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Jason and Jenna discuss the framework he utilizes to make fast but sound decisions and how he evaluates them, knowing when to ask ‘Can this be bigger?’ versus ‘Should this be bigger?’ and why being a musician is his secret weapon.

Venture Capitalist and author, Scott Hartley joins Moe Abdou to discuss the essential role that Liberal Arts plays in Tech startups.

Irving and Jenna discuss how Bowery is shaping the next frontier of agriculture, the importance of constantly evaluating where we are and being willing to change course, Irving’s surf trip around the world and the lesson he learned about time and patience along the way.

Moe Abdou is joined by Harvard’s Jim Ryan to explore life’s other essential questions.

Tal, Kate, and Jenna discuss how bkr turned scarcity into exclusivity in the early days, how to create an addictive brand, why “there’s no such thing as a cautious and a creative,” and cultivating the grit to go for it every day. 

Erin and Jenna discuss getting into flow on the Dream, Girl set and finding the moments that light you up, the importance of giving yourself time to process your experiences, her mission to debunk the starving artist myth, and the gift of presence.

Hooman and Jenna discuss his experiences building Ando with David Chang, learning the real meaning of CEO leading AddThis through the recession, journaling techniques to explore, understand, and expand new ideas, and why he always challenges himself by asking: Am I gaining enough exposure?

Scott and Jenna discuss equal and opposite reactions in business, why bootstrapping saves your mission from being edited, Boll & Branch’s road to profitability, and cash management strategies for startups.

Sarah and Jenna discuss solitude during the early days and why starting a company is like swimming to a new island (just keep swimming!), the inventory room a-ha moment that inspired Bento and saved MM.LaFleur from potential bankruptcy, and how MM’s ‘Nothing above you. Nothing below you.’  value boosts retention (only 2 out of 160 team members have left MM in five years). 

Shan and Jenna discuss the meeting with Kevin Ryan that inspired her to launch Gilt Taste, why you should take every pitch meeting seriously, how ZOLA’s missions and operations empower the team to quickly test projects, and why Shan always asks: Could this be bigger? 

Caterina and Jenna discuss why the first step of creating something great is getting out of your every day routine, why you shouldn’t worry about naysayers in the early days, they will get it eventually (it’s okay if they don’t), Breather’s self-forming culture committee and the team’s ‘Treat everyone like it’s your birthday’ value, as well as Caterina’s personal calling to show a spirit of benevolence towards others, especially women, who need advice or mentorship.

Moe Abdou is joined by Warren Berger to explore why questions are more important than answers.

Kelsey and Jenna discuss what personalized care looks like at scale, why we can’t tap its true potential until we change the way we talk about and treat care professionals, how Honor directly connects Care Pros and families with the team, as well as their efforts decreasing unpredictability in health care by helping us plan for aging.

Adam and Jenna discuss product development at Fabric, why the team established their values immediately, how to identify investors who are eager to fill your blindspots, and the importance of conducting values check-ups to avoid morphing into the industry you launched to disrupt.

Moe Abdou is joined by consumer maven, Tara-Nicholle Nelson to explore the making of a transformational consumer.