Let me tell you about a company I fell in love with.
Not in a weird way. In the way where you start reading one article, then another, then you’re three years deep into quarterly reports, founder interviews, and YouTube rabbit holes at 11pm on a Tuesday because you simply cannot stop learning about what this company is doing. It started as curiosity. It became something close to obsession. And when the opportunity to invest in them came along before they went public, I jumped in like a golden retriever spotting a lake.
A couple of years later, a second opportunity came up. I invested again. And because I genuinely believed in this company, I told a friend about it. I laid out everything I knew. The vision, the leadership, the trajectory, the reasons I thought this was going somewhere real.
My friend listened politely, nodded thoughtfully, and said no thanks.
I was baffled. How could they not see what I saw?
Here’s what I’ve since figured out: they couldn’t see what I saw because they hadn’t watched what I watched, read what I read, or spent years quietly becoming fascinated by this company the way I had. I had years of accumulated knowledge. They had a single conversation with me. From their perspective, passing was the smart move. You don’t bet serious money on something a friend told you about over lunch, no matter how enthusiastic that friend is.
They made the right call. They just didn’t know it yet.
Fast forward a bit.
The company has done well. Really well. And when my friend and I caught up recently, they asked how the investment was going. I told them it was going great. There was a pause. The kind of pause that carries the full weight of “I wish I had done that.”
I get it. That feeling is deeply human. But I want to push back on it, because I think regret over a missed investment opportunity is one of the least productive emotions a person can spend time on. And here’s why.
You’re not actually comparing equivalent choices.
When my friend looks back now, they’re comparing their decision then to the outcome they can see today. That’s not a fair comparison. The decision they made was based on the information available to them at the time, which was incomplete, unfamiliar, and filtered through exactly one source: me, over lunch, probably gesturing enthusiastically with a fork.
The outcome they’re comparing it to is hindsight. Perfect, beautiful, useless hindsight.
This is the cognitive trick that makes missed investments feel so painful. You’re holding your past self to a standard that only exists because time has already passed. Your past self didn’t have the future. Your past self made a reasonable choice with the data they had. That’s actually what good decision-making looks like.
Let’s talk about some famous examples, since we love those.
Apple went public in December 1980 at $22 per share. As of this writing, adjusted for splits, that’s essentially pocket change that would be worth an almost comical amount of money today.
Were you in a position to invest in Apple in 1980? I was eight years old. My financial strategy at the time centered on convincing my parents I needed more allowance. Even the adults who could have invested in Apple didn’t know they were watching the beginning of the most valuable company in the history of the world. They saw a computer company. A lot of people thought it was cute.
Nobody beats themselves up for not buying Apple in 1980 because enough time has passed that we all understand we couldn’t have known. But give it a decade and people will mourn missing Nvidia’s rise with the same theatrical grief.
Here’s another one: Bitcoin.
I first heard about Bitcoin during the Greek financial crisis. It was trading around $300, and my reaction was somewhere between “that’s interesting” and “that’s absolutely ridiculous.” Turns out I wasn’t entirely wrong, and I also wasn’t entirely right. Bitcoin’s price has gone up by an amount that would require a very long number to express. People who bought Bitcoin at $300 are now either extremely rich or extremely nervous about regulatory news, sometimes simultaneously.
Do I regret not buying Bitcoin at $300? Not at all. Because I didn’t understand it. I thought it was speculative nonsense with a cool name. That was my honest assessment. Investing in something you think is speculative nonsense on the off chance you’re wrong isn’t a strategy. It’s gambling with extra steps. And for the record, I still think Bitcoin is fascinating in a “watching someone juggle chainsaws” kind of way. I admire the audacity. I’m going to keep watching from here. Also, I still don’t understand it. (And no, this isn’t me asking for someone to explain it to me. I’m fine sitting in my ignorance.)
The math of missed opportunities is actually pretty forgiving.
We live in a country with an absurd number of investing opportunities at any given moment. The stock market alone contains thousands of companies. There are real estate deals, index funds, small business investments, REITs, private equity opportunities, and approximately fourteen thousand ways to invest in something that produces more money than a savings account.
You’re never going to catch all the winners. Nobody does. Not Warren Buffett, not your brother-in-law who won’t stop talking about his portfolio, not the most sophisticated hedge fund managers on the planet. In fact, the entire premise of index fund investing, which is arguably the most proven and accessible wealth-building strategy available to regular humans, is that nobody can consistently pick the winners. So you buy all of them and let the market sort it out.
If you genuinely regret missing an investment, the most productive thing you can do is ask yourself: why didn’t I invest? If the answer is “I didn’t know enough about it,” that’s actionable. Build better habits around staying informed. Follow industries that interest you. Let curiosity compound over time the same way money does.
If the answer is “I knew about it but wasn’t comfortable investing,” that’s not a failure. That’s your gut doing its job. There’s no shame in passing on an investment that doesn’t sit right with you. The investing graveyard is full of confident people who ignored their instincts.
Here’s the thing about knowledge-driven investing.
The reason I felt comfortable investing in that company wasn’t luck. It was familiarity. I had followed this company for years before the opportunity existed. I understood what they were trying to do, why it mattered, and why I thought they had a real shot at doing it. That’s not a guarantee of anything, but it’s a foundation for a decision you can actually stand behind.
My friend didn’t have that. My friend had my enthusiasm, which I promise you can be a lot, and a 5-minute window to evaluate an investment I’d spent years thinking about. Saying no was not a failure of courage or foresight. It was a completely sane response to an asymmetric information situation.
When people say “I should have invested in X,” what they usually mean is “I wish I had known then what I know now.” But that’s not how time works, unfortunately. You can’t borrow knowledge from the future. You can only work with what you have in the present.
So work with what you have. Get curious about things. Follow industries that interest you. Read the articles. Watch the interviews. Let yourself get a little obsessed with something. Not because every obsession will turn into an investment opportunity, but because accumulated knowledge is the closest thing to a genuine edge that a regular person can develop.
And if you miss one?
You’ll be fine. There will be others. There are ALWAYS others.
The goal isn’t to be the person who invested in every good thing and avoided every bad thing. That person doesn’t exist. The goal is to build steady habits, make informed decisions, and let the power of consistent investing do its thing over time.
Your friend who regrets missing an opportunity isn’t bad at investing. They’re human. That’s a completely normal reaction to watching something you passed on succeed. But the right response isn’t regret. It’s curiosity. What would it take for me to feel confident the next time an opportunity like this comes along?
Start there.
The opportunities are coming. They always do.
Leave a Reply