In this September 2026 Mailbag, Jason and Jeff tackle listener questions on when it makes sense to "average up" on massive winners, analyzing David Gardner’s contrarian approach to building a Rule Breaker portfolio. The hosts then explore the specific valuation and counter-cyclical margin arguments behind Jason's recent purchase of The TJX Companies, and debate the psychology of co-managing spousal IRAs. To close the episode, the duo reviews listener submissions for a "5 Stocks for 10 Years" portfolio, ultimately drafting their own hypothetical decades-long portfolios from the audience's picks.
02:03 Patreon Shoutout
03:07 Rapid Fire Housekeeping
04:15 Mailbag Begins
04:58 Double Down Winners
16:50 TJX Valuation Debate
24:42 ResMed Growth Outlook
28:20 When to Take Profits
29:56 When Valuation Matters
31:50 Couples Managing IRAs
34:49 Risk Across Net Worth
38:18 Spreadsheets And Aggregation
43:06 Five Stocks For 10 Years
44:19 Discord Picks Breakdown
48:23 Picking Five From The List
Companies mentioned: AER, AMZN, ASML, AXON, BAM, BN, BRK.B, COST, CVX, ISRG, LLY, LMND, MA, MEDP, META, RBRK, RMD, SBUX, TBBB, TJX, TSM
Find where to listen & subscribe,  portfolio contests, and contact information at <a href="https://investingunscripted.com">https://investingunscripted.com</a>
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To get 15% off any paid plan at fiscal.ai, visit <a href="https://fiscal.ai/unscripted">https://fiscal.ai/unscripted</a>
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Join our <a href="https://www.patreon.com/investingpod">Patreon</a>
Subscribe to our portfolio on <a href="https://savvytrader.com/investingunscripted/investing-unscripted-portfolio?s=MjM0NDM6NTQ1OA==">Savvy Trader</a>. Use code Unscripted2026 for 30% off a one-year subscription! Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices">megaphone.fm/adchoices</a>

In this September 2026 Mailbag, Jason and Jeff tackle listener questions on when it makes sense to "average up" on massive winners, analyzing David Gardner’s contrarian approach to building a Rule Breaker portfolio. The hosts then explore the specific valuation and counter-cyclical margin arguments behind Jason's recent purchase of The TJX Companies, and debate the psychology of co-managing spousal IRAs. To close the episode, the duo reviews listener submissions for a "5 Stocks for 10 Years" portfolio, ultimately drafting their own hypothetical decades-long portfolios from the audience's picks. 02:03 Patreon Shoutout 03:07 Rapid Fire Housekeeping 04:15 Mailbag Begins 04:58 Double Down Winners 16:50 TJX Valuation Debate 24:42 ResMed Growth Outlook 28:20 When to Take Profits 29:56 When Valuation Matters 31:50 Couples Managing IRAs 34:49 Risk Across Net Worth 38:18 Spreadsheets And Aggregation 43:06 Five Stocks For 10 Years 44:19 Discord Picks Breakdown 48:23 Picking Five From The List Companies mentioned: AER, AMZN, ASML, AXON, BAM, BN, BRK.B, COST, CVX, ISRG, LLY, LMND, MA, MEDP, META, RBRK, RMD, SBUX, TBBB, TJX, TSM Find where to listen & subscribe, portfolio contests, and contact information at https://investingunscripted.com ***************************************** To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted ***************************************** Join our Patreon Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription! Learn more about your ad choices. Visit megaphone.fm/adchoices

In this September 2026 Mailbag, Jason and Jeff tackle listener questions on when it makes sense to "average up" on massive winners, analyzing David Gardner’s contrarian approach to building a Rule Breaker portfolio. The hosts then explore the specific valuation and counter-cyclical margin arguments behind Jason's recent purchase of The TJX Companies, and debate the psychology of co-managing spousal IRAs. To close the episode, the duo reviews listener submissions for a "5 Stocks for 10 Years" portfolio, ultimately drafting their own hypothetical decades-long portfolios from the audience's picks.
02:03 Patreon Shoutout
03:07 Rapid Fire Housekeeping
04:15 Mailbag Begins
04:58 Double Down Winners
16:50 TJX Valuation Debate
24:42 ResMed Growth Outlook
28:20 When to Take Profits
29:56 When Valuation Matters
31:50 Couples Managing IRAs
34:49 Risk Across Net Worth
38:18 Spreadsheets And Aggregation
43:06 Five Stocks For 10 Years
44:19 Discord Picks Breakdown
48:23 Picking Five From The List
Companies mentioned: AER, AMZN, ASML, AXON, BAM, BN, BRK.B, COST, CVX, ISRG, LLY, LMND, MA, MEDP, META, RBRK, RMD, SBUX, TBBB, TJX, TSM
Find where to listen &amp; subscribe,&nbsp; portfolio contests, and contact information at <a href="https://investingunscripted.com" rel="noopener noreferrer">https://investingunscripted.com</a>
*****************************************
To get 15% off any paid plan at fiscal.ai, visit <a href="https://fiscal.ai/unscripted" rel="noopener noreferrer">https://fiscal.ai/unscripted</a>
*****************************************
Join our <a href="https://www.patreon.com/investingpod" rel="noopener noreferrer">Patreon</a>
Subscribe to our portfolio on <a href="https://savvytrader.com/investingunscripted/investing-unscripted-portfolio?s=MjM0NDM6NTQ1OA==" rel="noopener noreferrer">Savvy Trader</a>. Use code Unscripted2026 for 30% off a one-year subscription! Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices" rel="noopener noreferrer">megaphone.fm/adchoices</a>

