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This episode is a little different: instead of a tightly scripted interview, it’s designed to feel like you’re sitting in our Zoom meeting, listening to two friends bounce around big investing ideas, the stories that shape our beliefs, and the behavioral tripwires that cause most investors to make avoidable mistakes.
Ashby Daniels is back on the show. He started as a financial advisor in 2008, spent 16 years advising, and exited his practice in late 2024 to focus full time on creating content for other financial advisors to use with their clients and email lists.
Below are my notes from our conversation.
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Nick Murray’s Lasting Influence on Long-Term Investing and Market Thinking (04:15)
If you’ve heard Ashby and me talk privately, you’ve heard the name Nick Murray come up frequently.
In this episode, Ashby is direct: Nick Murray is unequivocally the most impactful person in his professional life when it comes to how he thinks about markets and investing. Ashby’s never met him, but he puts him in GOAT territory for writing about markets and helping people make sense of what’s happening.
What I’ve always appreciated about Nick Murray—and what Ashby is clearly building on—is the ability to simplify things down to first principles. Not “dumbing down,” but stripping away corrupted reasoning, dampening the noise that corrupts our thinking, and getting investors back to what is simple, actionable, and rational.
That theme—reducing complexity without losing depth—shows up again and again throughout our conversation.
Why Investing Education Should Be Short, Simple, and Actionable (05:45)
Ashby’s first book is intentionally not the traditional “big investing book.”
His hope is to write an investing book under 100 pages that captures 98% of what you need to know. The standard he keeps coming back to is simple: can someone learn what they need to know about investing in one or two hours?
His motivation is straightforward: investors (and advisors) get wrapped up in minutiae and very specific minute details—whether it’s investing or financial planning generally. The problem isn’t that details are useless. The problem is that details crowd out execution.
So the intent is to bridge the gap between knowing and doing. Ashby has tens of thousands of hours of experience in investing and markets, and his writing goal is to condense that into something someone can apply immediately.
I mentioned a book that’s been one of my most gifted books: The Elements of Investing by Burton Malkiel and Charlie Ellis. It’s short, simple, and core-principle heavy. That’s the lane Ashby wants to live in—because even if you’re not a novice, re-reading the basics can be enlightening.
Challenging Conventional Wisdom in Investing: Why Time Beats Tactics (08:00)
One thread that runs through the entire conversation is Ashby’s commitment to challenging conventional wisdom.
Conventional wisdom is what gets repeated, what gets paid attention to in the news, and what gets framed as urgent: profit margin contractions, what happened with the Fed, whatever the headline is today. That constant “here and now” emphasis makes everything feel important.
Ashby argues that the grand truth is simpler: time makes people wealthy. Not the day-to-day. Not the hot take. Not the tactical shift. Years and years.
This is where the investing mistake shows up in plain sight: investors keep interrupting compound interest with their actions and behaviors based on what they hear.
And that’s why the best advice often sounds too simple to be true—until you live through enough market cycles to see how often the simple things are the only things that keep working.
The Dave & Buster’s Investing Lesson: How to “Beat the Game” (09:45)
Ashby tells a story about the only time he’s ever been to Dave & Buster’s. He’s with a college buddy, they buy way too much access to games, and eventually they land on one of those football throwing games—the kind with holes you’re supposed to throw the ball through.
Ashby considers himself a pretty good athlete. He’s throwing like he’s trying to hit a receiver 40 yards downfield—and he’s not doing very well.
Then a guy shows up—khaki pants a little too short, Oxford button-down that looks like it lived in the glove box, glasses—and Ashby admits he judged the book by its cover.
The guy asks if they want to learn how to beat the game.
The “how” is the point: he starts shuffle passing the footballs—underhanding them through the holes. Within about 45 seconds he hits a new all-time high score and stops. Tickets start pouring out.
Then he does it again. Beats the high score again. Stops again.
Why stop? Because every time he sets a new all-time high, the machine spits out a ridiculous number of tickets. So instead of running up the score as high as possible in one round, he barely sets a new high, collects the payout, and repeats.
He then offers to teach them how to beat other games, with one condition: you pay for the games, we split the tickets 50/50.
They couldn’t have cared less about the tickets (it’s all junk anyway), but they say yes. He takes them from game to game to game, showing them how to beat each one. By the end, they have thousands and thousands of tickets. They give them to a handicapped child rolling around in a wheelchair, and it becomes a legendary night because it made the kid’s day in a way that felt real.
Ashby connects it back to investing:
Most investors try to beat the game through brute force—picking the best funds, doing the most research, picking the best stocks, timing the market. That’s the investing version of firing a football through the holes like you’re throwing deep routes.
But you don’t have to do it that way.
If you know how to beat the game, it becomes incredibly easy to beat the game. And investing works the same way.
This isn’t a promise of easy markets. It’s a promise of repeatable behavior.
