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In this powerful episode of The Money Mondays podcast, host Dan Fleyshman sits down with entrepreneur and investor Matt Morgan, who built over $1 billion in cannabis companies before transitioning to passive investing in crypto, tech, AI, and real estate. The discussion centers on the three core pillars of the show: how to make money, how to invest money, and how to give it away to charity. (02:32)
Matt shares raw insights about fear being the primary barrier to financial success, the dangers of lifestyle creep, and why Bitcoin represents the first truly fair monetary system in human history. The conversation explores how AI will revolutionize the economy, the convergence of artificial intelligence with blockchain technology, and the critical importance of health as the ultimate wealth category. (11:00)
Dan Fleyshman is the host of The Money Mondays podcast, which ranks #25 globally out of 5.4 million podcasts. He's an experienced entrepreneur and investor who focuses on educating audiences about making money, investing money, and giving to charity through accessible, ad-free content designed for busy professionals.
Matt Morgan is an entrepreneur and investor who built over $1 billion worth of cannabis companies between 2010-2020, including the well-known Reef dispensary brand. Born and raised on a farm in Montana, he's lived across major warm-weather cities and has been operating as a semi-retired passive investor since 2020, focusing on crypto, tech, AI, and real estate investments. He's known for his expertise in cryptocurrency markets and biohacking.
Matt Morgan identifies fear as the biggest obstacle preventing people from achieving financial success. (03:02) He argues that most people cling to the security of a guaranteed paycheck every two weeks, which keeps them trapped in lower-income brackets. The fear of losing that steady income prevents them from taking calculated risks that could lead to significant wealth building. This insight is particularly relevant for ambitious professionals who may have entrepreneurial ideas but hesitate to leave their corporate jobs. Morgan suggests that on their deathbeds, people's biggest regret is not taking more chances in life, emphasizing the importance of overcoming fear-based decision making.
Both speakers emphasize the dangerous trap of lifestyle inflation that destroys wealth accumulation. (03:45) Dan Fleyshman provides specific guidance: while it's acceptable to buy your first luxury watch or car as motivation, you'll never emotionally care about your third watch or third car. The money spent on additional luxury items should instead be reinvested into appreciating assets or business opportunities. This principle is crucial because many entrepreneurs increase their overhead as their income grows, leaving them vulnerable when market conditions change or they need liquidity for new opportunities.
Morgan presents a compelling case for Bitcoin as a revolutionary monetary system. (08:00) He argues that traditional currencies are fundamentally flawed because small groups of people can print unlimited amounts, devaluing everyone else's savings. Bitcoin's fixed supply of 21 million coins creates scarcity that traditional assets like gold cannot match, since gold supplies can be increased through mining. With Bitcoin being the fastest appreciating asset in human history and directly correlated to market liquidity cycles, Morgan believes most investment capital should be allocated here during current market conditions.
The discussion reveals how AI agents will fundamentally reshape the economy and cryptocurrency adoption. (13:30) As AI takes over 90% of jobs, these intelligent agents will only accept cryptocurrency payments because they operate on pure logic and mathematics, rejecting unlimited-supply fiat currencies. Morgan predicts that AI agents operating on blockchain rails will handle everything from taxes to complex business operations, with all transactions occurring in cryptocurrency. This convergence represents what he calls "the largest transfer of wealth you'll ever see in human history," with potentially half of the world's $900 trillion in wealth moving onto blockchain systems.
The speakers connect health optimization directly to financial planning, noting that today's children will likely live over 100 years. (33:08) If someone retires at 75 and lives to 108, they need 33 years of savings - potentially $2 million just to survive on $60,000 annually. Morgan's personal transformation from burnout to biohacking expert illustrates how investing in health through advanced treatments, supplements, and regenerative medicine can extend productive earning years. With gene therapy and anti-aging treatments advancing rapidly, maintaining health becomes crucial for both quality of life and extended wealth-building opportunities.