How I’m Investing Outside My Business in 2026

I believe you should be building your personal balance sheet alongside your business. This is one of the eight pillars in the financial mastery framework I’m writing about.

If you’re betting everything on a future exit that may or may not happen, you’re taking a massive risk. Building your personal net worth alongside your business gives you optionality, security, and lets you make better decisions because you’re not desperate.

So I’m going to start sharing what my portfolio looks like and tracking my performance vs. the S&P each year. Here’s my 2026 baseline.

How I Calculate This

Quick caveat: I don’t include my primary residence, physical possessions, or my business in these numbers.

Your house is consumption, not investment. Physical possessions aren’t investable assets. And your business is illiquid and volatile until you sell it—including it can give you a false sense of security. I think it’s cleaner to track what you have in actual liquid investments separately.

The Breakdown

3.5% individual stocks.

I think investing should be 90% boring and 10% bold. You should have a few bets if you have deep conviction in a space that you think will outperform, but they should be few and far between. And you should make sure the position size is large enough that if you’re right, they actually count.

My two positions: Shopify and Cloudflare.

Shopify is the closest thing to a monopoly in ecommerce outside of Amazon. There’s just not another good option in the hosted software space, and it’s getting more entrenched every year. I’m long Shopify.

Cloudflare I know a little less about their internals, but everyone I’ve talked to loves them and my own experience has been great. They do a lot of things well and seem to have a strong culture.

63% index funds.

Mostly US total market, about 15% international, zero bonds. Boring and intentional. I’m working to increase international exposure a bit—international stocks ripped this year and I think there’s still room on a valuation basis, plus it’s good diversification. But the core is simple: broad market index funds, low fees, hold forever.

12% crypto.

Primarily Bitcoin and Ethereum. Still believe in the original thesis as a non-institutional store of value and a hedge against government monetary policy gone wrong.

That said, it’s a little unnerving that it’s acting more like a risk asset than digital gold lately. Gold was up 70%+ over the last 12 months. Bitcoin hasn’t kept pace, which is strange for something that’s supposed to be “digital gold.”

But I like the fundamentals long-term, I have some gains I don’t want to take the tax hit on, and it’s a meaningful diversification play as an anti-institutional hedge. The more institutions buy it and the bigger it gets, the lower the upside and more volatility—but I’m still holding.

11% real estate.

One rental property. Honestly not a great pure investment—more a house we love that we’re renting out until we decide what to do with it.

Setting up and running an Airbnb for the past four months has given me a new appreciation for how much work short-term rentals are, even with someone else managing it. It’s also made me appreciate what a good deal Airbnb is as a traveler—walk in, use it for a few days, pay, and leave without dealing with any of the headaches.

9% cash.

I like having a cushion, especially with markets at all-time highs. Half of this is earmarked for a “big bets” fund—waiting for one or two high-conviction opportunities where I can bet meaningfully. Looking for those in 2026.

Less than 1% private investments.

Three small bets on founders I believe in: IntelliGems, Postpilot, and Kanpai Foods. All three have built great companies.

I haven’t put a ton of money to work on the private side. It’s interesting when you have domain expertise and get opportunities with people you trust, but it’s a small part of the overall portfolio.

Two Sells This Year

Tesla. I held Tesla for about four years. Good run. But I sold this year for a few reasons.

My original thesis was the product—the car was so good and people were so happy with it. But the company seems to be shifting from being a car company to a big bet on robotics, self-driving, and automated taxis. Not that those won’t work, but my original thesis has changed and I haven’t done the homework to evaluate if those other things are worth a trillion-plus valuation.

There’s also increasing key man risk with Elon. He’s getting older, has worked insanely hard his whole life, and is spreading himself across multiple companies. That risk grows every year.

At a trillion-plus valuation with my original thesis changed, felt like a good time to exit.

Airbnb. This was one of my worst decisions recently. I made a knee-jerk investment—heard it recommended by someone and bought it because I wasn’t sure what else to do with the money. Classic mistake.

I held it for six to twelve months, broke roughly even, and sold. After setting up my own Airbnb this year, I realized I’m not as bullish on the company as I thought. They’re not terrible, but they’ve been lackluster in growth for years and I’m not sure what the catalyst for change is.

The biggest lesson: don’t make 5-out-of-10 conviction bets on individual stocks. If you don’t have high conviction, just put it in an index fund.

That’s the Baseline

I’ll report back at the end of the year on how this performed vs. the S&P.

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