Harley Finkelstein — Tactics and Strategies from Shopify, the Future of Retail, and More (#486)
Illustration via 99designsI’m fascinated with how people find ambition, keep ambition, increase ambition, and unfortunately, as well, lose ambition.
— Harley Finkelstein
Harley Finkelstein (@harleyf) is an entrepreneur, lawyer, and the President of Shopify. He founded his first company at age 17 while a student at McGill. Harley is an advisor to Felicis Ventures, and he is one of the “dragons” on CBC’s Next Gen Den. In 2017, he received the Canadian Angel Investor of the Year award and Canada’s Top 40 Under 40 award, and in 2016 he was inducted into the Order of Ottawa. From 2014 to 2017 Harley was on the board of the C100, and from 2017 to 2020 he was on to the board of directors of the Canadian Broadcasting Corporation (CBC).
Please enjoy!
Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform.
Brought to you by LinkedIn Jobs recruitment platform with 700M+ users, LMNT electrolyte supplement, and ExpressVPN virtual private network service. More on all three below.
Listen onApple Podcasts[image error]Listen onSpotify
[image error]Listen onOvercast
#486: Harley Finkelstein — Tactics and Strategies from Shopify, The Future of Retail, and More
https://rss.art19.com/episodes/8616d415-ccf2-4a62-8551-b1309f089cdc.mp3Download
This episode is brought to you by LMNT! What is LMNT? It’s a delicious, sugar-free electrolyte drink-mix. I’ve stocked up on boxes and boxes of this and usually use it 1–2 times per day. LMNT is formulated to help anyone with their electrolyte needs and perfectly suited to folks following a keto, low-carb, or Paleo diet. If you are on a low-carb diet or fasting, electrolytes play a key role in relieving hunger, cramps, headaches, tiredness, and dizziness.
LMNT came up with a very special offer for you, my dear listeners. They’ve created Tim’s Club: Simply go to DrinkLMNT.com/Tim, select “Subscribe and Save,” and use promo code TIMSCLUB to get the 30-count box of LMNT for only $36. This will be valid for the lifetime of the subscription, and you can pause it anytime.
This episode is brought to you by LinkedIn Jobs. Whether you are looking to hire now for a critical role or thinking about needs that you may have in the future, LinkedIn Jobs can help. LinkedIn screens candidates for the hard and soft skills you’re looking for and puts your job in front of candidates looking for job opportunities that match what you have to offer.
Using LinkedIn’s active community of more than 722 million professionals worldwide, LinkedIn Jobs can help you find and hire the right person faster. When your business is ready to make that next hire, find the right person with LinkedIn Jobs. You can pay what you want and get $50 off your first job. Just visit LinkedIn.com/Tim.
This episode is brought to you by ExpressVPN. I’ve been using ExpressVPN to make sure that my data is secure and encrypted, without slowing my Internet speed. If you ever use public Wi-Fi at, say, a hotel or a coffee shop, where I often work and as many of my listeners do, you’re often sending data over an open network, meaning no encryption at all.
A great way to ensure that all of your data is encrypted and can’t be easily read by hackers is by using ExpressVPN. All you need to do is download the ExpressVPN app on your computer or smartphone and then use the Internet just as you normally would. You click one button in the ExpressVPN app to secure 100% of your network data. Use my link ExpressVPN.com/Tim today and get an extra three months free on a one-year package!
What was your favorite quote or lesson from this episode? Please let me know in the comments.
SCROLL BELOW FOR LINKS AND SHOW NOTES…
Want to hear an episode with Shopify’s founder and CEO? Check out my conversation with Tobi Lütke, in which we discuss feedback as a gift, fostering a growth mindset, the impact of dyslexia on Tobi’s reading list and coding endeavors, understanding “the next box,” why the business world should be keeping a close eye on the video game industry, Enneagrams, and much more.
#359: Tobi Lütke — From Snowboard Shop to Billion-Dollar Companyhttps://rss.art19.com/episodes/b4c1d67d-0bb9-47bf-b4a7-2324447e17bd.mp3Download
DISCLAIMER: I own stock in Shopify. I was not compensated in any way to have Shopify represented on the program or to talk about my reasons for investing in Shopify. I may financially benefit if Shopify’s stock goes up in value. I am not an investment adviser. All opinions are mine alone. There are risks involved in placing an investment in any company. None of the information presented today is intended to form the basis for any offer or recommendation, or have any regard to the investment objectives, financial situation or needs of any specific person.
