$200 to $500M: Greg Cassar’s Playbook for AI, Bitcoin & Building Wealth | OD #32

From $200 in his pocket to $500 million in online sales. Greg Cassar has spent 22 years building and scaling businesses, helped more than 350 companies grow, and coached over 150 Australian business owners through his mastermind, The Collective. Today he runs travel brands in the US, an e-commerce import business, and a portfolio spanning property, Bitcoin, AI tech and robotics ETFs. Oscar and Greg cover: • The $200 voucher that taught him "one" is the worst number in business: one employer, one income stream • His make it, keep it, multiply it framework for business owners • Why you need both cashflow and growth assets, not just one • Buying Bitcoin in 2017, holding through 12 corrections, and why managing your emotions matters more than timing • His views on government deficits, money printing and scarce assets • How he uses Claude, projects and "loop engineering" to run his businesses, and how AI took one company from 50 staff to under 10 • Why young Australians should be building AI skills now Connect with Greg: https://www.collective.com.au/ and https://www.businesswealthfreedom.com/ Thinking about buying property? Book a free strategy call with Asset Road: https://www.assetroad.com.au Follow us on Instagram @oscardonproperty and @assetroad for daily property insights. General information only. Nothing in this episode is personal financial advice, and the views of guests are their own. Cryptocurrency and other investments can be highly volatile, and past performance is not a reliable indicator of future performance. Consider your own circumstances and get professional advice before acting.