the bigger the investor, the easier the yes

friday afternoon charles, emiliano and i ran a webinar on the outbound system we use.

most of the questions were about sales. then someone asked the one i was waiting for... does this work for a raise?

so i told them what my own calendar looked like. roughly 30 to 35 investor conversations booked for the following week.

and i wasn't pitching any of them.

none of those started with i'm raising, can i have twenty minutes. every one started as an invitation to talk about what they've learned.

founders assume the biggest investors are the hardest to reach. it makes sense on paper. more money, more inbound, more gatekeepers, more reasons to say no.

that's not what keeps happening.

i see the opposite every week. the people with the most to say are often the quickest yes, because they rarely get asked anything except for money.

the more accomplished someone is, the more willing they are to share their story. the partner who's done thirty deals has thirty stories, and almost nobody asks to hear them. everyone who emails them wants a check.

the day before, on a separate call, a skeptic pushed me on this. why would a serious person give a stranger thirty minutes? my answer was simple. people don't care about you or me. they care about themselves. and the more they've done, the more stories they carry around.

ask them to share what they know and you're not one more founder in the queue. you're the one person that week who wanted to listen.

and listening is cheap. you show up prepared, you ask about the deal they're proudest of, the one they passed on, what they wish founders understood. then you let them talk. that's thirty minutes of the best market research you'll get, from someone who's seen hundreds of companies like yours.

the founder pitching them gets a polite no in two lines. the founder who listened gets a relationship, and when the raise comes up later it comes up as a conversation between two people who already know each other.

it's like the old guy at the end of the bar who built three companies. nobody asks him how he did it. ask once and he'll talk until they turn the lights off.

now the honest part, because the people on that webinar deserved it.

my read is that investor outreach converts at roughly half the rate of sales outreach. on lp outreach we see something like 2.5 to 5 percent. so if you're expecting sales numbers on a raise, recalibrate before you start.

and someone raised the family office and ultra high net worth question. those people don't live in a cold inbox. they're a different motion, and we said so plainly. for that tier there's a private outreach option, and the cold system isn't it.

i'd rather tell you where the machine stops than have you find out three months in.

but for the funds, the angels, the operators who write checks... the pattern holds. you lead with them, not with you. and a relationship that started with them talking about their best deal is a different relationship than one that started with your deck.

long term this is what changes a raise. ai makes asking cheap, so every partner's inbox is drowning in asks. the investor who gets a hundred pitch emails a week might get one invitation to talk about what they've learned. guess which one gets read.

we run investor outreach this way at raasrocket... no pitching on the first touch, and nobody can promise who says yes.

so who's the biggest name on your target list... and when was the last time anyone asked them a question instead of for money?