How I am Investing Exterior My Enterprise in 2026

I consider you ought to be constructing your private steadiness sheet alongside your enterprise. This is among the eight pillars within the monetary mastery framework I’m writing about.

In case you’re betting the whole lot on a future exit that will or might not occur, you’re taking an enormous threat. Constructing your private internet value alongside your enterprise offers you optionality, safety, and allows you to make higher selections since you’re not determined.

So I’m going to start out sharing what my portfolio appears to be like like and monitoring my efficiency vs. the S&P annually. Right here’s my 2026 baseline.

How I Calculate This

Fast caveat: I don’t embrace my main residence, bodily possessions, or my enterprise in these numbers.

Your own home is consumption, not funding. Bodily possessions aren’t investable belongings. And your enterprise is illiquid and unstable till you promote it—together with it may give you a false sense of safety. I feel it’s cleaner to trace what you will have in precise liquid investments individually.

The Breakdown

3.5% particular person shares.

I feel investing needs to be 90% boring and 10% daring. It is best to have a couple of bets when you’ve got deep conviction in an area that you just suppose will outperform, however they need to be few and much between. And it is best to make sure that the place measurement is giant sufficient that for those who’re proper, they really depend.

My two positions: Shopify and Cloudflare.

Shopify is the closest factor to a monopoly in ecommerce outdoors of Amazon. There’s simply not one other good choice within the hosted software program area, and it’s getting extra entrenched yearly. I’m lengthy Shopify.

Cloudflare I do know rather less about their internals, however everybody I’ve talked to loves them and my very own expertise has been nice. They do lots of issues properly and appear to have a robust tradition.

63% index funds.

Principally US complete market, about 15% worldwide, zero bonds. Boring and intentional. I’m working to extend worldwide publicity a bit—worldwide shares ripped this 12 months and I feel there’s nonetheless room on a valuation foundation, plus it’s good diversification. However the core is straightforward: broad market index funds, low charges, maintain without end.

12% crypto.

Primarily Bitcoin and Ethereum. Nonetheless consider within the authentic thesis as a non-institutional retailer of worth and a hedge towards authorities financial coverage gone mistaken.

That stated, it’s a little bit unnerving that it’s appearing extra like a threat asset than digital gold recently. Gold was up 70%+ during the last 12 months. Bitcoin hasn’t stored tempo, which is unusual for one thing that’s purported to be “digital gold.”

However I like the basics long-term, I’ve some good points I don’t wish to take the tax hit on, and it’s a significant diversification play as an anti-institutional hedge. The extra establishments purchase it and the larger it will get, the decrease the upside and extra volatility—however I’m nonetheless holding.

11% actual property.

One rental property. Actually not an awesome pure funding—extra a home we love that we’re renting out till we determine what to do with it.

Organising and working an Airbnb for the previous 4 months has given me a brand new appreciation for the way a lot work short-term leases are, even with another person managing it. It’s additionally made me respect what a superb deal Airbnb is as a traveler—stroll in, use it for a couple of days, pay, and depart with out coping with any of the complications.

9% money.

I like having a cushion, particularly with markets at all-time highs. Half of that is earmarked for a “large bets” fund—ready for one or two high-conviction alternatives the place I can wager meaningfully. In search of these in 2026.

Lower than 1% non-public investments.

Three small bets on founders I consider in: IntelliGems, Postpilot, and Kanpai Meals. All three have constructed nice firms.

I haven’t put a ton of cash to work on the non-public facet. It’s fascinating when you will have area experience and get alternatives with individuals you belief, however it’s a small a part of the general portfolio.

Two Sells This Yr

Tesla. I held Tesla for about 4 years. Good run. However I bought this 12 months for a couple of causes.

My authentic thesis was the product—the automobile was so good and other people had been so pleased with it. However the firm appears to be shifting from being a automobile firm to a giant wager on robotics, self-driving, and automatic taxis. Not that these gained’t work, however my authentic thesis has modified and I haven’t achieved the homework to guage if these different issues are value a trillion-plus valuation.

There’s additionally growing key man threat with Elon. He’s getting older, has labored insanely laborious his complete life, and is spreading himself throughout a number of firms. That threat grows yearly.

At a trillion-plus valuation with my authentic thesis modified, felt like a superb time to exit.

Airbnb. This was considered one of my worst selections just lately. I made a knee-jerk funding—heard it advisable by somebody and purchased it as a result of I wasn’t certain what else to do with the cash. Traditional mistake.

I held it for six to 12 months, broke roughly even, and bought. After organising my very own Airbnb this 12 months, I noticed I’m not as bullish on the corporate as I believed. They’re not horrible, however they’ve been lackluster in development for years and I’m undecided what the catalyst for change is.

The largest lesson: don’t make 5-out-of-10 conviction bets on particular person shares. In case you don’t have excessive conviction, simply put it in an index fund.

That’s the Baseline

I’ll report again on the finish of the 12 months on how this carried out vs. the S&P.

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