Retirement Optimism Podcast

Alternative investments like private equity, crypto, and gold are capturing attention again — especially as access widens and prices rise. But broader availability doesn’t automatically translate into better opportunities for the everyday investor.

Private equity access sounds exciting, yet institutional money will almost certainly get premium deals while Main Street investors are left picking through what’s left. Crypto has surged, but its value depends solely on continued adoption — a textbook example of the greater fool theory — unlike equities, which grow as earnings grow. And gold, despite its reputation, historically delivered returns barely above inflation and remains a non-productive asset.

Drawing on Warren Buffett’s famous comparison between productive and non-productive assets, the conclusion is straightforward: over time, assets that produce cash flow and compound earnings will outpace those that rely on sentiment and speculation.

In a world full of flashy investment headlines and new access points, the long-term play remains unchanged — stay focused on productive, compounding assets and avoid distractions that look exciting now but may disappoint later.

Are we in an AI bubble? Everywhere you look, billions are being poured into artificial intelligence, and the comparisons to the dot-com era are hard to ignore. In this episode, David Hicks breaks down what “bubble talk” really means — why not all bubbles are bad, why timing them almost never works, and how smart diversification keeps long-term investors grounded no matter what’s trending in the headlines.

It’s a timely reminder that real progress often comes from periods of exuberance — and that steady, disciplined investing still wins in the end.

Stay the course. Stay optimistic. Love your retirement.

In this episode of Retirement Optimism, David Hicks explores one of Morgan Housel’s “little rules about big things”: focus on risks that cause permanent damage, not temporary harm. Drawing on client stories and the Oakmont Retirement Design process, David shows how most threats to retirement success don’t come from headlines or market swings—they come from our own reactions. From panic selling to overconcentration in a single stock, he breaks down the behaviors that can derail a retirement plan and shares how thoughtful design helps protect against lasting mistakes. Listen in for a reminder that optimism, discipline, and a clear plan are the best tools for loving your retirement.

In this episode of Retirement Optimism, David Hicks explores how generosity and smart planning can go hand in hand. Writing a check is the simplest way to give—but often not the most efficient. David walks through three strategies that can help you maximize both your charitable impact and your tax benefits:

Donating appreciated investments instead of cash to avoid capital gains taxes and give more.

“Bunching” multiple years of gifts into one for a larger tax deduction while still supporting charities over time.

Giving directly from your IRA through Qualified Charitable Distributions (QCDs), which can also lower taxable income and Medicare premiums.

You’ll also hear real-world examples of how these strategies play out and why this fall—heading into year-end and with September planning meetings just around the corner—is the perfect time to talk through them.

Stay the course. Stay optimistic. And make your generosity go further.

In this episode of Retirement Optimism, David Hicks unpacks the current state of the real estate market—nationally and here in New Mexico—and how it fits into your retirement planning strategy. With interest rates still elevated, home prices holding steady, and buyers and sellers stuck in a stalemate, the market feels uncertain. But uncertainty doesn’t mean paralysis.

David breaks down what’s driving the imbalance, how to think about mortgage payments vs. home prices, and what types of properties are still moving. You’ll also hear how the landscape in places like Corrales and Rio Rancho reflects broader national trends—and how retirees and pre-retirees should be thinking about real estate as part of their long-term design.

Whether you’re considering downsizing, tapping into equity, or just keeping tabs on the housing market, this episode offers clarity, perspective, and practical insights.

How can the market be hitting all-time highs while uncertainty feels higher than ever?

In this episode, David unpacks one of the biggest misconceptions in investing today: that uncertainty equals risk. Drawing on lessons from history, recent headlines, and voices like Howard Marks and Nassim Taleb, he explains why the real danger isn’t what happens—but how we react to it.

You’ll learn why long-term success requires resilience, not prediction—and how Oakmont’s Retirement Design process is built to help you thrive through whatever the market throws your way.

If you’re not yet a client and want clarity in uncertain times, visit oakmontadvisory.com to start your own Retirement Design plan today.

In this episode of Retirement Optimism, David Hicks breaks down the newly signed legislation unofficially dubbed “The Big Beautiful Bill.” With major updates to tax brackets, deductions, estate planning exemptions, and more, this law has big implications for income planning, Roth conversions, Social Security taxation, and long-term legacy strategies.

David walks through the key provisions that matter most for retirement-focused households—what’s changing, what’s staying, and how to take advantage of the new rules with smart planning. From the permanent extension of lower tax brackets to the expanded SALT deduction and estate tax relief, this is a practical, optimistic look at how new policy can support long-term financial confidence.

Tune in to learn what this bill means for your Retirement Design, and how Oakmont is already weaving these changes into every client plan.

This week, David shares reflections from the final days leading up to the 29029 TRAIL event in Park City—a three-day endurance challenge covering 26.2 miles each day and nearly 17,000 feet of elevation gain.

With his training behind him and the taper period in full effect, David unpacks why preparation—not perfection—is what truly determines success, both on the trail and in retirement.

He draws powerful parallels between endurance training and financial planning, and discusses how most retirement journeys are built on long timelines, small consistent steps, and flexible strategies—not flawless execution.

Backed by real data and timeless reminders, this episode encourages listeners to shift their focus from doing things exactly right to simply getting started and staying consistent.

This week’s episode is a little different—but no less important. Instead of focusing on markets or strategy, David invites listeners to step back and ask some deeper, more personal questions.

Have you ever reached a milestone and thought, “Now what?” Whether you’re newly retired, mid-career, or just starting out, there comes a time when we all wonder if the life we’ve built truly reflects what matters most to us.

David explores the power of intentional reflection, why clarity doesn’t come from constant motion, and how to begin shaping your next chapter—whatever that may look like. He also shares a few simple but powerful questions to help guide that process.

Because retirement isn’t just about assets and income.

It’s about creating a life that feels meaningful.

Key Themes:

– Feeling stuck, even when things are “going well”

– The importance of reflection and clarity

– How to imagine and plan your next life chapter with intention

– Why financial planning should support who you want to become

As always—stay the course.

In this episode of Retirement Optimism, David Hicks addresses a question many investors have been asking: “Is diversification still worth it?” After years of U.S. stock market dominance, it’s easy to feel like international stocks and other underperforming asset classes don’t belong in your portfolio. But that thinking misses the point.

David breaks down why diversification is still a critical part of long-term success—especially as international markets begin to outpace U.S. performance in 2025. Drawing on recent data from Visual Capitalist, CNBC, Schwab, and Dividend.com, this episode highlights the behavioral and strategic value of holding a globally diversified portfolio. You’ll learn why diversification isn’t about predicting the next winner—it’s about preparing for whatever comes next.

He also explains how Oakmont’s Retirement Design process helps investors build portfolios that can weather market cycles and stay aligned with their goals.

Takeaways:

Diversification isn’t broken—it’s working exactly as intended.

U.S. outperformance was diversification for investors abroad.

International markets are showing signs of leadership again.

Good behavior, not predictions, is the foundation of long-term results.

We diversify not because we know what will happen, but because we don’t.

Links Mentioned:

🔗 Retirement Design Process: oakmontadvisory.com/process

📊 Sources: Visual Capitalist, CNBC, Schwab, Dividend.com