“Your tax return looks good!” said my CPA, right before I wrote a $120,000 check to the IRS. Something wasn’t adding up.

Let me be clear: I’ve worked with some brilliant CPAs. I’ve also worked with some who were just… CPAs. The difference? Mindset, not intelligence.

The Compliance vs. Strategy Gap

Most CPAs are trained in compliance:

• File accurate returns
• Avoid audits
• Document everything
• Stay current on tax code changes

These are crucial skills. But they’re not related to strategy.

Strategy requires:

• Proactive planning (not reactive filing)
• Understanding alternative investments
• Coordinating with multiple advisors
• Thinking months or years ahead
• Comfort with sophisticated structures

Why Most CPAs Don’t Discuss Alternatives

After working with over a dozen accounting professionals, here’s what I learned:

Reason #1: They Don’t Know About Them

Alternative investments aren’t in the CPA curriculum. Oil and gas working interests? Cost segregation? Opportunity zones? Many accountants have heard of them but never implemented them for clients.

Reason #2: They’re Liability-Averse

CPAs face liability for bad advice. Recommending unfamiliar strategies increases risk. It’s safer to stick with the “max out your 401(k)” playbook than suggest something that requires specialized knowledge.

Reason #3: It’s Not Their Business Model

Most CPAs charge $2-5K for tax preparation. Proactive strategy requires significantly more time, expertise, and coordination. Unless they’ve built a practice around high-net-worth planning, the economics don’t work.

Reason #4: They’re Historians, Not Architects

CPAs report what happened. Tax strategists design what will happen. Both are valuable—they’re just different roles.

The Red Flags I Missed

Looking back, there were signs my “CPA handled it” approach wasn’t working:

• Only talked to my CPA during tax season
• No conversation about alternative investments
• Strategy sessions were 20 minutes on Zoom
• Never asked about my broader financial goals
• Advice was reactive: “Here’s what you owe”

What Good Tax Strategy Looks Like

After finally finding the right team, here’s what changed:

• Quarterly planning calls (not just annual filing)
• Multi-year tax projections modeling different scenarios
• Coordination between CPA, financial advisor, and investment team
• Proactive identification of opportunities (capital gains harvesting, timing income, etc.)
• Alternative investment evaluation specific to my situation
• Clear documentation and rationale for every strategy

The Alternative Investment Education Gap

Here’s what I wish someone had explained years ago:

Alternatives aren’t “risky fringe investments.” They’re asset classes used by institutional investors, family offices, and high-net-worth individuals for decades.

Common alternatives with tax benefits:

• Real estate (depreciation, 1031 exchanges, opportunity zones)
• Oil & gas (intangible drilling costs, depletion)
• Private equity (carried interest, long-term capital gains)
• Private credit (consistent income, depreciation on direct lending)
• Qualified Small Business Stock (Section 1202 exclusion)

Why they’re not mainstream:

• Minimum investment requirements ($25K-$100K+)
• Accredited investor requirements
• Longer lockup periods
• Complex tax reporting
• Less liquidity than stocks

Why they matter for W2 earners paying $100K+ in taxes:

• Tax advantages offset high W2 income
• Diversification from equity-heavy portfolios
• Potential for superior risk-adjusted returns
• Passive income generation
• Wealth preservation strategies

Making the Shift: The ClairFi Solution

Here’s how we at ClairFi help you make the “transition”.

ClairFi makes alternative investments accessible, understandable, and manageable for busy W2 professionals. This solution streamlines the steps we take:

Step 1: Build the Right Team

The Virtual Family Office team at ClairFi helps you build the right team from our network of tax strategists, investment advisors, insurance specialists and asset protection attorneys. Together we create a coordinated Tax Optimization, Investment, and Asset Protection strategy.

Step 2: Educate yourself

to learn enough to ask smart questions. ClairFi helps you educate yourself about these white-hat tax strategies, which help you manage it all yourself.

Step 3: Start Small

Don’t commit $500K to alternatives on day one. Make smaller investments, Learn how they work, build confidence. ClairFi platform lets you start on Alternates investments with an entry commitment as low as $25,000.

Step 4: Measure Results

The ClairFi way of investing helps you compound the growth from the savings you were missing out on. Track your returns, tax savings, diversification and overall wealth trajectory in a simple single place.