It’s not about the highest score. It’s not about the highest returns. It’s about doing good enough, doing what you can repeat over and over and over again, and letting time do its thing.
Everybody Ought to Be Rich: The Power of Long-Term Stock Market Returns (15:30)
Ashby references Jeremy Siegel’s Stocks for the Long Run and the opening line that sticks with him: everybody ought to be rich.
Why? Because investors consistently underestimate how powerful the plain vanilla path can be.
Ashby uses a simple, sticky reference point: the S&P 500 opened in 1960 at 60. (Easy to remember: 1960 at 60). And at the time of this conversation, he tosses out a ballpark level around 6,800.
His point isn’t precision—it’s what that kind of growth means over decades:
- If you invested $10,000 in the S&P 500 in 1960 and held, you’d end up with over a million on price return alone.
- If you include dividends, it becomes multiple millions.
And what did you have to do? Not much. Buy it, then hold it for a very long time.
Incredibly simple. Not easy. But simple.
We also pulled in a Morgan Housel-style comparison: in heart surgery, you’d never assume an everyday person could outperform a Harvard-trained doctor. But in investing, an everyday investor can outperform the vast majority of peers simply by buying the index and holding the index.
It’s mind-bogglingly simple—and still hard for people to actually do.
The Market Portfolio Explained: Stocks, Bonds, and Investor Distractions (18:30)
At one point, I talk about how we often use the S&P 500 as shorthand for “the market,” because it’s accessible, widely quoted, and familiar. But it’s also only a slice of the opportunity set.
I mention a Goldman Sachs paper on the market portfolio and how it has evolved over time (I actually recorded an entire episode on this topic previously: EP 233: What Is The Market Portfolio—And How Should It Influence How We Invest?)
The point I’m making is about perspective:
Even though gold, private markets, and crypto get an outsized amount of airtime, they remain relatively small slices of the broader market portfolio compared to public stocks and bonds.
Ashby agrees with the spirit of this while clarifying his own language: he often says market-like portfolio. When he references market data, he quotes the S&P 500 mostly because it’s the most accessible. But the same truths hold on a total global equity market portfolio.
And that’s where we align: if you’re betting on human progress, it’s reasonable to bet on human progress across the entire globe—not only in one country.
Market Corrections and Bear Markets: Why Trees Don’t Grow to the Sky (21:15)
This is where we pivot into an idea that matters a lot to anyone writing about investing: how do you keep things timeless when markets are always changing?
I asked Ashby if there are any points in his book where he’s quietly hoping the market doesn’t do something dramatic before the book comes out. I gave my own example: I have a chapter on market history, speculative bubbles vs routine losses, and I’d really like it if AI doesn’t blow up in our face before my book comes out—not because I’m calling a bubble, but because it would be a powerful parallel.
Ashby’s answer is essentially: I want this to be timeless.
He uses the Howard Marks line that trees don’t go to the sky, and he connects it to the classic pattern—Nifty Fifty, late-90s tech, mid-2000s real estate, and potentially AI today. Whether it’s a bubble or not, the key is still the same: if you own a diversified equity market portfolio, you’re fine.
He also makes an important distinction based on where you are in life:
- If you’re an accumulator: you should hope the market falls because it gives you an opportunity to buy at lower prices.
- If you’re in retirement: you should create the conditions for patience to exist by carving out a sliver of your portfolio that isn’t market dependent and isn’t exposed to the ebbs and flows.
Same market. Different needs. Different behavior.
All-Stock Portfolios and Risk: When Equities Make Sense (24:30)
Ashby and I both share that, personally, we’re 100% stocks at this stage of our lives. And Ashby says it plainly: if you have no liquidity needs, he doesn’t know a reason to hold any other asset class.
He acknowledges what people immediately say: that’s foolish.
Then he challenges the word foolish.
His analogy: you go to a horse race and get three pieces of information—there are only two horses. One averages two miles per hour. One averages seven miles per hour. Which horse are you betting on?
Now make that bet over 50 races in a row, but you can only bet on one horse.
It becomes absurdly obvious.
Yet in investing, people bet on the slower horse all the time because they want to avoid temporary volatility.
Ashby’s argument is blunt: volatility is temporary, historically speaking. People have been betting against the future forever—and yet here we are: richer, wealthier, safer, and far beyond what people expected in the past.
He even approaches it from pure logic: why would anyone buy a company (equity ownership) if they can lend to the company (bonds) and earn better returns? Either bond returns fall, or ownership is more valuable. Either way, you end up back at equities.
He adds a line that matters for behavior: bad years for returns are great years for investing. When the future looks ugly, the impulse is to take risk off the table. But even if you knew bad years were ahead, the right preparation is being ready to buy when the time comes.
Investor Panic Isn’t About Volatility–It’s About Stories and Expectations (29:45)
I share something I’ve seen repeatedly with clients: even in a 60/40 portfolio, people still panic in big downturns. They may not lose as much, but they can still be down 35% in a crisis—and emotionally, it doesn’t feel meaningfully different.
