Harley Finkelstein — Strategies from Shopify, the Future of Retail, and More | The Tim Ferriss Show

In this episode of The Tim Ferriss Show, Tim interviews Harley Finkelstein, the COO of Shopify, discussing Shopify's evolution into a retail operating system and its mission to empower entrepreneurs. Harley shares formative books, including "High Output Management" and "Anti-Fragile," and recounts his journey from selling t-shirts to joining Shopify, emphasizing the importance of mentorship and continuous self-improvement. The conversation explores Shopify's early fundraising, the Build a Business competition, and the future of retail, highlighting the shift towards direct-to-consumer models and the need for businesses to be resilient and adaptable. Harley also discusses the value of coaching, mindfulness, and scheduling, and reflects on the importance of having supportive companions throughout one's entrepreneurial journey.