Ask for Advice, Get Money

The aphorism and its origin

"Ask somebody for money, you're going to get advice. Ask somebody for advice, maybe you'll get money."¹ Eric Glyman traces the posture to a moment early in his career when he had accepted a job, then received an offer he felt he could not pass up, and was, in his own words, "totally a wreck" about telling the person he had already committed to.² The advice he received was not to walk in and defend his reasoning, which reads as standoffish, but to ask that person for his advice: explain what happened, say he respected the person's opinion, and describe why the new opportunity could be life changing. The reasoning was that a real mentor, asked that way, will say go for it. It became, in Glyman's words, one of the best conversations he had ever had to that point, and that person remains a mentor. The generalization he draws is to treat the other person as an equal or as someone worth learning from when facing a big decision or a real conflict, because people want what is best for other people.

Applied to early customers

The trap in early sales is thinking in first-order terms: a founder needs revenue growth, has ten-minute meetings, so every meeting becomes an attempt to sell. People recognize that posture and defend against it. Ramp's early version instead opened with something closer to a question than a pitch: an idea for a card that helps businesses spend less, paired with the question of whether the business felt it was spending more money than it wanted to in some area. That framing buys real information about how the business actually works and whether the pain is genuine, moves both sides from opposite ends of the table to solving a shared problem together, and often produces a conditional commitment such as trying the product if a certain step is taken. Glyman also argues most early founders need revenue more than they need funding, and that revenue earned this way makes raising money easier regardless.

Applied to investors

The same posture produced Ramp's first meeting with Keith Rabois. Glyman went because Rabois had been Square's chief operating officer and understood payments, reasoning that the worst case was simply learning something from him. He brought no deck, only an email describing the problem, the team, and their progress, along with a list of his own questions. The meeting shifted quickly from an attempt to convince Rabois into jointly working the problem, and it produced an investment. Glyman's broader read is that most investors want to find a company they can fall in love with and are looking for reasons to say yes, so treating a pitch as an exercise in preempting every objection works against that instinct rather than with it.

The caveat

The posture only works if the person genuinely intends to learn and is willing to act on what they hear, since the real value is the information and the relationship, with any money that follows treated as a byproduct. Glyman pairs it with a volume argument: fifty to one hundred conversations move a founder from good intuition to real pattern recognition.