BOSSY

Morning Brew
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Sep 4, 2025 • 23min

How To Start Over With A Second Business Idea, with the Founder of Care.com

In this episode Tara runs through 10 Questions for a Boss with Ohai.ai CEO Sheila Lirio Marcelo, who is also the founder of Care.com—the world’s largest care marketplace. Listen to hear Sheila talk about the transition from being the CEO of a private company to a public one, how she handled a serious hit to the reputation of her company, and finding the strength and energy to found a second company. 00:00 Intro 00: 53 Sheila’s morning rituals 02:22 What helped give Sheila confidence after Care.com went public 04:52 Office Hours segment, presented by Amazon Ads 06:02 How Sheila handled comments made about “the care economy” being for women 08:42 How Sheila handled a particularly dark moment for Care.com  10:52 What Sheila thinks about competitors of Care.com 12:23 How Ohai.ai came about as an idea and then became a business 14:56 Sheila’s attitude towards building a second company 17:56 How Sheila handled her insecurity when building her businesses This episode is presented by Amazon Ads: Amazon Ads help you show up for customers—right when they’re looking for you 💌 Want to get all of Tara’s resources? Subscribe: https://www.morningbrew.com/bossy-show/subscribe   Get More BOSSY Watch BOSSY on YouTube: www.youtube.com/@BOSSY_Show   Follow BOSSY Instagram: https://www.instagram.com/bossy_show/    TikTok: https://www.tiktok.com/@bossy_show  Twitter: https://twitter.com/BOSSY_Show  BOSSY, hosted by Tara Reed, brings you no-BS conversations about entrepreneurship, confidence, and leaning into your inner boss. Each episode, Tara puts on her boldest outfits and offers tactics and unapologetic advice – from the big names you love to the minds behind your favorite brands. New episodes drop on Thursdays – if you like the show, leave us a review and share with a friend! Learn more about your ad choices. Visit megaphone.fm/adchoices  Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jun 20, 2025 • 11min

Responding to Your Toughest r/Entrepreneur Questions: Succeeding as an Introvert, Using AI, and More

Tara reads and answers some of the most pressing questions from Redditors seeking entrepreneurship advice. How do you become a successful entrepreneur as an introvert? Is AI actually going to take over everything? Can you become a successful business leader without vision? 💌 Want to get all of Tara’s resources? Subscribe: https://www.morningbrew.com/bossy-show/subscribe   Get More BOSSY Watch BOSSY on YouTube: www.youtube.com/@BOSSY_Show   Follow BOSSY Instagram: https://www.instagram.com/bossy_show/    TikTok: https://www.tiktok.com/@bossy_show  Twitter: https://twitter.com/BOSSY_Show  BOSSY, hosted by Tara Reed, brings you no-BS conversations about entrepreneurship, confidence, and leaning into your inner boss. Each episode, Tara puts on her boldest outfits and offers tactics and unapologetic advice – from the big names you love to the minds behind your favorite brands. New episodes drop on Thursdays – if you like the show, leave us a review and share with a friend! Learn more about your ad choices. Visit megaphone.fm/adchoices Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jun 19, 2025 • 14min

Reacting to Unhinged Emails from Tech Founders (Elon Musk, Elizabeth Holmes, and More)

Tara reviews the leaked emails of some of the leading figures in tech and shares her candid reactions, thoughts, and insights on each. From Elizabeth Holmes’ daily schedule to Elon Musk’s rage email to Sam Bankman-Fried’s unhinged musings, these are some emails you don’t want to miss. 💌 Want to get all of Tara’s resources? Subscribe: https://www.morningbrew.com/bossy-show/subscribe Get More BOSSY Watch BOSSY on YouTube: www.youtube.com/@BOSSY_Show Follow BOSSY Instagram: https://www.instagram.com/bossy_show/ TikTok: https://www.tiktok.com/@bossy_show Twitter: https://twitter.com/BOSSY_Show BOSSY, hosted by Tara Reed, brings you no-BS conversations about entrepreneurship, confidence, and leaning into your inner boss. Each episode, Tara puts on her boldest outfits and offers tactics and unapologetic advice – from the big names you love to the minds behind your favorite brands. New episodes drop on Thursdays – if you like the show, leave us a review and share with a friend! Learn more about your ad choices. Visit megaphone.fm/adchoices Learn more about your ad choices. Visit megaphone.fm/adchoices
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Jun 11, 2025 • 11min

From $5 Billion to Near Irrelevancy: What Happened With Clear?

