Harley Finkelstein
President, Shopify. On 4 shows, 7 appearances, plus 1 compilation re-air not counted. The Shows tab opens the full record on each.
executiveinvestorfounderhost@harleyf ↗LinkedIn ↗harleyf.com ↗Wikipedia ↗
Harley Finkelstein is the President and former Chief Operating Officer of Shopify, having joined in 2010 to help scale the e-commerce platform into a public company. He is also an active angel investor, co-founder of Firebelly Tea, and host of the Big Shot podcast.
4shows
7appearances
83statements
19resolved
13supported
1contradicted
68%fully supported
56said about them ↓ Everything Harley Finkelstein said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Finkelstein: Shopify expects employees to test AI before hiring additional headcount
“The expectation is before you go and try to hire another person for your team, you ask yourself and you test whether or not some sort of AI tool can actually do it better for you. And if it can, that's what you should be doing.”
Finkelstein: AI will allow businesses to reach $100M GMV within three years
“I think you're going to have another step function. Like, I think that you will have this incredible hockey stick curve of businesses that grow from zero to a hundred million dollars in GMB inside of three years, instead of, inside of, like, 10 years.”
Harley Finkelstein: The future of retail is omnicommerce, not online vs offline
“But around 2013, 2014, it became increasingly clear to us that the future of retail is not binary. It's not online versus offline. Despite what you may hear from the CEOs of major malls and major retailers, the best spies and the, excuse me, the JCPenney's of …”
Harley Finkelstein: The internet has commoditized retail distribution
“Because distribution is no longer, it's commoditized now, and the internet did that.”
Finkelstein: Shopify leaders must re-qualify for their roles every year
“On our team that whatever, whatever the thing you're responsible for, you are going to try to be the very, very best in the world at that particular thing. Product design, sales, storytelling, finance, legal, whatever that might be. That's the commitment. And …”
Finkelstein: Founder-led companies are superior to professionally managed ones
“It's actually the reason why net net, I always prefer founder led companies that professionally managed companies. I think founder led companies are more interesting.”
Finkelstein: Every Shopify employee should be able to keynote on doing their job differently
“Every person that works at Shopify should be able to go to their Industry conference, whatever their category, whatever area they're in business, and they should give the keynote about how they're doing their job, completely different than everybody in the cro…”
Finkelstein: Solo AI merchants outperform The Gap's 1990s 300-person retail team
“A one person operation at their mom's kitchen table right now on Shopify, who needs to write a product description, who needs to do product photography. I suspect that today they can have a higher converting, a higher, a highly optimized or higher optimized. P…”
Finkelstein: Abandoning AI over occasional hallucinations will cause professionals to fall behind
“I think one of the things that you have to have if you're going to be successful in this new era of business and actually in any era with all this new technology is you have to be a techno optimist. You have to believe that things are getting so good at such a…”
Finkelstein: Tobi Lütke is the greatest product mind on Earth
“I mean, Toby, I think is probably the greatest product mind on the planet.”
Harley Finkelstein: Toronto is less entrepreneurial than Montreal
“Toronto, for example, is I think less entrepreneurial. It's the biggest city in Canada. It's far more, you know, there's like, there's the wall street of Canada called Bay street in Toronto.”
Finkelstein: Shopify GMV ranks second behind Amazon in US online retail
“If you pretend we were retailer, we would be the second largest online retailer in America after Amazon.”
Finkelstein: Gymshark is probably one of Nike's biggest rivals
“I think Gymshark is probably one of the biggest rivals of Nike.”
Finkelstein: Web3 is producing more entrepreneurs than ever before
“And that's, I think more entrepreneurs is a good thing, and I think Web Three is actually producing more entrepreneurs than ever before.”
Finkelstein: Omnichannel retail will become obsolete terminology just like color TV
“Talking about Omni channel in the future will be like talking about a color TV today. You never would say color TV. I think every business will be by its very nature on each other, even restaurants.”
Finkelstein says law school is a finishing school for entrepreneurs
“In fact, when people ask me if they should go to law school, like as an entrepreneur, I often say the law school can be, if you get out of it, you know, it can be The like finishing school to be an entrepreneur.”
Finkelstein: Law school acts as finishing school for entrepreneurs
“In many ways, I think law school was a little bit like finishing school or etiquette school for entrepreneurs. I teach you how to write really well, which of course is really important when you're running a company. It teaches you how to be articulate and teac…”
Finkelstein: Modern tech companies are geographically agnostic
“I think business today, in particular technology companies, are geographically agnostic. I don't think it matters where you're based.”
Finkelstein calls Tobi Lütke the greatest product person he has met
“He is the greatest product person I've ever met in my life. He's this incredible tech visionary, especially when it comes to commerce.”
