For many executives, founders, and technology professionals, a concentrated stock position does not result from a single investment decision. It builds gradually through restricted stock units, stock options, employee stock purchase plans, founder shares, or years of holding a successful investment. The financial impact can be life-changing.
SpaceX’s June 2026 initial public offering offers a timely example. Employees and early shareholders who accumulated company equity suddenly faced a different planning question. The challenge was no longer simply how to build wealth. It was how to preserve that wealth when a significant portion of it remained tied to one company.[1]
That is the central tension of a concentrated stock position. The investment may have created tremendous opportunity, but it can also expose an investor to risks that are easy to underestimate while the company is performing well.
If your salary, benefits, future equity compensation, and investment portfolio all depend on the same company, a disappointing earnings report, regulatory change, product failure, or industry shift could affect both your career and your net worth at the same time.
Diversification cannot eliminate investment risk, and selling is not always the only answer. The goal is to build a deliberate concentrated stock diversification strategy that balances risk reduction, capital gains taxes, liquidity, employer restrictions, and continued upside participation.
This guide explains five advanced strategies that may help investors diversify a highly appreciated stock position involving RSUs, ISOs, founder shares, public company stock, or other forms of equity ownership.
What Is a Concentrated Stock Position?
A concentrated stock position exists when one company represents an outsized portion of an investor’s portfolio or total net worth. There is no single percentage that is appropriate for every household. The level of concern depends on the investor’s financial plan, cash flow, other assets, time horizon, tax exposure, risk tolerance, and connection to the company.
Common sources of concentrated stock include:
Restricted stock units, or RSUs
Incentive stock options, or ISOs
Nonqualified stock options
Employee stock purchase plan shares
Founder or early employee shares
Inherited stock
A long-held, highly appreciated investment
Employer stock held inside a retirement plan
The position becomes especially important when the investor also depends on the company for current income and future compensation. In that situation, employment risk and investment risk are closely connected.
Why Investors Delay Diversification
Investors often recognize the risk but still struggle to act. Common reasons include:
A large embedded capital gain
Confidence in the company’s future
Loyalty to an employer or founder
Fear of missing additional appreciation
An emotional attachment to inherited or founder shares
Trading windows, blackout periods, or anti-hedging policies
Uncertainty about how sale proceeds should be reinvested
Concern about making an irreversible decision
Taxes matter, but allowing taxes to control the entire decision can create a different and potentially larger risk. A useful question is:
“If you received the same amount in cash today, would you invest all of it in this one company?”
If the answer is no, continued ownership may deserve a closer review.
Start With the Simpler Concentrated Stock Strategies
Advanced solutions are not always necessary. Before considering a more complex structure, investors should evaluate straightforward strategies such as selling shares immediately, diversifying in stages, identifying specific tax lots, coordinating gains with capital losses, and donating appreciated shares to charity.
For employees receiving new equity awards, selling newly vested RSUs can also prevent the concentrated position from becoming larger. Executives subject to trading restrictions may consider a properly established Rule 10b5-1 trading plan with qualified legal and compliance guidance.[2]
When a large embedded gain, limited liquidity, or a desire for continued ownership makes those approaches insufficient, the following advanced strategies may be worth evaluating.
1. Long-Short Direct Indexing
How the strategy works
Traditional direct indexing allows an investor to own the individual securities that make up an index rather than purchasing a single index fund. Because each security is owned directly, positions that decline may be sold to harvest tax losses.
Long-short direct indexing expands the potential opportunity set. A manager builds a diversified portfolio of long positions while also shorting selected securities. For example, a strategy might hold $1.30 of long positions and $0.30 of short positions for every $1.00 invested.
Tax losses may be generated when:
A security owned in the long portfolio declines and is sold at a loss.
A security sold short rises, creating a loss when the short position is closed.
Those realized losses may help offset capital gains generated by gradually selling appreciated company stock. Capital losses generally offset capital gains first. Subject to applicable tax rules, unused net capital losses may also offset a limited amount of ordinary income and be carried into future tax years.[3]
Investment minimums vary considerably. Many institutional programs are designed for investors with substantial taxable assets outside the concentrated stock position.
Potential advantages
The primary appeal is the potential to accelerate diversification without recognizing the full tax cost of selling a concentrated stock position all at once.
Other possible benefits include:
Broader market exposure
Ongoing liquidity in the diversified portfolio
Customization around existing company and industry exposure
Tax-loss harvesting throughout the year
Coordination with charitable giving, option exercises, and scheduled stock sales
This strategy may be most relevant for an investor who has meaningful liquid assets outside the company stock position and expects to recognize substantial capital gains over several years.
Potential disadvantages and risks
Long-short direct indexing is more complex than traditional tax-loss harvesting. Short selling can involve borrowing costs, dividend-replacement payments, margin requirements, short squeezes, and the possibility that borrowed shares will be recalled. Losses on an individual short position can theoretically continue increasing as the security’s price rises.[4]
Additional considerations include:
Higher management and trading fees
Greater gross market exposure than the investor’s net capital
Tracking error relative to a traditional index
More complicated tax reporting
Wash-sale, straddle, and constructive-sale considerations
No guarantee that harvested losses will exceed fees or investment underperformance
Tax-loss harvesting often defers taxes rather than eliminating them. Replacement investments may carry a lower cost basis, which can create future gains when they are sold.
