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351 ETF Conversions

Section 351 of the Internal Revenue Code lets investors swap a concentrated, highly appreciated stock position for shares of a diversified ETF without triggering capital gains tax. Here’s how the strategy works, the requirements it must meet, and when it makes sense.

Saving for Kids: The New Trump/530A Accounts

A look at the new Trump/530A accounts for kids alongside 529 plans, taxable custodial accounts, and custodial Roth IRAs — plus the Roth conversion and 401(k) split strategies that make them powerful

Donor-Advised Funds

Donor-Advised Funds (DAFs) are charitable giving accounts that allow one to front-load their donations in a single taxable year while retaining the flexibility to grant to various charitable organizations over multiple years.

Early Withdrawals for Roth IRAs, Backdoor Roth IRAs, & Mega Backdoor Roth 401ks

Just like how the principal of Roth IRAs can be withdrawn tax-free & penalty-free, the same can be done with Backdoor Roth IRAs & Mega Backdoor Roth 401ks if certain rules are followed.

What is Alternative Minimum Tax (AMT) and How Are ISOs Affected?

AMT, or Alternative Minimum Tax, is a secondary federal tax system parallel to the regular IRS tax system. Its purpose is to ensure taxpayers who receive too many deductions & tax breaks still pay a minimum amount of tax to the IRS.

An Overview of Qualified ESPPs (Employee Stock Purchase Plans)

Qualified ESPPs allow you to purchase stock at a discount from your company while offering favorable LTCG treatment if certain holding requirements are met.

Asset Location and Other Investment Portfolio Tax Considerations

This article discusses tax optimization techniques including asset location, potential adjustments for significant capital losses from tax loss harvesting and tax considerations for alternative investments.

Avoiding Double Taxation on RSUs, ESPP, ISOs, and Other Company Equity

The sale of employer equity can result in double taxation if one is not careful with making the necessary cost basis adjustments.

Backdoor & Mega Backdoor Roth Strategies

Backdoor Roth strategies which allow high-income earners to still contribute to a Roth IRA and potentially super-contribute to their Roth 401k

Enhancing the Tax Benefits of Direct Indexing with a Short Overlay Strategy

An advanced tax strategy that enhances the potential for capital losses generated by direct indexing by adding one or more short positions.

Environmental, Social, and Governance (ESG) Funds Overview

Alexa defines Environmental, Sustainable, and Governance (ESG) investing, and summarizes how to navigate the growing number of ESG funds available.

New Rates For I Bonds – April 2023

The new I Bond semi-annual inflation rate will be 1.69%. This article will explore how we calculate that and information on those considering whether they should buy in now, or sell old I Bonds.

What are I Bonds? Should I Buy Them?

I Bonds are inflation-protected bonds offered directly by the U.S. Treasury. Although they generally won’t return as much as stocks, they are great to maintain purchasing power.

Kiplinger.com: A Quick Primer on Tax-Loss Harvesting

Tax-loss harvesting can be useful in an array of situations, but understanding when to best utilize this strategy is key. Tax-loss harvesting is the practice of selling an investment for a loss.

Kiplinger.com: A Do-It-Yourself Replacement for Indexed Annuities

The first component of this approach, comprising the majority of investment dollars, is the purchase of one or more certificates of deposit. There are banks offering CDs insured by the Federal Deposit Insurance Corporation with rates of more than 2% for a 10-year term.

Kiplinger.com: Like IRAs, HSAs Can be Valuable Retirement Savings Vehicles

Typically, health savings accounts (HSAs) are used as savings accounts for medical expenses, providing tax-deductible contributions and tax-free withdrawals.

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