Is Clear about to fail? What was once a thriving business valued at $5 billion with only the TSA as a competitor, is now facing several technological and economic challenges that threaten to render their business irrelevant. But Tara sees reason that Clear Security might survive anyway. Do you agree? 💌 Want to get all of Tara’s resources? Subscribe: https://www.morningbrew.com/bossy-show/subscribe Get More BOSSY Watch BOSSY on YouTube: www.youtube.com/@BOSSY_Show Follow BOSSY Instagram: https://www.instagram.com/bossy_show/ TikTok: https://www.tiktok.com/@bossy_show Twitter: https://twitter.com/BOSSY_Show BOSSY, hosted by Tara Reed, brings you no-BS conversations about entrepreneurship, confidence, and leaning into your inner boss. Each episode, Tara puts on her boldest outfits and offers tactics and unapologetic advice – from the big names you love to the minds behind your favorite brands. New episodes drop on Thursdays – if you like the show, leave us a review and share with a friend! Learn more about your ad choices. Visit megaphone.fm/adchoices Learn more about your ad choices. Visit megaphone.fm/adchoices
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Mar 27, 2025 • 39min

Changing Your Money Mindset with Abi Levine

In this episode, Tara sits down with CEO and founder of Millionaire Mindset Mastery and certified hypnotherapist Abi Levine to talk about the physics behind manifestation, and how to shift your mindset around your business, your money, and yourself. 💌 Want to get all of Tara’s resources? Subscribe: https://www.morningbrew.com/bossy-show/subscribe  Get More BOSSYWatch BOSSY on YouTube: www.youtube.com/@BOSSY_Show  Follow BOSSYInstagram: https://www.instagram.com/bossy_show/   TikTok: https://www.tiktok.com/@bossy_show Twitter: https://twitter.com/BOSSY_Show BOSSY, hosted by Tara Reed, brings you no-BS conversations about entrepreneurship, confidence, and leaning into your inner boss. Each episode, Tara puts on her boldest outfits and offers tactics and unapologetic advice – from the big names you love to the minds behind your favorite brands. New episodes drop on Thursdays – if you like the show, leave us a review and share with a friend!Learn more about your ad choices. Visit megaphone.fm/adchoices  Learn more about your ad choices. Visit megaphone.fm/adchoices
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Mar 20, 2025 • 36min

Getting Publicity for your Business with Cameo CEO Steven Galanis

In this episode, Tara talks with Cameo founder and CEO Steven Galanis about drumming up creative marketing campaigns, generating viral PR, and harnessing the inherent power of your brand in unique and attention-grabbing ways.💌 Want to get all of Tara’s resources? Subscribe: https://www.morningbrew.com/bossy-show/subscribe  Get More BOSSYWatch BOSSY on YouTube: www.youtube.com/@BOSSY_Show  Follow BOSSYInstagram: https://www.instagram.com/bossy_show/   TikTok: https://www.tiktok.com/@bossy_show Twitter: https://twitter.com/BOSSY_Show BOSSY, hosted by Tara Reed, brings you no-BS conversations about entrepreneurship, confidence, and leaning into your inner boss. Each episode, Tara puts on her boldest outfits and offers tactics and unapologetic advice – from the big names you love to the minds behind your favorite brands. New episodes drop on Thursdays – if you like the show, leave us a review and share with a friend!Learn more about your ad choices. Visit megaphone.fm/adchoices  Learn more about your ad choices. Visit megaphone.fm/adchoices
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Mar 13, 2025 • 40min

SoulCycle CEO: 21 Questions for a Boss (Choosing A Good Manager, Being Unlikable, and More)

Evelyn Webster, the dynamic CEO of SoulCycle, shares her journey of reviving the company after challenges and tough press. She discusses the fine balance of creativity and data in business, emphasizing how both can enhance success. Evelyn highlights the importance of mentorship and adaptability, particularly for women navigating career ambitions. She candidly reflects on the ethical dilemmas of leadership, prioritizing company values during tough decisions. The conversation rounds off with a fun dive into her favorite guilty pleasure films and SoulCycle's global expansion plans.
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Mar 6, 2025 • 38min

