until SpaceX eventually goes public and the entire sector gets repriced. This could go to zero or it could be a great story at a dinner party in 2035. Either way, it's a couple thousand dollars and I'm having fun.
The Rules
Fun money has boundaries. It's a fixed, small amount. It never comes from the main investment accounts. I don't add to positions when they're down (that's the emotional buyer talking). And I never, ever count it toward my actual retirement savings. This is entertainment spending that happens to show up in a brokerage account.
What Shaped My Thinking
The Millionaire Real Estate Investor
Gary Keller
Read this as a hard copy early on. The frameworks for evaluating rental properties were foundational for me. Worth noting: the specific numbers in this book are hilariously outdated now. The principles still hold, but the market it describes doesn't exist anymore.
The Holy Grail of Investing
Tony Robbins & Christopher Zook
Alternative investments explained for normal people. Changed how I think about what's possible beyond stocks and bonds.
Understanding Michael Porter
Joan Magretta
Not a finance book, but understanding competitive advantage is the single most useful lens for evaluating whether a business is actually worth owning.
~300 Episodes of BiggerPockets
BiggerPockets Real Estate Podcast
For years, this was my primary investing education. Long-term buy and hold, cash flow analysis, BRRRR strategy, market analysis. I genuinely believed the majority of my wealth would come from slowly and consistently acquiring rental properties over decades. Then 2020 happened and the math changed.
This page reflects my personal investing philosophy and is not financial advice. I'm not a financial advisor. Nothing here is a recommendation to buy, sell, or hold anything. The whole point of this page is that I'm still learning, and so should you. Do your own research.