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Restricted Stock Units – RSU 08.04.2021

Restricted Stock Units (RSUs) can be a significant component of an employee’s compensation package. But what exactly is an RSU? How are they treated for tax purposes? How do you plan most effectively when your RSUs vest? The 411 on Restricted Stock Units will tackle these questions and more.

What are Restricted Stock Units?

RSUs, also commonly known as restricted stock shares, are a form of stock based compensation whereby an employee receives rights to shares of stock in a company that are subject to certain restrictions. These units do not represent actual ownership or equity interest in the company and as such hold no dividend or voting rights. (1) However, once the restriction is lifted, the units are converted to actual company shares and an employee owns the  shares outright (same as traditional stock ownership).  

The restriction on the units is generally based on a vesting schedule. Most vesting schedules will fall into one of two categories:

  • Time-based: based on the period of employment. Common time-based vesting schedules are between three to five years and are either pro-rata or “cliff” based. For a “cliff” based schedule, all shares vest fully at the end of the schedule.       
  • Performance-based: based on the company achieving a performance goal. Common performance-based vesting schedules are based on a company achieving a particular stock price or a return on equity, or earnings per share.    

    *There is a hybrid-approach between time-based and performance-based known as time-accelerated. Vesting is on a time-based schedule but may be accelerated by the company achieving a performance-based goal.  

How Are RSUs Different Than Vested Stock Options?

When most people think of stock based compensation, vested stock options, or the right to buy a company’s stock at some future date at a price established now (the strike price), are typically what first comes to mind.  

Historically, vested stock options have been the most popular form of stock based compensation. And up until 2004, stock options merited favorable accounting treatment as a company could avoid recognizing compensation expense by issuing the options.  

In 2004, this loophole was eliminated and subsequently RSUs/restricted stock shares, aka units, emerged as the preferred form of equity compensation.  

RSUs and stock options have some notable differences:

RSU Vested Stock Options Restricted Stock Units

Scenario 1: An employee is granted 1,000 RSUs when the market price of the company’s stock is $10. When the RSUs vest, the stock price has fallen to $8. The shares are still worth $8,000 to the employee.  

Scenario 2: An employee is granted 1,000 stock options with a strike price of $10. During the window to exercise these vested options, the market price of the stock is always below $10. These options will expire worthless to the employee.  

*There are many other forms of nontraditional compensation, such as Stock Appreciation Rights (SARs), Phantom Stock, and Profit Interests. None of these are as widely used as RSUs or Stock Options and will not be a focus in this paper.

What Is the Taxation of Restricted Stock Units?

RSUs are taxed upon delivery of the shares (i.e., when the restriction has been lifted).     

At time of delivery, the shares are included in an employee’s taxable income as compensation at the fair market value of the total shares. The taxation of restricted stock units is identical to normal wage income and as such, is included on an employee’s W-2. (3)    

Taxation of Restricted Stock Units? Shares Stock Market White Paper Towerpoint Wealth

The shares are subject to federal and employment tax (Social Security and Medicare) and state and local tax as well.     

For paying the taxes due on delivery, companies will provide an employee with either one uniform withholding method or several options as follows:

  • Net-settlement:a company “holds back” shares to cover the taxes and then the company pays the tax from its own cash reserve. This is the most common practice.      
  • Pay cash: an employee receives all shares and covers the income tax burden out of their own pocket. This is a riskier strategy than net-settlement, as it results simultaneously in a more concentrated equity allocation and lower cash balance (less money to pay the taxes).
  • Sell to cover:an employee sells the shares needed to cover the income tax burden on their own. This method provides no real advantage over net-settlement and places the additional burden of selling the shares on the employee.   

When an employee ultimately sells their vested shares, they will pay capital gains tax on any appreciation over the market price of the shares on the vesting date. If the shares are held longer than one year after vesting, the sales proceeds will be taxed at the more favorable long-term capital gains rate. (4)

Restricted Stock Units Stock Options Vesting Dates Towerpoint Wealth

Taxation of Restricted Stock Units Example:

An employee is granted 750 Restricted Stock Units on January 1, 2018. The market price of the stock at the time of

An employee is granted 750 RSUs on January 1, 2018. The market price of the stock at the time of grant is $10 and the RSUs vest pro-rata over three years: 

Each increment is taxable on its vesting date as ordinary income. The total ordinary income paid over the three years is $11,500. 

Each increment is taxable on its vesting date as ordinary income. The total ordinary income paid over the three years is $11,500.

The employee then sells all 750 shares of stock three years after the last shares vest:

The employee held each share for more than one year, so the gain is treated as long-term. The employee’s long-term capital gain is $11,000 ($22,500 less $11,500) to be reported on Schedule D of their U.S. individual tax return.

What Are the Risks of Holding RSUs?

Utilized correctly, restricted stock units/restricted stock shares can be a wonderful complement to a traditional compensation package and can contribute substantially to an employee’s net worth. (5) This can be, however, a double-edged sword.

The overlying risk is that an employee can have too much of their net worth concentrated in one individual stock and for that matter, one individual company.

Let’s explore a scenario:

Jim has a net worth of $200,000, not including 2,000 shares of RSUs with his employer,  Snap Inc. On January 1, 2019, 100% of Jim’s 2,000 RSUs vest at $50 per share.

Great news! Jim’s net worth, on paper, has now increased by $100,000 overnight. Jim’s overall net worth is now $300,000

Jim decides to keep all his shares in Snap Inc. with the belief the stock price will continue to go up. 

He also sees his colleagues choosing to hold most of their shares, and fears that if Snap Inc.’s price soars, he will have missed out and his colleagues will all become wealthier than him. 

On July 1, 2019, Snap Inc. releases a weak earnings report and the share price drops to $20. Jim’s net worth is now $240,000, down 20% from January 1st. 

Even worse, Jim paid taxes at his ordinary rate on the original share value of $100,000 when the shares are now only worth $40,000.

And finally, because Jim has a significant portion of his net worth in the company he works for, he faces an additional and potentially catastrophic risk. What if Snap Inc. runs into serious financial struggles and he loses his job? Not only will Jim’s net worth plunge from further declines in Snap Inc.’s share price, he also will now have lost his primary source of income.

How Can I Most Effectively Plan for RSUs?

We recommend you discuss how to effectively plan for RSU shares with your financial advisor to ensure a decision is not made in a vacuum, but rather in the broader spectrum of your entire financial picture. Of course, we encourage collaboration with your tax advisor to determine the optimal strategy from a tax perspective as well.  

In reality, when RSUs vest, you may be better off by immediately (or over a short-term schedule) selling a sizeable portion of the vested units and using the proceeds to add to or build a diversified investment portfolio.    

Regardless, before you make any decisions, it can be helpful to explore the following questions:   

  • How much of your overall wealth is tied up in RSUs?  
  • Is your company growing quickly or slowly?   
  • What is your current tax situation? Is it better to wait more than one year after the shares vest to sell them to receive the more favorable long-term capital gains tax treatment?  
  • How long do you plan to be with the company?
  • What is your tolerance for risk?
  • If the market value of the stock was instead received in the form of a cash bonus, how much of this would you invest in the company stock?   

How can we Help?

While we at Towerpoint Wealth continue to believe in the importance of a diversified portfolio, we also understand every individual situation is unique, what growing net worth means to each individual is different, and understand emotions can play a significant albeit oftentimes problematic role in making sound financial decisions. This is especially the case for RSUs. If you would like to speak further about RSUs (or any nontraditional compensation for that matter), I encourage you to call, 916-405-9166, or Steve Pitchford (Sacramento Certified Financial Planner) email

Download The 411 on Restricted Stock Units, RSUs

Learn more about Restricted Stock Units on our YouTube Channel

(1)   While RSUs hold no automatic dividend rights, companies may choose to issue dividend equivalents. For example, when a company pays cash dividends to common stock holders, RSUs can be credited dividends for the same amount. These credits may ultimately be used to pay the taxes due when RSUs vest or can simply be paid out in cash.

