Behind every bold move is often a quiet fear. In this episode, I sit down with Shopify President Harley Finkelstein to talk about how anxiety has shaped his path from navigating family financial loss as a teenager to leading one of the world’s most influential platforms for entrepreneurs. Harley explains how to view anxiety not as a flaw, but as a tool that sharpens foresight, fuels ambition, and prepares you for what others can’t see. He also shares how to build your team that balances your energy and why vulnerability in leadership is your strength. Get ready to turn anxiety into your advantage!

In this Episode, You Will Learn

00:00 Meet Harley Finkelstein, President of Shopify.

05:45 How Harley turned survival-driven anxiety at 17 into his first business.

11:45 Tools Harley uses to manage anxiety.

16:15 How to use anxiety as a checklist for risk and anticipation.

21:00 How do you handle anxiety when it affects your leadership?

24:30 Why extroverts and introverts recharge differently.

27:00 The #1 skill every anxious achiever needs.

Resources + Links

Get a copy of my book - The Anxious Achiever

Watch the podcast on YouTube 

Find more resources on our website morraam.com

Follow

Follow me: on LinkedIn @morraaronsmele + Instagram @morraam

Follow Harley: on LinkedIn @harleyf + Instagram @harley