Quarterly financial planning guide for busy investors and entrepreneurs


Our 2022 Quarterly Financial Planning Guide focuses on the complex planning needs of investors and entrepreneurs in these dynamic times. We believe there is a very high likelihood of tax reform and changes to the regulatory landscape. Faced with unknown outcomes, investors and entrepreneurs would be wise to focus on evergreen financial planning items.

Below are targeted planning topics investors and entrepreneurs should consider in each quarter of 2022. We recommend you work closely with SVB’s Private Bank to adjust your strategy as changes to capital gains taxation, retirement savings, estate planning, stock option vesting, and many other financial planning areas take shape.

Q1 Quarterly planning strategies
Everyone Entrepreneurs should also consider Investors should also consider
Develop an investment strategy, create a budget and organize taxes.
  • Establish your annual needs and objectives.
  • Meet with your advisor/banker.
  • Update your asset allocation, diversification and investment selection/location to help meet goals.
  • Update your emergency fund or sources of liquidity, such as home equity line of credit or securities-based line of credit.
  • If eligible, revisit Qualified Small Business Stock treatment for founder shares, especially if considering an exit or secondary.
  • Upcoming sale or IPO of your company? Plan before receiving an LOI for the most impact on your balance sheet.

  • Balance private ventures with traditional long-term investing.
  • Define essential and discretionary expenses, including updated forecasting for angel/PE investments.
  • If eligible, revisit Qualified Small Business Stock treatment for founder shares of portfolio companies, especially if considering an exit or secondary.

Case study

General Partner of VC firm reviews the distributions and investments that were made in her LP fund during the previous year. Working with her CPA, the GP identifies two Qualified Small Business Stock (QSBS) sales.

  • One QSBS sale qualifies for Section 1202 provision which excludes 100% of the gain on the sale, limited to the greater of $10 million or 10 times the adjusted basis. The CPA documents the sale of the stock and the GP receives the first $10 million of gains free of Federal Income Tax and the Net Investment Income Tax.
  • The second QSBS sale occurred after the GP owned the stock for more than six months but short of the 5-year holding period required to utilize Section 1202. In this case, the GP elects to rollover the proceeds (within 60 days of the sale) of the QSB stock into another QSB stock utilizing Section 1045. The CPA records the holding period and adjusted tax basis from the original shares into the newly acquired QSB stock.

Everyone Entrepreneurs should also consider Investors should also consider
Focus on Retirement
  • Open and fund an IRA, in addition to contributing to an employer 401(k) plan.
  • Consider converting the IRA to a Roth IRA
  • Revisit your 401(k) deferrals.
    Review Estate Plan
  • Establish foundational estate documents: will, living trust, health care directive, power of attorney, etc.
  • Consider advanced estate planning techniques (CRT, GRAT, ILIT, etc.).
  • Utilize, if possible, self-employed - retirement plans that can help reduce/defer income tax liability (e.g. SEP IRA, etc.).
  • Consider advanced estate planning techniques (CRT, GRAT, ILIT, etc.).
  • Consider advanced estate planning techniques (Charitable Remainder Trust (CRT), Grantor Retained Annuity Trust (GRAT), Irrevocable Life Insurance Trust (ILIT), etc.).
  • Considering opening a self-directed IRA or Roth IRA to invest in angel investments.
  • Be informed about new regulations that could change some core HNW estate planning techniques to reduce a taxable estate.
  • Consider advanced estate planning techniques (Charitable Remainder Trust (CRT), Grantor Retained Annuity Trust (GRAT), Irrevocable Life Insurance Trust (ILIT), etc.).
Everyone Entrepreneurs should also consider
Investors should also consider

Time for a Mid-year Check

  • Conduct a performance review, compare asset allocations to target and rebalance, if needed.
  • Consolidate accounts, i.e.: roll over old 401(k) plans, reduce number of investment and banking accounts.
  • Determine whether monitoring systems such as Mint® or Quicken® can help manage your Inflows and outflows for your business and gauge your overall private stock exposure.
  • Confirm sources of liquidity available to meet unexpected cash flow needs.
  • Review portfolios skewed towards private stock, venture, carried interest and other forms of non-traditional, private and less liquid investments. Rebalance, if possible, otherwise confirm sources of liquidity are available to draw upon in a tail risk market event.

Case study

An Entrepreneur is working with a new advisor. During a review of their portfolio, the advisor notices mutual funds held in a taxable account (hedge funds and high-performance, high-turnover mutual fund strategies) paid out significant short-term capital gains in the form of year-end distributions. The advisor recommends moving the tax-inefficient strategies to their retirement account and keeping tax-efficient strategies, such as US municipal bonds and large cap stocks, in their taxable account. This optimizes the tax-cost of their investment strategy and gives the portfolio the potential to compound faster.