(2) Stock Options can either be Incentive Stock Options (ISOs) or Nonqualified Stock Options (NQOs). They are treated differently for tax purposes.  

(3) When received, dividend equivalents are subject to the same tax rules as RSUs.

(4) Important to note that the shares must be held more than one year for long-term capital gains treatment. If sold exactly one year from the vesting date, they will be taxed at the higher short-term capital gains. 

(5) Net worth means the total value of all of an individual’s assets less their liabilities.

Towerpoint Wealth, LLC is a Registered Investment Adviser. This material is solely for informational purposes. Advisory services are only offered to clients or prospective clients where Towerpoint Wealth, LLC and its representatives are properly licensed or exempt from licensure. Past performance is no guarantee of future returns. Investing involves risk and possible loss of principal capital. No advice may be rendered by Towerpoint Wealth, LLC unless a client service agreement is in place.

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Six Strategies to Optimize Your Charitable Intentions 04.13.2021

By: Matt Regan, Wealth Advisor and Steve Pitchford, Director of Tax and Financial Planning
Published: April 13, 2021

Six Strategies to Optimize Your Charitable Intentions | Most individuals who are philanthropically inclined usually just take the path of least resistance and write a check directly to a charity. Of course, this is a straightforward approach and can qualify for an income tax deduction, but when being charitable, there are many different (and often economically more advantageous) options and strategies available to you. Indeed, with strategic and thoughtful planning, a taxpayer may be able to optimize their gifting strategy, meeting multiple objectives by maximizing the economic benefits 1.) to themselves, 2.) to their favorite charities, and even 3.) to their loved ones.

Are you optimizing your philanthropy and gifting strategy? Below you will find a myriad of different charitable strategies we regularly employ for Towerpoint Wealth clients, designed to help you better understand your options.

Cash/Direct to Charity

A cash gift is the simplest and (by far) most popular form of charitable giving.

The income tax deduction[1] for a cash gift is generally equal to the amount of cash donated less the value of any goods or services received in return. And while the benefit of a cash donation is its simplicity, as you will see below, it is not always optimal from a tax and gifting perspective.

Donor-Advised Fund

A Donor-Advised Fund (DAF) is a charitable fund, a 501(c)(3) entity in and of itself, that allows an individual to donate cash or appreciated securities, such as individual stocks, bonds, mutual funds, or exchange-traded funds (ETFs).[2]

Donor Advised Fund DAF Charitable Intentions White Paper

Donating appreciated securities can be a more tax advantageous way to fund a DAF, as donating an investment that has gone up in value generally provides the exact same tax deduction as donating cash, while at the same time provides the extra benefit of eliminating the capital gains tax that a taxpayer would normally pay upon selling the security.

How does it work? The donor makes an irrevocable gift of cash or appreciated securities to a DAF. The donor is then able to decide, on their own timeline, when to grant funds out of the DAF and directly to a charity or charities of their choice. If the contribution is appreciated securities, the DAF is allowed to sell these positions tax-free. The DAF will typically then, at the donor’s discretion, invest the funds in a manner consistent with the donor’s charitable goals and objectives. Once the donor is ready to make a grant from the DAF, he or she simply informs and authorizes the DAF custodian (usually via the custodian’s online platform) to send a check directly to the charity on the donor’s behalf.

Typically, the funding and operational costs of DAFs are low, and our clients also love that they provide a year-end summary report, eliminating the hassle and stress of tracking each contribution/grant out of the DAF individually.

Towerpoint Tip:

At Towerpoint Wealth, we also evaluate “frontloading” a DAF with several years’ worth of potential charitable contributions, allowing a taxpayer to “hurdle” the standard deduction and thus, not only eliminate the future capital gains tax of the donated funds, but also provide them with at least a partial tax deduction for their charitable contributions in a particular tax year.

Private Foundation

A private foundation is a 501(c)(3) organization set up solely for charitable purposes.

A private foundation may be structured either as a corporation managed by a board of directors, or as a trust managed by trustees. Unlike a public charity, the funding for a private foundation typically comes from a single individual, family, or corporation.

The primary benefit of a private foundation is the enhanced control that it provides, as it is able to formulate its own customized charitable gifting approach and platform (and continue to gift directly to other charities as well). A donation to a private foundation is an irrevocable charitable gift, and qualifies for a potential income tax deduction that, for most individuals, will be the exact same as gifting directly to another 501(c)(3) charity.[3]

Importantly, private foundations have administrative and tax reporting requirements that may be costly, and speaking further with a financial advisor and tax professional regarding the benefits and drawbacks of establishing one is recommended.

IRA Qualified Charitable Distribution

Individuals who are over the age of 72 are subject to annual required minimum distributions (RMDs) from their pre-tax IRA(s). These distributions are included on an individual’s tax return as taxable income and are subject to ordinary income tax.

As an alternative to taking a “normal” RMD, an individual can instead execute a Qualified Charitable Distribution (QCD), which allows them to both satisfy their RMD and their charitable intention at the same time.

How does a QCD work? Instead of a “normal” RMD, which usually is deposited into an individual’s checking, savings, or brokerage account, a QCD is paid directly from the IRA to a qualified charity. This distribution not only offsets – or, depending on the amount, fully satisfies – an individual’s RMD, but it is also excluded from taxable income.[4]

And unlike other gifting strategies, a QCD’s net effect as an “above the line” dollar-for-dollar tax deduction can offer additional economic benefits when compared to a “typical” itemized charitable tax deduction.

Charitable Remainder Trust

A charitable remainder trust (CRT) allows a donor to make a future charitable gift, while at the same time, receive an income stream during their lifetime for their own spending goals and needs. There are two types of CRTs: Charitable Remainder Annuity Trusts (CRATs) and Charitable Remainder Unitrusts (CRUTs). The two main differences are how the annual distribution to the income beneficiary(ies) is calculated and how often assets can be contributed to the trusts.[5]

When the donor establishes and contributes to a CRT, they are entitled to a current income tax deduction that is equal to the future expected value of the trust assets that will ultimately pass to the charitable beneficiary(ies). The deduction calculation is based on a number of different factors, such as the annual income stream payout set by the CRT, the age(s) of the income beneficiary(ies), the trust’s specified term of years, and the published IRS monthly interest rate.

At either 1.) the donor’s death, 2.) the death of the beneficiary, or 3.) the completion of the trust’s term, the trustee will distribute the balance of the trust assets directly to the chosen charity(ies).

The primary benefit of a CRT is that an individual may receive a substantial tax deduction in the year they open and fund the CRT, while at the same time, continue to receive income for themselves (or other income beneficiaries) during their lifetime. If the CRT is funded with cash, the donor can claim a deduction of up to 60% of adjusted gross income (AGI); if appreciated assets are used to fund the trust, up to 30% of their AGI may be deducted. In addition, if the trustee decides to sell contributed appreciated securities, he or she can do so tax-free.

Towerpoint Tip:

Opening, funding, and administrating a CRT is complicated and there are important ongoing tax filing obligations. As such, it is highly recommended to work with a trusted financial advisor and tax professional to ensure that a CRT is the right choice. Further, the tax deduction calculation may be audited, so it is important to hire a qualified professional to appraise this value.

Charitable Lead Trust

In the simplest sense, a charitable lead trust (CLT) is the reverse of a CRT. The income generated by the contributed assets is distributed to the chosen charity, and the beneficiaries receive the remainder interest. Like a CRT, a CLT can be an annuity trust (CLAT) or a unitrust (CLUT), but different distribution rules apply.

