Why You Should Be Terminally IRL with Ben Winn

**David Nebinski** (0:04)
Hey, friend, it's David Nebinski here in Brooklyn, here at the Portfolio Career Podcast, where we take ownership of your career and design a life that you want to live. This conversation is with Ben Winn. He's the VP of Community and Content at Firstmark here in New York. We first chatted in late 2025, and I loved the chat. On LinkedIn, I love his takes and ideas about community building, hosting events, and more. He's created a website with some of his ideas at terminallyirl.com.
Check it out. There's lots of good playbooks and more in there. And on this episode, we talk about this, the thesis behind terminallyirl or terminally in-person. So if you're hosting events, this episode is for you. The video of this episode will be available as part of my newsletter that you can subscribe to at davidnebinski.com/newsletter. Excited for you to build and grow your portfolio career. Here we go with Ben. Okay.
Ben, welcome to the show.

**Ben Winn** (1:00)
Thanks for having me.

**David Nebinski** (1:02)
It was funny. While we were getting started, you were asking me how was Tech Week? And that was like what I wanted to start this conversation on about in-person events, etc. And I shared that I wasn't that active, but yesterday was an active day for me.
What was it like for you?

**Ben Winn** (1:25)
This week has been chill for me. I feel like there's more happening, but I don't know if it's necessarily more quality. It's just like the volume is a lot more this year than any other year. This is the first year I'm not running a big tech event. I've attended a couple.
So I had a very cool dinner last night that was very small and intimate. I love that kind of stuff, but I actually have done, I probably should be going to more stuff this week, but I'm also planning a big summit that's 10 days away. And so anytime I'm not working on that, I'm either trying to sleep or squeeze in a couple of things.

**David Nebinski** (1:59)
Okay. Did you have, so I want to talk about this Terminally IRL, Terminally in-person.
Got a new website about this and you're calling it a thesis.

**Ben Winn** (2:13)
I'm in VC. I have to call any idea I have as a thesis.
But it's just literally a blog post. It's an idea that could probably be a tweet. But the idea is that has been bothering me, is that a lot of job postings have been requiring you to be terminally online. It's like this thing of being encouraged to be terminally online, and we're looking for someone terminally online. And I get the appeal, right? Of like you want someone that's aware of what's happening in the world.

**David Nebinski** (2:42)
Yeah.

**Ben Winn** (2:43)
But I think that's kind of a baseline for anything now, like in terms of just being aware of what's happening. I think the real edge comes from being in-person. And so my idea slash thesis is terminally IRL. And I would call it a thesis because it is positing that that's the future of like where a lot of energy is going to be directed into as online becomes noisier and noisier. You know, bots just overtook human traffic for the first time ever the other day.
You know, even with like Tech Week, there's 500 plus events or maybe a thousand. I forget even the number. It's harder and harder to even know what to go to. It's hard to know who to engage with. I put out an announcement today. So we did a NASDAQ billboard feature for our summit in two weeks. And half the speakers or their teams wrote to me being like, is this AI or is this real? Because like there's no one believes anything anymore. And I had to be like, no, here's the video. Like I was there. Here's my selfie of the thing. Like it's real.
And so I just think as the world becomes noisier, the real signal becomes in person. And so more people, more companies, everyone's going to start devoting more time and energy to in-person experiences and being IRL. And so I think by being terminally IRL, you get much more of an edge than you do being terminally online.

**David Nebinski** (4:02)
So wait, the summit people think is real. But...

**Ben Winn** (4:07)
Yeah, they know they're coming to speak on a real stage with real people.

**David Nebinski** (4:10)
Yeah. But just the photo of Times Square, Billboard, yeah.

**Ben Winn** (4:14)
I mean, because you can AI that stuff now. Like it's very easy to go in and be like, put me on the side, turn the Statue of Liberty's face into mine, or whatever. You can do anything you want.