Discounted Roth Conversions: What’s That Private Investment Really Worth?

When you're converting traditional IRA assets to a Roth, the tax bill hinges on what those assets are worth—not what you paid. For private placements and illiquid investments, that valuation isn’t straightforward. But done strategically, it can unlock meaningful tax savings. This article unpacks how to value private assets for Roth conversions, which methods the IRS scrutinizes, and how to convert with confidence and compliance.

Bracket Management: The Secret Window Most Retirees Miss

Early retirement offers a rare opportunity—a quiet tax window that many retirees overlook. But with smart Bracket Management, you can turn this lull into a long-term win. By intentionally recognizing income during low-tax years, you can fill your lower tax brackets strategically and reduce the pressure of future RMDs, Social Security, and Medicare premiums. Studies suggest this proactive planning can add six figures of value over time. Don’t let the moment pass.

7 Reasons to rethink a self-directed IRA (SDIRA)

Self-directed IRAs (SDIRAs) have been around since the 1970s—almost as long as the traditional IRA. But while typical IRAs hold stocks and mutual funds through familiar custodians like Fidelity or Schwab, SDIRAs let you invest in: Real…

BulletShares ETFs vs. Traditional Bond Ladders: Pros and Cons for Retirees

Buying and selling individual bonds can be hard. The process is slow. Prices aren’t always clear. Sometimes, it’s hard to know if you’re getting a good deal. And certain bonds, like municipal ones or bonds with special features, can be…
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Are You Getting Your Money’s Worth from Morgan Stanley Private Wealth Management?

Morgan Stanley Private Wealth Management offers prestige and polish—but at what cost? If you're not using their full suite of family office services, you may be overpaying. This review breaks down their revenue model, highlights hidden incentives, and explores whether bundling advice, custody, and investments actually delivers value.

How to Minimize Your Retirement Tax Burden

Here's the three step tax planning process I use in real life to minimize my clients retirement tax burden. The framework is flexible and applies universally. Using this framework you can do your own tax planning or at least understand how the sausage is made.