067: Why Not Me? Orly Zeewy on Female Entrepreneurship, the Bubble Wrap Story, and Redefining Failure

067: Why Not Me? Orly Zeewy on Female Entrepreneurship, the Bubble Wrap Story, and Redefining Failure

In this episode, Anne and Matt sit down with Orly Zeewy, brand strategist and author of the upcoming book Why NOT Me? The Female Guide for Entrepreneurship, to unpack the unique challenges women face when building a business. Orly shares the story of her book's title—born from the universal imposter syndrome of "Why me?"—and explains why female founders need to embrace failure as feedback rather than a reflection of their self-worth. They also explore the dangers of "ugly babies" in business, including the surprising origins of bubble wrap. The group discusses why over-coaching can paralyze your progress and the flawed pricing mentalities that hold so many female entrepreneurs back. Whether you are navigating product-market fit or learning how to stand firmly in your zone of genius, this conversation is a masterclass in pivoting with purpose and finding your community. 🚨 Stuff You’ll Want to Remember: * "Perfection is the enemy of good. This is what I hear from women all the time." — Orly * "Do not let coaching stall the doing." — Anne * "Failure is the whole, is the backbone of entrepreneurship. Because if you don't fail, you don't grow." — Orly * "Just because it comes easily to you does not mean it has no value." — Orly 📡 Where to Find Us * Orly Zeewy → Zeewy Brands [https://zeewybrands.com] - LinkedIn [https://www.linkedin.com/in/orlyzeewy] * Anne → Fix & Form [https://fixandform.com/] - LinkedIn [https://www.linkedin.com/in/annegillaspie/] * Matt → ChipBot [https://getchipbot.com/] - LinkedIn [https://www.linkedin.com/in/mattlo/]

066: Is AI Killing SaaS? The Builder Bug and Why Execution Beats Planning

In this episode, Matt and Anne dive deep into the rapidly shifting landscape of software development and how AI is empowering non-technical founders to build their own bespoke solutions. They discuss the current headwinds facing the SaaS market , the addictive nature of the "builder bug" , and why relying on common sense and Standard Operating Procedures (SOPs) can bridge the coding experience gap. Finally, they explore the ultimate dividing line in business today: why those who execute and ship quickly will outpace those who get stuck in endless loops of overthinking and planning. 🚨 Stuff You’ll Want to Remember: * "For the folks that know what they're doing, AI is is an accelerator. And for the folks that have no no idea, AI is a detriment to their future." — Matt * "At the core minimum, you need common sense to build up the experience gap that you have." — Matt * "Don't let coaching stall the doing... you don't need coaching. You don't need more thinking. You need to just go do and go execute." — Anne * "That information value is gone now. So what is remaining? Your ability to execute." — Matt 📡 Where to Find Us * Anne → Fix & Form [https://fixandform.com/] - LinkedIn [https://www.linkedin.com/in/annegillaspie/] * Matt → ChipBot [https://getchipbot.com/] - LinkedIn [https://www.linkedin.com/in/mattlo/]

065: The Real Silver Tsunami, AI Mentorship, and the Future Workforce

In this episode, Matt and Anne debate the looming impact of the "silver tsunami" and what it actually means for the future of business and the workforce. While Anne argues that older generations provide irreplaceable human mentorship, culture, and relationship-building skills that AI cannot replicate, Matt contends that task-based AI tools and video tutorials are already replacing the need for traditional corporate guidance. They explore whether the real generational business opportunity lies with the tech-savvy, well-capitalized 45-to-55 demographic, and how declining birth rates will force a massive shift in corporate productivity over the next two decades. Oh, and they also compare their coffee routines and how they use caffeine for peak productivity versus socializing. 🚨 Stuff You’ll Want to Remember: * "The generation between 45 and 55. In my opinion, that's the silver tsunami wave..." — Matt * "What you can't get when you type in a prompt to AI... is the mentorship from a human being that has personal stories and lived experiences." — Anne * "I argue that promotions and excelling in your career happens from relationship building skills, which I don't believe you can learn on AI." — Anne * "It's not exiting, there's less people entering. That's actually more scarier than the people exiting." — Matt 📡 Where to Find Us  * Anne → Fix & Form [https://fixandform.com/] - LinkedIn [https://www.linkedin.com/in/annegillaspie/]  * Matt → ChipBot [https://getchipbot.com/] - LinkedIn [https://www.linkedin.com/in/mattlo/]

064: Battle Wounds and Boardrooms: Mojo's Evolution from Solo Hustler to Production Agency CEO

In this inspiring episode, Anne and Matt are joined live from Los Angeles by Mojo, the founder and executive producer of Rainbow Creative. Mojo opens up about his incredible founder's journey, tracing his roots from customer service at Apple and marketing at Disney to launching coworking spaces for WeWork during their hyper-growth phase. He shares the raw truth about the physical and mental toll of scaling a mission-driven podcast agency to 25 shows while surviving on just four hours of sleep a night. Realizing he couldn't do it all, Mojo breaks down his crucial pivot to hiring a CFO, embracing executive coaching, and learning the true mechanics of profit and sustainable growth. Packed with lessons on leveraging your Rolodex as an "unfair advantage," this episode is a masterclass in rebounding from setbacks, owning your role as a true CEO, and leading with radical empathy. 🚨 Stuff You’ll Want to Remember: * "What's a 10 in your life? Imagine if that's a 1—how do you make that into a 10? That 10, I try to make into another 10." — Mojo * "...failing is, is an end successes are just metrics on a line." — Matt  📡 Where to Find Us * Mojo → Rainbow Creative [https://www.rainbowcreative.co/] - Instagram [https://www.instagram.com/mojorainbow] * Anne → Fix & Form [https://fixandform.com/] - LinkedIn [https://www.linkedin.com/in/annegillaspie/] * Matt → ChipBot [https://getchipbot.com/] - LinkedIn [https://www.linkedin.com/in/mattlo/]

063: The Power of Experience, Adapting to AI, and Building Your Next Chapter with Adrienne Arieff

In this episode, Anne and Matt sit down with PR veteran and brand strategist Adrienne Arieff to discuss her journey from running a successful firm for a decade to launching a brand-new, mission-driven venture. Adrienne gets real about the harsh realities of industry shifts and job loss, sharing why she firmly believes that age and experience are actually professional superpowers rather than liabilities. The group dives into how Adrienne successfully integrated AI into her consulting workflow to stay highly competitive, the compounding value of a strong professional network, and she gives an exclusive first look at her "Next Chapter Shift" program—an eight-week cohort designed to help midlife women navigate major personal and professional transitions to build their ultimate "life resume." 🚨 Stuff You’ll Want to Remember: * "If you're coming from a place of fear, you are not going to be as creative and you are certainly not going to be as productive." — Adrienne * "The older you are, I do feel that you have the ability to say no comfortably, which allows you to filter out the things that you are more aligned on." — Anne  * "Anytime you're going zero to one, it's impossible to figure out where you're going in one year anyway, right? Because you don't even know if your hypothesis is right." — Matt 📡 Where to Find Us * Anne → Fix & Form [https://fixandform.com/] - LinkedIn [https://www.linkedin.com/in/annegillaspie/] * Matt → ChipBot [https://getchipbot.com/] - LinkedIn [https://www.linkedin.com/in/mattlo/] * Adrienne → Instagram [https://www.instagram.com/next_chapter_collective_/] - YouTube [https://www.youtube.com/@NextChapter_Collective]