In this talk, Adeo Ressi (presented by Royston G King) outlines a practical framework for securing investment. He stresses that founders should only ask for funding when they have a realistic chance of a yes, because a rejection is often final. The timing of the ask is critical and should follow a series of relationship‑building touchpoints—coffee meetings, event attendance, news updates, and personal interactions. After roughly four to five meaningful engagements, when the probability of a positive response is at least 50%, the founder should request a decisive meeting (often over dinner) and make a concise, direct ask. Each interaction’s purpose is to secure the next meeting, not to deliver lengthy emails or presentations. Ressi notes that the likelihood of closing a deal rises with each interaction up to about six or seven contacts, after which it begins to decline. The overall message is a disciplined, step‑by‑step approach that maximizes the chance of an investor saying yes.
Chapters
You never ask for something until you think you're going to get a yes. Okay, okay, listen to me clearly. Don't ask for something unless you think you're going to get a yes. If you think you're going to get a no, don't ask. Right? Because a no is forever, right? Once you get the no, there's no going back to yes. So, and by the way, the timing of when to ask is very important. So here's what you do. You meet with them, you invite them to coffee, you send them a little news update, you see they're speaking at an event or attending an event, you go to the event, right? Maybe then you say, "Hey, I have a question I want to ask you. Can we meet for dinner?" And when you're pretty dang sure that you've had 4 or 5 separate interactions with them, that there's a good probability that they'll say yes, at least 50%, you invite them to dinner, you get them on the phone, and you only ask at that point. And I'll talk about how you ask, but basically they may say something like, "Oh, I'm kind of interested, let me think about it." You might do a funding update or some other news update, and if they don't say yes at that point, they're going to go to no. So a couple things I'll talk about how to ask in a moment, but the goal of each and every meeting you have with an investor is to get to the next meeting. So let me be abundantly clear about, uh, like, people, you will write emails that are like 10 pages, and I'm guilty of this too, they're like 5 pages, like long, right? And but your goal is to get to the next meeting, so you want to write an email that's like one sentence: great to meet you, comma, uh, can we connect for coffee next week, question mark. You know, that's it, name. So because each time you build back to this chart, each time you interact with a potential investor, the likelihood of you closing the deal increases because they're committing more time, they're growing the relationship, until about 5, 6, or 7 interactions, then it will start to decline after that. But the goal of each and every interaction in each and every meeting is to get to the next meeting, and that's it.
