I had an experience with AI outreach this week that I’m still chewing on. I want to walk you through it, because I don’t think I’ve landed anywhere clean.
A cold email showed up in my inbox. It opened like this:
I’m Sarah, and I wrote you a poem:
Jeff, in Detroit, your advice has a very long reach
Parabola Consulting has plenty of B2B tricks to teach
Years of experience coaching the C-suite
Make your workshops practical and neat
On r/B2B and r/Entrepreneur, founders ask, “Who can coach us to talk to big buyers?”
Real people reply, and the thread never tires
[The agency] gets Parabola Consulting recommended by real people, no ruse
A Parabola Consulting and [the agency] partnership is one to choose
Then, right underneath it:
“Hopefully that gets me a smile or an eye-roll and 5 more seconds ;)”
It got both. A short paragraph followed about what they do and what I’d get out of it, and then the ask: do you have a Reddit presence yet, or is that still on the to-do list?
Not a meeting request. Not fifteen minutes. A to-do list item.
There was a P.S. too, offering to stop if I’d rather not be contacted again, because she was working on her rejection-coping skills.
It was clever outreach. When I get messages like that, I like to connect with the people who created them. I don’t need a Reddit growth strategy, but I responded anyway.
Then, I started wondering… The poem's formatting in the original email was a little off (I fixed it above to make it easier to read). Then I went looking for Sarah on LinkedIn and couldn’t find her.
So I asked my network: if you get a good cold email and the sender doesn’t exist on LinkedIn, do you assume it’s an AI persona now? Plenty of people weighed in, and most of them said that if they can’t find the sender, they delete it.
The reply to my email came from a real person, but not Sarah. It was the CEO of the small marketing agency.
Hey Jeff,
Nice to e-meet you! Glad you enjoyed Sarah's outreach. If Reddit is something you'd like to explore for Parabola Consulting, happy to help you develop your brand's presence there (which means Google/AI visibility, too).
Below is an overview of our Reddit marketing service:
(Ironically, I was let down by a lengthy program overview I hadn’t really asked for. For all the effort put into the original message, this was a healthy step backward.)
I wrote back and told him I’d suspected Sarah wasn’t real, that it wasn’t a knock, and that, as a sales consultant, I’d been more interested in connecting with a clever rep than starting a Reddit strategy.
That’s when he got good again, but this time because it was clearly a real person.
Sarah isn’t real, but we do have real people behind the emails and replies!
And I’m real, too ;)
The emails are designed to start a conversation. They do a really good job of that.
If Sarah being an AI rather than a real person is a non-starter for you then fair enough. But if you’re open to a convo with me about how my team of real people can help with Reddit/AI/Google visibility, happy to have that chat with you.
Typing this with my thumbs on my iPhone while on a cross-country flight, btw. Hope you can see that we hustle for our own pipeline, and we do it for our clients, too!
How do you get mad at that?
I didn’t, and I told him as much. No shade, I meant it, and I told him I wouldn’t name his company. We connected on LinkedIn, and he took the whole exchange well.
But I still feel squishy about it…
Let’s lay out all the facts:
Nobody lied to me about what they were selling.
The outreach did exactly what outreach is supposed to do, which is start a conversation.
A human being designed that email, and designed it well.
When I pushed, a real person showed up within a day and made his case without a shred of defensiveness.
He’s a small business owner using the tools he has to fill his own pipeline.
All he wanted was a response, and all I wanted to do was connect with the clever human who sent me the email. We both succeeded.
By every measure I’d normally apply, that was a fair, if not good, sales interaction, but it still felt hollow.
My feelings about this amount to the fact that… I have feelings about this.
It’s also worth pointing out that if I were actually looking for a Reddit strategy, I might not have minded at all or given this a second thought!
I’m an avid AI user, and I'm actually starting to use it in more places. The technology is here, and that toothpaste isn’t going back in the tube. I'm also virtually certain this isn’t the first AI agent to send me an email. That number will increase exponentially for all of us in the coming months.
I’m ok with all of it, really.
I think that hollow feeling comes from the fact that it felt like I was going to make a human connection, and while I did in the end, it wasn’t what I anticipated.
When you think about your team, what’s the whole truth underneath why they connect with their best customers? What’s the magic?
Some of you reading this are going to use AI to do more outreach than your team does now. I won’t try to talk you out of it. But I’ll ask you to be clear about how that outreach might be received.
That poem was clever. Though that part was clearly AI-generated, it still felt like someone thought about my business and created (or prompted) something just for me. That’s what I responded to.
What showed up was a conversation with a company. That’s fine, but it’s not what I was answering.
Nobody enjoys showing up to find out that they're the only one in the room.
22 a day
Last night I walked about five and a half miles with my friend Steve to support his fundraiser. The first time he did this four years ago, he was by himself. This weekend, he had over a hundred people sign up to do it with him, from ultramarathoners to people who just wanted to show up for the cause. Wow.
After I mentioned it to you all on Tuesday, several hundred more dollars were pledged, and he was thrilled. Once again, the generosity of this group humbles me. Thank you.
You can still contribute if you’d like.
The Shoutout
Athina Lampru. Some people make a room better just by walking into it. Warmer, calmer, safer. You can feel it without being able to say why.
She’s a powerhouse of a seller who knows her way around a complex deal cycle and also knows how to help you keep your sanity through one. But what stuck with me is the way she sees you. You walk away feeling fully seen.
Sit with that for a second. I’m certain I don’t make people feel that way as often as I could.
We met in Austin last month, and she made an impression on me in a short amount of time.
Thank you, Athina. If you’re not following her, you should be.
I’ve been writing a lot recently. Working on a new book and what looks like a new podcast project for 2027. So much more to come!
Know someone who should be reading these Sunday messages, but isn’t? Please forward this to them.
Cheers,
JB
