Why I’m Not Adding a Third Position: A Concentrated Investor’s Comparison of WISE, Duolingo, and Nubank

There’s an ongoing pressure, both internal and external, to diversify—especially once your first two bets begin to work. And lately, that pressure has grown louder as Hims & Hers and Oscar Health have both delivered substantial momentum. I’ve asked myself the obvious question: should I add a third position? More importantly, does adding a third stock increase my chances of achieving financial independence, or does it dilute the asymmetric opportunity I’ve already captured?

I approached this question methodically. I challenged three widely admired businesses—WISE, Duolingo, and Nubank—against one another. Then I tested the best of the three against Hims and Oscar. My goal was to see if any of them deserved to become my third holding. The answer? None of them made the cut.

This is the story of that process.

WISE: Brilliant Product, Misplaced Listing, Lacking Asymmetry

I’ve followed WISE (formerly TransferWise) closely. I even wrote extensively about it in earlier notes. Their business model is efficient, transparent, and clearly superior to traditional banks when it comes to cross-border payments. Their mission resonates. Their customer satisfaction is high. But the business, in my view, has one fatal flaw: it is capped in upside and structurally unlikely to 10x in a reasonable timeframe.

Let’s start with geography: WISE is listed in London—a market that, unlike the U.S., structurally limits the valuation of tech-forward, growth-centric, founder-led businesses. The U.K. exchange tends to reward profitability and dividends, not optionality and narrative. The multiple compression risk is persistent. Unless WISE relists in the U.S., the ceiling remains low.

Now compare WISE to Hims & Hers: HIMS has an enormous retail tailwind, growing virality, short squeeze potential, and the potential to build the “Netflix of healthcare.” They are aggregating demand and vertically integrating, targeting essential human needs in a platform model that could lead to dominant economics.

Compare WISE to Oscar Health: Oscar operates in the single largest and most broken system in America—healthcare. Unlike cross-border payments, health insurance is a legal mandate. Oscar is riding a wave of structural tailwinds—policy, AI, and demographic. And they have Thrive Capital and Josh Kushner as long-term, deeply aligned backers.

Meanwhile, WISE operates in a commoditized space. The pricing power is limited. The moat is usability and cost transparency, not regulatory capture or essentiality. I don’t see the kind of explosive optionality here that would justify a position in my ultra-concentrated strategy.

Verdict: Strong business, but no match for the asymmetry I see in HIMS or OSCR.

Duolingo: Great Product, But Optional, Not Essential

Duolingo is a joy to analyze. It’s one of the best consumer tech companies to emerge from the last decade. The product is sticky, gamified, and backed by world-class execution. Revenue is growing fast. The brand is strong. The monetization engine—freemium plus subscription—is humming. And yet, for all that, Duolingo is not essential.

Learning a language is optional. It can be postponed, paused, or abandoned. Nobody dies if they stop using Duolingo. That’s a tough business to compare to something like health.

Compare Duolingo to Hims & Hers: HIMS provides care for mental health, sexual wellness, hair loss, weight loss, and primary care—all things that are urgent, emotional, and inescapable. Duolingo gamifies a luxury. Hims treats necessity. The risk-reward just isn’t in the same league.

Now look at Duolingo versus Oscar: Duolingo builds a habit. Oscar builds infrastructure. Oscar doesn’t just have customers—it has regulatory tailwinds, long-term policy advantages, and incumbents who are actively exiting the ACA space. In contrast, Duolingo faces competition from free alternatives, cheap YouTube content, and an audience that churns at the slightest distraction.

Duolingo’s market cap is already sizable. While the business can grow, and likely will, I don’t see a credible path to 10x from here without massive TAM expansion or new business lines. It’s a fantastic company. Just not one I’m willing to bet my financial freedom on.

Verdict: Love the product, but the optionality isn’t strong enough to warrant capital.

Nubank: The Darling of LatAm Fintech, But Overcrowded Waters

I admire Nubank deeply. They changed the game in Brazil. They made banking accessible, elegant, and customer-centric. Their first-mover advantage is real, and the user experience is excellent. But their business lives in an ecosystem where imitation is easy and competition is intense.

Nubank is already big. They are already well-covered by Wall Street and celebrated by retail investors. Their path forward is about execution, not discovery. And that’s where I see friction.

Compare Nubank to Hims: Nubank is a bank. Hims is building a health platform that could grow into diagnostics, chronic care, and employer-based telehealth. Hims owns customer attention and emotion. Nubank handles payments. The emotional differentiation is stark.

Compare Nubank to Oscar: Oscar is still underestimated. Most people have no idea how radically they’re improving patient outcomes per dollar spent. Meanwhile, Oscar’s biggest rivals are giving up. That’s the sign of a massive opportunity. Nubank, by contrast, is facing more players, not fewer.

The unbanked population in Latin America is going digital—but they go where the hurdles are lowest. Many users prefer platforms that don’t require formal ID. Nubank’s onboarding is better than most, but new niche players are fast and flexible. The moat is weakening. And crucially, I don’t see a clear near-term catalyst that will drive re-rating or market surprise.

Verdict: Brilliant business, wrong environment for asymmetric upside.

The Final Call: No Third Position

After comparing WISE, Duolingo, and Nubank—first against one another, then against my two holdings—I reached a clear conclusion:

None of them are able to match the risk-reward, the asymmetry, and the catalyst-driven potential of Hims & Hers and Oscar Health.

Why should I dilute my strategy just to fill a third slot?

• HIMS has short interest, a viral consumer wedge, and growing brand power.

• OSCR has industry tailwinds, political protection, and room to surprise.

• Both stocks are founder-led, misunderstood, and mispriced.

• Both address essential needs, not optional desires.

I believe I will make more money putting incremental capital into HIMS and OSCR rather than forcing a third name into my portfolio.

This is not indecision. It is discipline.

I’m not here to look diversified. I’m here to get rich—by being concentrated, asymmetric, and right.

So I’m staying with my two: Hims & Hers and Oscar Health.

That’s my punch card.