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How To Start A Business For The Price Of A Rhode Lip Case! Shopify President

Mar 25, 2026

Guest

Harley Finkelstein

Harley Finkelstein, Shopify president and longtime entrepreneur who scales merchants worldwide, shares the playbook behind hits like Skims and Kylie Cosmetics. He unpacks how creator-led and celebrity brands win, why AI amplifies entrepreneurs, and clever attention hacks like the “3,872 books” move. Short, tactical stories on starting cheap, finding your ikigai, and building brands that stick.

01:16:55

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ADVICE

Build What Solves Your Own Problem

Solve a problem you personally encounter as your best route to product-market fit.
Harley points to founders like Ben Francis (Gymshark) and Trina (Figs) who built solutions to their own pain points.

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ADVICE

Get Attention By Offering What They Actually Want

To get someone's attention, figure out what they care about and offer it directly in a concise hook.
Harley suggests using a memorable line from their recent speech or an explicit need (e.g., buy X books) in the subject line.

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ANECDOTE

The 3,872 Books Email That Got Gary Vee's Attention

Harley grabbed Gary Vaynerchuk's attention with a one-line subject that offered exactly what Gary needed: buy the remaining books to hit bestseller.
Subject line: I want to buy 3,872 books, which got Gary to respond and mentor Shopify's contest.

Get the Snipd Podcast app to discover more snips from this episode

Defining Entrepreneurship and Shopify's Scale

02:41 • 4min

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Should Everyone Try Entrepreneurship?

06:16 • 3min

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Barriers That Stop People From Starting

08:52 • 2min

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Proximity, Mentors, and Finding Your Idea

10:23 • 3min

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Sustaining Passion: Making Work Your Life's Work

13:50 • 4min

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Impact: Changing Women's Lives Through Access

17:33 • 7min

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How to Get Anyone's Attention

Creator Peaks and Reinvention

29:55 • 2min

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Do You Need An Audience? The 1,000 True Fans

31:34 • 3min

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Why Creator-Led Brands Win

34:59 • 5min

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Celebrity Brands: Authenticity Determines Success

40:14 • 4min

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Why Entrepreneurs Should Embrace AI

44:31 • 4min

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Agentic Shopping: The New Personal Shopper

48:37 • 3min

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AI Won't Replace Creators—It Creates Channels

Raising Entrepreneurial Kids

56:09 • 4min

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Rapid Fire: Personal Habits and Purchases

01:00:22 • 2min

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Brands He Admires and Book Recommendations

01:01:57 • 2min

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What Makes Great Brands: Care and Thoughtfulness

01:04:05 • 4min

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Embracing Your 'Spiky' Strength

01:08:21 • 56sec

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Becoming a Better Storyteller: Watch Your Tapes

01:09:17 • 5min

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Where to Find Harley and Big Shot

• Mentioned in 498 episodes

Rich Dad Poor Dad

What the Rich Teach Their Kids about Money - That the Poor and the Middle Class Do Not

C.P.A. Sharon L. Lechter

Robert Kiyosaki

The book tells the story of Robert Kiyosaki's two fathers: his 'poor dad,' a highly educated but fiscally poor man, and his 'rich dad,' the father of his best friend who was a successful entrepreneur. It emphasizes the importance of financial education, distinguishing between assets and liabilities, and building wealth through investing in assets such as real estate and businesses. Kiyosaki argues that a good education and a secure job are not guarantees for financial success and provides practical lessons on how to make money work for you rather than working for money.

#188

• Mentioned in 118 episodes

Crush it!

why now is the time to cash in on your passion

Gary Vaynerchuk

In 'Crush It!', Gary Vaynerchuk shows readers how to harness the power of the Internet to make their entrepreneurial dreams come true. The book focuses on utilizing new, free tools on the Internet to capitalize on branding and developing a business. Gary shares his own experiences, from building his family's wine shop into a national industry leader to transforming his life and earning potential by building his personal brand. The book emphasizes the importance of identifying and pursuing your passions, using social media effectively, and maintaining a hardworking and authentic approach to business.

