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067: Why Not Me? Orly Zeewy on Female Entrepreneurship, the Bubble Wrap Story, and Redefining Failure
Mar 24, 2026
37m 05s
066: Is AI Killing SaaS? The Builder Bug and Why Execution Beats Planning
Mar 19, 2026
42m 32s
065: The Real Silver Tsunami, AI Mentorship, and the Future Workforce
Mar 17, 2026
25m 16s
064: Battle Wounds and Boardrooms: Mojo's Evolution from Solo Hustler to Production Agency CEO
Mar 12, 2026
32m 17s
063: The Power of Experience, Adapting to AI, and Building Your Next Chapter with Adrienne Arieff
Mar 10, 2026
48m 47s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 3/24/26 | ![]() 067: Why Not Me? Orly Zeewy on Female Entrepreneurship, the Bubble Wrap Story, and Redefining Failure✨ | female entrepreneurshipimposter syndrome+3 | Orly Zeewy | Why NOT Me? The Female Guide for Entrepreneurship | — | female foundersentrepreneurship+3 | — | 37m 05s | |
| 3/19/26 | ![]() 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 s... | 42m 32s | ||||||
| 3/17/26 | ![]() 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... | 25m 16s | ||||||
| 3/12/26 | ![]() 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... | 32m 17s | ||||||
| 3/10/26 | ![]() 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 ... | 48m 47s | ||||||
| 3/5/26 | ![]() 062: The 2-Month Go-to-Market Cycle, AI Coding Tools, and Why "Live" is the New SEO | In this episode, Matt and Anne dive into how AI is drastically accelerating the founder's journey, cutting the traditional six-month software go-to-market cycle down to just two months. Matt shares his insights on using AI tools to build a fully functional MVP in mere weeks, shifting a founder's focus from heavy development to rapid distribution. They also explore the changing landscape of SEO in the age of AI search and why showing up "live" to interact with your audience is becoming the ult... | 31m 25s | ||||||
| 3/5/26 | ![]() 061: Vanity Metrics vs. Reality: The Ethics of Buying Followers and Beating the Algorithm | In this episode, Matt and Anne tackle the murky world of social media vanity metrics, debating whether a high follower count is a valuable business asset or just a digital mirage. Anne shares her temptation to artificially inflate her audience to serve as a resume for her speaking career, while Matt strongly cautions against the ethical and algorithmic consequences of buying bot followers. They also explore the strategic differences between B2B and personal branding, why boosting top-performi... | 22m 58s | ||||||
| 2/26/26 | ![]() 060: The Work-Life Boundary: Why Your Business Shouldn't Be Your Family | Matt and Anne kick off this episode debating the merits of the "mental health day" versus the classic grit of powering through an illness. Anne shares her philosophy on working intuitively and trusting your energy to get tasks done faster , while Matt questions how that fluidity applies to the rigid demands of a startup. The conversation then takes a sharp turn into the realities of leadership and control. Matt passionately explains why he believes equal partnerships and co-CEOs are a recipe ... | 33m 16s | ||||||
| 2/24/26 | ![]() 059: The Power of Constraints: Designing Joy, Navigating TV, and Reinventing Retail with Shannon Kaye | In this episode, Anne and Matt sit down with color specialist, artist, and former DIY Network TV host Shannon Kaye to explore her unconventional and highly creative career path. From starting as a decorative painter focused on making others' work shine to being unexpectedly thrust into the spotlight as a reality TV host, Shannon unpacks the hidden complexities of the design and television industries. She shares profound lessons on how tight constraints fuel creativity, why avoiding trends in ... | 1h 13m 29s | ||||||
| 2/19/26 | ![]() 058: The "People-First" Playbook: Ben Whitehair on Creative Scaling and Acquisition | In this episode, Matt and Anne welcome guest Ben Whitehair, a unique "actor-preneur" who has mastered the art of building businesses alongside a career in Hollywood. Ben shares the journey of his college-founded startup that saved students $30 million and discusses how his current role at the feminist nonprofit Calling All Crows utilizes the same "CEO mindset" required for creative success. The trio explores the counter-intuitive power of "intentional procrastination," the reality that 86% of... | 1h 18m 37s | ||||||
