201. Building a Business in the Middle of Nowhere: Lessons from Alaska’s Off-Grid Mommy Sammy Cummings
The Rainmaker Family Show | Build Your Family Business
Release Date: 01/31/2025
219. Lauren ‘Lolly’ Anderson on Turning Creativity into Cash: The Power of Sugar Cookies
The Rainmaker Family Show | Build Your Family Business
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...
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218. From Care.com to AI: How Sheila Lirio Marcelo is Reimagining the Modern Family’s Time
The Rainmaker Family Show | Build Your Family Business
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...
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217. Adrienne Richardson on Burning It Down and Starting Over: A Raw Journey of Reinvention In The Midst of Uncertainty
The Rainmaker Family Show | Build Your Family Business
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...
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216. Amy Wine on Boundaries, Burnout, and Building a Life That Actually Works
The Rainmaker Family Show | Build Your Family Business
Hey Rainmakers! It’s Chelsey and Stephen here—and this conversation with Amy Wine is one we’ll be thinking about for a long time. Whether you’re juggling business, marriage, parenting, or all of the above (🙋♀️), Amy brings the wisdom, real-life experience, and clarity that makes you feel both seen and empowered. We’re talking about boundaries, burnout, and how to actually build a life that works—not just looks good from the outside. Amy’s story is one many of us can relate to. She scaled a successful counseling center to 7-figures in under a year... and nearly burned...
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215. Abundance Over Anxiety: How Danielle Schaaf Coaches Women to Think Bigger & Live Freely
The Rainmaker Family Show | Build Your Family Business
Hey Rainmakers! Chelsey and Stephen here, and today, we’ve got a powerhouse episode for you with the amazing Danielle Schaaf. If you’ve ever found yourself battling anxiety or feeling stuck in scarcity, this one’s for you. Danielle shares her journey from scarcity to abundance and how she now coaches women to embrace a mindset of possibility and power. Danielle opens up about her story—growing up in an environment where she was told she wasn’t enough, which led to years of feeling small and limited in what she could achieve. But everything changed when she started shifting her...
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214. Debt-Free & Unstuck: Jeremy Krulikowski on Breaking Financial Strongholds
The Rainmaker Family Show | Build Your Family Business
Hey Rainmakers! Stephen here, and today we’re tackling a topic that hits close to home for so many of us—debt and breaking free from its grip. In this episode, I’m joined by the incredible Jeremy Krulikowski, a debt expert, to talk about practical strategies for freeing yourself from financial strongholds. Whether you're drowning in debt or just want to make smarter financial moves, this episode is packed with actionable insights that could change everything. We kick things off by diving into some shocking stats on debt in America—credit card debt, personal loans, delinquencies, you...
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213. Built to Empower: How Cherie Hoeger Is Disrupting Period Care with Purpose
The Rainmaker Family Show | Build Your Family Business
Hey Rainmakers! It’s Chelsey and Stephen here—and if you’ve ever dreamed about launching a product that changes lives and makes a global impact, you’re going to love this episode. We sat down with Cherie Hoeger, founder of Saalt, a game-changing period care company that’s shaking up the industry with sustainable, empowering products—and purpose at the core. Cherie shares how a simple conversation with a family member in Venezuela opened her eyes to the global crisis of period poverty—and inspired her to take action. Her passion led her to launch Saalt, a B Corp that’s now found...
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212. Mastering the Pivot: Jennifer Jackson’s Journey in Building a Profitable Yoga Brand
The Rainmaker Family Show | Build Your Family Business
Hey Rainmakers! Chelsey and Stephen here, and today’s episode is all about what it really looks like to pivot, persevere, and profit. We sat down with one of our very own Mastermind members, Jennifer Jackson, to hear how she built a six-figure yoga brand—starting from scratch, solo, and with no personal yoga background. Yep, you read that right. Jennifer is a self-described dabbler turned determined entrepreneur. She’s done everything from real estate and affiliate marketing to crypto and product parties. But what changed the game for her was finally creating something...
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211. Turn Down The Noise, How To Quiet The Chaos in a Chronically Overstimulated World with Sarah Boyd
The Rainmaker Family Show | Build Your Family Business
Hey Rainmakers! Chelsey and Stephen here, and if you've ever found yourself—or your kiddos—melting down for no obvious reason, this episode is for you. We’re joined by our good friend and author Sarah Boyd to talk about something we’re all dealing with: overstimulation. Between the screens, the to-do lists, the noise (literal and mental), and everything else life throws our way, it’s easy to feel like your nervous system is stuck in overdrive. Sarah’s new book, Turn Down the Noise, is all about how to recognize overstimulation—not just in our kids, but in ourselves—and how to...
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210. How To Make Money Making Children's Books (& More) On Amazon, Even If You're Not An Author or Illustrator
The Rainmaker Family Show | Build Your Family Business
Hey Rainmakers! It’s Chelsey and Stephen, and if you’ve ever dreamed of writing a children’s book, creating a journal, or making money on Amazon without being a professional author or illustrator—this episode is your sign. We just launched our second children’s book (woohoo!) and wanted to share exactly how we did it, step by step, using Amazon KDP. This is hands-off income that ANYONE can do—yes, even you! In today’s convo, we break down the misconceptions that stop people from ever starting—like thinking you need to be creative, tech-savvy, or have a huge budget. Spoiler: you...
info_outlineHey Rainmakers! Chelsey and Stephen here, and today we’re bringing you an inspiring story from one of our Rainmaker community stars, Sammy Cummings. Sammy lives off-grid in Alaska, where she and her family have built a unique lifestyle centered around resilience, creativity, and entrepreneurship. She’s living proof that you can run a thriving online business no matter where you are—even if that’s near the North Pole!
In this episode, Sammy takes us through her journey from working in public relations to embracing the challenges of off-grid living while growing her Amazon business. From her “aha moment” of discovering dry bags as a niche product to navigating the hurdles of balancing family life, power outages, and limited resources, Sammy shows that anything is possible with the right mindset and determination.
Sammy also shares the power of Rainmaker strategies in helping her grow her brand, especially her Instagram account, Off Grid Mommy, which has skyrocketed to nearly 60,000 followers. She opens up about how she found her voice and leaned into her passions, creating content that resonates with families inspired by nature and adventure.
Whether you’re looking for tips on starting a business, building an audience, or simply staying motivated in tough seasons, Sammy’s story is packed with wisdom and encouragement. Don’t miss her advice on finding your “why” and staying focused, no matter where you are on your entrepreneurial journey.
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
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Watch The Million Dollar Mama Case Study:
https://www.makeitrainmomma.com/casestudy
Episode Minute by Minute:
- 0:00 - Introduction: Meet Sammy Cummings
- 2:15 - Living Off-Grid and Supporting Small Businesses
- 6:00 - From Public Relations to Rainmakers
- 9:45 - Sammy’s “Aha Moment” with Dry Bags
- 15:00 - Overcoming Financial Challenges and Mindset Shifts
- 20:00 - Growing Off Grid Mommy on Instagram
- 30:00 - Lessons Learned: Finding Your “Why”
- 38:00 - Final Thoughts and Encouragement