What Portfolio CEOs Look for in Advisors

How to identify advisors with aligned incentives who think broadly and educate deeply

👋 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 6 questions that reveal whether an advisor’s incentives align with yours

• 💡 How to identify advisors who think beyond stocks and bonds

• 🗺️ Why education mindset matters more than credentials

Hey Portfolio CEOs,

Last week I told you about my Morgan Stanley meeting—the one where I realized traditional advisors couldn’t help me at my wealth level. (If you missed it, read about the service desert here)

But here’s what I didn’t say: Great financial advisors exist.

Some people email me assuming WealthOps is anti-advisor. We’re not. We’re anti-misaligned incentives. Anti-narrow thinking. Anti-dependency over education.

There are advisors out there who have incentives aligned with your goals, think broadly across all investment types, and want to educate you—not keep you dependent.

The question isn’t “Should I work with an advisor?”

The question is: “How do I identify one who will empower me instead of limit me?”

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 breaking down the real difference between the average millionaire and the top 1%—and why wealth doesn’t just grow, it transforms.

• The Net Worth Divide: The true financial thresholds for the top 10%, 5%, and 1%

• Investable vs. Total Net Worth: Why what you can actually invest matters more than just the total number

• The Shift to Ownership: How the top 1% focus on ownership capital, not dependent assets

• The Wealth Percentile Trap: Why most millionaires plateau before reaching the next level

• The Great Decoupling: How your wealth needs to evolve from accumulation to architecture

Most People Ask the Wrong Question

When vetting advisors, most people ask: “What are your credentials?”

CFP. CFA. Series 7. AUM under management. Years of experience.

Those credentials matter. But they don’t tell you the most important things:

• Are their incentives aligned with helping you reach your goals?

• Do they educate themselves broadly, or just stick to what they already know?

• Do they want to teach you, or keep you dependent?

That Morgan Stanley meeting? The advisors were credentialed. Experienced. Polished.

But their incentives were misaligned. Their thinking was narrow. And they had zero interest in educating me.

The questions below help you identify advisors who get it.

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Question 1: How Are You Compensated—and How Does That Align With My Goals?

Why it matters: If helping you reach your goals means less revenue for them, their incentives aren’t aligned with yours.

What to ask:

• “How are you compensated—and does that align with my goals?”

• “For long-term buy-and-hold positions, how do we negotiate compensation that reflects the actual work?”

• “What specifically are you compensated on? Assets under management? Trades? Products?”

The nuance most people miss:

AUM-based compensation isn’t inherently bad. It’s a way to pay for ongoing portfolio management and advice.

But you need to understand the incentive structure:

If you’re building a long-term, buy-and-hold portfolio that requires minimal trading, why are you paying 1% annually as if they’re actively managing it every day?

If they’re spending 2 hours a year reviewing your static portfolio, negotiate fees that reflect that reality—not fees designed for active management.

Misalignment to watch for:

• Moving money into private investments they can’t manage = their revenue decreases

• Entity structures they can’t access = their AUM shrinks

• Tax strategies that move money out of managed accounts = less compensation

That’s not malicious. It’s structural. But you need to know it exists.

Green flags:

• Transparent about all compensation upfront

• Willing to negotiate based on strategy (passive vs. active management)

• Comfortable discussing incentive alignment openly

• Modular pricing (you pay for what you actually use)

Red flags:

• Dismissive of alternatives because “they’re too risky” (translation: can’t earn fees on them)

• Push to consolidate everything under their management

• Resistance to entity structures or strategies outside their revenue model

The test: Ask them directly: “If my goals mean moving some assets into private deals you can’t manage, how do you feel about that?”

Their answer tells you everything.

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Question 2: Do You Educate or Just Execute?

Why it matters: Great advisors want informed clients. Poor advisors want dependent clients.

What to ask:

• “Walk me through your investment philosophy and why you recommend this approach.”

