Founder Who Raised $1B Shares What Investors Really Look for in Pitches

Sasha Orloff, founder and CEO of Puzzle, appeared on the Build Mode podcast to discuss what venture capitalists genuinely expect from founders seeking funding. Orloff, who has raised over $1 billion, emphasized that investors prioritize founders with a clear grasp of their business's financial reality. Common pitfalls such as disorganized data, misread metrics, and last-minute fundraising can seriously weaken a founder's negotiating position. Starting the fundraising process too late — when cash is nearly depleted — risks losing valuation and even potential term sheets. The conversation, hosted by Isabelle Johannessen, aimed to help early-stage founders approach investors with greater preparedness and credibility.