For the right household, long-short direct indexing may be a useful capital gains planning tool. For the wrong household, it can become an expensive and complicated strategy built around tax benefits that never fully materialize.
2. Zero-Cost Collars
How the strategy works
A zero-cost collar is an options strategy intended to establish a range within which an investor’s company stock value may fluctuate. The investor typically purchases a put option below the current stock price and sells a call option above it.
The put may create a potential floor by giving the investor the right to sell shares at a predetermined price. The premium received from selling the call helps pay for the put. When the premiums are approximately equal, the structure is commonly described as a zero-cost collar.
Suppose an investor owns stock trading at $100 per share. The investor might purchase a put with an $80 strike price and sell a call with a $125 strike price.
At expiration:
If the stock falls substantially, the put may protect value below approximately $80.
If the stock remains between $80 and $125, the investor generally continues participating in the price movement.
If the stock rises above $125, the call limits participation beyond that price.
Potential advantages
A collar may reduce downside exposure without requiring an immediate sale. It may be attractive when the investor:
Believes the stock still has additional upside potential
Wants protection before retirement or a major purchase
Plans to sell later but wants to reduce near-term risk
Would face a significant immediate capital gains tax
Is navigating an approved trading or diversification plan
The premium from the call may also reduce the out-of-pocket cost of purchasing downside protection.
A hedge may also improve the position’s usefulness as collateral. Because the put establishes a defined downside floor, some lenders may assign a higher collateral value or advance rate to hedged shares than to an unhedged concentrated position. That can increase the portion of the position available to support a securities-backed line of credit, or SBLOC, potentially creating additional liquidity without an immediate sale. This treatment is lender- and structure-specific, however, and the lender may still reduce the advance rate, issue a maintenance call, or liquidate collateral if its requirements are not met.[7]
Potential disadvantages and risks
The largest tradeoff is capped upside. The investor exchanges some future appreciation for downside protection.
The phrase zero cost can also be misleading. The transaction may involve bid-ask spreads, commissions, or other embedded costs even when the option premiums offset one another.
Employer restrictions are another major concern. Many public companies prohibit or restrict hedging transactions involving company stock, particularly for executives and insiders.[5]
A collar may also create tax complications. If the structure removes too much of the investor’s economic risk, it could be treated as a constructive sale under applicable tax rules.[6]
Any collar strategy should be coordinated with experienced tax, legal, investment, and compliance professionals.
3. Exchange Funds
How the strategy works
An exchange fund allows multiple investors with highly appreciated concentrated stock positions to contribute their shares into a pooled partnership in exchange for a proportional interest in the fund’s diversified portfolio.
One investor might contribute technology company stock, while others contribute shares of different companies. Because each investor exchanges appreciated stock for a partnership interest rather than cash, the contribution is generally not an immediate taxable sale.[8]
Exchange funds commonly impose or strongly encourage a holding period of approximately seven years. Partnership tax rules can trigger gain when certain contributed property is distributed to another partner, or when a contributing partner receives other property, within seven years. After the fund’s holding period, investors may typically receive a diversified basket of securities rather than cash.[8]
Potential advantages
The central benefit is immediate economic diversification without an immediate taxable event.
Exchange funds may be attractive to investors who:
Own extremely low-basis stock
Do not need near-term liquidity
Want diversification but are reluctant to recognize a large gain
Are comfortable owning a private partnership interest
Have already evaluated simpler strategies such as staged sales and charitable giving
The diversified securities received in the future may also create more flexibility for tax planning, gifting, or charitable strategies.
Potential disadvantages and risks
Exchange funds generally involve long lockups and limited liquidity. The tax liability is deferred, not eliminated.
Additional considerations may include:
High investment minimums
Management and administrative fees
Partnership tax reporting and Schedule K-1s
Limited visibility or control over portfolio holdings
Manager selection risk
The possibility that a fund will reject an overrepresented stock
Exposure to illiquid or nontraditional qualifying assets
An exchange fund should not be viewed as a tax-free escape hatch. It exchanges a concentrated position for a different, though generally more diversified, set of risks.
4. Qualified Opportunity Funds
How the strategy works
A Qualified Opportunity Fund, or QOF, invests in businesses or real estate located in designated Opportunity Zones. Congress created this program to encourage long-term investment in specific communities.
Unlike an exchange fund, an investor generally sells the concentrated stock first and then reinvests the eligible capital gain into a QOF within the applicable time period.
Under the legacy Opportunity Zone rules, eligible gains recognized before January 1, 2027 may be deferred only until the earlier of an inclusion event or December 31, 2026.