• “What should I understand about how this strategy works?”

• “What resources do you provide to help me learn?”

Red flags:

• “Just trust us”

• Vague explanations without underlying reasoning

• Resistance to questions

• Uncomfortable when you ask “why”

Green flags:

• Clear explanations of their thinking

• They want you to understand the strategy, not just follow it

• They provide educational resources

• They’re excited when you ask intelligent questions

• They view education as part of their service

The shift: When I work with my current advisors, they explain why they recommend something. I learn the framework. I make the decision. They execute.

That’s the dynamic you want. Not “trust me”—but “here’s how this works, here’s why it makes sense for your situation, and here’s how to think about it.”

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Question 3: Do You Think Broadly Across Investment Types?

Why it matters: If your advisor only thinks about stocks and bonds but personally invests in private equity and real estate—that’s a massive red flag.

What to ask:

• “What do you personally invest in?”

• “What percentage of your clients invest in private equity or real estate?”

• “How do you think about alternative investments in a portfolio?”

The hidden hypocrisy to watch for:

I’ve met advisors who sell their clients 60/40 stock-and-bond portfolios while they personally invest in private equity deals, real estate syndications, and income-generating businesses they never mention to clients.

Ask them directly: “What do you personally invest in?”

If the answer is “private equity and real estate” but they’re telling you to stick with public markets—that’s not risk management. That’s keeping you in investments they can earn fees on.

Green flags:

• Invests the same way they advise (ask them directly)

• Experience helping clients access alternatives

• Connections to vetted private deals

• Balanced view: “Alternatives have a place for accredited investors building wealth”

• Willing to coordinate with your direct investments

Red flags:

• Blanket dismissal: “Stick to stocks and bonds—alternatives are too risky”

• Never worked with clients on alternatives (but invests in them personally)

• Defensive when you mention private deals

• Haven’t educated themselves on options outside their fee-earning model

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Question 4: How Do You Integrate Tax Planning?

Why it matters: You want advisors who bring new ideas and keep each other honest—not a single house trying to fit you into their formula.

What to ask:

• “How do you integrate tax planning—especially if I bring my own tax strategist?”

• “Are you comfortable with me having multiple advisors who you’ll coordinate with?”

• “How do you handle clients who bring strategies to the table instead of waiting for recommendations?”

Why multiple advisors matter:

As CEO of your wealth, you want different advisors bringing different ideas. That keeps everyone honest and prevents groupthink.

The biggest risk: Single-house advisory trying to put you into a formula.

Minimum overhead for them. Minimum value for you. Maximum profit for them.

Red flags:

• “We need to manage everything or we can’t help you”

• Resistance to coordinating with other professionals

• Uncomfortable when you bring strategies to the table

• “You should talk to your CPA about that” (translation: not my problem)

Green flags:

• Excited when you bring tax strategies or ideas

• Actively coordinates with your CPA and CTP

• Respects that you’re building a team, not hiring a single solution

• Views themselves as one specialist on your team

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Question 5: Can You Work with My Entity Structure?

Why it matters: If you’re building a Micro Family Office, you’ll have multiple entities. Your advisor needs to understand how money flows between them—or at least respect that you’re operating at that level.

What to ask:

• “Have you worked with clients who have Holding Companies or Management Companies?”

• “Can you manage accounts inside my entities, not just personal accounts?”

• “Do you understand how inter-company transactions work?”

Red flags:

• Confused by entity structures

• “We only work with personal accounts”

• No experience with business entities

• Dismissive of entity-based wealth management

Green flags:

• Experience with entity-based portfolios

• Can manage accounts inside your Holding Company

• Understands how distributions, loans, and transfers work

• Comfortable coordinating with your bookkeeper on entity accounting

• Or at minimum: respects that you’re operating at this level even if it’s outside their scope

The gap: Most retail advisors have never worked with entity structures. They manage personal accounts. That’s fine if you’re just starting out. But if you’re building a MiFO, you need someone who can work within your structure—or who at least understands what you’re building.

