Shopify President: How to Win in the Golden Age of Entrepreneurship | Aspire with Emma Grede

What separates the entrepreneurs who start… from the ones who win?

Harley Finkelstein (President of Shopify and the man who has worked with millions of founders) sits down with Emma Grede to reveal the hard-earned truths behind building a business that lasts. From the real reason most people never act on their ideas, to why the “golden age of entrepreneurship” is happening right now, Harley breaks down the mindset, tools, and strategy that turn dreamers into doers.

In this conversation, Harley shares:
-Why execution matters more than ideas
-How to start a business with no money, no network, and no experience
-The habits shared by the most successful founders on Shopify
-Why the cost of failure has never been lower
-What it takes to scale a business in today’s creator economy
-The mindset shift every entrepreneur must make to succeed

Emma and Harley go deep on the courage, grit, and resourcefulness needed to build something from nothing, and why someone watching this right now could be the next billion-dollar founder.

If you’re an aspiring entrepreneur, a builder, or someone sitting on an idea you’ve been too afraid to start… this episode is your blueprint.

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00:00:00 - Introduction
00:01:08 - Harley's origin story
00:03:36 - Breaking down barriers to entrepreneurship
00:08:13 - What makes entrepreneurs win
00:10:20 - Growing the pie vs taking a slice
00:15:30 - What never fails: story and mission
00:19:52 - Audience first, product second
00:24:48 - Ad Break
00:27:35 - Healthy disrespect for the status quo
00:32:14 - The Dairy Boy story
00:36:12 - How brands stay relevant
00:40:58 - Scaling without losing your soul
00:43:32 - Where entrepreneurs fail
00:46:43 - Ad Break
00:51:00 - From jack of all trades to spiky object
00:54:48 - Integration over separation
00:58:05 - The real secret to doing more
01:04:20 - Ad Break
01:09:50 - Requalifying for your job every year
01:15:06 - How to be too good to ignore
01:23:00 - Work-life harmony
01:28:22 - Hope for the next generation
01:33:18 - Rapid Fire
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Buy Emma's Book: START WITH YOURSELF is yours April 2026! Preorder today wherever you buy books or at https://www.emmagrede.com/

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ABOUT ASPIRE WITH EMMA GREDE
Build the life of your dreams and learn from the world’s most successful people.
Emma Grede, one of America’s richest self-made women, wants you to make the most of your life. On ‘Aspire with Emma Grede', learn through thought-provoking conversations with some of the most successful and smartest minds on the planet, including goop founder Gwyneth Paltrow, investor, philanthropist and former chair of Starbucks, Mellody Hobson, podcast host Jay Shetty, billionaire entrepreneur and Shark Tank star Mark Cuban, and public luminaries like Meghan, Duchess of Sussex, Charlamagne Tha God, Jessica Alba, former First Lady Michelle Obama, and Netflix Co-CEO Ted Sarandos. Each episode will unpack their habits, philosophy, and strategies, covering career advice, well-being, psychology, and, of course, how to win in business. The show offers personal stories, data-driven advice, real-world strategies, and the experience you need to turn your dreams into reality.

LISTEN TO ASPIRE WITH EMMA GREDE
link.pscrb.fm/f0281/Aspire_YT

ABOUT EMMA GREDE
Emma Grede is a founding partner and chief product officer of SKIMS and CEO of Good American. She also made history as the first Black woman to serve as an investor on Shark Tank. Learn more at: https://www.emmagrede.com/