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How to turn intentions into action

15 Percent Pledge’s Aurora James

In May 2020, as companies began making promises about how they’d help Black-owned businesses, Aurora James launched the 15 Percent Pledge with an Instagram post. Tagging major retailers, she declared that 15% of retail shelf space should belong to Black-owned businesses. Learn the tactics and strategies that allowed one small, dedicated effort to unlock $10 billion in revenue.

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How Peloton keeps pushing through resistance

Peloton’s John Foley

Skepticism and doubt are no strangers to John Foley, the founder and former CEO of Peloton. In 2020, the company was supercharged by pandemic demand. However, in 2021, the company faced a slew of new headwinds, from product-safety issues to investor skepticism. But he doesn’t see skepticism as a sign of weakness. He expects it, and learns from it.

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Episode 80: Masters of Scale

What investors really look for

Shark Tank’s Mark Cuban

No one knows the fundraising game like Mark Cuban, serial entrepreneur, investor, and star of Shark Tank. For founders, identifying the right source of capital, under the right terms, can provide a thermal updraft. But as Cuban explains, there are always strings attached when you bring on a financial partner — and those strings can pull you crashing down if you don’t understand them properly. Cuban shares what investors look for in a founder, and what entrepreneurs should be looking for in return.

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Wartime leadership

Nike’s John Donahoe

When he became CEO of Nike in January 2020, John Donahoe had a game plan. But then lockdowns began and he had to adjust, assuming what he calls a “wartime” approach to leadership. Donahoe’s view is that, in crisis, top-down stewardship matters more than ever. To not only survive but come out in a stronger position, he is leaning into the brand’s legacy, his team’s strengths, and booming direct-to-consumer digital engagement.

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Episode 75: Masters of Scale

How to be the steward of your idea

Pioneers of AI’s Rana el Kaliouby

Great entrepreneurs aren’t just product obsessed; they’re impact obsessed. Rana el Kaliouby, co-founder and CEO of Affectiva, has spent most of her career thinking about how to project – and steward – the possible uses of artificial intelligence. Affectiva uses AI to read people’s emotional states, but Rana won’t put her software to work for just anyone. She’s walking a fine line between thoughtfully nurturing her idea and being a cranky custodian: potentially throttling the scale of her business. It’s a risk she’s willing to take. She understands that entrepreneurship isn’t just about providing a product or service that people love, or creating jobs; it’s about asking: “Am I making a net contribution to society – not just right now, but for future generations?”

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Episode 69: Masters of Scale

The empathy flywheel

Nextdoor’s Sarah Friar

A social network that limits your network? Yes. Meet Nextdoor, a hyperlocal social network that’s all about who you really are and where you really live. Although it goes against everything that we’ve come to expect from social networks, Nextdoor’s secret to scale lies in real personal connections based on empathy and kindness. And this is what Nextdoor CEO Sarah Friar knows: No, these connections don’t scale as fast – but they tend to be stronger. And they can be the flywheel that drives you to scale. 

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Episode 65: Masters of Scale

How to turn skeptics into fans

Peloton’s John Foley

Casual fans come and go. But converts stick with you – and spread the word. The trick is knowing how — and WHEN — to convert skeptics into superfans. No one knows this better than Peloton Co-founder and CEO John Foley, who has one of the most epic “No-to-Yes” stories in startup history. When he founded the company in 2012, skeptics abound — especially among investors. But John pushed forward, convincing co-founders, angel investors, and then riders, one at a time. As he converted those skeptical customers — in their flagship fitness studio, in their stores, and on their at-home bikes — the feedback loops kicked in. After pedaling in place for years, Peloton rocketed up the hill to its 2019 IPO. Cameo appearances: Melanie Curtis (professional skydiver).

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Episode 46: Masters of Scale

Make it epic

Black-Eyed Peas’ will.i.am

What can entrepreneurs learn from a genre-crossing, multi-platinum musician? How to take a big opportunity — and leverage it into something epic. From his earliest days, as a founding member of the Black Eyed Peas, will.i.am learned from mentors how to not only identify big opportunities, but compound them. From the Super Bowl to the first iTunes commercial; from the founding of Beats and his tech company i.am+ to a song beamed back from Mars — his ability to bring multiple stakeholders together to leverage partnerships and compound possibilities will inspire founders at any stage of scale. Cameo appearance: Jeremy Siegel (urban designer, Bjarke Ingels Group).

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Episode 41: Masters of Scale

Entrepreneurship as a second act

Goop’s Gwyneth Paltrow

Gwyneth Paltrow transitioned from Hollywood star to start-up founder with her lifestyle brand Goop by leaning into what she knew, embracing what she didn’t, and coming up with strategies to fill the gap.

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