Dating as a Powerful Woman with Gabby Bernstein

In this episode, Tara catches up with Gabby Bernstein, author of the NYT bestseller 'Self Help: This Is Your Chance to Change Your Life' and host of the 'Dear Gabby' podcast. The ladies dive into the pros & cons of Tara's report card system (for work and in dating), why you should tell people what you really want and how to stop chasing unavailable partners.💌 Want to get all of Tara’s resources? Subscribe: https://www.morningbrew.com/bossy-show/subscribe  Get More BOSSYWatch BOSSY on YouTube: www.youtube.com/@BOSSY_Show  Follow BOSSYInstagram: https://www.instagram.com/bossy_show/   TikTok: https://www.tiktok.com/@bossy_show Twitter: https://twitter.com/BOSSY_Show BOSSY, hosted by Tara Reed, brings you no-BS conversations about entrepreneurship, confidence, and leaning into your inner boss. Each episode, Tara puts on her boldest outfits and offers tactics and unapologetic advice – from the big names you love to the minds behind your favorite brands. New episodes drop on Thursdays – if you like the show, leave us a review and share with a friend! Learn more about your ad choices. Visit megaphone.fm/adchoices
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Feb 27, 2025 • 36min

Rebecca Minkoff on Building a Fashion Empire, RHONY, and Owning Your Power

In this episode, Tara talks with founder and fashion designer Rebecca Minkoff to talk about the reality of being an entrepreneur and partner, the early mistakes she made in building her business, and why she worries that female leaders may be too victimizing of themselves.💌 Want to get all of Tara’s resources? Subscribe: https://www.morningbrew.com/bossy-show/subscribe  Get More BOSSYWatch BOSSY on YouTube: www.youtube.com/@BOSSY_Show  Follow BOSSYInstagram: https://www.instagram.com/bossy_show/   TikTok: https://www.tiktok.com/@bossy_show Twitter: https://twitter.com/BOSSY_Show BOSSY, hosted by Tara Reed, brings you no-BS conversations about entrepreneurship, confidence, and leaning into your inner boss. Each episode, Tara puts on her boldest outfits and offers tactics and unapologetic advice – from the big names you love to the minds behind your favorite brands. New episodes drop on Thursdays – if you like the show, leave us a review and share with a friend!Learn more about your ad choices. Visit megaphone.fm/adchoices Learn more about your ad choices. Visit megaphone.fm/adchoices
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Dec 19, 2024 • 34min

The Tea on Passive Income: Buying Real Estate When You’re Broke

Erika Brown is a real estate investor, agent, and serial entrepreneur who is working to close the wealth gap by teaching Black and Brown communities how to build a passive income by investing in property. In this episode, Tara and Erika discuss how much you actually need in order to start investing in real estate, and what they wish they’d known before starting to buy properties. 00:00 Intro00:15 “House Hacking”04:16 Good housing markets for multifamily homes09:25 What to consider when thinking about your cashflow numbers12:27 What Tara and Erika wish they’d known about being a real estate investor before they started buying properties19:29 How much money you actually need to start investing in real estate25:52 Why you should buy a home29:17 Advice for young entrepreneurs 💌 Want to get all of Tara’s resources? Subscribe: https://www.morningbrew.com/bossy-show/subscribe  Get More BOSSYWatch BOSSY on YouTube: www.youtube.com/@BOSSY_Show  Follow BOSSYInstagram: https://www.instagram.com/bossy_show/   TikTok: https://www.tiktok.com/@bossy_show Twitter: https://twitter.com/BOSSY_Show BOSSY, hosted by Tara Reed, brings you no-BS conversations about entrepreneurship, confidence, and leaning into your inner boss. Each episode, Tara puts on her boldest outfits and offers tactics and unapologetic advice – from the big names you love to the minds behind your favorite brands. New episodes drop on Thursdays – if you like the show, leave us a review and share with a friend!Learn more about your ad choices. Visit megaphone.fm/adchoices  Learn more about your ad choices. Visit megaphone.fm/adchoices

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