EP66: Harley Finkelstein: Scaling Shopify with Luck, Passion and Love for the Customer

As hard as it might be to believe, the pandemic we’re experiencing brings opportunities with it, not just tough times - but you’re going to need some inside expertise to make your new ecommerce venture thrive.

Harley Finkelstein is an entrepreneur, lawyer, and the Chief Operating Officer (COO) of Shopify. He founded his first company at age 17 while a student at McGill and went on to complete his law degree and MBA at the University of Ottawa, where he co-founded the JD/MBA Student Society and the Canadian MBA Oath. Harley is an Advisor to Felicis Ventures, and one of the "Dragons" on CBC's Next Gen Den. Recently, he received the Canadian Angel Investor of the Year Award, Canada's Top 40 Under 40 Award, and was inducted into the Order of Ottawa. From 2014 to 2017, Harley was on the Board of the C100, and in December 2017 he was appointed for a 5-year term to the Board of Directors of the Canadian Broadcasting Corporation (CBC).

On this episode of the Perfectly Mentored podcast, Jason and Harley dive deep on putting the necessary tools and power to succeed in retail in the hands of small businesses, how to understand and effectively reach your ideal customers, and keeping your customers around with a dose of qualitative insight. Tune in for actionable advice at every level, from a true legend in his industry.

Topics Covered:

Who is Harley Finkelstein? [00:15]
How did the entrepreneurial journey start for Harley? [02:24]
Where does luck figure into business? [09:00]
How does discomfort promote growth? [11:01]
Why is it important to level the retail playing field? [13:10]
Is it wrong to want to build an empire? [16:59]
What’s the low-down on the Shopify fulfillment network? [19:18]
How vital is it for customers to get that they need to own their brand? [23:31]
Is multichannel the way to go right now? [26:17]
How can I best communicate with my customers? [30:39]
With more Shopify stores open now, how many become successful? [32:19]
Where are the opportunities in the ecomm space at the moment? [37:29]
What’s the difference between “scrappy” and “sloppy”? [41:25]
Where is ecomm now, and where is it going? [47:31]
How will travel and tourism change going forward? [48:29]
What are stores using to track and understand their ideal demographic? [50:01]
How do you scale what you cannot measure? [51:24]
Which apps are must-haves for the beginner Shopify store? [53:26]
How can I get more involved? [55:09]

Connect with Harley Finkelstein

Harleyf.com Twitter LinkedIn

Connect with Jason Portnoy

jportnoy.com LinkedIn

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