Brandon speaks with Avrum Laurie, VP of Product at Wealthsimple and his former boss at Freshbooks over a decade ago.

Avrum is an exceptional product mind, and is equally cogent in engineering and design. Brandon and Avrum discuss his journey from big company PM at Microsoft to his foray into startups Freshbooks and Wealthsimple, which he helped build into two unicorns over the last decade.

Given their shared history at Freshbooks, Avrum and Brandon go deep on some key projects they worked on, and reflect on the challenges and lessons they held. Avrum shares his philosophy on product leadership, and finally explains why Wealthsimple has so many damn apps.

Brandon speaks with David Hariri, co-founder of Ada, an AI powered customer support platform that raised at a 1.2B valuation in May 2021, entering the very rare echelon of Canadian tech startups reaching unicorn status. Ada enables large customers like Zoom to deliver great customer support experience at scale.

David recounts his upbringing, and the myriad of experiences that led him to be a developer and designer at Teehan and Lax, which was acquired by Facebook. He also covers the epic story of founding his first startup, Volley, almost shutting it down, and then betting their last 9 months of runway into pivoting into what became Ada. It's a great example of persistence and the ups and downs of startups.

In our first episode ever, Brandon speaks with Craig Miller, the former CPO & CMO of Shopify and a company legend. He joined the company when it was worth less than $100M and 70 employees, and by the time he left it had grown to over $130 BILLION and 10k employees. He was the company's first marketer, and then built up the growth team as it's CMO. Mid-tenure, Craig took over the product team which he grew from 5 to 250.

The winding conversation covers Craig's early career in engineering and marketing, mental models for leadership and product, and tons of stories from his 9+ years at Shopify, from the earliest days to the present.

0:00​ - Intro

1:06​ - What's the vague experience listed on your LinkedIn called, "Owner"?

3:52​ - What happened after "Owner", aka Kijiji

6:52​ - How Craig came to run Marketing at Kijiji despite being an electrical engineer

8:54​ - The start of the Shopify story

11:49​ - The PS that changed Craig's Life (https://medium.com/inside-shopify/the...​)

14:33​ - Craig's Big Hairy Audacious Goal for Shopify

16:00​ - Canadian tech imposter syndrome

18:44​ - "If you have ambition, you're an entrepreneur"

25:35​ - Why Craig hired me, and his thoughts on interviewing/hiring

30:13​ - Being a product exec role at a hyper-growth company

34:32​ - Leading through others

45:52​ - Projects or features that launched at Shopify that are great examples of PM thinking at the company

53:38​ - The importance of the details

1:02:10​ - Scaling the product management team from 5 to 250

1:08:30​ - What Craig is most proud of during his time at Shopify

1:10:00​ - What Craig is doing now

1:15:00​ - Final question - what's the single most important mental model or principle you have for life, work or both?