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In Conversation with Shopify Plus


The can't-miss interview series featuring only the best and brightest in business.

Popular episodes

Chris Sacca on Attracting an Investor, and How to Write a Pitch Email That Actually Converts

Oct 14 • 56:54

In part two of two, Chris Sacca, the billionaire venture capitalist and former "Shark Tank" star, discusses his views on the leadership efforts of some of the biggest names in Silicon Valley, what really happens behind the scenes on “Shark Tank,” and what he thinks about the deals for him—Airbnb, Dropbox, GoPro—that got away....

Chris Sacca on Profitability vs. Sustainability, and the Types of Entrepreneur He Invests In

Oct 13 • 42:46

In part one of two, Chris Sacca, the billionaire venture capitalist and former "Shark Tank" star, shares his thoughts on the right mix between profitability and sustainability for a business, what he likes to see from investors in a pitch meeting with him, and how climate tech—his new investing target—belies the greater challenges facing our planet....

Heather Hasson and Trina Spear on Running a Pop-Up Store, and How to Price Your Goods

Oct 4 • 44:45

Heather Hasson and Trina Spear, the co-founders and co-CEOs of FIGS, discuss how to run a great pop-up store experience from start to finish, what to consider when pricing your goods and how that can dictate how the consumer perceives your brand, and why cornering niche markets can mean powerful, and repeating, revenue returns....

Ariel Kaye on the Future of Office Work, and to Discount or Not to Discount

Oct 4 • 36:07

Ariel Kaye, the founder and CEO of Parachute, tells the precise offline marketing tricks her famed home lifestyle brand uses to great success, what the future of work—between office work and work from home—looks like in the direct-to-consumer space to her mind, and when it comes to the appeal discounting, Kaye offers a word of warning for any company that gets too comforta...

Philip Krim on the Best PR Strategies, and the Right Hires, to Build a DTC Brand

Sep 13 • 45:07

Philip Krim, the co-founder and CEO of Casper, discusses navigating very tricky inventory management challenges, the exact PR and marketing strategies his company used to great success in its earliest days, and the blueprint for how Casper plans to become the number one brand consumers turn to when they think of sleep. ...

Payal Kadakia on Becoming a Unicorn, and What to Do When 95% of Your Revenue Vanishes

Sep 1 • 49:35

Payal Kadakia, the founder and executive chairman of ClassPass, discusses what changes when a company reaches a $1 billion valuation and becomes a unicorn, representation problems in the fundraising process, and how to survive when 95% of your revenue vanishes into thin air....

Web Smith on Selling the Right Way on Amazon, and the Future of Ecommerce Returns

Sep 1 • 41:02

Web Smith, the founder of 2PM, the media and consulting company that exists most notably as a very well-trafficked and influential newsletter by the same name, discusses what direct-to-consumer brands should expect from the future of ecommerce returns, who the most iconic retail startup founders are today, and why the world of DTC isn't as cuddly as you might think....

Introducing Season Two

Aug 31 • 01:45

Chip Wilson on the Dangers of Discounting, and His Relationship with Lululemon Now

Jan 5 • 34:13

Chip Wilson, the founder of Lululemon, discusses his relationship today with the company that made him a billionaire, the dangers of discounting, and why direct to consumer retail has won both the battle and the war....

Seema Bansal on Surviving the Kardashian Bump, and Styling Products on Instagram

Jan 5 • 25:39

Seema Bansal, co-founder of Venus ET Fleur, discusses the dos and don'ts of styling products on Instagram, setting the right boundaires when working with your spouse, and what happens to a small business when a Kardashian posts about it on social media....

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