This isn’t financial advice.
It’s just what I’m doing with my own capital — based on where I see risk/reward skewed hard in my favor.
Every position below reflects high conviction, asymmetric upside, and a long-term belief in the management team, business model, and market potential. I’m not chasing trends. I’m looking for setups where the narrative hasn’t caught up yet.
Here’s what I’m buying right now:
$LMND – Lemonade
Reinventing insurance from the ground up with an AI-first model that scales faster and cheaper than legacy carriers.
Using behavioral economics and machine learning to compress underwriting and claims into seconds — an industry still stuck in days.
Viewed as a “cute app” by incumbents, but quietly building a vertically integrated full-stack insurer across multiple lines.
As losses narrow and growth compounds, the market is still valuing it like a broken tech play — not a future GEICO.
If they win even low-single-digit market share in auto/home/renters, the upside is 5–10x from today’s base.
$HIMS – Hims & Hers Health
Direct-to-consumer model flips the healthcare system on its head — no gatekeepers, no stigma, no waiting rooms.
Building a digital wellness empire while legacy healthcare still sends faxes and makes you wait 3 weeks for a visit.
Market punished them for one GLP-1 headline — ignoring the fact that 90% of the business is thriving and expanding.
They’re not just selling pills — they’re capturing lifetime healthcare spend with subscription-like retention.
If HIMS becomes the CVS/Amazon of virtual care, this stock doesn’t just double — it explodes.
$SOFI – SoFi Technologies
Legacy banks are bloated, slow, and losing trust — SoFi is a full-stack digital alternative eating their lunch.
One of the few fintechs with a real bank charter and a profitable path in sight — the market hasn’t recalibrated for that.
Building an all-in-one money app that Gen Z and Millennials actually want to use — think Square meets JPMorgan.
Fee-based income + student loan flywheel + return to crypto creates a multi-pronged inflection point Wall Street is missing.
If SoFi is the front door to modern finance, this is still the ground floor.
$OSCR – Oscar Health
Healthcare hasn’t changed in decades — Oscar’s model actually puts users first through tech, transparency, and cost clarity.
Built from scratch to integrate insurance, telehealth, and value-based care — legacy players can’t retrofit that.
Market thinks this is “just another insurer” — but this is a software-enabled platform with compounding data moats.
Winning share in individual and small group markets where big insurers don’t want to innovate.
At scale, Oscar could be the Stripe of health insurance — invisible but critical infrastructure with asymmetric leverage.
Black Sheep Capital – Private Market Focus
We're backing founders who are building bold companies at the edge of what’s possible — in sectors where technology, regulation, and capital allocation are converging fast.
Our focus today is on:
Defense Tech – Dual-use and national security innovations
Biotech & Longevity – Fertility, wellness, and frontier human health
Industrial AI & Automation – Software eating manufacturing
Financial Infrastructure – The plumbing behind fintech and payments
Vertical SaaS – Deeply embedded software in outdated sectors
Consumer Platforms with Margins – Brand + product + retention in one
These are not consensus picks. That’s intentional. The upside is always greatest before the story changes — not after.
And if you’re subscribed here, it means you’re wired the same way I am:
You want early insight. High conviction. And you’re not afraid to think independently.
Individual deep dives on each of these coming soon. Let’s stay ahead of the noise.
— Connor