10 Financial Pitfalls Even Top Earners Still Fall Into
Understand what’s holding you back—and how to move forward.
👋 Managing Tech Millions 📈 your go-to source for transitioning from money maker to money manager.
Every Tuesday, we'll deliver a concise and powerful lesson on growing and managing your seven and eight-figure portfolio as a legacy asset.
Our mission is to demystify equity compensation, investment strategies, and financial independence for tech professionals from those who are doing it themselves.
Hello Portfolio CEOs,
Watching financial news right now isn't good for anyone's mental health.
While writing last week's article, I was reminded that during uncertain times, the best way to move forward and maintain perspective is through learning.
During previous financial crises (2008 and 2020), I found success by tuning out the noise and focusing on education.
This approach serves me well now as over the next few weeks, I begin exploring core concepts around Micro Family Offices, WealthOps, Evergreen Portfolios, and Private Equity Foundations.
I promise not to leave you hanging or create unnecessary drama. Instead, I aim to be a calm voice of reason—the CEO of my portfolio—leading by example.
This week, I'll examine the 10 problems that prevent tech employees from establishing a Micro Family Office.
Identifying these obstacles is the first step toward overcoming them.
Let's get to work.
This Week on the Podcast!
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.
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Where High Earners Get Stuck
Here’s what I see all the time:
Tech professionals—engineers, product leads, senior directors, and vice presidents—are absolutely crushing it in their careers.
They’ve built wealth through equity compensation, IPOs, stock grants.
They’ve worked hard, taken smart risks, and made all the right moves to create serious financial upside.
And then… they hit a wall.
Because wealth creation and wealth management are two very different skill sets.
One is about opportunity. The other is about structure.
The result?
You’re left:
Wondering what to do with your concentrated stock position
Drowning in advice from financial influencers and polished advisors
Wasting time on spreadsheets and tools that don’t actually give you clarity
Feeling the quiet anxiety of knowing you “should be doing more,” but not knowing what
Things Were Moving So Fast…
In 2012, I watched my wealth skyrocket… and then nosedive weekly.
I was fresh off a 7-figure IPO, but 90% of my net worth was locked in one stock.Every market swing felt like a gut punch. I was “rich” on paper, but totally exposed. No plan. No team. No clue how to manage it all.
That moment kicked off a 12-year journey—from scattered spreadsheets and second-guessing to building a portfolio that now runs like a business.
Along the way, I learned that earning money and managing wealth are two entirely different skill sets—and no one teaches us the second part.
Through trial, error, and studying how the ultra-wealthy actually operate, I created the WealthOps system to solve the problems I faced—and that I see so many others still stuck in today.
If you’ve been feeling stuck, confused, or overwhelmed—know this: It’s not your fault.
The system wasn’t built to teach you how to manage wealth, especially when equity comp is involved. You’re not alone, and you’re not behind.
You’re exactly where you need to be—right here, with the right tools and the right community.
Through trial, error, and studying how the ultra-wealthy actually operate, I created the WealthOps system to help others get unstuck and build and scale a Micro Family Office.
Let’s break down the 10 biggest traps—and the next steps you can take to move forward. 👇
The 10 Biggest Problems Keeping You Stuck
1. All Vision, No Plan
You know you want to grow and protect your wealth, but you’ve got no clear roadmap to get from here to where you want to go. Too many people know they want financial freedom but are missing the plan to get there.
2. Stuck in the Money-Maker Mindset
You’re crushing it at earning, but no one taught you how to manage wealth like a business. You’re playing the wrong role—operator instead of CEO.
3. Equity Compensation Confusion
Stock options, RSUs, ESPPs—valuable, yes. But without a clear strategy, they’re a messy tangle of risk and lost potential. This leads to analysis paralysis.
4. Overexposed to a Single Asset
Way too much riding on one stock or company. One market move and your net worth swings wildly. You don’t have or know where to build a divestiure plan.
5. Zero Operational Structure
Your portfolio is being run like a side hustle—not like the multi-million dollar business it really is. Without the focus that it needs, it will never give you the outcome you want.
6. No Team, No Cadence, No Accountability
You’re going it alone. No advisors you fully trust. No system of review. No one to push your thinking or help you zoom out. What you are missing is a community of peers to keep you accountable and keep you moving.
7. You Know You’re Missing Opportunities—but You’re Stuck
You can feel the friction. You just don’t know what to change or where to begin. Without a plan, you don’t want to make the wrong move.
8. Time and Energy Drain
Managing wealth feels like another full-time job—one that’s costing you more energy than it’s giving back. Learning sounds exhausting at the end of the day if you don’t know where to start.
9. Decision Paralysis
Too many options. Too much at stake. So you freeze, delay, or second-guess everything. Doing nothing is less risk than making a bad move.
10. No Trusted Source of Truth
Generic advisors. Noisy internet. Conflicting opinions. You’re overloaded with info—but no one’s showing you what works for your situation. How do you find the truth?
It is Time to Get To Work (and Get Honest)
Ready to Get Unstuck?
Here’s the truth:
The fastest way to move forward is to name what’s holding you back.
You just read the biggest wealth challenges high-earning tech pros face—and I guarantee you’re not alone.
During coaching and conversations, I’ve repeatedly seen these same patterns (and lived through most of them myself).
Now it’s your turn.
👉 Take 30 seconds to fill out this quick 3-question multiple-choice survey.
Tell me where you feel friction—Strategy, Structure, or Support.
When you name it, I can help you start solving it.
(or reply with the words “I’m stuck” and I’ll send it to you directly)
No pressure. No judgment. Just a chance to get clarity—and take the first step toward running your wealth like the business it truly is.
Let’s get to work.
Ready to Take More Action?
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 two sessions, 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.
👉 Apply Now [LINK]
Let’s build your portfolio like it’s your next great company.
PS .
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