I don't take enough risks (and neither do you)
A non-New Year's, New Year's post
👋Hey guys,
I hope all your 2026’s are off to a great start! I’m excited to see what comes of Uncredentialed over the next year. I spent some of my extra time over the holidays brainstorming some fun things to try out as the newsletter continues to grow. For now, I put together a new logo!
Let me know your thoughts, but I felt like this matched the whole idea of Uncredentialed a little better.
Heading into 2026, I’m planning to continue the same cadence of a full-length post (usually) on Tuesdays along with my weekly No Creds Notes posts on Thursdays. For the full-length posts I’m thinking I’ll alternate between more detail-oriented, technical pieces (think my data center series, my Kalshi deep dive, or last week’s stablecoin post) and higher level, “thinking” pieces (more similar to my Mission as an API post or today’s post), but that’s more of a general rule than a strict guideline.
Soap box aside, let’s get into it.
If this is your first time here, welcome to Uncredentialed! I write weekly to an audience of founders, GPs, LPs, and analysts, bringing them up to speed on current topics in the world of tech, startups, and strategy that might fall outside their knowledge wheelhouse. If that sounds valuable to you, join 92 others who’ve subscribed already!
New Year’s resolutions usually suck.
They get bogged in the minutiae of “drinking 64oz of water” or “hitting the gym 5 days a week,” rarely leading to lasting change. We dance around the end goal, choosing habits that are directionally correct rather than just deciding who we want to be.
I believe deciding on an identity is infinitely more rewarding than deciding on a to-do list.
Saying “I’m going to go to the gym because I want to be healthy” implies that “healthy” is a reward you might earn later. In contrast, saying “I’m a healthy person, so I go to the gym” flips the script. If you’re a healthy person and you skip a workout, it should rub you the wrong way. Reality is out of alignment with your identity. You have 2 choices, either change your identity or get out there and fix reality.
To that end, I’m leaning into a more risk-on identity this year. Here is why most of us are miscalculating the math on risk, and how our evolution is holding us back from our own upside.
Take More Risks
For a century, American football was a game of “field position.” Coaches played not to lose, regularly electing to punt or otherwise play conservative to avoid putting the other team in a position to score, rather than take extra shots at scoring themselves.
Then, in 2002, UC Berkeley economist David Romer published a paper titled, “It’s Fourth Down And What Does The Bellman Equation Say?” To sum it up, the Bellman Equation said that coaches were far too conservative.
By punting on 4th-and-short, coaches were overvaluing the downside (giving up field position) and completely ignoring the upside that comes from staying on the field.
This loss aversion mentality extends well beyond the gridiron. Across the board, humanity has a hardcoded tendency toward risk aversion that caps our potential. We are programmed to “punt” our best opportunities because we’re afraid of the field position we might lose if we fail.
The risks we face largely fall into 3 main categories:
Social Risk
Financial Risk
Physical Risk
Social Risk
We’ve all felt it: the dry throat before a speech, the hesitation to talk to a stranger, or the “delete draft” energy before posting something on Substack.
Evolution hardcoded this anxiety into us. Thousands of years ago, we lived in small tribes. If you made a social gaffe that got you kicked out, you were dead. No food, no protection, no mate. Social rejection was a literal death sentence.
We still run on that prehistoric software in a 2025 2026 world.
In a world of 8 billion people, the downside of a “flop” rounds to zero. A typo or a nervous speech won’t kill you, but your brain still triggers a rush of cortisol as if your life is at stake.
Meanwhile, the upside of social risk is near-infinite. Look at Packy McCormick. Not Boring started as a newsletter for friends and family. By putting his thoughts out there (taking the social risk of being “wrong” or “ignored”) he ended up building a multi-million dollar business and a VC fund. Or look at Jason Levin, who went from a broke writer to raising $4M for his meme-making startup by following what he calls “The Cool Shit Law”: Make cool things and talk to cool people every day.
Taking social risk is about increasing your surface area for luck. Every post, every DM, and every conversation is a lottery ticket that costs nothing but a moment of temporary embarrassment and pays for itself immediately with interesting conversations and new perspectives.
In a world where “memes make millions,” we should spend more time fun-maxxing and less time worrying about a downside that doesn’t actually exist.
Financial Risk
In Finance 101, they tell you that more risk equals higher expected returns. When you’re young, you’re told to lean into risky assets because you have time.
However, all risk is not created equal. While social risk has zero downside, financial risk can actually hurt. Fear of that pain leads most people to play it too safe by sticking directly to consensus opinions. As Bill Gurley says, “You can’t make money with a consensus accurate opinion.”
If you’re (like me) in your capital accumulation phase of life, the S&P is fine, but it won’t change your life and won’t get you involved in the process. Differentiated returns come from high concentration on non-consensus bets.
Personally, I’m leaning into early-stage startup investing. I’m moving away from the “safe” recommendation of a 5-10% allocation and hoping to put 50%+ of my portfolio in the space1.
Why? The Power Law.
Venture is a funny dichotomy of pure optimism towards building the future while simultaneously seeing most investments go to zero. To be clear, it’s not charity, the rare big winner in VC wins so big that it pays for all the losses and more.
My plan is to find startups in industries that aren’t popular, being built by uncredentialed founders2. The belief being that despite higher failure rates because the industries are less certain, the higher ownership in the winners should make up for it. Plus, doesn’t investing in nuclear fusion, the OASIS, or modernized metal factories just sound more fun than another B2B SaaS3?
Your “risk-on” might look a little different. Maybe it’s real estate or a concentrated bet on a technology you understand deeply, but if you’re still early in accumulating capital, “safe and diversified” investing could actually be your biggest risk4.
Physical Risk
Physical risk has followed the opposite path of social risk.
For our ancestors, physical risk had a tempting payoff. Taking down a mammoth meant food and status. Today, taking physical risks has the same existential downside (death) with almost 0 upside.
So physical risks are actually a space I’d say we as individuals don’t need to be taking more risks5. Society has evolved to a point where we are able to meet our needs without putting our lives on the line. And who knows, if the AGI bulls are right, maybe one day we’ll hit a point where all our financial needs are met too, leaving us with nothing to do but fun-maxx and take social risks.
Because of our natural bias toward loss aversion, we all tend to play the game of life for “field position” rather than for the touchdown. We over-index on the embarrassment of a failed post of the volatility of a concentrated portfolio, while ignoring the staggering cost of the opportunities we never took.
This year, I want to be someone who plays for infinite upside and gets excited, rather than nervous, about risks.
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Note: I fully recognize this could be a dumb idea that backfires and am not saying anyone else should be taking on this specific risk
If this thesis sounds interesting to you, shoot me a reply (or text or DM)! In the coming years as Uncredentialed grows, I may try out some syndicate deals if there’s interest
Not an investor in Nox, just think it’s cool to see a YC-backed metals factory
But remember that Bill Gurley’s quote encouraged being both non-consensus and accurate. Don’t just throw your money away on some gamble. Learn how unpopular stuff works and reach differentiated insights
Now, in aggregate (in the US), I’d argue the opposite. Everything from our approach to construction to approving new medicines and plenty more is too physical-risk-averse and limits progress. But that’s a story for another post.