There are two main types of CLTs: a grantor CLT and a non-grantor CLT. A grantor CLT, like a CRT, is designed to give the donor an upfront charitable income tax deduction. However, to receive the charitable deduction, the donor must be willing to be taxed on all trust income. Since the gift is “for the use of” a charity instead of “to” a charity, cash contributions to a grantor CLT are subject to reduced deduction limits of 30% of AGI, and appreciated asset contributions are subject to deduction limits of 20% of AGI. For non-grantor CLTs, the grantor does not receive a charitable income tax deduction, nor are they taxed on the income of the trust. Instead, the trust pays tax on the income, and the trust claims a charitable deduction for the amounts it pays to the charity. It is very important to note that since they are not tax-exempt, neither type of CLT offers the ability to avoid or defer tax on the sale of appreciated assets like a CRT does.

A CLT may be a better option than a CRT if an individual has no need for current income and wants to ensure that, upon their death, their loved ones receive an inheritance.

Towerpoint Tip:

A charitable lead trust is often structured to provide gift-tax benefits, not necessarily a current income tax deduction. A donor is able to gift more to family members with a reduced gift-tax effect because the gift’s present value is discounted by the calculated income to be paid to the charity(ies). The tax deduction the individual receives is based on the annual amount provided to the charity.

Pooled-Income Fund

A Pooled-Income Fund (PIF) is a type of charitable trust that functions like a mutual fund.

A PIF is comprised of assets from many different donors, pooled and invested together. Each donor is assigned units in the fund that reflect his or her share of the fund’s total assets. Each year, the donors are paid their proportionate share of the net income earned by the fund – the distribution amount depends on the fund’s performance and, importantly, is taxable income to the beneficiary (which is typically the donor but may also be a family member, friend, etc.). At the death of each income beneficiary, the charity receives an amount equal to that donor’s share in the fund.

PIF contributions provide a tax deduction to the donor upon contribution and, like the other charitable gifting vehicles described previously, affords the donor the ability to avoid paying any capital gains taxes on the contributed appreciated securities.

Pooled Income Fund Donor Charity

A primary drawback of a PIF is that the donor has no control over how the assets are invested, as the investment of the fund is directed by a professional manager. As such, it is important that individuals speak with a financial advisor to ensure that a PIF is thoughtfully incorporated into their overall investment allocation and strategy, as well as philanthropic and charitable giving plan.

How can we help?

At Towerpoint Wealth, we are a legal fiduciary to you, and embrace the professional obligation we have to work 100% in your best interests. If you would like to learn more about charitable giving strategies, we encourage you to contact us to open an objective dialogue.

Steve: 916-405-9166,
Matt: 916-405-9164,

[1] In order for an individual to receive a tax deduction, their combined itemized deductions must exceed their standard deduction.

[2] Appreciated securities may be donated directly to certain charities as well. However, doing so is typically an administrative hassle for both the individual and the receiving organization.

[3] Donations to a private foundation are tax deductible up to 30% of adjusted gross income (AGI) for cash, and up to 20% of AGI for appreciated securities, with a five-year carry forward

[4] Up to an annual maximum of $100,000, per taxpayer.

[5] A CRAT pays a fixed percentage (at least 5%) of the trust’s initial value every year until the trust terminates. The donor cannot make additional contributions to a CRAT after the initial contribution. A CRUT, by contrast, pays a fixed percentage (at least 5%) of the trust’s value as determined annually. A donor can make additional contributions to a CRUT.

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Is Your 401(k) in Disarray 03.29.2021

As a small business owner, we know that you are an “around the clock” grinder, with a myriad of responsibilities that often supersede the core responsibilities you have to the growth of your business. And understanding that a regular review of your business’s retirement plan may not be a top priority of yours, at Towerpoint Wealth we have created this 401(k) “healthcheck” for your benefit. We regularly come across 401(k) and other company-sponsored retirement plans that, as currently structured, are in serious need of attention and improvement, and we are experienced in helping you, as a trustee and fiduciary to your company’s retirement plan, minimize the hassle of giving your plan the attention it needs.

Is your 401(k) plan structured and optimized properly to help you and your employees maximize the myriad of economic, investment, and tax benefits? Are you properly managing your fiduciary responsibility? Ask yourself the questions found below to quickly gauge whether your 401(k) needs adjusting or improving.

 Does my plan have a safe harbor structure?

You want to ensure that your 401K) retirement plan passes the annual non-discrimination testing conducted by the IRS. In its simplest sense, non-discrimination testing ensures that an employer is making contributions to each employee’s retirement account that equals the same percentage of salary for everyone. Importantly, if a plan fails a non-discrimination test, the 401(k) may lose its tax-qualified status.1

Retirement Plan 401(k) Disarray Towerpoint Wealth White paper 2021

[1]The most common reason a 401(k) plan fails this non-discrimination testing is when one or more of the business owners make much greater 401(k) contributions compared to their employees.

A safe harbor 401(k) plan structure ensures that you meet the non-discrimination regulatory requirements by following strict guidelines specific-to employer plan contributions, participant disclosures, and much more. 

Does my plan have a profit-sharing component and if so, am I optimizing its structure?

For a business owner to maximize the personal net worth building benefits associated with sponsoring a company retirement plan and receive the maximum 401(k) annual contribution amount of $58,000 in 2021[1] (employee deferrals + employer contributions), pairing a profitsharing component in the plan’s design is essential.

All profit sharing plan structures – same dollar amount, comptocomp, new comparability, etc.[2] – are not created equal. In particular, the new comparability strategy is becoming increasingly more common in modern 401(k) plans as this type of profit-sharing plan allows for unique flexibility in allocating the profits among the business owner(s) and employees.

Is my investment fund lineup optimized?

401(k) investment fund lineups vary from basic to advanced and passive to active. And with employees having better and more diverse investment options outside of 401(k) plans, annually reviewing your company’s fund lineup for improvements is critical to ensure that employees do not look to invest their hard-earned dollars elsewhere, and also to meet your fiduciary responsibility as plan trustee.

It is also a requirement that a business owner (usually with help from an investment professional) formulate, and review at least annually, an investment policy statement (IPS) for their 401(k).

Is my ERISA fidelity bond fund amount appropriate?  

The Employee Retirement Income Security Act (ERISA) requires 401(k) plans to hold a fidelity bond, which protects the plan from losses resulting from improper handling of the funds.

While fidelity bonds are generally inexpensive for the coverage offered, we often see the amount protected as either 1.) inadequate or 2.) overkill.  

[1] Increased to $64,500 for business owners 50 years of age or older.

[2] There are often several different terms that refer to the exact same type of profit-sharing structure.

Does my plan currently allow for after-tax Roth contributions?

While changing for the better, many 401(k) plans still do not allow after-tax Roth contributions. 

For business owners and employees that are in a temporarily low income tax bracket –  a business owner “winding down” and closing in on retirement or a younger employee at the beginning of their career and earning curve – offering an after-tax Roth contribution option, particularly given it typically costs nothing to do so, is a valuable and often overlooked plan benefit.

Is my vesting schedule appropriate?

Retirement Plan 401(k) Disarray Towerpoint Wealth White paper 2021

In order to incentivize employees to stay with your company, having a vesting schedule for any  employer-matching profit sharing contributions that is not overly generous is important. For a number of Towerpoint Wealth’s clients who are business owners, a vesting schedule of six years (with 0% vesting in the first year of participation) is appropriate, but each business and retirement plan is unique.

Have I considered automatically distributing an employee’s 401(k) balance when they leave the company?

Many 401(k) plan administrators charge their fees based on the number of employees that the plan has. 

In order to keep fees to a minimum, it is advisable to consider automatically distributing account balances below a certain threshold when an employee separates from service.

Am I managing my fiduciary responsibility and minimizing my fiduciary liability?

All business owners who offer a 401(k) for themselves and their employees have a fiduciary responsibility to ensure that they are acting in the employees’ best interests, being prudent, diversifying plan investment assets, and adhering to all provisions of the retirement plan documents.

There are concrete steps that a business owner can take to uphold their fiduciary duty and at the same time, minimize their fiduciary liability.

