Boyd Wealth Management

08/11/2026

One of the most common questions I hear isn't about AI, interest rates, or the next recession.

It's some version of:

“I know I need to invest the money… I just don’t want to invest it at the worst possible time.”

It's a fair question. Especially if you've recently sold a business or a piece of real estate, inherited money, or built up a larger cash balance than you intended.

So I wrote a story about Unlucky Larry.

Larry has the worst market timing in history. He invested in the S&P 500 just before the Great Depression.

Just before Black Monday.

Just before the dot-com crash.

Just before the Global Financial Crisis.

Just before COVID.

Yet over the long run, his results were surprisingly strong.

The lesson isn't that market declines don't happen. They do.

It's that history suggests the fear of investing at an all-time high has often been a larger obstacle than the all-time high itself.

If you've ever worried about investing at the "wrong" time, I think you'll enjoy Larry's story.

Worried about investing at an all-time high? Meet Unlucky Larry and learn why history suggests patience has often mattered more than perfect timing.

06/17/2026

Feeling a little left out of the SpaceX IPO?

That’s normal. Big IPOs tend to come with big headlines, big demand, and a very natural feeling that everyone else (but you) got invited to the party.

The data may help.

Looking at the largest U.S.-listed IPOs with a full first year of trading, the average first-year return was -9.88%, and 10 of 14 finished lower than their first-day close. The average first-year drawdown was nearly 50%.

There were winners. Arm was the standout. But that is the point. Outcomes were widely dispersed, and the strong performers were the exception, not the rule.

And even if you feel like you “missed” the IPO, there’s a decent chance you may own a small piece of SpaceX eventually through a diversified index fund, depending on which index you own and whether SpaceX meets that index’s inclusion rules.

That may turn out to be a good thing. It may not.

Either way, in a diversified ETF, it would likely be one small holding inside a much broader plan.

IPO excitement is not the same thing as investment discipline.

Sometimes the best move is accepting that you do not need access to every opportunity. You need a plan, a process, and the patience to let time do some of the work.

Boring, admittedly. But boring has a pretty good long-term batting average.

05/12/2026

I’ve been getting asked two versions of the same question lately:

“How do you think about AI and the future of financial advice?”

Or said more directly, “Will AI replace you?”

Honestly, I don’t take the threat lightly at all.

Things are changing incredibly fast, and I think anyone in professional services who dismisses AI is probably underestimating what’s coming.

That said, I also think there’s a more nuanced outcome than “financial advisors disappear.”
I think future clients will show up far more informed than ever before.

They’ll use AI to:
• learn financial concepts
• build rough draft financial plans
• generate smarter questions
• compare strategies
• and better understand what good advice should look like.

And frankly, I think that’s a good thing.

More informed clients will likely separate great advisors from conflicted product salespeople or shallow planning shops.

The “information advantage” in our industry is shrinking quickly. But real financial planning was never just about information.

It’s about judgment.
Prioritization.
Implementation.
Coordination.
Behavior.
Tax awareness.
Follow-through.

A family can have a sophisticated financial plan on paper and still make costly mistakes if nobody implements it correctly:
• beneficiaries never updated,
• taxes triggered unintentionally,
• Roth opportunities missed,
• portfolios unmanaged,
• estate documents disconnected from reality,
• emotional decisions made during stressful markets.

AI can help generate a checklist.

But someone still has to connect all the dots and help execute thoughtfully over time.

I also think AI will empower a certain type of highly capable do-it-yourself investor in ways we’ve never seen before. Some people absolutely will benefit from that.

But for many successful families and business owners, the challenge was never just access to information.

It was turning complexity into clarity, then consistently making good decisions year after year.
That part still matters.

Maybe more than ever.

04/22/2026

Everyone has one.

A friend, relative, business partner, or “smartest person I know” who shows up during a scary market event and says:

“This is bad. It’s going to get worse. You should sell everything and go to cash.”

They usually mean well.

The problem is they rarely know your full financial picture, your goals, your tax situation, your time horizon, or why your portfolio was built the way it was in the first place.

They are reacting to headlines.
Your plan was built around your life.

That’s a big difference.

I’ve seen this happen during wars, bank failures, recession scares, and plenty of other moments that felt like the beginning of the end.

In those moments, abandoning a thoughtful plan can feel smart. It can feel prudent. It can feel like you’re doing something.

But often it’s just fear with better marketing.

A good financial plan is supposed to account for uncertainty. That’s the point of proper diversification, cash reserves, risk alignment, and long-term thinking.

So here’s a simple rule:

If someone tells you to make a major change to your portfolio during a scary moment, pause before you act.

Review the plan.
Get context.
Talk to the person who actually knows your situation.

A lot of investing damage does not come from bad headlines.

It comes from bad reactions.

Perspective is underrated. Process is boring. Patience is hard.

Fortunately, those three things still work.

Trying to jump in and out during stressful periods is a dangerous game, because the recoveries can be fast and unpredictable.

Even positive years in markets come with down days, weeks, and months.

04/07/2026

Investors have always climbed a wall of worry, and Q1 2026 added a few more bricks.

