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. #aspirewithemmagrede #podcast #entrepreneur #business #businessadvice #interview #successmindset #sharktank #shopify #shopifydropshipping #founder 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 _____ SUBSCRIBE    / @emmagrede   _____ Buy Emma's Book: START WITH YOURSELF is yours April 2026! Preorder today wherever you buy books or at https://www.emmagrede.com/ _____ 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/