🎧 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?

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❓ 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

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❓ 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.

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Jamaican investors love dividend stocks. But does a high dividend yield actually mean you're making more money?

In this episode of the Limitless Podcast, Dr. Matthew Preston and Dr. Thaon Simms compare some of the JSE's best-known dividend stocks. Instead of looking at the dividend alone, they compare it with changes in the share price to see what investors actually earned.

TransJamaica is one of the biggest surprises. Its current dividend yield isn't particularly high compared with other stocks on the list, but its share price climbed sharply over the period examined.

Guardian Holdings tells a different story. It tops the list for dividend yield, but its share price barely moved over the same period.

The discussion also covers Carreras, Fontana, GraceKennedy, Scotia Group, NCB Financial Group and several other JSE stocks.

If you're buying stocks for dividends, this episode asks a simple question: What happens to your total return when the share price moves against you?

📊 Highlights & Chapters:

0:00 - 5:59 | 💰 Why investors love dividend stocks
5:59 - 10:33 | 🚀 TransJamaica's 156% capital gain
10:33 - 15:38 | 🏆 The highest dividend yields on the JSE
15:38 - 19:24 | 📉 When capital losses wipe out your dividend
19:24 - 26:14 | 💊 Fontana's 4% dividend vs a falling share price
26:14 - 34:21 | 🌎 GraceKennedy's dividends and 2030 targets
34:21 - 39:30 | 🏦 Scotia's dividend and proposed buyout
39:30 - 47:13 | 💵 What price would make Scotia worth buying?
47:13 - 51:02 | 📈 NCB and the case for watching capital gains
51:02 - 51:59 | 🎯 Dividend yield vs total return

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❓ When you buy a stock, which matters more to you: the dividend yield or your total return?

⚠️ 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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Jermaine McDonald, co-founder of Learn Grow Invest, joins Dr. Matthew Preston and Dr. Thaon Simms to talk investing, the Jamaica Stock Exchange and the lessons that shaped his approach to building wealth.

Jermaine shares how he went from a J$2 million negative net worth to becoming an investor and educator, the mistakes he made early on, how FOMO affected his decisions, and why losing money eventually forced him to learn how to invest properly.

We also get into his current approach to the market, including why he only holds four stocks, why he no longer believes in simply buying and holding forever, and how he separates the bull case from the bear case when analysing a company.

The conversation also covers FESCO, RPL, Image Plus, JetCon, Indies Pharma, TransJamaica and other JSE stocks, including growth, valuation, investor sentiment and what can cause an investment thesis to change.

Jermaine also explains the responsibility that comes with talking about stocks publicly, including the surprising story of someone who bought a stock simply because he smiled while discussing it.

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❓ What is the biggest lesson you have learned from losing money in the stock market?

⚠️ 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.

#JamaicaStockExchange #JSE #LearnGrowInvest #InvestingJamaica #LimitlessPodcast

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SEPROD has put a five-for-one stock split, a major increase in authorized shares and the possibility of an Additional Public Offer on the table.

Dr. Matthew Preston and Dr. Thaon Simms break down what the announcement could mean for SEPROD shareholders and what the company may be preparing to do next.

We look at SEPROD's history of using cash and shares for acquisitions, the possibility of another major deal, dilution, debt repayment and how much capital the company could theoretically raise. At the upper end of the share capacity discussed in the episode, the numbers become enormous, potentially enough to fund an acquisition approaching the size of SEPROD itself.

Is the stock split mainly about making SEPROD more accessible to investors, or is it part of a much bigger plan?

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❓ What do you think SEPROD is raising capital for: an acquisition, debt reduction, expansion, or something else?

⚠️ 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 are Jamaica's public sector doctors taking industrial action, and how did a dispute over overtime pay reach this point?

On October 2, 2026, Jamaica's public sector doctors took industrial action, providing emergency services only.

JMDA President Dr. Jubilee Brown-Service joins Dr. Matthew Preston and Dr. Thaon Simms to explain the association's position, the dispute over emergency duty pay, the differing estimates of J$31 billion and J$23 billion, and why doctors are still waiting for a ruling from the Industrial Disputes Tribunal.

We also discuss 48- and 72-hour shifts, the effects of sleep deprivation, unpaid working hours, patient care and what a resolution could look like.

📊 Highlights & Chapters:

0:00 - 4:23 | 🎙️ Why Jamaica's doctors took industrial action

4:23 - 9:07 | 🩺 Meet the JMDA president and understand the association's role

9:07 - 14:05 | ⏰ What is the dispute over doctors' overtime pay?

14:05 - 17:54 | 😴 Long shifts, sleep deprivation and patient safety

17:54 - 22:01 | 📅 42 months waiting: The dispute and IDT proceedings

22:01 - 29:27 | 💰 J$31 billion vs J$23 billion and unpaid overtime

29:27 - 34:09 | ⚖️ Why negotiations failed and the dispute reached the IDT

34:09 - 37:54 | 🏥 Why doctors are still waiting for a ruling

37:54 - 43:13 | 🚑 Emergency services, patient care and a possible resolution

43:13 - 48:27 | 🎤 The JMDA president's message to doctors and the public

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❓ What questions do you still have about the doctors' overtime dispute or its effect on Jamaica's public healthcare system?

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Are dividends really the passive-income machine investors make them out to be? 📈💵 In this episode of the Limitless Podcast, Dr. Thaon Simms and Dr. Matthew Preston break down the truth about dividend investing, from dividend yields and taxes to capital gains, bonds, portfolio size, and the amount of money you may actually need before dividends materially change your life.

The hosts explore why a great dividend yield on a small portfolio can still produce relatively little cash 💸, why dividends are never guaranteed, and why investors need to consider total return instead of focusing only on income. They also discuss dividend investing on the Jamaica Stock Exchange 🇯🇲, using companies such as TransJamaican Highway, Carreras, NCB Financial Group, Jetcon and others as examples.

Could capital gains be more important while you're building wealth? And when might dividends finally become a bigger part of your strategy? 🤔

📊 Highlights & Chapters:

0:00 - 5:45 | 💰 Dividends, Capital Gains & Getting Paid Without Selling

5:45 - 10:07 | 🤔 Why Dividends May Not Change Your Life Yet

10:07 - 16:08 | 🧮 Dividend Yields, Taxes & What Investors Actually Receive

16:08 - 21:30 | 📉 The Risks Behind Dividend Investing

21:30 - 25:08 | ⚖️ Dividend Stocks vs Bonds

25:08 - 29:31 | 🏦 Bonds, Inflation & Putting Idle Cash to Work

29:31 - 34:25 | 💵 How Much Money Do You Need to Live Off Dividends?

34:25 - 39:12 | 📈 Capital Gains, Total Returns & Building Wealth

39:12 - 40:52 | 🎯 The Real Lesson for Dividend Investors

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❓ How much monthly dividend income would you need before dividends materially changed your life? 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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