Retirement Plan 401(k) Disarray Towerpoint Wealth White paper 2021

Wealth management firms that specialize in helping business owners optimize their retirement plans, such as Towerpoint Wealth, are able to help guide you through these murky waters.

Am I doing everything I can to maximize my own personal net worth within my company’s retirement plan?

Even if a small business owner has a well-structured plan that meets everyone’s needs, is it important to remember that 401(k)s, and other types of company-sponsored retirement plans, are uniquely customizable. And often, there are overlooked plan features that may help the business owner maximize their ability to accumulate wealth within the plan. 

One of these particularly powerful features is allowing for after-tax deferrals (not the same as after-tax Roth deferrals), which then affords the business owner to take advantage of the “Mega Backdoor” Roth IRA strategy.

Some other questions that are worth your thoughtful attention: Do I allow for hardship distributions and if not, should I? What about allowing rollovers from other retirement plans? Is it risky to offer loans to employees? Are my plan’s expenses and fees reasonable?

How Can We Help?

Steve Pitchford, CPA, CFP®
Director of Tax and Financial Planning

At Towerpoint Wealth, we are a legal fiduciary to you, and specialize in optimizing retirement plan structures for business owners.. If you would like to speak with us regarding any other tax questions you may have, we encourage you to call (916-405-9166) or email ( to open an objective dialogue.

Towerpoint Wealth, LLC is a Registered Investment Adviser. This material is solely for informational purposes. Advisory services are only offered to clients or prospective clients where Towerpoint Wealth, LLC and its representatives are properly licensed or exempt from licensure. Past performance is no guarantee of future returns. Investing involves risk and possible loss of principal capital. No advice may be rendered by Towerpoint Wealth, LLC unless a client service agreement is in place.

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The Frustrations of Form 1099 : TPW White paper 03.08.2021

It’s Tax Time | What is the Form 1099?

What exactly is a Form 1099, why can they be so frustrating to process, and how do you manage the problem of receiving an amended one? Read on to find out!

What is the Form 1099?
A Form 1099 is any one of a series of documents that contains information on all transactions that occurred inside of a “taxable” account1 during a given tax year. Reporting this information on a taxpayer’s annual federal individual income tax return is required. Most investment custodians (e.g. Charles Schwab, Fidelity, Merrill Lynch, etc.) will consolidate the various Form 1099s into one consolidated document, known as a Composite Form 1099.

The most common transactions represented on a Form 1099 are:

• Dividends and Distributions (Form 1099-DIV): Typically generated by owning a stock/equity investment product.
• Interest Income
(Form 1099-INT): Typically generated by owning a bond/fixed-income investment product.
• Capital Transactions (Form 1099-B): Reflects gains/(losses) from the sale of a capital asset.

Towerpoint Tip:

A Form 1099 is not the same as a Form 1099-R. The latter form reports annual distributions from tax-advantaged retirement accounts, such as “regular” pre-tax IRAs, Roth IRAs, SEP IRAs, and 401(k)s.

What do I do with a Form 1099?

If you work with a CPA/tax advisor, you should provide this tax form to them for inclusion on your federal individual income tax return.

If you prepare your own tax returns, be sure to utilize the import function that many tax preparation software programs now provide. This will ensure accurate reporting to the IRS, which is particularly important for Form 1099s, as any reporting discrepancies in the information you input versus the information the Internal Revenue Service (IRS) receives from your custodian automatically “flags” your federal tax return for additional scrutiny.

Why do I receive my Form 1099 late or even worse, receive an amended Form 1099?

Generally, investment custodians have until February 15 to provide taxpayers with their Form 1099s, although more recently, custodians are requesting exceptions and extensions to, or even flat-out missing, this issuance deadline, so be aware that you may be waiting past this date to receive yours.

Why? Before completing Form 1099s, custodians must first receive and collect taxable income information from each of the underlying investments all of their clients were invested in during the prior year; and more often than not, 1099 issuance delays originate with the underlying companies themselves.

It is also common for custodians to have to restate the originally issued Form 1099, and reissue what are known as amended Form 1099s, when one or more of the underlying investment companies revise, update, or correct an error made in their initial reporting.

What do I do if I receive an amended Form 1099, and are there any steps I can take to make this less of a headache?

if you receive an amended Form 1099 after already filing your tax return, you may need to file an amended tax return. You should speak with your CPA/tax professional for guidance on this important consideration.

To put yourself in the best position to avoid this hassle, we recommend that taxpayers work with their CPA/tax professional to prepare their tax returns in full as early as possible in the filing season, but wait until later in March to actually file them. While we fully understand the desire for some of you to finish and file your tax return as soon as possible, waiting to file minimizes the likelihood that you’ll have to file an amended tax return after receiving an amended Form 1099. Additionally, this gives your tax professional adequate time to properly prepare and file your return should you receive amended 1099s.

Towerpoint Tip:

If the difference between the original Form 1099 and the amended Form 1099 is slight, and can be considered in your favor, the cost of amending the tax returns may outweigh doing nothing. However, we advise you file an amended return when the amended Form 1099 results in additional taxes owed.

How Can We Help?

Steve Pitchford, CPA, CFP®
Director of Tax and Financial Planning

At Towerpoint Wealth, we are a legal fiduciary to you, and embrace the professional obligation we have to work 100% in your best interests. If you would like to speak with us regarding any other tax questions you may have, we encourage you to call (916-405-9166) or email ( to open an objective dialogue.

Towerpoint Wealth, LLC is a Registered Investment Adviser. This material is solely for informational purposes. Advisory services are only offered to clients or prospective clients where Towerpoint Wealth, LLC and its representatives are properly licensed or exempt from licensure. Past performance is no guarantee of future returns. Investing involves risk and possible loss of principal capital. No advice may be rendered by Towerpoint Wealth, LLC unless a client service agreement is in place.

Matt Regan No Comments

Comprehensive Estate Planning | TPW White paper 03.08.2021

Navigating the Tax Laws to Maximize | Your Beneficiary’s Inheritance | Comprehensive Estate Planning

When most individuals are establishing an estate plan, they generally only think about the tax consequences to themselves. But a truly comprehensive estate plan is one that takes planning a step further and considers the tax consequences the beneficiaries of the estate may face. When creating an estate plan, having a clear understanding of, and properly planning for these taxes will help ensure your beneficiaries get the largest inheritance possible.

When one inherits money as a beneficiary of an estate, there are three different taxes that oftentimes need to be understood and accounted for:

Let’s take a look at these individually:

Estate and Gift Tax

• The 2021 federal estate tax exemption (commonly known as the unified tax credit) amount is $11,700,000 per individual.
• Only the deceased taxpayer is subject to the estate tax when the estate value is greater than the unused exemption.
• Even if the decedent did not have a taxable estate, the estate of the decedent survived by a spouse should file Form 706, Estate Tax Return, to pass any remaining/unused unified tax credit exemption to the surviving spouse.
• When someone dies, their assets become property of their estate. Any income those assets generate is also part of the estate, and may trigger a requirement to file Form 1041, Income Tax Return for Estates and Trusts.
• An inheritance is not considered taxable income to the beneficiary.
• Currently, in addition to estate taxes assessed at the Federal level, 12 states and the District of Columbia also collect an estate tax. California does not currently have an estate tax.

Inheritance Tax

• Only six states currently collect this tax (Iowa, Kentucky,Maryland, Nebraska, New Jersey, and Pennsylvania).
• Property passing to a surviving spouse is exempt from inheritance taxes in all six of these states.

Income Tax

• Inherited retirement account distributions are subject to ordinary income taxes.
• If you sell or dispose of inherited property that is a capital asset, you will be subject to either a long-term capital gain or loss, regardless of how long you, as the beneficiary, have held the asset.

Additional considerations

Inherited Pre-Tax Retirement Accounts

• Eligible Designated Beneficiaries and Non-Eligible Designated Beneficiaries are subject to different required distribution rules.
• Consider Roth conversions to allow the beneficiaries to take tax-free distributions.

