Learn what VCs actually want, from a founder who’s raised $1B

Sasha Orloff, a founder who has raised over $1 billion in capital, shares hard-won fundraising insights on the Build Mode podcast. His core message: investors back founders who demonstrate financial clarity, maintain clean data, and begin raising well before cash reserves run low.

On a recent episode of the Build Mode podcast, Sasha Orloff — founder and CEO of financial software company Puzzle and a veteran who has secured more than $1 billion in funding across his career — breaks down what venture capitalists genuinely prioritize when evaluating startup founders. His central argument is that financial literacy and operational transparency are non-negotiable differentiators.

Orloff highlights several common mistakes that erode a founder's negotiating position: presenting disorganized or inconsistent financial data, misinterpreting key business metrics, and delaying fundraising outreach until the company is dangerously close to running out of money. Each of these missteps signals to investors that a founder lacks control over their own business, which can result in lower valuations, weakened deal terms, or losing a term sheet entirely.

The conversation serves as a practical reminder that fundraising is not just about a compelling vision — it requires founders to speak the same financial language as the investors they're pitching, and to engage proactively rather than reactively.

Veteran founder Sasha Orloff, who leads Puzzle — a startup focused on making financial data more accessible for early-stage companies — recently appeared on the Build Mode podcast to share candid guidance on what it actually takes to win over venture capital investors. Drawing on a track record that includes raising more than $1 billion across multiple ventures, Orloff offers a perspective grounded in hard experience rather than abstract theory.

At the heart of his advice is a straightforward but often overlooked principle: investors are fundamentally financial decision-makers, and founders who cannot present their numbers clearly and accurately are immediately at a disadvantage. Orloff points to messy or inconsistent financial records as one of the fastest ways to lose credibility in a fundraising conversation. If a founder cannot explain their own unit economics with confidence, it raises red flags about operational competence across the board.

Equally damaging, Orloff argues, is the tendency to misread or selectively present key performance metrics. Sophisticated investors will probe these figures thoroughly, and any inconsistency between what a founder says and what the data shows can derail an otherwise promising deal. The implication is clear: founders need to internalize their metrics, not just memorize a slide deck.

Perhaps the most actionable piece of advice concerns timing. Orloff stresses that founders who wait until cash reserves are nearly depleted before starting to fundraise are essentially negotiating from a position of desperation — a dynamic that experienced investors can detect and will exploit. Beginning the process earlier preserves optionality, allows founders to be selective about partners, and maintains the leverage needed to negotiate favorable terms.

Why it matters: As venture funding remains more selective than it was during the boom years of 2020 and 2021, founders face a higher bar to secure capital. Orloff's guidance underscores a shift in what investors reward — less tolerance for vague narratives and greater emphasis on financial discipline and self-awareness. For first-time founders especially, understanding these expectations early could mean the difference between a closed round and a missed opportunity.