In this episode, host Taylor Baker speaks with Brett Jaffee, CEO of Caddy Time, about building an on-demand marketplace that connects golfers with caddies and reimagines the golf experience. The conversation centers on identifying overlooked opportunities, leveraging technology to modernize traditional industries, and scaling a lean, high-impact business.
What You’ll Learn
- How identifying a personal pain point can lead to a scalable business idea with clear market demand
- Why underserved markets often exist not due to lack of value, but due to operational complexity
- The role of marketplace platforms in unlocking supply and demand in traditional industries
- How enhancing customer experience can be a powerful driver of adoption and retention
- Why focusing on a specific use case, like tournaments, can accelerate early traction and growth
- The importance of solving multiple problems at once, such as pace of play and score integrity in golf
- How lean teams can build and scale impactful businesses without significant headcount growth
- Why marketing and brand awareness become the primary constraints after product-market fit
Caddy Time demonstrates how a simple idea—making caddies more accessible—can transform an entire segment of an industry by improving experience, efficiency, and fairness. Brett Jaffee’s approach highlights the power of combining technology with deep customer insight, showing that even established, traditional spaces like golf still offer meaningful opportunities for innovation and growth.
To learn more about Brett Jaffee and their work, visit caddytime.com.