Lowering the Value of Your Estate – Gifting

• Make annual cash gifts to your children, grandchildren, other family members, and even friends. You can also contribute cash to a 529 plan to help pay for future school to any individual you would like. The receipt of cash is non-taxable to the recipient, and, if the gift is below the $15,000 annual exclusion amount, you will not eat into your above-mentioned $11,700,000 lifetime estate and gift tax exemption amount.

Lowering the Value of Your Estate – Philanthropy

• If you are charitably inclined, you can make gifts of any size at any time while alive directly to charities or to a Donor Advised Fund. The donation of appreciated securities provides not only an immediate deduction of the fair market value of the stock at the time of contribution, but also avoids capital gains tax upon sale.
• Charitable contributions due to the death of the taxpayer result in a dollar for dollar reduction of the taxable estate.
• Additional vehicles available include Charitable Remainder Trusts or Charitable Lead Trusts.

Life Insurance

• If you are considering buying life insurance to either pay for the estate tax liability or provide more for your beneficiaries, set up a life insurance trust and have it purchase the policy so the death benefit isn’t included in your taxable estate.

Step-Up in Cost Basis – Take Advantage!

If you have appreciated stock or property and gift it to someone, the recipient gets the carried over basis and will have to pay capital gains when he or she sells the asset. Instead of gifting before your death, have them inherit it after your passing so they get a “step up” in basis and recognize a smaller gain on future disposition.

The Future of Estate Taxes Under the Biden Administration

• During his campaign, President Biden discussed the possibility of decreasing an individual’s federal estate tax exemption amount either to $5 million per individual (and $10 million for a married couple) or to the pre-Tax Cuts and Jobs Act amount of$3.5 million per individual (and $7 million for a married couple). This decrease in lifetime exemption could be paired with an increased top tax rate of 45 percent.
• President Biden also proposed eliminating stepped-up basis on death and possibly taxing unrealized capital gains at death at the proposed increased capital gains tax rates.

How Can We Help?

At Towerpoint Wealth, we are a legal fiduciary to you, and embrace the professional obligation we have to work 100% in your best interests. If you would like to learn more about Towerpoint Wealth and how we can help you achieve your financial goals, we encourage you to call (916-405-9164) or email ( to open an objective dialogue.

Steve Pitchford No Comments

Strategies to Own a Concentrated Stock?

Own a Concentrated Stock Position? Our 5 Strategies to Help Manage Risk and Taxes

Stock compensation can be a wonderful complement to a traditional compensation package, oftentimes contributing significantly to an investor’s net worth. However, there is an overlying risk to investors who have too much of their net worth concentrated in the stock of one company. This is more complicated if this stock has appreciated to an extent that selling would result in a substantial capital gains tax liability.

How can an investor mitigate the risk of having too much of their net worth concentrated in a single appreciated stock, and avoid significant tax liabilities? 

Multiyear-Sales Strategy 

Some investors may feel that the solution to owning an overconcentration of stock in a single company is simple: sell all of the stock and reinvest the proceeds in a diversified portfolio. While this strategy has the obvious benefit of immediately eliminating the overconcentration risk, the tax “hit” of utilizing this strategy can be substantial – especially considering that investors who received the stock as compensation may have a very low (or no) cost basis in it.

One approach to mitigate the tax impact of these stock sales is to amortize them over a period of two or three years. While this will not reduce an investor’s risk exposure as quickly as an outright sale, this strategy has the advantage of spreading the capital gains taxes over a multiyear period – allowing an investor to better control the timing of the capital gains with the goal of realizing more of these gains in relatively low tax years.  

 Put Option or Protective Equity Collar

A put option gives an investor the right to sell a stock at an agreed upon price on or before a particular date. The advantage of owning a put option is that it establishes a “floor” price at which the investor will be able to sell a stock position. This greatly reduces an investor’s downside risk, while at the same time allows them to retain the unlimited upside.

Instead of paying “out-of-pocket” to cover the premium (cost) of the put option, an investor can simultaneously sell a call option, which gives the purchaser of the call option the right to buy the stock at an agreed upon price on or before a particular date.

The strategy of simultaneously buying a put option and selling a call option is known as a protective equity collar. The potential drawback of an equity collar is the investor is now limited on the upside of the stock price as well. However, understanding that the premium from selling a call option will often cover the entire premium to purchase the put option, an equity collar can be a low-cost approach to hedging a concentrated stock position. Buying and selling options is best handled by a financial professional working on your behalf. 

Pool Shares into an Exchange Fund 

Exchange funds are private placement partnerships where an investor contributes a concentrated stock position into a fund that includes a mix of other stock positions. Oftentimes, these other stocks were donated by investors that had the same intent of diversifying their own appreciated stock positions.

With exchange funds, each investor receives a pro-rata share of the partnership (measured in units) based on the value of the stock that they contributed.

While one obvious advantage of an exchange fund is immediate diversification, an additional appeal of this strategy is that capital gains taxes are deferred until the investor sells their fund units. 

There are several important disadvantages of exchange funds, such as the typically high fund management fees, the lack of control over the other stock positions in the fund, and the lock-up period before an investor can sell their units (which is often as high as seven years). Further, exchange funds are regulated private placements, so they are typically subject to investment minimums and only available to investors that meet certain net worth thresholds.

Variable Prepaid Forward Contract

A Variable Prepaid Forward (VPF) contract is an agreement that an investor will sell a specific number of shares at a discount (usually between 75-90%) at a pre-specified future date in return for an upfront cash payment.

The “variable” in the term VPF refers to the fact that the shares the investor is selling at a future date are not fixed and are dependent on the performance of the stock. A lower stock price results in more shares sold to satisfy the obligation and a higher stock price results in fewer shares sold.

The benefit of a VPF contract is the immediate liquidity received from the cash advance. In addition, the use of the VPF contract allows for the deferral of capital gains – as the variability of the shares to be sold means that a VPF contract is not deemed a constructive sale by the IRS until the shares are delivered. However, in order to avoid IRS scrutiny, a VPF contract should be drafted by a qualified tax professional or lawyer. 

Charitable Gifting

While charitable gifting is a broad category that requires further in-depth discussion, there are several charitable gifting strategies an investor can utilize to reduce the risk of an overconcentrated stock position.

The simplest strategy is for an investor to donate the overconcentrated stock position to a charity (or charities) of their choice. Not only will an investor generally receive the same exact 

tax deduction as if they donated cash, donating stock has the dual benefit of eliminating the capital gains tax that would be associated with selling the stock outright. 

In our view, donating stock is a great way for an investor to both reduce their concentrated stock position and fulfill their charitable intentions.

Pairing this with a Donor-Advised Fund (DAF), a charitable investment account, can streamline the process of gifting stock and has the added benefit of allowing an investor to control the timing of both their tax deductions and their donations.

There are also different charitable trusts that may be appropriate for an investor with an overconcentrated stock position. These types of trusts, which include a Charitable Remainder Trust (CRT) and Charitable Lead Trust (CLT), allow an investor to better control and customize the charitable strategy that works best for them.

Charitable trusts come with material costs and added complexity, and we recommend you work with an experienced estate planning attorney and your financial advisor to determine the best choice for you.

How Can We Help?

At Towerpoint Wealth, we are a fiduciary to you, and embrace the legal obligation we have to work 100% in your best interests. We are here to advise you, and will work with you to decide the optimal strategy for your concentrated stock position. 

If you would like to discuss further, we  encourage you to call, 916-405-9166, or email to open an objective dialogue.

Steve Pitchford No Comments

IRS Scams: The Big Six of the Dirty Dozen

Each year, the Internal Revenue Service (IRS) releases an annual report known as the “Dirty Dozen.” The report highlights the most commonly practiced tax scams that the IRS identifies each year. Which of these current and past scams should you be most worried about? We have identified six worth keeping a special eye on.

