HabitStack Podcast

Scott Ward

Join us for honest, informal conversations with startup and agency founders who are deep in the trenches, actively growing their businesses.  Instead of glorified success stories, we share authentic experiences about the ongoing battles, everyday wins, and relatable struggles.  Perfect for entrepreneurs navigating the challenging middle stage of growth, this podcast offers real insights and genuine advice from peers who are right there with you.

  1. 10/12/2025

    Event-Based Marketing and Double-Sided Marketplace Startups with Bobbie Carlton

    In this episode of the HabitStack Podcast, host Scott Ward interviews Bobbie Carlton, founder of Innovation Women, Innovation Nights, and Carlton PR & Marketing. Bobbie runs a unique business structure where her entire team works for Carlton PR & Marketing and treats her other ventures as clients, with Innovation Women being her largest and "dream job" client. The conversation explores how Bobbie built Innovation Women, a speaker platform connecting underrepresented voices with conference organizers. They discuss the challenge of building a double-sided marketplace, how Bobbie solved the chicken-and-egg problem by collecting calls for speakers to attract more speakers who then referred event organizers back to the platform, and why she crowdfunded 200 speaker profiles before the platform even existed. Bobbie shares her vision of reaching 10,000 speakers explains the five Cs of public speaking: competence, confidence, connections, credibility, and compensation. They dive into why live events and in-person connections will become more crucial as AI makes it harder to distinguish what's real online, the underutilized power of events as a marketing channel, and how Innovation Nights became the primary source of client referrals for her PR agency. Bobbie reflects on the importance of standard operating procedures when transitioning from managing individual contributors to leading leaders, and hiring people better than yourself.

    39 min
  2. 26/11/2025

    Your Mess Becomes Your Message: Brian Swan on Reinvention, Resilience, and Unstoppable Branding

    Scott Ward, host of the HabitStack Podcast, interviews Brian Swan, co-founder with his wife Rhonda of the Unstoppable Branding Agency. Brian shares his unconventional journey from robotics engineer selling actuators to SpaceX to becoming a branding and PR expert. After his wife Rhonda left pharmaceutical sales to pursue affiliate marketing and generate significant income, Brian left his engineering career in 2004. When they lost everything in the 2008 financial crisis, they pivoted to branding themselves as "the Unstoppable Family" while traveling the world. The conversation explores how Brian and Rhonda now help seven-figure to nine-figure founders get media exposure and credibility through PR on platforms like Forbes, USA Today, and the New York Stock Exchange. They dive into Brian's immersion in the tokenization and DeFi space, how fractional ownership through blockchain is reshaping asset ownership, and why Brian emphasizes that everyone has a story worth telling. The episode covers their company evolution from 50 employees during COVID to a lean team of 10, the importance of culture and values, and how they hire from trusted communities. Brian shares his morning routine, his participation in the Wake Up Warrior men's group, and how his father's death from AIDS at his coming-of-age shaped his philosophy of living fully now rather than deferring life until retirement.

    40 min

About

Join us for honest, informal conversations with startup and agency founders who are deep in the trenches, actively growing their businesses.  Instead of glorified success stories, we share authentic experiences about the ongoing battles, everyday wins, and relatable struggles.  Perfect for entrepreneurs navigating the challenging middle stage of growth, this podcast offers real insights and genuine advice from peers who are right there with you.