

15 years. 3 businesses. 1 dream life (here’s how i did it) I EP 88
Jul 22, 2025
Journey through 15 years of entrepreneurial highs and lows! The host reflects on selling a business at 23 and starting anew in a van in New Zealand. Discover the chaos of a government raid that tested community bonds and the evolution from outcome focus to process appreciation. Learn how a pivotal email sparked a cannabis business transformation. Key insights on the power of email lists and intentional decision-making for sustained success are also shared, advocating for patience and persistence in personal and professional growth.
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Government Raid on First Business
- At 21, Matt Gray's first business was raided by the government for being mistaken as an unregistered college.
- He rallied support via email and social media, successfully getting an exemption and continuing operations.
Building Herb Cannabis Brand
- Matt bought a cannabis recipe site in New Zealand and rebranded it to Herb.
- He grew Herb into a 14 million audience, with a 27-person team, running mostly on automation.
Focus on Process Over Outcome
- Avoid focusing solely on outcomes like valuation; instead, fall in love with the process of building.
- Enjoy daily work, build systems, and focus on craftsmanship behind your brand to sustain happiness and growth.