As dangerous as obstacles and setbacks may appear, they can also present opportunities. Robert Reffkin, founder and CEO of the real estate platform, Compass, knows this well. The trick, he says, isn’t to avoid obstacles at all cost, but rather, to identify them quickly as resources you can harness. “You can’t do great things in the world if you don’t have that entrepreneurial, ‘I can do it’ energy,” Reffkin says. “And how do you get that energy? You dream a big dream.”

How do you win the war for talent? Send your frontline workers to online school. That’s the pitch Rachel Carlson has made to businesses from Chipotle to Disney, Walmart to Waste Management. As co-founder and CEO of Guild Education, Carlson helps workers get online degrees and certifications as a free employee benefit. To meet the ongoing need for upskilling, Carlson says, company-sponsored classes should be as ubiquitous as company-sponsored health plans — because the ROI is astonishingly high.

Scaling isn’t only about scaling UP – it’s about scaling OUT: to new products, new verticals, new customers. And to do this, you’ll need to build bridges. No one knows this better than Daniel Lubetzky, the founder and executive chair of snack food company KIND. Daniel has spent his whole life working to bring together disparate supply chains, products, and communities. Through it, he’s learned the right – and the wrong – way to connect. That means building bridges that people actually want, letting people meet him halfway, and focusing on the foundations so those bridges last forever. Cameo appearance: Bianca Wylie (Public tech advocate).

Drew Houston knows if Dropbox is going to design for the future of work, then its own workforce needs to live in that future, right now. He discusses Dropbox’s move toward the virtual-first workplace — and how its benefits extend far beyond pandemic times.

A study in the fall of 2020 — deep into the work-at-home movement — makes a persuasive case that shared offices are productive places to work and, especially, to co-create. Gensler Group co-CEO Diane Hoskins shares fresh insights on the future of our workplaces.

Can you turn the remote-work scramble into a long-term benefit? Wences Casares runs a fully distributed company at his unicorn bitcoin startup, Xapo. For Wences, remote work is an intentional choice, one that celebrates the creativity and freedom of being released from geographical boundaries – and turns remote work into a striking advantage.

What if your idea is so radical that people have trouble grasping what it is – or even believing it won’t harm them? Every founder believes their product is revolutionary – and the more revolutionary their product, the more reassuring they’ll need to be to get consumers on board. No one knows this better than Wences Casares, the trailblazing entrepreneur credited with bringing crypto to Silicon Valley (and convincing Reid himself). With his unicorn startup Xapo, a Bitcoin wallet, Wences aims to reassure the masses that Bitcoin isn’t as different – or as dangerous – as they may think.

Faced with an impossible challenge? Don’t reinvent the wheel. Find someone who’s already solved the problem – and help those inventors keep inventing. Megan Smith calls that technique “scout and scale.” She did it as United States CTO under President Obama (launching the U.N. Solutions Summit and a tech jobs tour). She did it at Google (acquiring startups to bring famed products to life). She did it as CEO of PlanetOut. And she continues today with her new company shift7. Cameo appearance: Monique Sternin (adjunct professor at Tufts University).

Your first hires are your cultural cofounders. And it’s worth your time to get every one right. Workday CEO Aneel Bhusri personally interviewed his first FIVE HUNDRED employees at Workday. He knows how to map back from the culture he wants, to employee attributes to interview questions. Today, with 8000+ employees and $2b in annual revenue, Workday is consistently rated one of the best places to work.

Can’t find the star employees you need? Then make them. That’s what Marissa Mayer did when she founded the Associate Product Manager program at Google — one of the company’s crown jewels. She mentored a team of young, hungry, talented employees in the ways of Google, and they helped drive its success. She followed that same mindset when she became Yahoo CEO, a role she reflects on in the show.