In Conversation with Shopify Plus

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.

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.

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, 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.

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.

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.

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.

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

Hear Philip Krim on how the Casper CEO navigates tricky inventory management problems. ClassPass founder Payal Kadakia details just how a company survives when 95% of its revenue is wiped away in an instant. And Chris Sacca, the billionaire venture capitalist and former “Shark Tank” star, on the right and wrong ways for a company to pitch an investor.

Brought to you by Shopify Plus, the enterprise platform powering brands from Allbirds and Gymshark to Staples and Heinz. Join the revolution at shopify.com/plus.

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.

"I think what we're seeing is the death of wholesale," he says. "If you had to look at the companies that are surviving now and the ones that are dying, anyone in wholesale is dying."

Brought to you by Shopify Plus, the enterprise platform powering brands from Allbirds and Gymshark to Staples and Heinz. Join the revolution at shopify.com/plus.

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.

"Never in a million years did I think that Kourtney Kardashian and Khloe Kardashian would share a post of Venus ET Fleur," she says. "But what we didn't think of was the supply chain. Can we actually fulfill these orders?"

Brought to you by Shopify Plus, the enterprise platform powering brands from Allbirds and Gymshark to Staples and Heinz. Join the revolution at shopify.com/plus.