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We Should Be Sleeping

Millennials are achieving freedom with a new definition of success. Our careers, relationships, educations, and even our politics, look nothing like our parents’. We are repapering the roadmap toward our personal goals and embracing what moves us along the way. We are adopting what works and throwing out the rest. We are tired, but not worn, in our quest to get there.We Should Be Sleeping explores the things worth losing sleep over. Each week, the hosts explore the news and topics that keep them awake. Then, guests share the intentional ways they’ve done it differently to achieve a new brand of success that's authentic, unconventional, and definitive of our generation.Not ready for bed? Tune in, because neither are we.

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Caring More With Sara Mauskopf

This week, the hosts are over winter and guest Sara Mauskopf, CEO and Co-Founder of Winnie, shares how her frustration with the long search to find child care resulted in her taking matters into her own hands by creating one of the largest online marketplaces for it. Today, Winnie is used throughout the United States and is helping connect millions of parents with high quality child care.


22 Feb 2021

Rank #1

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Spending With Purpose With Mandy Bowman

The week, the hosts break down the GameStop madness and why "narratives" played an important role in the meme stonk circus. Guest Mandy Bowman, founder of Official Black Wall Street, shares the importance of spending with purpose and supporting your community to build generational wealth.


4 Feb 2021

Rank #2

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Mastering Your Craft With Oz Pearlman

Doug's love of watching Elena of Avalor with his kid prompts a discussion about shared interests between parents and their children. Guest Oz Pearlman, Emmy-Award-Winning Mentalist, discusses how he left the corporate world to master his craft and follow his dreams to become one the world's best magicians.


28 Jan 2021

Rank #3

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Reaping Prosperity With Maria Palacio

The hosts share their thoughts on current events. Heather calls out Doug's fast food problem. Guest Maria Palacio, Co-Founder and CEO of Progeny Coffee, shares how she disrupted the Colombia coffee supply chain to bring prosperity to local coffee farmers.


13 Jan 2021

Rank #4

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Daring To Try With Anthony Pompliano

Douglas and Heather take inventory of the kitchen appliances they registered for long ago but have never used and discuss their (lowered) expectations for the new year. Guest Anthony Pompliano shares his journey as bitcoin poster boy and how creating good content is about being willing to try.


7 Jan 2021

Rank #5

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Cutting New Deals With Olivia Landau & Kyle Simon

Heather and Douglas give the only 2020 recap worth doing (the TV shows that gave them life). Guests Olivia Landau and Kyle Simon, Co-Founders of The Clear Cut, share how they are disrupting the diamond industry and why buying engagement rings online is the future of the business.


30 Dec 2020

Rank #6

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Dreaming In Color With Melissa Ben-Ishay

Douglas and Heather ask their vaccine questions and reveal their daughter's expectations for the holidays. Guest Melissa Ben-Ishay, Co-Founder and CEO of Baked by Melissa, shares her recipe for success in doing what she loves and scaling her miniature cupcake empire.ICYMI: Last week, listeners were asked to share their favorite hype songs. You can check out the Spotify playlist here.


23 Dec 2020

Rank #7

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Writing Your Ticket with Morgan Housel

Season One of We Should Be Sleeping kicks off. Heather defends why her 6,000 unread emails don't make her a sociopath, and the couple shares their top hype songs for the ages. Guest Morgan Housel, award-winning author of The Psychology of Money: Timeless lessons on wealth, greed, and happiness, discusses his evolution as a "blogger," and if people can ever truly have enough.


16 Dec 2020

Rank #8

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Mini-Series Finale: Sticking with Takeout, Shark Tank with Friends and Coffee Talk

The hosts wrap up WSBS mini-series by discussing why takeout is still the best way to support your favorite restaurants, "investing" in their friend's side hustle, the #freebritney movement, declining pre-mature birthrates and, of course, why coffee is life.


5 Aug 2020

Rank #9

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Projects, Cheese Boards, and Ignoring Kayne West

This week, our hosts share why different projects keep them sane, how much they miss cheese boards and why ignoring Kanye West's "presidential bid" is a must for democracy.


14 Jul 2020

Rank #10