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

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This episode is 22 minutes long.

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This episode was published on September 4, 2025.

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from BOSSY · host Morning Brew

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. Help BOSSY get to know you better! Take this quick survey so we can keep building the best show we can for you: ⁠https://www.morningbrewbreakroom.com/c/r/Bossy-Survey?Platform=pod⁠ 💌 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

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