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Questions from the Talking Billions CommunityThe second installment of my monthly listener Q&A — raw, unscripted, and as close to a one-on-one conversation as you'll get without picking up the phone. I sit down with your real questions about investing, portfolios, patience, and why so few people actually talk to someone about their money.

Episode highlights:

Why you'll never hear specific stock picks on this show — and why that's actually the point. A single holding pulled out of context is like a prescription without a diagnosis. I explain why frameworks matter more than tickers and how every portfolio is a one-of-one.

A candid look at the biggest psychological traps in investing: impatience, borrowed conviction, and saying "long-term" when your behavior says otherwise. I draw on childhood memories of mushroom foraging with my grandfather and the rhythms of farming to make the case that patience isn't a personality trait — it's a skill built through repetition and loss.

How 200+ episodes of podcasting quietly transformed my investment practice — the systems thinking, the database mindset, the discipline of showing up week after week. The show didn't just document my process, it sharpened it.

The no-middleman philosophy: what it means to own every holding alongside my clients, to write personalized letters each quarter, and to build a practice where the advisor and the investor are on the exact same journey.

And the question beneath all the questions: What got you here — will it get you where you're going? A warm, honest invitation to anyone carrying real wealth and wondering whether a second pair of eyes might be worth the conversation.

Listen if: You've been managing your own money successfully and have started wondering what you might be missing. Or if you just want to spend 45 minutes with someone who genuinely loves his craft, and enjoys sharing what he has learned so far.Podcast Program – Disclosure Statement

Blue Infinitas Capital, LLC is a registered investment adviser and the opinions expressed by the Firm’s employees and podcast guests on this show are their own and do not reflect the opinions of Blue Infinitas Capital, LLC. All statements and opinions expressed are based upon information considered reliable although it should not be relied upon as such. Any statements or opinions are subject to change without notice.

Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and unless otherwise stated, are not guaranteed.

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Richard Oldfield, founder of Oldfield Partners and author of the investing classic Simple, but Not Easy, is a four-decade veteran of markets whose career arc from Warburg and Mercury Asset Management to running a family office gives him a rare dual vantage point as both portfolio manager and allocator of managers.

The episode is sponsored by TenzingMEMO — the AI-powered market intelligence platform I use daily for smarter company analysis. Code BILLIONS gets you an extended trial + 10% off.

https://www.tenzingmemo.com/

3:00 — Richard shares his origin story: drew to markets at 15, first investment at 18 in Britannia Arrow at 6p. Core belief: “Value investors are born, not made.”

5:00 — Warburg founding story: Sigmund Warburg fled Germany in 1934 and built an institution with a lasting ethos. Richard recalls a personal hour-long meeting with him.

6:30 — The 1987 storm and Black Monday. Walking among fallen trees as the Dow dropped 500 points (25%), Richard saw it as a price movement, not reality — until he returned to the office and was “swallowed up in the gloom.” Lesson: avoid the cacophony.

9:00 — Isaac Newton and the South Sea Bubble: “I can understand the movement of the planets, but not the madness of men.” Don’t make wholesale asset allocation bets.

13:00 — Family office decade: empowerment, privacy, and bravery. The patriarch’s stamp: “Return to sender — you decide.” The freedom to be unconventional.

19:30 — The book’s central paradox: rudiments of equity investing are simple. Professionals obscure them with jargon and self-interest. But half will underperform by definition — fees and all.

22:40 — Patience comes from Latin with three meanings: waiting, suffering, and passion. You need all three.

28:30 — Track records mislead. Never judge a manager primarily by performance. The transaction record reveals conviction and patience. “My favorite holding period for a manager is forever.”

38:30 — The 90% decline must be thought about. Establish your cushion of comfort upfront. Diversify globally.

50:00 — Rip Van Winkle Asset Management: dead investors outperform living ones. Hyperactivity is the enemy; the average fund investor earns 3-4% vs. the fund’s 8%.

56:30 — Take your own medicine. 95% of Richard’s assets are in his own funds. A manager who won’t invest alongside clients is a red flag.

1:04:30 — Success redefined: resume virtues vs. funeral virtues. “You want to have the feeling that they loved and were loved.”

Podcast Program – Disclosure Statement

Blue Infinitas Capital, LLC is a registered investment adviser and the opinions expressed by the Firm’s employees and podcast guests on this show are their own and do not reflect the opinions of Blue Infinitas Capital, LLC. All statements and opinions expressed are based upon information considered reliable although it should not be relied upon as such. Any statements or opinions are subject to change without notice.

Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and unless otherwise stated, are not guaranteed.

Spend an hour this weekend with one of the kindest and most generous people — an accomplished investor and a truly remarkable mind (Original Release: Jan 30, 2023).

Guy Spier is a good friend, an inspiration, and one of Talking Billions' earliest guests. He is the Zurich-based founder of the Aquamarine Fund, author of The Education of a Value Investor, and host of VALUEx — a wonderful gathering of like-minded investors. He is also the man who famously paid $650,000 alongside Mohnish Pabrai to have a charity lunch with Warren Buffett.

