Collin Stewart joins this episode to share his journey from humble beginnings as a “geeky sales guy” to becoming a sought-after expert in achieving product-market fit. With a career spanning multiple startups and countless lessons learned, Collin’s insights are a must-hear for anyone building a business from the ground up.

Through candid stories and hard-won wisdom, Collin reveals the mistakes many entrepreneurs make when trying to scale too soon, as well as the key strategies for finding product-market fit. He explains why understanding your customers’ pain points is non-negotiable and how early-stage founders can use customer development to turn insights into revenue.

Collin doesn’t just talk theory—he provides a clear, actionable framework to help entrepreneurs identify real market opportunities, validate their products, and scale sustainably. His emphasis on listening to the market and aligning growth with timing offers a refreshing perspective for founders navigating the challenges of early-stage business.

Whether you’re an entrepreneur searching for direction or a founder ready to scale smartly, this episode is packed with value. Collin’s practical advice, combined with his no-nonsense delivery, will leave you inspired to rethink your approach to product-market fit.

Key Takeaways: * Why product-market fit isn’t binary and how to measure it effectively. * The dangers of premature scaling and how to avoid them. * A step-by-step guide to using customer development as a foundation for growth. * Real-life lessons on creating products the market can’t live without.

Head over to podcast.iamcharlesschwartz.com to download your exclusive companion guide, designed to guide you step-by-step in implementing the strategies revealed in this episode.

KEY POINTS: 2:01 - Common Mistakes: Collin highlights frequent entrepreneurial pitfalls, including ignoring market signals, rushing to scale, and failing to truly understand customer needs. 9:32 - Premature Scaling Risks: The dangers of scaling too early are laid bare as Collin explains why investing in sales teams or development too soon can drain resources without delivering results. 12:11 - Understanding Product-Market Fit: Collin breaks down product-market fit as a spectrum, where success depends on identifying market needs and crafting a solution that directly addresses them. 14:19 - Market Need Importance: Collin emphasizes that strong market demand—not personal passion—is the foundation for sustainable business success. 19:00 - Customer Development Process: A step-by-step framework for engaging with customers, uncovering their pain points, and refining your product to meet market demands. 35:00 - Outbound Sales Timing: Collin discusses the importance of timing outbound efforts to align with market readiness and long-term sales goals. 37:26 - Long-Term Thinking: Founders are urged to adopt a mindset of patience, focusing on sustainable growth and avoiding the trap of short-term gratification.