In Episode 31 of The Jake Woodhouse Podcast, I’m joined by Andrew Page to break down his investment philosophy, the power of early-stage investing, and the story behind building Strawman.com. We also discuss why Bitcoin is “the” asymmetric investment opportunity, the pros and cons of early-stage investing vs holding Bitcoin in self-custody, how misallocated capital distorts incentives, and why the political system desperately needs Bitcoin.
X: @sage_simian
TIMESTAMPS:
0:00 – Andrew’s Money and Investment Strategy
5:19 – What’s it like Working as a Broker?
11:31 – Early Stage Investing and Strawman.com
17:38 – What is Strawman.com?
21:20 – Andrew’s Bitcoin Journey
25:26 – Bitcoin’s Asymmetric Investment Opportunity
28:59 – Bitcoin vs Early Stage Investing
34:27 – Capital Misallocation: Vote with Your Money
41:36 – The Memes are True, Bitcoin Fixes This
48:27 – Bitcoin and Politics
56:32 – Why Politics Needs Bitcoin
1:06:39 – How to Connect with Andrew
In this illuminating episode, Jake welcomes Andrew Page, founder of Strawman.com, to unpack his journey from traditional small-cap equity investing to high-conviction Bitcoin advocate. Andrew starts by reflecting on his early career in brokerage and equity research, highlighting the structural incentives within finance to push trades regardless of conviction. Disillusioned by the industry’s misaligned interests, he built Strawman — a community of serious, self-directed ASX investors — to crowdsource and challenge ideas through play-money portfolios and collaborative research, emphasizing that “you can borrow an idea, but not conviction.”
Andrew shares how his obsession with equities — driven by intellectual curiosity and a pursuit of financial freedom — was gradually overtaken by the Bitcoin rabbit hole. Initially dismissive, he set out to debunk Bitcoin but came away fully orange-pilled, realizing it offered the most asymmetric risk/reward opportunity of his lifetime. The parallels between equity investing and Bitcoin — capital allocation, hurdle rates, risk modeling — all reinforced his conviction. He also makes a powerful case that Bitcoin is not right-wing, but rather post-political, with the potential to serve left-leaning goals like fairness, environmental sustainability, and poverty alleviation far better than current systems.
The conversation dives deep into the implications of hard money for early-stage capital formation. Jake and Andrew explore how Bitcoin’s presence as a “risk-free benchmark” radically shifts investment behavior, enforcing more discipline and drastically reducing malinvestment. They discuss the misallocation of capital in today’s fiat economy — notably in property and low-yield public programs — and how Bitcoin reintroduces opportunity cost, incentives, and accountability into capital decision-making.
Finally, Andrew reflects on the deeper, civilizational implications of Bitcoin: as a once-in-a-millennium shift in monetary technology, a peaceful revolution against coercion and corruption, and a system that forces reality-based decision-making. He urges listeners — regardless of political identity — to look beyond tribal labels and recognize Bitcoin as a neutral protocol for human coordination. Passionate, articulate, and grounded in decades of investing experience, Andrew’s perspective is a must-listen for anyone exploring Bitcoin through a financial lens.