Aspire with Emma Grede

Episode: How to Win in the Golden Age of Entrepreneurship
Date: December 2, 2025
Guest: Harley Finkelstein (President, Shopify)
Host: Emma Grede

Episode Overview

Emma Grede sits down with Harley Finkelstein, President of Shopify, to explore what it really takes to build and sustain a business in what he calls “the golden age of entrepreneurship.” The conversation is wide-ranging—diving into Harley’s immigrant roots, the democratization of entrepreneurship, and, crucially, the hard-earned truths behind what separates dreamers from winners. With candid anecdotes, tactical advice, and memorable moments, this episode is a roadmap for founders, intrapreneurs, and anyone seeking meaning, resilience, and longevity in business and life.

Key Discussion Points & Insights

Harley’s Origin Story: From Immigrant Roots to Shopify (03:57–05:52)

• Entrepreneurial upbringing:
  “I am this child of a Hungarian immigrant who came to Canada from Hungary in 1956, had no money, and I was surrounded by entrepreneurs growing up, not because my father, my grandparents, wanted to be entrepreneurs, because most immigrants have no choice but to use entrepreneurship as the tool to put food on their table.” (Harley, 04:04)
• His first business: selling T-shirts to pay his way through law school, and the serendipitous meeting with Shopify’s founder Toby.
• The Shopify magic: The platform “allowed me to build this T-shirt company that ended up supporting myself, paying my tuition. I was paying my mother's rent...” (05:36)
• No limits: “There was no, like, ceiling on my success. No one was saying, well, you can only get this big or you can only sell in these geographies.” (04:52)

The Death of Gatekeepers & Cost of Failure (06:13–07:47)

• Historical barriers to entrepreneurship: needing capital and accepting gatekeepers (retail buyers, landlords).
• Modern advantage: “There’s no more gatekeepers. And because there’s no more gatekeepers, everyone can do it.” (Harley, 07:01)
• On risk: "For the first time in the history of entrepreneurship, the cost of failure is almost zero... If those businesses would have failed, entrepreneurs like you would have tried something else.” (Harley, 07:02)
• 50 years ago, failure could cost your home; now, the risk of trying is minimal.

Control, Visibility, and the Founder’s High (07:47–09:17)

• Founders now have direct relationships with their customers—data, feedback, control.
• The moment everything changes: “The second you get that first sale from someone you don't know... That Cha Ching sound, your life changes, all of a sudden, your identity changes.” (Harley, 08:46)

The Patterns of Entrepreneurial Success (10:43–15:39)

• Most successes are built on failure:
  “Most successful entrepreneurs that you see out there unequivocally have a past littered with failure, but it doesn't really matter to them, right? Because they have this grit which allows them to persevere through it.” (Harley, 11:25)
• Resilience is key:
  “If you start to think that the thing that happened is you, that there’s something wrong with you... you will never be.” (Emma, 11:48)
• Expand the pie:
  “The best entrepreneurs have this positive sum understanding, and they believe they can actually grow the market itself.” (Harley, 13:32)
• Omnichannel is everything in 2025:
  “They don’t talk like that. They sell on every surface area where their consumer is spending time... every single place where consumers are spending their time is a channel.” (Harley, 14:39)

Winning Tactics for Building Businesses (17:20–24:36)

1. Origin Story & Mission

• “You have to have a great story... what you do is you carry the consumer along on your journey and you turn consumers into almost these, like, force multipliers for a story.” (Harley, 19:16)

2. Authenticity & Early Community

• “People are willing to give you their time and their energy just because they want to kind of support you... it’s this beautifully optimistic journey of starting a business.” (Harley, 21:44)
• Leverage communities (e.g., Facebook groups) to validate and refine ideas.

3. Audience First, Product Second

• “First you start with an audience, and then you build a product around the audience... Everyone has an audience.” (Harley, 22:46)
• Example: Kylie Jenner built Kylie Cosmetics by authentically engaging her audience through makeup tutorials before creating her own products.

4. Founder-Led Storytelling

• “Founders always have a story. It's their story. They get unequivocally to tell the story about what they did and why they did it.” (Harley, 20:09)

5. Assembling Complementary Teams

• “The best entrepreneurs I know are not well rounded. We're all kind of like spiky. We're really good at something and we're really bad at other things... Assemble ‘the Avengers’—find your counterpart.” (Harley, 26:07)

Longevity & Reinvention in Business (37:00–41:43)

• Brands endure through reinvention:
  “Iconic brands have these re-founding events and it’s always because someone within the company says we don’t have to do things the way it’s always been done.” (Harley, 39:43)
• Examples: Mattel’s Barbie, Birkenstocks, and Hunter Douglas’ ongoing innovations.

Scaling Authentically (41:43–44:09)

• Scale without losing soul:
  “Scale is really hard because often when you think of scale, you think about losing the soul... There is this way to scale that stays authentic, but brands that try to be everything to everyone, that's usually death to a brand.” (Harley, 44:09)
• Example: AG1 (now scaling thoughtfully from a single SKU), Gymshark (from D2C to experiential retail).

