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In this special interview edition of Sidecar Sync, Mallory Mejias sits down with Shekar Sivasubramanian, Head of the Wadhwani Institute for Artificial Intelligence, to explore how AI can be deployed at scale for social good. Shekar shares powerful stories of AI in action—from an oral reading fluency assistant helping millions of Indian children, to smartphone-powered pest detection for rural farmers. This episode dives into designing for deployment (not just innovation), building trust with limited data, and why humility and human-centered thinking are vital for transformative impact. It’s a conversation full of heart, hope, and hard-earned wisdom.

Shekar Sivasubramanian brings nearly four decades of experience in technology and business leadership, having scaled multiple startups to billion-dollar valuations. Now Head of the Wadhwani Institute for Artificial Intelligence, he leads a team delivering AI solutions in agriculture, healthcare, and education to underserved populations across India. An alum of IIT Bombay and the University of Missouri–Kansas City, Shekar also maintains deep technical expertise and a research affiliation with Carnegie Mellon University.

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🛠 AI Tools and Resources Mentioned in This Episode:

Wadhwani AI ➡ https://www.wadhwaniai.org

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Amith Nagarajan is the Chairman of Blue Cypress, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

https://linkedin.com/amithnagarajan

Mallory Mejias is passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space. Mallory co-hosts and produces the Sidecar Sync podcast, where she delves into the latest trends in AI and technology, translating them into actionable insights.

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In this special 100th episode of Sidecar Sync, co-hosts Amith Nagarajan and Mallory Mejias take a celebratory stroll down memory lane, unpacking the journey from the show’s inception in 2023 to today. They reflect on five distinct podcast eras, distill the top 10 AI insights echoed across episodes, and get candid about the surprising speed of tech transformation in the association space. You’ll hear how Mallory used Claude and Google Colab to distill hundreds of transcripts, which past guests left a mark, and what the future holds for episode 200. Plus, an exclusive giveaway for loyal listeners and one golden use case every association should adopt today.

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🛠 AI Tools and Resources Mentioned in This Episode:

Claude ➡ https://claude.ai
Google Colab ➡ https://colab.research.google.com
Zapier ➡ https://zapier.com
Groq ➡ https://groq.com
Sidecar AI Learning Hub ➡ https://learn.sidecar.ai

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Amith Nagarajan is the Chairman of Blue Cypress, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

https://linkedin.com/amithnagarajan

Mallory Mejias is passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space. Mallory co-hosts and produces the Sidecar Sync podcast, where she delves into the latest trends in AI and technology, translating them into actionable insights.

https://linkedin.com/mallorymejias

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Is the future of associations being rewritten by influencers? In this episode, Mallory Mejias is joined by Jackson Boyar, co-founder and CEO of Rallyboard, for a sharp and forward-thinking conversation about how digital creators are reshaping professional learning. They explore the competitive rise of “influencer-led” communities like Josh Bersin Academy, how associations can leverage trust and networks in the AI era, and why curated cohorts could be the key to long-term engagement. If you're an association leader wondering how to remain essential in a rapidly shifting landscape, this one's for you.

Jackson Boyar is the Co-founder and CEO of RallyBoard, a peer learning and engagement platform for associations. He previously served as the Founding CEO of Mentor Collective—higher education’s leading mentorship platform—where he led the company for 10 years and now serves as Chairman of the Board. Under Jackson’s leadership, Mentor Collective partnered with hundreds of universities and employers to support more than 500,000 students, earning a spot on the Inc. 5000 list four years in a row. A 2018 Forbes 30 Under 30 honoree, Jackson is also an active angel investor and advisor to socially minded startups.

https://www.linkedin.com/in/jacksonboyar/
Jackon's LinkedIn Post: https://shorturl.at/5EKqn

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🛠 AI Tools and Resources Mentioned in This Episode:

Galileo Learn ➡ https://getgalileo.ai/learn
Rallyboard ➡ https://www.rallyboard.com

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Amith Nagarajan is the Chairman of Blue Cypress, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

https://linkedin.com/amithnagarajan

Mallory Mejias is passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space. Mallory co-hosts and produces the Sidecar Sync podcast, where she delves into the latest trends in AI and technology, translating them into actionable insights.

https://linkedin.com/mallorymejias

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In this audio-focused episode of Sidecar Sync, Mallory Mejias and Amith Nagarajan explore three groundbreaking advancements in AI audio technology—starting with Google’s real-time voice translation for seamless cross-language communication. They then unpack Microsoft’s open-source Vibe Voice, capable of generating full-length, multi-speaker podcasts, before diving into ElevenLabs Music, an AI tool creating fully-licensed, studio-quality tracks from simple prompts. Tune in for laughs, live demos, and serious implications for associations, from global content reach to AI-driven personalization. Plus, hear the hilarious tale of Amith’s early-morning car debacle and Mallory’s AI-generated bounce anthem for associations. This one hits all the right notes!

🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind

📕 Download ‘Ascend 2nd Edition: Unlocking the Power of AI for Associations’ for FREE
https://sidecar.ai/ai

🛠 AI Tools and Resources Mentioned in This Episode:

Google’s Real-Time Translate ➡ https://blog.google/products/translate/language-learning-live-translate
Microsoft Vibe Voice ➡ https://microsoft.github.io/VibeVoice
ElevenLabs Music ➡ https://elevenlabs.io/music
HeyGen ➡ https://www.heygen.com
Notebook LM ➡ https://notebooklm.google
Rasa.io ➡ https://rasa.io
LM Studio ➡ https://lmstudio.ai
Suno ➡ https://www.suno.ai
Sidecar Sync: Online Learning Course Creation at 26x Speed ➡ https://youtu.be/gDxiLRaHMww?si=etN1MSyBayZmXA-5

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Amith Nagarajan is the Chairman of Blue Cypress, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

https://linkedin.com/amithnagarajan

Mallory Mejias is passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space. Mallory co-hosts and produces the Sidecar Sync podcast, where she delves into the latest trends in AI and technology, translating them into actionable insights.

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Thomas Altman, co-founder of Tasio and Betty, joins Mallory Mejias for an electrifying deep dive into the future of AI through the lens of world models—AI systems that don’t just respond but simulate environments and predict outcomes. From Genie 3’s physics-aware interactive worlds to the transformative potential for associations in training, events, and strategy, this episode unpacks the profound shift from reactive AI to systems that “understand” the world. Thomas also shares insights from his new book The Association Knowledge Cycle, and offers practical advice for staying ahead in a rapidly evolving tech landscape.

Thomas Altman started working with associations after earning his graduate degree in applied data modeling techniques. One of the first things Thomas noticed when working with associations was that, while they do a great job of collecting data, hardly anyone is really putting that data to use. In an effort to leverage association data and content, Thomas developed Betty. With Betty, Thomas aims to utilize advanced AI-driven solutions to help associations deliver value to their members.

https://www.linkedin.com/in/thomas-altman-tasio/

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🛠 AI Tools and Resources:

Genie 3 ➡ https://shorturl.at/ndooP
Gemini ➡ https://shorturl.at/fVVHA
Betty ➡ https://meetbetty.ai/
Tasio ➡ https://tasiolabs.com/
The Association Knowledge Cycle ➡ https://meetbetty.ai/#download

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Amith Nagarajan is the Chairman of Blue Cypress, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

https://linkedin.com/amithnagarajan

Mallory Mejias is passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space. Mallory co-hosts and produces the Sidecar Sync podcast, where she delves into the latest trends in AI and technology, translating them into actionable insights.

https://linkedin.com/mallorymejias

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In this episode of Sidecar Sync, Amith Nagarajan and Mallory Mejias tackle the latest developments in AI with a fast-paced series of updates—from Claude overtaking ChatGPT in the voice mode battle, to Google's shockingly tiny Gemma 3 model, to the rocky rollout of GPT-5 and what it teaches us about innovation at scale. Then, the duo zooms out for a big-picture look at AI’s massive and growing energy demands. Can AI keep advancing without breaking the grid? Enter neuromorphic computing—a brain-inspired breakthrough that could power the next era of AI more efficiently. Hot dogs, ant colonies, and nuclear power all make appearances in this can't-miss conversation.

🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind

📕 Download ‘Ascend 2nd Edition: Unlocking the Power of AI for Associations’ for FREE
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🛠 AI Tools and Resources Mentioned in This Episode:

Claude Voice ➡ https://www.anthropic.com/
ChatGPT Voice Mode ➡ https://openai.com/chatgpt
Google Gemma 3 ➡ https://ai.google.dev/gemma
OSS Models (OSS-20B, OSS-120B) ➡ https://huggingface.co/mistralai/Mixtral-8x7B
Mark Hersam’s TED Talk on Neuromorphic Computing ➡ https://www.youtube.com/watch?v=66b49ZrJzdw&t=3s

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📅 Find out more digitalNow 2025 and register now:
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👍 Like & Subscribe!
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Amith Nagarajan is the Chairman of Blue Cypress, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

https://linkedin.com/amithnagarajan

Mallory Mejias is passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space. Mallory co-hosts and produces the Sidecar Sync podcast, where she delves into the latest trends in AI and technology, translating them into actionable insights.

https://linkedin.com/mallorymejias

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In this episode of Sidecar Sync, Amith Nagarajan and Mallory Mejias dive into two groundbreaking releases from OpenAI: the long-awaited GPT-5 and the surprising return to open source with GPT-OSS. They unpack the shift toward simplified AI interaction, the implications of automatic model selection, and what GPT-5’s real-world performance means for power users. Then they explore how the new OSS models may radically reshape how associations build and deploy custom AI solutions. Plus: updates from ASAE Annual, thoughts on AI hallucinations, and why association leaders should start thinking more like engineers.

🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind

📕 Download ‘Ascend 2nd Edition: Unlocking the Power of AI for Associations’ for FREE
https://sidecar.ai/ai

🛠 AI Tools and Resources Mentioned in This Episode:

ChatGPT (GPT-5) ➡ https://chat.openai.com
Claude 4.1 Opus ➡ https://www.anthropic.com
Soundpost ➡ https://www.soundpost.ai
LM Studio ➡ https://lmstudio.ai
Hugging Face ➡ https://huggingface.co
Quen3 ➡ https://qwenlm.github.io/blog/qwen3/
Kimi K2 by Moonshot AI ➡ https://www.moonshot.cn
OpenRouter ➡ https://openrouter.ai

🔎 Check out Sidecar's AI Learning Hub
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📅 Find out more digitalNow 2025 and register now:
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👍 Like & Subscribe!
https://x.com/sidecarglobal
https://www.youtube.com/@SidecarSync
https://sidecar.ai/
https://www.linkedin.com/company/sidecar-global/

Amith Nagarajan is the Chairman of Blue Cypress, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

https://linkedin.com/amithnagarajan

Mallory Mejias is passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space. Mallory co-hosts and produces the Sidecar Sync podcast, where she delves into the latest trends in AI and technology, translating them into actionable insights.

https://linkedin.com/mallorymejias

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In this episode of Sidecar Sync, co-hosts Mallory Mejias sits down with Dr. Nicola Sahar to explore how a University of Toronto med student dove head-first into clinical AI research and went on to found Semantic Health, an AI-powered medical coding platform later acquired by the American Academy of Professional Coders in 2023. They unpack the art and science of medical coding, discuss why AI will augment rather than replace coders, dive into the critical role of data privacy and private-cloud deployments in healthcare AI, and share why associations are uniquely positioned to guide their members through this AI transformation.

Dr. Nick Sahar is a Canadian physician and health tech entrepreneur who co-founded Semantic Health. In 2023, Semantic Health was acquired by the American Academy of Professional Coders - AAPC - marking a significant milestone in the adoption of AI in healthcare operations. Today, Dr. Sahar remains an active voice in the healthcare AI space, focused on building tools that support clinicians and improve patient care.

LinkedIn - https://www.linkedin.com/in/nicolasahar/
Semantic Health - https://www.semantichealth.ai/
AAPC - https://www.aapc.com/

🤖 Join the AI Mastermind: https://sidecar.ai/association-ai-mastermind

📕 Download ‘Ascend 2nd Edition: Unlocking the Power of AI for Associations’ for FREE
https://sidecar.ai/ai

🛠 AI Tools and Resources Mentioned in This Episode:
ChatGPT ➡ https://chat.openai.com
Claude ➡ https://claude.ai

🔎 Check out Sidecar's AI Learning Hub
https://learn.sidecar.ai

📅 Find out more digitalNow 2025 and register now:
https://digitalnow.sidecar.ai/

👍 Like & Subscribe!
https://x.com/sidecarglobal
https://www.youtube.com/@SidecarSync
https://sidecar.ai/
https://www.linkedin.com/company/sidecar-global/

Amith Nagarajan is the Chairman of Blue Cypress, a family of purpose-driven companies and proud practitioners of Conscious Capitalism. The Blue Cypress companies focus on helping associations, non-profits, and other purpose-driven organizations achieve long-term success. Amith is also an active early-stage investor in B2B SaaS companies. He’s had the good fortune of nearly three decades of success as an entrepreneur and enjoys helping others in their journey.

https://linkedin.com/amithnagarajan

Mallory Mejias is passionate about creating opportunities for association professionals to learn, grow, and better serve their members using artificial intelligence. She enjoys blending creativity and innovation to produce fresh, meaningful content for the association space. Mallory co-hosts and produces the Sidecar Sync podcast, where she delves into the latest trends in AI and technology, translating them into actionable insights.

https://linkedin.com/mallorymejias