Everyone Entrepreneurs should also consider Investors should also consider

Start Year-End Tax Planning

  • Manage investment gains and losses (e.g. tax-loss harvesting).
  • Revisit Alternative Minimum Tax (AMT), if applicable.
  • Utilize tax-credits and deductions (e.g. education, energy credits, etc.).
    Execute Annual Gifting
  • Gift long-term capital-gains property.
  • Work with CPA to determine whether it makes sense to convert part of all of an IRA account to a Roth IRA .
  • Review stock option exercise strategy with your CPA and expect tax changes in 2017, which may affect AMT treatment; consider exercising some ISOs now (before the next 409(a)), knowing that the tax implication is pushed to 2018, but be prepared to exercise more if the AMT implication on ISOs goes away.
  • If you have taken liquidity (distributions, secondary, or other large exit) consider making a more significant than usual charitable gift. Optimize ways to give through Donor Advised Funds (DAFs).
  • Utilize annual gift exclusion amounts ($14k per person in 2017) to fund 529 plans, children’s trusts, support beneficiaries and fund adult children’s ROTH contributions.
  • If you have taken liquidity (distributions, secondary, or other large exit) consider making a more significant than usual charitable gift. Optimize charitable objectives by establishing a Donor Advised Fund (DAF).

Case study

A Series C technology company goes through a merger with a public company for cash earlier in the year. The exit results in a significant liquidity event for the CEO. The financial advisor discusses ways to reduce the tax liability from the exit. The stock is not deemed QSBS and would not qualify for capital gains exemption. The advisor and the client’s CPA, suggest that the CEO make a sizeable charitable contribution to help reduce current year tax liability. In line with the client’s family philanthropic intentions, a discussion about Donor Advised Fund(s) (DAFs) and private foundations follows. The CEO and his spouse decide to open and fund a DAF which results in a significantly lower tax bill and creates a family fund for future charitable grants . The alternative would have been to gift shares of the private stock before the final determination letter of the acquisition had been issued to avoid long-term capital gains in addition to getting the deduction for the charitable contribution.

Case study

An Entrepreneur asks their CPA to estimate his tax liability for the current tax year. The CPA estimates they will be facing higher ordinary income tax than Alternative Minimum Tax. The CPA recommends exercising Incentive Stock Options (which increases the AMT liability) up to the point where the AMT tax liability is close to the ordinary tax liability. The entrepreneur thus receives an AMT tax holiday; he gets to exercise ISOs without increasing his tax liability.

Key 2017 annual limits relating to financial planning*

Elective deferrals 401(k), 403(b), etc.
Catch-up contribution (for age 50+)
$6,000 (no change)
IRA or Roth IRA contribution limit
Catch-up contribution (for age 50+)
$1,000 (no change)
SEP IRA contribution maximum
Roth IRA phase-out (married filing jointly)
$204,000 - $214,000
Social Security wage base $147,000
Annual gift tax exclusion $16,000 (no change)
Gift Exclusion to a non-U.S. citizen spouse $164,000
Lifetime Transfer Tax/Estate Tax Exclusion(1) $12,060,000 per decedent
Maximum estate tax rate 40% (no change)
Highest marginal fed. income tax rate (37%)—Single $539,900
Highest marginal fed. income tax rate (37%)—Married $647,850
Standard deduction – Single or married filing separately $12,950
Standard deduction – Married filing jointly $25,900
Standard deduction – Head of Household $19,400
Kiddie tax limited standard deduction $1,150
Alternative Minimum Tax (AMT) exemption—Single/Married Filing Jointly/Married Filing Sep. $75,900/$118,100/$59,050
Flexible Spending Account $2,850
For California Residents: CA College Access Tax Credit Fund** 50% of contributed amount


We encourage all Private Bank clients to set up a plan and keep at least quarterly updates in mind for 2022. These key tactical shifts to your planning will help you stay on top of what promises to be an active cycle for private market outcomes, liquidity, and the planning needs affected by new regulations and the markets. We are here to serve you with advice and help you get on track with your planning strategies.

The fine print

*No change means that there were no changes made for 2017 compared to 2016.

**The College Access Tax Credit (CATC) is a credit available to individuals and business entities that contribute to the CATC Fund in 2017. Sources: Based on current published tax rates from IRS, CCH and College for Financial Planning web sites. Individual tax rates may differ based upon current specific tax situation.

Mint and Quicken are independent third parties and are not affiliated with SVB Financial Group.

The views expressed in the article are those of the author and/or person interviewed and do not necessarily reflect the views of Silicon Valley Bank, a division of First-Citizens Bank and First Citizens BancShares, Inc. The materials on this website are for informational purposes only, are subject to change and do not take into account your particular investment objective, financial situation or need. Since each client’s situation is unique, you should consult your financial advisor and/or tax planning professional before acting on any information provided herein.