the wolf of AI SDR'ing

Hey ya’ll —

I saw an ad this week for an AI SDR product where the face of the brand is Jordan Belfort.

Yes, that Jordan Belfort. The Wolf of Wall Street. Great movie, horrible person.

And now apparently the trust signal for outbound automation in 2026.

Thanks for reading.

~Eric

Eric Boggs
CEO @ RevBoss

PS - as a friendly reminder, you’re receiving this email because you filled out a form on revboss.com at some point or because we interacted on LinkedIn at some point or because you’re my mother. (Hi mom!)

Modern marketing is an exercise in trust.

The funnel as we knew it — top of funnel, MQL, SQL, all the rest of it — is functionally a relic.

What's left is a trust funnel — every element of your go-to-market either builds trust with a prospective buyer or burns it.

The sad truth is that most B2B marketing is burning trust without realizing it, including a lot of what we used to recommend…and including a lot of what you are doing on autopilot right now.

We run 3 plays for our clients:

…and we try to think about trust in each step.

Somebody scrolls past your post or opens your newsletter and decides — pretty quickly — whether you're a person worth paying attention to or just somebody else clogging up their feed.

LinkedIn is the discovery layer. Strangers find you in their feed, next to people they already trust, and they get a 3-second read on whether you sound like a real human being or like a slightly-off ChatGPT impersonation of one.

Newsletters do the heavy lifting. A newsletter is somebody handing you their inbox and saying "OK, you've got a few minutes a week to make this worth my time." That's a different relationship — you can go deeper, share specifics, admit when you're wrong, work through an idea in real time. The format rewards effort and punishes filler in a way that LinkedIn just doesn't.

Lean on the newsletter. Use LinkedIn to bring people to it.

The trust-burning version is the same on both surfaces — generic content, recycled hot takes, AI-written drivel nobody asked for. Anything that signals you're more interested in volume than in saying something real.

Somebody saw your content and didn't immediately mute you. Now you're connecting on LinkedIn.

This is where most B2B GTM goes off the rails.

People treat the connection as a throughput metric — "we added 1,200 connections this month!" — instead of as 1,200 chances to either build or burn trust with a stranger.

The ham-fisted DM ("Hey {{first_name}}, thanks for connecting…") that arrives a nano-second after you accept the connection request is the giveaway.

The version that works is mortifyingly simple — say a real thing about the actual person. Mention the conference. Reference the post. Send them something useful for the sake of being useful and without expecting anything in return.

Not hard. Just not as easy as the lazy, ineffective way.

You've got the connection. Now you want to start a conversation. This is the part where most clients (and most of the market) want to skip directly from "we are connected" to "schedule a 30 min discovery call."

This won’t work. The bar is higher.

There are basically two ways to start a conversation with an internet stranger that doesn't feel gross:

Pick one of those two and you have a chance.

The worst practice is when a message gets a real reply from a real human and then the sender either ghosts the person or shoves them straight at a calendar link before they've expressed any interest in a call.

You sent the message. They wrote back. Your move is not to push them into a meeting.

Give it a beat, be a normal person with empathy, ideas, and humor. And be patient.

Which brings me back to our friend Jordan.

I think that hiring a famous fraudster as the face of your sales-automation brand is a laughable marketing decision and one of the more bizarre brand associations I've seen in a while…but par for the course for an AI SDR product.

(Or maybe this is some kind of 4D chess* move I'm not smart enough to understand. I clearly took the bait after all — I just spent the better part of a morning writing about it in an email I sent to ~16k people.)

The more depressing commentary is this: it’s just another turn on the swirling enshittification spiral that so many marketers are clearly happy to entertain.

We have the most powerful tooling EVER and we’re using it to build AI SDRs that are going to make 1 million marketing corpse flowers bloom.

And we’re promoting them with lines like “If your outbound doesn’t run itself, you’re already behind” from a literal penny-stock scam fraudster.

…that’s amplified by a swarm of astroturfing bots and auto-commentors.

I’m going outside to stare at the sun for a few minutes.

*It’s not 4D chess.

That’s my girls and me in the Roan Highlands this past weekend.

We spent a long weekend there with some of my college roommates and their families. (Wife and son were — where else? — on a soccer field.)

I've done a lot of hiking in GA, NC, TN, and VA over the years, and the two best bang-for-your-non-hiker-buck spots I've found are:

Both places, you drive up the mountain, park in a lot, walk maybe a quarter mile up a hill, and you get a view that you'd normally have to spend half a day on a real trail to earn.

Pretty much zero effort, maximum payoff.

Our whole deal at RevBoss these days is figuring out how we can drive our clients to the parking lot that’s 95% of the way up the mountain and let them walk the last quarter mile to get the view.

We're working on it. 🤠