A new episode of TechCrunch's Build Mode podcast features Sasha Orloff, founder and CEO of Puzzle and a Startup Battlefield alumnus, discussing what investors actually look for when startups raise funding. Orloff has collectively raised over $1 billion across the companies he has built, and he stresses that VCs do not expect founders to run a flawless business, but they do expect founders to genuinely understand its financial reality, since messy data, misread metrics, or fundraising too late can weaken a founder's negotiating position and valuation.

In the conversation with host Isabelle Johannessen, Orloff outlines the financial metrics founders should know cold, how investor expectations shift from pre-seed through later funding rounds, and why revenue quality, runway, margins and sales efficiency matter to investors. He also recounts nearly losing a term sheet because his data room was not ready, explains how being organised and honest about weaknesses can build investor confidence, and describes how his own fundraising frustrations led him to found Puzzle, an accounting-focused startup. The episode also touches on how artificial intelligence could reshape startup accounting and financial management.