Key Financial Strategies Every 1099 CRE Executive Should Understand

If you’re like many commercial real estate executives we meet, being a “business owner” isn’t how you’d describe your work. You’re part of a major firm, managing clients, and pushing revenue—not sitting around thinking about entity structures or tax strategy. But for the many CRE executives who are paid as 1099 contractors, that’s effectively what you are. And with that role comes access to planning strategies and tax opportunities most W-2 earners don’t have available.

When you’re deep in production mode, it’s easy to overlook just how much control you have. You can structure income intentionally, build tax-efficient retirement plans, diversify concentrated stock positions, involve family members in the business, and shape long-term wealth using the same tools entrepreneurs rely on every day. At the same time, compensation packages continue to evolve, tax rules shift, and your income may rise or fall based on market activity. All of that adds complexity to your financial life, especially if you’re trying to gain more flexibility and create clarity around the future.

Consider what we did for one of our long-term clients, Tom, a 41-year-old CRE executive with dreams of early retirement. Tom and his wife, Jill (not their real names), came to us wanting more financial flexibility, better tax efficiency, and a portfolio that could support their lifestyle long before age 60. They weren’t looking for quick fixes. They wanted a coordinated approach that aligned taxes, retirement structures, private investments, and risk management with their bigger goals.

We helped them diversify well beyond traditional markets, set up the right retirement structures, coordinate taxes with their CPA, evaluate stock compensation, and build a family-centered insurance plan. Today, Tom is on track to slow down in his early 50s and retire by 60, with clarity, confidence, and a plan built around his family’s future. You can read their full story here. [1]

Structure Your Career Like a Business

When I sit down with commercial real estate executives, I often ask a simple question: if you weren’t tied to a big national brand, how would you design your career and cash flow? Most people pause because they’ve been so focused on deal volume and production that they haven’t had space to think like a business owner, even though, as a 1099 contractor, that’s exactly what they are.

Once you see yourself that way, the entire landscape of your financial world changes. The key is building a structure that supports both the income you earn today and the long-term freedom you want tomorrow.

The most successful CRE professionals begin with the destination in mind. Rather than just chasing this year’s bonus, they’re building a structure that supports financial flexibility and the option to slow down or step away when they’re ready.

For many high earners, that starts with forming an LLC and electing S-corp status, which allows them to pay themselves a reasonable salary, take distributions more tax-efficiently, and build a retirement plan that grows alongside their business. If you’re earning well into the six figures, staying in default status can mean paying more self-employment tax than necessary and missing out on powerful planning tools. [2]

In other words, your tax and business structure shouldn’t just keep you compliant. It should support your vision, protect your time, and turn strong earning years into long-term wealth. This is also where thoughtful financial planning becomes essential.

At Envision, I help CRE executives create clarity out of complexity by coordinating cash flow, retirement plans, insurance needs, advanced tax strategy, equity compensation, and long-term investments so every part of your financial life works together with purpose. Whether you need structure during volatile revenue years, guidance on liquidating or converting stock units, or a more diversified investment plan beyond traditional stock-and-bond mixes, I see my role as your financial quarterback.

You can learn more about the full scope of what we offer CRE professionals on our services page, but the heart of it is simple: when you treat your career like a business, you unlock a level of financial creativity and control that can transform both your work and your life.

Make Sense of Your Stock Compensation

Many commercial real estate executives receive some form of equity compensation—stock options, restricted stock units, or direct stock grants—especially when they’re working closely with leadership or contributing to large, strategic projects. While these plans are common for salaried executives, SHRM notes that companies also extend stock-based pay to independent contractors, which includes many high-earning CRE professionals. It’s often used as both an incentive and a retention tool, tying a meaningful portion of your compensation to long-term company performance. [3]

But equity comes with complexity. Vesting schedules, valuations, exercise windows, and tax timing can all dramatically affect what your shares are actually worth. Concentration risk is another major issue, especially when your income, bonuses, and benefits are already tied to the same company.

This is where strategic planning matters. In my role, I analyze stock awards, map out the most tax-efficient time to convert or liquidate them, and help clients diversify without disrupting their career or your cash flow. Equity should fuel your long-term goals, not become an accidental source of risk.

Build Your Own Retirement Plan

One of the biggest advantages of being a business owner is that you’re not limited to the retirement plan your parent corporation offers. You can design your own.

A Solo 401(k), for example, gives you the ability to contribute as both the employee and the employer, allowing for significantly higher annual savings than a traditional plan. Even better, you can add features like after-tax contributions and in-plan Roth conversions, opening the door to a powerful strategy known as the “mega backdoor Roth,” which creates long-term tax-free growth. [4,5]

Because you own the business, you can also make matching contributions from the company side to reduce taxable income. And if you add your spouse as an employee, you can structure these benefits for them, too.

