After two decades in tech, my biggest regret isn't a career move — it's how I managed my money

After two decades in the tech industry, my biggest regret isn't a job I turned down or a startup I didn't join. It's that I didn't manage my money well.

And no — I don't mean I should have been better at predicting the market or timing it. I mean something much simpler: I should have stayed invested in high-quality compounders. That alone would have compounded my wealth.

When I look back at my financial journey, only two investments truly paid off: my Amazon RSUs, which grew 4x from 2016 to 2020, and a small business I acquired, which returned 7x in 7 years. Compare that to the Qualcomm ESOPs I held for more than a decade and sold at a 75% total return — exactly what the S&P 500 delivered over the same period. Hindsight is 20/20, and looking back it's obvious: staying invested in high-quality compounders is the way to go. But to actually do it, you need a structured process to (1) identify quality compounders correctly and (2) keep track of them without it consuming your life.

Before I get to what I built, let me set the context: who I'm talking about, the environment they operate in, what they believe, and how they actually make investment decisions.

The smartest people I know are terrible investors

Most of my friends are high-net-worth professionals at the tech giants. They are, by any measure, very smart people. Yet none of them has a formal background in finance or investing, and nearly all of them struggle to invest their wealth well. The standard prescription for passive investing is the index fund — and it works, right up until a multi-year downturn. When a portfolio has been red for a long time, almost nobody has the patience to hold on. Many book the loss instead of riding through it. And in case it isn't obvious yet: I was one of them.

Conventional wisdom didn't serve me any better. Take real estate — the investment everyone calls "safe." I bought my first house in 2006 and sold it in 2012 for roughly the same price. Not a good return once you factor in inflation (though still better than renting, since my interest payments were lower than rent would have been). The 2008 meltdown showed just how risky "safe" can be: many people lost their primary homes — not because they made a mistake, but because lenders got greedy and lent to just about anyone. Then in 2022, I lost a $100K investment as a limited partner in a commercial real estate deal. The general partners bought the property at peak prices, and it went underwater within 18 months. I'm not saying all real estate investments are bad. I'm saying not all of them are as good and safe as conventional wisdom suggests.

FOMO is not a strategy

Here's the irony about smart tech professionals: they spend less time researching the fundamentals of a company they're about to invest in than they spend hunting for Thanksgiving deals. If I had to sum up their strategy in one word, it would be FOMO. It's FOMO that drove them into the SpaceX IPO. To their credit, they know it's risky — so they hedge by keeping the position small. But that same instinct means they never go big when a truly high-quality company momentarily becomes available at an attractive valuation, driven down by market fears that have nothing to do with its long-term prospects.

Look at Microsoft on March 27, 2026. It dropped to $356 in what turned out to be the stock's worst quarter since 2008. Most of us busy professionals were, well, busy — responding to emails, with no time to research and act that day. Less than five months later, the stock was trading back above $480. I'm not claiming to have a magic formula for calling the bottom; nobody knows the bottom. But imagine getting an email that evening saying what caused the drop — and another one, days later, saying the specific fear that made it cheap had just eased, with the source attached, while the price hadn't moved yet. That day convinced me I needed a time-efficient way to keep tabs on high-quality compounders, recognize when a valuation becomes attractive, take a position, and stay invested for at least five years.

The real cost is time

I keep saying "time-efficient," because the real cost here isn't money — it's time. Learning to identify a quality compounder, and then tracking the metrics that actually matter, is no small task. An engineer naturally understands engineering companies, so their investing universe shrinks to tech — and they miss the moment when a company like Visa goes on sale. So what do they do instead? They make speculative bets on finding "the next NVIDIA" before the market does — usually on a tip from a friend at a party. I'm sure you can relate. Remember the friend who told you how much he made on Bitcoin in the early days, and how much he regrets not buying more? The reason most of us never go big on those bets is that deep down, we know exactly what we're doing: placing a speculative what-if wager with hard-earned money. So we keep it small.

