Afford Anything

Tag: investing

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#619: Q&A: My Company Is Going Public and I Have No Idea What to Do – Plus, Should I Fire My Advisor?

Dave is no longer happy with his financial advisor, but he’s nervous about switching over to self-management after being completely hands-off for so long. What should he do?

An anonymous caller keeps hearing about the benefits of Cost Segregation for investment property. What is it? And should he apply this strategy to his recently acquired duplex?

Another anonymous caller is eagerly anticipating a windfall from his employer’s upcoming IPO. How should he prepare for this, and what happens if it fails?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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#608: The Stoic Path to Wealth, with Billionaire Investor and Philanthropist Robert Rosenkrantz

At age seven, Robert Rosenkrantz made a decision that would shape his entire life: he would take full responsibility for his future.

As a child, Rosenkrantz watched his parents struggle financially. His father was unemployed for two years, and his mother worked as a drugstore clerk.

Their financial insecurity was painfully obvious to young Robert. He never knew if the electricity or telephone service would be shut off.

But rather than seeing this as an obstacle, he saw it as a path to self-reliance.

By age 14, Rosenkrantz was managing investments for his family. By 35, he had amassed $400,000 — equivalent to about $4 million today. Then came the pivotal moment that changed everything: a negotiation with wealthy entrepreneur Joe Mailman.

When Mailman expressed concerns about traditional investment structures that created a “heads you win, tails I lose” scenario, Rosenkrantz made a bold counter-offer. He put his entire liquid net worth at risk in exchange for a 50/50 profit split with no carried interest.

“First deal, we lost $100,000. The second one, we made $100 million,” Rosenkrantz says during the interview. “So it averaged out.”

Now 82, Rosenkrantz joins us to discuss his book, “The Stoic Capitalist,” and the principles that guided his career.

For over 35 years, he’s carried the same negotiation card from “Getting to Yes” in his wallet — a reminder that negotiation isn’t about winning, but solving problems together.

We talk about his counterintuitive investment philosophy: look for companies that require minimal specialized talent, like laundromats or self-storage facilities. He says these often make better investments than those needing exceptional management, like restaurants.

This principle guided his first major success, a lawn and garden products business that essentially put dirt in bags — a simple operation that became a regional monopoly and eventually sold for $100 million.

Today, Rosenkrantz funds scientific research on longevity and hosts debate programs that present balanced perspectives on contentious issues. His philanthropy includes backing a groundbreaking study that has extended worm lifespans from 15 days to over 250 days — potentially the longest lifespan extension ever achieved in any organism.

When asked about retirement, he responds: “How do you spell that?”

His advice for decision-making comes straight from stoic philosophy: focus only on what you can control — the present and future, not the past. This means disregarding sunk costs completely when making decisions and using reason to regulate emotions.

For Rosenkrantz, counting the zeros — focusing only on opportunities with enough potential impact — helps prioritize time and delegate effectively. At 82, he still practices these principles daily, considering himself “biologically more like 70 and getting younger.”

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#583: Q&A: Everyone Is Arguing About Roth IRAs And We Have Thoughts

Contrary to recent discussions, Jesse has concluded that a traditional IRA is the smarter way to go for most people once marginal tax rates are factored in. Is he missing something?  

An anonymous caller is four years away from early retirement but she’s unsure if her portfolio allocations are in the right place. How and when should she start converting equities to cash?

Luz is confused about how to handle company stock options. Is there an ideal spread between the exercise price and the stock price? And, what should she do once the stocks are exercised?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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#575: Q&A: The Roth Decision at Every Income Level (And Why It Matters Now!)

Krish is fascinated by cryptocurrency and its impact on global investing. What opportunities should he capitalize on, and how?

Apar’s income has more than doubled after he started his own business. His advisor recommends Roth contributions but he’s skeptical due to his high income. Who’s right?

Keith is frustrated by the conflicting advice he’s heard about Roth conversions. Is it better to do it while he’s young and earning a lower income, or should he wait until closer to retirement?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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#571: Q&A: When Your Crypto Bet Pays Off TOO Well

An anonymous caller’s crypto investments have recently skyrocketed to 17 percent of her investment portfolio. Given the volatility of this asset, should she rebalance it or go all in?

Jocelyn wants to buy a house in three years but she’s reluctant to keep her sizable down payment in cash. What if she splits the difference and invests half the money instead?

Allison feels antsy holding $1 million in cash with falling interest rates on the horizon. How does she optimize this money while keeping it liquid enough to buy a house on an uncertain timeline?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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#560: The Father of the 4% Rule Finally Sets the Record Straight

Bill Bengen, the former rocket scientist who discovered the “4 percent rule” of retirement planning, joins us at the Bogleheads conference in Minnesota.

Bengen clarifies that calling it a “rule” is misleading since it doesn’t fit everyone’s situation. The 4 percent figure came from studying the worst-case scenario since 1926, when someone who retired in 1968 could only safely withdraw 4.2 percent annually. Out of 400+ retirees in his database, that was the only one who had such a low safe withdrawal rate — most could take out much more.

Recent research has pushed the “safe” withdrawal rate closer to 5 percent. But Bengen identifies eight key factors that affect how much you can withdraw, including how long you’ll be retired and whether you’re drawing from taxable or tax-deferred accounts.

