More Human Than Human: Using AI to Connect to Actual People

“A phantom in a box, shadow in your head.” — White Zombie

Nobody ever asked for VCs to start quoting song lyrics—but if you’re going to, it might as well be someone happily partnered for 20+ years, a longtime vegan and animal welfare advocate, and known for being professional and kind to crews and fans.

Rob Zombie > Kanye

People are usually surprised to find out I'm a Rob Zombie guy. I’ve seen him live, as well as Marilyn Manson, and Rammstein. That's not the expected profile of someone who writes about pitches and startup boards. It's exactly that kind of detail, by the way, that gets strangers to write to you. Nobody ever sent me a personal note because I'm a VC. They send notes because of the specific, slightly off-profile human things I put out into the world.

The quote is from “More Human Than Human” which is the corporate slogan of the Tyrell Corporation in Blade Runner, which builds replicants—machines convincing enough to pass as people.

Rob Zombie borrowed a lie about machines pretending to be people. I'm going to use it to say something about people can use machines to be more human.

Two weeks ago, I got a cold email from Earnest Sweat. It opened with "We've never actually met." In the note, he referenced that on October 12, 2016, I did an 8pm video hangout for a group learning about VC, and Earnest was one of the people on that call, trying to break into venture with no idea how.

Ten years later, he's raising his own fund, and he wrote to tell me. We caught up this morning.

How did he know I’d care or reply?

What probably made it safe was twenty years of writing that reads as an invitation instead of an instruction. If I only published one sided, authoritative pieces telling founders what to do, the only thing that invites is disagreement.

Instead, I get a lot of "I've been reading what you've been writing, and I'd like to connect." Earnest knew I coach investors. He knew I'd be receptive before he ever hit send. Ten years of public silence or only reposts of portfolio company funding announcements and he probably never reaches out.

For me, content has always been a means of creating, and more importantly, inviting connection.

Yet, people assume scaling your content with AI (the slop cannon) will do the opposite and make the internet less human.

It’s an issue I’ve thought a lot about as I’ve developed this small quarterly cohort of a handful of folks called Visible Work.

We're about to run another cohort of Visible Work in about a week (we have a couple of slots still open) and I've been forced to think hard about what the thing I'm teaching even is. I know enough not to think of it as “thought leadership”, so I had settled on the idea of making your accomplishments more visible.

Visibility, though, in a world of AI, has begun to feel too much like an attempt at cutting through with more—more posting, more thoughts, more slices and dices. Thanks to AI, we’re drowning in more, and it’s becoming less personal.

I want more human, and better connected, yet somehow in less time.

That’s what I think we’re teaching now—using AI to make it count and have accountability to be intentional about how you connect. It’s about finding the Venn diagram between who and how you’d really like to work and using the tools to get organized and accountable around it.

Here's an example.

For years, I'd send out a personal update to a list of a couple hundred people I curated by hand — it’s something we do as a project in Visible Work.

Replies would come in, and then life would get in the way, and those replies would sink to the bottom of my inbox and disappear. The most meaningful part of the entire exercise, actual humans actually responding, got dropped too often. Now, my AI Chief of Staff captures every reply and holds me to answering them. Yes, the email is mass, but the people who engage with it get more personal interaction than they used to, not less, thanks to AI.

My social media project manager, also an AI construction, caught something worse. I had a draft of that email ready to go, and it pointed out that I never once asked anybody how they were doing. A letter whose entire purpose is staying connected, and I'd written the whole thing about me. That got fixed before it went out. I write content as an invitation to connect — or at least I say I do.

What I learned was that the most human thing, or the ideally human thing, was screening everything against that filter of my values and intentions.

I've stopped trusting myself to be the only screener, rushed by a five year old who can brush her teeth, but still wants me to, using funny voices for the characters on her brushes.

Humanness in AI also comes up when we're building the invite list for our annual 400+ person tech party—an event I’ve been curating since 2008. I ask: who am I not thinking of that should be here? Who are the design people, the people who actually made New York tech what it is, the folks from my inbox and calendar I've engaged with this year who should be there? Someone could say the thoughtfulness isn't really mine if a machine is doing the remembering.

I'd flip that.

The thoughtfulness is knowing that I will forget people — everyone does — and using a tool to make sure I don’t.

Sometimes the connection runs backwards through the machine. Someone I met at a coworking space ages ago — lovely person, but not a super close professional contact — replied to my last update saying her family grabs an off-season Airbnb with a few other families for a weekend — board games, no agenda. That reply turned into a conversation in my own house last night about which families from my daughter's school we'd actually do that with. Now we might do it. A mass email produced an idea for a better friendship in a 1:1 exchange.

Now for the part I can't do yet, but want to.

I lost my dad in December 2024. This past year, a fellow dad I know lost his. I happened to be at a playground next to his building this week and thought, I should see how he's doing. I should just ask him to coffee. The only reason that surfaced was geographic accident.

What I actually want is a screen, or even better, a serendipitous nudge: who in my network just lost a parent? Who just lost their second? Those are conversations I have a lot of thoughts about and continuously deal with, and I would show up for them.

Would I create a WhatsApp group for the other orphans in my network? Maybe. I'd never thought about it before this week — the idea came out of talking it through with Claude by voice while my daughter climbed some monkey bars quite independently and without help, as she prefers.

That’s another hack we talk about in Visible Work—time shifting. No one has time to sit down and write against a blank screen, but a voice chat with an AI? I’ve done it at midnight on the way back from Beer League ice hockey games—reclaiming otherwise lost time to do things that connect me better and yes, make me more visible.

Here's what gets me: the platforms have this data. Facebook knows. Instagram will show you the post, and then there's no next step, no way to act on it. I'd argue Meta is even incentivized to build it — if Instagram said, “Hey, this is the 4th person in your network to lose a second parent, as you have—would you consider creating a WhatsApp group for them?

I would engage with that support group for years—and I’d certainly rather be doing that than leaving angry comments on Bruce Blakeman posts, none of which I asked for, but some Meta PM decided I needed to make their dashboard look better. Rage got them a few clicks before I ultimately blocked him for my own good, but the Parentless group would have kept me for a decade.

They build the rage machine anyway, probably because the median Meta product manager probably hasn't buried a parent yet, and tech generally overindexes for guys who never cried in therapy.

Which brings me back to what Visible Work is actually teaching, because I hope that it’s nothing like what people assume a thought-leadership course would teach. Publish what invites, not publish more. Track who you owe a coffee, not your posting cadence. Measure whether someone replied and whether you replied back, not impressions.

It’s been a work in progress over the two years I’ve been doing them and this time, I want to push these levers even more. Some weeks, the most important "visible work" isn't writing anything — it's the twelve coffees over three weeks that create the conversations worth writing about later.

If you’d like to join a small group of people who have decided to care about who and how they work, and are willing to use some tools to scale things that have a net effect of better connection to humans who can create opportunity, join us at Visible Work to build a connection engine, not a content engine.

In what ways have you used AI to keep you better connected to humans? I’d love to hear your tips. Funny story, but a young VC I know told me she found her dad’s ChatGPT account and it was full of searches that helped him engage in better conversations with his wife and his children.

I’m not crying. You’re crying.