The RSU Tax Trap: When Should You Sell Your Company Stock, and How Can You Avoid Tax Underpayment?

It has been a rocky year for tech stocks. Since peaking in January, the tech-heavy Nasdaq is down nearly 5,000 points (about 30%).

Roth Conversions: To Convert or Not to Convert? It Depends

When you hear the word “convert,” you probably think of something other than retirement accounts. Converting that extra room to a recording studio, maybe, or converting an itinerant blog post reader to a client

Chris Jennings, Good to Know, Impact Investing, Investing and MarketsChris JenningsMay 18, 2022Comment

Mega Backdoor Roth, Part Two: Is the Mega Backdoor Roth Strategy Right for Me?

Depending on the specifics of your employer’s 401(k) plan (which you can access anytime by referencing the Summary Plan Description, or SPD), Mega Backdoor Roths via NRATs offer a ton of upside.

Mega Backdoor Roth, Part One: A Primer on Non-Roth After-Tax Contributions

Mega Backdoor Roth strategies have been in the news (not to mention Congress) a lot lately. In Part One, I review what they are, how they work, and how they differ from other retirement account strategies.

Retirees Turn Their Twilight Years into New Beginnings

Retirement doesn’t look like it used to — and for good reason. For prior generations, age 65 constituted a threshold between the working world and the leisure world. Once you crossed it, you took your gold watch, your pension, and your savings, and kicked back in some tropical locale.

RSUs vs. ISOs: Equity Compensation 101

Chances are, if you’ve reached a point in your career where your employer has granted you Incentive Stock Options (ISOs) or Restricted Stock Units (RSUs), you’re doing great. Both ISOs and RSUs are reserved for highly valued members of a company, people that organizations really want to retain for a long time. So, first things first, nice work!

Demystifying the Fear of Risk

It is important to understand how we feel about risk and how it impacts our finances and investments.

Risk, if properly managed, can actually work to our advantage.

Chris Jennings, Good to Know, Investing and MarketsChris JenningsDecember 19, 2020Heron WealthRisk, Financial Planning, FearComment

What emergency relief options should you consider during the Coronavirus pandemic?

Chris Jennings, Budgeting and SavingChris JenningsApril 7, 2020Coronavirus, Financial Planning, Financial CrisisComment

Are you eligible to receive a step-up in cost basis on inherited property?

Did you recently inherit or expect to inherit property? Whether it’s a house or investments, a step-up in cost basis can result in enormous tax savings

Tax and Estate PlanningChris JenningsApril 26, 2019Heron WealthTax, InheritanceComment

Does your income level allow you to contribute to a Roth IRA?

Roth IRA’s are a fantastic, tax-efficient way to save for retirement, but the rules around who can contribute, and how much, are complicated.

Tax and Estate PlanningChris JenningsApril 12, 2019Heron WealthRoth IRA, Tax, IRSComment

Answers & Observations