My 2026 Portfolio CEO Review: What I'm Changing, Simplifying, and Building

Inside my $8M portfolio review for 2026

👋 Managing Tech Millions 📈 your go-to source for building wealth with tech equity and managing the money that comes with it.

Every Thursday, we'll deliver a concise and powerful lesson on building wealth working for equity compensation or on managing your seven and eight-figure portfolio.

Today, in 5 minutes or less, you’ll learn:

• 💼 The three-part framework I use every year to review my portfolio

• 📊 The specific moves I’m making in 2026 (and why)

• 🏠 How I’m involving my family in wealth management—and why you should too

Hey Portfolio CEOs,

Happy New Year!

A few years ago, I made the transition from money maker to money manager.

No more W-2. No more equity comp cycles. No more golden handcuffs.

Now my full-time work is running my family’s wealth like a business. Building what I call a Micro Family Office.

And every January, I do what any CEO would do: I run an annual review.

Today, I’m sharing exactly what that looks like—inside my $8M portfolio.

Not theory. Not a framework I teach but don’t use. The actual decisions I’m making for 2026.

My hope is that this gives you a model for how to think about your own portfolio as we start the new year.

Managing Tech Millions is a Weekly Podcast that gives you deep dive conversations into building and growing wealth with myself and other industry experts.

This week, I gave more detailed strategies of how to turn panic into purpose during a down market.

• Half the Portfolio, Twice the Freedom: Why net worth isn’t the whole story

• What Ultra-Wealthy Families Know (That Your Advisor Won’t Tell You)

• Never Sell Assets to Fund Your Life: The income-first approach

• Retire in a Bad Year? The math that determines everything

• The Micro Family Office: Family office principles at the $1M-$30M level

The Annual Portfolio CEO Review

When I first started managing serious wealth, I made every mistake in the book.

Too much wealth concentrated in company stock. Chasing hot deals. Zero systems. Lots of FOMO investing.

The turning point was coming to grips with a hard truth: I was brilliant at my day job, but a rookie at managing my millions.

So I did what any systems-minded person would do. I built a framework.

Now, every year, I run what I call an Annual Portfolio CEO Review looking at three areas:

1. Portfolio — Where do I divest and where do I invest?

2. Operations — What can I simplify and make more efficient?

3. Succession — How do I better prepare my portfolio to be passed down?

This takes a few focused sessions each year, but the clarity it creates lasts 365 days.

Every decision runs through my Investment Thesis—my North Star that documents what I’m optimizing for and how I define success.

Let me show you what this looks like in practice for 2026.

---

Part 1: Portfolio Moves

This year, my focus is clear: reduce risk, increase liquidity, and diversify income.

I’m not chasing 20% returns. I’m building a portfolio that can weather any storm while still compounding.

Move 1: Closing Out Underperformers

I’m exiting several private equity and real estate positions where operators aren’t hitting projections, cash flow is unpredictable, and capital is locked up with no clear exit.

This isn’t panic selling. It’s honest evaluation.

If an investment isn’t meeting my thesis, I redeploy that capital somewhere more productive. Simple as that.

Move 2: Doubling Down on Proven Operators

I’m increasing allocation to private equity operators who’ve consistently delivered—hitting distribution targets quarter after quarter.

If you haven’t done any deals in the private markets before, here’s a tip: the operator matters more than the deal.

Move 3: Increasing Public Market Exposure

I’m rotating capital into covered call ETFs, dividend ETFs, and individual dividend stocks.

Three reasons:

• Liquidity — I can exit quickly if needed

• Income diversification — I shouldn’t rely solely on private distributions

• Simplicity — Less operational overhead than private investments

This doesn’t mean I’m abandoning private markets. It means my priority order has shifted:

1. Reduce risk through diversification

2. Increase liquidity

3. Protect and diversify income

4. Pursue strategic growth

This isn’t playing defense. It’s building a portfolio that compounds wealth while managing risk intelligently.

---

Part 2: Operations Simplification

Here’s what nobody tells you: complexity accumulates fast.

You open accounts everywhere, sign up for every tool, and suddenly you’re spending hours managing infrastructure instead of making investment decisions.

I’m no exception. Here’s my 2026 simplification plan:

Consolidation

I’m moving from multiple brokerage accounts to one primary platform with Interactive Brokers. Fewer accounts, fewer providers, easier to manage.

