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

Harley Finkelstein traces his path from founding a Montreal t-shirt business through law school in Ottawa to becoming COO of Shopify, framing the company as the world's first 'retail operating system' and aspiring 'entrepreneurship company.' He explains how law school's Socratic method sharpened his thinking and writing, how he met co-founder Tobi Lutke at an Ottawa coffee shop, and how the Build-A-Business competition (sparked by Tim's push to make the prize $100K) helped Shopify 'cross the chasm.' He argues the pandemic pulled the retail year 2030 into 2020, splitting retailers into 'resistant' and 'resilient' camps. Finkelstein also shares personal practices including meditation since 2014, internal coaching at Shopify, the 're-qualifying for your job' philosophy, and meticulous calendar scheduling.

• Shopify has over a million stores and, if it were a retailer, would be the second-largest online retailer in America after Amazon; market cap is above $100 billion.
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• In Q2 2020 Shopify merchants sold about $30 billion worth of products, with roughly 6,000 employees across 17 offices.
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• When Tim and Harley first met in mid-2010, Shopify had about a dozen employees and was about to raise a sub-$50 million Series A.
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• Tim pushed Shopify to raise the Build-A-Business prize from $10,000 to $100,000, money the company didn't actually have at the time.
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• E-commerce as a share of total US retail went from about 5% when Harley joined to 15% last year, then jumped toward 25% within three months of the pandemic.
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• Shopify uses a 're-qualifying for your job' philosophy where every leader must prove each year they are still the best choice for their role.
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• Shopify employs over a dozen full-time internal coaches on staff so any employee who wants or needs a coach can have one.
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• Harley has meditated every single morning since 2014 (10-15 minutes), after years of dismissing it while looking for a quick fix.
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• Harley says The Alchemist is the first work of fiction he has ever read in his life.
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• In Shopify's early days Harley gave away around 100 copies of Tim's The 4-Hour Workweek.
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• After a 1995 Quebec separation referendum created tension for Anglophones, Harley's family moved from Montreal to South Florida when he was 13.
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• McGill offered Harley near in-state tuition of about $1,800 a year because he was born in Montreal; his family lost their house and savings after the post-9/11 market crash.
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• Harley worked as a DJ from childhood, performing at roughly 300 bar mitzvahs.
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• Harley ran a 'licensing arbitrage' selling Dark Knight Batman t-shirts via Google AdWords in small Canadian cities that had a movie theater but no shopping mall.
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• Felicis investor Aydin Senkut won Shopify over by simply showing up unannounced at their Ottawa office above a restaurant during the Series A.
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• Senkut connected Shopify with Rovio, and the Angry Birds store launched on Shopify within about a week to prove the platform's scalability.
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• The first Build-A-Business competition drew 1,300 contestants; the winner, DODOcase, made iPad cases that Obama was photographed using.
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• Shoe Dog (Phil Knight) and Open (Andre Agassi) were both ghostwritten by J.R. Moehringer, a Pulitzer Prize winner Tim admires.
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