SELECTED LINKS FROM THE EPISODE
Connect with Harley Finkelstein:
Connect with Shopify:
Shopify | Twitter | Instagram | Facebook | YouTube
Next Gen Den | CBCAllbirdsBombasGymsharkFashion NovaHigh Output Management by Andrew S. GroveThe Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben HorowitzAntifragile: Things That Gain from Disorder by Nassim Nicholas TalebThe Alchemist:A Fable About Following Your Dream by Paulo CoelhoThe 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Timothy FerrissWhat is Tall Poppy Syndrome? | The Tallest PoppyOttawa, ON | CanadaQuébec Referendum (1995) | The Canadian EncyclopediaMontréal. QC | CanadaQuebec Anglophones under Attack and Fear Worse Is Yet to Come from New CAQ Government | The Globe and MailMcGill UniversityThe Truth Behind the “Schmatta” Business | IrenebrinationAmerican ApparelParasucoWhat Is an Economic Moat? | InvestopediaDownton Abbey | Prime VideoUniversity of OttawaWhat Is the Socratic Method? | ThoughtCo.When Is an MBA Worth It? | InvestopediaSocrates in 90 Minutes by Paul StrathernWittgenstein in 90 Minutes by Paul StrathernPlato in 90 Minutes by Paul StrathernPlato in 90 Minutes by Paul StrathernDialectic | WikipediaThe Elements of Style by William Strunk Jr. and E.B. WhiteMoot Court | WikipediaOn Writing Well: The Classic Guide to Writing Nonfiction by William ZinsserHere’s What Stephen King Has to Say About The Elements Of Style | The Reading RoomDraft No. 4: On the Writing Process by John McPheeDune by Frank HerbertChief Operating Officer (COO) Definition | InvestopediaShopify Launches Build a Business Competition | ShopifyInvest OttawaBridgehead CoffeeTravelPod: 20 Years of Epic AdventuresMessenger KidsGetaroundFluidSurveys | CrunchbaseFellowSnowdevilRuby on RailsZapposThe Dark Knight | Prime VideoGoogle AdsHow to Become a Lawyer in Canada | LawyerEDU.orgWhat does Series-A, Series-B, Series-C Funding Mean in Startups? | Startup FreakBessemer’s Ten Laws for SaaS Companies | Velocity PartnersByWard MarketFelicis VenturesFirstMark CapitalRovioAngry BirdsRailsConf 2020Crossing the Chasm by Geoffrey MooreOne Waan | San FranciscoNike Inc.’s Unique Vision Statement and Its 11 Maxims | The Balance Small BusinessShopify, a Start-Up, Starts Its Own Business Competition | The New York TimesShopify Announces Build a Business Competition Winners | ShopifyMaker of iPad Cases Wins Shopify Competition (and $100,000) | The New York TimesDODOcase, Inc.Barack Obama iPad in DODOcase | HuffPostShopify Announces Winners of Inaugural Build a BIGGER Business Competition | Business WireIf You Invested $10,000 in Shopify’s IPO, This Is How Much Money You’d Have Now | The Motley FoolBarneys Is Sold for Scrap, Ending an Era | The New York TimesJ.CrewNick Kokonas on Resurrecting Restaurants, Skin in the Game, and Investing | The Tim Ferriss Show #429Chipotle Farmers Market | Chipotle Mexican GrillHeinz Sauces & CondimentsShopify Suspends Guidance for 2020 Amid Coronavirus Pandemic | The Motley FoolTrust Battery | SessionLabIntegral Coaching Method | Integral Coaching CanadaMossadThe Tim Ferriss Radio Hour: Meditation, Mindset, and Mastery | The Tim Ferriss Show #2019 Types of Meditation: Which One Is Right for You? | HealthlineInsight TimerTranscendental MeditationJack Kornfield — Finding Freedom, Love, and Joy in the Present | The Tim Ferriss Show #300Sharon Salzberg, World-Renowned Meditation Teacher | The Tim Ferriss Show #277StripeFUBUI Quit! | DiscoveryShark Tank | ABCPreventing Burnout: A Cautionary Tale by Charlie Hoehn | tim.blogThe Third Door: The Wild Quest to Uncover How the World’s Most Successful People Launched Their Careers by Alex BanayanShoe Dog: A Memoir by the Creator of Nike by Phil KnightOpen: An Autobiography by Andre AgassiFinite and Infinite Games by James Carse
SHOW NOTES
