Show Notes
Mike Michelini hosts a live pilot episode with Geraldine and Anne — two Filipino professionals based in Thailand — to explore women's leadership journeys in AI, tech, and global business. Geraldine traces her path from journalism in the Philippines to executive assistant roles in the Middle East, then into fintech and mobile apps, and now AI agent implementation in Chiang Mai, where she spends 10+ hours a day self-studying and attending daily AI conferences. Anne shares her six-year journey with Shadstone, shifting from health and medical studies into marketing, web3, and AI-powered project oversight. Together they unpack why women remain underrepresented at tech and AI events in Asia, the cultural and systemic barriers holding women back from technical roles, and how curiosity, community learning, and calculated risk-taking can help non-developers pivot into high-impact AI work — insights directly relevant for cross-border entrepreneurs building remote teams.
Topics Covered in this Episode
Geraldine's Journey From Journalism to AI Agents
Geraldine shares how she went from a journalism degree in the Philippines to executive assistant roles in Middle East real estate, then into fintech and mobile apps, before immersing herself in Chiang Mai's AI scene — attending daily conferences, taking extensive notes, and eventually debugging her own AI agents.
Anne's Shift From Medical Studies to Marketing and AI
Anne has worked remotely with Shadstone since 2018 across six years, pivoting from health and medical studies into marketing and web3. She describes herself as a non-developer who sees AI as essential for everyone and plans to use tools like JetBlick AI to oversee projects where agents handle routine work.
Why AI Feels Overwhelming — and Why It Matters Anyway
The group compares today's AI explosion to the early days of the Internet, discussing the constant FOMO of not learning daily and why non-technical professionals need to engage with AI tools now rather than waiting for things to settle.
The Gender Gap at AI and Tech Events in Asia
Mike notes that AI and tech meetups in Chiang Mai's digital nomad scene typically have only 3–5 women in rooms of 30–40 attendees. The conversation explores why — from women gravitating toward people-centric roles to cultural risk-aversion and fear of failure in Asian societies.
Filipino Women as Global Remote Talent
Geraldine and Anne highlight the strengths Filipino women bring to remote work — resilience forged by often being family breadwinners, strong intuition, initiative, and what Anne calls "mind-reading" clients. These traits make them highly effective as VAs, operators, and team leads in cross-border businesses.
Cultural Barriers to Risk-Taking and Entrepreneurship
Mike discusses how Asian and European cultures tend to punish failure more than US culture, with parents fearing loss of face if children take entrepreneurial risks. He stresses the importance of leadership that allows mistakes and encourages experimentation, especially with emerging tools like AI agents.
The Speaker Pipeline Problem for Women in Tech
Mike shares a recurring challenge from events like Cross Border Summit — many female speaker applicants come from sales or service roles and pitch talks that skew promotional rather than deeply technical. He wants more substantive, non-salesy content from women speakers and is actively looking for ways to close that gap.
Curiosity and Courage as the Starting Point
Geraldine's core advice is that everyone starts from scratch in a new field regardless of gender, and women shouldn't be afraid to be beginners again in AI or coding. She urges women who find AI interesting to invest the time, lean on community support, and push past the initial overwhelm.
Building a Culture That Retains Women in Technical Roles
Anne advocates for showcasing positive, fun examples of women leaders rather than simply assigning them more work. She calls for regular engaging activities and a team culture that fosters creativity and enthusiasm instead of burnout.
Practical Tips for Upskilling Remote Teams in AI
For entrepreneurs wondering how to get remote team members — especially women — started with AI, Mike recommends low-pressure mobile AI apps, celebrating small wins, and creating a safe space for questions. Geraldine and Anne add that pairing learning with community and highlighting real benefits like agents handling routine tasks helps build momentum.
People / Companies / Resources Mentioned in this Episode
- Geraldine – AI Agent Implementation, formerly in journalism, real estate EA, fintech
- Anne – Marketing and Operations, Shadstone (6 years)
- Cross Border Summit
- Cross Border Mastermind (Koh Samui)
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