Sean Mooney welcomes Vinay Kashyap, Partner at Mainsail Partners, to explore the art and science of investing in and scaling bootstrapped software companies. With a focus on relationships, discipline, and resourcefulness, Vinay reveals how Mainsail supports entrepreneurs in building enduring businesses. Discover practical strategies for turning product-driven companies into market leaders, leveraging AI for growth, and navigating the fast-changing tech landscape with confidence.

1:07 - Vinay’s journey into private equity, how his upbringing influenced his career, and the focus on bootstrapped software companies at Mainsail Partners.

6:45 - The value of long-term relationship building, Mainsail’s proactive approach to sourcing investments, and why a three-to-five-year timeline is critical.

10:27 - What makes a great investment: strong growth metrics, durable product quality, and visionary, industry-experienced founders with a learning mindset.

16:29 - Transforming companies post-investment: building infrastructure, upgrading tech stacks, assembling top-tier teams, and implementing data-driven systems.

23:45 - Practical applications of AI within portfolio companies, including customer service transformations and developer productivity optimization.

32:13 - Preparing for a future shaped by AI and the importance of embedding cutting-edge technology into both operations and product offerings.

For more information on Mainsail Partners, go to  https://Mainsailpartners.com/

For more information on Vinay Kashyap, go to  https://www.linkedin.com/in/vinay-kashyap-3646173

For more information on BluWave and this podcast, go to https://www.bluwave.net/podcasts