Matthew Bouthillette CFP, EA, Oak Leaf Wealth Management

10/13/2026

Scolding a person because they decided to work with someone else is not a good way to end a relationship, let alone operate a business

Recently onboarded a couple who decided to leave their current advisor at a very well-known firm; we will refer to the firm as a ‘big box’ firm

Despite working with their prior advisor for the last 15 years – they had one review meeting per year, and ZERO planning, sometimes the review meeting was just a phone call

The couple is in their mid-50s, they were referred by a friend to determine what type of retirement timeline they are on track, how they can be tax efficient today and down the road, and what they need to do to keep their estate plan in order

Here is what we did for them:
• Put together a retirement analysis that showed they are on track to not only retire at age 60, but even earlier if they wanted to
• Majority of their assets are in pre-tax accounts – we decided to shift where they are saving monies from their 401k plans to their taxable investment account and cash – this way they will have plenty of liquidity if they choose to retire at 57 or 58 (pre to 59.5)
o We ran the numbers to determine how much more we would need to withhold in taxes through payroll due to the decrease in tax savings via the 401k plan contribution
• Showed them how we could potentially do a combination of harvesting long-term gain and Roth conversions down the road to fulfil their goal of a tax efficient withdrawal plan, while also setting their kids up to inherit these accounts
• We would also be able to help simply their tax filing by partnering with our separate tax filing practice
• Referred them to a trusted P&C insurance agent who was able to update and in one case – UPGRADE their home and auto coverage, plus adding an umbrella policy – they were very much under insured for their net worth
• Walk them through the risks of their current investment allocation – as each account they had was the SAME EXACT ALLOCATION – 2 IRAs and 2 Roths – one taxable investment account - all the same funds and percentages
o Not only does this potentially duplicate risk, but this limits the power of asset location
 We suggested they change the Roths to 100% equity (no more bonds)
 While also creating differing strategies for each IRA account to balance risk, diversification, and distributions in a just a few years

• Reviewed their current estate plan to identify potential gaps, provided some education on what options are out there, put them in touch with our favorite estate planning firm to update documents and receive instructions to retitle accounts and beneficiaries’

Needless to say, our clients were not aware of all the opportunity to improve in all of these areas

With their permission we began onboarding and moving accounts over – they let their current advisor know about the move (this is not mandatory but a nice gesture)

The advisor completely freaked out on them, told them they were making a big mistake, that they were not aware of what they were doing, they would regret this, etc.

And to top it all off, after the couple mentioned some of the things we did for them – the advisor said ‘well we could have done that too, you just had to ask to me’

You hire experts to handle the details, educate you and create solutions

A client should not be expected to tell the advisor how to service clients and provide planning, that is the whole point of hiring an advisory team

It amazes me this type of behavior is still out there

Thank you for coming to my TED Talk 😊

This case study is for illustrative purposes only. Actual performance and results will vary. It does not constitute a recommendation as to the suitability of any investment for any person or persons having circumstances similar to those portrayed, and a financial advisor should be consulted for your specific situation.

10/12/2026

If you are a retiree and are at the mercy of the market during a decline - you probably were not allocated properly from the start - and panic selling during this turmoil could make the situation even worse

In most cases, you should not be anywhere close to 100% in equities if you are taking income from your portfolio

Positioning is everything with investing, but especially so when you are taking distributions

While you can certainly DIY your wealth management - at times it can do more harm than good

This post is intended for informational/educational purposes only and should not be construed as specific investment advice. Please contact your financial professional for more information specific to your situation.

10/12/2026

Selling your business is the finish line for one chapter — and the starting line for a much harder question: what now?

In this case study, we walk through an example client who sold their business for $10 million+ and came to us after the dust settled

He didn't need help getting the deal done. He needed help figuring out what to do with the outcome.

We cover:
• Tax-efficient withdrawal strategies
• Legacy planning
• Life after the exit - which is the part nobody prepares founders for:
o Replacing the identity, structure, and sense of purpose that running a business gave you

If you've sold a business — or you're planning to — this is the conversation that usually happens too late. We're having it now.

https://www.youtube.com/watch?v=7qOUNP7-b70

This is a case study for illustrative purposes only and should not be construed as a recommendation. It may not be representative of your experience.

