Cowboys and Cufflinks

Cowboys and Cufflinks Welcome to Cowboys and Cufflinks, the podcast and radio show about Family, Freedom, and Finance.

We cover investing, retirement, taxes, and Social Security with grit, clarity, and real-world strategy to help you live life on your terms.

09/04/2026

Real financial planning should reflect real life.

That’s the idea behind MYFIT, a framework built around what actually matters. Not just growing money, but understanding how it supports lasting income, family priorities, and long-term decisions.

Because retirement isn’t just about hitting an age. It’s about knowing what your money is meant to do when you get there.💡

Comment 'CALL' and let's start the conversation.

09/03/2026

Think you’re diversified just because you own the S&P 500? You might want to look a little closer.

A surprisingly large portion of the index is concentrated in just a handful of companies. That means investors may be taking on more concentration risk than they realize.

Jeff Mathies breaks down one of the biggest dysfunctions he sees in investing today and why understanding what you own matters.

09/02/2026

Caleb Moore’s purpose has always been simple: to serve others.

Coming from a long line of public servants, Caleb grew up surrounded by people who believed in putting others before themselves. That example shaped who he is today and made service more than something he does, it became a defining part of how he approaches life.

Whether it’s his family, his community, or the people he works with, Caleb’s overarching purpose remains the same: use his time, talents, and experience to make a meaningful difference in the lives of others.

08/31/2026

The financial landscape is always changing.

Policies evolve. Tax rules change. New ideas become new realities.

🔍 That's why understanding the rules can be just as important as understanding your investments.

If you'd like to have a conversation about how today's environment could impact your financial plan, give our team a call at 719-434-3939.

The countdown is almost over... 🏈Preseason is wrapping up, the jerseys are coming out, the hype is building, and Sundays...
08/28/2026

The countdown is almost over... 🏈

Preseason is wrapping up, the jerseys are coming out, the hype is building, and Sundays are about to get a lot more orange around Colorado. We know the Mathies family is ready to yell for the Broncos. 🧡💙

Who is is ready is ready for football season?

08/26/2026

Nobody likes surprises when it comes to taxes. 😨

The challenge is that many people spend decades building retirement savings without thinking much about how they'll eventually access those dollars.

More options today can mean more flexibility later.

If you'd like to learn more about strategies that may help create greater tax flexibility in retirement, let's talk.

👉 Comment 'DISCOVER' below and we'll send you the link.

08/26/2026

Knowing how much you make and how much you spend is a great start but that’s not a financial plan.

A strong financial plan looks beyond today. It helps you prepare for the opportunities you’re working toward and the challenges you may never see coming.

What happens if your income suddenly changes? An unexpected expense hits? The market takes a turn?

Good financial planning isn’t just about preparing for what you expect. It’s about being ready for what you don’t.

Have a financial question you want answered? Give us a call:
719.434.3939

08/25/2026

Low-cost mutual funds are popular for a reason but are they always the best place for your money?

Keeping investment costs low matters, but cost is only one piece of the puzzle. Depending on your financial situation, looking beyond traditional mutual funds could provide opportunities to diversify your portfolio and better align your investments with your long-term goals.

The key isn’t finding the *cheapest* investment. It’s understanding what you own, why you own it and how it fits into your overall financial plan.

Have a question you want answered? Give us a call:
719.434.3939

08/24/2026

Can you just put all your money in the S&P 500 and call it a day?

It might sound like a simple strategy but investing isn’t just about chasing returns. Your goals, timeline, risk tolerance and overall financial plan all matter when deciding where your money should go.

08/24/2026

People naturally want certainty.

It's why headlines that claim to know where the market is headed get so much attention. 👀

The challenge is that markets don't come with a forecast.

Rather than trying to guess every twist and turn, a thoughtful investment strategy is built to navigate them over time.💡

That's an important distinction, and one that's easy to overlook.

Address

2139 Chuckwagon Road, Suite 200
Colorado Springs, CO
80919

Opening Hours

Monday 9am - 4pm
Tuesday 9am - 4pm
Wednesday 9am - 4pm
Thursday 9am - 4pm
Friday 9am - 12pm

Telephone

+17194343939

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