1) Phishing

Phishing is the process of an individual or organization illegally trying to collect your sensitive information (personal, financial, etc.). 

According to the IRS website, common phishing schemes center around fraudsters impersonating the IRS via email, regular mail, telephone, text messages, or even social media.

As a matter of policy, the IRS does not contact taxpayers by email, text message, or social media.

What should you be on the lookout for to identify phishing? Fraudsters…

  • Claiming that they are with the IRS and are missing some of your financial or personal information to process your tax returns
  • Stating that suspicious activity has been detected on your online IRS account
  • Asking you to click a link to finalize a tax payment
  • Offering a tax refund         

2) Identity Theft

Tax season is a dream time of year for fraudsters. 

Once a taxpayer has become the victim of phishing, a common next step for the fraudster is to file a tax return in their victim’s name early in the filing season to receive a sizable tax refund. The biggest challenge with tax refund identity theft is that the taxpayer likely won’t even realize the occurrence until they try to file their return. At which point, the IRS will “flag” the return and mail the taxpayer a 5071C letter to verify their identity.

The first step to prevent identity theft is to diligently protect your personal and financial information. Be wary of the phishing tactics described above, and also be cautious when providing businesses and individuals with your social security number. In addition, you should file for my Social Security” online, install antivirus and firewalls on your computer, change passwords on online accounts frequently, review your credit report for suspicious activity, and most importantly, use common sense.

If you are concerned that you were subject to identify theft, immediately inform your CPA/tax professional, your financial advisor, your bank, the Social Security Administration, and the IRS.

3) Fake Charities

Fraudsters know that using a fake charity to solicit contributions from unwitting victims has a history of past success.

Be cautious if you notice that a charity’s name is similar to, but not the same as, well-known charitable organizations.

Vetting a charity before you contribute to it is always a smart idea. One way to do so is by visiting Charity Navigator and searching for a charity to ensure that it’s legitimate. 

4) Inflated Refund Claims

While most CPA/tax professional firms are reputable and trustworthy operations, there are those out there established for the sole purpose of stealing your money by offering inflated refunds.

If you find a firm advertising, and often guaranteeing, a sizable refund, don’t just be skeptical, run the other direction! The refund is often simply incentivizing you to provide the fraudster with your personal and financial information, so they can then use this information to file for this refund on their own.

A firm offering to be compensated by a percentage of the refund is just another variant of this strategy.

5) Falsified Income for Credit Claims and Padded Expenses

The IRS regularly analyzes tax returns to check for income that is inflated (to allow for a refundable tax credit claim) and to ensure that expenses are not exaggerated.

Always be sure to review your tax return prior to submission for inflated income, falsified deductions, and padded expenses.

If you believe you were a victim of a falsified income for credit claim or padded expenses fraud, you should immediately file Form 3946-A with the IRS.

6) Tax Return Preparer Fraud

Tax return preparer fraud is the overarching theme of this white paper and encompasses all sections above.

It’s important to remember that you are the one who is ultimately responsible for your tax return.

And while you may have a CPA/tax professional preparing your return, it pays to have at least baseline knowledge of taxes to be able to identify when a tax preparer is not working in your best interest.

It’s also prudent to review your tax returns before you sign. If reviewing your taxes is confusing or overwhelming, you can often find low-cost help. Check your local resources for libraries and community centers to see if they have tax preparation volunteers.

How Can We Help?

At Towerpoint Wealth, we are a legal fiduciary to you, and embrace the professional obligation we have to work 100% in your best interests. If you would like to discuss your circumstances further, we encourage you to call (916-405-9166) or email ( to open an objective dialogue.

Matt Regan No Comments

Attorney’s Guide to Building and Protecting Personal Net Worth

A Ben Franklin Redux – Build Net Worth

Remember how you felt the day you said “I passed the bar!”?

That day, you no doubt celebrated your great accomplishment. It marked not only the closing chapter of your law school career, but the opening of an important new chapter in your personal and professional life, one with tremendous economic upside if properly harnessed.

In his essay Advice to a Young Tradesman, Benjamin Franklin famously states, “Time is money.” This phrase, which he wrote in 1748, still rings true today, especially for busy attorneys and law-firm partners like yourself, who earn a living primarily from billable hours.

As the numbers increase on your net worth statement, so does the responsibility of managing them correctly. As you accumulate wealth, have you achieved economic peace of mind? Not having the time, expertise, or patience, to establish and execute on a customized wealth-building and retirement strategy is neither a failing nor a flaw – it is a very common problem. 

Finding an expert, trustworthy partner to help you manage and coordinate much of this “financial heavy lifting” can lead you closer to  the economic peace of mind you have been working so long and hard for.

Emotional Awareness – Your Strength and Your Weakness?

As a successful attorney, you are committed and laser focused on helping your clients, managing and collaborating with colleagues, and balancing the administrative obligations of running your practice.

You are working to strike the appropriate balance between your career and your family life. It is challenging — and stressful — to  properly coordinate all of this. Consider too, that you have a responsibility to develop and execute on a well-thought-out and disciplined plan to grow and protect your personal wealth. It’s no wonder this task often gets back-burnered until you “aren’t so busy.” 

Unfortunately, for many lawyers, “not so busy” only becomes a reality once retirement does, and by that time, many critical economic decisions, key financial and investment planning opportunities, and basic compounding benefits have come and gone.

Get Help, and Don’t Get Burned!

If you haven’t yet hired a professional to help, it might be because you’ve heard about uninspiring, unsettling, or even outright illicit experiences with so-called “financial-advisors.” Certainly, what tends to be the most challenging aspect of hiring an advisor is finding one who cultivates your trust.

An important part of the wealth building journey is partnering with the right financial advisor. The first step you can take is to ask friends and colleagues to share their successful experiences with advisors. The advisor is providing a service that will have a lasting impact on your financial future, so you need to be sure you are hiring the right person to meet your specific goals.

Your advisor will need to know every single aspect of your financial life, and oftentimes many aspects of your personal life as well, in order to provide the most appropriate advice and customized solutions. Each member of your family, especially your significant other, must have confidence the advisor will always hold your family’s best interests above their own. Because most attorneys have uneven cash flow throughout the year, complicated tax issues, and complex retirements, your advisor will be able to best serve you when they have a strong understanding of how you are compensated and the complexities of it.  These things that make financial planning difficult for you, are well inside a fiduciary advisor’s wheelhouse.

“Suitable” versus “Fiduciary”

A second extremely important step when searching for an advisor is to assure they are bound to a legal fiduciary standard. As a legal fiduciary, a financial advisor is typically regulated by the Securities and Exchange Commission (SEC), and is legally held to the highest standard in the industry, the fiduciary standard. They are required to discharge their planning, counsel, and advice solely in the best interests of the client, even if it means placing the client’s interests ahead of the advisor’s.

Starkly contrasting the fiduciary standard and obligation is suitability standard, which simply requires a financial advisor to make recommendations that are “suitable” for a client.  Importantly, the suitability standard does not legally require an advisor to act solely in a client’s best interests. Another significant distinction between these two very different professional standards is how an advisor is compensated. A fiduciary advisor’s compensation generally is via an annual, asset-based fee, computed based on a percentage of the client’s assets under management. A financial advisor who is not a fiduciary oftentimes receives hidden compensation from products with higher fees and lower returns that they’ve steered you into.  Recently, theWhite House Council on Economic Advisers found that non-fiduciary advice costs investors $17 billion a year! And, as Franklin said in his aforementioned essay: 

“You will discover howsmall, trifling expenses mount up to large sums, and will discern what might have been…saved.”

With a commission-based compensation structure, there is the possibility for conflicts of interest.  If a prospective advisor is not 100% transparent about how he or she answers the question, “How do you get paid?” look elsewhere. A true fiduciary will be quick to point out how, and wherefrom, they derive professional compensation for their time, service, and planning. How do I know if a financial advisor is a legal fiduciary? 