The legacy 5- and 7-year basis increases on the original deferred gain are no longer available to new 2026 investments because the deferral period ends too soon. A separate benefit may remain: after a qualifying QOF investment has been held for at least 10 years, the investor may generally elect to increase the basis of the QOF interest to its fair market value at disposition, potentially excluding post-investment appreciation.
This distinction is critical. The 10-year benefit applies to appreciation inside the QOF investment; it does not erase the original gain from selling company stock. Date-sensitive planning should be reviewed with a qualified tax advisor before implementation.[9]
Potential advantages
A QOF may allow an investor to sell a concentrated stock position, remove company-specific risk, and redirect the eligible gain into a new investment with potential tax benefits.
Potential benefits may include:
Deferral of eligible gains under the applicable rules
Potential favorable treatment of long-term appreciation inside the QOF
The ability to invest the eligible gain rather than the entire sale proceeds
Access to real estate development, private businesses, or economic growth projects
For an investor who already wants exposure to a particular Opportunity Zone investment, the tax treatment can be a meaningful additional benefit.
Potential disadvantages and risks
Many QOFs are illiquid and designed around long development or operating timelines.
Risks may include:
Real estate, development, and construction risk
Geographic or project concentration
Manager and sponsor risk
High fees and complex fund structures
Limited secondary-market liquidity
Changes in tax law or regulatory interpretation
The possibility that tax benefits will not compensate for poor investment performance
A QOF should be evaluated as an investment first and a tax strategy second. Tax deferral does not offset a poor underlying investment.
5. Variable Prepaid Forward Contracts
How the strategy works
A variable prepaid forward contract may allow an investor to receive liquidity from a concentrated stock position today while agreeing to deliver shares or cash at a future date.
The investor enters into a contract with a financial institution. The institution advances a percentage of the stock’s current value. In exchange, the investor agrees to deliver a variable number of shares when the contract matures. The shares are often pledged as collateral.
The final number of shares is commonly determined by the stock’s price relative to two predetermined price levels:
Below the lower price, the investor may deliver the maximum number of shares.
Between the lower and upper prices, the investor delivers enough shares to satisfy a specified value.
Above the upper price, the investor may deliver fewer shares but gives up some appreciation beyond the contract’s cap.
IRS Revenue Ruling 2003-7 addressed one specific variable prepaid forward structure that did not result in an immediate sale or constructive sale. The tax outcome of any transaction depends heavily on its exact terms and the investor’s continuing economic exposure.[10]
Potential advantages
When structured properly, a variable prepaid forward may provide immediate cash without requiring the investor to recognize the entire gain when the contract is established.
Proceeds might be used to:
Diversify into other investments
Fund a home purchase or business venture
Pay taxes associated with option exercises
Support charitable or estate-planning goals
Create liquidity before a future stock sale
The transaction may also provide partial downside protection while preserving a negotiated amount of upside participation.
Potential disadvantages and risks
Variable prepaid forwards are complex, expensive, and generally designed for very large concentrated positions.
Potential drawbacks include:
Significant legal, tax, advisory, and structuring costs
Counterparty credit risk
Collateral requirements
Limited upside participation
Restrictions on transferring or using pledged shares
Complex tax reporting
Constructive-sale or recharacterization risk
A future tax bill when the contract settles
Difficulty unwinding the agreement before maturity
The embedded gain does not disappear. The strategy generally moves liquidity forward while potentially moving tax recognition into the future. Small changes in settlement rights, collateral arrangements, or related hedging activity can materially change the tax result.
MAIA WEALTH / CREATOR FINANCIAL EDUCATION
Updated October 2026 · Educational material only; not individualized investment, tax, or legal advice.
Content creators face unique financial challenges, from managing irregular income to planning for taxes, retirement, and long-term wealth.
Understanding how creator income is taxed can help you prepare for conversations with your tax professional and make more informed financial decisions. This guide explains common federal tax considerations for content creators, including self-employment taxes, estimated payments, business deductions, and retirement accounts. It also explores how these considerations fit into a broader financial plan.
Maia Wealth provides investment management and financial planning services. We help creators understand how tax considerations interact with their financial goals and work alongside qualified tax professionals when specialized tax guidance is needed.
Quick answer: How do taxes work for content creators?
Most creators who earn money independently are treated as self-employed for federal tax purposes. That usually means reporting business income and expenses on Schedule C, calculating Social Security and Medicare taxes on Schedule SE, and making estimated payments during the year when withholding will not cover the expected bill. Cash, free products received for services, sponsorships, subscriptions, affiliate commissions, and platform income may all be taxable.
Key Takeaways
Creator income creates multiple tax obligations: Self-employment taxes generally come on top of federal and applicable state income taxes, so variable income requires deliberate cash-flow planning.
Plan for irregular income: Maintain appropriate tax reserves and review estimated-payment needs with a qualified tax professional as revenue changes.
Business deductions deserve a closer look: Equipment, production, and qualifying travel expenses may be deductible; a tax professional should assess eligibility.
Business structure can affect your financial plan: An LLC does not automatically lower taxes, and S-corporation elections require individualized tax analysis.