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| 2/17/26 | ![]() 057: The Wedding Industry Reality Check: Pricing, Boundaries, and the "Vibe Check" with Carly Rae | Everyone thinks wedding planning is just pretty flowers and cake tasting. In this episode, industry veteran Carly Rae (founder of Carly Rae Weddings & High Noon Floral) joins Anne and Matt to reveal the gritty reality of managing high-stakes events, from "burning" medical records to burning the midnight oil for Hollywood celebrities. Carly breaks down her journey from undercutting the competition to commanding luxury pricing, sharing why "raising your prices" is often a test of nerve rath... | 1h 13m 22s | ||||||
| 2/12/26 | ![]() 056: The Death of the Specialist: Why Your "Time vs. Money" Mindset is Failing | The duo explores the critical shift from billing for time to billing for impact, with Anne explaining how she now ruthlessly deletes tasks that don't directly serve her top three yearly goals. Matt argues that the job market is evolving into a landscape of "mini venture capitalists," where employees are hired not for a specific role, but to own an outcome entirely using AI tools. The episode wraps with a reality check on perfectionism: you have the right to change your mind personally, but in... | 30m 04s | ||||||
| 2/10/26 | ![]() 055: Living in the Gray: Why Political Rigidity Kills Business Growth | Matt and Anne explore the argument that politics is often just a "metagame" that distracts founders from the hard work of building a business. They discuss the dangers of rigidity—suggesting that if you are inflexible in your political beliefs, you are likely inflexible in your business strategy as well. Anne shares her perspective on overcoming a "people-pleaser" mentality to find a middle ground , while Matt breaks down why alienating half your customer base is rarely a winning strategy for... | 33m 00s | ||||||
| 2/5/26 | ![]() 054: Changing Rooms: Pivoting to M&A and The Sales Pipeline Reality Check | Matt and Anne discuss the delicate balance of founder energy and the obligation to "show up" for clients, even when Friday feels like a Sunday. The conversation moves to Anne's strategic pivot with Fix & Form, targeting high-stakes M&A and healthcare companies rather than solopreneurs. Matt identifies a dangerous gap in her focus: prioritizing operations and fundraising over active selling. They break down the sobering timeline of enterprise sales—where "starting today" means getting ... | 1h 14m 43s | ||||||
| 2/3/26 | ![]() 053: Avoiding Product Bloat & The "Gun Range" Approach to Content | In this episode, Matt breaks down the discipline required to manage technical debt, explaining why ChipBot rejects nearly 90% of feature requests to prevent the product from becoming bloated. The conversation shifts to the rapid evolution of AI video, where Matt highlights how open-source models are beginning to challenge restricted platforms like Sora. Finally, Anne and Matt discuss the strategy of "flooding" social media with experimental content, using a gun range analogy to illustrate why... | 28m 19s | ||||||
| 1/29/26 | ![]() 052: The Content Gatekeepers: Deepfakes, Platform Responsibility, and Digital Parenting | In this episode, Anne and Matt discuss the fallout from X’s Grok and the disturbing rise of AI-generated exploitation. They argue that while the tools themselves—like Photoshop before them—are just instruments, the true burden of safety lies with the social media giants who control distribution. The discussion covers the futility of federal regulation in the US, the potential for state-based solutions, and the overwhelming challenge parents face in teaching children to discern real from fake ... | 25m 53s | ||||||
| 1/27/26 | ![]() 051: The North Star Metric: One Million Websites & The "Work Family" Myth | In this episode, Matt and Anne explore how to kickstart momentum when the team is lagging behind the founder's energy. While Anne emphasizes the importance of social connection and viewing the team as a "second family" to build identity and engagement , Matt pushes back, arguing that viewing business as family is a mask that hides the reality of business mechanics. The two compare their personal drivers for 2026: Anne’s service-focused goal of delivering 12 deep brand makeovers versus Matt’s ... | 22m 13s | ||||||
| 1/22/26 | ![]() 050: The 10X Revenue Trap & Why Founders Should Focus on Boring Inputs | Matt and Anne return from the holiday break battling "January brain fog" and a wave of post-vacation sickness to tackle the myth of the "10X Revenue" goal. They discuss why setting revenue targets is often a recipe for failure because revenue is a lagging indicator you cannot control. Instead, they argue for 10Xing the "unsexy" inputs—activity, outreach, and product quality—that actually drive growth. The conversation explores how this mindset applies to everything from weight loss to parenti... | 36m 02s | ||||||
