Most founders wait too long to start fundraising, show up with messy data, and misunderstand the metrics that actually matter to VCs. Those mistakes can cost you leverage, valuation, and sometimes the deal itself. Puzzle CEO Sasha Orloff, who's raised over $1 billion across multiple ventures, just pulled back the curtain on what investors actually look for in a TechCrunch Build Mode interview - and it's not what most founders think.
The conversation between Build Mode host Isabelle Johannessen and Puzzle founder Sasha Orloff cuts through the typical fundraising platitudes. Orloff's been on both sides of the table, and his message is blunt: investors can smell financial desperation and data chaos from a mile away.
"Waiting until you're nearly out of cash to start fundraising" isn't just bad timing - it fundamentally shifts the power dynamic, according to the TechCrunch interview. When VCs know you need money now, your valuation leverage evaporates. It's not about playing games, it's about basic negotiation physics. The founder who can walk away from a bad deal gets a better deal.
But timing is just the surface issue. The deeper problem plaguing founder-investor relationships comes down to financial literacy. Orloff emphasizes that "messy data" and "misunderstood metrics" don't just make you look unprepared - they make you uninvestable. VCs aren't just buying your product vision, they're buying your ability to build a sustainable business. If you can't explain your unit economics or defend your customer acquisition costs in real-time, you're signaling you don't actually understand the business you're running.
Puzzle, Orloff's current company, builds financial operations software for startups - so he's literally in the trenches watching founders struggle with this daily. The patterns are consistent: companies that maintain clean books and understand their financial reality from day one have dramatically smoother fundraising processes. It's not correlation, it's causation.
The metrics that matter aren't always the vanity numbers founders love to showcase. Gross revenue looks great in a pitch deck, but sophisticated investors want to see gross margin, burn rate, runway, and cash conversion cycles. They want to understand not just how much you're making, but how efficiently you're making it and how long you can sustain growth without their money. That last part matters more than founders realize.
Orloff's advice comes at a critical moment for the startup ecosystem. With venture funding still recovering from 2022-2023's downturn, investors have become more selective and diligence-focused. The era of throwing money at promising decks is over. Now VCs want to see operational maturity earlier in a company's lifecycle, which means founders need to level up their financial sophistication before they start taking meetings.
The interview highlights something that doesn't get discussed enough in founder circles: fundraising is a skill you can actually improve at. It's not just about charisma or having the right connections - though those help. It's about demonstrating you understand the financial reality of your business at a granular level. When a VC asks about your churn rate and you fumble for an answer, they're not just noting a missing data point. They're questioning whether you have the operational rigor to scale.
For founders currently in the trenches, Orloff's framework offers a practical checklist. Get your financial data organized before you need it. Understand every metric that drives your business model, not just the ones that look good. Start conversations with investors before you're desperate for cash. And most importantly, be honest about what you know and what you don't - investors respect founders who can identify gaps and explain how they'll address them.
The Build Mode series has been digging into the operational realities of building companies, moving beyond the typical founder origin stories to focus on execution. This episode fits that mission perfectly, offering tactical advice rather than inspirational fluff.
Orloff's insights strip away the mystique around venture fundraising and replace it with something more valuable: a roadmap. The founders who win in this market aren't necessarily the ones with the flashiest products or the biggest TAMs - they're the ones who understand their numbers cold, maintain financial discipline, and start building investor relationships before they need the money. It's unsexy advice, but it's the kind that actually closes rounds. For anyone preparing to fundraise in the current climate, this conversation is required viewing - not for inspiration, but for the operational playbook that separates funded companies from cautionary tales.