5 Biggest Ideas from the Episode

1. It's not the fastest skier who wins — it's the fastest who doesn't get injured. Drawing from Luca Dellanna's work on ergodicity, Guy makes a powerful case for survival over speed. If you're eliminated early, you miss all the remaining races. As he put it: "If you want to be really smart about it, you're going to race in a way that will ensure that you get down without injury."

2. Losing it all is the ultimate failure — and it's always avoidable. If you're in the business of preserving wealth, losing the capital base means being forced back to selling your time. Sophisticated people repeatedly make this mistake — from LTCM to FTX — and it never had to happen.

3. Your social environment shapes your investing more than your physical one. Who you spend time with changes how you think and behave — and investing is no exception. Attending Berkshire meetings for 25 years wasn't just education; it was deliberately engineering a network that reinforces long-term compounding thinking.

4. Investing is like planting vineyards — not all vintages will be fantastic, but you'll always have wine to drink. Guy's philosophy for navigating inevitable down years: plant the best vines you can, then let the seasons do what seasons do. His response to complaining investors: "What am I supposed to do? Jump up and down and yell at the sun?"

5. Success is not a number — it's who shows up at your funeral. Guy stopped tracking his net worth spreadsheet years ago and never looked back. His definition of success: dying with many people who are genuinely glad he existed — not optimizing himself into a narrower version of Warren Buffett.

Podcast Program – Disclosure Statement

Blue Infinitas Capital, LLC is a registered investment adviser and the opinions expressed by the Firm’s employees and podcast guests on this show are their own and do not reflect the opinions of Blue Infinitas Capital, LLC. All statements and opinions expressed are based upon information considered reliable although it should not be relied upon as such. Any statements or opinions are subject to change without notice.

Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and unless otherwise stated, are not guaranteed.

Spencer Jakab is an award-winning Wall Street Journal investing columnist with 30 years of finance experience who transformed from emerging markets research director into a financial journalist exposing how everyday investors repeatedly get fleeced by Wall Street's latest schemes.

Episode Sponsor: Fiscal AI is a modern data terminal that gives investors instant access to twenty years of financials, earnings transcripts, and extensive segment and KPI data—use my link for a two-week free trial plus 15% off: https://fiscal.ai/talkingbillions/03:00 - Spencer's origin story: Growing up in Queens as son of Hungarian refugees, discovering investing through Peter Lynch's "One Up On Wall Street" in college, despite his late father's unsuccessful attempts to spark his interest earlier.

08:00 - The accidental career path: Taking every finance class at Columbia, landing in emerging markets analysis covering post-Iron Curtain privatizations, then pivoting to Wall Street Journal journalism after a chance plane conversation led to same-day writing test and job offer.

15:00 - GameStop reality check: The meme stock phenomenon wasn't the democratizing revolution portrayed on social media—it was another example of retail investors getting manipulated while believing they were "sticking it to the man."

25:00 - The casino-fication of investing: How Robinhood and app-based platforms gamified trading with confetti animations and frictionless execution, making speculation feel like a mobile game rather than serious wealth-building.

35:00 - Why passive beats active: Spencer explains the brutal math—only 11% of active fund managers beat the market over 30 years, and individual investors perform even worse due to fees, taxes, and behavioral mistakes.

45:00 - The finfluencer trap: Social media rewards reckless investing behavior because outrageous bets generate more engagement than boring, sensible advice—creating dangerous incentive structures that harm followers.

60:00 - Bots and manipulation: Modern markets face new threats from AI-generated social media campaigns pumping meme coins and stocks, making it nearly impossible to distinguish genuine sentiment from coordinated manipulation.

67:00 - Defining success: Spencer's powerful reflection on career choices—turning down potential hundreds of millions to do work he loves, echoing Warren Buffett's definition of success as having people genuinely care about you when you're gone.

Podcast Program – Disclosure Statement

Blue Infinitas Capital, LLC is a registered investment adviser and the opinions expressed by the Firm’s employees and podcast guests on this show are their own and do not reflect the opinions of Blue Infinitas Capital, LLC. All statements and opinions expressed are based upon information considered reliable although it should not be relied upon as such. Any statements or opinions are subject to change without notice.

Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and unless otherwise stated, are not guaranteed.

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Tobias Carlisle is founder and portfolio manager of Acquirer’s Funds managing two deep value ETFs, acclaimed author of five investment books including his newest Soldier of Fortune blending Warren Buffett and Sun Tzu’s strategic wisdom, and host of the popular Value After Hours podcast.

Episode Sponsor: Fiscal AI is a modern data terminal that gives investors instant access to twenty years of financials, earnings transcripts, and extensive segment and KPI data—use my link for a two-week free trial plus 15% off: https://fiscal.ai/talkingbillions/

3:00 - Tobias shares his unique upbringing in Australian outback where school ended in grade 10 and included animal husbandry—learning to shear sheep and work cattle in what he calls a formative contrast to his later academic life at boarding school.

