The T.I.M.E Blueprint: Navigating Taxes, Income, Money & Estate Planning with Oliver Asset Management

If you’ve switched jobs in the past few years, chances are you’ve got an old 401k sitting somewhere, collecting dust and possibly fees. Today, Frank answers a listener’s question about what to do with old 401ks, when a rollover might make sense, and how to avoid common pitfalls when making the switch. 

While it may seem harmless to leave your old 401k alone, that decision requires careful consideration, so stay tuned!  

Here’s what w...

Plenty of people have concerns about stock market volatility, a potential recession on the horizon, and worries for the economy amidst recent news. What if you’ve had 2025 marked on the calendar for a while as the year you plan to retire? Is this a bad time to do it? In this episode, Frank walks through five considerations near-retirees should weigh before hitting the eject button on work in 2025 and beyond.

Here’s what we discuss i...

Market volatility has a way of shaking confidence. It's easy to feel uncertain, but reacting without a plan could do more harm than the drop itself. In this special mailbag episode, Frank tackles timely listener questions about navigating today’s uncertain market.

Here’s what we discuss in this episode:

🧭 Why “stay the course” only works if you have a plan

⏳ What near-retirees should consider before locking in losses

🔍Could now ...

When the market is volatile, it's easy to feel like you're the only one who's ever felt this anxious. But some of the greatest investors in history have lived through chaos, and they left behind wisdom that still applies today. In this episode, Frank turns to voices like Warren Buffett, Benjamin Graham, and Jack Bogle to remind us how to stay grounded when everything feels uncertain.

Here’s what we discuss in this epi...

When markets are shaky, it’s tempting to pull your money out and “wait for things to settle.” But what if that instinct could cost you in lost growth? In this episode, Frank shares compelling statistics on what happens when investors miss the best days in the market, and how a few wrong moves could potentially reduce your long-term returns.

Here’s what we discuss in this episode:

📆 What can happen when you miss the best days in the ...

What happens when you make too much money to contribute to a Roth IRA? In today’s episode, we open the mailbag to answer a listener’s question about what tax-advantaged opportunities exist when a Roth isn’t on the table. Frank breaks down several smart alternatives that can still give you the tax-free growth you’re looking for, including backdoor Roth conversions and Health Savings Accounts (HSAs).

Here’s what we discuss in this epi...

Some investors like to do it alone, but is that the wisest path as retirement approaches? In this episode, Frank answers a listener’s question about whether DIY investing makes sense later in life. Sam has managed his own portfolio without an advisor or broker for years. But now he’s wondering if that approach holds up as the financial landscape gets more complicated.

Here’s what we discuss in this episode:

🛠️ What advisors see that...

Are HSAs good tax-advantaged accounts? Can you really accumulate funds over the years and use it tax-free in retirement? This is what listener Beth is wondering. She maxes out her HSA every year without touching it. We’ll discuss whether this strategy could be a smart move or if there are potential pitfalls to consider.

Here’s what we discuss in this episode:

💡 What makes HSAs unique 

📈 Why letting your HSA grow could pay off

🩺 Trac...

Tax season is here and it’s the perfect time to start planning for 2025 and beyond. In this episode, Frank dives into the key tax changes for 2025 that could impact your retirement strategy. From increased 401(k) contribution limits to standard deduction increases, Frank breaks down actionable strategies that could help maximize your tax savings this year and beyond.

Here’s what we discuss in this episode:

📈 The Standard Deduction: ...

Today’s topic comes from a question from Janice, who was recently laid off at 53 and is considering a career change into real estate. But to make it work, she may need to tap into her IRA to make ends meet. Could this put her long-term financial security at risk? 

Tune in to hear what Frank has to say from a financial advisor’s perspective. We’re breaking down the pros, cons, and alternative ways to fund a midlife career pivot witho...

April Fool’s Day is all about jokes and pranks, but when it comes to retirement planning, getting fooled can cost you real money. Today, we’re uncovering the beliefs that can fool retirees and pre-retirees into making bad financial moves. We’ll cover some of the most common myths that can damage your retirement plans and explain why they might not make much sense for you. 

Here’s what we discuss in this episode:

0:00 – Intro

2:11 – Th...

Many retirees and pre-retirees dream of owning a vacation home that they can visit throughout the year. But if you decide to make this move, how should you go about financing a second property? That’s the question one of our listeners, Ted, asked Frank this week. 

Should you take out a mortgage on the second home or tap into the equity of your primary residence? Or, could it be smarter to sell some investments and buy the property o...

We've got a great listener question for you today! This week, Barry shares that he has a life insurance policy through his job, as well as a whole life policy he purchased several years ago. Now, he’s wondering- does he really need both, or should he consider canceling one? 

Join Frank as he explores the many uses of life insurance beyond income replacement, from tax-free wealth transfer and estate planning to long-term care pr...

Social Security claiming strategies can vary greatly depending on family dynamics. This episode explores how different family situations, such as those with a stay-at-home spouse or a blended family, could impact when and how to claim Social Security benefits to maximize your retirement income.

Here’s what we discuss in this episode:

0:00 – Intro

1:10 – The broad view 

3:13 – Single-income household considerations 

6:36 – Blended family...

In today’s show, Rebecca asks an important question about retirement planning: With four different investment accounts- her 401(k), IRA, Roth IRA, and individual account- she’s wondering which one she should withdraw from first when she retires next year and needs income.

While many people default to withdrawing from their largest account, often the 401(k), without considering potential tax implications, Frank explains that the deci...

Financial mistakes can happen at any age, but they can have a particularly significant impact in your 60s. In today’s episode, Frank discusses 5 common financial blunders to avoid during this pivotal decade. 

Here’s what we discuss in this episode:

0:00 – Intro

0:55 – Ignoring retirement planning

3:10 – Failing to utilize tax benefits

5:26 – Failing to protect your assets

7:06 – Taking Social Security benefits without a plan

9:50 – Over o...

In today’s mailbag episode, we’re answering a question from Bobby about Social Security. He plans to keep working for another two years but wonders if he should start taking his benefits now since he’s reached full retirement age. Is it a smart move, or could waiting be a better strategy?

While everyone’s situation is unique, Frank will share how he helps clients determine the right time to start claiming benefits.

Here’s what we dis...

With the New Year comes New Year’s resolutions. While exercising more or eating better are common goals for folks as they try and start fresh in January, having a financial reset is a common resolution as well. 

We've ​got ​some ​financial ​changes ​that'll ​help ​you ​out, and ​some ​new ​mindsets ​and ​mentalities ​that'll ​put ​you ​in ​the ​right ​direction ​as ​you ​go ​through ​the new year. ​So ​don't ​wor...

A listener recently reached out, sharing that their house feels like a constant money pit. They're dealing with one repair after another, and the cost and effort are leaving them frustrated. They’ve asked Frank if he thinks it would be a bad idea to sell the house and rent while they figure out their next move.

If you're in a similar boat and are wondering whether renting again might be the right choice for you, ...