From Startup to $1B: Sasha Orloff on What VCs Really Look For
In this episode of Build Mode, host Isabelle Johannesen interviews Sasha Orloff, founder and CEO of Puzzle, about the journey of securing over $1 billion in venture capital. Drawing from his experience as a Startup Battlefield alum, Orloff reveals what investors truly prioritize in founders. He stresses the need for deep financial literacy, highlighting how disorganized data and unclear metrics can undermine credibility. Waiting too long to initiate fundraising, he warns, reduces leverage and hurts valuation potential.
Orloff outlines common pitfalls such as lacking a solid financial model or delaying investor outreach until crisis mode. He explains how venture capitalists assess a company’s financial foundation and why early preparation is crucial. Using real examples and personal stories, he offers practical steps for founders—organizing financial records, mastering key performance indicators, and building a compelling narrative. The discussion serves as a guide for entrepreneurs at any stage, helping them strengthen their pitch and avoid costly mistakes in the fundraising process.