Matt Gray is a serial entrepreneur who’s built three successful companies, scaled teams of 50+, and grown an audience of over 14 million people. He’s best known as the founder of
Herb, the world’s largest cannabis wellness platform, backed by investors like Joe Montana and the CEO of Shopify. He’s also the founder of
Founder OS, a system and community helping founders scale their online businesses through proven frameworks, lead engines, and organic content. In this episode, Matt shares battle-tested insights on scaling startups, creating content, legalising cannabis, and living with purpose.
00:00 Matt’s entrepreneurial background & the start of Herb
03:58 Learning to code & building practical skills
05:40 Facing a $1M fine & potential jail time
10:50 Navigating fear & uncertainty in business
14:30 Nature, travel & the joy of simplicity
17:40 The pros & cons of personal brand building
20:45 Long-term planning & using deadlines
22:40 Medicinal cannabis & advocating for alternatives
27:50 The case for legalisation & addressing side effects
32:50 Chat with Andrew Huberman: cannabis & testosterone
34:34 How cannabis affects mood, energy & creativity
35:55 Discovering purpose through Ikigai
43:36 Embracing failure & repetition
47:20 Common founder pitfalls & how to overcome them
51:20 Scaling your business into a passive system
54:10 Best marketing platforms & power of long-form
1:00:30 Content strategy & team building
1:07:15 Essential tools to streamline growth
1:11:27 2024 goal setting & planning
1:18:31 Do you need a morning routine to succeed?
1:22:40 Japan, India & moving to Dubai
1:26:02 Gut instinct & advice for those feeling stuck
1:30:44 Staying productive while travelling
1:34:36 Enjoying youth & reflecting on your 20s
1:39:50 How to spend wisely & raise your hourly rate
1:47:02 Health, habits & working with your partner
1:52:04 Planning for 2024 & achieving balance
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