For anyone not in the know, what is Shopify, and how does Harley envision it scaling to become the entrepreneurship company? [06:50]What books have been most formative for Harley in his business journey with Shopify? What books has he gifted the most to other people? [09:37]How much has Shopify grown during the time in which I’ve known Harley? [14:00]How did Harley wind up moving from Montreal to South Florida and back to Montreal again, who is Phillip Rimer, and what part does he play in Harley’s story? [19:14]As someone who went to law school not to become a lawyer, but become a more effective entrepreneur, what were Harley’s most valuable takeaways from the experience? [28:37]How did Harley most effectively play along with the Socratic method in law school, and how did he bypass the need to absorb 1,200 pages of case study? [33:18]How would Harley design a curriculum that would convey the lessons he learned in law school without the need to actually go to law school, and which texts might I add to the list of required reading? [37:38]I give one must-read fiction recommendation to the guy who’s just now reading a work of fiction for the first time in his life. [43:07]What does Harley’s job at Shopify as COO actually entail, and how does annual re-qualification work there? [43:49]Who is Tobi Lütke, and how did he and Harley meet? [45:47]How did Harley get licensing agreements that made him competetive — as a nobody law student selling t-shirts — with monolithic companies like Walmart? [53:26]How did Harley become the proprietor of Shopify Store 136? [56:06]What were the early days of investment fundraising for Shopify like? [59:44]How I met Tobi and Harley, and the piece of advice I gave them that they took to heart. [1:06:33]On formulating the Build a Business competition that differentiated Shopify from the competition — even if the projected price tag seemed a bit steep at the time. [1:08:06]How the winner of year one’s Build a Business competition helped rejuvinate a dying industry and accessorize a US president, and how year two was designed to differentiate Shopify even further. [1:15:32]What impact have the multi-pronged surprises of 2020 had on retail, and what does Harley see for the future of the industry as a result — particularly ecommerce — that others might be missing? [1:17:55]My own observations about ecommerce adaptations during 2020. [1:26:47]Harley explains how Shopify is “arming the rebels,” and why ecommerce is poised to help support local communities, small businesses, and independent brands — especially during tough times. [1:29:46]How are coaches used at Shopify, what makes some coaches more effective than others in the context of the company culture, and what does it mean when Harley says leadership has to “requalify” for their jobs every year? [1:31:38]What does time with a coach at Shopify typically look like, how does Shopify’s post-coach era compare with its pre-coach era, and what does Shopify’s “trust battery” ultimately empower? [1:38:55]Naming coaching as “one of the top three or four things” that he’s done, what are some of those other things that have moved the needle for Harley? [1:42:46]After trying several “flavors” of meditation that didn’t really work for him, what variety does Harley find effective? [1:44:49]On the importance of blocking out time for family and loved ones (and sometimes just yourself) when an otherwise busy schedule might inadvertendly elbow them out of the picture. [1:47:22]What contemporary C-suite executives does Harley most admire as examples, and what is his unique approach to seeking out the most valuable advice from mentors? [1:50:10]Why you never want to “entice” a busy, potential mentor-level person with these words: “May I take you to coffee and pick your brain?” (And some advice for how you might get better results.) [1:54:56]Influential and thought-provoking biographies. [1:56:33]“Nice guys finish last” is not a truism, and other parting thoughts. [2:00:09]
PEOPLE MENTIONED
Andrew GroveBen HorowitzNassim Nicholas TalebTobi LütkePhilip RimerLindsay TaubWarren BuffettPeter ThielChris SaccaSocratesLudwig WittgensteinPlatoWilliam Strunk Jr.E.B. WhiteWilliam ZinsserJohn McPheePaulo CoelhoFrank HerbertMother GooseLuc LevesqueSam ZaidAydin MirzaeeFiona McKeanBatmanCody DeBackerDaniel WeinandJohn PhillipsAydin SenkutAmish JaniGeoffrey MooreLarry PageBarack ObamaSeth GodinGary VaynerchukRichard BransonTony RobbinsMarie ForleoDebbie SterlingTina EisenbergBen FrancisCody FauserCam GreggDeb ThompsonJack KornfieldSharon SalzbergDavid GandelmanSarah BlondinBob IgerPhil KnightPatrick CollisonJohn CollisonBen SilbermannChase JarvisDaymond JohnLL Cool JCharlie HoehnJ.R. MoehringerAndre Agassi
