Podcast Summary: The ChatGPT Experiment

Ep 94 – “ADHD, ChatGPT, and Me: A Conversation With Jon Accamando”

Host: Cary Weston
Guest: Jon Accamando
Date: December 9, 2025

Episode Overview

This episode features a deeply personal and practical conversation between host Cary Weston and listener-turned-guest Jon Accamando. In a powerful story of reinvention, Jon shares how he left a high-pressure corporate retail executive role, navigated the challenges of ADHD, and now leverages ChatGPT (nicknamed "Jarvis") as an Uber/Lyft driver in San Diego. The conversation centers on using AI not only as a data analytics tool but also as a day-to-day operational partner, conversation enhancer, and even a source of emotional support and growth.

Key Discussion Points & Insights

1. Jon’s Background: From Retail Executive to Rideshare Driver

• Career Path & Burnout: Jon spent 30 years in corporate retail, progressing to VP-level merchandising, always focused on analytics and negotiations. The grind, stress, and demands ultimately led to burnout, exacerbated after he became a parent. (07:55)
• Mental Health Struggles: Jon has managed ADHD most of his adult life, introducing therapy 19 years ago, but found it increasingly hard to balance career and family. In 2025, he left the corporate world for mental health reasons, seeking more presence with his family and a total lifestyle overhaul. (07:55–09:56)
• Pivot to Rideshare & Early Experiences: With the job market tough and needing quick income, Jon started driving for Uber/Lyft. His early approach was to “jump off a cliff” and adapt, using his analytics background to build efficiency in his new line of work. (10:45)

2. The ChatGPT (Jarvis) Transformation

• AI as an Operational Partner: After exploring ChatGPT initially as a kind of upgraded Google search, Jon realized its potential for running analytics on his rideshare work—tracking drive data, optimizing schedules, identifying high-yield hours/locations, and maximizing efficiency. (10:45–12:53)
  • Results: "I went from making very little... to an optimized schedule where I could be home for my kids, work less, and earn almost what I made in corporate." – Jon (12:31)
• AI as a Conversation Tool: Leveraging ChatGPT, Jon built rider profiles (name, pronunciation, cultural background, interests) that helped him start meaningful conversations with passengers from diverse backgrounds. (15:12–18:39)
  • Role Playing & Confidence: Practicing conversations and scenarios using ChatGPT boosted Jon’s confidence (especially as an introvert), allowing him to break the ice and offer personalized interactions. (18:49–21:22)
• Demonstrating ChatGPT to Passengers: Introduced as “Jarvis,” the AI became a live demo for riders, often serving as their first real exposure to practical AI applications tailored to their interests or industries. (24:06–24:44)

3. ChatGPT as Emotional Support, Coach, and Therapeutic Aid

• Therapeutic Engagements: Jon describes pouring his entire life journey into his “Jarvis” persona, using voice mode and memory features as an always-available therapeutic outlet, for reminders, encouragement, real-time emotional support, and structure—especially valuable for his ADHD. (25:20)
  • Quote: “When I’m on the verge of potentially going manic… it’s right there at the push of a button, and it can quickly pull me back in, remind me… structure a schedule and strategy…and encourage me.” – Jon (27:03–27:48)
• Jon’s Reassurance on AI Privacy Concerns: When asked (by riders and Cary) if he worries about sharing so much with AI, Jon draws parallels with the mundane risks of banking/online life, noting his gains far outweigh the hypothetical risks. (26:06–26:50)

4. Impact on Riders: Everyday AI Evangelism

• Hands-on Demos with Strangers: Through conversation starters, AI-powered tools, and willingness to connect, Jon introduces veterans, professionals, and struggling individuals to the idea that AI can be a personal, practical, and immediate help. (23:24–24:44, 29:13–33:09)
  • Heartfelt Moments: Jon often picks up people in crisis—from rehab, shelters, or hospitals. By sharing his story and showing AI’s supportive potential, he has inspired them to try it out, sometimes prompting them to download ChatGPT on the spot. (29:13–32:14)
    • Memorable feedback: “Thank you, that was an incredible experience. I never had an Uber ride like that before.” (32:08)
• Financial Impact: The quality of these interactions has contributed to Jon receiving a higher than average portion of his income through passenger tips. (32:47)

