In this episode of Women Talkin’ ’Bout AI, Jessica sits down with Arlyn Gajilan, founder of Tobey’s Tutor, an AI-powered learning support platform she originally built for her son, who has ADHD and dyslexia.

This conversation is a deep dive into what it actually looks like to build an AI product as a non-technical, bootstrapped founder, from vibe coding and early prototypes to onboarding, safety systems, and pricing decisions.

Jessica fully geeks out with Arlyn as they unpack:

• Building AI to solve a deeply personal problem
• What “vibe coding” can (and can’t) do
• Designing responsibly for children and learning differences
• UX vs. UI decisions that matter
• Bootstrapping, pricing, and intentionally staying small
• Why “AI wrapper” criticism misses the point
• The reality of building while parenting and working full-time

Mentioned in the Episode

• Tobey’s Tutor: https://tobeystutor.com/
• Scientific American (article mentioning Toby’s Tutor): https://www.scientificamerican.com/article/how-one-mom-used-vibe-coding-to-build-an-ai-tutor-for-her-dyslexic-son/
• Mobbin (UX/UI inspiration library); https://mobbin.com/
• Empire of AI by Karen Hao: https://www.penguinrandomhouse.com/books/743569/empire-of-ai-by-karen-hao/
  
  

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As AI shows up everywhere, something shifts, and it becomes harder to tell what’s human and what’s generated.

In this episode, Jessica and Kimberly unpack how AI-driven convenience is reshaping education, relationships, identity, and even big systems (like markets and healthcare). They explore signaling, semiotics, and why “perfect” content can feel thin or unreal, and end with small ways to choose more human signals in a noisy world.

Bonus: If you want to see how this episode ended, tune in on YouTube for a few unfiltered bloopers at the end: https://www.youtube.com/@womentalkinboutai

Topics we cover in this episode:

• AI as an invisible intermediary
• Finding the signal in the noise
• Higher ed reality check
• Why AI feels “safer” than people
• Semiotics
• The “uncanny valley” of social media
• AI for therapy + parenting support
• Cultural swing back

Not-a-Sponsor Bloopers (YouTube only): Stick around on YouTube for our end-of-episode bloopers, featuring our favorite products that are definitely not sponsoring this show (yet). https://www.youtube.com/@womentalkinboutai

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We’re kicking off 2026 with our most personal episode yet.

This conversation wasn’t planned. We sat down intending to talk about what comes next for the show, and instead found ourselves in a deeper discussion about work, burnout, ambition, and what it means to live in a moment where AI is rapidly reshaping labor, identity, and trust.

In this episode:

• Why “work is sacred” feels harder to believe and harder to let go of
• Burnout, hustle culture, and the cognitive dissonance of automation
• Labor zero, post-labor economics, and the fear beneath productivity
• Status, money, degrees, and inherited stories about worth
• Rest as resistance and nervous system regulation
• AI, trust erosion, and the danger of slow confusion
• Dopamine, addiction, and withdrawal at a societal scale
• Why connection may be the real antidote

Sources:

• David Shapiro's Substack on Labor Zero: https://daveshap.substack.com/p/im-starting-a-movement
• He, She, and It by Marge Piercy: https://en.wikipedia.org/wiki/He,_She_and_It
• Ethan Mollick's Substack on the temptation of The Button: https://www.oneusefulthing.org/p/setting-time-on-fire-and-the-temptation
• Rest Is Resistance by Tricia Hersey: https://blackgarnetbooks.com/item/oR7uwsLR1Xu2xerrvdfsqA
• The Last Invention (AI Podcast): https://podcasts.apple.com/us/podcast/the-last-invention/id1839942885

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