James Leblo

06/15/2026

Most people think beneficiary planning is simple. Name someone, move on. It’s not. The account type matters more than most individuals realize.

Here’s a quick breakdown of how different accounts pass to heirs:

1) Taxable Brokerage Accounts

Heirs typically receive a step-up (or potential step-down) in cost basis to the date-of-death value. A $500K account with a $100K original cost basis? The embedded gain essentially disappears. A step-up in cost basis can be a valuable estate-planning consideration, depending on the investor’s situation and current law.
(Source: IRS – Publication 551, Basis of Assets)

2) Roth IRAs

Generally pass income-tax-free to beneficiaries if certain requirements are met (5-year rule). Under the SECURE Act’s 10-year rule, many non-eligible designated beneficiaries must withdraw the account within 10 years; withdrawals are often income-tax-free for qualified Roth IRAs, but exceptions and state tax treatment can vary.
(Source: IRS – Publication 590-B; SECURE Act of 2019)

A Roth left to a high-income beneficiary is a radically different outcome than a traditional IRA.

3) Traditional IRAs & 401(k)s

This is where I see the most planning gaps. Pre-SECURE Act, “stretch IRA” distributions could span a beneficiary’s lifetime. That’s gone for most non-spouse heirs.

Now the rules generally say:
• Non-eligible designated beneficiaries (most adult children) must empty the account within 10 years
• If the original owner died after their required beginning date, annual RMDs are also required during those 10 years, not just a lump sum at year 10
• This can stack significant ordinary income on top of a beneficiary’s existing earnings
(Source: IRS Final RMD Regulations, 2024; SECURE Act of 2019)

The tax exposure here is real. A $1M inherited traditional IRA distributed over 10 years is, in many cases as ordinary income, no capital gains treatment, no step-up in basis.

Coordinating which assets go to which heirs can be an important planning conversation. Understanding these rules can help families make more informed decisions based on their individual goals and objectives.

06/12/2026

Diversification vs. “Owning a Bunch of Stuff”

One of the biggest misconceptions I see in personal finance is the belief that owning a lot of different investments automatically means you’re diversified.

Here’s the truth:
👉You can hold 25 different positions and still have a portfolio that moves like you only own one.
👉 Diversification isn’t about quantity of holdings, it’s about the correlation of those holdings.

I often see investors who feel protected because they own multiple mutual funds, ETFs, or individual stocks, but when you look deeper, everything is tied to the same risk:
• All large‑cap U.S. tech
• All growth‑biased funds
• Overlapping ETFs holding the same top positions
• Multiple mutual funds built around the same style or sector

That’s not diversification. That’s duplication.

True diversification spreads risk across investments that don’t behave the same way at the same time. That means being intentional about exposure to things like:
✔ Different asset classes
✔ Different sectors
✔ Different geographical holdings
✔ Different styles
✔ Different risk profiles
✔ Different economic drivers

When one part of your portfolio zigs, another part should reasonably zag.

06/10/2026

Ever Notice How Much of Your Wealth Depends on One Company?

One risk I see often with highly compensated professionals is concentration risk. Especially when compensation includes RSUs or stock options, and a large portion of the 401(k) is invested in employer stock as well.

On paper, it may look great:

- You believe in the company and its future plans
- The stock has performed well
- It feels “safe” because it’s familiar

But where's the blind spot:

During periods of turbulence, it can simultaneously affect your :

• Income
• Equity compensation
• Retirement savings

RSUs and company stock already create a built in overweight exposure to a single company. When employer stock also dominates the 401(k), your long‑term financial outcome becomes highly dependent on one company’s future whether you intended that or not.

This doesn't mean that employer stock is “bad.” All it means is that it needs to be managed intentionally, not left on autopilot.

The professionals who navigate this well tend to:

✅ Understand how much of their net worth is tied to one company
✅ Separate loyalty from portfolio construction
✅ Create a plan for diversification that aligns with taxes, cash flow, and long‑term goals

Awareness is the first step. Strategy is the second.

06/06/2026

Do you hold a large amount of your employer’s stock in your retirement plan?

If so, there’s a powerful tax concept you should at least be aware of:

Net Unrealized Appreciation (NUA)

Many professionals accumulate significant company stock through RSUs, ESPP, stock options, or employer retirement plans—often without realizing how concentrated that exposure becomes over time.

Here’s where NUA may come into play:

NUA is a tax strategy that can apply to employer stock held inside a 401(k) or similar plan. Instead of rolling those shares into an IRA at retirement or separation, eligible individuals may be able to:

- Distribute the stock “in-kind”
- Pay ordinary income tax only on the original cost basis
- And potentially have the growth taxed later at long‑term capital gains rates, instead of ordinary income

Why this matters:

Employer stock + retirement accounts = built‑in concentration risk
Taxes can quietly become one of your largest retirement expenses
Once you roll everything into an IRA, NUA is usually off the table

Here are some of the most common mistakes I individuals make:

1️⃣ Rolling employer stock into an IRA without evaluating NUA. Once company stock is rolled into an IRA, NUA is gone permanently. Many people do this automatically, not realizing they’ve given up potential long‑term capital gains treatment on years of appreciation.

2️⃣ Assuming NUA applies to RSUs or ESPP shares held outside the plan. NUA generally applies to employer stock inside a qualified retirement plan (like a 401(k)). RSUs and ESPP shares held in brokerage accounts follow very different tax rules.

