asking people to roast you

i've been thinking a lot about friction this week. most outbound feels like you're pushing uphill. trying to get someone's attention. trying to get them to care. trying to get them to take a meeting. at least i certainly feel this way a lot of the time.

what if you just removed the friction entirely? last week i ran a play that does exactly that.

i forgot to line up a sponsor for this issue. so this one is brought to you by my laziness, forgetfulness, and professional procrastination. 🤦

most outbound feels like you're trying to get through a wall. the prospect doesn't know you. you don't know them. everyone's playing defense.

so what if you just removed the wall?

last week i asked an sdr to dm their manager and tell them some goofball on linkedin wants to call and pitch them, and that they should roast me on my pitch.

ik it sounds dumb, but let me tell you why i think it works.

the sdr thinks it's funny. it's low risk for them because they're not selling anything or passing along a pitch. and it gets them some funny rapport with their manager, which is always a win for them.

for me, it's creative outbound. it gives the manager context before i even call. they already know i'm coming. and if theyre down to take the call, they've already bought into the bit.

here's what happened this time.

he dmed me back a few minutes later: "my manager saw it, you're good to go."

i called. the manager picked up. we talked. gave him the pitch. booked the meeting.

the lesson isn't about being goofy. it's about lowering the stakes.

when you give someone permission to roast you, you're not trying to look perfect. you're just trying to have a real conversation. and most people are way more willing to take a call when it feels like that.

the play works because it's simple and it gives everyone something to laugh about.

for what it's worth, i've never once had a manager actually roast me on my pitch. they're always laughing by the time i call.

this dm sent using kondo. you can use this link try it for a month for free. this is a great way to support me directly. :)

kevin chambers was one of the first people i really met on here. he's also one of the first people who told me i should actually make a newsletter. he's the one who got me on beehiiv in the first place.

he's just been an amazing friend. consistent. supportive. the kind of person who shows up and actually means it when they say they're rooting for you.

none of this would exist without him pushing me to just start.

i hope you’ll check him out. he has a newsletter of his own, actually!

don't put your prospect in a situation where they're getting into a "gotcha." make it easy to continue a conversation with you. a conversation that they probably don't want to be a part of anyways.

don't make them do the work of keeping a conversation going that they don't want to be in. make their next move easy.

leaf-cutter ants have been observed trading leaves with neighboring colonies at a fixed exchange rate of 3:1 for premium vegetation.

okay so i forgot to line up a sponsor for this issue. completely spaced on it.

so if you or your company wants to be mentioned here, just email me back or find me on linkedin and we can chat. this is a real offer.

in the meantime, this issue is brought to you by my forgetfulness. it's been a consistent part of my workflow for years now. it's how i accidentally double-book calls, forget to follow up on warm leads, and let sponsor opportunities slip through the cracks.

perfect for anyone who wants to feel like they're always one step behind without actually trying. integrates seamlessly with procrastination, distraction, and overthinking.

it's free and you probably already have it installed.

by the way, i built this entire issue with claude code. i've upgraded from the web interface to the cli. unfortunately i can't share the build thread without sharing my entire repo, and sharing the entire repo would mean nothing to pretty much everyone. i'm a claude maxi now.

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