By Cailey Rizzo

The greatest thing about New York is its creative web that lurks just below the surface. You never know when you're going to meet someone who will get you involved in a project that will change your life. Hillary Nussbaum, whom TLD recently interviewed, knows all too well the chance creative encounters of the city.

Thanks to some courage and a much-loved coffee shop, she is now the writer and producer behind an upcoming web series. The series, based on the lives of 20-somethings in the city, is now seeking funding on Seed & Spark. But her series focuses on something interesting: maintaining old relationships when everything – even the technology – is brand new.

We met at Irving Farm, one of Nussbaum's favorite spots, and talked about our city's creative scene, how to maintain old friends in the digital age and why great things always happen at New York coffee shops.

Cailey Rizzo: So how did this all come about?

Hillary Nussbaum: I used to work in reality TV, in development, coming up with shows and then package and pitch them to a network.

C: What sort of shows were you doing?

H: Cooking shows and travel shows. I worked for a production company and that was one of their specialties. And it was really awesome and really fun and I liked it because I got to do a lot of different things, but it really wasn’t speaking to the writer in me. What I always wanted to do was write for television.

So I left that job and just decided that I would take a year and write and see where that got me. So I wrote a few spec pilots, original pilot scripts, and seemed to get pretty positive feedback but was frustrated with the fact that a script only goes so far, only so many people read it. And I didn’t feel like I was learning as much as I wanted to be learning about putting together something that an audience can actually watch. So I decided that I was going to write a web series.

Keep Me Posted / Taylor Stanton

C: And how long was the process? How long did it take you to write and then when did you start producing it?

H: “Write” is kind of hard to define. Because before I really committed to the project, I was writing scenes and playing around with characters and scenarios. Figuring out what I wanted to do and then developing the concept that way. But I think from the time I really settled on the concept and really started writing it in earnest, the pilot probably took two or three months.

C: And how did you find everyone that you collaborated with for this?

H: So, it’s kind of a funny story. I used to live near the other Irving Farm on the West Side. I used to write there all the time. And I was sitting at the big, communal table and these women at the end were talking about a production that they were crewing up for. And they seemed approachable, so I decided to go over and talk to them.

I had just left my job in reality TV and I told her that I had a lot of friends and we were looking to work on short films, scripted things, and if they needed crew recommendations, I could pass along some resumes. So we exchanged contact information and I totally forgot about it. And a year later, they emailed me like, “Hey, we’re finally ready to start working on that film. Do you still have people you could send over?”

So I said yes and I passed them some resumes and said, “Hey, I’d also love to get involved. I’m a writer and I’m looking for set experience.” So I ended up working on a short film with them in November. I was the script supervisor and production manager.

For that, they rented a house for five days and the cast and crew lived and filmed there. And we hit it off. They’re a really great bunch.

So, those were Pitch Her productions, the women sitting at the table that I started talking to.

C: And what exactly is it that you hope to get from the Kickstarter money?

H: Really, we want to make it the best series it can be. We want it to be well-lit and to sound nice, so we have equipment we need. But it’s also really important to me, and to the rest of the producers, that we’re compensating the people involved. It’s really amazing that everybody believed in the project and really wanted to work on the teaser and I want to be able to compensate people going forward.

C: And why did you choose web series as opposed to another medium?

H: It’s doable. TV is awesome and ultimately where I’d love to be, but web presents this unique opportunity to do it yourself. If I were to get really lucky and sell a script to a network, I still really wouldn’t get to make it. Whereas with a web series, I can be really involved in all aspects of it. I’m really excited about all the learning opportunities that that presents.

C: And now, delving more into the ideas behind the material, where did the idea come from?

H: It sort of started from this moment where it felt like everyone I spoke to was going through, or had just gone through, a falling out with an old friend. And I felt like there’s this moment, maybe in your mid-20s, where you’re changing really quickly and it’s affecting your friendships. And sometimes those friendships evolve and sometimes they don’t. And I wanted to look at that moment but it took a while to find a way to do it that wasn’t just really sad.

So, I had that idea just sitting in my mind for awhile while I was working on other things. And then I wanted to play around with texting and social media, and sort of married those two concepts and ended up with this.

C: There was something where you were saying staying connected isn’t the same as having a connection. And I was wondering if you could speak a little more to that phrase and where that idea came from.

H: That’s really the crux of the series. While I was going through all these friend adjustments, I realized that everybody had a very different standard of communication and what they wanted. Whether they expected two phone calls a week, or constant G-chat, or an occasional text. And I was thinking about that. Whether your friendship should be defined by how you communicate and how often you communicate.

Because I have really, really close friends who I don’t talk to all that often. And then you do talk to them and it’s like you were never out of touch and you get right to the deep, important stuff and it’s great. And then there are the friends that you talk to constantly but it always stays at that surface level.

So I was really just thinking about that and connection and connecting. And I had this really weird moment where I did have this close friend who I did constantly talk to and I was in a weird place at the time, so it was partly me, but we would get together and it would be this big mental investment to interact with her in person. And it was so strange. So I started thinking about that, too. Like, why is that so different?

C: It hit home because I just had this happen: How you can be in such constant communication with someone you’ve known for your entire life and then you see them again and it’s like, “Woah, we don’t relate to each other any more. Even though we’ve been talking and I know everything that’s happened in your life and you know everything that’s happened in mine.”

H: I will say, that friend, we’re still really good friends, it was just an adjustment. But then there are those people who know all the details. Because you’re constantly catching up and filing each other in, but you’re not really…

C: Like, what you did versus what you're actually thinking?

H: Yeah, I want to say, you’re not analyzing things, but you probably are analyzing. What people said and what people did.

C: “What does this text mean!?”

H: Exactly. It’s just not the same.

C: One thing I’ve noticed recently with a lot of people I’ve been talking to who are also writing, and I noticed it when you were talking about your show, I think comedy now is so absurd. And everybody loves pointing out the absurdity in life. I was wondering if you could talk a little bit about how absurdity plays into your style of writing and if you think that the digital world affected absurdity at all.

H: Well, I think like most things, comedy is cyclical. And I think that for a while we’ve been moving away from the laugh track-y sitcoms and the response to that is maybe the subtler, more down-to-earth comedy. I think the Internet loves snark and loves irony. And maybe that was part of that change?

I think it does play really well on the internet, which is maybe why it’s right for a web series. But I’ve also always found comedy in weird places. And laughed at things that other people don’t even notice. But it’s interesting because now there’s a reversal of that trend, back into that earnest, bright, technicolor comedy in really fun, awesome ways that still are a little snarky. It’s fun to see how it’s evolving.

C: Are there any things that you’re directly influenced by or were drawing from for the series?

H: Really just life. There are a lot of shows I watch and a lot of shows I love and try to emulate. But if I told you what those shows were, you wouldn’t see the connection between what they are and what I’m doing. It’s really hard just to find one or two.

C: Or were there any things that were really quintessential in forming your brand of comedy? Things that resonated with you?

H: It’s funny because I feel like a lot of the shows that really resonated with me, resonated because they had heart and character development. What’s coming to mind are more dramas, or dramedies. Things like Parenthood or Friday Night Lights which you did find the comedy in, despite it manipulating your emotions every week. There are the shows like Crazy Ex-Girlfriend or Jane the Virgin that are really smart about their social commentary. I like to think that I try to emulate them in some way.  But they’re amazing, so I won’t pretend…

Keep Me Posted is accepting funding until July 29. You can donate to the project here.