Three Years of Trading

DISCLAIMER: This is NOT financial advice, perform your own due diligence!


the old exchange of amsterdam by job adriaensz berckheyde (~1670)

The Journey

From mid-January 2023 to April 2026, I have been actively managing my own trading portfolio. It has been a wild ride of wins, losses, and deep reflection. After three years, I wanted to take a step back, look at the numbers, and document the core philosophy that will guide my future investments.

Before getting into the details, I want to be clear that the portfolio I actively manage represents only about 15% of my total market exposure. The rest is either managed by professionals or, more commonly, held in my 401(k), Roth IRA, and safer assets like gold ETFs. This self-directed slice is where I experiment, learn, and take more concentrated bets, and it is where the results I am about to reflect on come from.

Numbers matter. A good story creates attention and conviction, but hard facts decide whether that story deserves your capital. Right now, my active trading accounts are compounding at an annualized return (CAGR) of 10.60%. Most of these returns came from a handful of solid moves in Google, Palantir, Applied Optoelectronics (AAOI), Tesla, EchoStar, and ASML. That number outpaces inflation, which averaged roughly 3.4% annually during this period, but the real story is in the gap between my performance and the broader market.

The Scorecard & Benchmark

To really understand my performance, I had to measure it against a passive benchmark, the S&P 500. From January 2023 to April 2026, the market posted a cumulative return of 73.54% with a CAGR of 18.48%. In comparison, my 38% cumulative return (10.6% CAGR) lagged the benchmark by nearly 8% annually.

If I had done absolutely nothing and simply held an index fund, my total returns would have been nearly double what I achieved. Beyond the capital, there is the cost of time. I spent weeks of full-time equivalent during those years researching and trading, only to underperform the simplest strategy available, which is to buy and hold. That 8% gap is not just a number. It is a direct reflection of specific moments where my process broke down.

The Anatomy of a Mistake

For all the wins, my critical blunders were rarely about picking the wrong asset. They were almost always about having the wrong process.

1. The Panic Exit (Bitcoin):
I bought most of my Bitcoin at an average price of around $100k in 2025. At the time, it made up 15% of this portfolio, but after some time, I started feeling like it was too much exposure. So I started scaling it back for rebalancing, and I had trimmed it down to 9% by January 2026. Then, in February 2026, Bitcoin had a massive volatility hit, with a price drop to below $60k after an all‑time high of $125k in October 2025. In a moment of stress, I panicked and sold near $62k just to get rid of the weight. I eventually bought back in, but only at around 30% of my original size, making it only 2.7% of this portfolio. I let temporary discomfort dictate a permanent capital decision, locking in a painful realized loss on the portion I sold.

2. The Mismanaged Horizon (AAOI):
I recently made a good profit on AAOI, but I sold my entire position when the price action became “uncomfortable.” It was at an all-time high, and I was convinced that it could not go higher, so I treated a high-conviction play like a one-month flip and sold all my holdings when the stock hit around 140 dollars per share. A day later, the stock kept ripping higher, which led me to feel a deep sense of regret. I had bought it without a clear category in mind, let the price action make the decision for me, and used an “all or nothing” exit instead of scaling out in tranches. I still walked away with a solid overall gain on the trade, but the opportunity cost of selling early left a massive amount of profit on the table.

Borrowed Conviction

Both of those mistakes share the same root cause. I was acting on borrowed conviction.

Early on, I anchored myself to legends like Warren Buffett, focusing on quality, value, and the “Rule #1” of never losing money. In October 2025, I began following Michael Sikand, who is brilliant at surfacing asymmetric bets in defense, space, and AI infrastructure. Stacking those influences led me to my most important realization. You can borrow someone else’s ideas, but you cannot borrow their conviction or their risk tolerance.

AAOI taught me this the hard way. A stock might be a perfect play for someone else, but if it does not fit my time horizon, I will inevitably panic when volatility hits. The same thing happens if I never clearly defined my time horizon, or if I do not fully own the thesis.

Refining the Identity

That realization forced me to rebuild my investing identity. My philosophy is now built around investing aggressively where my competence, conviction, and worldview meet. I have shifted from a trader chasing price action to an allocator betting on utility, a dual-track mission of solving present-day bottlenecks while building the architecture for the future. I focus entirely on the “Deep Tech” stack, spanning these core areas through that lens:

  • AI Infrastructure: The economic multiplier. I am investing in the engines of human productivity that allow us to do more faster and with less.
  • Defense & Autonomy Robotics: The physical multiplier. The solution to labor shortages and the evolution of physical work.
  • Scalable Space Businesses: The resource multiplier and the ultimate hedge against planetary risk and technological stagnation.

