Founder2Founder with Aaron Spivak
Entrepreneurship isn’t just a career—it’s a relentless, all-consuming way of life.
Welcome to Founder2Founder a raw and unfiltered podcast where host Aaron Spivak pulls back the curtain on what it really takes to build something from the ground up. No sugarcoating, no overnight success stories—just deep, honest conversations with some of the most driven, underrated, and game-changing founders of our time. From brutal setbacks to game-changing mindset shifts, Aaron goes beyond the polished success stories to uncover the unglamorous, deeply personal side of building a business.
As a seasoned entrepreneur himself, Aaron goes beneath the surface and gets into the nitty-gritty of what it truly takes to succeed. He’ll dive into the habits, behaviors, and routines that set elite founders apart, the tactics and strategies that are working today, and the mindset shifts required to push through the hardest moments. Through raw personal stories, late-night struggles, and breakthrough moments, guests open up about what it really means to grow, not just as a founder, but as a person.
Each week, Aaron sits down with visionary entrepreneurs from high-growth startup founders to seasoned CEOs, for real, unfiltered conversations about the highs, lows, and everything in between. Whether you're scaling a company, launching your first venture, or just looking for inspiration, this podcast will give you the insights, motivation, and real-world advice you won’t get just anywhere. If you're ready to strip away the illusion and get real about what it means to build, sacrifice, and thrive, this is the podcast for you. Join us every Wednesday!
Founder2Founder with Aaron Spivak
The 3 Traits Every High-Growth Brand Shares, According to Shopify’s President Harley Finkelstein
In this special episode of Founder2Founder, Aaron Spivak sits down with Harley Finkelstein, President of Shopify, for a no-fluff, behind-the-scenes conversation recorded live with over 100 Founders Club members. Harley unpacks the deep connection between personal identity and building lasting companies, while discussing how founders can grow smarter and why success demands unshakable character and long-term thinking.
This isn’t a surface-level chat, Harley dives into the psychological drivers behind great founders, how AI is changing hiring and operations, and why you should fire yourself before it’s too late. He shares tactical insights on platform strategy, what Shopify looks for in celebrity-led brands, and how to build a company that’s authentic, resilient, and scalable. From DJing at 13, to leading one of the most iconic tech companies globally, Harley’s founder journey is packed with clarity and conviction that every entrepreneur can learn from.
Chapters:
01:28 – Balancing Personal Brand vs. Business Brand
06:49 – Why Founders Must Go Direct (and Skip Legacy Media)
07:27 – 3 Traits of the Most Successful Brands
12:45 – How AI is Replacing Full-Time Roles at Shopify
14:20 – Growing Firebelly Tea with Fewer People and More Energy
15:47 – Hire Founders, Not Résumés
17:44 – Why Shopify is Run by Founders (and How That Works)
19:06 – Harley’s Grandfather & Building with Character
23:49 – Work-Life Integration & Founders in Relationships
28:11 – Daily Habits, Self-Awareness & Why Harley Meditates
31:29 – The Only Meetings Harley Never Misses
34:38 – When Shopify Builds In-House vs. Letting Apps Thrive
40:35 – What Business Are You Really In? Harley Coaches a Founder Live
46:12 – How to Stop Losing DTC Sales to Amazon
50:01 – Why It Doesn’t Matter Where the Sale Happens
50:44 – Shopify’s Celebrity Strategy (It’s Not About Fame)
55:50 – Harley’s Final Ask: Help a Founder IPO
Guest Links:
Instagram: @Harley & @Shopify
Website: https://www.shopify.com
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Website www.foundersclubofficial.com
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