Outing Myself: My Biggest Investing Mistake in 15 Years
Everyone talks about their winners. The multibaggers. The times they “saw it coming.” Their deep insight into macro conditions, supply chains, regulatory shifts. You name it. Most of us—especially in public—prefer to wear our investing successes like a badge of honor.
But that’s not what this post is about.
This one’s about my biggest mistake. The kind of mistake that humbles you. That makes you rethink everything. That you carry forward as a scar—but also as a guidepost.
This is about New Fortress Energy (NFE).
Everything Looked Perfect
If you know me, you know I don’t invest lightly. I’m highly concentrated. I don’t spread my bets. I build conviction over time—buying in layers, over quarters, even years. But when I commit, I commit deeply.
New Fortress Energy ticked every single box I look for:
Founder-led: Wes Edens. The man built Fortress Investment Group, co-owns the Milwaukee Bucks, and has an undeniable track record in infrastructure and finance. He had real skin in the game. Bought in early. Knew capital markets like the back of his hand.
High Insider Ownership: Exactly what I want to see—alignment. I want insiders who feel every tick of the share price in their personal net worth.
Durable Employees: I stalk companies. I read every 10-K, every analyst call. I follow employees on LinkedIn. I check tenure, culture, how often key staff turn over. At NFE, people stayed. That says something.
Massive Total Addressable Market: Bringing cleaner, safer, more reliable energy to emerging markets. You don’t need an MBA to know how big that is. Growing economies. Growing populations. Growing energy demand.
Strategic Moats: LNG terminals aren’t lemonade stands. They’re heavily regulated, capital-intensive, politically sensitive projects. You don’t just build one overnight. NFE had them, and most compellingly, had built out key facilities in Brazil, a country historically dependent on hydropower. A massive opportunity to provide baseload energy security to an entire economy.
I Did the Work—All of It
This wasn’t a FOMO play. I wasn’t chasing a trend.
I followed this company for two and a half years before going all in.
Listened to every earnings call.
Read every investor deck.
Ran valuation models.
Studied regulatory timelines.
Compared LNG terminal construction cycles across peers.
Monitored employee activity.
Knew when they opened their offices and when the lights turned off.
This was deep due diligence.
And yet, I got crushed.
What I Missed
What I failed to understand—what didn’t show up in any model or transcript—was the culture.
Specifically: a culture of overpromising and underdelivering.
On the surface, delays in the energy sector are normal. It’s construction. It’s heavy industry. It’s people. It’s regulation. And yes, we’re talking about emerging markets where things move slower, approvals stall, and coordination can be a mess.
But over time, a pattern emerged.
They consistently missed timelines for facility openings. Management projected free cash flow that never materialized. And when delays were reported, they often seemed to downplay known issues. They gave shareholders an illusion of precision, rather than transparency.
In hindsight, I believe they knew more than they disclosed. There’s a difference between being optimistic and being misleading. And I didn’t calibrate that distinction properly.
A Hard Lesson in Unknowns
When you’re a concentrated investor, your mistakes are magnified. I wasn’t spread across 10–15 positions. This was one of my core ideas.
And it became my biggest loss in 15 years of investing.
What hurt wasn’t just the financial hit—it was the realization that I did everything right, and still ended up wrong. That’s a brutal but necessary truth of this game.
And it taught me a few things I’ll carry forward:
Execution > Vision: A great market, a great founder, a great idea—they mean nothing if execution falters.
Culture matters more than presentations: The slickest investor decks won’t show you how people actually behave when timelines slip.
Some things can’t be known upfront: There will always be unknown unknowns—especially when government bodies, infrastructure, and emerging markets are involved.
Why I’m Sharing This
Because this is a space where I want to be real.
Too many people act like they always knew. Like they can predict geopolitical risk, tariffs, bond markets, and a dozen other macro variables—flawlessly. That’s not me.
I’m here to share the journey. The good and the ugly.
And truthfully, I’ve learned more from my mistakes than from my wins. Success feels great, but failure forces you to dig deep, to ask tougher questions, to get better. It’s uncomfortable—but it’s necessary.
And no, the answer isn’t to suddenly diversify into 20 tickers to reduce the blow of a single miss. That’s not who I am. That’s not how I invest.
The answer is to slow down.
To watch a company just a little longer before fully committing. To look past the market opportunity and the charisma of the founder—and get a true feel for the company culture.
Are they just selling a vision? Or do they actually walk the talk?
Do they hit milestones? Do they execute? Or do they keep pushing deadlines without owning up to what’s really happening?
That’s the filter I’ve built into my process since New Fortress Energy.
Today, I lean more toward companies that sandbag. That underpromise and overdeliver. That give realistic, even conservative guidance—because those are the companies that surprise to the upside. I’m wary of the ones that sell the Goldilocks scenario. I’ve seen what happens when that story doesn’t hold up.
The Takeaway
This was my biggest loss. But it might also be one of my most valuable investments—because the tuition I paid here will compound in how I approach every idea going forward.
We all like to talk about conviction. But true conviction requires brutal honesty—especially with yourself.
Thanks for reading.