For early retirees planning for 50-60 years, Bengen says the safe withdrawal rate asymptotically approaches 4.2 percent — meaning even with an infinite time horizon, it won’t drop below that. He thinks the common advice to use 3 percent for early retirement is unnecessarily conservative.

Bengen shares what he calls the “four free lunches” in retirement planning:
1. Using an equity glide path (reducing stocks at retirement, then increasing later)
2. Diversification across asset classes
3. Regular portfolio rebalancing
4. Slightly overweighting higher-returning assets like small-cap stocks

When it comes to market drops versus inflation, Bengen has clear advice: Don’t panic during bear markets — they typically recover. But if you hit extended high inflation early in retirement, it’s time to “head for the bunkers” and cut expenses drastically.

Beyond finance, Bengen shares his excitement about space exploration as a former rocket scientist who graduated from MIT just months before the moon landing. He hopes to live long enough to see humans reach Mars and believes space tourism helps people appreciate Earth’s beauty and fragility.

The interview ends with a light-hearted discussion about whether Pluto should still be considered a planet (Bengen still calls it one, out of habit) and speculation about future tourism to Saturn’s moon Titan once the sun’s expansion makes it warmer in a few hundred million years.

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#559: Q&A: Should We Ditch Rental Properties Entirely?

An anonymous caller, whom we name “Samantha,” and her husband are financially strained and feeling torn. Shortly after purchasing two rental properties, their income dropped dramatically. Should they sell?

Tina is a full-time environmentalist. She’s worried that her index funds don’t align with her values on sustainability. Is there a world where she can be a savvy investor and fight climate change?

Another anonymous caller, whom we name “Sarah,” is excited and uncertain about her growing business. Should she hold steady or invest more resources into it? And how does she know if she’s making the right call?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

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#553: The Brutal Money Truth No One Wants to Hear, with Dr. Brad Klontz and Adrian Brambila

This is the third and final episode in a three-part series. Dr. Brad Klontz and Adrian Brambila join us to share 21 harsh truths about building wealth.

This episode focuses on the final 11 harsh truths, following up on their previous conversations about the first 10 harsh truths.

The conversation begins with a key distinction: poor people buy stuff, while rich people buy time. They explain how wealthy people focus on building passive income streams rather than trading hours for objects. Brambila shares how he learned this lesson personally, discussing his pickleball court purchase through investment income rather than active work hours.

The duo challenges common assumptions about luxury brands, arguing that people who constantly show off designer items are usually compensating for insecurity. Klontz shares his own experience of buying an expensive watch early in his career to prove his success.

They examine whether college, marriage, and homeownership are necessary for wealth building. While data shows these traditional paths often lead to higher net worth, they acknowledge these aren’t the only routes to financial success.

On the topic of retirement, both guests argue that completely stopping work can be psychologically harmful, sharing examples of successful people who stayed active well into their later years.

They break down specific money-saving strategies like getting roommates, using public transportation, and cutting your own hair. Brambila demonstrates how women can cut their own hair during the interview.

The discussion covers specific side hustle opportunities, with detailed explanation of how to make money doing Amazon product reviews. Brambila shares how his videos have generated significant income, including $2,000 in a single day during Black Friday.

They address money myths about credit cards, particularly the misconception about carrying balances to improve credit scores.

Real examples and personal stories illustrate their points. Klontz shares how his 11-year-old son is making $5,000 monthly doing Amazon reviews, while Brambila discusses living in a van while earning six figures to demonstrate that wealth isn’t about outward appearances.

The episode concludes by connecting financial security to Maslow’s hierarchy of needs, explaining how building wealth enables higher-level personal growth and positive impact

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#550: Paul Merriman: The 4-Fund Strategy That Beats the S&P 500

Paul Merriman, a former wealth manager turned financial educator, joins us to share investing wisdom that could reshape how you think about your money.

We kick things off talking about portfolio diversification. Paul suggests a simple four-fund strategy that includes large cap, small cap, and value stocks. He says this mix has historically beaten the S&P 500 with lower risk.

We then dive into international investing. Paul explains that while adding international stocks doesn’t necessarily boost returns, it can help smooth out the ride. He keeps half his equity portfolio in international stocks, even at age 81.

Got kids? Paul’s got some advice for you too. He tells us about putting money aside for his new granddaughter, aiming to fund her Roth IRA as soon as she can earn income. He breaks down how investing just a dollar a day from birth to age 21 could turn into millions by retirement age. It’s a powerful lesson in starting early and the magic of compound interest.

We also chat about some common investing mistakes. Paul stresses that young investors often underestimate the power of stocks over bonds for long-term growth. He shares some eye-opening numbers: $100 invested in bonds since 1928 would have grown to about $12,000, while the same amount in small cap value stocks would be worth nearly $15 million.

Paul wants you to think of investing as a partnership with businesses. When you buy a mutual fund, you’re becoming a senior partner in thousands of companies. At first, your contributions drive most of the growth. But over time, market returns take over, and you become the junior partner to a much larger fortune.

We wrap up with Paul sharing his excitement about a 40-hour financial education program he helped create at Western Washington University. It’s designed to teach students essential money skills throughout their college years, from budgeting as freshmen to understanding 401(k)s as seniors.

Throughout our chat, Paul’s message is clear: start early, stay diversified, and think long-term. He believes that with the right education and mindset, anyone can build a solid financial future.

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