Leap Academy with Ilana Golan

Episode 140: Care.com Founder Sheila Lirio Marcelo: How a Struggling Mom Built a Million Dollar Caregiving Empire

Date: January 13, 2026
Guest: Sheila Lirio Marcelo
Host: Ilana Golan

Overview

In this inspiring episode, Ilana Golan sits down with Sheila Lirio Marcelo, the formidable founder of Care.com, to uncover how Sheila’s unconventional journey as a young mother, immigrant, and generalist led her to disrupt the caregiving industry. Sheila shares not only the untold emotional realities of her path—from hiding her motherhood in her early career to building and scaling one of the world’s largest care marketplaces, taking it public, and later reinventing herself with a new AI startup—but also concrete, actionable lessons on leadership, entrepreneurial risk-taking, and embracing one’s whole self.

The discussion ranges from formative childhood experiences in the Philippines, through Silicon Valley startup challenges, to the role of meditation and mindset in resilience and reinvention. Listeners will find a mix of candid career truths, “mic drop” wisdom, and practical insights for anyone seeking to leap into new opportunities or navigate major transformation.

Key Discussion Points & Insights

1. Early Life, Identity & Formative Experiences

Timestamp: 02:29 – 06:43

• Sheila was raised in the Philippines in a matriarchal family, with a strong, ambitious mother and nurturing father, plus five siblings. This upbringing, free from gender stereotypes, made her comfortable expressing both “feminine and masculine” qualities.
  • “I feel like as a leader, I embody both the feminine and the masculine in a comfortable way.” (Sheila, 03:36)
• Her family sent her and her younger brother to a provincial Catholic school to save money and reconnect with their language and roots.
  • “That year taught me a lot. Not just the language—it also gave me a sense of respect and understanding of the Filipino culture.” (Sheila, 04:44)
• She learned early compassion through firsthand exposure to kids of all backgrounds.
  • “When you’re a child and you’re just playing on the street together… everybody’s equal.” (Sheila, 06:19)

2. Navigating College, Early Career & Motherhood

Timestamp: 06:43 – 11:20

• Sheila attended Mount Holyoke and became a mother while in school, hiding her parental status in early job interviews out of fear of judgment.
  • “I hid the fact that I was a young mom because I felt I was gonna get judged. I couldn’t be my whole self.” (Sheila, 07:19 / also 00:00)
• As the main breadwinner, she juggled high professional expectations with parenting, struggling with guilt and trying to “power through” with little sleep.
• A health crisis in her twenties (after a grueling travel schedule) was a turning point, leading her to discover meditation and invest in stress management.
  • “That’s when I started meditating. It helped me really settle my mind…starting to address expectation of perfection.” (Sheila, 10:07 – 10:53)

3. Mentors, Reinvention & Building for Impact

Timestamp: 11:20 – 18:16

• Critical feedback from mentors (“no one likes working with you”) and sponsorship led Sheila to pursue deep self-work, journaling, and executive coaching—ushering in a new phase of leadership growth.
  • “You’ve got to get out of your own way and you’ve got to figure this out…You’ve got a lot that you’ve got to shed.” (Sheila quoting mentors, 12:33)
• Her career evolved from consulting and working on marketplaces to entrepreneurship; her broad, generalist skillset set the stage for Care.com.
  • “It was actually that breadth that made you a better leader...the generalist is what created Sheila and Care.com, right?” (Ilana, 14:57)
• Sheila encourages others to embrace the generalist mindset, focus on problem-solving, and avoid pigeonholing self or others.
  • “If you pigeonhole yourself, you limit yourself. But you also do that to other people when you lead.” (Sheila, 16:58)

4. Starting Care.com – Risks, Experiments, and Market Strategy

Timestamp: 18:16 – 28:07

• Sheila confronted societal bias and skepticism for launching a “female-centric” business rather than a flashier, male-dominated tech startup.
  • “It was more the insecurity that I was going to be judged to start a company that was female focused and female centric…” (Sheila, 18:36)
• A defining mentor conversation forced her to choose between solving “consumer pain” (her true calling) and more glamorous ventures.
  • “My mentor is like, is that really who you are? Is this really what you want to be doing?” (Sheila, 19:55)
• The early days were marked by running rapid, lean experiments to validate the concept and market need, using Craigslist and early Google AdWords.
  • “Key things I will say is…we need to run small, fast experiments for us to test the idea…” (Sheila, 22:15)
• Her approach emphasized balancing passion for the problem (not the solution) with objectivity, iterating based on data and maintaining flexibility.

5. Building a Two-Sided Marketplace & Overcoming Early Challenges

Timestamp: 25:49 – 31:11

• Care.com tackled the complex challenge of building trust in the caregiving market, focusing on background checks and rigorous vetting from day one.
  • “We background checked every caregiver since the launch of the company, and no one had done that.” (Sheila, 29:42)
• Success depended on being intensely data-driven about liquidity: their central KPI was the caregiver-to-family ratio per zip code—pushing relentlessly until they hit “the number.”
  • “Identify your bullseye, keep testing and make sure that’s your bullseye, build a product towards that bullseye…” (Sheila, 27:08)
• Timing was crucial; the market’s readiness played as big a role as product features.

