Harley Finkelstein

President, Shopify · 2 appearances on the record.

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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.

21statements → 7claims → 5claims resolved → 80%fully supported → 3.67/5average certainty → 1.86/5average debate potential → ≈4.0/5argument clarity, estimated → 5said about them ↓

4 supported 1 partly supported 0 contradicted 2 not checkable as stated how the 7 claims stand · each chip opens the sources

2 predictions · 5 assertions · 3 opinions · 8 insights · 3 disclosures · every statement was checked. The predictions and assertions are the 7 claims: statements the public record can support or contradict. 5 are resolved, and 2 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Harley argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported
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.”
Harley Finkelstein Feb 10, 2022 ▶ 45:01 Forget Zero Sum, Be Positive Sum with Harley Finkelstein | Where It Happens

Expressed certainty vs assessment result

none yet certainty 1
none yet certainty 2
100% certainty 3
83% certainty 4
100% certainty 5

weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet

How they sound: not measured why? →

We measure speaking style by listening to the audio itself, and a fair number needs at least 2,000 words from one person on tape we have measured. There is too little of Harley Finkelstein on measured tape to publish a rate. This says nothing about how they speak.

Everything Harley Finkelstein said on the Startup Ideas Podcast that made the record, most notable first. Filter by type, assessment or year in the ledger →