Retirement planning may offer significant opportunities: A Solo 401(k) or SEP IRA may allow eligible creators to defer tens of thousands of dollars of current income; very high earners may also explore cash balance plans with professional guidance.
Coordinate financial and tax professionals: Maia Wealth focuses on investment, retirement, and cash-flow planning while working with qualified tax professionals on specialized tax questions.
Are content creators self-employed?
Many creators are self-employed because they operate as sole proprietors, independent contractors, single-member LLC owners, or partners. The IRS also treats part-time gig work as self-employment when the underlying facts support that classification. A creator may simultaneously have W-2 wages from an employer and self-employment income from sponsorships, platform payouts, or freelance creative work.
A person generally must file and calculate self-employment tax when net earnings from self-employment are $400 or more. That rule can apply even when content creation is a side business.
Important: The $400 threshold generally determines whether self-employment tax applies. It does not mean that creator income below $400 is automatically exempt from federal income tax or reporting requirements. Whether income must be reported depends on the taxpayer’s broader circumstances.
Creator income that may be taxable
Sponsorships
COMMON EXAMPLE
Cash payment for a TikTok, YouTube integration, podcast read, or newsletter placement.
Do not use the arrival or absence of a Form 1099 as the definition of taxable income. The IRS says gig-economy income must generally be reported even if it was paid in cash, property, goods, or virtual currency and even if no information return was issued.
Creators taxed as partnerships or S corporations use different business returns and receive different reporting documents. The forms do not determine whether income exists; they help report income that must already be tracked in the creator’s books.
Self-employment tax generally combines a 12.4% Social Security component and a 2.9% Medicare component. The IRS generally applies these percentages to 92.35% of net self-employment earnings. For 2026, the Social Security portion is limited by the $184,500 Social Security wage base, while Medicare tax has no comparable wage cap. An additional 0.9% Medicare tax can apply above filing-status thresholds. These are general rules; calculations can differ with other wages and individual circumstances. Self-employment taxes are generally owed in addition to federal and applicable state income taxes, not in place of them.
How much should a content creator save for taxes?
There is no universal percentage that works for every creator. Federal income-tax brackets, state and local taxes, deductions, filing status, W-2 withholding, retirement contributions, and business structure all affect the answer.
A percentage such as 25% or 30% can be a cash-management starting point, but it is not a tax calculation. Maintain a separate account for anticipated tax payments and periodically review income with a qualified tax professional.
Federal estimated-tax rules generally allow taxpayers to avoid underpayment penalties by paying at least 90% of their current-year tax liability or 100% of the prior year’s liability, whichever is smaller. For certain higher-income taxpayers, the prior-year threshold increases to 110%. Additional requirements and exceptions apply, including timing and prior-year return conditions.
For creators with unpredictable income, these rules can help with cash-flow planning. A qualified tax professional can determine the appropriate payment amounts and deadlines based on individual circumstances. Revisit projections after a major sponsorship, product launch, viral month, large equipment purchase, business-structure change, or change in household income.
2026 Federal Estimated-Tax Dates
INCOME PERIOD
January 1 – March 31
GENERAL PAYMENT DATE
April 15, 2026
INCOME PERIOD
April 1 – May 31
GENERAL PAYMENT DATE
June 15, 2026
INCOME PERIOD
June 1 – August 31
GENERAL PAYMENT DATE
September 15, 2026
INCOME PERIOD
September 1 – December 31
GENERAL PAYMENT DATE
January 15, 2027
These periods are not equal quarters. Weekend, holiday, fiscal-year, annualized-income, farming, fishing, and other special rules can change the calculation or date. A creator with highly seasonal income may benefit from the annualized-income installment method rather than four identical payments.
Business Expenses and Tax Deductions for Content Creators
Content creators often have access to business deductions that traditional W-2 employees generally do not. Depending on the nature of their business, these may include expenses creators overlook.
Some examples worth discussing with a tax professional include:
Equipment and Technology: Cameras, microphones, lighting, computers, and editing software.
Home Office Expenses: Qualifying business use of a workspace.
Travel and Transportation: Business-related travel, mileage, lodging, and transportation.
Professional Services: Accounting, legal, and other business-related professional fees.
Marketing and Production: Advertising, website hosting, editing services, and production costs.
Products and Props: Items acquired for content creation, subject to applicable rules and personal-use limitations.
While these expenses may qualify for deductions, determining specific deductibility is outside the scope of Maia Wealth’s expertise. We coordinate with qualified tax professionals who can help clients determine which expenses are deductible based on their individual circumstances.
For a deeper look at potential deductions, explore these educational resources:
These third-party resources are provided for education, not as an endorsement of their tax advice. Confirm your circumstances with a qualified tax professional.
Does an LLC reduce a creator’s taxes?
Forming an LLC under state law does not, by itself, create a federal tax deduction or automatically reduce self-employment tax. A single-member LLC is commonly disregarded for federal income-tax purposes unless it elects another treatment. Liability, contract, privacy, banking, and state-law benefits can still be important.
