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Cole Wilcox, Founder, CEO, and CIO of Longboard Asset Management, joins The Blunt Dollar to unpack the core ideas behind his 25-year investing journey rooted in disciplined risk management, long-term thinking, and trend following.
If you're exploring how to invest, curious about what it means to have a sound investment strategy, or simply want to understand personal finance through a deeper lens, this episode delivers timeless insights you can actually use.
We discuss the highs and lows of the stock market, how to protect your portfolio from catastrophic loss, and what investing for beginners should really look like in a world full of noise.
In this conversation, we cover:
📉 Why “avoiding the double zero” is the cornerstone of Cole’s approach to investing
📚 How early market cycles and losses shaped his take on how to invest in stocks and build lasting wealth
📊 What most get wrong about trend following and how it beats buy low sell high thinking
🧠 Why budgeting, patience, and emotional discipline matter more than stock picking
🔮 The rise of liquid alternatives, freenvesting, and what the future of retire stock market strategies may look like
If you're into stocks to buy, how to save money, and building a strategy that actually compounds, this one’s for you.
Oh, and if you haven't already... subscribe to The Blunt Dollar for more raw and honest finance conversations.
New episodes drop every other week! Available on Spotify, Apple Podcasts, and wherever you get your podcasts.
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Enjoy the episode!
Disclaimer: This podcast is for informational and educational purposes only. It does not constitute financial, investment, or legal advice. Listeners should consult a qualified financial professional before making any financial decisions.
