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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

“They’ll Split It Later” Is One of the Biggest Estate Planning Mistakes I See

When Jim updated his retirement account beneficiaries after his wife passed away, he wanted to keep things simple. He had three adult children, but instead of listing all three equally, he named only his oldest daughter, Courtney, as the sole beneficiary. His reasoning sounded harmless enough: “She’ll do the right thing and split it with her brothers.” And to be fair, Courtney fully intended to. That was the plan. Until real life got involved.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

The $300,000 Tax Mistake Hidden Inside a Quitclaim Deed

“I just want to make things easier for my kids someday.” That’s what Diane told me when she explained why she added her two adult children to the title of her home using a quitclaim deed. No lawyers. No real planning. Just paperwork at the county office and a belief that this would help the house “avoid probate” and smoothly transfer to the kids later. It sounded simple. It turned into an expensive mistake.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

Employee Stock Purchase Plans: Great Benefit or Financial Trap?

When people review a new job offer, they tend to focus on salary first. Then maybe the bonus. The health insurance. The retirement plan. And somewhere buried in the benefits packet is something called an Employee Stock Purchase Plan, or ESPP. For some employees, this can be an excellent wealth-building tool. For others, it becomes another way to accidentally become overconcentrated in one company while neglecting more important financial priorities. So let’s simplify what this benefit actually is and when it makes sense to use it.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

NIL Money Is a Business, Not Just a Paycheck: What Student-Athletes Need to Know (Part 2)

One of the biggest mindset shifts student-athletes need to make in the NIL era is this: You are not “just getting paid.” You are operating a business. The moment money starts coming in through sponsorships, appearances, social media deals, camps, autograph signings, affiliate partnerships, or brand collaborations, you are no longer simply an athlete. You are now managing income, taxes, contracts, branding, legal risk, and financial decisions that can impact you for years. Very few immediately think:
“How do I build financial infrastructure around this income?”But that’s exactly the question athletes should be asking.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

Smart Financial Decisions for NIL Money: What College Athletes Need to Know Before the Money Starts Flowing (Part 1)

For years, college athletes generated enormous value while making very little money themselves. Now the NIL era has completely changed that. Student-athletes can earn money through endorsements, appearances, sponsorships, social media, autograph signings, camps, and brand partnerships. One of the biggest mistakes NIL athletes make is assuming the money works like a normal paycheck.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

Spring Cleaning Your Financial Life: Why Decluttering Your Money Matters as Much as Your Closet

Every spring, we pull out the trash bags and cleaning supplies, ready to tackle the accumulated clutter of another year. We sort through closets, donate clothes that no longer fit, and marvel at how much stuff we've managed to collect in just twelve months. But when was the last time you spring-cleaned your financial life?

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

The $7,500 Decision That Could Change Your Teen’s Entire Financial Life

There are very few moments in life where a small decision creates a massive long-term impact. Your child’s first job is one of them. Because while most teenagers are thinking about spending their first paycheck, this is actually one of the most powerful windows you have to set them up for long-term financial independence. And the tool that makes it possible is simple: A Roth IRA.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

Net Worth Doesn’t Matter (At Least Not The Way You Think It Does)

We talk about net worth like it’s the ultimate scoreboard. Hit a certain number and you’ve “made it.” Track it long enough, and you’ll feel secure. But here’s what I see in real life: you can have an impressive net worth on paper and still feel financially constrained. That disconnect matters. The goal is to have control, flexibility, and options in your life. The number you should be tracking is liquid net worth.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

Gold: All That Glitters Still Isn’t That Great Of An Investment

Gold had a moment. In 2025, it was one of the best-performing assets, up nearly 65%, its strongest run in decades. And yes, that kind of return gets attention, especially when it wasn’t driven by the usual tech darlings. But strong performance doesn’t automatically make something a great investment. And gold, in my view, still isn’t special.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

Solo 401(k) Plans: A Powerful Retirement Tool for Business Owners

If you’re a small business owner or solo entrepreneur, a Solo 401(k) is one of the most powerful retirement savings vehicles available. It combines high contribution limits with flexible tax strategies, including the ability to take advantage of the much-talked-about mega backdoor Roth.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

Health Savings Accounts (HSAs): The Retirement Tool Most People Miss

Most people think of HSAs as "money to pay medical bills." That’s true, but it’s only scratching the surface. In reality, a Health Savings Account (HSA) is one of the most tax-efficient accounts available for long-term planning, especially if you think about it over decades instead of just year-to-year. Let’s unpack what makes HSAs so powerful, and how you can take full advantage of them.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

Creating Lifetime Tax Flexibility

Why having options matters more than finding the “perfect” tax strategy. Most people think retirement planning is about one big question: “How do I pay the least in taxes right now?” That’s a good question… but it’s not the right one. The better question is:
“How do I give my future self the most flexibility?”

