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."It's funny because, in our business, I'm wrong a lot," Sacca says. "As funds go, we've been one of the least wrong, but we're still wrong like a third of the time. It's just, when we're right, we're really f*cking right."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.

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."God bless anyone turning their lights off, and moving to LEDs," Sacca says. "That stuff does matter. But the reality is: If we're going to change stuff at scale, we have to completely redo how energy is generated on this planet."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.

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 other industries, you're acquiring a new customer and then that's it, right? Or maybe they come back every few years," says Spear. "Our customers are coming back every month, sometimes even sooner than that. In 2020, over 60% of our net revenue was from repeat transactions."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.

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 comfortable going on sale."Discounting is a really slippery slope," she says. "It's just a hard relationship with the customer to back out of, and one that can dilute the brand and tell the customer essentially that they don't ever need to buy full price."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.

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. "If I said you want to go exercise and run faster, you would think about brands like Nike," Krim says. "But if I say go get a better night of sleep, there's really no brand that comes to mind for most consumers. We want that to be Casper."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.

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."When I was younger, I think everyone always was like, 'You shouldn't be emotional in business. You can't have empathy,'" Kadakia says. "But at the end of the day, the best brands are the ones that understand, emotionally, what's going on."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.

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."Retailers have a hard time understanding sometimes that it's a contact sport," Smith says. "We are often protective in our own direct-to-consumer bubble, but in the greater system, the game's not really that fair, at all."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.

A look at our discussions for season two of In Conversation with Shopify Plus, featuring:Philip Krim, co-founder and CEO, CasperWeb Smith, founder, 2PMPayal Kadakia, founder and executive chairman, ClassPassAriel Kaye, founder and CEO, ParachuteHeather Hasson and Trina Spear, co-founders and co-CEOs, FIGSChris Sacca, co-founder, Lowercarbon Capital

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.

Tim Brown, co-founder and co-CEO of Allbirds, discusses why only bad retail—not all retail—is dying, how he navigates the unique position of having two chief executives at his company, and Allbirds' quest to achieve what has never been done before: run a billion-dollar business without leaving any carbon footprint behind."One of the challenges with a topic like sustainability is that it means 10 different things to 10 different people," he says. "Where we've landed as a business is that they must all ladder up to this unifying metric around carbon. Carbon is the thing that we must get under control."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.

Dani Reiss, president and CEO of Canada Goose, discusses how the future is omnichannel, why, as other brands rush to sell direct to consumer, the crucial role wholesale still plays, and how he once asked his own dad to step down as CEO. And if you're in a rut at your job and need a brutally honest new perspective about how to get better, how's this for a piece of advice?"Someone once said to me, 'A great way to look at your business is: Fire yourself, then rehire yourself five minutes later and look at the business again, as if you're just starting from scratch'" he says. "In that, see what could be done differently."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.

Dylan Lauren, founder and CEO of Dylan's Candy Bar, discusses the economics of flagship stores, why it's so personal to her to remain hands-on atop her company, and why her father, the iconic fashion designer Ralph Lauren, told her to go bigger—not smaller—when launching her candy empire."He understood that it was Disneyland," she says. "When I took the first flagship, he's like, 'Go bigger. Don't do a little small mom-and-pop candy store. Make it big.' I took 15,000 square feet, which is a big risk, especially in New York City. But he really understood that right from the start."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.

Steve Madden, founder of the billion-dollar footwear brand that takes his name, discusses why there'll never be a replacement for retail, what he thinks of “The Wolf of Wall Street”—the famous Leonardo DiCaprio movie that features the story that led to his downfall—and his return from addiction and 31 months behind bars. “First of all, getting out of prison—it's the greatest feeling,” he says. “For the first month, you're floating in the air.” 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.

A look at our discussions for season one of In Conversation with Shopify Plus, featuring:Steve Madden, founder, Steve MaddenDylan Lauren, founder and CEO, Dylan's Candy BarDani Reiss, president and CEO, Canada GooseTim Brown, co-founder and co-CEO, AllbirdsSeema Bansal, co-founder, Venus ET FleurChip Wilson, founder, Lululemon