


The Trump Account (And What Actually Matters): You may have seen the recent Wall Street Journal article on Trump Accounts. A few clients reached out after reading it, and I was planning to include this in my next client letter, but it’s getting enough attention that it’s worth sharing here.
The article highlights a pretty compelling idea. Start investing for a child at birth, contribute consistently, then eventually convert the account into a Roth IRA. The recipient could end up with millions of dollars growing tax-free over their lifetime.
That’s the headline. And like most headlines in finance, it’s directionally right, but there's a lot more nuance.
At a high level, these accounts:
The “hack” the article focuses on is funding the account early, then converting it at the right time (low-income years for the child), paying the tax, and letting it compound tax-free for decades. In their example, parents investing $5k per year for 18 years turns into ~$3m by retirement for that child. Pretty awesome.
The article highlights two important ideas:
If you (as a parent or grandparent) pay the tax on a future Roth conversion, you’re effectively:
But, as with most topics, I suggest a bit of caution. This is where reality matters more than the headline.
This is not a liquidity tool. If your goal is helping a child with college, a home, or early adulthood, there are usually better options. With this strategy, you’re trading flexibility for tax benefits. To make this work, you’re committing capital for decades and using additional cash to pay taxes later.
Before even thinking about this, most families should already have:
This strategy is an optimization, not a foundation. The outcome depends on contribution discipline, market returns, and properly timing things like Roth conversions and avoiding issues like the Kiddie Tax.
So, should you care? For most people, this is interesting, but not urgent. If you’re already doing the right things, you’re capturing most of the benefit already. If these accounts end up being well-structured, they could be a nice addition. If you can get the government seeding? Of course you should use it!
Could I Become a Healthcare Tourist?: I’ve had a handful of conversations recently with other self employed families who end up purchasing their own insurance like my family. We're all frustrated.
We pay massive premiums every year. We have high deductibles. And when we actually need care, we end up cash paying anyway and get a mediocre experience.
We're technically insured for catastrophic events, but functionally uninsured for everything else. A friend shared a crazy piece of advice last week. They suggested I become a medical tourist.
Okay, what we're they actually suggesting? They suggest I travel with my family for one week a year and complete all routine medical appointments.
Instead of dealing with multiple appointments spread across months, unpredictable billing, and annoying wait times, we consolidate everything into one highly efficient week.
In places like Costa Rica, Japan, China, and South Korea, private clinics are built for this.
A realistic week might include:
You're not waiting weeks between appointments. Everything is scheduled in the correct order for the week.
So, does the math actually work? I wanted to run some simple analysis that may be based on my specific information.
Let’s take a typical self employed family:
Now compare that to one annual trip:
So, the costs are relatively comparable to our entire deductible. But, I have to imagine we'd be getting better service and care. I guess we'd also be getting a cool vacation. Maybe the right argument is that I could choose even worse insurance which would be more cost effective.
As I think through this, there are obvious tradeoffs:
So, should I do it?

Theo of Golden: A reader of this newsletter reached out suggesting I read Theo of Golden. First of all, pretty cool that I'm lucky enough to have friends from this newsletter who feel compelled to share things like this. Thank you.
One of my goals for this year is to read more so I purchased the book and started almost immediately. The first 75% of the book was good, but not A+. However, the final 25% was incredible. Creative, surprising, and fulfilling.
I have a new goal in life. Be like Theo.
Check out the book on Amazon here.
Disclaimer: VDB Wealth is a registered investment adviser. Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and unless otherwise stated, are not guaranteed. Past performance is not indicative of future performance.
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