Why your $5M portfolio feels like a side project (and what to do about it)

Inside the knowledge gap that's costing first-generation wealth builders millions

👋 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:

• 💼 Why traditional financial services aren’t built for $1M–$30M portfolios

• ⚙️ The operating cadence and team architecture your wealth actually needs

• 🚀 How to escape the “service desert” and build your own Micro Family Office

Hey Portfolio CEOs,

You’re standing in a desert.

Not the kind with sand and cacti. The kind where you’ve got $5 million in assets, and the financial services industry has absolutely nothing built for you.

Too small for the family office world (they start caring at $100M+). Too sophisticated for the robo-advisor crowd (set it and forget it doesn’t cut it anymore). Too busy to DIY everything (you’ve got a career, a family, a life).

Welcome to the service desert. Population: every first-generation wealth builder between $1M and $30M.

It took me 5-7 years to figure this out. I kept thinking I was missing something—that there had to be a product, a service, a solution designed for someone exactly like me.

There wasn’t. There isn’t.

And nobody tells you this up front.

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’m revealing how I turned my portfolio from zero cash flow into $200K a year in income—without selling assets or touching principal.

• The 60/40 Problem: Why traditional advisors keep you stuck chasing growth until retirement

• The $100M Secret: How the ultra-wealthy generate income while their wealth keeps growing

• My Turning Point: The shift from 98% stocks to a portfolio that pays me every month

• The Evergreen Portfolio: A 3-step framework to create income today and build lasting wealth

• Freedom Now, Not Someday: How to make your portfolio work for you—not the other way around

The Data That Changes Everything

We recently surveyed hundreds of tech professionals who’ve crossed the multi-million-dollar threshold. The results were stunning—not because they were surprising, but because they were so damn consistent.

82 people cited “lack of knowledge or experience” as their biggest barrier to wealth management.

• Not equity compensation confusion (38 responses).

• Not tax optimization (24 responses).

• Not “which stocks to pick” or “how to time the market.”

Knowledge. Experience. Education.

The gap between where you are and where you want to be isn’t tactical—it’s foundational. And here’s what nobody’s telling you: that gap exists by design.

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Why Your Portfolio Feels Like a Side Project

Think about how you built your career. You approached career development with systematic rigor:

• Clear role strategy

• Defined success metrics

• Regular sprint planning

• Cross-functional teams

• Post-mortems and iteration

Now think about your portfolio. Your $3M, $5M, $10M portfolio.

Be honest: are you running it like a business, or treating it like a hobby?

For most tech professionals I talk to, wealth management looks like this:

• Check Vanguard when you remember to

• Panic-Google “what to do with RSUs” the week before they vest

• Have a CPA who does your taxes but doesn’t strategize with you

• Maybe read some Reddit threads about index funds

• Hope it all works out

You wouldn’t run a $10M/year department this way. But you’re running a multi-million dollar portfolio this way.

Why?

Because nobody ever taught you the alternative.

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The Three Knowledge Gaps Costing You the Most

Gap #1: You Don’t Have an Investment Thesis

The mistake: You’re making portfolio decisions reactively instead of strategically.

Someone at work mentions Bitcoin, so you buy some. Your brother-in-law is crushing it in real estate, so you look at a syndication deal. A Reddit thread convinces you index funds are the only way. Each decision happens in isolation.

What this costs you: Scattered assets. No coherence. Decision paralysis when the next “opportunity” appears.

The business parallel: Like building features without product strategy. Every shiny object becomes a priority.

The fix: Write your one-page investment thesis this week. Answer these questions:

• What am I building this wealth for? (Specifics, not “financial freedom”)

• What’s my risk tolerance based on my actual situation, not my feelings?

• What asset allocation reflects my goals and timeline?

• What won’t I invest in, and why?

This isn’t complicated. But without it, every financial decision is a guess.

Gap #2: You Don’t Have an Operating Cadence

The mistake: You check your portfolio when you “remember to” instead of systematically.

Most tech professionals I work with review their portfolios 2-3 times per year. Usually after something dramatic happens in the market. This is purely reactive management.

