What Startups Raising $1B Learn: Advice from Puzzle Founder

Photo: TechCrunch
Quick answer
Puzzle founder Sasha Orloff shares fundraising secrets: key financial metrics, due diligence preparation, and how transparency builds investor trust.
Sasha Orloff, founder of Puzzle—a financial management platform for startups—shared insights on the key factors driving successful fundraising. Over his career, he has raised over $1 billion for multiple companies and identified the most common mistakes founders make when engaging with venture investors.
According to Orloff, investors don’t expect flawless financial metrics from startups, but they do demand a deep understanding of the current business reality. Founders should master key indicators such as revenue growth rates, sales efficiency, profitability margins, and runway. Poor preparation or disorganized data can erode investor trust and reduce company valuation.
Orloff emphasized the due diligence process, noting that missing documentation nearly derailed one of his deals. Investors value transparency and quick access to financial data, which accelerates decision-making. He also highlighted that investor expectations evolve across funding stages, from pre-seed to Series B and beyond.
Honesty about business weaknesses can work in founders’ favor, Orloff added. Investors appreciate a realistic approach and willingness to discuss challenges—not just successes. This experience inspired him to create Puzzle, a platform that helps startups automate financial accounting and analytics using AI.
Common questions
- What financial metrics do venture investors prioritize?
- Investors focus on revenue growth rates, income quality, sales efficiency, profitability margins, and runway. Founders must demonstrate a deep understanding of these metrics and their trends.
- Why shouldn’t founders delay fundraising?
- Delaying investment searches until a critical moment weakens negotiation leverage and risks eroding investor confidence. Early preparation ensures better control over the process.
- How should founders prepare for due diligence during fundraising?
- Prepare financial documentation in advance, ensure data transparency, and comply with regulatory requirements. This builds investor trust and accelerates deal closure.
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