At Risk to At The Ready
Summary
In this episode, Jeremy and Jim unpack the rapid transformation AI is bringing to the business world. They explore Microsoft's newly released list of 40 job categories most and least at risk from AI disruption, discuss how startups like Trunk Tools are leveraging AI agents in niche sectors like construction, and emphasize the need for small and medium-sized businesses (SMBs) to build a real AI strategy. The hosts highlight that the winners in this AI wave won't just be the biggest companies with the best tools, but the nimblest—those with clarity, focus, and a plan. The conversation offers a grounded, practical roadmap for SMBs who want to start small, avoid pilot purgatory, and unlock early wins with purpose-built AI.THE AI JOKE
"I started a business making yo-yos. It has its ups and downs."
TAKEAWAYS
- 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.
RESOURCES AND TOOLS
- 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)
5. CHAPTERS
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
Creators and Guests
