EP 53: Honest Communication & Taxes

Andy VandenBerg, CFA
Founder

What's in store for you:

  1. Photo From My Life
  2. Life Thought: The Power of Honest Communication
  3. Financial Thought: Well, tax day is officially behind us!
  4. Good Sh*t: The Pitt

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Photo From My Life:

We went to a Savannah Bananas game last weekend, and it was non-stop entertainment. From an even better version of baseball to electric dance performances and the hilarious Dad Bod Squad, the two hours flew by. Even better — the $35 ticket included unlimited food and drinks!

Life Thought:

The Power of Honest Communication: This week, I sat through three straight days of 12-hour meetings. One after another, different teams presented their quarterly results. And after a few hours, a pattern became pretty clear.

The people who tried to "sell" their results — spinning a narrative to make things sound better than they really were — immediately lost trust. It wasn’t that they were bad people or even doing a bad job. It’s just that their updates felt curated and a little disconnected from reality. People became more skeptical about what they were presenting.

But, a few people really stood out. These leaders simply shared the reality. They walked in, showed specific data about where things stood, described the challenges, and calmly explained what they were doing to fix them. No emotion. No blame. No complaints. Just facts and plans.

Those were the people everyone trusted.

And honestly, I'm starting to realize the same is true outside of business too. In friendships and families, the people you value most aren't the ones who gloss over problems or turn every conversation into a vent session. They’re the ones who can name what's going wrong without spiraling into negativity and work toward solutions without making you feel weighed down. We all have friends that fit into this group. I'm guessing they are the ones you want travel internationally with.

Reflecting on this week, I realized this is something I can get better at. I want to be the calm, clear leader, but there are times when I find myself getting a little defensive and trying to "sell" too much.

This week was a good reminder for me. The goal is to build trust. And that starts with being real and transparent.

Financial Thought:

Well, tax day is officially behind us!: A friend recently reached out, frustrated about a big tax bill, and asked if he should hire a tax strategist. It’s a good question — and it made me realize it’s worth sharing my perspective on when tax strategy actually moves the needle.

For most W-2 employees, the truth is there’s only so much you can do. Despite the fact the tools are limited, it doesn't mean there's no value to thinking about it. Proper withholding, tax-efficient investing, timing charitable giving through a donor-advised fund, and making smart use of benefits like HSAs, 401(k)s, or stock compensation plans can add up meaningfully over time. A good wealth manager should be able to help you cover these bases without needing to hire a tax strategist.

But — if you own a business, the game changes completely. Business owners have access to a wide range of tools and strategies that simply aren't available to salaried employees: entity structuring, retirement plan optimization, expense management, asset shifting... the list goes on. However, it's important to remember the real advantage comes from proactive planning. You should set things up before the year ends, not scrambling once April rolls around.

If you're a business owner, it’s definitely worth investing in a great tax advisor. The right advisor can help you legally and intelligently structure your finances in a way that meaningfully reduces your tax burden over time.

I'll be the first to admit I'm not a tax expert, but I continue to learn more and have partnered with a thoughtful accountant for my clients. If you ever want a 2nd perspective, I'm happy to help.

Good Sh*t:

The Pitt: I heard about a new show recently called The Pitt, and it's too good not to share. A close friend of mine, who happens to be an ER doctor, told me it’s the most accurate show he's ever seen about life in the emergency room.

The first season unfolds over a single, intense 15-hour shift in a Pittsburgh emergency room. Each episode represents one hour of this shift, which highlights the insane pace and emotional challenges faced by ER staff.

I don't think these doctors get enough credit. My partner, Ben, recently told me that he gives his doctors a hug to thank them. I thought that was a bit extreme, but now I get it.

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Andy VandenBerg, CFA
Founder

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