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Block Woman surveys muslin money bags with a tag that says "taxes" and a small pile of coins

Your 401(k)’s After-Tax Contributions Are a Retirement Savings and Tax Superpower.

October 29, 2025 | Employee benefits/401(k)

Hopefully you’ve figured out the basics of your 401(k). Maybe you’ve even figured out whether or not you should contribute to your 401(k) pre-tax or Roth. But what about this

A Case Study in Navigating an IPO

October 29, 2025 | Pre-IPO and Going Public

Do you want to create a smart strategy for your company’s IPO, but you have options and shares and RSUs, you don’t know how they fit together, and it all

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Why a Traditional Investment Portfolio is Better than Real Estate

October 8, 2025 | Investing

If you want to invest in real estate because you want passive income, keep this in mind: There is no kind of investing that produces income more passively than a

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Is Your Company Going Public? Stop Obsessing About Taxes. Start Obsessing About Your Life.

August 13, 2025 | Pre-IPO and Going Public

It’s been a long few years, but your company is finally having its IPO. Lucky you! If your company is going (or has recently gone) public, then perhaps you are

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Should You Contribute Pre-Tax or Roth to your 401(k)?

July 9, 2025 | Employee benefits/401(k)

Recently I spoke on a panel of financial planners, here in my home of Bellingham, WA. The two other planners immediately made clear their love for Roth accounts. I was

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Reflections on 9 Years of Flow

May 9, 2025 | Financial planning

I’ve been thinking about this blog post for over a month now. Despite starting to think about it such a long time ago (by blogging standards), and despite generally being

Let us identify and explain the important issues for you

Sign up and get relevant discussions about money in your inbox twice a month.

The latest blog Posts

Your 401(k)’s After-Tax Contributions Are a Retirement Savings and Tax Superpower.

A Case Study in Navigating an IPO

Why a Traditional Investment Portfolio is Better than Real Estate

Is Your Company Going Public? Stop Obsessing About Taxes. Start Obsessing About Your Life.

Should You Contribute Pre-Tax or Roth to your 401(k)?

Reflections on 9 Years of Flow

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