218. From Care.com to AI: How Sheila Lirio Marcelo is Reimagining the Modern Family’s Time

Hey Rainmakers! Chelsey and Stephen here—and this conversation is a game-changer. If you’ve ever juggled childcare, business, and the never-ending to-do list, this episode is going to hit home. We’re joined by Sheila Lirio Marcelo, the brilliant founder of Care.com and now co-founder of Proof of Learn—where she’s leveraging AI to reimagine how families function in today’s fast-paced world.

Sheila’s journey from needing childcare help as a young mom in law school to building a billion-dollar solution is nothing short of inspiring. But what’s even more powerful is the next chapter she’s writing—one where technology doesn’t replace human connection, but enhances it. We dive deep into how AI, blockchain, and learning platforms like Proof of Learn are equipping families with more freedom, more leverage, and more possibility.

This conversation covers everything from entrepreneurship as a mom, to the emotional toll of leadership, to what it looks like to make bold pivots later in your career. Sheila shares how she learned to delegate, how she created boundaries to protect her family time, and what she’s most excited about building next.

If you’ve ever felt like you're drowning in logistics—or you dream about what’s possible when families have more time—this episode is for you. You’ll walk away encouraged, inspired, and reminded that with the right support, your vision for family + business can thrive.

Connect with us:

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► Chelsey Instagram: @chels_diaz

► Stephen Instagram: @steezdiaz

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► Facebook: @diazfamilylegacy

► Website: therainmakerfamily.com

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Watch The Million Dollar Mama Case Study: https://www.makeitrainmomma.com/casestudy

Episode Minute by Minute:

• 0:00 - Welcome Sheila Lirio Marcelo!
• 1:30 - Sheila’s Origin Story: From Law School Mom to Tech CEO
• 4:00 - How Care.com Was Born from a Personal Need
• 8:00 - Learning to Delegate and Protect Family Time
• 12:00 - From Care.com to AI: The Vision for Proof of Learn
• 16:00 - What Families Really Need in the Next Generation
• 20:00 - Embracing Big Pivots and Being Okay with Uncertainty
• 24:00 - The Intersection of Tech, Education, and Family
• 28:00 - Final Words on Courage, Calling, and Innovation