What this costs you: Missed rebalancing opportunities. Tax inefficiency. Drift from your goals. That sick feeling when you realize you should have done something six months ago.

The business parallel: Running a company without quarterly business reviews. Flying blind until there’s a crisis.

The fix: Set up your wealth management operating system:

• Monthly: Review transactions, check for anomalies, update net worth tracking

• Quarterly: Portfolio rebalancing, tax planning check-ins, assess vs. goals

• Annually: Deep strategy review, update investment thesis, succession planning

Put these on your calendar like board meetings. Because that’s what they are.

Gap #3: You Don’t Have Team Architecture

The mistake: You’re either trying to DIY everything or you’ve blindly outsourced everything to “advisors” who may or may not have your interests aligned.

Here’s the truth about wealth management at your level: you need a team. But not the team the industry wants to sell you.

What this costs you: Either burnout from doing it all yourself, or abdication to people who earn commissions on your confusion. Neither path builds generational wealth.

The business parallel: Like being a solo founder forever, or hiring all the wrong roles because you didn’t define the org chart first.

The fix: Map your wealth management org chart. Even if every role is currently empty or filled by you, you need to know:

• Who handles tax strategy? (Not just tax filing—strategy)

• Who manages investment execution?

• Who coordinates everything?

• Who provides education and frameworks?

• Who handles legal/estate work?

You’re not looking for a single “advisor” who does everything poorly. You’re building a team of specialists who do specific things excellently.

What Nobody Tells You About the $1M-$30M Range

Here’s what I wish someone had told me when I first crossed seven figures:

You’re in a service desert, and nobody’s coming to save you.

The financial services industry isn’t built for you:

• Robo-advisors are built for people with $100K-$500K who need simplicity

• Wealth managers are built for people with $1M-$5M who need basic portfolio management

• Family offices are built for people with $100M+ who need everything

You? You need sophisticated wealth management—private equity access, tax optimization, estate planning, systematic operations—but you don’t have $100M to justify building a full infrastructure.

So you’re stuck in the gap. The service desert.

The uncomfortable truth: If you want to grow your wealth from $5M to $20M, from $20M to $50M—you have to figure this out yourself.

Not because you’re bad at delegating. Not because you’re a control freak.

Because there is no product built for you.

The Mindset Shift That Changes Everything

Stop asking: “What should I invest in?”

Start asking: “How should I operate my portfolio?”

This isn’t semantic. It’s fundamental.

When you ask “what should I invest in,” you’re looking for tips. Hot stocks. The next big thing. Someone else’s answer.

When you ask “how should I operate my portfolio,” you’re building a system. A repeatable process. Your own answer.

Try this 3-question filter for any wealth decision:

1. Would I run a $5M business this way?

2. What’s my systematic process for this decision?

3. Where’s my documentation/tracking for this?

If your answers are “no,” “I don’t have one,” and “nowhere”—you’ve found your knowledge gap.

You’re Not Alone in This

The data proves it. 82 responses saying “lack of knowledge” as the #1 barrier. 62 saying “lack of time.” 57 saying “fear of making expensive mistakes.”

These aren’t individual problems. This is a systemic gap in how first-generation wealth builders learn to manage significant wealth.

You’re not bad at this. You were never taught this. And the industry that should be teaching you is too busy selling you products that don’t fit.

But here’s the good news: the skills you used to build your career—systematic thinking, framework development, team building, iterative improvement—those same skills work for wealth management.

You just need to apply them.

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Your Turn

Here’s what I want to know:

What’s the ONE wealth management question you wish someone would answer honestly?

Not the question you think you should ask. The question that keeps you up at night. The one that feels “too basic” or “too complicated” to admit you don’t know.

Drop it in the comments. Because I guarantee: if you’re wondering about it, hundreds of other tech professionals are too.

And that’s how we get out of the desert. Together.

Here’s to building your Micro Family Office,

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.

👉 In just one session, you’ll:

• Clarify your long-term vision

• Define your next best investment move

• Build the system that turns wealth into freedom

Choose your class:

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

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

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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.