225. September 2026 Mailbag

Jason and Jeff discuss the possibility of another market crash in 2022, and what investors can do to prepare both their portfolios and their mindset for the next market downturn.
 Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices">megaphone.fm/adchoices</a>

Jason and Jeff discuss the possibility of another market crash in 2022, and what investors can do to prepare both their portfolios and their mindset for the next market downturn. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jason and Jeff discuss the possibility of another market crash in 2022, and what investors can do to prepare both their portfolios and their mindset for the next market downturn.
 Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices" rel="noopener noreferrer">megaphone.fm/adchoices</a>

7. Will There Be Another Market Crash This Year?

More than 20 years after its founding, MercadoLibre is still one of the best growth stocks to own. In this episode, Jeff and Jason discuss its position, how it's already been a big winner for Jason, and why he's continued to buy shares even after earnings more than 12X returns on his initial investment.
 Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices">megaphone.fm/adchoices</a>

More than 20 years after its founding, MercadoLibre is still one of the best growth stocks to own. In this episode, Jeff and Jason discuss its position, how it's already been a big winner for Jason, and why he's continued to buy shares even after earnings more than 12X returns on his initial investment. Learn more about your ad choices. Visit megaphone.fm/adchoices

More than 20 years after its founding, MercadoLibre is still one of the best growth stocks to own. In this episode, Jeff and Jason discuss its position, how it's already been a big winner for Jason, and why he's continued to buy shares even after earnings more than 12X returns on his initial investment.
 Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices" rel="noopener noreferrer">megaphone.fm/adchoices</a>

6: Why is MercadoLibre Jason's Biggest Stock Holding?

That stock you paid $10 for just fell to $5. Where did the money go? Jason and Jeff answer this question and provide some resources for investors who want to learn more.
 Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices">megaphone.fm/adchoices</a>

That stock you paid $10 for just fell to $5. Where did the money go? Jason and Jeff answer this question and provide some resources for investors who want to learn more. Learn more about your ad choices. Visit megaphone.fm/adchoices

That stock you paid $10 for just fell to $5. Where did the money go? Jason and Jeff answer this question and provide some resources for investors who want to learn more.
 Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices" rel="noopener noreferrer">megaphone.fm/adchoices</a>

5. Where Did My Money Go?

In this episode, Jason and Jeff answer two listener questions about building a dividend-focused portfolio, as well as stocks you can set and forget. 
 Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices">megaphone.fm/adchoices</a>

In this episode, Jason and Jeff answer two listener questions about building a dividend-focused portfolio, as well as stocks you can set and forget. Learn more about your ad choices. Visit megaphone.fm/adchoices

In this episode, Jason and Jeff answer two listener questions about building a dividend-focused portfolio, as well as stocks you can set and forget.&nbsp;
 Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices" rel="noopener noreferrer">megaphone.fm/adchoices</a>

4. Mailbag: Listener Questions

Jason and Jeff discuss the rising interest rate environment and what it means for stocks and the return investors can expect.
 Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices">megaphone.fm/adchoices</a>

Jason and Jeff discuss the rising interest rate environment and what it means for stocks and the return investors can expect. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jason and Jeff discuss the rising interest rate environment and what it means for stocks and the return investors can expect.
 Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices" rel="noopener noreferrer">megaphone.fm/adchoices</a>

3. What Do Rising Interest Rates Mean for Stocks?

How much do you need to retire? How much is your "enough"? Jason and Jeff tackle this question as well as discuss recent economic events in order to determine if they're news or noise.
 Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices">megaphone.fm/adchoices</a>

How much do you need to retire? How much is your "enough"? Jason and Jeff tackle this question as well as discuss recent economic events in order to determine if they're news or noise. Learn more about your ad choices. Visit megaphone.fm/adchoices

How much do you need to retire? How much is your "enough"? Jason and Jeff tackle this question as well as discuss recent economic events in order to determine if they're news or noise.
 Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices" rel="noopener noreferrer">megaphone.fm/adchoices</a>

2. What is Your Enough?

This is The Smattering Podcast, where we ask the questions that matter to investors.
 Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices">megaphone.fm/adchoices</a>

This is The Smattering Podcast, where we ask the questions that matter to investors. Learn more about your ad choices. Visit megaphone.fm/adchoices

This is The Smattering Podcast, where we ask the questions that matter to investors.
 Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices" rel="noopener noreferrer">megaphone.fm/adchoices</a>

1. What is The Smattering?

Welcome to Investing Unscripted, where we ask the hard questions about investing, the stock market, and personal finance. 

We don't have THE answers, we only have OUR answers.

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Welcome to Investing Unscripted, where we ask the hard questions about investing, the stock market, and personal finance. We don't have THE answers, we only have OUR answers.

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