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

When to sell stocks, taking profits, stock market, investing for beginners, portfolio management, risk management, how to invest, asset allocation, portfolio concentration, high beta stocks, blue chip stocks, energy stocks, tech stocks, AI stocks, data center stocks, Google stock, Amazon stock, Crowdstrike stock, Rocket Lab stock, Wall Street Wildlife, investing podcast

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