Hey Rainmakers! Chelsey and Stephen here, and this episode is just plain sweet—literally. 🍪 We’re talking with Lauren “Lolly” Anderson, the creator behind Lolly’s Home Kitchen, who went from corporate life to cashing in on her creativity with sugar cookies that are not only gorgeous but totally profitable. If you’ve ever wondered if your passion project could actually make money—this one’s for you.

Lolly shares the real story of how a holiday hobby turned into a business that lets her work from home, bless her family financially, and teach others to do the same. What started with decorated cookies for friends and family quickly became a word-of-mouth hit, and before she knew it, she had more orders than time. That’s when she realized—this wasn’t just baking. It was business.

We talk about pricing with confidence, the mindset shifts required to charge what you’re worth, and how important it is to set boundaries (especially when friends start asking for freebies!). Lolly also opens up about teaching other women to start their own cookie businesses and how empowering it’s been to watch them unlock a new level of confidence and income.

This episode is a masterclass in turning your creativity into cash—and it’s so much more than just cookies. If you’ve ever had a spark of an idea, a creative outlet you love, or a dream of doing something from home that actually works—Lolly’s story will light a fire in you.

Connect with us:

► Rainmaker Instagram: @therainmakerfamily

► Chelsey Instagram: @chels_diaz

► Stephen Instagram: @steezdiaz

► TikTok: @therainmakerfamily

► Facebook: @diazfamilylegacy

► Website: therainmakerfamily.com

Join Our Next Rainmaker Challenge - How To Make Passive Income From Home: https://therainmakerchallenge.com

Save On Our Favorite Things:

https://rainmakerfamily.com/deals

Watch The Million Dollar Mama Case Study:

https://www.makeitrainmomma.com/casestudy

Episode Minute by Minute:

• 0:00 - Meet Lauren “Lolly” Anderson of Lolly’s Home Kitchen
• 2:00 - From Corporate Life to Cookie Biz
  5:30 - Turning a Hobby into a Legit Business
• 9:00 - Pricing Confidently and Charging What You’re Worth
• 12:00 - Setting Boundaries When Everyone Wants a Favor
• 16:30 - Teaching Others to Build Cookie Businesses
• 21:00 - The Power of Belief, Consistency, and Showing Up
• 24:00 - Final Encouragement for Creative Entrepreneurs
  
  

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:

► Rainmaker Instagram: @therainmakerfamily

► Chelsey Instagram: @chels_diaz

► Stephen Instagram: @steezdiaz

► TikTok: @therainmakerfamily

► Facebook: @diazfamilylegacy

► Website: therainmakerfamily.com

Join Our Next Rainmaker Challenge - How To Make Passive Income From Home: https://therainmakerchallenge.com

Save On Our Favorite Things: https://rainmakerfamily.com/deals

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

Hey Rainmakers! Chelsey and Stephen here—and today’s episode is a powerful one. We’re sitting down with our friend Adrienne Richardson, who’s been a force in the marketing world for years. But instead of talking Facebook ads or funnels, Adrienne takes us behind the scenes of one of the most raw, real, and faith-led reinventions we’ve ever heard.

What do you do when everything you’ve built—the business, the team, the income—stops feeling right? Not because it's failing, but because deep down, you know you're being called to something else. That’s exactly where Adrienne found herself in 2024, and in this conversation, she shares what it looked like to shut down her successful membership, let go of her team, and start from scratch with no plan—just obedience and a whole lot of faith.

We talk about the tension of knowing something needs to change but having no clarity yet, how fear and peace can coexist, and the importance of listening to those subtle nudges before they become deafening. Adrienne’s honesty about the emotional toll, the decision to let people go, and the freedom that followed is going to speak directly to your heart—especially if you’re in a season of transition or reinvention.

If you've ever felt like you’ve outgrown a version of your life or business, or you're quietly wondering, "What’s next for me?"—this episode is your permission slip to explore the unknown. Adrienne doesn’t just share what it’s like to burn it all down—she shares how to do it with courage, clarity, and a deep trust in what’s next.

Connect with us:

► Rainmaker Instagram: @therainmakerfamily

► Chelsey Instagram: @chels_diaz

► Stephen Instagram: @steezdiaz

► TikTok: @therainmakerfamily

► Facebook: @diazfamilylegacy

► Website: therainmakerfamily.com

Join Our Next Rainmaker Challenge - How To Make Passive Income From Home: https://therainmakerchallenge.com

Save On Our Favorite Things:

https://rainmakerfamily.com/deals

Watch The Million Dollar Mama Case Study:

https://www.makeitrainmomma.com/casestudy

Episode Minute by Minute:

• 0:00 - Welcome Adrienne Richardson & Setting the Stage
• 1:30 - When Everything Stops Working: The Quiet Unraveling
• 4:00 - Getting Clarity Through Obedience, Not Control
• 7:00 - Canceling the Biggest Launch & Trusting the Process
• 11:00 - Fear, Provision, and Letting Go of the Membership
• 14:00 - Shutting Down the Entire Business: Adrienne’s Bold Leap
• 17:00 - Letting Go of Team with Compassion and Faith
• 21:00 - Wrestling with People-Pleasing and Outside Pressure
• 27:00 - Rediscovering Yourself After Years of Being Small
• 33:00 - The Power of Starting Over and What’s Next for Adrienne