For high-earning commercial real estate executives, a traditional 401(k) may not offer enough room to save at the level your income allows, especially if you want to retire early or catch up quickly. A cash balance plan can help bridge that gap. As a type of employer-sponsored pension, it allows significantly larger, tax-deferred contributions, with limits based on your age, income, and target retirement balance. [6]

These plans do require minimum annual contributions and actuarial oversight, and the employer bears the investment risk. Still, for the right CRE executive, the benefits are substantial: major tax deductions, faster retirement savings, and the ability to pair a cash balance plan with your Solo 401(k) for maximum efficiency.

For CRE executives who want to retire early or build more flexibility into their later career years, these tools can be game-changers.

Maximize the 20% QBI Deduction

One of the biggest and most overlooked advantages commercial real estate executives have as business owners is access to the Qualified Business Income (QBI) deduction. Created under Section 199A, this deduction allows eligible business owners to deduct up to 20% of their qualified business income, which can translate into thousands of dollars in annual tax savings. [7]

Here’s why it matters for you: CRE executives are not considered a “specified service business,” which means the QBI deduction isn’t subject to the same income phaseouts faced by doctors, attorneys, and other service-based professionals. In plain terms, you can often take the full deduction as long as your business is structured correctly.

QBI includes the net income from your LLC or S-corp after deductions for items like self-employed health insurance, retirement plan contributions, and half of your self-employment tax. It doesn’t include wages you pay yourself as an S-corp salary, capital gains, guaranteed payments, or investment income.

Because the calculation depends on how much you pay yourself in W-2 wages versus how much flows through as business profit, structuring your salary and distributions thoughtfully is essential. Too high a salary, and you reduce your QBI; too low, and you risk IRS scrutiny.

This is an area where personalized planning really makes a difference. Optimizing QBI can materially reduce your taxable income every single year.

Start Estate Planning Before Your Wealth Outgrows Your Strategy

For many commercial real estate executives, wealth can grow more quickly than in other careers. Business income, private investments, equity compensation, and real estate holdings can add up in your favor. So, as your estate expands, it’s important to think ahead.

Once you approach estate tax thresholds, strategies like irrevocable trusts, lifetime gifting, and asset protection structures can help reduce future taxes and preserve more wealth for your family.

Remember, estate planning should integrate with your broader goals. Moving appreciating assets out of your estate early can limit future tax exposure, while donor-advised funds (DAFs) or charitable trusts allow you to support meaningful causes in a tax-efficient way.

Blend Charitable Planning with Smart Tax Strategy

In your line of work, income and cash flow rarely arrive in a straight line. Big commissions, bonuses, and liquidity events can create “spike years” that push you into higher tax brackets. That’s why charitable planning and tax strategy often work best together, not separately.

In strong earning years, DAFs let you make a large, tax-deductible gift now while spreading donations to charities over time. If you hold highly appreciated stock or other assets, charitable remainder trusts (CRTs) can help you reduce capital gains, create an income stream for you or your family, and support causes you care about. [8]

On the tax side, we would look closely at how and when your income shows up. Some years it may make sense to accelerate income to use lower brackets or complete Roth conversions; in others, you might defer income, bunch deductions, or increase pre-tax retirement contributions. The goal is to use your variable income to your advantage instead of being surprised by it.

When we integrate charitable tools with year-by-year tax planning, you can lower your lifetime tax bill, support the organizations and communities that matter most, and turn volatile income into a more intentional, values-driven plan.

Choose a Financial Advisor Experienced in CRE Wealth-Building Strategies

Building wealth as a commercial real estate executive takes skill, timing, and consistency. But preserving and growing that wealth while structuring it for long-term stability, tax efficiency, and generational benefit requires a different level of expertise.

High earners face unique challenges, such as variable income, concentrated stock positions, complex tax considerations, and the responsibility of supporting a family today while shaping a legacy for tomorrow. That’s why it’s critical to choose an advisor who can understand complex portfolios, think generationally, coordinate with your tax and estate teams, and design strategies specifically for high-net-worth business owners. [10]

I started this firm to help high earners in your shoes create customized, integrated plans that turn complexity into clarity, from cash flow and retirement modeling to coordinated tax, estate, and investment strategies. You can see how our comprehensive process works in this sample financial plan.

If you’re ready for a plan built around your life, your goals, and your future, I’d love to talk. Let’s build the strategy that supports your goals.

Sources:

Sean Gerlin, CFP®, CPWA®, ChFC®, CLU®, is the Founder and Principal of Envision Wealth Planners, a fee-only financial advisory firm based in the greater Orlando area. Sean specializes in helping high-income families, business owners, and commercial real estate executives align their wealth with their values through a comprehensive Financial Life Planning approach. Learn more about them at envisionplanners.com.

This material has been edited with the assistance of artificial intelligence tools. The information presented is based on sources believed to be reliable and accurate at the time of publication. This material is for educational purposes only and does not necessarily reflect the views of the author, presenter, or affiliated organizations. It should not be construed as investment, tax, legal, or other professional advice. Always consult a qualified professional regarding your specific situation before making any decisions.