Harley Finkelstein — Strategies from Shopify, the Future of Retail, and More | The Tim Ferriss Show

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A fiction book by Frank Herbert recommended to Harley by Tim Ferriss as a leadership book.

A new show launched on Discovery by Shopify Studios, mandated to create inspiring and authentic content about entrepreneurship without promoting Shopify directly.

A reality television series where entrepreneurs pitch their business ideas to a panel of investors. Harley consulted Daymond John about his experience on it.

A Canadian business reality television series, similar to Shark Tank, on which Harley Finkelstein is one of the 'dragons' (investors).

A popular game by Rovio that became a major hit, whose plush toys were sold on Shopify, demonstrating the platform's scalability.

A sugar-free electrolyte drink mix that Tim Ferriss uses 1-2 times daily, especially helpful for those on keto, low-carb, or paleo diets, and in cold weather for hydration.

The company that Andy Grove built, known for high output management principles.

A direct-to-consumer shoe brand that is channel agnostic, caring only that customers buy their shoes regardless of whether it's online or offline.

Mentioned as the largest online retailer in America, with Shopify being the second-largest in terms of merchant sales if viewed as a single entity. The host also mentions an experience during the pandemic where Amazon prioritized essential goods, leading to long lead times for non-essential items like coffee filters.

A virtual private network (VPN) app recommended by Tim Ferriss's Twitter followers for securing internet connections, hiding IP addresses, and bypassing regional content restrictions.

An American hip-hop apparel company founded by Daymond John.

A venture capital firm that Harley Finkelstein advises.

The Finnish company behind the 'Angry Birds' game. Aydin Senkut connected them with Shopify to launch their online store and test Shopify's scalability.

A successful direct-to-consumer brand that started through the 'Build a Business' competition and grew to a billion-dollar valuation. They quickly pivoted during the pandemic by rebranding to 'Home Shark' when gyms closed.

A large technology company where Cody Fauser's coach had previously run a significant engineering team.

A social media platform, whose CEO Ben Silbermann is admired by Harley Finkelstein.

A studio created by Shopify with the mission to produce inspiring content about entrepreneurship, such as the 'I Quit' show on Discovery.

Described by Harley Finkelstein as the world's first retail operating system, enabling anyone to sell products online or offline, with a vision to be the entrepreneurship company. It hosts over a million stores and has a market cap of over $100 billion.

A venture capital firm that published a white paper called 'The 10 Laws of SaaS Businesses,' which Shopify used for its nomenclature and formulas, and which eventually led them to lead Shopify's Series A round.

A restaurant chain that has launched an online store on Shopify to connect consumers with their farmer suppliers, creating a 'Chipotle farmer's market'.

A financial services and software as a service company, whose founders Patrick and John Collison are admired by Harley Finkelstein for their drive to build an incredible company.

Canada's national public broadcaster, Harley Finkelstein was on its board of directors from 2017 to 2020.

A New York-based venture capital firm that joined Shopify's Series A round.

Cited as an example of a company that created a marketing 'hack' by convincing the world that anyone with a body could be an athlete, thereby expanding their market.

Winner of the first 'Build a Business' competition in 2010, known for making iPad cases and rejuvenating the bookbinding industry in San Francisco.

An award Harley Finkelstein was inducted into in 2016.

The television channel where Shopify Studios launched their show 'I Quit', focusing on entrepreneurship.

LMNT is mentioned as the executive hydration partner of Team USA Weightlifting, indicating its use by elite athletes.

A prestigious newspaper that covered Shopify's 'Build A Business' competition, providing significant attention and credibility to the startup.

A non-profit organization that Harley Finkelstein was on the board of from 2014 to 2017.

Designer, entrepreneur, and founder of CreativeMornings and Tattly, who served as a mentor for the 'Build a Business' competition winners.

Co-founder of Nike and author of 'Shoe Dog', who Harley Finkelstein deeply admires for his ambition and candid storytelling.

Co-founder and President of Stripe, admired by Harley Finkelstein.

Photographer, director, and entrepreneur, a mutual friend of Tim Ferriss and Harley Finkelstein, who Harley learns something new from every time they talk.

Founder of FUBU and an investor on Shark Tank, a mutual friend of Tim Ferriss and Harley Finkelstein, who shares valuable anecdotes about entrepreneurship.

A Pulitzer Prize-winning author, the 'collaborator' (writer) behind Phil Knight's 'Shoe Dog' and Andre Agassi's 'Open'. Highly praised by Tim Ferriss for his writing talent.

Entrepreneur, author, and coach who served as a mentor for the 'Build a Business' competition winners.

Author of 'Finite and Infinite Games,' a book that explores the philosophical implications of these two types of games, relevant to business strategy.

Entrepreneur, lawyer, and Chief Operating Officer (COO) of Shopify, guest on the podcast, known for his role in scaling Shopify.

Author of 'The Alchemist,' whose book was initially a commercial failure but later became a global bestseller.

Author of the influential science fiction novel 'Dune'.

Co-author of 'The Elements of Style,' a foundational text on writing discussed by Harley.

Author of 'On Writing Well', a classic book on writing that focuses on clarity and conciseness, recommended by Tim Ferriss.

Author of 'Draft No. 4', a book about the writing process, specifically structuring, recommended by Tim Ferriss.