3️⃣ Ignoring concentration risk because of tax benefits. NUA can improve tax efficiency, but it doesn’t reduce investment risk. Holding too much company stock—before or after an NUA transaction—can still expose your financial plan to unnecessary volatility.

4️⃣ Not coordinating timing with retirement or separation from service. The NUA rules are highly specific. The wrong order of transactions or poor timing can disqualify the strategy entirely—even if you otherwise would have been eligible.

The key takeaway:

NUA is not for everyone, and the rules are very specific. You must take into account all information such as the immediate tax bill on the cost basis, your unknown tax bracket whether higher or lower in your distribution years (long term captial gains rate vs ordinary income rae), timing mistakes, and concentration risk.

For some individuals with large company stock positions, it can be an impactful planning opportunity once the numbers are laid out side by side.

Before making a rollover or retirement decision, make sure you understand all of your options first.

06/05/2026

Markets continued their upward climb in May, supported by strong technology performance, positive economic data, and ongoing diplomatic efforts in the Middle East. The Nasdaq gained 8.36%, the S&P 500 rose 5.15%, and Canada’s S&P/TSX Composite added 2.37%, while investors welcomed better-than-expected job growth and upbeat corporate earnings. With the Fed's next meeting scheduled for June, attention is turning to updated economic projections and what they may signal about the broader economy. From \$24 billion spent on Father's Day to the popularity of dining out and special outings, this month's by-the-numbers highlights how families celebrate the dads in their lives.

Monthly Market Insights | June 2026 U.S. and Canadian Markets Stocks pushed higher in May, fueled by big tech names, positive economic news, and ongoing diplomatic efforts in the Middle East. The Nasdaq Composite, which rose 15.29 percent in April, tacked on another 8.36 percent. The Standard & Poor...

06/02/2026

Defined Benefit vs. Defined Contribution Plans — What Business Owners Need to Know:

Most business owners are familiar with 401(k)s and other defined contribution (DC) plans — but far fewer realize how powerful defined benefit (DB) plans can be for accelerating retirement savings and reducing taxes. If you’re a business owner looking to supercharge your long‑term strategy, here’s a simple breakdown.

Defined Benefit Plans: The Powerhouse Option for Owners

Defined Benefit Plans (including Cash Balance Plans) allow business owners to contribute far more than what is allowed under a 401(k), SIMPLE IRA, or SEP, often multiple six figures per year, depending on age, income, and plan design.

Key Benefits for Business Owners

- Massively Higher Contribution Limits

DB plans allow substantially larger annual contributions. Ideal for those wanting to “catch up” quickly or compress decades of savings into 10–15 years.

- Big Tax Deductions

Contributions are typically fully tax‑deductible to the business.
This makes DB plans one of the strongest tax‑reduction tools available to entrepreneurs.

- Predictable Income in Retirement

Instead of a fluctuating balance, DB plans promise a targeted retirement benefit. Great for owners who want guaranteed outcomes rather than market-dependent results.

- Works Extremely Well With a 401(k)

A DB plan + a 401(k)/profit-sharing plan creates a dual-plan strategy that maximizes both flexibility and tax efficiency.

Most business owners don’t realize they can contribute far more toward retirement than what a 401(k) allows. A properly designed DB plan can transform your tax strategy and retirement timeline, especially when combined with a DC plan.

05/28/2026

“What if you’ve saved too much in your child’s 529 plan?”

It’s a great problem to have, but it’s still a problem that needs a strategy. Overfunding a 529 plan can happen if your child gets scholarships, chooses a less expensive school, or doesn’t use all the funds for education. So, what are your options?

✅ Change the Beneficiary

You can transfer the funds to another family member who might need education dollars—siblings, cousins, even yourself if you plan to take courses.

✅ Roll Over to a Roth IRA

Thanks to recent rule changes, you may be able to roll unused 529 funds into a Roth IRA for your child. The account has to be old enough (15 years) and you can only move money that has been in the account for at least 5 years. There is also a lifetime cap of $35k per person. This can turn leftover education savings into a powerful retirement tool.

✅ Withdraw and Spend

You saved it! You can take the money out for non-education purposes. Is it tax efficeint, no. You’ll pay taxes on the earnings and a 10% penalty—but sometimes that’s worth it depending on your goals.

The key is to plan ahead and understand the implications of each choice

05/27/2026

I had a client recently tell me, “I know I need to do something, I just can’t bring myself to do it.”

This isn't laziness. It isn't a lack of discipline. It was decision paralysis and it’s one of the most quietly damaging forces in the financial planning industry.

We live in a world that demands constant change. New tax laws. Changing interest rates. Market volatility. A flood of financial products, apps, and advice pulling us in every direction. And after a while? The brain just stops as it becomes overwhelmed.

This is the fear of change and it’s very real. When people are overwhelmed by how much has already shifted in their lives, even a beneficial financial decision can feel like one change too many.

The result:

→ The retirement account that never gets opened
→ The will that’s been “almost finished” for three years
→ The debt consolidation plan that stays a plan
→ The investment that keeps getting pushed to “next month”
→ The coverage to protect assets and loved ones that never gets put in place

Not deciding IS a decision. And often, it’s the most expensive one you’ll make. The gap between where you are and where you want to be doesn’t close on its own.

The solution to paralysis isn’t motivation. It’s a small first step. You don’t have to overhaul your entire financial life this week. You just have to take one action. Have a converation and make one decision at time.