Selling your business is the finish line for one chapter — and the ...

10/09/2026

Recently began working with a couple who has been contributing to ROTH IRAs for the last 10 years

Income is $400k+ - while reviewing their tax return it was clear they were over the Roth income limit for 2024 & 2025 - this led me to ask how long they have been married & how long they have earned this level of income - confirmed contributions for these years from their account statements

Turns out, they have been contributing to Roths while they have been over the MAGI income limits during the last 3 years - they had not realized this as the contributions are done automatically each month and life has been very busy - new home, family is growing, promotions

They decided to engage with our tax team to remove the excess contributions and determine any penalty implications – they will be filing taxes with our separate tax filing team, moving forward

Very important to plan accordingly and keep an eye on this type of stuff to avoid bumps down the road

Even if you are working with an advisor or CPA - I have seen situations where this type of issue still goes unnoticed for long periods of time

This case study is for illustrative purposes only. Actual performance and results will vary. It does not constitute a recommendation as to the suitability of any investment for any person or persons having circumstances similar to those portrayed, and a financial advisor should be consulted for your specific situation.

Tax preparation services through Oak Leaf Management Services, LLC are separate and unrelated to Commonwealth.

10/09/2026

ROTH CONVERSIONS ARE OVERRATED FOR THE MAJORITY OF RETIREES

When it comes to tax strategies as one is approaching retirement, Roth conversions are usually at the top of the list

In my opinion, for the majority of retirees – they ARE unnecessary.

Period.

In most cases it does not create any tax efficiency; especially if your portfolio is your primary income source

Advisors love to talk about this as a strategy because it does sound very appealing, but more often than not it is a nifty marketing tool, than adding value

Let’s start at the beginning:

When it comes to tax strategies as one is approaching retirement, Roth conversions are usually at the top of the list. In my opinion, for the majority of retirees – they are unnecessary. Period.

10/08/2026

Don’t believe everything you read or so, especially online

Social media and social circles can be very powerful tools in making folks feel that they are ‘behind financially’ or ‘missing out on life’

I recently began working with clients in their mid 40s that have amassed a $5 million+ net worth, mortgage almost paid off, well on track to retire early, if they wanted to

One spouse recently transitioned jobs and now has a very generous equity comp plan – RSUs and NQSOs to start – potential for ISOs down the road

This is going to have implications on both their cash flow AND tax picture

We went through our analysis from A-Z covering all arears vital for their planning – in the end, they both mentioned that it was calming to confirm they have been doing the right things, because they felt very behind, especially when they chat with co-workers

What we see online, or hear from friends, co-workers, etc., often does not tell the whole story
In some cases, it may appear someone is doing well financially – fancy trips, cars, private school, large house, but in reality, these folks just have a strong income, they do not have the assets to fall back on. The majority of this is funded by debt and payments

One of my favorite authors, Morgan Housel, talks about this dynamic as being rich (strong income, lots of ‘stuff’) vs. wealthy (financial stability, resources to fall back on)
Everyone’s situation is vastly different based on your values, lifestyle choices, upbringing, career path, etc.

• Take time to inventory your current situation
• Have a discussion with your spouse about your goals, values, future plans – how you want your life to look
• Develop an action plan - work with someone who can understand your compensation plan and help you maximize it, and minimize taxes
• Follow it as best you can
• Make adjustments as life evolves
• If you’d like help, engage a CFP® professional who shares similar ideas, thoughts, strategies, who can help you stay on track

Life is too short to worry about what others are doing

This case study is for illustrative purposes only. Actual performance and results will vary. It does not constitute a recommendation as to the suitability of any investment for any person or persons having circumstances similar to those portrayed, and a financial advisor should be consulted for your specific situation.

