The First Customer - The Investor Every Founder Wishes They Had with Dan, Matt, and Jonathan

In this episode, I was lucky enough to interview the Proofpoint Capital founders Dan Goldsmith, Matt Wallach, and Jonathan Brassington. From Jonathan’s upbringing among traders in Guyana to Matt’s competitive lessons on the soccer field and Dan’s drive to tackle challenges others avoided, the trio shares how their unique backgrounds influenced their approach to building successful companies. They also reflect on the first customers that helped launch ventures like LiquidHub and Veeva, offering a candid look at the persistence, trust-building, and humility required in the earliest stages of growth.The Proofpoint Capital founders delve into their operator-led investment philosophy, their focus on AI-powered vertical software companies, and the lessons they’ve learned from decades of scaling businesses. Dan, Matt, and Jonathan explain how they evaluate founders, markets, and defensibility in an era where AI is rapidly changing the rules of business. Along the way, they discuss mentorship, venture risk, the importance of trusted relationships and proprietary data, and the responsibility of helping the next generation of founders avoid costly mistakes. Discover how Dan, Matt, and Jonathan are turning decades of operating experience into a blueprint for helping the next generation of builders succeed in this episode of The First Customer!Guest Info:Proofpoint Capitalhttps://www.proofpointcapital.com/Matt Wallach's LinkedInhttps://www.linkedin.com/in/mattwallach/Dan Goldsmith's LinkedInhttps://www.linkedin.com/in/danielgoldsmith/Jonathan Brassington's LinkedInhttps://www.linkedin.com/in/jonathanbrassington/Connect with Jay on LinkedInhttps://www.linkedin.com/in/jayaigner/The First Customer Youtube Channelhttps://www.youtube.com/@thefirstcustomerpodcastThe First Customer podcast websitehttps://www.firstcustomerpodcast.comFollow The First Customer on LinkedInhttp://www.linkedin.com/company/the-first-customer-podcast/