How do you raise money for a startup?

“I raised $5.5 million for VitalSigns in 1997, but only after Monte Kirsten and I put in our own money, took no salary, and shipped a product with six engineers so we could walk into those VC meetings with real adoption rather than a deck. If you can de-risk the company on your own dime first, you keep more ownership and you get a very different conversation with investors.”

“I raised money for my own startup and then for Afore, and the thing that held true across both was that the best founders don't raise on an idea, they raise on a few months of real work. Build the cheapest prototype you can, talk to customers, then go to investors with evidence, not a deck.”

“I raised the first $320M for Neo by treating fundraising as a relationship business long before I needed the money: decades of backing founders and helping them without asking for anything created the LPs who wanted in. My real advice is don't raise until you have happy paying customers and real momentum; desperation makes you marry the wrong people and give away too much of the company.”

“I raised money for Open Market and Appex, and the best advice I can give is: stop treating fundraising as validation. The amount you raise, the valuation, the name of the VC—none of that proves the business works. What matters is whether you have evidence that customers will pay and a clear plan for the milestones that get you to the next round or to cash flow positive.”

“I don't think of it as raising money; I think of it as choosing business partners for the next decade. Build a real relationship before the round, because the term sheet is the beginning, not the achievement. With UiPath, Daniel wasn't even fundraising when we met, and that trust is what made the Series A fast when it happened.”

“I treat fundraising like car shopping, not dating: run a parallel process, target the right firm and partner for your stage and sector, and get a warm intro from a founder who made that VC money. Your pitch needs to set context, be crisp, and be credible in the first five minutes, because partners decide in minutes whether to spend more time.”

“I raised $75 million for LearnVest, and the single best move I made was asking the five smartest people I knew to tear my business plan apart before I ever pitched an investor. Their negative feedback became the exact questions I had to nail, because fundraising is less about selling a dream than proving you have already stress-tested it.”

“I usually challenge founders to first ask why they need the money, because too many jump to fundraising as the default move. With Product Hunt, investors were courting me before I was even sure I wanted to raise, and I only did it because I needed to hire and had no personal capital to pay them.”

“I watch founders raise best when they stop performing for investors and start showing the thing that is already working. At seed, I care more about paid conversion and how fast you ship than a perfect story. Once a product starts to click, confidence spikes, and the pitch almost takes care of itself.”

“I raised Lux's first fund with no track record by building real platforms, not just pitch decks, and by getting Bill Conway at Carlyle to bet on us before we had one. For founders, the money follows a story that makes uncertainty feel knowable: how much capital turns which unknowns into facts in what time.”