Some creators explore whether an S-corporation election could improve their overall tax situation. However, an S corporation is not automatically advantageous, and potential benefits depend on factors such as business profitability, reasonable compensation requirements, payroll expenses, and existing employment income.
The Social Security wage base, Medicare taxes, retirement contributions, and qualified business income deduction can also affect the analysis. Because these calculations depend on individual circumstances, creators should consult a qualified tax professional before making an entity election. A financial advisor can help evaluate how different business structures may affect retirement planning, investment strategies, cash flow, and long-term financial goals.
Financial Considerations Before Discussing an S-Corporation Election
Discuss stable annual business profit before owner wages with a qualified tax professional.
Ask how reasonable compensation is established for the services actually performed.
Consider the cash-flow effects of payroll, employer costs, and potential distributions.
Understand the added administrative expenses, state fees, and retirement-plan effects.
Stress-test the structure under a weak-revenue year, not only the creator’s best year.
If the projected net benefit is small, volatile, or dependent on an unrealistically low salary, the added structure may not be worthwhile.
Retirement Planning: One of the Biggest Tax Opportunities for Content Creators
One of the biggest financial advantages of being self-employed is access to retirement accounts that may allow you to defer significantly more income than a traditional IRA.
For successful content creators, a Solo 401(k) or SEP IRA can potentially defer tens of thousands of dollars from current federal income taxes each year, while building long-term wealth.
Why Is This Such a Big Deal?
Self-employed creators may be able to establish their own retirement plans. For 2026, the general defined-contribution annual additions limit is $72,000 before eligible catch-up contributions. That ceiling is not an automatic contribution allowance: the actual amount depends on eligible compensation, plan type, contribution formulas, other plans, and applicable rules.
For illustration, at a hypothetical 32% marginal federal income tax rate, a qualifying $50,000 pretax retirement contribution could reduce current federal income tax by approximately $16,000. This is a simplified example, not a projection or guaranteed result.
The contribution remains invested for retirement, and traditional retirement-account withdrawals are generally taxable later. Early withdrawals may trigger additional taxes. Pretax retirement contributions generally do not eliminate self-employment taxes.
Solo 401(k) vs. SEP IRA: Which Makes Sense?
Solo 401(k): Generally designed for a self-employed business owner with no eligible common-law employees other than a spouse. It may allow both employee and employer contributions, providing useful flexibility.
SEP IRA: Funded through employer contributions. It may be simpler to administer, but contribution calculations and employee coverage requirements differ.
The best fit depends on business income, entity structure, employees, other retirement plans, and financial goals.
For Very High Earners: Cash Balance Plans
Creators with consistently high business profits may also consider a cash balance pension plan, a type of defined-benefit retirement plan that can sometimes support substantially larger tax-deductible employer contributions than a Solo 401(k) or SEP IRA alone.
The potential current-year tax deferral can be significant, especially for high earners, but these plans are complex and generally involve actuarial calculations, ongoing administration, and required funding commitments that are much less flexible than contributions to many defined-contribution plans.
Funding obligations, employee coverage, and plan costs must be evaluated carefully, particularly when creator income is unpredictable. A qualified retirement-plan specialist and tax professional should assess feasibility and contribution amounts before a plan is established.
Don’t Let Your Highest-Earning Years Go to Waste
Creator income can be unpredictable. A major sponsorship, viral video, or successful launch might create an unusually profitable year that is not guaranteed to repeat. Those years can offer an opportunity to accelerate retirement savings and potentially defer current income taxes.
At Maia Wealth, we help creators evaluate retirement account options, develop investment strategies, and incorporate contributions into a broader financial plan. We coordinate with qualified tax professionals on individual tax implications.
What About the Qualified Business Income Deduction?
Some eligible creators may also qualify for a qualified business income (QBI) deduction of up to 20% of qualified business income, subject to restrictions. Its availability and interaction with business structure and retirement contributions should be evaluated by a qualified tax professional.
Before year-end, review retirement contributions, equipment timing, entity structure, insurance, charitable plans, and cash needs with the relevant professionals.
Common Content Creator Tax Mistakes
Waiting for 1099s to determine revenue. Forms can be missing, duplicated, corrected, or issued under different names.
Saving a flat percentage without recalculating. A reserve rule may miss household income, state tax, or a breakout month.
Deducting personal lifestyle costs because they appeared on camera. Content does not automatically transform a personal expense into a business expense.
Ignoring non-cash compensation. Products, travel, gift cards, and services can carry taxable value.
Mixing business and personal accounts. Commingling makes bookkeeping and substantiation harder.
Treating an LLC as a tax strategy. Legal structure and tax classification are different decisions.
Electing S-corporation treatment based on a social-media threshold. Reasonable compensation and administrative costs are fact-specific.
Using outdated mileage rates or retirement limits. Check current IRS announcements.
Missing state and local issues. Travel, residency, employees, sales, and business registrations can create obligations beyond federal income tax.
Calling a professional only after receiving a notice. Planning is usually more valuable before the transaction or deadline.
