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The Blind Spots That Cost DIY Investors Thousands

Andy Keeler headshot

Andy Keeler.
April 17th, 2025 | 13 min read

Financial Opportunities Uncovered Hosted by Andy Keeler   

Executive Summary: Why Even the Smartest DIY Investors Need Professional Financial Planning

In this episode of Financial Opportunities Uncovered,

Financial planning is like a system of interconnected gears—turn one, and several others move with it. While many people take pride in managing their own investments, this “do-it-yourself” approach often misses the bigger picture, leading to costly oversights and missed opportunities.

In our latest episode of the Financial Opportunities Uncovered podcast, Mark Beaver, CFP®, joins Andy Keeler to share real-world stories that reveal why even the most sophisticated DIY investors—doctors, lawyers, CPAs, and retired investment bankers—eventually turn to professional financial guidance.

Hidden Costs of Going It Alone

One of the biggest blind spots for DIY investors is tax planning. Mark explains how active trading in taxable accounts can trigger unexpectedly high tax rates—and even increase Medicare premiums.

In one case, a client unknowingly paid 37% on investment gains when, with proper planning, they could have paid only 15%.

This isn’t just about saving money but protecting your long-term financial security.

Beyond Taxes: The Overlooked Details

Financial planning goes deeper than investments and taxes. Mark and Andy dig into:

  • Estate planning pitfalls like unfunded trusts.
  • Retirement income sequencing and how the order of withdrawals can drastically change outcomes.
  • The challenge of keeping up with evolving strategies across tax law, markets, and estate planning.

As Mark puts it:

“It’s not just the decisions you make, but the opportunities you miss because you didn’t know they existed.”

Why Smart Clients Delegate

The most successful professionals don’t hire a financial advisor because they can’t manage money—they do it because they prioritize peace of mind.

One client summed it up perfectly: he wanted his wife cared for in his absence, valued the holistic perspective Keeler & Nadler provides, and knew he couldn’t keep up with the financial landscape across multiple disciplines.

By delegating, he gained something far more valuable than potential cost savings: confidence, time, and clarity for his retirement years.

The opinions expressed in this program are for general informational purposes only and are not intended to provide specific advice or recommendations.

It is only intended to provide education about finance, tax, retirement and related planning topics. To determine which investments or strategies may be appropriate for you, consult your financial, tax or legal advisor prior to implementing. Any past performance discussed during this program is no guarantee of future results.

Any indices referenced for comparison are unmanaged and cannot be invested into directly. As always please remember investing involves risk and possible loss of principal capital; please seek advice from a licensed professional.

Keeler & Nadler Family Wealth is a registered investment adviser. Advisory services are only offered to clients or prospective clients where Keeler & Nadler Family Wealth and its representatives are properly licensed or exempt from licensure. No advice may be rendered by Keeler & Nadler Family Wealth unless a client service agreement is in place.

Podcast Transcript: Financial Opportunities Uncovered

Andy Keeler: 0:03
If you are a financial do-it-yourselfer, today's episode is a cautionary tale. Perhaps you love investing, whether that's investing in individual stocks or taking a bit more passive and diversified approach by investing in mutual funds or ETFs. But beyond the fun of managing your own portfolio, have you left yourself exposed in other areas? Today, on Financial Opportunities Uncovered, we literally uncover the risks and pitfalls of doing your own financial planning. To help share some of the reasons so many of our sophisticated clients have turned over their wealth management to us is Mark Beaver, CFP®, a senior financial advisor here at Keeler & Nadler and one of our regular guests. How's it going?

Mark Beaver: 0:53
Doing great. Our kids are back in school, so we're happy campers.

Andy Keeler: 0:57
My son's heading to college, so I don't know whether we'll be celebrating or crying. Keeping the box of tissues handy—good idea. Go Bearcats.

Andy Keeler: 1:12
So the inspiration from this episode comes from a common interaction I have with folks when they find out what I do for a living. The interaction goes something like this: “So you're a financial advisor? I love managing my own money now that I'm retired. I read a lot. I really enjoy it.” Given that my financial planning brain is hard to turn off, a rush of questions come to mind. But no matter the questions or the order in which I ask them, inevitably the answer is the same: “Yep, I've done that. Yep, I have an estate plan. Yep, we've taken care of that.” Basically, our innate overconfidence kicks in. We covered that in the episode called Why Smart People Make Dumb Bets. Anyway, Mark, can you share a scenario or two where a prospective client had all the answers, some of which proved to be dead wrong?

Mark Beaver: 2:02
Definitely can. One thing that comes to mind is that many DIYers have experienced a bad version of advice somewhere down the line. Unfortunately, in our industry, the term “advisor” is used way too loosely. So it’s not consistent that everybody is providing the same level of value. Often that leads people to think they’d be better off going it alone. But almost every time I’ve come across a DIYer, there’s at least one piece of the puzzle missing. They might have the right concept, but miss a nuance that has big impacts—especially on taxes.

Andy Keeler: 4:19
I remember a few years ago you had a client with a very active strategy—options trading, constant reallocations. It sounded sophisticated. How did that work out for them?

Mark Beaver: 4:54
They wanted conservative returns, 3–4%. The strategy achieved that on the surface, but they ignored tax implications. It was a taxable account, so their real net return was closer to 2% after taxes. A simple CD could have achieved the same without complexity—or extra cost. Worse, they were unknowingly generating short-term capital gains taxed at ordinary income rates, often 35–37%. That’s thousands in avoidable taxes.

Andy Keeler: 8:39
That’s the problem—people judge success by returns without considering risk or tax drag. A 20% gain sounds great until you compare it to the market or account for taxes. Even sophisticated clients—doctors, lawyers, CPAs, retired bankers—can miss these details. They delegate to us not because they’re incapable, but because they want peace of mind and don’t want to miss opportunities.

“It ain’t what you know that gets you into trouble. It’s what you know for sure that just ain’t so.” — Mark Twain

Mark Beaver: 13:28
Exactly. Even highly intelligent people only do part of what’s needed. Delegation frees them to focus on what matters, while we make sure all the gears of their financial life—investments, taxes, estate planning—are working together. Small oversights can compound into big costs. Outsourcing isn’t a cost, it’s an investment in peace of mind.

Andy Keeler: 22:33
Like an antique timepiece—every gear affects another. That’s financial planning. Thanks, Mark. And thank you to our listeners for joining us on Financial Opportunities Uncovered.

Disclaimer: The opinions expressed in this program are for general informational purposes only and not intended to provide specific advice or recommendations. Investing involves risk, including the possible loss of principal. Consult a licensed financial, tax, or legal advisor for personalized guidance.