#44 - The Greatest Financial Advisor You Never Knew You Had
Greetings!
On This Monday’s Episode of the podcast Your Money Guide on the Side:
Guest: Dan Brigham - He paid off $100k in debt and wants to help you do the same. For free. (That’s why I like him.)
We dive into the moments that shaped Dan’s mission, including his two-year journey out of over $100,000 in debt and why vulnerability—not credentials—is his currency of trust when helping others accomplish their financial goals. We talk about the backlash he gets over car payments (you’ve been warned), and why he thinks showing integrity is far more important than performing expertise.
You’ll also hear us unpack:
What makes people defensive about money
How to stay grounded (literally and spiritually) when the work feels heavy
And the books that actually changed his life (spoiler: one’s still in print after 2,000 years)
Like where the podcast is going? Leave a review here and help spread the word, and then let me know, so I can send you a personal thank you!
Dislike where the podcast is going? Write to me any time, any day, and I will always read the feedback and incorporate it into future episodes. This endeavor is for you, and I will work endlessly to add as much value to your lives as possible.
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The Greatest Financial Advisor You Never Knew You Had
Or: The Active Nature of the S&P 500
We often call index funds “passive.” But the S&P 500? It’s quietly one of the most active investing machines you could imagine.
Here’s what most people do NOT know about the nature of the S&P:
1. It’s self-cleansing by design.
The S&P 500 is weighted by market capitalization, meaning bigger companies get more influence. When a company is thriving, its stock price rises (sometimes), and it naturally takes up more space in the index. And when a company starts to slip, it quietly sinks to the bottom. No meetings. No fund manager pulling the strings. The index does the work for you, so you can continue to enjoy watching The Last of Us on Max. (Anyone else ticked off they’re releasing this season weekly? Killin’ me.)
2. Sectors rotate over time.
And this isn’t just about individual companies. Entire industries rise and fall inside the index. As many of you know, tech is dominant right now: companies like Apple, Microsoft, and Nvidia sit at the top. And many investors are “worried” this won’t last. But guess what? It doesn’t have to last. Because 40 years ago, it was energy and industrials leading the way. And 40 years from now, it will most likely be another sector. The S&P doesn’t care what’s in charge; it just keeps tracking whatever’s growing.
3. Downside Protection
Many new investors fear their investments will magically go to “zero.” And yes, all investing is and always will be risk. BUT, by its nature, the S&P cannot “go to zero,” and here’s why: when a company can no longer meet the S&P’s standards, it’s dropped completely, and a new company (that’s typically performing better) replaces it. Criteria include:
Market cap too low (aka, the companies that we’re worried might go to “zero”)
Consistently poor earnings or looming bankruptcy (again, see above)
Regulatory noncompliance
Too little trading volume or free float
You don’t have to worry about selling your losses, as the S&P does it for you while it’s automatically reinvesting in the winners of the era.
So yes, the S&P 500 looks and sounds passive. But it’s actually a disciplined, dynamic, and brutally critical machine. Which is exactly why it works.
As always, hope this gives you all something to think about throughout the week.
Tyler
Your Money Guide on the Side