10/07/2026

Client is retiring in November - they are in their mid-70s - they have been over the RMD age for some time

They have not had to take an RMD as they are active in their 403b plans (only plan they have)

Client wanted to understand costs and benefits of taking their RMD for 2026, or waiting until 2027 to take one for 2026 and one for 2027 - as they could wait up until end of March 2027 to take their RMD for 2026

Ran a tax analysis that factored in income through the summer, spouse still working, S.S. income (currently collecting), factoring in spouse turning on S.S. next year - no surprise it showed that the client is better off taking in 2026 then 2027, but the numbers were still close (a few thousand difference) given all the factors mentioned

This led to weighing changing the spouses' current contributions from Roth to Pre-Tax, or potentially increasing currently Roth contributions to not leave the kids / grandkids with a tax bomb, assisting with education costs, etc. while the clients understanding this may not exactly help them with taxes today

Many decisions seem simple on the surface, but digging in can truly identify opportunities, efficiencies, and chances to add value to the next generation - the 'best' answer in these types of situations may not always be mathematically sound, and that is perfectly OK

This case study is for illustrative purposes only. Actual performance and results will vary. It does not constitute a recommendation as to the suitability of any investment for any person or persons having circumstances similar to those portrayed, and a financial advisor should be consulted for your specific situation.

10/06/2026

It can be so easy to get wrapped up into ‘what everyone else is doing’

In a world powered by social media, it can feel like you are ‘behind’ or not doing ‘enough’ when in reality, you are doing just fine and aligning with YOUR plan

Recently had a conversation with a new client that reminded them they are doing just that

In their early 50s, $4 million net worth, only debt is their mortgage (small balance), no car loans, no student loans, no credits card debt, paid for their children’s college education, on track to retire in their late 50s if they wanted to

Don’t let the appearance of travel posts on social media, large home purchases etc. cloud what you are doing

Develop a plan that aligns with YOUR goals, implement, stay the course – enjoy life

10/05/2026

Do you find yourself wondering how you can reduce taxes and fulfill your Required Minimum Distribution if you do not need the money?

Qualified Charitable Distributions (QCD’s) - a great way to fulfill a charitable inclination and potentially minimize taxes in the process using pre-tax dollars

Here is a high-level breakdown:

You become eligible for a QCD when you attain age 70 ½ - under current laws you and your spouse can both contribute up to $111,000 a year in QCD’s.
So, for a married couple, this could be up to a potential $222,000.

So, when and how does this come into relevance?

Most folks consider this strategy when they reach their Required Minimum Distribution age (RMD) - age 73 if born prior to 1959 & age 75 if born 1960 or later under current laws -

For example, let’s say that a person is living comfortably on their non-IRA assets and Social Security (or a pension), meaning they may not need their RMD for income purposes, and taking it could mean paying more in taxes. Let’s assume the RMD is $50k for the year.

So, instead of taking the RMD for income purposes, they could consider utilizing the QCD strategy to give their RMD of $50,000 directly to the charity of their choice.

In doing so, the amount allocated to the QCD satisfies the person’s RMD for the year, and removes it from income, meaning no tax liability is owed.

Even more, the individual does not need to be itemizing deductions (vs. taking the standard deduction) to take advantage of this tax break

Pretty cool right? In addition, some financial institutions actually allow the account holder to have check writing ability from their IRA, which can simplify this process. The individual does just need to make sure they file the correct forms with their tax return to properly record this transaction.

This type of planning is certainly NOT for everybody, but for the appropriate situation - this can be a very impactful way to make a large gift to a charity of your choice, satisfy your RMD, and reduce your potentially taxable income in the process

10/02/2026

The financial and emotional shift that comes with a life transition like retirement can be daunting

Using the nest egg you've built up — and never touched — over the past 30-40 years for income is not an easy pill to swallow

Most people struggle not just with figuring out a withdrawal rate, but with understanding how their investment allocation actually needs to change

Although, sometimes, it doesn't have to change the way most people think

In my experience, people assume that once they're in the final stretch of work heading into retirement, they need to get very conservative with their investments

If they were 80% stocks / 20% bonds and cash, now they think they need to move to 60/40, or 50/50, and so on

For the clients we serve, I mostly disagree with that adjustment as a blanket rule of thumb, for a few reasons:

Using the nest egg you've built up — and never touched — over the past 30-40 years for income is not an easy pill to swallow. Most people struggle not just with figuring out a withdrawal rate, but with understanding how their investment allocation actually needs to change.