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).

TaskRabbit was founded during the 2008 financial crisis — and then and now, says Stacy Brown-Philpot, the business remains a necessity, for the community, and for the gig economy.

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).

It’s never too late to join the entrepreneurial party. We’ve all heard the stories of young geniuses, but plenty of influential entrepreneurs founded companies in their 30s, 40s, 50s. There’s value to being a late-stage founder — like the fact that you’re bringing along all your life experience. That’s what Gwyneth Paltrow did when she launched Goop. Paltrow transitioned from Hollywood star to startup founder with her lifestyle brand, which now has over 8 million subscribers — and she did it by leaning in to what she knew, embracing what she didn’t, and coming up with strategies to fill the gap. With cameo appearances by Sara Blakely (Spanx), Brian Chesky (Airbnb), Boyd Martin (Olympic horse rider), and Ruben Harris (Career Karma).

You need a great story to build a great company. No one embodies this principle more fully than Scott Harrison, founder of Charity: Water. A master storyteller, Scott built his nonprofit on 3 radical principles: (1) 100% of donations would go to water projects (2) Progress reports would be transparent, sharing victories and defeats (3) The brand’s storytelling would lead with hope instead of guilt, inspiring joyful participation without sacrificing honesty.

You can marshal the power of millennials to grow your company, but you have to redefine your concept of loyalty. To keep millennials as users (and employees), you’ll need to keep evolving — and help them evolve. No one understands this better than Brit + Co founder Brit Morin. As a maker and media creator, Brit is constantly co-evolving with her (mostly millennial) audience—and team. It’s a secret to scale with the generation adapted to a world of constant change.