When Should a Creator Hire a Tax Professional?
Professional help becomes especially valuable when a creator:
Earns substantial income from several platforms or entities.
Receives royalties, usage-rights payments, foreign income, or digital assets.
Works or earns income in multiple states or countries.
Hires employees or contractors.
Is considering an LLC, partnership, or S-corporation election.
Has a spouse with significant wages, equity compensation, or business income.
Wants to coordinate retirement contributions, charitable planning, and cash-flow needs.
As a creator’s business grows, financial planning and tax planning become increasingly interconnected. A qualified tax professional can provide specialized tax guidance, prepare returns, and evaluate tax elections. A financial advisor helps coordinate investment management, retirement planning, risk management, and long-term financial decisions while considering their potential tax implications.
At Maia Wealth, we focus on comprehensive financial planning and investment management. When specialized tax questions arise, we encourage clients to work with qualified tax professionals so that financial decisions can be evaluated from both perspectives.
Build a Financial System Before Tax Season
Creator finances become easier to manage when income is captured, expenses are documented, reserves are separated, and projections are reviewed before deadlines. The goal is to avoid preventable surprises and make better decisions about cash flow, retirement, and long-term wealth.
Content creators with increasingly complex income, investments, and tax considerations may benefit from working with advisors who understand the creator economy. J. Roark Huene, AIF® and Matthew Tamanaha, AIF® work with creators through Maia Wealth.
MAIA WEALTH
Turn Creator Income Into Long-Term Wealth
Building a successful creator business is one thing. Turning that success into lasting financial security is another.
At Maia Wealth, we help content creators develop financial strategies around investing, retirement, cash-flow management, and long-term wealth accumulation. We also consider how taxes may affect financial decisions and coordinate with qualified tax professionals when appropriate.
If you work at Lockheed Martin, there is a good chance your employee benefits could be doing more for you than you realize.
That becomes especially important as your income, retirement savings, and exposure to Lockheed stock grow.
You may already be doing a lot of things right. You contribute to your 401(k). You receive the company match. You understand when your RSUs vest. Maybe you are already maxing out your normal retirement contributions.
But that does not necessarily mean you are getting the full value out of the benefits available to you.
Some of Lockheed’s most useful planning opportunities are easy to miss because they sit one layer beneath the obvious benefits.
Your 401(k) may give you access to a much broader investment universe than the normal fund menu. You may have an additional opportunity to build Roth assets after reaching the standard contribution limit. Retiree healthcare could change how early you are able to retire. And if you are required to hold Lockheed stock, you may need to build the rest of your investment strategy around that concentration.
The important question is not simply whether you are using these benefits. It is whether you are using them in the right way, at the right time, and as part of one coordinated financial plan.
Here are four areas we think higher-earning Lockheed employees should understand.
1. Your 401(k) May Be More Flexible Than You Think
Most employees treat their 401(k) like a menu. You log into Empower, choose from the investments available to you, decide how much to put into each one, and move on. You may even be choosing one, simple target date fund for your entire 401(k)
That may be perfectly fine to the average investor, but Lockheed’s retirement plan also provides access to a Self-Directed Brokerage Account, or SDBA, which can give you access to a much broader range of investments.
That broader investment access can be paired with Schwab’s Personal Choice Retirement Account, or PCRA.
The reason this matters is simple:
You may not have to build your retirement portfolio entirely from the standard investment choices you see inside Empower.
Depending on the investments permitted by the plan, you may have access to individual stocks, bonds, mutual funds, ETFs, publicly traded real estate, and other publicly traded investments.
That can also include funds designed to diversify beyond a traditional mix of stocks and bonds, such as investments tied to real estate, real assets, commodities, structured strategies, or funds that combine several different investment approaches.
Why should you care?
Because as your financial life gets more complicated, your 401(k) becomes less useful if you look at it by itself. You may already have:
Lockheed stock
RSUs
A taxable brokerage account
Real estate
Roth assets
Cash
Other retirement accounts
If your 401(k) is invested without considering everything else you own, you may be taking more risk than you realize or missing opportunities to diversify more effectively.
This is especially important if a large percentage of your wealth is already tied to Lockheed Martin. You may feel diversified because your 401(k) owns dozens or hundreds of companies. But if your career, paycheck, RSUs, and a meaningful portion of your investments are all connected to Lockheed or large U.S. companies, your overall financial picture may still be more concentrated than it looks.
A PCRA can give you more tools to build around that.
You may also be able to have it professionally managed
For eligible accounts, an outside advisor may be able to manage the investments inside the PCRA. That can allow your Lockheed retirement assets to be considered alongside the rest of your portfolio instead of being treated as a completely separate account.
And that changes the question from:
“Which fund should I pick in my 401(k)?”
to:
“How should all of my investments work together?”
If you have built a sizable 401(k), that can be a much more important question.
2. Maxing Out Your 401(k) May Not Mean You Are Done
This is one of the Lockheed benefits that higher earners can easily overlook. You probably know there is an annual limit on how much you can contribute to your 401(k) through normal pre-tax or Roth contributions.
