Brad Mills is a Bitcoin OG (in since 2011), entrepreneur, and angel investor. In this episode, we talk about what it actually looks like to think long-term in Bitcoin, how he invests without selling, and why “AI agents + Bitcoin” might be the first truly mainstream crypto use case.

We get into real founder stuff too: leadership failures, scaling mistakes, decision fatigue, and how Brad rebuilt his habits using a “proof of work” mindset.

What we cover:

• Brad’s first “business” at 8 years old, and the Facebook app that hit massive scale
• The moment he realized “buy and hold Bitcoin” outperformed his highest-effort businesses
• Borrowing against Bitcoin: why LTV discipline matters and how people get wiped out
• Why gold confiscation (6102) is not the same risk model as Bitcoin custody today
• Quantum risk: what’s real, what’s noise, and how upgrades likely happen
• Why AI agents choosing Bitcoin is a bigger deal than retail adoption
• “Citadel mind and body”: applying Bitcoin-style consistency to health and relationships
• Books that actually changed his execution

Chapters / Timestamps

00:00 Intro, “Bitcoin is up 3x since 2022”
01:40 Brad’s first business at 8 years old
04:00 Growing up in poverty, learning to hustle
04:30 Hacky sack business and early entrepreneurship
05:40 “How do I make money online?” and getting scammed
06:15 The Facebook “Roll Up The Rim” app and the cease & desist
07:10 Monetization at scale, then getting crowded out
08:40 Hiring 17 people, leadership reality check
11:55 When Bitcoin outperformed the entire company
12:10 Brad’s first Bitcoin in 2011 and the early volatility lessons
15:00 Failed mining partnership and why he stopped “doing too much”
19:00 Trading strategy vs just holding Bitcoin
21:05 Becoming an angel investor (Bitcoin-only)
21:45 Borrowing against Bitcoin, loans, and LTV discipline
28:15 Interest rates and banks eventually offering BTC loans
30:00 Canada, optionality, and the sovereign individual thesis
33:00 Gold confiscation (6102) and why it’s often misunderstood
36:05 Self-custody vs “in the bank vault” risk
38:45 Capital controls and how Bitcoin changes the game
41:30 Epstein/Bitcoin origin claims and why decentralization makes it irrelevant
45:20 This downturn: what feels different this cycle
50:55 Is quantum Bitcoin’s biggest risk?
52:00 Quantum soft fork talk + Saylor’s quantum task force
56:10 “Quantum treasure hunt” and lost coins as a volatility catalyst
01:00:25 Portfolio updates, Maple private AI compute, AnchorWatch insurance
01:02:15 Square/Cash App Bitcoin payments and orange-pilling merchants
01:03:45 AI agents using Bitcoin as default money
01:10:15 OpenClaw as “translator” for non-technical builders
01:12:30 CLAWI.AI, Mac mini vs VPS setups
01:12:40 Token burn reality ($150–$200/day)
01:13:45 “Citadel mind and body” and proof-of-work habits
01:23:00 Book recs: Buy Back Your Time, The Big Leap, If the Buddha Married
01:24:35 Wrap

The Arena
The Arena is a private Skool community for SaaS founders who are actively building and selling. I share real-time decisions, experiments, and assets as I use them while growing a bootstrapped SaaS.

No theory. No polish. Just execution.
Learn more at: https://www.skool.com/the-arena/