AI overspending.
AI disruption.
Private credit concerns.
Iran and oil.

Plenty to worry about, as usual.

And yet a sample globally diversified 60% stock/40% bond portfolio was down just 1.85% for the quarter, even with the S&P 500 down 4.33%.

The risks are real. They always are. It’s just a reminder that perspective, discipline, and diversification still matter.

03/25/2026

Even people with $10 million still wonder if they have enough.

Sounds odd, but I see it all the time. Successful people, plenty of assets, no real financial stress day-to-day… and still a lack of confidence.

Can we take the BIG trip? Should I slow down at work? Is my portfolio durable enough to hold up when markets get uncomfortable?

It’s not a math problem, it’s a clarity problem.

There’s a well-known behavioral finance idea that asks:

How much would you need to feel financially secure?

The answer tends to be the same. Whatever someone has… they say double.

$1M ➡️ $2M
$10M ➡️ $20M

That gap isn’t about greed. It’s commonly about not being able to see clearly what the current assets can actually do.

The issue isn’t how much you have, it’s not knowing how well you’ve already done.

Most high-net-worth individuals don’t usually need more money. They need confidence that the money they have is enough.

And that confidence doesn’t come from performance reports, new products, or more complexity.

If anything, those usually make it worse.

What actually helps is pretty straightforward:
• A clear view of what you can spend, and what that means long-term
• A plan that accounts for taxes, not just returns
• An understanding of how bad markets might affect you before they happen
• And a simple answer to the question: “Am I okay?”

This tends to show up at predictable times.

Right before retirement.
Right after a liquidity event.

There’s finally space to ask, “What does all of this actually mean for my life?”

When people see it clearly, the shift is noticeable.

They don’t suddenly become reckless. They just stop second-guessing every decision.

They spend a little more comfortably. They make bigger decisions with less hesitation. Sometimes they even decide to keep working, but now it’s a choice.

What’s interesting is this:

The people we’re meeting now generally have enough. They just don’t know it yet.

03/16/2026

The headlines are getting loud again.

War in the Middle East.
Oil prices spiking toward $100 per barrel.
Questions about whether AI spending has gone too far.
And the opposite fear - that AI could eventually replace large numbers of workers and even entire companies.

Every market cycle brings a new reason to worry.

But here’s something interesting.

Research from Morningstar estimates investors often earn 1.2% less per year than the investments they own.

Not because the investments were bad. Because emotion influences timing decisions.

Buy after markets rise.
Sell when headlines get scary.

It happens every cycle.

The difference between successful long-term investors and everyone else usually isn’t intelligence.

It’s temperament.

I shared a few thoughts on that here.

Lately the headlines have gotten louder. War in the Middle East. Oil prices spiking toward $100 per barrel. Questions about whether AI spending has gotten ahead of itself...

02/26/2026

Selling a business is hard.

Most owners spend decades building value. Then one day, a call comes in. The number is big. The timing feels right. And suddenly you’re in diligence, making decisions that will affect the after-tax outcome for the rest of your life.

This is where small details become big details.

Colby walks through some of the finer points between a stock sale and an asset sale in his latest blog post. Including how structure, tax elections, and state-specific rules can influence the outcome.

If selling your business is even a distant possibility, it’s worth understanding these issues before you’re negotiating under a deadline.

Reach out if we can help with the process.

When considering the sale of your business, buyers will almost always approach the transaction with priorities that differ from yours. Buyers generally have a preference to purchase assets, while sellers typically favor stock sales....

01/27/2026

Markets tested patience in 2025. Discipline mattered.
We’ve shared a brief recap from our 18th Annual Economic Outlook Breakfast, including:

🔵 The return of volatility
🔵 Why diversification worked
🔵 International stocks reminded us why they belong in portfolio
🔵 How headline risk affects investor behavior
🔵 Key themes for 2026 from BlackRock

We also included everyone’s favorite visual: our Asset Class Returns Quilt for 2026, plus a summary of key themes shared by Gargi Chaudhuri from BlackRock. If you missed the event, or want a clean summary, I’ve linked to the post in the comments.

12/18/2025

Big congratulations to Colby! 🎉👊

We’re excited to share that Colby recently passed all three parts of the IRS Enrolled Agent exam and is now officially recognized as an Enrolled Agent (EA) with the Internal Revenue Service.

This achievement says a lot about Colby. He is curious, dedicated, and always pushing himself to grow so he can better serve our clients. His passion for solving complex planning issues and commitment to continual learning make him an incredible asset to our team.

While we don’t prepare tax returns, having an EA on our team strengthens something far more valuable, the depth and precision of our planning. Taxes touch everything - investments, retirement income, business exits, charitable giving, college planning, estate strategies. It's your largest lifetime expense, and smart planning around it can meaningfully change outcomes.

Colby’s expertise helps us see opportunities others might miss and ensures every client’s plan reflects thoughtful, tax-aware decision-making. All while intelligently collaborating with our clients' trusted CPAs.

Please help us congratulate Colby on this well-earned milestone. We’re proud of him and our clients will benefit from his work for years to come. 👏👏👏