Once you hit that number, it is easy to assume you are finished.
But Lockheed’s plan may allow you to make additional non-Roth after-tax contributions after you have reached the normal contribution limit.
That sounds similar to a Roth contribution, but it is not the same thing. Both contributions are made with dollars you have already paid taxes on and the difference is what happens next.
If non-Roth after-tax money is left sitting in the account, the investment growth generally grows tax-deferred, similar to money in a traditional pre-tax 401(k).
Lockheed’s plan also allows certain in-plan Roth conversions. That may allow eligible non-Roth after-tax contributions to be converted into Roth assets.
This is the foundation of what is commonly called a mega backdoor Roth strategy.
Why should you care?
Because if you are already maxing out your normal 401(k), you may still have another opportunity to build additional Roth retirement assets. That can matter later.
If most of your retirement savings are pre-tax, you may eventually have a large pool of money that creates taxable income when you withdraw it.
Building Roth assets gives you another bucket to work with.
By retirement, you may have money spread across:
Pre-tax retirement accounts
Roth retirement accounts
Taxable investments
Lockheed stock
That can give you more flexibility when deciding where retirement income should come from and how much taxable income you want to create in a given year.
This is also where mistakes can happen
The Roth opportunity and the PCRA opportunity are not completely separate. How and when money is moved between different parts of the plan can matter.
For example, moving certain non-Roth after-tax assets into a self-directed brokerage account before completing an intended Roth conversion may create additional steps or complications.
You do not need to memorize the mechanics.
The important thing to know is this:
If you are using both the SDBA and the mega backdoor Roth feature, the order matters.
We have seen this become unnecessarily complicated simply because the two benefits were treated as separate decisions.
If you are already contributing aggressively to your Lockheed 401(k), this is an area worth reviewing before assuming you have fully maximized the plan.
3. Your Lockheed Healthcare Benefits Could Affect When You Retire
You can have enough money to retire and still feel like you cannot retire.
Healthcare is often the reason.
If you want to leave Lockheed before age 65, there can be a long gap between your retirement date and Medicare eligibility and health insurance during that period can be expensive.
Lockheed maintains retiree healthcare options for certain eligible retirees under age 65.
The exact eligibility rules and costs can depend on your individual circumstances, service history, and current plan provisions, so this is something you should verify before building it into a retirement plan.
But if you qualify, it could change your retirement math.
Think about the actual problem
Suppose you are 58.
Your investments are strong. Your mortgage is manageable. You have enough savings to support your lifestyle.
You would like to retire, but you assume you need to keep working because you do not want to pay for seven years of expensive health insurance before Medicare. If you qualify for Lockheed retiree medical coverage, you may have another option.
You may still be responsible for some or all of the premium, and the coverage may not be cheap, but it could compare favorably with alternatives such as COBRA or Marketplace coverage. That means this benefit can become much more than an insurance decision.
It can become part of the answer to:
“Can I retire yet?”
We have found that many people spend years focused on hitting a retirement account number without realizing that one benefit can materially change the amount they actually need before leaving work.
If early retirement is even remotely on your radar, this is something you should understand before simply assuming 65 is your earliest realistic retirement age.
4. Your Lockheed Stock May Be Creating More Risk Than You Realize
For certain Lockheed executives and senior employees, owning LMT stock may not be entirely optional. Lockheed maintains stock ownership requirements for a number of senior positions. Published executive requirements vary by role and can be expressed as a multiple of annual salary.
Examples include:
Published Stock Ownership Requirements
Required LMT stock ownership shown as a multiple of annual base salary
CEO and Chairman
6x
CFO and COO
4x
Business Segment Presidents
3x
Senior Vice Presidents and certain Vice Presidents
2x
Measurement: Multiple of base salary
Other internal requirements may apply to additional positions, so you should confirm the requirement specific to your role.
At first glance, this may not seem like a major planning issue, but think about how much of your financial life may already depend on Lockheed. Your salary comes from Lockheed, your bonus may depend on Lockheed and your RSUs are tied to Lockheed. You may even own LMT through your retirement plan or a personal account.
And your position may require you to hold even more LMT stock. That can create a level of concentration that is easy to underestimate.
The issue is not whether LMT is a good investment
You may have tremendous confidence in the company. That is not the point. The issue is that one company can begin to control too many parts of your financial life at the same time.
If Lockheed performs well, that concentration may work heavily in your favor, but if the stock struggles, your investment portfolio, compensation, and career may all be affected at once.
That is why the investments outside your Lockheed stock become increasingly important. If you are required to maintain a large LMT position, the rest of your portfolio may need to do more of the diversification work.
This is another reason the flexibility available through a PCRA can matter.
You may not be able to hedge the risk while you are still employed
Lockheed also restricts employees, officers, and directors from using certain strategies designed to hedge or monetize Lockheed stock. That means some of the tools investors might normally use to manage a concentrated stock position may not be available to you while you are employed.