That’s because it’s not the volatility. It’s the narrative.
People are afraid of the story the market is telling them in the moment. And the narrative is always different, always scary, always framed like the world is going to end.
Ashby reframes this as a crisis of expectations.
He offers a powerful thought experiment: if you knew the market was going to decline 30% over the next 18 months, you’d probably be immensely more patient. What makes declines hard is the anxiety of uncertainty—you don’t know how far, and you don’t know how long.
But historically, you can set expectation ranges:
- A 5% decline happens multiple times a year.
- A 20% decline happens every handful of years.
- A 30% or greater decline happens every decade.
We should expect these things to come. We just can’t know when.
And timing isn’t just about getting out—it’s about getting back in. When it’s time to buy, you won’t want to. Nobody wanted to buy in late 2008 or early 2009, and that’s exactly when people should have been buying.
This is the behavioral edge: setting expectations so normal market declines don’t feel like personal failure.
Bond Investing, “Safety,” and the Hidden Risk to Purchasing Power (32:45)
We also touch on a common misunderstanding that shows up in real portfolios: some investors reduce stock exposure because they want to take less risk.
Ashby’s point is that you’re not taking less risk—you’re taking a different risk.
If someone moves toward heavy bonds because it feels safer, they’re introducing purchasing power risk: giving up something like a 7% real return path for something closer to a 2% real return path (and even that isn’t guaranteed across decades).
And that’s the bigger theme: Everyone is taking risk. There is no such thing as no risk. It’s just when you want it, and what form you want it to take.
Private Equity, Gold, and Crypto: What Investors Get Wrong (35:45)
When we pivot into private markets, crypto, and gold, Ashby’s framing is simple and sharp.
Private equity as the buffet line organized by net worth:
Imagine a buffet where the line is organized by net worth. Everyday investors are at the back. You get what’s left after big money has taken the best opportunities.
So when private equity shows up in mainstream ETFs or inside your 401(k), Ashby’s skepticism is straightforward: it’s not going to look like the same opportunity set as Sequoia Capital. The logic doesn’t pass.
Gold and crypto as non-income producing assets:
Ashby groups gold and crypto together as non-productive assets that don’t produce anything.
His filter is blunt: he doesn’t believe in investing money into something that is purely speculative, and he doesn’t believe you can fundamentally evaluate Bitcoin or gold. Not because returns can’t be great—returns might be great—but because they aren’t evaluable in the same way productive assets are.
In his view, for the price to rise, broader adoption has to continue. More people have to buy. If ownership never changed again, the price would stay where it is.
Equities are different. If a business has rising revenues and profits, the value can rise even if not a single share changes hands.
That’s the key distinction: productive assets don’t rely on broader adoption alone.
I add my own stance here too: I’m firmly out on gold and crypto, full stop. When clients still want exposure, I’ll facilitate within frameworks and goalposts, because it’s their money—but I treat it as story-driven, like expensive art, collectors cards, or individual stocks.
And I’m out on individual stocks as well because, in practice, even with a productive asset, many people are buying a story.
I also mention my private markets nuance: I’m not against private investments in principle, but I don’t view them as an asset allocation exercise for most people. Expectations and manager selection matter massively—especially the difference between top-quartile outcomes and everything else. A lot of sales pitches are full of facts… they’re just not relevant.
The $100 Million Thought Experiment: Getting Wealthy vs Staying Wealthy (41:30)
We close the circle with a question that reveals a lot about how someone actually thinks:
If you woke up tomorrow and $100 million landed in your bank account, would you make private investments?
I said I might—mostly as an expensive hobby, something interesting to do, potentially in areas where I have expertise or where I can be hands-on. Not because of portfolio theory.
Ashby’s answer is the clean counterpoint:
Once you have generational wealth, the only thing you have to do to keep it is follow fundamental, plain vanilla, very boring investment principles. A boring index portfolio gives you the best probability of staying wealthy.
He frames it using the Fortune 400 turnover idea: you don’t get there with plain vanilla indexing, but you stay there with plain vanilla indexing.
We agree on the punchline: Getting wealthy and staying wealthy are different skill sets.
Closing Thoughts: The Most Timeless Investing Advantage Is Behavioral
This episode doesn’t land on a single “one weird trick” strategy. It lands where the best investing advice usually lands:
- Learn how to beat the game instead of relying on brute force
- Don’t interrupt compound interest
- Expect declines—and stop treating normal market behavior like an emergency
- Build portfolios (and liquidity buffers) that allow patience to exist
- Remember that a lot of shiny-object narratives are loud, and the boring stuff keeps working
Resources:
- The Elements of Investing by Burton Malkiel and Charlie Ellis
- Stocks for the Long Run by Jeremy Siegel
- EP 233: What Is The Market Portfolio—And How Should It Influence How We Invest?
The Long Term Investor audio is edited by the team at The Podcast Consultant
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