#161

• Mentioned in 133 episodes

Antifragile

Things That Gain from Disorder

Nassim Nicholas Taleb

Albino Santos Mosquera

Genís Sánchez Barberán

In 'Antifragile', Nassim Nicholas Taleb delves into the concept of antifragility, arguing that some systems not only withstand stress and disorder but actually benefit from them. The book builds on ideas from his previous works, such as 'Fooled by Randomness' and 'The Black Swan', and is part of his five-volume philosophical treatise on uncertainty, 'Incerto'. Taleb provides examples from various fields, including science, economics, and history, to illustrate how antifragility can be achieved and how it contrasts with fragility and robustness. He also discusses strategies like the barbell strategy and optionality, and critiques modern society's attempts to eliminate volatility, which he believes are harmful. The book is praised for its revolutionary ideas and multidisciplinary approach, though it has also received criticism for its style and some of the author's views on mental health and other topics.

#90

• Mentioned in 187 episodes

The hard thing about hard things

building a business when there are no easy answers

Ben Horowitz

In this book, Ben Horowitz shares his personal and often humbling experiences in the tech industry to offer essential advice and practical wisdom. He addresses various hard decisions and challenges that business leaders face, such as firing friends, managing company culture, handling layoffs, and making tough strategic decisions. Horowitz emphasizes the importance of honesty, resilience, and adaptability in leadership, drawing from his experiences with companies like Loudcloud and Andreessen Horowitz.

#216

• Mentioned in 107 episodes

High Output Management

Andrew S. Grove

High Output Management is a seminal book by Andrew S. Grove that outlines his management and productivity concepts developed during his tenure at Intel. The book introduces the 'management by objectives' approach, also known as the objectives and key results (OKR) framework. It covers techniques for creating highly productive teams, methods of motivation, and the importance of measurable processes, performance reviews, and training. Grove emphasizes the role of managers in leading and motivating teams, and his book is praised for its practical advice and timeless relevance in various professions and industries.

Why is Hailey Bieber’s Rhode a $1B empire while other celebrity brands feel like "cash grabs"?

Shopify President, Harley Finkelstein, breaks down the elite playbook behind Rhode, Skims, Kylie Cosmetics, Gymshark, and Chamberlain Coffee. From the “9 Person Rule” (why your friends are keeping you broke) to the “3,872 Books” email hack that caught Gary Vee’s attention, Harley explains how the world's most successful founders actually think!

No more waiting for a sign, a mentor, or 'perfect' timing. The cost of entry is $39 and a 'stupid' idea that you’re finally brave enough to start. The golden age of entrepreneurship is here - don't let it happen without you!

Timestamps:

00:00:00 Intro
00:02:18 Why You Don’t See Yourself As An Entrepreneur
00:05:17 Should Everyone Try Entrepreneurship?
00:07:53 Why Most People Never Start
00:09:07 The One Thing That Creates Billion Dollar Businesses
00:12:50 Motivation Doesn’t Last… This Does
00:13:56 Finding Your Ikigai (Life’s Work)
00:16:32 “You’re Changing Women’s Lives”
00:18:18 Chasing People You Admire
00:22:31 Fiverr Ad
00:23:42 How To Get Anyone’s Attention
00:27:42 Do Creators Have A Peak?
00:30:26 Do You Need An Audience To Win?
00:33:59 Why Kardashian Brands Actually Work
00:39:36 Will Celebrity Brands Keep Winning?
00:43:08 Should We Be Scared Of AI?
00:47:31 What Is AI Shopping?
00:49:48 Will AI Replace Influencers?
00:50:59 Will AI Replace Everything?
00:53:07 Shopify Ad
00:54:04 Bilt Ad
00:55:13 A Letter From Harley’s Daughters
00:55:51 Raising Future Entrepreneurs
00:58:53 What He Spends His Money On
01:00:06 Skiing vs Building Businesses
01:00:19 Best Books For Entrepreneurs
01:01:46 Industries To Avoid
01:02:25 The Most Innovative Product He’s Seen
01:03:30 What Makes A Brand Truly Great
01:06:53 His “Spiky” Career Strategy
01:07:45 The One Belief That Changed Everything
01:10:22 How To Become A Better Storyteller
01:12:32 Where To Find Harley

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Sponsors:

Fiverr - If you are scaling a business, then you need to visit https://pro.fiverr.com

Shopify - http://Shopify.com/HSR

Bilt - http://joinbilt.com/hsr

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Follow Harley Finkelstein:

Instagram: www.instagram.com/harley

Shopify: https://www.shopify.com/

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