🎧 What separates a great investor from everyone else? In this episode of the Limitless Podcast, Dr. Matthew Preston and Dr. Thaon Simms explore the psychology behind winning and losing in the stock market through lessons from The Art of Execution by Lee Freeman-Shor. 📚📈

From holding onto losing stocks for too long 😰 to selling winners too early 💸, Matthew and Thaon break down five investor archetypes: the Rabbit, Assassin, Hunter, Raider, and Connoisseur. They explore how each reacts when money is on the line.

They also get personal about what losing money actually feels like, why unrealized losses still matter, averaging down, cutting losses, investment theses, opportunity cost, and the emotional discipline required to make difficult decisions. 🧠💰

Whether you're a beginner or an experienced investor, this conversation will challenge you to ask one important question: What type of investor are you? 🤔

📊 Highlights & Chapters:

0:00 - 3:48 | 📚 The Art of Execution & What Makes a Great Investor
3:48 - 14:06 | 🧠 Losing Money, Investor Psychology & Emotional Discipline
14:06 - 22:58 | 💸 Unrealized Losses, Opportunity Cost & Knowing When to Act
22:58 - 26:17 | 🐇 Rabbit vs. Assassin vs. Hunter Investors
26:17 - 34:07 | 🎯 Risk, Financial Advice & Making Tough Investment Decisions
34:07 - 39:46 | 📉 Real Investing Losses & Questions to Ask When You're Down
39:46 - 43:12 | 💰 The Raider vs. the Connoisseur: Selling Winners Too Early
43:12 - 47:35 | 🏆 Patience, Holding Winners & Becoming a Better Investor

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❓ Which investor are you most like: the Rabbit, Assassin, Hunter, Raider, or Connoisseur? Let us know in the comments!

⚠️ Disclaimer: The opinions expressed in this podcast are solely those of the hosts and do not constitute financial advice. Please consult a financial advisor before making any investment decisions.

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We're told one investing rule from the beginning: don't put all your eggs in one basket. But does owning more stocks actually make you wealthier, or does diversification mainly protect you when you're wrong? 📈

In this episode of the Limitless Podcast, Dr. Matthew Preston and Dr. Thaon Simms break down concentration vs diversification, position sizing, conviction, risk, and the uncomfortable truth that no amount of research can remove uncertainty.

They also get into a question every investor should ask: if you've ranked your best investment ideas by conviction, why are you taking money away from your best idea to put it into your tenth-best idea?

The answer gets to the heart of diversification. Your research can be good and your conviction can be high, but your ranking can still be wrong.

📊 Highlights & Chapters:

0:00 - 5:31 | 🥚 Why Investors Are Told to Diversify
5:31 - 10:16 | 🛡️ Diversification as Risk Management
10:16 - 15:43 | 🎯 Being Right vs Concentrating Your Money
15:43 - 20:33 | 💰 How Concentration Can Build Wealth
20:33 - 25:27 | ✈️ Survivorship Bias and Learning From Failure
25:27 - 31:53 | 📊 Position Sizing, Conviction and Uncertainty
31:53 - 38:33 | 🔍 Can Concentration Actually Reduce Risk?
38:33 - 44:50 | 💵 Does Diversification Change as You Get Richer?
44:50 - 48:51 | 🤔 Why Own Your Tenth-Best Investment Idea?
48:51 - 51:28 | 🧺 How Many Stocks Should You Actually Own?

🎧 Listen to more episodes: https://limitlesspodcast.buzzsprout.com
🐥 Follow us on Twitter: https://twitter.com/Limitless_pod
📷 Stay connected on Instagram: https://www.instagram.com/limitless_pod/
💲 Get exclusive insights: https://bit.ly/Limitless-MMJA-Discount

👍 If you enjoyed this episode, please like, subscribe, and share!

❓ What's the fewest number of stocks you would feel comfortable owning in your portfolio? One? Two? Five? Ten? Tell us in the comments.

⚠️ Disclaimer: The opinions expressed in this podcast are solely those of the hosts and do not constitute financial advice. Please consult a financial advisor before making any investment decisions.

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Why does the IMF still bring back memories of hard times for so many Jamaicans?

Dr. Matthew Preston and Dr. Thaon Simms sit down with Julian Morrison, “Dr. Doom,” to trace Jamaica’s economic story from the oil shocks and currency problems of the 1970s and 1980s through FinSAC, IMF austerity, JDX, NDX and the reforms that followed.

The conversation explains why Jamaica kept borrowing, why debt restructuring was so painful, how EPOC helped rebuild confidence, and how falling government interest rates eventually pushed more capital toward the Jamaica Stock Exchange.

Then the discussion turns to investors: What would it take for the JSE to return to its 2016–2019 form? Julian breaks down the role of interest rates, liquidity, market sentiment and earnings—and argues that when it comes to moving stock prices, flows and perception can matter before fundamentals.

📊 Highlights & Chapters:

0:00 - 12:58 | 🏦 What the IMF Actually Does

12:58 - 21:20 | 📉 Inflation, Interest Rates & Government Debt

21:20 - 39:48 | 🇯🇲 How Jamaica’s Debt Crisis Took Shape

39:48 - 1:01:47 | 💥 FinSAC, Austerity, JDX & Jamaica’s Credit Rating

1:01:47 - 1:16:05 | 🔄 NDX, EPOC & the Debt Turnaround

1:16:05 - 1:31:06 | 💵 IMF Reform, BFIXIT & Jamaica’s Recovery

1:31:06 - 1:38:44 | 📈 What Would Make the JSE Boom Again?

1:38:44 - 1:45:19 | 🧠 APOs, Liquidity & Market Sentiment

1:45:19 - 1:54:26 | 🏦 Scotia, NCB & the Cost of Capital

1:54:26 - 2:03:14 | 💰 Dividends, Investor Flows & What Moves Stocks

🎧 Listen to more episodes: https://limitlesspodcast.buzzsprout.com
🐥 Follow us on Twitter: https://twitter.com/Limitless_pod
📷 Stay connected on Instagram: https://www.instagram.com/limitless_pod/
💲 Get exclusive insights: https://bit.ly/Limitless-MMJA-Discount

👍 If you enjoyed this episode, please like, subscribe, and share!

❓ What do you think matters most for another JSE boom: lower interest rates, stronger earnings, or better investor sentiment?

⚠️ Disclaimer: The opinions expressed in this podcast are solely those of the hosts and do not constitute financial advice. Please consult a financial advisor before making any investment decisions.

Send us Fan Mail

Support the show