What happens when you're too successful? In this special episode, we're tackling the best problem an investor can have: a winning stock that's grown so big it's unbalancing your entire portfolio. Before we hit episode 100, we flip the script to find the answers.

🦡 The Bull Case for CHAOS: Badger defends a high-risk, high-reward energy portfolio. Is this volatile strategy right for you?

🐒 In Praise of "Boring": Monkey explains why owning "tuxedo and Rolex" stocks like Google and Amazon is a powerful long-term strategy for building wealth. $GOOG $AMZN

✂️ When to Sell a Winner: We answer your #1 question. Learn the stock-specific and portfolio-level signs that it's time to take some profits off the table.

🏢 Go on Stock Safari with White Fiber - could a company retrofitting old buildings into the high-demand data centers of the future be the next AI Play? $WYFI

📊 Our Biggest Portfolio Mistakes: From a 1000% gain creating a 15% position to a single stock ballooning to 35%, we reveal our own risk management blunders.

💡 The Ultimate Litmus Test: Steal our simple but powerful "Would I Buy It Today?" framework to stress-test every single holding in your portfolio.

Segments:

00:00 Cold Open & Contest Announcement

07:20 Portfolio Role Reversal Setup

09:28 Luke's Bull Case for Monkey's Portfolio

13:15 Krzys's Defense of Badger's Strategy

27:54 Self-Critique and Portfolio Problems

46:31 The Trimming Question from Listeners

54:55 White Fiber Stock Safari

01:05:30 Family Investing Conversations

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If you want to see our furry faces, this podcast is also available on YouTube at ⁠https://www.youtube.com/@WallStreetWildlife?sub_confirmation=1⁠

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SUPPORT THE SHOW AND BECOME A PATREON:

https://patreon.com/wallstreetwildlife

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Find more episodes of the podcast at ⁠⁠⁠wallstreetwildlife.com⁠⁠⁠ where you can also get our "10 Laws of the Investing Jungle" free PDF download, and you can follow us at:

⁠⁠x.com/7LukeHallard

⁠x.com/7FlyingPlatypus

Wall Street Wildlife is also on Instagram @wallstreetwildlife

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Fiscal.AI is the Complete Stock Research Platform for fundamental investors. With its beautiful design and institutional-quality data, Fiscal AI is incredibly powerful and easy to use.

Get 15% off any premium plan with:

https://fiscal.ai/wildlife

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Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube

https://open.spotify.com/show/4SBtOWGEOmD9pmltgIXO8r

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To use the same portfolio tracking tool as Luke, check-out:

⁠https://www.portseido.com/?fpr=lukehallard

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Monkey’s “Zen, Nietzsche, How to Live” Substack:

http://firephilosophy.substack.com

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Disclosure: Wall Street Wildlife hosts and guests are not financial advisors, and nothing they say on this show is formal advice or a recommendation

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Keywords

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