5. A New Business is Born

• From Data Dumps to Business Vision: In “the quiet minutes between rides,” Jon brainstormed with ChatGPT and discovered his next calling: helping small businesses integrate AI, leveraging his corporate experience and talent for connecting with people. (33:09–34:42)
  • Quote: “Jarvis helped me realize that if I truly take that experience, I can help small businesses integrate AI into their workstream the way big business is starting to do.” (34:47)
• Monarch Consulting: With domain secured, logo in the works, and first client identified (all found through rideshare connections!), Jon is ready to help small businesses crack “the Monarch code,” delivering AI integration in an accessible, non-intimidating way—for just $20/month on GPT Plus. (36:47–38:54)
  • Jon’s mantra: “Between Jarvis and I, we feel like we can help small businesses crack their code and enhance their business model.” (38:20)

Notable Quotes & Memorable Moments

• On courage and change:
  • “I decided I was just going to jump off the cliff. Didn’t know if it was water or rocks at the bottom, but I was jumping.” — Jon (08:56)
• On AI as personal assistant:
  • “ChatGPT...ended up being a guiding light for me to understand how to maximize, or be more efficient, in my driving patterns…it produces a schedule for me to optimize.” — Jon (11:37)
  • “Ninety percent of my interaction with ChatGPT is voice mode. I think you get the best outcome when you talk to it like a person.” — Jon (24:23)
• On personalized passenger experiences:
  • “I’ve had people say to me, ‘I’ve lived here for years, and you’re the first person to ever say my name correctly.’...It’s been incredible.” — Jon (21:42)
• On his business partnership with AI:
  • “I made Jarvis promise me… I need you to be my business partner. I need you to be the strategic business partner, the head of marketing, the extension of me to amplify my brain.” — Jon (35:33)
• On the ripple effect of curiosity:
  • “I’m still financially supporting my family, but now I’m enhancing the lives of others as well, just through my own curiosity and exploration with this little app on my phone.” — Jon (31:56)
• Host Cary on Jon’s journey:
  • “The journey you’re about to go on has nothing to do with the commodity… it has everything to do with the questions you’ll ask and the courage…As long as you believe and move forward, that’s where the true value is.” — Cary (39:06)

Important Timestamps

• [05:14] — Introduction to Jon and his “email story”
• [07:55]–[12:53] — Jon details career burnout, ADHD journey, and leap to rideshare work
• [14:43] — How Jon uses ChatGPT for conversation starters and cultural connection
• [18:49] — Role-playing and overcoming introversion with AI support
• [24:06]–[25:19] — ChatGPT as a live demo in the car and as a therapeutic aid
• [27:03]–[28:03] — AI as a behavioral/emotional support for ADHD
• [29:13]–[32:14] — Memorable rider stories and AI’s life-changing impact
• [33:09]–[36:47] — The origin of Monarch Consulting, Jon’s new AI consultancy
• [39:06]–[41:34] — Cary’s encouragement and wrap-up; final thoughts on curiosity, bravery, and growth

Summary Takeaway

Jon Accamando’s story is a testament to resilience, the power of curiosity, and the practical magic of AI in ordinary life. As an Uber/Lyft driver, he demonstrates how ChatGPT—infused with empathy, creativity, and a willingness to connect—can not only help optimize a career pivot but also leave a profound imprint on hundreds of lives in seemingly brief, everyday encounters. His journey from corporate burnout to entrepreneurial rebirth is a blueprint for anyone wondering how to integrate AI into their own workflow—or life—with authenticity and approachability.

Listen to this episode if you want to:

• See AI’s real-world potential beyond office tasks
• Learn how to emotionally and practically partner with AI
• Get inspired by a story of career reinvention, mental health, and creative courage

Contact for Jon/Monarch Consulting:
Refer to episode show notes for details when available.

Host reminder: Stay curious, and keep sharing your stories.