6. Scaling, IPO, and Founder Resilience

Timestamp: 31:11 – 35:02

• Sheila guided Care.com through massive scaling, three acquisitions, and an IPO—driven by the dream of making caregiving a public good.
  • “I really wanted the caregivers and families to get a chance to own care.com.” (Sheila, 31:57)
• A strong, aligned co-founding team was essential for weathering the pressure, and Sheila recommends founders intentionally build that support system.
  • “I often coach people who start companies to have an incredible co-founding group…” (Sheila, 34:08)
• Despite strong advisors and co-founders, the journey of founding, scaling, running a public company, parenting, and holding a marriage together was “a lot.”

7. Reinvention: Sabbatical, Joy, and New Ventures

Timestamp: 35:02 – 37:55

• After exiting Care.com, Sheila intentionally paused to rediscover her purpose rather than chase more money or prestige.
  • “I definitely went through the importance of the pause…and really regrouping from myself. What did I want to do?” (Sheila, 35:30)
• Her “third chapter” emerged from self-discovery, creativity (even design and drawing), and the realization that her joy lay in building meaningful solutions for families.

8. OHAI AI: New Chapter in AI-Powered Family Care

Timestamp: 40:40 – 42:54

• Ohai AI, Sheila’s latest startup, is an “AI power household assistant” meant to alleviate parents’ mental load by syncing schedules, reminders, and communications.
  • “You tell us all the apps you use, the craziness of your world, and we will summarize it for you…make it easy for you on your calendar every week…” (Sheila, 41:00)
• The product is rooted in Sheila’s lifelong empathy for families and real-life pain points (now including her grandmother-hood).

9. Mindset, Meditation, and Enduring the Journey

Timestamp: 42:54 – 46:55

• Sheila credits transcendental meditation (twice daily) as a cornerstone of her resilience, allowing her to witness thoughts without judgment and better handle entrepreneurial and personal setbacks.
  • “You’re really doing every day is cleansing your thoughts so that you start to say, I am not my thoughts.” (Sheila, 43:55)
• She describes a progressive “awakening”—each challenge (illness, feedback, parenting poignancy) led her to deeper clarity, truth, and calm.
  • “I think sometimes pain and suffering is what brings you and the challenges you’ve been asking me about—challenge is what then really awakens you.” (Sheila, 48:24)

10. Advice for Reinventors & Final Wisdom

Timestamp: 49:17 – 52:06

• “There’s a feeling of victimhood, and we feel alone…but in reality, we’re all human. We all, oh my gosh, I’ve had so many challenges, and it is part of us being human.” (Sheila, 49:29)
• She urges listeners to remember:
  • “Five years from now, am I really going to be stressed about sweating this small thing that I think is the sky is falling and is the biggest problem in the world?”
    (Sheila, 49:56)
  • Find the paradoxical humility: “How do you feel special, but yet live life with a humility of ordinary…a sense of knowing that everyone is special. And that comparison is…the thief of joy.” (Sheila, 50:43)

Notable Quotes & Memorable Moments

• “You gotta have the inner drive to push, push, push an idea to see the light of day. But you also have to be dispassionate and objective enough to look at the data.”
  (Sheila, 22:20)

• “If you pigeonhole yourself, you limit yourself. But you also do that to other people when you lead.”
  (Sheila, 16:58)

• “My mantra is: trust and love and live in joy.”
  (Sheila, 46:20)

• “How do you feel special, but yet live life with a humility of ordinary…that’s what makes us ordinary. And I think when you start adopting that, you start to realize…I don’t know everything. I can learn from everybody.”
  (Sheila, 50:40–51:30)

• Alana (mic drop): “That was a mic drop, Sheila. That is so, so, so, so good.”
  (52:06)

Timestamps for Important Segments

• Childhood and Cultural Identity: 02:29–06:43
• Motherhood and Early Career Struggles: 06:43–11:20
• Mentors and Leadership Self-Discovery: 11:20–18:16
• Launching Care.com & Market Validation: 18:16–28:07
• Marketplace Challenges & Data Focus: 25:49–31:11
• IPO & Co-Founders: 31:11–35:02
• Post-Care.com Reinvention: 35:02–37:55
• Ohai AI – New Venture: 40:40–42:54
• Meditation & Mindset: 42:54–46:55
• Advice to the Younger Self / Final Wisdom: 49:17–52:06

Closing Thoughts

Sheila Lirio Marcelo’s story is a rare blend of vulnerability and actionable insight, showing listeners that the journey to purposeful impact is never linear and never easy—but always, with persistence, self-inquiry, and service, possible. Whether you are a struggling founder, parent, or career leaper, you’ll find not just inspiration but concrete next steps in how Sheila bridges passion and objectivity, ambition and humility, achievement and self-care.

To learn more or connect:

• Ohai AI
• Instagram: @sheilaliriomarcelo
• LinkedIn: Sheila Lirio Marcelo

Listen, share, and leap.