Author of 'Crossing the Chasm', a book about technology adoption lifecycle.

Author and marketing expert who served as a mentor for the 'Build a Business' competition winners.

Life and business strategist who served as a mentor for the 'Build a Business' competition winners.

A meditation teacher whose guided meditations Harley Finkelstein listens to on Insight Timer.

Former CEO of Disney, whom Harley Finkelstein admires as a leader.

Co-founder and CEO of Stripe, admired by Harley Finkelstein.

An individual praised by Tim Ferriss for doing 'free work' for people to gain opportunities, who wrote about his experience with Tim and 'The 4-Hour Body' launch.

Billionaire venture capitalist who, like Peter Thiel, has a law degree but opted not to practice law.

A well-known Silicon Valley investor who impressed Shopify by showing up at their office in Ottawa during their Series A fundraise. He later connected Shopify with Rovio (Angry Birds) to launch their online store and test Shopify's scalability.

Former US President, who was photographed using a DODOcase iPad case, adding to the brand's prominence.

Founder of the Virgin Group, who offered his private island, Necker Island, as a prize for 'Build a Business' competition winners.

Founder and CEO of GoldieBlox, who served as a mentor for the 'Build a Business' competition winners.

Shopify's original CTO and one of the first employees, who pioneered the idea of internal coaching at the company.

A meditation teacher whose guided meditations Harley Finkelstein listens to on Insight Timer.

A meditation teacher whose guided meditations Harley Finkelstein listens to on Insight Timer.

Co-founder and CEO of Pinterest, admired by Harley for doing an amazing job with his company.

The author of 'High Output Management' and former CEO of Intel, admired for his practical approach to business.

Author of 'The Hard Thing About Hard Things', whose work is seen as a modern take on high output management.

Author of 'Anti-Fragile', a book about systems that gain from disorder, recommended by Harley.

Successful entrepreneur and venture capitalist with a law degree who did not actively practice law, known for his debate training.

Co-author of 'The Elements of Style', praised for its conciseness and clear exposition of writing principles.

Author known for his review of 'The Elements of Style', praising its lack of 'bullsh*t' and emphasizing its rule to 'omit needless words'.

Co-founder and CEO of Shopify, an immigrant from Germany who built the software to sell snowboards and then made it available to others, known for being a software product genius.

Shopify's original angel investor, who is still on their board, and whom Harley had to convince to join the company.

Entrepreneur, author, speaker, and internet personality who served as a mentor for the 'Build a Business' competition winners.

Former professional tennis player and subject of the autobiography 'Open'.

A meditation app that Harley Finkelstein uses for guided meditations and white noise, helping him maintain consistency in his practice.

A platform for small businesses to find qualified candidates for open roles quickly, with features like targeted screening questions and mobile management.

A book by Tim Ferriss, mentioned in the context of Charlie Hoehn's experience working on its launch.

A book by James Carse, recommended by Tim Ferriss as a meditation on long-term perspective and engagement, aligning with Harley's view on relationship building.

An Andy Grove book that Harley found incredibly valuable for cutting through business jargon and providing practical guidance for running a company.

A book recommended by Tim Ferriss for its funny stories and effective advice on taking less conventional paths to make connections.

The autobiography of Andre Agassi, co-written by J.R. Moehringer, which deeply impressed Tim Ferriss.

Ben Horowitz's book, seen by Harley as a modern iteration of 'High Output Management', offering valuable insights into entrepreneurship.

Nassim Nicholas Taleb's book, which Harley reread during the pandemic, finding it valuable for understanding how systems and individuals can get stronger as they break or face challenges.

A fiction book by Paulo Coelho that Harley is reading for the first time, noting it's a different, more enjoyable reading experience than his usual non-fiction.

A book by William Zinsser, recommended by Tim Ferriss as incredibly helpful for removing ambiguity and 'puffery' from writing.

John McPhee's book on the writing process, recommended for nerds interested in structuring written pieces.

A book by Geoffrey Moore, referenced by Harley to explain how the Build a Business competition helped Shopify move beyond early adopters to the mainstream.

Tim Ferriss's book, which Harley gave away many copies of in the early days of Shopify, as it popularized the idea of side hustles and system-building for entrepreneurs.

A short, classic writing guide by Strunk and White, which Harley believes teaches everything he learned about writing in law school.

Phil Knight's autobiography, highly recommended by Harley for its candid and humble storytelling about ambition and the difficult journey of building Nike.

A well-known brand that went direct-to-consumer during the pandemic through Shopify, despite historical resistance to selling online.

A chocolate brand that went direct-to-consumer via Shopify during the pandemic.

A chocolate brand that went direct-to-consumer via Shopify during the pandemic.

A white paper by Bessemer Venture Partners that provided the nomenclature, calculations, and formulas Shopify used to understand and run its business, including metrics like monthly recurring revenue and customer lifetime value.

An award received by Harley Finkelstein in 2017.

A contemporary coding language used by Tobi Lütke to build Shopify, gaining early traction from its developer community.

A hybrid coaching style used by Shopify's internal coaches, focusing on personal development through metaphors and accountability.

Richard Branson's private island in the British Virgin Islands, offered as a prize for winners of the 'Build a Business' competition.