The Truth About AI, Data, and Human Connection

Show Notes

Samuel sits down with Dona Sarkar — Chief Troublemaker at Microsoft, global AI & accessibility leader, entrepreneur, author, and fashion designer — to explore why human connection is still the most valuable asset in the AI era.

They talk about the limits of automation, why data quality can make or break AI projects, and how leaders can adopt AI without losing their unique voice. Dona shares candid stories from running offline businesses, busts common AI myths, and reveals how to experiment your way to success.

Key Takeaways

• How Dona manages a wine bar, fashion label, and AI at Microsoft
• Three lessons from running real-world businesses with AI
• Why experimenting is the only way to succeed with AI
• The truth about AI agents, memory, and the human in the loop
• A roadmap for adopting AI: start with Copilot, then scale up
• Designing responsible AI agents and fixing accessibility gaps

Resources

• Dona Sarkar’s website