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

Stay Connected!
Aaron Spivak:
Instagram @‌Spivak
Linkedin

The Founders Club
Instagram @‌TheFoundersClub
Website www.foundersclubofficial.com

Founder2Founder:
TikTok @‌Founder2FounderPodcast
Youtube @‌Founder2Founder.Podcast