Dan Hillery joins us today for Episode 2 of the Proof of Thought Podcast. Is there a smarter way to invest in Bitcoin and everything surrounding it? This will change how you think about wealth, risk, and opportunity in the next decade.
*This video was recorded April 17, 2025.
Dan reveals:
▫️ How he transitioned from simple index funds to going all in on Bitcoin
▫️ Why he shifted part of his BTC allocation to Strategy (formerly MicroStrategy) stock—and what most investors miss
▫️ The #1 risk he sees for Bitcoin today
▫️ How he uses first principles thinking to analyze memecoins, options, and market cycles
▫️ The entrepreneurial insights that led him to create his own options platform, Achilles Intelligence
▫️ Why he believes MSTR options are in a league of their own
▫️ What Dan would never do with his own Bitcoin—and why
The information in this episode is for educational purposes only and should not be considered financial advice. Always do your own research or speak to a licensed financial advisor before making any investment decisions.
Timestamps:
00:00 Intro
01:30 Starting Young in Investing
04:09 From Index Funds to Bitcoin
06:51 Navigating Risk With Bitcoin & MSTR
09:24 BTC vs. MSTR Allocation Strategy
10:29 Rebalancing Over Time
12:28 The Biggest Risks to Bitcoin and MSTR
14:15 How Dan Handles Market Shocks
16:49 The Investors Who Shaped His Thinking
18:58 Bitcoin vs. Altcoins
21:05 First Principles: Memecoins & Expected Value
25:20 First Principles: Why MSTR Options Are in a League of Their Own
29:55 First Principles: Why MSTR Trades at a Premium to NAV
36:35 First Principles: MSTR vs. MSTY vs. STRK vs. STRF
46:59 Entrepreneurial Opportunities in Crypto
49:23 Why He Created Achilles Intelligence
51:38 Early Investing Mistakes and Lessons
54:32 Most Interesting Bitcoin Innovation Today
55:24 Dan’s Personal Social Media Content Strategy
56:09 Would He Ever Loan Out His Bitcoin?
57:07 Dan’s North Star
59:05 What Dan Is Reading and Listening To
1:00:17 Where to Follow Dan
Follow Dan:
Dan on X - https://x.com/hillery_dan?lang=en
Dan on YouTube - https://www.youtube.com/@UCazR7E8kze4_JD35aJQMa2Q
LinkedIn - http://linkedin.com/in/daniel-hillery-898255226
Achilles Intelligence Website - http://achilles-intelligence.com
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