Derek Carmichael, Financial Advisor - Stifel

Derek Carmichael, Financial Advisor - Stifel From the Classroom & Ballfield to Your Financial Game Plan — Helping Athletes, Educators, and Families navigate their financial journeys.

Happy 4th of July! Our offices are closed on Friday, July 3rd in observation.
07/03/2026

Happy 4th of July! Our offices are closed on Friday, July 3rd in observation.

📅 Happy Bobby Bonilla Day 💰⚾Every July 1st, Bobby Bonilla gets paid $1.19 million by the New York Mets… despite not play...
07/01/2026

📅 Happy Bobby Bonilla Day 💰⚾
Every July 1st, Bobby Bonilla gets paid $1.19 million by the New York Mets… despite not playing for them since 1999.
Sounds like a joke—but it's one of the most iconic financial decisions in sports history. And there's a real lesson in it for all of us.

💡 What actually happened?
Instead of paying Bonilla ~$5.9M upfront, the Mets agreed to defer payments starting in 2011 through 2035—with interest.
Why? At the time, ownership believed they could invest that money and earn higher returns (spoiler: it didn't quite work out as planned).

📈 The Financial Literacy Lesson
Bobby Bonilla Day is more than a meme—it's a masterclass in a few key principles:
1. The Power of Compounding
Bonilla effectively turned ~$5.9M into nearly $30M total payouts over time.
Time + interest = serious wealth-building potential.
2. Time Value of Money
A dollar today isn't the same as a dollar tomorrow.
Bonilla bet on future dollars growing—and structured the deal accordingly.
3. Cash Flow > Lump Sum (Sometimes)
Consistent, predictable income streams can provide:

Stability
Budgeting advantages
Reduced risk of overspending

Think: pensions, annuities, or structured withdrawals.
4. Investment Risk Matters
The Mets assumed they could outperform the interest rate tied to Bonilla's deal. When that didn't happen, the contract became… legendary.

🔁 Real-World Takeaway
Whether you're an athlete, business owner, or everyday investor:
👉 Structuring when and how you receive money can be just as important as how much you earn.

🎯 So today, while Bobby gets paid, it's worth asking:
Are your financial decisions working for you long-term… or just today?

espn.com

Your 401(k) is often your largest retirement asset.But many people set it up… and never revisit it.Small improvements—li...
06/22/2026

Your 401(k) is often your largest retirement asset.
But many people set it up… and never revisit it.
Small improvements—like proper allocation, rebalancing, and staying disciplined—can make a meaningful difference over time.

amazonaws.com

👉 A 29-Point Comeback is Amazing… Unless It's Your Retirement PlanThe Knicks just pulled off a historic 29-point comebac...
06/18/2026

👉 A 29-Point Comeback is Amazing… Unless It's Your Retirement Plan

The Knicks just pulled off a historic 29-point comeback… and it was incredible to watch.

Games like that remind us why we love sports — resilience, belief, grit, and the ability to flip the script when everything looks lost.

But here's the reality…

In retirement planning, you generally don't want to be the team down 29.

Because while a comeback makes for a great story, it can also mean:

- Getting a later start than planned
- Falling behind on savings goals
- Taking on more risk to try to catch up
- Hoping for a strong finish to make things work

That's not a comfortable position to be in.
In many cases, strong financial outcomes come from simple, consistent habits over time:

💰 Pay yourself first
Prioritizing savings early can make a meaningful difference.

📈 Automate your investments
Consistency over time can help reduce the impact of emotions and timing.

🏦 Contribute to workplace retirement plans (like a
401(k))
Especially when employer matches are available.

🧾 Consider IRAs / Roth IRAs
They can play a role in building long-term, tax-aware strategies.

⚖️ Maintain an appropriate asset allocation
Aligned with your goals, time horizon, and risk tolerance.

While comeback stories are exciting in sports,
financial planning is often less about dramatic moments and more about steady progress.

Enjoy the comeback stories.

But when it comes to your future
the goal is to build a plan that doesn't rely on one.

yahoo.com

Myles Garrett's Trade Is a Reminder That Wealth Isn't About What You Make—It's About What You KeepWhen news broke that N...
06/05/2026

Myles Garrett's Trade Is a Reminder That Wealth Isn't About What You Make—It's About What You Keep
When news broke that NFL superstar Myles Garrett was traded from Cleveland to Los Angeles, most people focused on the football implications.

As a an advisor, I immediately thought about something else:

Taxes.

Garrett's paycheck may remain enormous, but where that paycheck is earned can have a significant impact on how much of it he actually keeps.

And that's a lesson that applies far beyond professional athletes.

The Wrong Question
Most people focus on one number:

"How much did he sign for?"

Investors do the same thing.

They ask:

What's the return?
What's the yield?
How much did the stock go up?
How much income does the portfolio generate?
Those are important questions.

But they're often not the most important question.

The better question is:

How much do you keep after taxes?

A Million-Dollar Difference
California has one of the highest state income tax rates in the country. Ohio's rates are considerably lower.

For someone earning millions of dollars per year, a change in location can mean a massive difference in after-tax income.

The same principle applies to investors.

Two people can earn the exact same investment return and end up with dramatically different outcomes depending on how their investments are structured and taxed.

One investor focuses solely on returns.

The other focuses on after-tax returns.

Over time, the second investor often wins.

The Silent Performance Killer
Many investors obsess over finding an investment that can outperform by 1% or 2%.

At the same time, they ignore taxes that may be costing them far more than that every year.

Taxes are often one of the largest expenses investors will ever pay, yet they receive far less attention than market performance.

That's why tax planning is not a once-a-year activity.

It's a year-round wealth-building strategy.

Good Financial Planning Isn't Just Investment Planning
When people think of financial advisors, they often think about stocks, bonds, and portfolio performance.

But some of the most valuable conversations happen outside the investment portfolio.

Questions like:

Should I do a Roth conversion?
Which account should I withdraw from first in retirement?
How should I structure charitable giving?
When should I take Social Security?
How can I reduce future Required Minimum Distributions?
How do I position assets to create the most tax-efficient income stream?
These decisions can potentially save tens or hundreds of thousands of dollars over a lifetime.

The Real Scoreboard
Myles Garrett's trade is a reminder that earning more money doesn't automatically mean building more wealth.

Whether you're an NFL player, a business owner, an executive, or a retiree, the goal isn't simply to maximize income.

The goal is to maximize what stays in your pocket.

Because at the end of the day, wealth isn't measured by what you earn.

It's measured by what you keep.

nypost.com

Congratulations to the class of 2026!Now that you are stepping into the ‘adult world', explore our Financial Literacy Vi...
05/19/2026

Congratulations to the class of 2026!

Now that you are stepping into the ‘adult world', explore our Financial Literacy Video Series to help build confidence and take control of your financial future:
https://vimeo.com/showcase/stifel-financial-literacy

Address

3951 Convenience Circle NW Suite 200
Canton, OH
44718

Telephone

+13305968116

Alerts

Be the first to know and let us send you an email when Derek Carmichael, Financial Advisor - Stifel posts news and promotions. Your email address will not be used for any other purpose, and you can unsubscribe at any time.

Contact The Business

Send a message to Derek Carmichael, Financial Advisor - Stifel:

Share