For Harley Finkelstein, president of Shopify, anxiety has always been his super power – even when he didn’t know how to put a label on it. Host Morra Aarons-Mele speaks with Finkelstein about the generational trauma of his grandparents, who survived the Holocaust, the anxiety of starting a business at age 17 to support his family, and how to channel anxiety ... Show More
Sep 3
Understand Your Family Ghosts At Work with Deborah Ancona
What if the patterns that helped you succeed are also holding you back at work? In this episode, I sit down with MIT professor Dr. Deborah Ancona to talk about how the “family ghosts” you carry from childhood can shape the way you handle authority, conflict, responsibility, perfe ... Show More
49m 7s
Aug 27
Penn and Kim Holderness on Neurodivergence And The Creative Journey
Do you ever feel like you're forcing yourself to work in ways that just don't fit how your brain works? In this episode, I sit down with Penn and Kim Holderness to talk about how understanding ADHD transforms the way you lead, create, and work together. Penn and Kim share how und ... Show More
38m 36s
Apr 2022
48: Harley Finkelstein on Entrepreneurship, Immigration, and Anxiety
Welcome to Episode 48 of The Madhappy Podcast. This week we are excited to welcome Harley Finkelstein onto the show to learn more about his mental health experiences and journey to becoming the President of Shopify. Peiman kicks off the episode asking Harley about his childhood, ... Show More
39m 56s
Jul 2025
Harley Finkelstein: You Must Requalify for Your Role, Every Year
Shopify’s Harley Finkelstein reveals the one standard that actually scales your career and your family. Harley shares why stepping down as COO was his hardest choice, the family motto that guides his daughters, and what makes someone good at storytelling. They discuss AI's real a ... Show More
1h 47m
Oct 2019
HBR Presents: The Anxious Achiever with Morra Aarons-Mele
On The Anxious Achiever, Morra Aarons-Mele explores the way anxiety, depression, and other mental health issues affect people at work – for better or worse. In this episode, she speaks with clinical psychologist Ellen Hendriksen and Arvind Rajan, the CEO of Cricket Health, about ... Show More
38m 7s
Oct 2025
Shopify President: Harley Finkelstein – Democratising Entrepreneurship, Empowering Founders, & the Tools That Build Global Businesses
The Gstaad Guy sits down with Harley Finkelstein, President of Shopify and one of the most influential voices in modern entrepreneurship, to discuss how technology is redefining capitalism by empowering anyone, anywhere, to start and scale a business. From equipping first-time fo ... Show More
1h 12m
Oct 2023
Moment 130: Shopify's President: The 1 Skill You MUST Have To Thrive In Business: Harley Finkelstein
In this moment, the President of Shopify, Harley Finkelstein, discusses why having a diverse skillset is the best way to stand out in your industry and a way of becoming invaluable. A lot of the time you may think that having diverse skills in the form of hobbies or curiosities a ... Show More
16m 55s
Apr 2023
How Managing Your Anxiety Can Make You a Better Leader
The business world has increasingly begun to recognize the importance of mental health, but we still have a long way to go in openly acknowledging our challenges with it. Writer, entrepreneur, and podcast host Morra Aarons-Mele says that when we take the time and energy to better ... Show More
29m 15s
May 2023
Shopify President: How To Become A Millionaire For The Price Of A Starbucks Coffee!
In this new episode Steven sits down with the Canadian entrepreneur and President of Shopify, Harley Finkelstein.
Harley was 17 years when we started his first company selling T-shirts at University. Later, while studying law at the University of Ottawa, Harley met the future co- ... Show More
1h 46m