A leadership approach emphasizing transparency, self-awareness, and genuine relationships with team members.
11 episodes
Chris Thomajan, a CFO with 35 years of experience across 100+ startups, discusses his career path from English major to finance leader in Boston's biotech ecosystem. He shares frameworks for evaluating founding teams, navigating venture capital cycles, and preparing companies for IPO, emphasizing that betting on the right 'jockey' matters more than the business idea itself.
Louis Gump, fractional CEO/COO and author of Inside Innovator, discusses his career building mobile businesses at CNN and The Weather Channel, the critical differences between entrepreneurs and intrapreneurs, and how founders can successfully transition into larger organizations post-acquisition. He emphasizes that innovation requires leadership commitment, cross-functional collaboration, and understanding when to adapt entrepreneurial instincts to corporate environments.
Mike Martin, fractional CMO at Tech CXO, discusses his career building breakthrough brand campaigns—from the Truth anti-tobacco campaign's guerrilla marketing tactics to Super Bowl spots for Monster.com. He shares lessons on creative courage, navigating difficult bosses, and how AI is transforming marketing while emphasizing that creativity still requires human oversight and strategic foundations.
Matt Oess, a sales and marketing consultant and executive coach at TechCXO, discusses his coaching practice for C-suite leaders, his deep dive into AI productivity tools over the past 14 months, and his advisory role with Purdue's Croc Institute for Tech Diplomacy. He demonstrates practical AI automation workflows he's built using platforms like Make.com, explains the maturity progression from zero-shot generative AI to multi-agent systems, and shares insights on how AI is transforming business operations and the SaaS industry.
Adam Lehde, co-founder of Happen Technologies, discusses building a hybrid software development company that partners US-based strategy with Ukrainian engineering talent. He shares his journey from mobile developer to entrepreneur, the cultural advantages of working with Ukrainian developers, and his philosophy of building a family-first company culture supported by community practices like F3 fitness groups.
Katherine O'Day, partner at Atlanta Ventures, discusses her journey from employee number nine at Pardot through two successful acquisitions (ExactTarget, then Salesforce) to becoming an early-stage investor and venture studio operator. She shares lessons on bootstrapping companies, building culture through core values, and why consistent execution over time—like training for an Ironman—matters more than short bursts of effort in entrepreneurship.
Kirby Winters, fractional CISO at TechCXO, discusses his journey from telecom to cybersecurity consulting, emphasizing leadership lessons from Eagle Scouts and entrepreneurship. He covers the evolving threat landscape—from social engineering to AI-enhanced phishing—and explains how fractional security leadership helps SMBs navigate SOC 2, HIPAA, and CMMC compliance without full-time hires. The conversation explores VPN evolution, cyber insurance realities, and the critical need for proactive security planning before customer mandates or breaches force action.
Rich Makover, a fractional Chief Revenue Officer and executive coach at TechCXO, discusses his journey from Penn State lacrosse player to CPA to sales leadership at Avon and beyond. He shares insights on hiring athletes for sales roles, the importance of resilience over winning, situational coaching methodologies, and his transition to fractional leadership and executive coaching, including his decade-long mentoring program for Penn State lacrosse.
Bart Foster shares his journey from corporate executive to founder of SoloHealth, a health screening kiosk company that scaled to 4,000 Walmart locations before he was forced out by his board. He discusses the emotional trauma of losing his company, his intentional relocation to Boulder, and founding Business Outside—a consulting practice that uses nature-based experiences to help leaders build authentic connections and live more intentionally.
Christy Johnson, performance engineering lead at VIP Ventures, discusses her unconventional path from microfinance in Costa Rica to steel manufacturing to venture capital. She shares lessons from seven years as CEO of a portfolio company, the importance of culture in remote teams, and VIP's hands-on approach to helping founders through focused strategy, investor symposiums, and operational coaching.
Maria Goldsholl, fractional Chief People Officer at TXO, discusses authentic leadership, building trust-based cultures in startups, and the value of fractional executive services. She emphasizes psychological safety, transparent communication, and learning from career setbacks as foundations for effective leadership and organizational growth.
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