Learn What VCs Actually Want, From a Founder Who's Raised $1B with Sasha Orloff, Puzzle

Investors want founders who understand the financial reality of their business. Messy data, misunderstood metrics, or waiting until you’re nearly out of cash to start fundraising can cost founders leverage, valuation, and even a term sheet.

In this episode of Build Mode, host Isabelle Johannesen sits down with Sasha Orloff, founder and CEO of Puzzle and Startup Battlefield alum, to talk about what he’s learned from building companies that have raised more than $1 billion collectively. 

Sasha breaks down what investors look for during fundraising, which financial metrics founders should know by heart, and why VCs don’t expect your startup to be perfect—they expect you to understand its reality. He also shares how he nearly lost a term sheet because his data room wasn’t ready, how fundraising diligence changes as a startup grows, and why getting your financial house in order can help founders raise with more confidence and leverage.

They get into:

What raising more than $1 billion across multiple companies taught Sasha about fundraising

Why investors value founders who have a strong grasp of their company’s financial reality

The financial metrics founders should know before pitching VCs

How investor expectations change from pre-seed and seed through Series A, B, and beyond

Why revenue growth and the quality of that revenue are critical fundraising metrics

How runway, margins, sales efficiency, and profitability factor into investor decisions

Why waiting until you’re running out of cash can hurt your fundraising leverage

How Sasha nearly lost a term sheet because his data room wasn’t ready