Disclosure
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.”
Prediction Not checkable as stated
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.”
Disclosure
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 …”
Opinion
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.”
Insight
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…”
Opinion
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…”
Insight
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…”
Opinion
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.”
Insight
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…”
Insight
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 …”
Insight
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…”
Opinion
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.”
Insight
Harley Finkelstein: Earnings calls must be treated as storytelling opportunities
“This idea that even the way that I treat earnings, it's not an earnings call for me. It's a storytelling opportunity.”
Insight
Finkelstein: Passion-based 'life's work' entrepreneurship is historically unprecedented
“Forced entrepreneurship and passion-based entrepreneurship are very, very different things. And the idea of us, you doing your life's work and me doing my life's work, that is a concept that was foreign to our parents and grandparents.”
Insight
Finkelstein: Emulating a single mentor fully forces you to adopt their flaws
“If you try to cargo cult everything about one particular person, you're going to adopt all their good stuff and all their bad stuff. Instead, it's much easier to figure out what are the couple things I want to get good at.”
Insight
Finkelstein: Leaders should rotate business coaches once their toolbox is exhausted
“One of the things I think about coaching and business coaches in particular is at some point, you end up hearing a lot of the same stories or lessons or tools, meaning they have this wonderful toolbox, and part of what you're paying them to be your coaches for…”
Insight
Finkelstein: App creators should call their first five users directly
“Make sure the app adds a lot of value, and then the first five people that installed it, like, call them and ask them how you can make it better, and if you've made it better and they're happy, ask them to write a review”
Assertion Supported
Finkelstein: Shopify processes about 12% of all U.S. e-commerce
“Shopify basically runs about 12% of all U.S. E-commerce. So if you were to think about, like, just in terms of size-wise, like, we're like the second largest checkout on the internet in the U.S. At least”
Disclosure
Finkelstein: Multigenerational trauma drives a scarcity mindset and high career standards
“I think generally I do not have an abundance mindset about the things in my life. Some of that may be, I don't know, this is going deep in the first minute, but some of them might just be like multi-generational trauma, which I actually believe in. I think I c…”
Disclosure
Finkelstein: Father served five to six years for white-collar crime
“Was when I was 17, my dad was arrested... He was arrested for white collar crimes and for business crimes... And he was willing to risk what ended up being five or six years of federal prison time to provide that for us.”
Disclosure
Finkelstein: Storytelling provides his highest value to Shopify
“The way that I think I had the most amount of value to Shopify is the same thing that I want to be well-classed at, which is I want to be a great storyteller.”
Assertion Supported
Finkelstein: Shopify opens Montreal and Toronto offices to entrepreneurs on Sundays
“Sundays here at Shopify. We have something called builder Sundays. So we open up the offices. It's done in Montreal and Toronto. So anyone in the city that's an entrepreneur can come in and work from here.”
Insight
Harley Finkelstein defines high agency as single-threaded problem ownership
“High agency is someone that sees a problem and says, I'm going to fix it, and then fixes it themselves, that they take, they put themselves into the role of single-threaded owner, responsible person.”
Disclosure
Finkelstein splits week into meeting days and Tuesday/Thursday maker days
“I try to kind of bundle my meeting days on certain days, usually Monday, Wednesday, Fridays, and then more of my, like, my maker days, Tuesdays and Thursdays, where I can have long form blocks of time to do thinking, to do writing”
Harley Finkelstein