"I started a business making yo-yos. It has its ups and downs."

• Microsoft’s research shows paralegals, clerks, and bookkeepers are at high risk from AI disruption, while electricians and plumbers are safer—for now.
• AI agents are transforming industries like construction, where Trunk Tools automates scheduling and documentation.
• SMBs often stall in "pilot purgatory"—they experiment with tools but never integrate them into core workflows.
• A real AI strategy must align with business goals and include data governance, cross-functional buy-in, and training.
• Small, focused AI wins (e.g., automating staff scheduling or document management) create momentum and unlock capacity.
• SMBs can beat big players by being agile—able to pivot quickly, adopt efficiently, and embed AI where it counts.
• Off-the-shelf AI tools can fail if they’re not adapted to domain-specific needs; customization matters.
• Outsourcing AI expertise is often smarter than trying to build in-house capabilities too soon.

• Microsoft Reveals 40 Jobs Most & Least Vulnerable to AI
• Construction Startup Trunk Tools Raises $40M for AI Agents
• A Founder’s Guide to Building a Real AI Strategy (Entrepreneur)

00:00 - Opening Joke: The Yo-Yo Business
00:30 - Weekly Catch-Up & AI Headlines
01:06 - Microsoft’s AI Job Impact Report
02:20 - Philosophical Reflections on AI & The Singularity
04:07 - Trunk Tools & AI for Construction
06:00 - The Rise of Purpose-Built AI Agents
07:20 - Main Topic: Building a Real AI Strategy
08:30 - Pilot Purgatory & Strategy Alignment
10:00 - Project Management & Workflow Foundations
12:09 - Where SMBs Can Beat Big Business
14:00 - The Role of a Chief AI Officer
15:04 - Business Planning Before Tool Adoption
17:36 - Avoiding AI Fads and Focusing on ROI
18:43 - Choosing the Right AI Tools for Your Needs
20:13 - Consulting vs DIY AI Implementation
22:17 - Picking Small Wins to Start with AI
23:25 - Closing Advice: Laddering Wins to Strategy

Why did the AI go to confession? It had a lot of processing to do.

• AI chats—including deleted ones—may now be preserved and used in legal cases, such as the ongoing NYT vs. OpenAI lawsuit.
• ChatGPT is not your therapist, lawyer, or priest. Confessions made to AI are not protected by any privilege.
• Businesses using AI tools casually—especially for internal dialogue or strategic planning—could be exposing themselves to future legal discovery.
• AI-fueled scams are rising, especially in crypto and deepfake impersonation. SMBs are often the most vulnerable.
• Despite the risks, saved AI chats can offer opportunities: proof of IP ideation, audit trails for HR or compliance, and public trust through transparency.
• The legal landscape around AI usage is still evolving—users and companies alike need to get ahead of policy gaps.

• Court Orders OpenAI to Preserve Private Chats
• AI-Fueled Scams Surge: Crypto & Deepfake Schemes Targeting SMBs
• Generative AI Empowers Cybercrime
• Featured Article: Sam Altman Warns ChatGPT Conversations May Be Used in Court

00:00 The AI Confessional Joke
01:00 AI as Therapy—Is It Safe?
02:45 Court Order: OpenAI Must Keep All Chats
04:30 Deepfake & Crypto Scams Hit SMBs
06:20 Can AI Chats Be Used in Court?
08:10 Ethical vs. Unethical Use Cases
09:00 Counterpoints: Transparency, Trust & Proof
12:00 A Call for Smarter AI Use & Policy
16:30 Final Thoughts: Use AI Honorably

"What do you call a belt made of fake watches? A waste of time."

• AI is rapidly replacing roles like recruiters and assistants, especially in enterprise settings, creating new opportunities for SMBs to adopt AI affordably.
• AI-generated music acts (e.g., "Velvet Sundown") fooled listeners, showing how synthetic content is becoming indistinguishable from real—and raising questions about authenticity.
• Agentic AI can now autonomously log into accounts and complete complex tasks, mimicking a trained assistant—potentially game-changing for small business operations.
• Security and compliance remain critical concerns, especially for businesses handling sensitive data (e.g., HIPAA, FERPA).
• Small businesses have an agility advantage over large enterprises in adopting and iterating with AI systems quickly.
• Start with low-risk, repetitive tasks (e.g., email triage, calendar management, record expiration cleanup) to begin training and deploying AI safely.
• Set up AI agents like employees: create separate accounts, establish permissions, and implement checks and balances.
• Embrace “good enough” AI performance initially, then iterate and improve—don’t let perfect be the enemy of good.
• Invest in paid AI tools like ChatGPT or Claude to unlock essential features and reliability.
• Adaptation and experimentation are key—start small, use 20–30 minutes daily to test, and grow with the tech while learning.

00:00 The Rise of AI in Recruitment

03:10 AI in the Music Industry: Authenticity vs. Automation

05:51 The Future of Personal Assistants and Automation

09:06 Small Business Opportunities with AI

11:58 Navigating AI Integration in Business

15:07 Ethical Considerations and Security Risks

17:57 Practical Steps for Implementing AI

21:15 The Entrepreneurial Advantage in the AI Era