By the time you retire or leave Lockheed, you could be sitting on a large LMT position with significant unrealized gains.
Then the problem changes. You may want to diversify, but selling a large position all at once can create a significant tax bill. At that point, you are no longer dealing with one investment decision, you are dealing with diversification, taxes, retirement income, trading restrictions, and potentially estate planning at the same time.
That is why we believe planning around a concentrated LMT position should begin before the day you decide you want to sell it.
The Biggest Mistake Is Looking at These Benefits One at a Time
This is the part we think matters most.
You do not have a PCRA problem.
You do not have a Roth problem.
You do not have a Lockheed stock problem.
You do not have a retiree healthcare problem.
You have one financial plan, and each benefit can affect the others. Your LMT concentration may influence how the rest of your retirement portfolio should be invested. Your Roth strategy may affect which types of accounts you have available later. How you use the PCRA can affect how certain Roth transactions need to be handled. Your healthcare benefits may change how much money you actually need before retiring.
The mistake is assuming that because you are using each benefit individually, you are necessarily using them efficiently together. You may be, but you may not be. And as your net worth grows, the cost of getting that coordination wrong can grow with it.
Are You Actually Getting Everything You Can From Your Lockheed Benefits?
That is the question we think is worth asking. You may already have a strong 401(k), you may already be contributing aggressively, you may already own substantial Lockheed stock and you may already be thinking about retirement. But none of those things tells you whether your benefits are being used as effectively as they could be.
The answer depends on your income, age, role at Lockheed, service history, tax situation, portfolio, stock concentration, and retirement goals. That is where planning becomes valuable.
At Maia Wealth, we help Lockheed employees look at these benefits as one connected system rather than a collection of separate accounts and programs.
We can help you identify which opportunities may apply to you, where there may be gaps in your current strategy, and how your Lockheed benefits fit into the rest of your financial life.
Want to find out whether your Lockheed benefits could be doing more for you? Schedule a Lockheed Benefits Review with Maia Wealth. Schedule a Lockheed Benefits Review
Important Disclosure
The information presented in this newsletter is the opinion of Maia Wealth and does not reflect the view of any other person or entity. The information provided is believed to be from reliable sources but no liability is accepted for any inaccuracies. This is for information purposes and should not be construed as an investment recommendation. Past performance is no guarantee of future performance. Maia Wealth is an investment adviser registered with the U.S. Securities and Exchange Commission.
A Milestone Worth Celebrating
We are excited to share that Maia Wealth has been named one of Colorado’s Fastest-Growing RIAs by Citywire as part of their 50 Growers Across America 2025 report.
This recognition highlights our firm’s continued growth, our advisors’ commitment to excellence, and most importantly, the trust and partnership of the incredible clients we are honored to serve every day.
Citywire’s annual Growers Across America list identifies RIA firms demonstrating exceptional momentum, strategic growth, and client-focused innovation.
With $840.67M in assets under management as of August 9, 2025, Maia Wealth is proud to be recognized for:
Helping individuals and families achieve their long-term financial goals
This achievement is a reflection of our outstanding advisors, our collaborative culture, and the strong foundation built together with our clients and partners.
Thank You
A heartfelt thank you to:
Our amazing advisors, whose dedication drives everything we do
Our clients, who trust us with their financial futures
Citywire, for recognizing our growth among such exceptional firms
We look forward to carrying this momentum into the year ahead—and continuing to deliver clarity, confidence, and personalized guidance for every client we serve.
Navigating your financial future can feel complex, but understanding key concepts is the first step towards achieving your goals. This comprehensive glossary provides clear, concise answers to the 100 most frequently asked financial planning questions on Google, designed to empower you with the knowledge you need for a secure financial journey.
We’re thrilled to spotlight Maia Wealth’s very own advisor, Liz Windisch!
Liz was recently featured in a thoughtful article in USA Today, exploring why many U.S. millionaires don’t actually “feel wealthy”. The USA Today piece digs into a surprising truth: even millionaires can feel uncertain about their financial future. It sheds light on the emotional side of wealth, from rising expenses to shifting expectations, and why thoughtful planning matters now more than ever.
Liz’s insights highlight an important truth: wealth isn’t defined by a balance sheet, but by confidence, purpose, and a plan you can trust. Her perspective emphasizes how mindset and long-term strategy shape a genuine sense of financial security.
We’re thrilled to share that Maia Wealth has been named one of America’s Top Financial Advisory Firms by Newsweek for the second year in a row (2025 & 2026)! 🎉
The ranking, presented by Newsweek in partnership with Plant-A Insights, evaluated over 1,000 firms nationwide, considering factors such as assets under management, advisor expertise, client outcomes, breadth of services, and more. Only firms with a proven track record, multiple advisors, and SEC registration were included.
We’re proud to be listed among top firms across the country and grateful to our clients and team of advisors here at Maia Wealth that continue to demonstrate trustworthiness, expertise, and a strong reputation in helping clients achieve their financial goals.
Here’s to continuing to deliver exceptional financial guidance and a future of continued growth 🤗
