What VCs Really Want: A Founder Who Raised $1B Shares the Playbook

Raising venture capital is as much about financial clarity as it is about a compelling vision. Investors are increasingly drawn to founders who demonstrate a deep understanding of their company's financial reality—not just the story. Messy data, misunderstood metrics, or delaying fundraising until the coffers are nearly empty can severely weaken a founder's position, erode valuation, and even cost them a term sheet altogether.

In a recent episode of Build Mode, host Isabelle Johannessen sat down with Sasha Orloff, founder and CEO of Puzzle, a company that has successfully raised more than $1 billion. Orloff shared candid insights into what investors truly look for during the due diligence process and how founders can position themselves for success.

The Metrics That Matter Most

Orloff emphasized that investors want to see a founder who can articulate the unit economics of their business with precision. It's not enough to have impressive top-line growth; understanding customer acquisition costs, lifetime value, and gross margins is essential. He stressed that founders should be intimately familiar with their cash flow and burn rate, as these are the numbers that ultimately determine a company's runway and its ability to weather unexpected challenges.

Another key point Orloff made was the importance of timing. Waiting until you're almost out of cash is a classic mistake that puts founders in a position of weakness. By starting the fundraising process early, founders can negotiate from a place of strength, with multiple options on the table and the time to choose the right partner, not just the first check offered.

Orloff also highlighted the need for clean, organized data. In today's data-rich environment, investors expect founders to have a clear, accessible view of their financials. This means investing in robust accounting systems and ensuring that all stakeholders—from the finance team to the board—are aligned on key metrics. A founder who can present a coherent financial narrative is far more likely to inspire confidence than one who struggles to explain the numbers behind their pitch.

Ultimately, the fundraising journey is a test of a founder's ability to run a business with discipline and foresight. By mastering their financials, understanding their metrics, and approaching investors at the right time, founders can significantly improve their chances of not just securing funding, but building lasting relationships with investors who believe in their long-term vision.