Opinion
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.”
Harley Finkelstein Feb 10, 2022 ▶ 27:51 Forget Zero Sum, Be Positive Sum with Harley Finkelstein | Where It Happens
Assertion Supported
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.”
Harley Finkelstein Feb 10, 2022 ▶ 45:01 Forget Zero Sum, Be Positive Sum with Harley Finkelstein | Where It Happens
Opinion
Finkelstein: Gymshark is probably one of Nike's biggest rivals
“I think Gymshark is probably one of the biggest rivals of Nike.”
Harley Finkelstein Feb 10, 2022 ▶ 52:02 Forget Zero Sum, Be Positive Sum with Harley Finkelstein | Where It Happens
Opinion
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.”
Harley Finkelstein Feb 10, 2022 ▶ 1:03:55 Forget Zero Sum, Be Positive Sum with Harley Finkelstein | Where It Happens
Prediction Not checkable as stated
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.”
Harley Finkelstein Feb 10, 2022 ▶ 1:11:13 Forget Zero Sum, Be Positive Sum with Harley Finkelstein | Where It Happens
Disclosure
Finkelstein optimizes his daily routine to completely eliminate transition time
“I'm trying to optimize my entire life for no no transition time or low transition time. So I either want to be like full on, you know, like Hustling and building our business at Shopify, or I want to be doing things that give me great, you know, great joy, bei…”
Harley Finkelstein Apr 13, 2023 ▶ 0:43 Shopify President Harley Reveals Life & Business Strategies That Will Change Your Game
Insight
Finkelstein argues working hard versus working smart is a false dichotomy
“It's a false dichotomy. It's not either you're working hard or working smart. I think there are certain times where you just have to do the work.”
Harley Finkelstein Apr 13, 2023 ▶ 3:41 Shopify President Harley Reveals Life & Business Strategies That Will Change Your Game
Insight
Finkelstein claims non-obvious mentors offer founders massive untapped informational alpha
“Non-obvious mentors actually have a non-obvious amount of alpha in terms of teaching and insight and impact that you can derive if you simply ask them about it.”
Harley Finkelstein Apr 13, 2023 ▶ 21:03 Shopify President Harley Reveals Life & Business Strategies That Will Change Your Game
Insight
Finkelstein says unheralded local business owners teach more than business books
“There is someone in your town, if you were listening, who makes like, I don't know like the caps for water bottles. Like, that person may have a huge company that no one's ever heard of, and the stories you will get, number one, will be so fascinating, but mor…”
Harley Finkelstein Apr 13, 2023 ▶ 28:05 Shopify President Harley Reveals Life & Business Strategies That Will Change Your Game
Insight
Finkelstein recommends donating to a target's charity to bypass outreach filters
“One other way that's super simple is almost everyone you want to meet has some sort of not everyone, but most people will have some sort of philanthropic charity foundation they're connected to that means a lot to them. And if you do research on them, it is ve…”
Harley Finkelstein Apr 13, 2023 ▶ 33:55 Shopify President Harley Reveals Life & Business Strategies That Will Change Your Game
Insight
Finkelstein argues one-off 'pick your brain' sessions fail to build relationships
“You don't build real community by having a one-time Let me pick your brain. Here's 10 questions, and then never call them again. You know, those people are never going to be, quote, your homies. They'll be your homies if you actually are able to create a real …”
Harley Finkelstein Apr 13, 2023 ▶ 36:05 Shopify President Harley Reveals Life & Business Strategies That Will Change Your Game
Insight
Finkelstein advises founders never to take offense at ultra-short executive meetings
“Be the person that doesn't walk out of the meeting, be the person that's not offended, like, you know, is it shitty that you drove 40 minutes or 30 minutes for a two minute meeting? Maybe, who cares? Like, the guy is running 1400 stores, he doesn't need a webs…”
Harley Finkelstein Apr 13, 2023 ▶ 42:04 Shopify President Harley Reveals Life & Business Strategies That Will Change Your Game
Assertion Supported
Finkelstein reveals Supreme finally migrated its online store to Shopify
“Supreme was one of the stores that I always wanted on Shopify, like, for decades, for, like, as long as I've been in Shopify, I wanted Supreme on, and they came on on January, in January to Shopify”
Harley Finkelstein Apr 13, 2023 ▶ 51:14 Shopify President Harley Reveals Life & Business Strategies That Will Change Your Game
Insight
Finkelstein: Support for new entrepreneurs is business coaching, not technical fixes
“Support is, is often, I think, looked at in technology companies and software companies as this tech technology support, but rather when you're talking to entrepreneurs, in many cases, first time entrepreneurs, Often what they need is they just need a voice in…”
Harley Finkelstein Feb 10, 2022 ▶ 51:24 Forget Zero Sum, Be Positive Sum with Harley Finkelstein | Where It Happens
Prediction Not checkable as stated
Finkelstein: The concept of hometown will change dramatically within 10 years
“I actually think the concept of hometown is changing. I think from where humans, like what a human says is their hometown will change fairly dramatically over the next 10 years. I think I think it'll kind of be like this, where there's a, like, you'll have an …”
Harley Finkelstein Feb 10, 2022 ▶ 1:06:48 Forget Zero Sum, Be Positive Sum with Harley Finkelstein | Where It Happens
Assertion Partly supported
Finkelstein: Joe Rogan averages 11M views per episode versus Tucker Carlson's 3.5M
“The show with the highest average views on television, sort of eye roll, but it is Tucker Carlson, whether you hate him or like him, that, that, that is, you know, that that's factual. There's about, I think there's about 3.5 million average views per episode …”
Harley Finkelstein Feb 10, 2022 ▶ 1:08:51 Forget Zero Sum, Be Positive Sum with Harley Finkelstein | Where It Happens
Assertion Supported
Ottawa meetup Fresh Founders produced Shopify, Getaround, and other major startups
“And that actually led to Fresh Founders, which was the group of a number of us that got together every Friday. And we created a tribe of our own of entrepreneurs in a city that is not inherently entrepreneurial. And funny enough, that, that group that we creat…”
Harley Finkelstein Apr 13, 2023 ▶ 15:49 Shopify President Harley Reveals Life & Business Strategies That Will Change Your Game
Insight
Finkelstein: Montreal's Immigrant Hustle Seeded Global Apparel Brands
“And I think one of the things that Montreal has done it's embraced as sort of this immigrant culture, which effectively is entrepreneurship because you have no capital, you have no experience, you have no money. So the thing to do is go and find a way to hustl…”
Harley Finkelstein Feb 10, 2022 ▶ 22:29 Forget Zero Sum, Be Positive Sum with Harley Finkelstein | Where It Happens
Assertion Supported
Finkelstein: Amazon controls 35% to 45% of US e-commerce
“In the neighborhood of 35 to 45% of all e-commerce in the United States is done on Amazon.”
Harley Finkelstein Feb 10, 2022 ▶ 40:40 Forget Zero Sum, Be Positive Sum with Harley Finkelstein | Where It Happens
Disclosure
Finkelstein: Shopify now powers about 2 million merchant stores
“We now have about two million stores on Shopify”
Harley Finkelstein Feb 10, 2022 ▶ 41:28 Forget Zero Sum, Be Positive Sum with Harley Finkelstein | Where It Happens
Disclosure
Finkelstein: A Shopify merchant makes a first sale every 28 seconds
“Every 28 seconds, an entrepreneur gets there for sale.”
Harley Finkelstein Feb 10, 2022 ▶ 45:20 Forget Zero Sum, Be Positive Sum with Harley Finkelstein | Where It Happens

The other half of the tape: Harley Finkelstein's own voice is left out of every number here. Other people bring the name up 5 times in 3 episodes on the Startup Ideas Podcast. every mention, with the transcript →

Who brings them up most Sahil Bloom 4Greg Isenberg 1

Every mention by year

tap a year for its mentions
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00112220222023episodesmentions per episode
2023 1 mention in 1 episode
2022 4 mentions in 2 episodes 2 per episode

Appearances (2)

EpisodeDateSpeaking time
Shopify President Harley Reveals Life & Business Strategies That Will Change Your Game Apr 13, 2023 41m
Forget Zero Sum, Be Positive Sum with Harley Finkelstein | Where It Happens Feb 10, 2022 38m
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