Tax Planning Archives

When to Expect Your 2020 Tax Forms

As you prepare your taxes, here are answers to frequently asked...

Ryan Colis

Charitable Remainder Trusts (CRT)

A Charitable Remainder Trust (CRT) is an irrevocable trust that generates income for you or your beneficiaries with the remainder going to your favorite charity. Is it right for you?

Zach Hamilton

Can you gift too much?

A discussion of giving too much away might initially seem strange. But, if you’re not careful, you might inadvertently end up with a tax bill on funds you give away. This is called the gift tax and the IRS expects you to know it. After all, they’ve generously listed it on their website for you to read! So, how does it work?

Josh Whelan

The Mega Backdoor Roth Solo 401(k) for Solopreneurs

The Mega Backdoor Roth 401(k) has typically been reserved for select Fortune 500 companies. Here's how you - the Solopreneur - can access this little known strategy!

Josh Whelan

Taxes & Highly Appreciated Assets – An Introduction

You might be an early employee at Microsoft, a successful real estate investor, or the owner of a small business that has taken off. In each case, you own something worth a lot more than when you first acquired it. Now you’re staring down a large capital gain tax bill if you sell. Are you just stuck or is there anything you can do? We have a few ideas!

Zach Hamilton

Taxes & Highly Appreciated Stock

You might be an early Microsoft employee, tech company executive, or have been gifted shares of stock as a kid. You’d like to diversify, but the resulting tax bill seems almost as big as the portfolio itself! In Taxes & Highly Appreciated Stock, we’ll look at a case study and strategies to consider if you find yourself in this situation.

Zach Hamilton

Taxes & Highly Appreciated Real Estate

You own a few rentals, maybe an apartment building or two, and you’re looking at simplifying your life by selling them and retiring, but the tax bill is daunting. In this Real Estate Edition of our Strategic Guide to Highly Appreciated Assets, we’ll look at a case study and strategies you might consider if you find yourself in this situation.

Zach Hamilton

Taxes & Highly Appreciated Business Ownership

What started as a dream in your garage is now a thriving business! You’ve worked hard and now see a sale in your future…and a sizable tax bill. In this Business Owners Edition of our Strategic Guide to Highly Appreciated Assets, we’ll look at a case study and strategies to consider if you find yourself in this situation.

Zach Hamilton

The Mega Backdoor Roth – A Hidden 401(k) Benefit

Microsoft led the way in a rarely utilized benefit within their 401(k) plan – the after-tax Roth conversion. And, slowly but surely, other companies are adopting this plan feature. So, how does it work, what other companies offer it and is it worth it?

Josh Whelan

Tax-Loss Harvesting: Using Losses to Increase Return

No one likes a seeing their investments lose value. But opportunities exist in any situation, including market downturns. One such opportunity is called tax-loss harvesting. We discuss what it is, how it can help and when you might consider using it.

Ryan Colis

CARES Act and Tax Deadlines – 6 Coronavirus-Related Changes to Know

With so many feeling the effects of the COVID-19 quarantine, federal and state governments are moving to help. Here are a few of the notable tax deadline changes and stimulus efforts in the recent Coronavirus Aid, Relief, and Economic Security (CARES) Act. Tax deadlines, IRA & RMD changes, stimulus efforts, small business relief options and more.

Josh Whelan