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Leading with your gut

Lifeway Foods’ Julie Smolyansky

Tapping into both organization wisdom and her intuition, Lifeway CEO Julie Smolyansky embraced action amid uncertainty as she worked to keep her manufacturing open and kefir beverages on supermarket shelves during the pandemic-driven food crises of 2020.

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Relief funding & crowdfunding in a crisis

IFundWomen’s Karen Cahn

Early in the pandemic, Karen Cahn of IFundWomen shared a quick tutorial on how to access the US’s then-nascent emergency relief funds for businesses. While some specific advice in this episode is past its sell-by, her mindset of using crisis to clarify your purpose is evergreen.

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Take on Goliath — and win

Dropbox’s Drew Houston

When Drew Houston founded Dropbox, he knew he faced some fierce competition (hello, Google, Apple, and Microsoft). But he didn’t back down from the fight. Why? Because he believed in his product, and he knew he had an advantage those big, cumbersome competitors could never exploit: Dropbox was lean, focused, and fast. Hear how he outmaneuvered the big guys – and what’s next for Dropbox. Cameo appearances: Mark Pincus of Zynga, Shellye Archambeau of MetricStream.

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The case for bootstrapping

Mailchimp’s Ben Chestnut

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).

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To scale, you must master the art of storytelling

Charity: Water’s Scott Harrison

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.

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Learn from every “no”

Walker & Co.’s Tristan Walker

The best business ideas often seem laughable at first glance. So if you’re hearing a chorus of “No’s” — it may actually be a good sign. So don’t be discouraged by rejection. Instead, learn the different kinds of “no.” That’s what Tristan Walker did. After stints at successful startups, he launched Walker & Company, makers of the Bevel razor, and learned the secret of how to talk with investors who may or may not share your vision.

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Raise more money than you need

Minted’s Mariam Naficy

Think you’ve raised enough money for your startup? Think again. You’ll face a minefield of unexpected expenses — and opportunities. So raise more money than you think you need — possibly a lot more. MInted founder & CEO Mariam Naficy shares her white-knuckle experiences founding startups that survived two financial crashes – online cosmetic company Eve.com in the ’90s, and the design boutique Minted.com today.

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