6:00 - Transition to law career: Started at a national law firm in April 2000, peak of dot-com bubble. “I missed out on all of the fun parties on the way up and I just saw the carnage on the way down,” which opened his eyes to the importance of cash flow over hype.

9:00 - Early exposure to activist investing: Witnessed corporate raiders targeting dot-coms with cash on balance sheets, killing the business and liquidating or using as platform for acquisitions. This low-downside, high-complexity approach fascinated him.

14:00 - The telecom case study: Worked with two entrepreneurs who turned $100,000 each into a $600 million exit by building dark fiber infrastructure and data centers. “They were the best telecom lawyers in Australia and they weren’t lawyers”—emphasizing the power of combining financial, technological, and regulatory understanding.

28:00 - Philosophy behind Soldier of Fortune: Explores Warren Buffett as risk-taker rather than risk-avoider, connecting his strategic thinking to Sun Tzu’s Art of War. The book examines 13 laws of strategic advantage.

45:00 - Discussion of key laws: “Attack weakness with strength” and “seize the initiative”—Buffett’s approach to investing in moments when he has maximum advantage, like deploying capital during the 2008 crisis.

1:08:00 - The surfing analogy: Experienced investors are “not only on the right wave, but at the right spot on that wave”—getting positioning and timing right rather than just working harder.

1:09:00 - Impact on his own investing: “Shot selection becomes so much better the longer that you do something...if I’m just a little bit more patient, I know that there is a bigger wave coming.”

1:11:30 - Definition of success: “A happy, healthy family and time with my kids...watching them play sport. That’s really my definition of success.”

Podcast Program – Disclosure Statement

Blue Infinitas Capital, LLC is a registered investment adviser and the opinions expressed by the Firm’s employees and podcast guests on this show are their own and do not reflect the opinions of Blue Infinitas Capital, LLC. All statements and opinions expressed are based upon information considered reliable although it should not be relied upon as such. Any statements or opinions are subject to change without notice.

Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and unless otherwise stated, are not guaranteed.

Drew Cohen is the founder of Speedwell Research and a portfolio manager at Davidson Kahn Capital Management, who uncovers competitive advantages by reading entire company histories spanning decades of transcripts and annual reports.

The episode is sponsored by TenzingMEMO — the AI-powered market intelligence platform I use daily for smarter company analysis. Code BILLIONS gets you an extended trial + 10% off.

https://www.tenzingmemo.com/

3:00 - Drew describes his early money attraction, collecting dollar bills at age five and discovering the power of interest at his bar mitzvah, leading his father to introduce him to stocks.

5:00 - First investing experiences: buying leveraged ETFs at 14, making $100 in two minutes, then immediately losing $100, learning markets can create and destroy wealth quickly.

8:00 - Exploration of technical analysis through Dow Theory and Elliott Wave, realizing these pattern-based approaches kept adding rules to fit outcomes, concluding they were “BS” and abandoning them.

10:00 - Discovering “The Snowball” at 17 changed everything, learning Buffett’s lessons without having to lose more money personally through trial and error.

15:00 - Deep research methodology explained: reading every transcript and annual report since IPO to find patterns that map onto future transitions and understand how companies behave under different conditions.

20:00 - Meta example: three instances of monetization fears (desktop to mobile, feed to stories, stories to Reels) that all proved unfounded when studying company history.

23:00 - Copart case study: finding one 2004 earnings call where they mentioned market share, crucial data point never discussed again but essential for understanding current competitive position.

35:00 - Discussion of reading as filtering mechanism: eliminates 95% of companies immediately, leaving only truly interesting businesses worth deeper analysis.

45:00 - Career trajectory: Goldman Sachs sell-side to Capital Group buy-side, learning institutional constraints firsthand before founding independent research firm.

55:00 - Sell-side research revelation: buy ratings are relative to coverage universe, not absolute recommendations, creating fundamental misunderstanding of analyst intentions.

57:00 - Buy-side problems: short-term performance pressures, peer judgment, window dressing (adding Nvidia when it’s hot to satisfy clients), non-investment prerogatives polluting decisions.

59:00 - Buffett’s genius: structuring Berkshire with long-term capital he controlled, avoiding quarterly performance pressures that would have produced completely different results.

1:00:23 - Success definition: doing what you want each day without trading tomorrow for today, echoing Naval’s concept that you’re retired when you stop deferring gratification.

Podcast Program – Disclosure Statement

Blue Infinitas Capital, LLC is a registered investment adviser and the opinions expressed by the Firm’s employees and podcast guests on this show are their own and do not reflect the opinions of Blue Infinitas Capital, LLC. All statements and opinions expressed are based upon information considered reliable although it should not be relied upon as such. Any statements or opinions are subject to change without notice.

Information presented is for educational purposes only and does not intend to make an offer or solicitation for the sale or purchase of any specific securities, investments, or investment strategies. Investments involve risk and unless otherwise stated, are not guaranteed.