Side Quests
Tings Newsletter #31
If you’re new here: I’m Michael Karnjanaprakorn. Previously, the founder of Skillshare, Otis and Turing Capital. This is my monthly newsletter, a list of ~20ish “tings” I find interesting across life, work, tech, and everything in-between. If someone forwarded this to you, subscribe along with 5k+ others here.
What’s new? I’ve been splitting my time between investing and advising. Put incubation on the back-burner to focus on helping early-stage founders with strategy, fundraising, and growth. Mostly helping them get from 0 to 1. Made two angel investments and have been diving into research on public and private investing firms. Right now, I’m volunteering my time to others, and it’s been surprisingly fulfilling.
I agree with this barbell approach: “Either go very early or very late. Cheap or super premium. Very small or very big. - investing (very early stage or public markets) - careers (deep specialist or broad generalist) - education (self taught or top-tier). And finally, in life strategy: either optimize for freedom (time, simplicity) or for scale (impact, wealth). Comfortable middles rarely compound.”
I’ve been thinking about my own barbell approach to life. On one end, I’m investing. On the other, I’m chasing personally interesting side quests, like trying to become a pro Magic: The Gathering player. I’ve realized the key is committing to something long enough for it to compound, instead of constantly exploring new things.
Speaking of side quests, I’ve been following UFC fighter Payton Talbott (recently featured in the New York Times). He breaks the usual hypermasculine fighter stereotype. He’s rumored to be dating Frank Ocean (one of my favorite artists) and is a legit fighter, but what really caught my attention was his idea of side quests like working on a new album, skateboarding, and other creative hobbies. He balances the intensity of fighting in the cage with ways to express himself outside the cage.
I’ve been listening to the updated Navalmanack interviews on Smart Friends. One thing that stuck with me was Naval rethinking his old definition of wealth. He used to say wealth was “assets that earn while you sleep,” which came from wanting to escape the nine-to-five and do the least amount of work. It was a practical definition, optimized for making money and gaining freedom. But now he points to David Deutsch’s definition as “the set of physical transformations you can bring into existence.” In other words: how many things can you build, create, or improve?
I’m on a 24-day streak using Rosebud, an AI journal that “helps users identify and alter unhealthy thought patterns and behaviors.” What makes it powerful for me is its memory — it saves every entry, tracks patterns, and offers personalized suggestions. It’s helped me break bad habits, reframe negative thoughts into positive ones, and keep my mental state in a much better place. Highly recommend.
Just as you diversify your investments, people are starting to diversify their passports.
This is an extremely bearish and pessimistic take on the market. It argues that the U.S. is already in the early stages of a real recession masked by inflated markets and delayed effects of high interest rates. The predicted chain: rising defaults → overvalued assets → Fed intervention through money printing → temporary market lift → lasting inflation → widening inequality. Whatever side you’re on, it’s worth straw-manning the other side to understand it, but be careful taking advice from anon accounts on X 😆
Just finished reading The Trading Game by Gary Stevenson — solid 4/5. It’s about his experience as a trader navigating the financial system and how it shaped his views on inequality and markets. I didn’t realize until the end that the author is the same Gary’s Economics guy on YouTube, the one who breaks down complex finance and econ topics in simple, relatable terms.
Leopold Aschenbrenner is a former OpenAI researcher who launched a hedge fund inspired by his essay Situational Awareness. His fund posted +47% in the first half of 2025 by focusing on the broader AI picks and shovel plays including semiconductors, data centers, and the power grid. Here’s the latest holdings.
“Cursor’s Problem,” argues that while startups focus on product/market fit, AI companies need business model/product/market fit even more. The key insight: anytime “unlimited” appears in a variable-cost business, product/market fit becomes a permanently open question.
Hawaii has been showing up in my life a lot lately. I watched a great documentary called Shark Whisperer. It follows marine conservationist/activist Ocean Ramsey who swims with great white sharks as a way to protect them from being hunted and endangered.
One of the best shows I’ve seen in a while is Chief of War, produced by Jason Momoa. It’s like Game of Thrones but set in early Hawaii. My favorite scene is when the two chiefs talk shit to each other on the battlefield before going to battle. I looked into it and it’s a ceremonial pre-battle tradition in Hawaiian culture meant as psychological warfare.
A new UFO video shows what appears to be a missile deflecting off a spherical object. The footage, shown at a Congressional hearing, captures a US Reaper drone firing a Hellfire missile at the unidentified object off the coast of Yemen in October 2024. Defense experts noted that Hellfires usually cause major destruction on impact, yet this one seemed to bounce off. Add this to the “more proof” bucket.
“This video has been making the rounds, and what this teacher is saying I’ve heard from many, many teachers in the US.“ TLDR: How phones have replaced developmentally necessary aspects of childhood.
Just got the new Coinbase One card which offers 4% cashback in Bitcoin. I like this as a replacement for my Chase Sapphire Reserve as my points continue to get devalued. My goal for this next year is to use all of our points for travel. You get like 1.5x on Chase but 4x on Coinbase (with potential upside) seems like a much better deal.
I still use Todoist for task management, but I haven’t found a reliable notes system. I went back to a simple list setup and signed up for Workflowy again. They’ve made so many updates: Quick Add, Daily Journal, and new AI features. Excited to give it another try.
Some of the companies I advise are looking for a PT Growth Marketer (digital app) and PT CFO (D2C brand). DM me if you’re interested or have a great rec.
“How does he keep his cat safe outdoors? With a $125,000 catio.”
Loved this line from thiccy’s latest essay: “reading fed the desire for knowledge and understanding, writing fed the desire truth seeking and creation, and together they serve the search for beauty and form.”
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Love this!
Glad you’re finding fulfillment in advising (I thought it sucked 😂).
I’d be curious to hear more about… what’s it like going deep into an obscure hobby like Magic?