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June 24, 2025

Episode 222 – Chelsey and Stephen Diaz – The Rainmaker Family, Creating a Thriving Family Legacy

“That’s the beautiful thing about entrepreneurship, is the way that it creates impact, not only in your finances, but in that overflow of who you are and how you show up for yourself and the ones that you love, your family.” – Chelsey Diaz


 
  • Meet Chelsey and Stephen Diaz, the dynamic founders of The Rainmaker Family, dedicated to guiding families towards financial abundance and time freedom so they can leave a thriving family legacy. Taking a bold step in 2017, they shifted from a service-based wedding photography business where they were trading dollars for hours to go all in online passive income opportunity. Now they focus on empowering moms to use the same method they developed to become RAINMAKERS for their own families.
  • Specializing in e-commerce and building brands, the Diaz duo champions the idea of “buying back time,” enabling moms in their community to run successful 6 and 7-figure businesses while cherishing moments with loved ones. In their Rainmaker Mastermind program, Chelsey and Stephen guide entrepreneurs in building, scaling, and then selling an Amazon business. Ranked #148 on the Inc 5000 list, and #2 in the category of education, these two are reshaping online learning, proving that success in business can coexist harmoniously with a family-first approach.
  • Listen in to hear Chelsey and Stephen’s story of how they got involved in this unexpected adventure that began with the “Spaghetti Years.” Culminating in 2019 – 2020 when their wedding business effectively vanished and their e-commerce businesses flourished, Chelsey and Stephen went all-in on their new entrepreneurial path knowing there was no magic pill or overnight success, but driven by their mutual vision for their future. In this episode they talk about the complementary superpowers they each contribute to their organization and share stories about the obstacles and fears they have overcome along the way. Keeping intententional team culture at the forefront has allowed them to spend more time with their family, knowing that their leaders and team will rise to the occasion and elevate it! At the heart of it all is to be of contribution, empowering their community of entrepreneurs, with a focus on moms, to reacquaint them with their identity and become RAINMAKERS for their families.
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  • Show Notes
  • [00:42] Patrick introduces his next TEDM guests Chelsey and Stephen Diaz.
  • [02:11] Chelsey, Stephen, and Patrick breeze into their conversation as Stephen describes what he and Chelsey do in the e-commerce space and Chelsey shares the story of how they got involved in this unexpected adventure they call the Spaghetti Years.
  • [09:06] Let’s talk timeline. Stephen provides the run down on their timeline from starting their e-commerce business to the point where that income matched their wedding photography business, which also allowed them to start a third income stream in the education space. It culminated during 2019 – 2020 which saw their wedding business effectively vanish and their e-commerce businesses flourish.
  • [12:12] The upfront investment for an e-commerce business varies, but Stephen offers a good range to consider, and both he and Chelsey stress the importance of education before diving in. Like real estate, Amazon can be a complicated venture and working with a mentor makes all the difference.
  • [14:12] Amazon provides many ways to make money, and Stephen paints the big picture of the business model he and Chelsey operate within. He uses the analogy of a grocery store to explain how the method works and how they train their families.
  • [18:04] Complementary superpowers have been a winning combo for Chelsey and Stephen and Chelsey walks us through some of the heavy lifting they did to get the flywheel going into a successful business venture. Although never “passive” income, once up and running it requires a bit less maintenance.
  • [20:53] Stephen and Chelsey explain the type and amount of product they typically see their students sell and the need to approach building this business strategically.
  • [22:45] What sort of skillsets and strengths are beneficial to building a successful e-commerce business? It’s an entrepreneurial journey without a doubt and certainly no magic pill or overnight success. It takes work and drive.
  • [27:13] At the heart of the entrepreneurial journey beats the magic of community.
  • [27:58] Nature or nurture. When it comes to their entrepreneurial chops, Chelsey and Stephen had a different trajectory throughout school and their early careers, and each tackled their unique fears. Chelsey talks about her lower risk tolerance – a muscle that she is steadily building! Stephen shares a story that highlights the strength they found in working together toward their individual yet very similar vision.
  • [33:44] Mutual values create the rock steady foundation. Chelsey and Stephen lay out the lessons they’ve learned along their business path so far. Life season, grace, and differences are the big rocks.
  • [38:58] Creating the right culture and taking a stand for it creates stronger leadership and a rock star team. Chelsey and Stephen learned that when they took 1 or 2 months off with the arrival of their babies. The team not only rose to the occasion but hit it out of the park, which forced them to level up when they came back. They’ve decided this is their new business strategy – to just keep having babies!
  • [40:53] The Rainmaker Family – how did that name come about? Using a garden analogy, Stephen illustrates how its come to have deeper meaning for them and their students, the more they dig into it. It’s become an anchor to help the moms they work with, to get reacquainted with their identity and their power.
  • [44:38] Side hustle or full-on business? Stephen shares what they observe people using it for and how much time you can expect to invest.
  • [46:24] Looking forward. Chelsey and Stephen discuss how they’re viewing the future and what training they’re undertaking as leaders. It’s a ever-learning process and so important to keep growing.
  • [49:06] The dynamic duo – Stephen shares the individual superpowers they each contribute to their organization and Chelsey explains how intentional they’ve become with this season of their life.
  • [52:32] Stephen explains the structure and make-up of their team.
  • [53:19] Fork in the road moments. Stephen breaks down the obstacles they’ve needed to overcome to get to this point and how the obstacles became a pivotal part of their growth.
  • [56:05] Patrick recognizes Chelsey and Stephen for their winning formula of building their confidence over time, sometimes even borrowing it from others, to continue moving forward, upleveling and honing their business muscles.
  • [57:50] Golden nuggets of wisdom from Chelsey in transformation through entrepreneurship, and a personal observation of the entrepreneurial journey from Stephen.
  • [60:50] You got this! Believe in yourself and intentionally decide who you need to become and how you want to show up to achieve the goal and vision you’ve set out. At times this requires repositioning and refocus. Chelsey reflects on how they view this within themselves and each other.
  • [66:59] Winding down into the rapid fire for two! Apple or Android (with a backstory); Stephen’s favourite movie types; music made by the kids’ selections; message at the pearly gates; impactful books.
  • [71:33] Chelsey and Stephen’s gratitude.
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    Episode 222 – Chelsey and Stephen Diaz – The Rainmaker Family, Creating a Thriving Family Legacy
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