Shopify

“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.”

“First I was the first non-engineer, but I think I was I was the first, in the first 20 people that joined.”

“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.”

“We're about to get to 10,000 employees.”

“And with tools like Shopify, Substack, MailChimp, Etsy, Patreon, Kickstarter, and all of these different creator platforms, the cost of failure in business today is really, really low.”

“The biggest thing that, you know, industry or market wise was, dude, there's a bunch of nine figure e-com tech businesses. None of which, like with the exception of Klaviyo and maybe Attentive have anything to do with Shopify.”

“Shopify is a sixty billion dollar company right now. I think OpenAI is thirty billion. You would have to think that the plugins to ChatGPT, which are gaining some popularity now as they're opening it up, is going to be multiples of that.”

“The cost of failure is as close to zero as it's ever been, and it will continue to fall.”

“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?”

“Toby responded to my post saying, You basically just called Sidekicks Roadmap, and Sidekicks refers to Shopify's AI-powered assistant.”

“This question would have come off as unreasonable for Toby to ask pre-AI, but with AI, the expectation of your team to get more work done with no more or even fewer people is all of a sudden totally realistic.”

“The fact that employees are going to be evaluated based on their AI usage is an amazing idea, and it is one of the only ways you can truly create positive pressure for your team to take the technology seriously.”

“Outside of the memo, I just love this idea of having to requalify for a job. It may be scary to some, but for the type of company that wants to grow, 20 to 40% per year, it needs to attract people that are excited by growing that fast, and this requalification…”