v1.43 - Don’t Let Bad Deals Kill Your Investment Strategy episode artwork

EPISODE · Oct 31, 2025 · 25 MIN

v1.43 - Don’t Let Bad Deals Kill Your Investment Strategy

from Wealth Independence Podcast · host Dustin Bailey & Adam Penn

Dustin and Adam tackle a critical topic many passive investors face: recovering from investment losses and knowing when to get back in the market.After reaching out to investors about a new investment opportunity, Adam noticed a pattern: roughly 10% responded that they’d lost money in multiple deals and were writing off entire investment categories as a result.The discussion covers why this reaction, while understandable, often prevents investors from capitalizing on current opportunities, and explores the importance of learning from losses rather than letting them sideline you completely, particularly as market cycles shift.While both Dustin and Adam have been seeing more quality deals in the last 6-9 months than in the previous few years, they examine why now may be an opportune time to deploy capital…but only with proper position sizing and due diligence.Key topics include: recognizing where we are in market cycles, the danger of over-allocating during peak times, position sizing strategies (limiting any single deal to a percentage of net worth), and how to analyze what went wrong in failed investmentsWatch episode on YouTube: https://www.youtube.com/watch?v=7oGIsyiNSuoSee all Wealth Independence episodes at https://www.wealthindependencepod.comConnect with Dustin:Big Spring CapitalLinkedIn (/in/TheDustinBailey)Twitter/X (@TheDustinBailey)Connect with Adam:Bidwell CapitalLinkedIn (/in/AdamJPenn)This show is for informational purposes only and is not financial, investment, legal, or tax advice, and does not constitute an offer to buy or sell securities. All investments carry risk, and investors should always conduct thorough due diligence and consult with qualified professionals before investing.

Dustin and Adam tackle a critical topic many passive investors face: recovering from investment losses and knowing when to get back in the market. After reaching out to investors about a new investment opportunity, Adam noticed a pattern: roughly 10% responded that they’d lost money in multiple deals and were writing off entire investment categories as a result. The discussion covers why this reaction, while understandable, often prevents investors from capitalizing on current opportunities, ...

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v1.43 - Don’t Let Bad Deals Kill Your Investment Strategy

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This episode was published on October 31, 2025.

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Dustin and Adam tackle a critical topic many passive investors face: recovering from investment losses and knowing when to get back in the market.After reaching out to investors about a new investment opportunity, Adam noticed a pattern: roughly 10%...

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