In Conversation with Shopify Plus Shopify Plus

Web Smith, the founder of 2PM, the consulting company and prominent newsletter by the same name, discusses the right way for brands to sell on Amazon, who retail's most iconic founders are, and why the future of ecommerce returns may be brighter for direct-to-consumer brands.

Payal Kadakia, the founder and executive chairman of ClassPass, discusses becoming a unicorn, representation challenges among venture capitalist firms in the fundraising process, and how to survive when a brand loses 95% of its revenue all at once.

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—like Nike did for sports or Whole Foods did for nutrition—plans to become the number one brand consumers turn to when they think of sleep.

Ariel Kaye, the founder and CEO of Parachute, shares the precise offline marketing tricks her famed home lifestyle brand uses to great success, what the future of work looks like in the direct-to-consumer space to her mind, and why many brands ought to pause and think before they commit to a business model that includes frequent discounting and sales.

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.

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 will be the next great wave that makes people rich.