Libsyn Directory

216. Amy Wine on Boundaries, Burnout, and Building a Life That Actually Works

The Rainmaker Family Show | Build Your Family Business

Release Date: 05/16/2025

221. The Rainmaker AI Toolkit: Our Favorite AI Tools for Time Freedom and Creativity

The Rainmaker Family Show | Build Your Family Business

Hey Rainmakers—it’s Stephen here, and this episode is straight fire if you’re ready to boost your productivity and creativity using AI. I’m pulling back the curtain on the tools Chelsey and I are actually using in our business right now. From designing in Canva to writing podcast titles in seconds, this toolkit is stacked with resources that are saving us time and unlocking new creative energy. I’m joined by our Rainmaker marketing assistant Sophie, and we’re walking through each AI tool we love—plus how we’re using them. You’ll get a real look into our process and how you...

220. Embracing the CEO Mindset with Amber McCue: Strategies for Time Freedom and Business Success

The Rainmaker Family Show | Build Your Family Business

Hey Rainmakers! Chelsey and Stephen here—and if you’ve ever felt like your business is running you instead of the other way around, this one’s for you. We’re joined by the incredible Amber McCue, a systems queen, time freedom strategist, and all-around business powerhouse. This episode is all about reclaiming your role as the CEO—not just in your biz, but in your life. Amber shares how she helps entrepreneurs move from reactive to intentional, even when life is full and the calendar feels packed. She breaks down her signature "Planathon" system and how it helps business owners...

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...

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...

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...

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...

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...

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...

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...

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...

More Episodes

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 out doing it. Eventually, she made the bold decision to sell that business and go all in on the kind of life and coaching that aligns with her values. In this episode, she shares how that decision impacted her marriage, what it looked like to honor her season of life, and how she navigated being the “entrepreneurial one” while married to someone who isn’t wired the same way.

One of our favorite moments was when Amy broke down how to have consistent, life-giving communication with your spouse—especially when you feel like you're living in two different worlds. She gives practical advice for regular check-ins, owning your own growth areas, and getting real about your season so you can stop trying to do everything at once.

If you’re tired of overcommitting, feeling disconnected, or trying to force balance in a season that demands boundaries, Amy’s perspective is exactly what you need. From creating margin for your family, to setting limits with love, to redefining success on your own terms—this is the conversation we all need right now.

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► Website: therainmakerfamily.com

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Episode Minute by Minute:

0:00 - Meet Amy Wine: From Counselor to Coach
2:00 - Amy’s Journey into Entrepreneurship
5:30 - Scaling Fast & Burning Out
7:00 - Navigating Business and Marriage with Opposite Mindsets
12:00 - The Thrive in Life Inventory & Knowing Your Season
16:00 - Weekly Marriage Sync Meetings: Why They Matter
20:00 - Saying No to Good Things for the Right Reasons
24:30 - The Pig Story: Boundaries with Kids (and Yourself)
30:00 - When Friends Don’t Understand Your Boundaries
32:00 - Final Thoughts on Ownership, Growth & Letting Go of Guilt

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