EP 94: Stupid Games -> Stupid Prizes

Andy VandenBerg, CFA
Founder

What's in store for you:

  1. Photo From My Life
  2. Financial Thought: Financial Planning Cases
  3. Life Thought: Stupid Games, Stupid Prizes
  4. Good Sh*t: Pens

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Photo From My Life:

My sister-in-law got married last weekend! Once I was done officiating, it was great to celebrate with lots of family and friends!

Financial Thought:

Financial Planning Cases: You’re probably sick of me writing about financial plans.

But I’m going to keep doing it. Because they’re the backbone of any solid wealth strategy. Whether you’re thinking about investing, taxes, estate planning, or even how to structure your income, it all starts with a plan.

Financial planning is part science and part art. It’s driven by numbers, but it’s also completely dependent on a mix of assumptions: future income, market returns, inflation, spending habits, goals that change over time.

For complex clients, it's helpful to build multiple scenarios. Not to create confusion, but to give clarity across different outcomes. Here’s how I typically frame it:

  • Base Case: What we expect to happen based on current data.
  • Downside Case: What happens if things underperform (e.g., lower income, weak markets, delayed liquidity).
  • Upside Case: What if things go better than expected? (e.g., early exit, big bonus, strong equity performance)

If you’re in private equity, this might mean high vs. low carry. If you’re in tech, it’s how much your RSUs are worth. If you’re in a W-2 role, it’s how your comp evolves over time. Everyone has variables and planning needs to flex accordingly.rom there, we tier goals into essentials (think: mortgage, education, retirement) and dream goals (second home, travel, lifestyle upgrades). A strong plan makes sure those essentials are covered in every case — and gives you visibility into when and how those dreams become possible.


Here’s a fryou can work I often walk clients through (see below). It’s not one-size-fits-all, but it does something that every good plan should do: it helps you make better decisions today with a clearer picture of tomorrow.

Hch, that’s not the point. This is just the right way to serve people.

Stupid Games -> Stupid Prizes: One of my favorite sayings is 'Play stupid games, win stupid prizes.'

Now obviously, I’m not talking about games. I come back to this saying often when I feel like I’m grinding away toward something without stepping back to ask, “Wait. Do I actually want this prize?”

This shows up for most people in work. We usually default to cpasing the next rung up the ladder. More responsibility, bigger teams, higher expectations. But do we really want the life that comes with the prize we’re chasing?

This is where I find it helpful to take a step back and reflect on what I want. If I’m working this hard, is the end result something I genuinely want? Or am I subconsciously chasing someone else’s version of success?

This mindset doesn’t just apply to work. It applies to the house you’re saving for, the city you live in, the hobbies you pursue, the life you're building. Once you know your long-term goals, you can start to audit your daily actions and determine if your actions are leading you to the right outcomes. Or are they leading you somewhere else entirely?

Life is just one big adventure. That's the fun part. I don't want to wake up when I'm 60 and realize I was following the wrong map.

Good Sh*t:

Pens: Let’s talk about something underrated. Using a good pen.

It’s a tiny thing, but having a smooth, consistent, high-quality pen changes the entire writing experience. I swear they make my handwriting better too. Here are two pens I'm loyal to:

Sharpie S-Gel

Shout out to my sister for putting me onto this one. Clean, dark lines, and no smudging.

Pilot G2

A classic for a reason. Reliable, smooth, and perfect for everyday use.

If you’re still using whatever pen you grabbed from a hotel nightstand, treat yourself. It’s a simple upgrade that pays off every single day.

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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Andy VandenBerg, CFA
Founder

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