The simple answer – ask! You will quickly find out which standard a prospective financial advisor adheres to when you ask:

“As my prospective financial advisor, would you be a legal fiduciary to me, and are you willing to attest to that in writing?”


What Can I Expect From a Good Financial Advisor? 

Because every individual has a unique set of personal and financial circumstances, it is a crucial first step for your financial advisor to help you determine and set your financial goals. Sounds easy, right? Maybe — until you seriously consider your responses to the following questions:

  • What money concerns keep you up at night, and how would you like me to work with you so you can rest soundly? 
  • What are you doing now, and what do you want to accomplish in life?
  • What decline in your overall investment portfolio, in hard dollars, would cause you great personal discomfort such as lack of sleep, anxiety, worry, or even despair?
  • Why do you think you need financial help and guidance?
  • What changes do you expect to occur in the future?
  • How do you picture your ideal life five years from now? Ten? Fifteen?
  • How would you describe the emotions you had about money growing up?
  • What are three financial milestones you hope to accomplish?

By no means all-encompassing, this list of questions is meant to illustrate the depth and sincere interest in you that the right financial advisor will demonstrate during the discovery phase of your relationship. In addition to asking, listening to, and considering your answers to thoughtful questions such as these, any good advisor will dedicate their time and energy to you in order to develop a rapport, and ultimately, trust. 

Investing, coordinating, and managing your wealth and assets is a challenge that increases as your net worth does, and just like in law, where having a good lawyer when entering the courtroom should yield the highest probability of success, the same holds true for wealth management and working with a qualified financial advisor.

Financial Emotional Awareness 

Managing emotions and remaining objective when making financial decisions is an essential component of longer-term success in building, and protecting, one’s wealth. Every day, individuals are bombarded with information that can make them question whether or not they are making the right choices with their finances. A quality, trustworthy financial advisor will help guide you through the noise and protect you from making emotional or irrational decisions to ensure you  stay on your path to financial freedom.

My Lawyer Does the Same Thing…

When working with an attorney, a client should expect to receive custom-tailored planning, advice, and counsel only after a myriad of different possibilities and probabilities about the future have been considered. This construct of a financial advisor-client partnership differs little, as this same process holds true in finance as it does in law.

A quality financial advisor will leverage a broad-based array of resources to provide solutions and advice, much of which you may never have heard of, thought about, or had access to.

They will help you identify your level of acceptable risk, and a target rate of return to be able to meet your personal and economic goals. As is true in the courtroom, there is a direct correlation between taking risk and the potential for obtaining the desired results. The financial relationship between risk and return is inextricable, and needs to be consistently monitored due to the ever-evolving landscape of the economy, politics, the financial markets, and most importantly, your own personal circumstances. Having a professional help you manage this balance between risk and reward increases the probability of your achieving financial success.

Reducing Drag and the “Necessary Evils”

Keeping what you have saved and earned is just as important as growing it. 

Specifically, a good financial advisor will work with you to manage and minimize the two major necessary evils:

  1. Income taxes
  2. Costs/fees/expenses

Understanding almost all financial transactions incorporate a tax and a cost component, your financial advisor and your tax advisor should consistently interface with each other to develop and implement effective tax mitigation strategies to help you keep as much of your hard-earned dollars in your pocket as possible. For most attorneys, current self-employment and income tax rates are high, and will likely only increase in the future. The efficiency of growth in your net worth can be directly affected by lackluster tax planning, not only by the choices you make in how you receive and allocate your ordinary income as you save and invest, but also in how and where you derive investment income. This is especially true when it comes to your 

retirement planning. As you accumulate wealth, it is imperative for your financial and tax advisors to work together to maximize how and where you are making retirement contributions, and how and where to leverage the multitude of tax benefits that are available.

During retirement, as you begin strategic withdrawals from your nest egg, your advisors should regularly analyze not only the sustainability of how much you are taking, but should also weigh  in on how and where to make withdrawals, based largely on your current tax bracket as well as the expected future tax environment. For attorneys fortunate enough to have a retirement pension, an analysis should be done to determine whether it is better to take as a single-life or joint-life annuity or as a lump sum in order to  maximize your net dollars.

Lastly, to enhance the longer-term growth of your wealth, your financial advisor should work with your investment managers to methodically select the right investment vehicles that produce the greatest after-tax returns for both your managed and unmanaged assets. After all, it is not what you make but what you keep that is important. 

Time to Enjoy!

Planning your financial future in addition to all your other professional and personal responsibilities is a daunting task, but you don’t want to wake up one day and ask yourself why your colleagues are retired while you are still working. Being a lawyer is rewarding job, but it can  be very stressful and requires long hours. Thirty or more years of this lifestyle can take quite a toll on the body and mind, and you deserve a rewarding financial future and economic peace of mind. Time is money. Beginning a succinct and custom-tailored wealth management plan now will help you achieve your goals, and ultimately, help you retire on your schedule. Partnering with an advisor that not only understands you, but also the  unique financial challenges that attorneys face, means you may spend less time worrying about this aspect of your life.

You wouldn’t hesitate to hire a legal expert to help you win a case or strengthen a lawsuit, and the same can certainly be said about hiring a financial expert advisor to help you properly coordinate all of your financial affairs and ideally, build economic peace of mind.

How Can We Help?

At Towerpoint Wealth, we are a legal fiduciary to you, and embrace the professional obligation we have to work 100% in your best interests. If you would like to discuss whether a Roth conversion may make sense for you, we encourage you to call (916-405-9164) or email Matt Regan, ( to open an objective dialogue.

Steve Pitchford No Comments

2020: The Perfect Year for a Roth Conversion

While 2020 will rightfully be remembered for the challenging and unprecedented COVID-19 battle we have all been impacted by, at Towerpoint Wealth we have continued to proactively work with clients to identify economic opportunities presented by the coronavirus crisis. Specifically, we have identified a “silver economic lining” tax planning strategy this year, one that is designed to take advantage of today’s low income tax rates, which we feel are temporary, while at the same time leave our clients better positioned for tomorrow’s higher income tax rates, which we feel are inevitable. This white paper will discuss what a “Roth IRA conversion” is, who may benefit from a Roth conversion, why 2020 is a potentially great year to do a Roth conversion, and how to utilize important tax planning tools to evaluate this opportunity.

Roth IRA Conversion

A Roth conversion is a retirement and tax planning strategy whereby a taxpayer “converts” some, or all, of their “regular” pre-tax retirement assets into tax-free Roth retirement assets. It is important to note that ordinary income taxes are owed on the tax-deferred contributions and earnings that are converted.

While the most common Roth conversion strategy is a pre-tax IRA to a Roth IRA, two other popular methods exist:

  1. Convert pre-tax employer-sponsored retirement plan assets (401k, 403b, 457, etc.) to Roth IRA assets (if the taxpayer has separated from service from the employer).
  2. Convert pre-tax 401k assets to Roth 401k assets (if the employer retirement plan allows for an in-plan conversion).

A Roth conversion, when utilized properly, is a powerful tax planning strategy for the following reasons:

• It maximizes the tax-free growth within a taxpayer’s investment portfolio.
• As distributions from Roth retirement accounts are tax-free, a Roth conversion provides a hedge against possible future tax rate increases.
• As Roth IRAs do not have required minimum distributions (RMDs), it reduces taxable RMDs on pre-tax retirement assets that a taxpayer is annually subject to after reaching the age of 72.
• It leaves a greater tax-free financial legacy to heirs.

However, even understanding these benefits, a Roth conversion may not always be in a taxpayer’s best long-term economic interests if:

• The current tax cost of the conversion is prohibitively high. A Roth conversion, in its simplest sense, is a trade-off between paying taxes now vs. paying taxes later. For the strategy to be impactful, the current tax cost of the conversion should not be so expensive that it outweighs the benefit of any expected future tax-free investment growth.
• The taxpayer is making regular and material withdrawals from their pre-tax IRA.
• The taxpayer does not have the cash to pay the tax due on conversion.