Tool Audit

Every subscription gets reviewed annually. I ask one simple question: Is this tool earning its place?

If I’m not using it monthly or it’s not providing clear value, it’s gone.

The Goal

Spend less time on operations so I can spend more time on actual investing—evaluating deals, building operator relationships, and making strategic decisions.

Think of it like refactoring code. Same functionality, cleaner architecture.

---

Part 3: Succession Planning

This is what most people ignore until it’s too late.

But here’s the reality: if you don’t actively involve your family, they’ll inherit wealth they don’t know how to manage.

Here are my 2026 succession initiatives:

Track 1: Charitable Giving

My sons are selecting our family charity this year. They’ll research options, narrow to three, and present their choice.

This teaches due diligence and stewardship without risking portfolio capital. And they absolutely love it.

Track 2: Investment Training

This past fall, I started getting my oldest son involved in our options portfolio. He’s tracking positions, understanding our covered call strategy, and will execute trades under supervision at some point in 2026.

I’m also thinking about which son conceptually “owns” which part of the portfolio long-term, so they develop expertise in specific areas.

Track 3: Family Governance

I’m ramping up our family board meetings. This quarter, my oldest is presenting on the options portfolio—what we’re producing and the value it’s creating.

The goal isn’t turning my kids into portfolio managers. It’s ensuring they understand wealth is a responsibility, not just an inheritance.

Three Lessons from This Year

Lesson 1: Your priorities will shift—and that’s wisdom, not weakness.

I went from 100% growth-focused in 2012, to income-focused in 2021, to risk-reduction focused moving into 2026.

Your Investment Thesis should evolve as your life evolves.

Lesson 2: Simple beats complex every time.

Lesson 3: Family involvement compounds like interest.

Start early. Do it often. I began bringing my sons into financial discussions in middle school. That early exposure is already paying dividends in how they think about money.

---

Your Turn: The Three Questions

Here’s your action plan for January.

Block time on your calendar this week and ask yourself these three questions:

Question 1: Portfolio — Where do I divest and invest?

Pull up your allocation. Be honest about what’s working and what’s not. Filter every decision through your Investment Thesis.

And if you don’t have an Investment Thesis yet... keep reading.

Question 2: Operations — What can I simplify?

Tally up your accounts, subscriptions, and tools. What’s earning its place? Consolidation isn’t about being cheap—it’s about being effective.

Question 3: Succession — How do I future-proof my portfolio?

Here’s the uncomfortable question: If something happened to you tomorrow, could your family take over?

Do they know where the accounts are? Who the advisors are? How the investments work?

Start documenting everything—your Investment Thesis, account access, key contacts, and the why behind your decisions. Then gradually bring your family into the conversation so wealth transfer doesn’t become a crisis moment.

---

New Year. New System.

Look, I’m not going to pretend this is easy.

Running your wealth like a business takes time, energy, and commitment. It’s real work.

But here’s what I know after making the transition myself:

The alternative is worse.

Random investments. Scattered accounts. Family unprepared. Anxiety despite having millions.

That’s not wealth. That’s a collection of assets with no system.

If you’re ready to change that in 2026, I want to help.

It’s the new year. Make the move.

Here’s to running your wealth like a business in 2026.

Christopher

Join me for The WealthOps Way—our free live masterclass designed to help you stop guessing and start running your wealth like a business.

You’ll go from scattered to strategic as you craft your own Portfolio Thesis—the foundation of everything that follows.

• Clarify your long-term vision

• Define your next best investment move

• Build the system that turns wealth into freedom

Spots are limited—and the clarity you’ll gain? Game-changing.

Let’s build your portfolio like it’s your next great company!

If you like the newsletter, support us by letting us know what you think (one click); please do that now!

PS...If you're enjoying Managing Tech Millions, please consider referring this edition to a friend.

And whenever you are ready, there three ways I can help you:

• Follow me on LinkedIn: Get more insights and real-time updates.

• Tune into the Podcast: Dive deeper into wealth strategies and interviews.

• Get in Touch: Ready for a bigger move? Let’s talk.

Disclaimer: This newsletter is for informational purposes only and does not constitute financial or career advice. Always consult with qualified professionals before making any decisions based on the information provided.