In this episode, Dean and Anthony sit down with Jeffrey Fidelman, CEO and founder of Fidelman & Co, a fundraising partner to early-stage startups and emerging fund managers. Jeffrey shares the gritty truth about transitioning from corporate leader to founder and what it really takes to build something from scratch. Spoiler: it’s not just about having a strong resume. 

He reflects on his own journey from investment banking to launching a boutique consulting firm and how that evolved into a scalable business with a productized offering. Along the way, Jeffrey outlines the common traps executives fall into when they try to freelance their way into entrepreneurship, and what separates the consultants who burn out from those who build something lasting. 

If you’re exploring life beyond the corporate walls, wondering how to monetize your experience, or thinking about raising capital for a service business, Jeffrey doesn’t sugarcoat it. He offers insight into what investors actually want, why network reliance isn’t a strategy, and how to tell if you’re building a business or just temporarily unemployed with a logo. 

From building repeatable systems to thinking like a scientist in your go-to-market experiments, Jeffrey’s take is refreshingly practical. The advice hits even harder if you’re in the consulting world and debating whether to stay solo or build something bigger. 

It’s the kind of conversation that pulls back the curtain on fundraising myths, shines a light on the risks you don’t see coming, and reminds you that “doing it right” is still a winning strategy.