If you are a business leader trying to get past AI chatter and buzzwords, this episode will help you cut through the noise. Chuck Templeton sits down with longtime friend and generative AI strategist Justin Massa for one of our most actionable conversations to date. Whether you’re trying to figure out what AI means for your business or frustrated by AI tools that don’t deliver, Justin offers clarifying frameworks, real-world case studies, and an accessible perspective on how business leaders can integrate generative AI to drive real, tangible value. In this episode, Chuck and Justin cover a wide range of topics from how to think about “the jagged frontier” of AI capabilities, when to use a frontier model versus AI products, how the technology will shape companies and industries, when AI agents might come into play, and how to transform your AI strategy from ad hoc experimentation to holistic transformation. This episode is packed with insights for anyone trying to navigate the tension between risk, opportunity, and speed in an increasingly AI-driven world.

Key Takeaways:

1. The Jagged Frontier: Justin introduces the concept of the jagged frontier, where AI outperforms in some tasks but fails in others, and its capabilities are continuously in flux.
2. CEOs Should Lead the Charge: According to Justin, CEOs must be direct users of AI tools. Think of learning AI like learning to ride a bike: no amount of theory substitutes for falling, getting back up, and finally figuring it out.
3. Frameworks for Implementation: Justin outlines three paths to integrating AI: as a technique (low lift), a jig (a custom-built tool for a specific job), or a tool (enterprise software, larger investment). Each has a different speed, cost, and return profile.
4. AI Ethics: According to Justin, there are three layers of ethics and governance when it comes to AI: creation, operation, and application. The application level in particular demands an ethics and governance policy that is constantly evolving.
5. AI Won’t Replace Your Team–But it Will Reshape How They Work: Justin shares that companies like Red Antler are already seeing employees “buy back” large percentages of their time using generative AI, and reinvesting it into creative, strategic work.

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This content is for informational purposes only, should not be taken as legal, business, tax or investment advice, or be used to evaluate any investment or security, and is not directed at any investor or potential investor in any investment vehicle sponsored by S2G. Investing involves risk, including the risk of loss. Specific companies mentioned in this podcast are for educational purposes and should not be construed as an endorsement of any kind. S2G holds positions in the companies referenced, but this podcast is for information purposes only and is not intended to promote any such company. All views of the guests on this podcast are solely their opinions and do not reflect the opinions of S2G. Any past performance discussed is not indicative of future results. Chuck Templeton is a Managing Partner at S2G Investments. All Chuck's views, and the views of the guests on this podcast, are solely their opinions and do not necessarily reflect the opinions of S2G. The views expressed herein are opinions based on certain assumptions and subject to change.

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