Beyond these pillars, I have also decided to step away from crypto. I still find Bitcoin interesting and worth considering to a certain extent, so I plan to keep what I currently hold, but moving forward, I will not have any more capital exposed to the space in this portfolio. It has always given me little to no real return, and it is something I simply do not want to expend mental energy on. My focus is now entirely on the deep tech stack, where I see clear, tangible utility.

The grand vision and future utility get a company on my radar, but the hard numbers decide its place in my portfolio. To bridge the gap between my current performance and the market, I’ve distilled my experiences into a personal rulebook.

The Rulebook

I am far from the best trader or investor, and I will never claim to be. However, I want to share the lessons and advice I have compiled over the last three years. These are the rules that have helped me, the rules I try to stick with, and the rules that push me to be better.

On Capital & Risk

  • Preserve the Seed: As Warren Buffett said, “Rule #1: Never lose money. Rule #2: Never forget rule #1”. Staying in the game matters more than chasing a few huge wins.
  • Size for Survival: Know your position size before you enter. Never bet what you aren’t okay with seeing cut in half or even drop to zero in some cases.
  • Liquidity is Power: Cash is king. Net worth on a screen is fake. liquid assets are power.
  • Leverage is a Tool of Destruction: It can turn a good idea into a total disaster.

On Psychology & Discipline

  • Kill the Ego: Don’t confuse a bull market with skill. Stay humble when winning and disciplined when losing. As Andrej Karpathy said, “Don’t compare yourself to others. Compare yourself to you one year ago”.
  • Learn to Sit Still: Impatience ruins more decisions than ignorance. Sometimes the best move is to do nothing.
  • The Hindsight Trap: No one times the top or bottom perfectly. As David Grann wrote, “History is a merciless judge… wielding the power of hindsight like an arrogant detective”.
  • Emotions are Noise: If you feel hype, greed, or revenge, step away. Be cold, objective, and informed.

On Strategy & Execution

  • Own the Thesis: Have a clear reason to enter and a clear reason to exit. If you can’t explain both, do nothing.
  • Trade What You See: As Peter Brandt said, “Trade what you see, not what you think”. Facts change, and you must be willing to change with them. Don’t marry a narrative if the numbers show real weakness.
  • Nothing Goes Up Forever: You cannot always just hold. Assets do not endlessly go up and break new records every year/decade. Eventually, you have to sell. Taking profits is how you lock in your success and free up capital to aim for new opportunities.
  • Avoid Forced Entries: Missing a winner is better than forcing a bad entry.
  • Scale, Don’t Snap: Use tranches to enter and exit. All-or-nothing moves are for gamblers, not investors.

Why I Keep Going

Rules only matter if you stay in the game long enough to apply them, and that is exactly why I keep going. I am still in my 20s. I have no massive responsibilities just yet, and I have a long runway ahead of me. This is the absolute best time to take risks. The potential returns I could lose by playing it “too safe”, not just in stocks but in life, are far larger than the capital I can lose right now.

This is the same logic that drove me to start my startup, Osgil, at 24. It is also why I maintain a “risk sleeve” in my portfolio while my 401k, Roth IRA, and safe assets like GLD and VXUS handle the foundational growth.

I have always followed a baseline set of rules, but moving forward, I will be much more disciplined about the process. This new rulebook is built on both the wisdom of the greats and the personal scars of exactly what didn’t work.

What’s Next

The execution of this rulebook is already underway. I am moving away from scattered trades and building a structured, concentrated, thesis-driven portfolio.

I am building a long-term backbone in deep-stack AI and semiconductor infrastructure, treating them as the ultimate economic multipliers. Alongside that, I have already made heavy investments in the physical and evolutionary layers, specifically establishing significant positions in scalable space infrastructure and defense autonomy. These aren’t short-term flips; they are calculated, multi-year bets on the future. I may be wrong, but the upside far outweighs the downside, so the risk is worth taking.

The biggest change isn’t just what I am buying, but how. Every new position now comes with a predefined time horizon, a clear reason to own it, and strict sell rules established before the capital ever leaves my account.

I look forward to tracking how these high-conviction moves play out, sticking to the thesis through the volatility, and reporting back on this portfolio in the years to come.