You’ll Seldom Rue the Day You Underinvested
Why the smartest move in early-stage investing might be resisting the urge to go all in
This post is a follow-up to one of the very first pieces I wrote — Alternate Thoughts on Investing in Alternatives. That early piece was also about investing, but here I want to zoom in on one particular line from it: “You’ll seldom rue the day you underinvested.”
For the record — and so the lawyers and regulators can sleep at night — this is not financial advice. It’s written for entertainment and education. I’m not telling you how to invest your money. In fact, if you’re here for things outside of business and investing, you can probably skip this week’s words below and wait for next time.
This one is about business. The business of investing.
The Myth of the Once-in-a-Lifetime Opportunity
It happens to every investor sooner or later. You meet someone with a great idea. They’ve got the plan, the pitch, and maybe even a couple of impressive slides showing how this thing could be a billion-dollar business. You can see it in your head — the headlines, the acquisition, the payday. Your hand hovers over the “all in” button, thinking that the cash you’ve set aside for years could transform your life if this hits.
And yet, this is exactly the moment when the mind plays its cruelest trick. It zooms in on the potential upside and fades the messy parts into the background — the part about how the idea will actually be executed, how the founder will transform from clever dreamer into competent CEO of a billion-dollar operation, how the big checks other investors “promised” somehow never materialize. Even the most seasoned venture capitalists — people who live and breathe startup investing — don’t have a perfect batting average.
Even the Pros Miss — Often
Case in point: I recently saw a LinkedIn post summarizing data from over 12,000 middle- and top-level VC professionals. These are the career investors who’ve climbed to Director, Principal, or General Partner at U.S. firms between 1996 and 2025. The numbers? 46% of them — nearly half — have never been associated with a single successful deal by one of the three most generous definitions of “success” in the business.
Let that sink in. If you were one of those people — a senior VC with an entire career built on this — the odds are still about even that you’ve never had a real win. So why, exactly, would you feel certain you’ve found your golden ticket? The truth is, you’re probably not special… at least not yet. That’s not an insult. It’s a statistical reality.
Patience Pays — and Keeps You in the Game
Here’s where my favorite investment line comes in: “You’ll seldom rue the day you underinvested.” Or, to put it in plainer, stickier terms: you will never regret investing too little in an opportunity.
Private business investing is a long game — ten years or more to be an “overnight success.” The beauty of underinvesting early is that it buys you time. Time to learn the craft. Time to figure out whether you are an outlier or whether you’re better off finding the outliers to back for the rest of your life.
Putting a small stake in your first few deals keeps your wallet intact and your seat at the table. It allows you to see the arc of execution, not just the sparkle of the idea. And it lets you discover that this “once-in-a-lifetime” opportunity… might actually be the first in a line of many, each with its own lessons and possibilities.
So yes — try it. Go for it. But remember: in the early stages of your investing career, the wins will come more often from the deals you walked away from or kept small than the ones you maxed out.
