At Boston’s Cue Ball Group, Tony’s portfolio includes companies that employ hundreds of nail care workers, cooks and servers. So he’s asking: How can we protect hourly workers and help them prepare for an uncertain future?

Behind every successful business is a hidden back-end business powering it behind the scenes. No one knows this better than Jenn Hyman, CEO of Rent the Runway. RTR is known for creating a glamorous “closet in the cloud,” but it achieved ‘unicorn’ status by mastering the businesses behind their public-facing brand — including the world’s largest dry-cleaning operation and a data insights practice that’s changing the fashion industry. Cameo appearance: Kevin Venardos (Venardos Circus); Stewart Butterfield (Slack)

When Anne Wojcicki co-founded 23andMe, she carved out a brand-new space in personal health — helping people become experts on their bodies right down to the DNA level. Then the federal regulators came calling. But instead of trying to outwit, sneak past or straight-up fight the FDA in the name of moving fast, Wojcicki made the call to work with regulators directly and collaboratively. Hear how (and why) she embraced red tape. Cameo appearance: Daniel Ek of Spotify.

Bumble founder Whitney Wolfe Herd knows: The smallest feature can make or break your product. The challenge is recognizing the impact of that feature – and making sure it’s actually positive. This is what Wolfe Herd tapped into when she founded a dating app that required a whole new way of communication. She has become a master of understanding what her users want, and then making the small changes to Bumble that help them achieve their goals. While small changes typically lead to incremental improvements, every so often the impact is exponential. With cameo appearances by Steve Spohn (AbleGamer), and Marissa Mayer (Google, Yahoo).

You can bootstrap your business to scale, but you’ll have to make your own luck. Nobody knows this better than Mailchimp’s Ben Chestnut. He used a DIY ethos to grow a $600M company without ever raising a dollar of outside funding. The Mailchimp story is the exception to Reid’s rule (Generally: Raise more money than you think you need!). The episode explores a range of options for those who don’t fit the VC-funding mold for any set of reasons. Cameo appearances: LeVar Burton (Star Trek, Reading Rainbow, LeVar Burton Reads), Don MacKinnon (Milq), Karen Cahn (iFundWomen).

To revolutionize an industry, you have to cast off received wisdom. Shake Shack’s Danny Meyer knows this well. When he opened his first restaurant, received wisdom told him food was the star attraction. But Danny knew to focus on how customers FEEL. And it’s this feeling – Danny calls it “enlightened hospitality” — that he’s scaled. As he tells the dramatic scale story of Shake Shack, Danny shows how he cast off received wisdom and wrote his own rules.

Normally, trust = consistency + time. But when you’re scaling fast, you must find shortcuts with your partners and your users. When Daniel Ek founded Spotify, he did what few disruptors had ever done before: He worked WITH the industry he was trying to reinvent. How did Ek build a relationship with a music industry wary of piracy? He found shortcuts to trust. And not just with the music industry, but users too.