Aspire with Emma Grede

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How to Win in the Golden Age of Entrepreneurship

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Dec 2, 2025

Guest

Harley Finkelstein

Harley Finkelstein, President of Shopify and entrepreneur extraordinaire, shares invaluable insights on building businesses in today's creator economy. He discusses why execution trumps ideas and the importance of persistence—most successful founders faced failures before achieving success. Harley emphasizes the reduced cost of failure and the need to tap into every platform where customers spend time. He encourages aspiring entrepreneurs to define their missions, seek mentorship, and truly understand their strengths for impactful growth.

01:27:00

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Episode notes

insights

INSIGHT

Gatekeepers Fell — Entrepreneurship Opened Up

Shopify removed historical gatekeepers, letting anyone launch a global business instantly.
That accessibility made entrepreneurship widely attainable and scalable for founders like Harley Finkelstein.

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ADVICE

Treat Failure As Cheap Experiments

Test many ideas because the cost of failure today is near zero; iterate until one works.
When something works, double down and scale the winning approach rapidly.

insights

INSIGHT

Grow The Pie, Don’t Fight For A Slice

Top founders expand total addressable market (TAM) instead of fighting for a fixed slice.
They adopt a growth mindset and create new demand rather than assuming a zero-sum pie.

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Harley's origin story and first Shopify store

03:54 • 2min

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How Shopify removed gatekeepers for founders

05:53 • 2min

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Control, visibility and the first sale moment

07:47 • 2min

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Patterns of successful founders: grit and failures

09:58 • 46sec

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TAM mindset: growing the market not the slice

10:44 • 3min

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Selling everywhere your customers are

13:51 • 2min

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Story, mission and founding narratives

16:02 • 3min

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Authenticity and sourcing early customer feedback

19:22 • 3min

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Audience-first product building

21:58 • 3min

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Partnering if you don't want to be front-facing

Hiring, mission and attracting talent

29:25 • 3min

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Finding your life's work and core strengths

32:11 • 2min

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Dairy Boy and the golden age of entrepreneurship

33:48 • 4min

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Longevity: refounding and reinventing brands

37:22 • 5min

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Scaling authentically without losing soul

42:04 • 3min

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Common pitfalls: glamorizing entrepreneurship

Lessons learned: focus your strengths

51:16 • 5min

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Mentorship and a personal board of directors

56:16 • 2min

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Protecting energy and main quests

Non-negotiables: meditation and rituals

01:08:13 • 5min

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Requalify for your role every year

01:13:04 • 4min

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Stand out at work: be too good to ignore

01:16:51 • 4min

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Work-life harmony and evolving seasons

01:20:55 • 4min

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Parenting, transparency and sharing the journey

01:24:37 • 1min

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Hope for the next generation of founders

01:26:02 • 3min

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Rapid-fire takeaways and final reflections

01:29:32 • 4min

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Closing gratitude and episode wrap

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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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