| 1/20/26 | ![]() 049: Holiday Boundaries: How Saying "No" Unlocked a Record-Breaking Week of Productivity | In this episode, Anne reveals how saying "no" to traditional holiday travel unlocked her most productive week of the year. While Matt joins from the road in Chicago, the two discuss the power of "breaking the cycle" of family obligations and the necessity of advocating for your own schedule—introducing the non-negotiable concept of "Anne's Time". From drafting a new book to finalizing a full company rebrand, listen in to learn how setting hard boundaries can drastically transform your work-li... | 24m 09s | ||||||
| 1/15/26 | ![]() 048: Negotiating Limits: When to Hold the Line and When to Let Go | In this episode, Matt and Anne dive deep into the often misunderstood dynamic of setting boundaries. While Anne advocates for boundaries as a critical tool for self-worth and ensuring others feel seen, Matt challenges the traditional view with a goal-oriented approach where unwavering directness is often just efficiency in disguise. From Matt’s six-week table tennis training blocks to Anne’s decision to break her own rules for a breakthrough client session, they explore the constant negotiati... | 22m 51s | ||||||
| 1/13/26 | ![]() 047: The AI Survival Game: OpenAI vs. Google & Strategic Lessons from the US Open | In this episode, Matt joins from the US Open in Las Vegas to break down how a loss in table tennis revealed a critical lesson in business strategy: the importance of sticking to your plan even when the opponent adapts. The conversation then pivots to the volatile landscape of Artificial Intelligence, where Matt argues that OpenAI is facing a "survival issue" as Google’s Gemini and open-source models catch up in quality and price. Matt demystifies how LLMs actually work—explaining they are mat... | 27m 32s | ||||||
| 1/8/26 | ![]() 046: Passion Isn’t Enough: Time, Money, and the Product vs. Service Trap | Matt and Anne unpack one of the hardest mental shifts founders face: moving from trading time for money to building something outcome-driven. What starts as a casual conversation about coffee and creatine quickly turns into a deep dive on pricing ethics, discount traps, burnout, pivoting (aka quitting), and why so many service businesses struggle to ever become real products. They explore why content, personal brands, and SaaS all live in a gray area where effort doesn’t equal immediate payof... | 49m 48s | ||||||
| 1/7/26 | ![]() 045: Trading the Stage, Not the Shortcut: Integrity, Identity, and Just Doing the Thing | Matt and Anne dig into what it really looks like to step into a new identity before you feel ready. Anne shares a major personal and business shift—repositioning Fix & Form as a Denver branding firm, committing to local growth, and finally claiming “speaker” as part of her professional identity. The conversation goes deep on integrity versus shortcuts, why faking momentum rarely matters, and how real traction often comes from doing the uncomfortable, unscalable work—applying, asking, pitc... | 35m 16s | ||||||
| 1/1/26 | ![]() 044: Change the Room, Change the Outcome: Content, Focus, and Founder Context Switching | Matt Lo and Anne Gillaspie unpack a deceptively simple idea with massive implications for founders: your environment dictates your mindset — and your mindset dictates outcomes. This episode starts with content creation vulnerability and ends somewhere much deeper: how founders survive chaos, context switch without burnout, and build momentum when everything they do pulls them in different directions. From coffee shops as productivity hacks, to separating “play mode” from “win mode,” to why co... | 1h 00m 19s | ||||||
| 12/18/25 | ![]() 043: Ego, Early Careers & Wartime Leadership | Some episodes wander into gold on accident—this is one of them. On a snowy Denver morning, Matt and Anne fall into a raw, surprising conversation about early-career scrappiness, ego in your 20s, asking “dumb” questions as a superpower, and why distilling chaos into a single clear droplet is the mark of a strong founder. They unpack how emotional maturity shapes work dynamics, why some leaders stop learning, and the difference between wartime vs. peacetime CEOs. It’s an unexpectedly deep dive ... | 45m 26s | ||||||
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