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Question 6: Are You Comfortable with Me Being CEO?

Let’s be direct about this.

What to ask:

• “Are you comfortable with me being the CEO of my wealth and having multiple partners you’ll work with?”

• “Can I hold you accountable to my performance metrics—not just broad market returns?”

• “Or do you need to be the CEO?”

Why this matters:

The vision is yours. The strategy is yours. The metrics are yours.

As CEO, you define what success looks like:

• Maximized returns

• Reduced fees and overhead

• Specific income targets

• Risk-adjusted performance

• Tax-efficient execution

Advisors should execute within your strategy and be held accountable to your measures of success—not just “we beat the S&P.”

Their job: Strategic service partner who executes your vision.

Your job: Drive the strategy. Define the metrics. Hold them accountable.

Red flags:

• “We measure success by beating the benchmark” (whose benchmark? Yours or theirs?)

• Uncomfortable when you define custom success metrics

• Need to control the entire portfolio to “do their job”

• Threatened by accountability to your specific goals

• Defensive when you ask about fee efficiency or overhead reduction

Green flags:

• “Tell me what success looks like for you, and I’ll execute against those metrics”

• Excited when you articulate clear performance expectations

• Comfortable being measured on your definition of success

• Views themselves as execution partner accountable to your strategy

• Transparent about fees, overhead, and performance metrics

The dynamic you want:

You’re the CEO. You set the vision. You define success metrics.

They’re specialists who execute and report results against your measures, not theirs.

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What These Questions Reveal

These six questions all point to three underlying issues:

1. Are incentives aligned? If helping you reach your goals means less revenue for them, you have a structural problem. (Questions 1, 6)

2. Do they think broadly? If they only know stocks and bonds and dismiss everything else, they can’t help you build real wealth. (Questions 3, 5)

3. Do they educate? If they want you dependent instead of informed, they’re not empowering you—they’re limiting you. (Questions 2, 4)

Great advisors have aligned incentives. They think broadly across investment types. They educate themselves and their clients. They’re comfortable with informed, strategic clients who orchestrate their own wealth.

That’s who you’re looking for.

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Where Advisors Fit in a MiFO

Here’s how I think about it:

You are the CEO. You set the strategy. You define the investment thesis. You decide what goes where.

Advisors are execution partners. They manage specific portfolios within your strategy. They bring expertise you don’t have. They handle implementation within their domain.

Your CPA and Certified Tax Planner coordinate tax. They optimize around your portfolio decisions.

Your attorney handles legal and estate planning. They structure entities and protect assets.

Everyone has a role. Nobody replaces you as strategist.

That’s the shift. From “I need someone to manage my money” to “I need specialists with aligned incentives who execute within my strategy.”

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Your Action This Week

If you currently work with an advisor, run through these six questions. Do they pass? If not, what’s missing?

If you’re looking for an advisor, use these as your vetting framework. Don’t start with credentials. Start with: “Are incentives aligned? Do they think broadly? Do they educate?”

And if you realize your current advisor has structural limitations—misaligned incentives, narrow thinking, or resistance to education—that’s useful information. It doesn’t mean fire them. It means you know the limitation and can plan around it.

You’re the CEO. Vet your team accordingly.

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— Christopher

P.S. The best advisors I work with today are the ones who were excited when I told them I was building a Micro Family Office. They didn’t see it as a threat. They saw it as a client who knew what they wanted and could articulate strategy clearly. Those are the advisors worth finding.

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Go Deeper

Want to build your Micro Family Office? Join the MiFO Accelerator and learn the frameworks that help you become CEO of your wealth.

Not sure where you stand? Take the Portfolio CEO Self-Assessment and identify your gaps across the 7 MiFO Components.

Subscribe to the newsletter: Get frameworks, systems, and practitioner insights every week → Managing Tech Millions

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