The Founder of Insomnia Cookies Reveals Why Most CEOs Are Wrong | EP99 (feat. Seth Berkowitz) episode artwork

EPISODE · Jun 4, 2026 · 1H 6M

The Founder of Insomnia Cookies Reveals Why Most CEOs Are Wrong | EP99 (feat. Seth Berkowitz)

from Let Me Save You 25 Years

What do warm cookies, billion-dollar brands, and heated arguments have in common? More than you think.This week Shawn sits down with Seth Berkowitz, founder of Insomnia Cookies, to talk about why the best leaders don’t surround themselves with people who agree with them, they surround themselves with people willing to, “fight it out.”From launching a late-night cookie delivery business as a college student to building one of the most recognizable dessert brands in America, Seth shares why debate leads to better decisions, why founders must protect the heartbeat of the business, and why there’s rarely one “right” answer.The two also dive into the power of asking better questions, getting comfortable being uncomfortable, and why hearing customers say “that’s dumb” might actually be a good sign. Plus, Seth reveals one of the biggest internal debates in Insomnia Cookies history, and what it taught him about leadership.Because sometimes the path to the best answer starts with a good argument.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

What do warm cookies, billion-dollar brands, and heated arguments have in common? More than you think.This week Shawn sits down with Seth Berkowitz, founder of Insomnia Cookies, to talk about why the best leaders don’t surround themselves with people who agree with them, they surround themselves with people willing to, “fight it out.”From launching a late-night cookie delivery business as a college student to building one of the most recognizable dessert brands in America, Seth shares why debate leads to better decisions, why founders must protect the heartbeat of the business, and why there’s rarely one “right” answer.The two also dive into the power of asking better questions, getting comfortable being uncomfortable, and why hearing customers say “that’s dumb” might actually be a good sign. Plus, Seth reveals one of the biggest internal debates in Insomnia Cookies history, and what it taught him about leadership.Because sometimes the path to the best answer starts with a good argument. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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The Founder of Insomnia Cookies Reveals Why Most CEOs Are Wrong | EP99 (feat. Seth Berkowitz)

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Eat to Live Jenna Fuhrman, Dr. Fuhrman Our health is our most precious gift and smart nutrition can change your life. Each month, join Dr. Fuhrman and his daughter, Jenna Fuhrman as they discuss important topics in the world of nutrition. Eat to Live will change the way you eat and think about food. French Your Way Jessica: Native French teacher founder of French Your Way Boost your French listening skills and test your comprehension with this one of a kind series of podcasts. Get the chance to listen to a real conversation between native speakers talking at normal speed AND customise your learning experience through carefully designed sets of questions (2 levels of difficulty) available for download at www.frenchvoicespodcast.com. All interviews also come with the transcript. French teacher Jessica interviews native speakers of French from around the world who share a bit of their life and passion. Where else would you meet in one same place a French yoga teacher based in Melbourne, a soap manufacturer from Provence, or a couple cycling around the world? DIOSA. Carolina Sanper This podcast is a sacred space created by Carolina Sanper where you connect with your inner wisdom and embody your magnetic feminine power.It is the realization that the mystical realm is where you plant the seeds of your desired reality.It is a portal to your true essence: awareness, presence, and receiving with ease. Welcome home, DIOSA. 🖤 XXX Tech by SOVRYN Dr. Brian Sovryn The crossroads between technology, sensuality, and metaphysics - and the longest running anarchist podcast in the world! Brought to you by Dr. Brian Sovryn.

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This episode is 1 hour and 6 minutes long.

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This episode was published on June 4, 2026.

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What do warm cookies, billion-dollar brands, and heated arguments have in common? More than you think.This week Shawn sits down with Seth Berkowitz, founder of Insomnia Cookies, to talk about why the best leaders don’t surround themselves with...

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