The week that changed how I invest

When it came time for my first business acquisition, I did none of the things I used to do when buying stocks. I didn't take advice from a friend at a party. I wasn't chasing a 1,000% return. Instead, I spent a focused week on financial due diligence and then moved fast to close the deal before anyone else could get in. Here's the part that matters: by the time I made that acquisition in 2018, I had been researching potential acquisitions for over seven years. Those years of pattern recognition, combined with seven days of thorough diligence, gave me the confidence to go big — and that investment compounded 7x in 7 years.

That got me thinking: isn't it just common sense to repeat this process when buying publicly traded companies? Identify a pool of high-quality compounders — businesses like the one I bought. Watch for when one of them enters a buy zone (not a bottom — a buy zone). Then do enough due diligence to confirm the discount isn't a broken business before making the buy decision. The only reasons smart people don't do this: (1) we don't have the know-how to identify these companies, and (2) we're too busy with our day jobs to react during the few days a company sits in a buy zone.

The genesis of OffhoursInvesting.com

That is why I built offhoursinvesting.com — a web-based research tool I originally developed for myself, one that maintains a quality universe and helps me run value and risk analysis on the handful of companies I understand well.

The process is simple — four features, one flow. The tool gives you the Quality Universe: a filtered list of companies with a decade-plus of proven growth, whose returns on invested capital beat what a safe Treasury investment would have earned. Every day it flags the Buy Zone — the shorter list trading at attractive valuations against their own five-year history — along with a plain-language read on why each one is cheap. See a name you care about? One click puts it on your Watch List, and from then on the story comes to you. Any day it moves more than 3%, you get an email that evening with the cause attached. The fears that make it cheap — named by its research report — are tracked against the news, including news that isn't about the company at all, and you hear the day one of those fears gets better or worse, with a dated source. The day before a scheduled event your report told you to watch — earnings, a ruling — you get a reminder with exactly what to check. And every Monday morning, one email retells your Watch List's week. When you're ready to go deeper, generate a fresh nine-section due diligence report in about five minutes (I recommend setting aside two hours to read it), or browse the archive — every report ever run is readable by every subscriber.

The bottom line: days of due diligence, compressed into two hours of reading. You don't need to know which metrics matter for which type of business — the tool does. It pulls high-quality data from financial data providers such as FMP and Yahoo Finance, combines it with qualitative research (earnings reports, web search, insider buying, and more), and presents it all in an easy-to-follow format.

Conviction is built, not bought

One more thing: never invest in a company without watching it through some real news first. Yes, that means you may miss a stock that's in the Buy Zone right now. That's fine — there will always be stocks in the Buy Zone. Watching costs you almost nothing: a five-minute Monday email, an alert only when something actually happens, and a growing dossier on each stock — every big move explained, every fear tracked with receipts. When the price finally dips and the emails say the fears are easing rather than materializing, you're not deciding in a panic; the conviction is already built. And when your inbox gets busy about one stock, that frequency itself is the signal to pay attention.

To be clear: this is an educational tool that helps you make informed decisions. It is not a financial advisor, and you should not use it as one. It does the hours of research you don't have time for — but the buy decision is always yours. You may have noticed I haven't said a word about selling. That's intentional. My philosophy is to take a position in a high-quality compounder — like my small business — at the right time, and then stay invested forever, or at least five-plus years.

See for yourself

Remember the Microsoft story above? I've made the complete Microsoft analysis — along with one on Nvidia (yes, the same Nvidia from the party-tip story — given the full sober treatment) — available as sample reports at offhoursinvesting.com. Read them free; just leave your email, and you'll join The Backbenchers' Brief, the weekly newsletter. These two are the permanent samples — every other analysis in the growing library is part of the paid product. Read one, and judge for yourself whether two hours of reading can replace days of research. If it clicks, early subscribers lock in the Founders' Rate.

Your investing philosophy may differ from mine, and I fully respect that this tool may not be as useful to you as it is to me. Either way, I wish you the very best in compounding your wealth with minimal risk.

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Editorial analysis, not investment advice. Past performance doesn't predict future results.