Towerpoint Tip:

We recommend converting shares of investment positions rather than selling investments in the IRA and then converting cash proceeds. This ensures that the taxpayer continues to have market exposure during the conversion process, and also saves on the transaction fees that may be levied when selling an investment position.

2020 – A Perfect Year for Roth Conversions?

There are three reasons why we believe 2020 is a great year for Roth conversions:

  1. While no one has enjoyed this year’s market volatility, material intra-year market pullbacks, such as the one we experienced in March, provide a unique opportunity to convert pre-tax investments to Roth IRA at a time when their value is, we believe, temporarily depressed.
    Performing a Roth conversion with these temporarily depressed assets “locks in” the income taxes owed at their lower value upon conversion. While we are humble in recognizing we do not have a crystal ball, we strongly believe that crisis events are temporary, and given time, these assets will recover in value. Thus, this tax strategy results in paying a lower tax price when converting investments to a tax-free Roth IRA.
  2. Understanding the uncertainty surrounding the upcoming Presidential election, and given the government’s need to raise funds to offset its massive 2020 stimulus packages, there is certainly no guarantee that income tax rates will stay this low in future years.
  3. Given that the CARES Act eliminated RMDs for 2020, this is a uniquely low tax year for those taxpayers who are ordinarily subject to RMDs, allowing them to convert a greater amount of assets while remaining in low income tax brackets.

Towerpoint Tip:

At Towerpoint Wealth, pairing a Roth conversion with the “frontloading” of a Donor-Advised Fund (DAF) has been a powerful tax planning strategy, allowing our clients to convert more to tax-free Roth assets at lower tax rates, while also allowing taxpayers who would not ordinarily itemize deductions to “hurdle” the standard deduction – this ensures that they receive at least a partial tax deduction for their charitable contributions.

Executing a Roth conversion

When determining the optimal amount to convert to tax-free Roth assets, there is no “one size fits all” approach.
A taxpayer’s unique personal and financial circumstances should drive the conversion discussion. For one taxpayer, recognizing any amount of conversion income may not make tax or economic sense, while for another, particularly those who want their heirs to inherit assets tax-free, converting a sizeable amount (even at a material tax cost) may be attractive.

One window of time in which we look to help clients aggressively execute a Roth conversion is immediately upon retirement, before they begin filing for Social Security benefits. This is often a uniquely low income-tax window of time, where a taxpayer is still young enough to potentially enjoy many future years of tax-free growth that Roth assets allow.

If a Roth conversion is worth evaluating for a client, many CPAs and tax professionals assemble customized tax projections to optimize the decision-making process.

And while Towerpoint Wealth is not a public accounting firm, we regularly utilize BNA Income Tax Planner, a powerful tax projection software, to assemble Roth conversion tax projections for our clients, in order to streamline collaboration with their CPAs and tax professionals. If our client prepares their own tax returns, we work directly with them to evaluate these Roth conversion scenarios.

Towerpoint Tip:

Under the Tax Cuts and Jobs Act (TCJA), the IRS eliminated the ability to recharacterize (i.e. undo) a Roth conversion after it has been made. For this reason, we generally recommend waiting until closer to the end of a tax year, when taxable income is clearer, prior to executing a Roth conversion. However, in unique tax years such as 2020, we have been strategically executing Roth conversions throughout the year to ensure we are taking advantage of market volatility and pullbacks, while also looking for an opportunity to “top up” the conversion later in the year.

How Can We Help?

At Towerpoint Wealth, we are a legal fiduciary to you, and embrace the professional obligation we have to work 100% in your best interests. If you would like to discuss whether a Roth conversion may make sense for you, we encourage you to call (916-405-9166) or email (, Steve Pitchford, to open an objective dialogue.

Joseph Eschleman No Comments

Digital Security Basics : Working from Home:

Since the start of the COVID-19 pandemic,  millions of workers have begun to work from  home. Before this massive transition to remote work, Americans spent an average of 6.42  hours on the internet every day.  36% of  internet users in the USA between ages 16-64  were using mobile banking or financial services apps every month, and 20% of internet users in the USA between ages 16-64 use mobile payment services every month.i These metrics have likely increased over the last few months, which is a perfect reminder to consider digital security best practices.  

While many assume they are up to speed on basic internet security topics, the chart at the left from Pew Research suggests that there are still significant gaps in common understanding of best practices while working or browsing online. In particular, the chart reveals how a significant percentage of the public is uncertain or uninformed about crucial cybersecurity topics, such as encryption of websites with https://, or two-factor authentication. 

Encrypted Browsing 

Constant internet connectivity is a very useful resource, but it can also make us more vulnerable to a number of risk factors often taken advantage of by malicious actors. Technology also makes everyone more efficient, including cyber criminals. One study found that 64% of Americans have been impacted by some form of data theft.  Following a few basic procedures in your online life can significantly reduce exposure to cyber-attacks. 

Home Network Security

When you first contacted an internet service provider (ISP) to set-up your WiFi and cable, you likely considered the internet speed you needed, what cable channels you wanted, and how much these services would cost. But, once you were connected, did you ask your ISP how to change your router’s default password (not to be confused with your WiFi Password)?

Contact your ISP if you need help configuring any of the above.

Password Best Practices

While configuring your home WiFi, you should have created at least three separate, unique passwords, before creating any passwords for your different devices and applications. According to industry-leading password management firm LastPass, weak or compromised passwords cause approximately 80% of data breaches. Remember to follow the below password basics and avoid reusing the same password across multiple accounts.

Phishing Attacks and Social Engineering

Phishing is a cybercrime in which malicious actors attempt to gain access to sensitive personal data by posing as legitimate organizations or people.

According to the FBI, as of March 30, 2020, their Internet Crime Complaint Center (IC3) has received and reviewed more than 1,200 complaints related to COVID-19 phishing scams alone.iv
Phishing emails are often crafted to appear as if they were sent from health organizations, financial institutions, social media sites, or retailers. Often, phishing emails include suspicious links or attachments that try to trick you into you into taking an action or visiting a website that is against your own best interest.

To stay vigilant against phishing:

Look for spelling and grammar errors both in the content of the email and the sender’s address. However, keep in mind that hackers have also learned how to steal and use legitimate email addresses.

Don’t click on links until you can verify that they lead to a legitimate website. Hovering over a hyperlink in an email with your cursor will reveal the web address where the link leads, before you click through. If you receive an email that appears to be from a known contact (such as a client, friend or company) and you are unsure if the email, a link, or an attachment is authentic, contact the sender by phone or a separate email (don’t just
“reply” or “forward”) to verify.

Never share your email address, passwords, or any other sensitive personal information via email unless you are absolutely certain of the sender’s authenticity and of how the information will be used. Be skeptical of language implying urgency or immediate need. When in doubt, pick up the phone and call to share such personal details for any reason.

Managing Devices

Software Updates: A Pew Research study indicated that more than 50% of smartphone owners update operating systems only when it is convenient and 14% never even bother with updates.v Manufacturers like Apple and Samsung release updates to patch security vulnerabilities, so it’s important to update your software, applications, browsers, and firewall protection to the latest versions available. Consider enabling automatic updates for your convenience.

Protecting the Data on Your Device: Survey results indicate that 28% of smart phone owners do not lock their phones with a Would you leave your home unlocked when you leave for work or an errand? Always lock your devices when you are not using them. Even if one of your devices is lost or stolen, password protection can help protect your data against theft or unwanted access.

Wireless Configurations: Public Wi-Fi networks, like the one in your local Starbucks, don’t offer the same security as your private home or work network, yet 20% of internet users report completing financial transactions on public networks.vii It is always safest to assume that public networks do not offer any protection to your browsing. Consider configuring your devices so they do not automatically join detected networks (with your private home or work networks as the only exceptions).

Resources and Further Reading
National Institute of Standards and Technology (NIST)
Center for Internet Security (CIS)

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