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

Why Millennials Are Better Prepared for Retirement Than Their Parents

Sorry Boomers, but Millennials aren’t waiting around for Social Security to save the day. We learned early that retirement is a personal responsibility, not something an employer or government pension system will automatically provide. Unlike many of our parents’ generation, we rarely had the safety net of a pension, so we had to take matters into our own hands.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

The Millionaire Next Door, and You Would Never Know It

When most people picture a millionaire, they imagine a flashy lifestyle. Luxury cars. Big homes. Designer labels. Expensive vacations, carefully documented on social media. But in reality, many millionaires don’t look anything like that. In fact, some of the wealthiest people quietly lived right next door, drove older cars, wore unremarkable clothes, and never once talked about money. Often, it wasn’t until they passed away that friends and family discovered just how much they had accumulated.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

What Is FAT FIRE And Why Is Everyone Talking About It?

If you’ve spent any time scrolling financial blogs, Instagram, or Reddit threads about retirement planning, you’ve probably run into the term FIRE, which stands for Financial Independence, Retire Early. The core idea of FIRE is simple:
Save aggressively, invest intelligently, and reach a point where your investment income supports your lifestyle, so you don’t have to work unless you choose to. But within the FIRE community, there are different flavors, and one common goal I hear is: FAT FIRE.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

Real Estate Isn’t as Passive as Everyone Says It Is

From an investor’s perspective, I can’t tell you how often I hear this phrase: “Real estate is passive income and the best way to build wealth.” Social media makes it look easy. Buy a property, collect rent, let tenants pay the mortgage, repeat. The problem is this. Most people dramatically underestimate the work, risk, and friction that come with owning real estate, and overestimate how “passive” it really is. Let’s talk honestly about what gets glossed over.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

The 2026 Super Catch-Up Contribution: A Second Chance to Turbocharge Retirement

If retirement is starting to feel real, but savings don’t quite look the way you hoped, 2026 brings some very good news. Thanks to the SECURE 2.0 Act, a new “Super Catch-Up” contribution becomes available starting in 2026, specifically designed for people in the final stretch before retirement. This could be one of your best saving years yet thanks to the expanded catch-up contribution rules. The change gives high earners and late savers a powerful opportunity to accelerate retirement savings during what are often peak earning years.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

You Maxed Out Your 401(k). Now What?

Maxing out your 401(k) is a big deal and something many people never quite get to. It means you’re earning well, saving intentionally, and thinking ahead. But once that box is checked, the next question almost always follows: “Where should the next dollar go?” The good news is that you have options. And the best choice depends on your income, family situation, tax picture, and what kind of flexibility you want down the road.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

Why Every Self-Employed Business Owner Should Consider a SEP IRA

If you’re a business owner or solo entrepreneur, retirement planning can feel like juggling flaming swords; figuring out how much to save, when you can save it, how much to reinvest back into your business, and how to minimize taxes all at the same time. That’s exactly where a SEP IRA can come in as one of the simplest and most powerful retirement tools available. A SEP IRA (Simplified Employee Pension Individual Retirement Account) is built for people who own their own business and want both tax savings today and tax-deferred growth for the future.

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Cassandra Smalley, CFA, CFP® Cassandra Smalley, CFA, CFP®

Google RSUs (GSUs): Making Smart Decisions With Your Equity Compensation

Working at Google (Alphabet) often means a competitive salary, great perks, and a significant portion of your compensation in Google stock — specifically, Restricted Stock Units, or GSUs (Google’s name for RSUs). These can be a powerful part of your financial life, but they come with rules and tax implications that are important to understand.

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