Strategic Financial

Putting 100% of your kid’s savings into a 529 plan might be a mistake.

And could be overcommitting to a future that doesn’t exist yet.

College is changing faster than most parents realize.

AI, trade programs, apprenticeships, and remote learning are already reshaping education.

So how we look at saving for the future needs to be looked at too.

I still love 529 plans and they make a ton of sense for a lot of reasons.

• Tax-deferred growth
• Tax-free withdrawals for education
• And now up to $35,000 can roll into a Roth IRA for your child if the money isn’t used for school.

But like everything we look at with our clients, great planning isn’t about picking one perfect account.

It’s about flexibility.

Many families we work with split savings for their kids and grandkids across:

• 529 plans
• UTMA / UGMA accounts
• other long-term investment accounts for kids (including the new Trump accounts)

Different buckets.
Different tax rules.
More flexibility depending on how life actually unfolds.

Because the question shouldn’t be: “Should I use a 529?”

It should be: “How do I design this so it still works if college changes completely?”

That’s the real planning.

These tax mistakes might put a target on your return.

Most IRS audits aren’t random.

There are specific things that trigger them and they usually start with a simple mismatch or red flag on your tax return.

And if you’re a business owner or high-income earner, your return naturally gets a little more scrutiny.

Things like missing income (missing 1099s), extended business losses, and overly generous or aggressive deductions can all raise questions.

So if you fall into these categories, make sure you have good documentation and explanations ready.

The goal isn’t necessarily to avoid the IRS.

It’s to make your return so clean, organized, and boring…

that if the IRS ever looks at it, there’s nothing to worry about.

As always, be sure to work with your tax advisor and financial planner to make sure you are getting this right and avoiding headaches down the road.

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The $15M exit that turned into $5M

A client just sold their business for $15 million… and walked away with about $5 million in the bank.

Here’s where the other $10M went:

First, $3M of business debt had to be paid off.

Then $1M of working capital had to stay in the business as part of the deal.

And then the rest of the real-world deductions show up:

• Taxes
• Legal and accounting fees
• Investment banker fees
• Employee bonuses
• Rollover equity
• Earnouts

By the time everything settled, the actual cash he walked away with was closer to $5M.

Still great.

But very different than the $15M headline sale price.

For many business owners, their company is their primary retirement asset.

Which means the number that really matters isn’t the sale price…

…it’s the after-tax dollars that actually hit your bank account.

Understanding that number years before you sell can completely change how you structure the deal, plan for taxes, and prepare for retirement.

Because when it comes to selling your business, knowing what you are going to keep matters far more than what you sell it for.

Make sure you are working with an advisor who can help you determine what the right number is.

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The best financial plans look nothing like this.

This is one of the wildest things I’ve ever watched.

Alex Honnold climbing Taipei 101.

No ropes, no safety net.

And weirdly… it’s a perfect metaphor for how real wealth actually gets built.

Not one big heroic leap.
Not a single “home run” move.
But small, intentional steps.
Planned. Practiced. Adjusted over time.

But here’s where the analogy ends:

In money, one mistake shouldn’t be catastrophic.

One bad year shouldn’t derail your entire future.

One unexpected turn shouldn’t send everything off the rails.

That’s why real financial plans have:

• A rope
• A safety system
• And a guide who’s done this climb before

Same climb. Better plan.

💻Upcoming Webinar: and if you’re a business owner thinking about exits, entity structure, and keeping more of what you build, we’re hosting a deeper dive on this exact topic in our upcoming webinar.

👉Register today: Link in Bio