Finkelstein: Mutual accountability partnerships are how $100B companies are built
“Most people need someone else to help them pull up to the next level, and if you find someone like that, and you sort of Mutually commit to one another. I mean, that's real partnership that makes for, that's how you build a hundred billion dollar company, I th…”
Finkelstein: Founders should partner with peers across distinct, non-overlapping domains
“My advice would be, if you're in, like, drama club, go find someone, like, in the AV club, and then go find someone in, like, the computer, like, the coding club, and go find someone, like, who's painting. And those should be your co-founders, because each of …”
Finkelstein: Companies Should Skill-Match Leaders to World-Class Strengths Rather Than Tenure
“I really think that most companies end up looking at a buffet of their leaders and looking at the slots that are available and just go like, go here, go there. And I think it takes a very thoughtful and very often a founder CEO or founder leader like Toby, som…”
Harley Finkelstein: Lulu Cheng Meservey is a world-class comms genius
“Lulu is on our board. It was amazing. Probably one of the greatest comms geniuses on the planet talks about this go direct.”
The other half of the tape: Harley Finkelstein's own voice is left out of every number here. Other people bring the name up 54 times in 26 episodes across the shows. 2 statements on the record name them. every mention, with the transcript →
Who brings them up most Harry Stebbings 17Alex Lieberman 12Jean-Michel Lemieux 5Sahil Bloom 4David Segal 4Shane Parrish 2Miles Grimshaw 2Andrew Wilkinson 2
Statements about Harley Finkelstein, by other people (2)
Harley Finkelstein advocates that Shopify employees annually evaluate if they requalified
“It reminds me of what Harley Finkelstein has said at Shopify, which is the idea that every year, every employee should think about, did they re-qualify for their job at the company?”
Every mention by year
tap a year for its mentions
20VC 28
Founder's Journal 12
the Knowledge Project 9
the Startup Ideas Podcast 5
2026 2 mentions in 2 episodes 1 per episode
2025 3 mentions in 2 episodes 2 per episode
2024 23 mentions in 8 episodes 3 per episode
- Jean-Michel Lemieux: Three Product Decisions Every Team Needs to Make | E1129 · 20VC with Harry Stebbings
- David Segal: Building a $200m Business
- Andrew Bialecki: Is Klaviyo the Most Under-Priced Public Company? | E1170 · 20VC with Harry Stebbings
- The Great Online Game
- Kaz Nejatian: How Shopify Built a $90BN Business to Last 100 Years | E1189 · 20VC with Harry Stebbings
- Dax Dasilva: $900M ARR at $2.6BN Market Cap?! Lightspeed, The Most Undervalued Public Company |E1188 · 20VC with Harry Stebbings
- Amp it Up
- Erik Allebest: Scaling to $100M Revenue, 150M Members and 700 People, All with No Vc Funding | E1113 · 20VC with Harry Stebbings
- every mention in 2024, scene by scene →
2023 8 mentions in 5 episodes 2 per episode
- Tooey Courtemanche: From Construction Worker to Billionaire CEO | E1090 · 20VC with Harry Stebbings
- Why The Future of the Creator Economy is Bright
- Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061 · 20VC with Harry Stebbings
- My Biggest WINS & REGRETS Of 2023
- Glen Coates: Why Shopify Will Dominate Amazon; How Microsoft Made Smartest Move of 2023 | E986 · 20VC with Harry Stebbings
- every mention in 2023, scene by scene →
2022 9 mentions in 6 episodes 2 per episode
- Andrew Wilkinson: Tiny Holdings
- How to Build a Brand of the Future
- How to Leverage Nostalgia and Win at Marketing with Danny Trinh
- Michael Mignano: How I Founded Anchor; Why TikTok could be a $2 TRILLION Company | 20VC #923 · 20VC with Harry Stebbings
- Aydin Senkut: How I Scaled from a $4M Angel Fund to $900M AUM | 20VC #890 · 20VC with Harry Stebbings
- 20VC: Scaling to $2BN AUM in 3 years, Fundraising Lessons and Tactics from 2,500 LP Meetings & What it Takes to Build a Firm That Stands the Test of Time with Harley Miller, Co-Founder and Managing Partner @ Left Lane Capital
- every mention in 2022, scene by scene →
2021 6 mentions in 1 episode
2017 3 mentions in 2 episodes 2 per episode
- 20VC: Overcoming The Engineer Boys Club, Disrupting The "Pink Aisle" & Why VCs Are Missing A Trick Not Investing In The CPG Space with Debbie Sterling, Founder & CEO @ Goldieblox
- 20VC: The 3 Forms Of Edge A Founder Can Have, Lessons From Being on A Board With Bill Gates & Why There Are A Lot Of Tourist VCs Who Are Going To Lose A Lot Of Money, with Josh Wolfe, Co-Founder @ Lux Capital
- every mention in 2017, scene by scene →
One line per show, most statements first. The link opens Harley's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
| 20VCLEDGER | President, Shopify | 2 +1 | 29 | 50% 5/10 | full record on 20VC → |
| KNOWLEDGE PROJECTLEDGER | President, Shopify | 2 | 26 | 100% 2/2 | full record on the Knowledge Project → |
| STARTUP IDEASLEDGER | President, Shopify | 2 | 21 | 80% 4/5 | full record on the Startup Ideas Podcast → |
| FOUNDER'S JOURNALLEDGER | President, Shopify | 1 | 7 | 100% 2/2 | full record on Founder's Journal → |