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Harley Finkelstein

President, Shopify · 1 appearance on the record.

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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.

7statements → 3claims → 2claims resolved → 3.29/5average certainty → 1.71/5average debate potential → 14said about them ↓

2 supported 0 partly supported 0 contradicted 1 not checkable as stated how the 3 claims stand · each chip opens the sources

3 assertions · 4 insights · every statement was checked. The predictions and assertions are the 3 claims: statements the public record can support or contradict. 2 are resolved, and 1 names 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 joined Shopify as its first non-engineer employee
“First I was the first non-engineer, but I think I was I was the first, in the first 20 people that joined.”
Harley Finkelstein Jul 16, 2021 ▶ 8:19 Entrepreneurship In All Aspects Of Your Life w/ Shopify's Harley Finkelstein

Expressed certainty vs assessment result

none yet certainty 1
none yet certainty 2
100% certainty 3
100% certainty 4
none yet 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 Founder's Journal that made the record, most notable first. Filter by type, assessment or year in the ledger →

Insight
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.”
Harley Finkelstein Jul 16, 2021 ▶ 10:24 Entrepreneurship In All Aspects Of Your Life w/ Shopify's Harley Finkelstein
Insight
Finkelstein says the cost of failure for entrepreneurs is near zero
“I think the biggest reason is, is that the cost of failure is getting as close to zero as it's ever been. I think that's part of why you're seeing more people become entrepreneurs.”
Harley Finkelstein Jul 16, 2021 ▶ 10:45 Entrepreneurship In All Aspects Of Your Life w/ Shopify's Harley Finkelstein
Insight
Finkelstein: Executive growth must outpace company growth to keep the job
“I have to re-qualify for my job every single year, and to re-qualify to be the president of Shopify means that my personal growth has to be disproportionate to Shopify's growth.”
Harley Finkelstein Jul 16, 2021 ▶ 17:06 Entrepreneurship In All Aspects Of Your Life w/ Shopify's Harley Finkelstein
Insight
Finkelstein says college is the best time to start multiple businesses
“I think the college is the best time to start a business. I think you start five businesses. Your classmates are going to be your early adopters. Your professors can be your board of directors. You have free space because there's classrooms available everywher…”
Harley Finkelstein Jul 16, 2021 ▶ 20:39 Entrepreneurship In All Aspects Of Your Life w/ Shopify's Harley Finkelstein
Assertion Not checkable as stated
Finkelstein was one of Shopify's first 200 merchants
“And I became one of Shopify's first merchants. I think it was store 126 or 136 or so. And we, you know, first 200 stores and I sold t-shirts on Shopify throughout most of law school.”
Harley Finkelstein Jul 16, 2021 ▶ 7:09 Entrepreneurship In All Aspects Of Your Life w/ Shopify's Harley Finkelstein
Assertion Supported
Finkelstein joined Shopify as its first non-engineer employee
“First I was the first non-engineer, but I think I was I was the first, in the first 20 people that joined.”
Harley Finkelstein Jul 16, 2021 ▶ 8:19 Entrepreneurship In All Aspects Of Your Life w/ Shopify's Harley Finkelstein
Assertion Supported
Shopify approached 10,000 employees by July 2021
“We're about to get to 10,000 employees.”
Harley Finkelstein Jul 16, 2021 ▶ 16:57 Entrepreneurship In All Aspects Of Your Life w/ Shopify's Harley Finkelstein

The other half of the tape: Harley Finkelstein's own voice is left out of every number here. Other people bring the name up 12 times in 5 episodes on Founder's Journal. 2 statements on the record name them. every mention, with the transcript →

Who brings them up most Alex Lieberman 12

Statements about Harley Finkelstein, by other people (2)

Assertion Supported
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?”
Alex Lieberman Mar 1, 2024 ▶ 9:15 Amp it Up
Prediction Not checkable as stated
The cost of entrepreneurial and creative failure is at a historic low
“The cost of failure is as close to zero as it's ever been, and it will continue to fall.”
Alex Lieberman Feb 9, 2024 ▶ 15:46 The Great Online Game

Every mention by year

tap a year for its mentions
00316220212022202320242025episodesmentions
01220212022202320242025episodes it came up in
00316220212022202320242025episodesmentions per episode
2025 1 mention in 1 episode
2024 3 mentions in 2 episodes 2 per episode
2023 2 mentions in 1 episode
2021 6 mentions in 1 episode

Appearances (1)

EpisodeDateSpeaking time
Entrepreneurship In All Aspects Of Your Life w/ Shopify's Harley Finkelstein Jul 16, 2021 15m
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