Billionaire venture capitalist Chris Sacca shares insights on leadership challenges in Silicon Valley, the reality of 'Shark Tank' deals, and his missed investment opportunities. He discusses the importance of tailoring pitches to investors and reflects on being wrong in the venture capital business.

Billionaire venture capitalist Chris Sacca discusses the balance between profitability and sustainability for businesses, the importance of climate tech investments, and the need for systemic changes to combat climate change. He emphasizes the significance of shifting energy generation methods on a global scale and investing in companies that offer valuable contributions.

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.