The Unvarnished Truths of Entrepreneurship (44:25–47:21)

• Most businesses fail:
  “Most businesses fail. That means you have to expect for everything not to turn out.” (Emma, 44:38)
• Don’t glamorize the highlight reel: “The more successful you are, the more failures you have under your belt.” (Harley, 46:34)
• Grit above all:
  “Where entrepreneurs fail is they give up way too early... The ones that succeed have this unwavering grit where they can just keep going.” (Harley, 46:45)

Finding Life’s Work & Personal Meaning (29:35–33:21; 68:14–76:05)

• Discovering your ‘why’:
  “Whatever you did between the ages of 13 and 16 for fun is probably something you should consider doing when you're older.” (Harley via Bill Gates, 31:16)
• Ask your tribe: “Sometimes we get in our own way. Ask your friends and your family what they think you should do.” (Harley, 32:31)
• Rituals and non-negotiables: Harley practices meditation, family Shabbat, and regular dinners with friends—crucial for grounding amidst entrepreneurial chaos (+ wellness tips at 68:14–70:27).
• Antifragility:
  “Some things, when you drop, it actually reassembles stronger... I think this idea of antifragility is really important for entrepreneurs.” (Harley referencing Antifragile, 92:28)

The Practice of Requalifying (71:24–80:45)

• Annual self-renewal:
  “If you are leading a company of any size, you must requalify for your job every year.” (Harley, 71:39)
• Not just at work: “I have to requalify to be Lindsay’s husband every year and I have to requalify to be Bailey and Zoe’s dad every year.” (Harley, 71:47)
• For teams and staff:
  “Be too good to ignore... If you’re in an organization and you want to accelerate your career, just be too good to ignore.” (Harley, 76:46)

Work-Life Balance & Parenting as an Entrepreneur (80:53–85:52)

• Work-life “harmony” beats balance:
  “I think this idea of work life balance is a little bit of a misnomer. I think what we're all searching for is some sort of harmony...” (Harley, 81:41)
• Parenting with honesty:
  “I want my kids to know that, first of all, I'm successful. They are not. They have to prove themselves as well...” (Harley, 83:12)
• Show the journey, not just the destination:
  “I want them to see the work, the actual journey, and the destination. And I think a lot of successful people only show the destination, and they don’t necessarily leave enough breadcrumbs for their kids.” (Harley, 85:37)

The Golden Age of Entrepreneurship (35:41–36:33; 85:52–89:21)

• “Right now is unequivocally the golden age of entrepreneurship... it is the best time in the history of the world to start a business.” (Harley, 35:15)
• The future is insurgent:
  “Companies that didn’t exist two years ago are now incumbents... Incumbents used to be impossible to disrupt—now, consumers prefer the insurgents, prefer the startups.” (Harley, 88:04)
• “Impossible to compete with a deeply convicted... founder that has so much conviction.” (Harley, 88:40)

Notable Quotes & Memorable Moments

• “The second you get that first sale from someone you don't know... that Cha Ching sound, your life changes.”
  — Harley, 08:46

• “You get a little bit addicted.”
  — Emma, 08:56

• “Most successful entrepreneurs that you see out there unequivocally have a past littered with failure, but it doesn't really matter to them, right? Because they have this grit which allows them to persevere through it.”
  — Harley, 11:25

• “If you have ambition, if you have ideas in the shower, you are an entrepreneur.”
  — Harley, 87:21

• “How you do anything is how you do everything.”
  — Harley/Family Motto, 84:59

• “Be too good to ignore.”
  — Harley, 76:46

• “I have zero cringe factor... turning the camera around and filming a little video of yourself... if you can get over the cringe factor of it, you can build a billion.”
  — Harley, 24:36

• “Right now is unequivocally the golden age of entrepreneurship.”
  — Harley, 35:15

Important Timestamps

• Harley’s upbringing and Shopify origin: 04:04–05:52
• How entrepreneurship barriers disappeared: 06:13–07:47
• Making the first online sale: 08:46
• Patterns of success / grit and failure: 10:43–15:39
• Storytelling and cultivating audience: 17:20–24:36
• The importance of finding your ‘thing’ and mentorship: 51:42–55:55
• Annual requalification / self-improvement: 71:24–76:05
• Work-life harmony and rituals: 68:14–70:27
• Antifragility concept: 92:28
• Rapid Fire Round: 90:34–93:57

Actionable Takeaways

• Embrace failure and grit: The most successful founders see setbacks as stepping stones—not personal shortcomings.
• Start with the audience, not the product: Cultivate a community before you try to sell.
• Tell your story—authentically: Mission and narrative differentiate you in a crowded market.
• Expand the market, don’t just capture share: Growth mindset and positive sum thinking lead to category creation.
• Scale thoughtfully: Grow in ways authentic to your brand and customers.
• Continually requalify: Treat your roles—at work, at home—as ongoing commitments to improvement.
• Prioritize energy and rituals: Identify what gives meaning and focus; be intentional about maintaining it.

Closing Sentiment

“If you have ambition, if you have ideas in the shower, you are an entrepreneur... My hope is that in the future, more people try their hand in entrepreneurship. Not because they want to make a lot of money, but because I think it's the easiest way or the best way to find your life's work.” (Harley, 87:19; 89:21)

This episode is a masterclass in mindset, resilience, intentionality, and tactical advice—whether you’re just starting out or scaling up, these are lessons for every builder and dreamer in the golden age of entrepreneurship.