Keith Powell orders the seafood stew, bonds with our waiter as if they’re old friends, and seamlessly swaps out the mussels for some extra shrimp. I take note: in NYC, even the simplest of menu tweaks can be perceived as a nuisance or a slight, but Keith orders with graciousness and a deep laugh — so much so that our waiter circles back throughout the meal to trade jokes and schmooze, even during a swamped lunch hour. When you get an impression of someone solely from a modification to gumboed prawns and shellfish, it stands out.

Of course, I had a clue that Keith might be awesome before meeting him. His series Keith Broke His Leg effortlessly braids comedy and commentary together, capturing the nuances of everyday life and punctuating them with several LOL-worthy moments. But you never really know what to expect from an interview, particularly when the subject has made a name for himself in 30 Rock, alongside the likes of Tina Fey and Alec Baldwin. Maybe they’ll shrug off your questions, or answer you with the monosyllabic enthusiasm, or be so impacted by the haute hokum of Hollywood that you leave feeling kind of sad about the human condition. But as is reflected in the show, Keith is much deeper, and way more fun, than all of that.

Navigating through 30 Rock to married life to the art of creating a meaningful story, Keith chatted with us for more than three hours to talk about his new series. Here are excerpts. And wow, it was hard to get it down to these excerpts.

How did you come up with the idea for your web series?

I feel like it was created out of a want to share my life in an artistic way. I was recently married, I bought a new house, and my life was changing. I had had a minor operation [and] was incapacitated for a week, and during that week all the things that I had previously learned I had to kind of relearn. The show is about a man who is relearning how to live his life in a new environment.

In one episode your character says, “Web series are so overdone.” Is that something you felt before starting the show?

Absolutely.

So what made you come around to actually making a web series?

There’s such an oversaturation in the market. I never wanted a web series to be viewed as a showcase for my work, I wanted a web series to viewed as telling a story. And what worried me was that I didn’t know that people would be open to hearing stories, or if they could hear a story because of all the noise of other web series. So, what brought me around to it frankly was Vimeo. Vimeo has a very unique platform where it’s about the work and not about the promotion. And [that’s] something so helpful to an artist, to have a tool that helps you continue your art. When [I realized] that there was a way for Vimeo to help me tell a story, rather than to help me just promote myself, that was kind of a gateway or lightbulb moment.

And we’re really happy to have you!

I’m really happy to be here!

You touch on race several times in the series, notably in the episode “Baller,” where with your agent asks you to “talk more black” for a part.

Right, be more urban.

Was it important to you to create a series so you could control the ways in which you are portrayed in the media? What kinds of conversations are you aiming to spark along those lines?

What I really wanted to do is normalize anti-stereotypes, if that makes sense. I mean it’s a very heady thing to say. But all that basically [means] is that people are afraid of what they don’t know and what they don’t understand. And when they’re afraid of what they don’t understand — in order to quell that fear — they want to control it, and they want to put it in a category that is familiar and palatable to them. But the problem is is that people who are unfamiliar to them then become only a representation of what the majority sees. So you then never get to be your individual self.

My goal with that is if we do a little discovery of truth in each episode, that’ll build up to be a wider truth, so that you understand the entire person rather than just the stereotype.

In terms of this show coming together, you created, wrote, and directed every episode. Can you talk about the interplay between all of those things?

It was very difficult. I wrote an Indiewire piece about juggling all those hats and the biggest thing that I have learned is to give yourself as much time as possible. There was never any kind of pressure to get it right the first time. I made a lot of mistakes. There are still a lot of mistakes in the show, but I kind of walked it back, and that is with each hat — I went back and [asked] how a director would tell the story, how an actor would, and how a writer would.

So piggybacking off of that, what advice would you give to creators?

Story is of paramount importance. So many web series are used as self-promotional platforms and therefore they lose the story in it. And people connect to characters, people connect to situations and environments, and not so much of the performer showing how talented they are. The advice I would probably just give is to be sure that you’re telling a story that can connect and that you’re passionate about, and then all the other things will fall into place.

Aubrey Plaza has an awesome cameo in your show. How did that come about, and do you have any dream guest stars?

Aubrey is like my little sister. I’ve known Aubrey since she was about 12. There’s a contingent of Delawarians who all work in the industry and have various levels of success, and we all did community theater at the exact same time. And I was the oldest of them all, so they’re all like my little kids. I sent her a text message, and literally it was just like a Friday night hang out with Aubrey and Seth [(Lipstick Jungle, 30 Rock)]. That’s the only time in the series where dialogue has been improvised.

Who would be my dream guests? I have a lot of friends who are on big TV shows who’ve come up to me and said they’ve seen the show and they’d love to be in it if the timing works out …  but if Alec Baldwin finds himself in my neighborhood, he’s always welcome to come in and shoot an episode.

We pulled some fan questions from the nets. @BlondeCircus said they loved the tone of your series, which is really funnny and finds great quiet moments as well, and asked if that’s a hard balance.

Yes!

Can you elaborate?

I know that a lot of comedy is louder, faster, funnier, but I don’t feel like you earn your jokes that way. In acting school they always talk about earning your pause, and I feel like with this show it’s about earning the joke. The balance [of] the quiet moments and the funnny moments is very much about walking that kind of tight rope. And that’s the way that we connect to a story.

@andrewstuhl wanted to know how you and your wife Jill handled the work-life balance, given that your life became your work.

It was difficult at first, but the entire conceit of the show is to expose my life. So it scared me to have that happen, because it’s scary to see that I almost got caught masturbating once!

Jill also is a person that has also freely admitted that she doesn’t like to be directed … by her husband. I feel like the work-life balance is just little things, where I try to just give her an idea of what’s going on in my head, she tries to execute it, and then we walk away from it and have our own life. Honestly it’s about jumping in with as much information as possible living in that little microcosm, and then walking away.

@KimiSchmitz asked how long the writing and pre-production took before you actually started filming.

Again, I gave myself an unnaturally long time. Pre-production was like, two months. I gave myself a month to write it. I gave myself another month to do pre-production. I shot it over the course of two weekends.

Lastly, from @jonathan_stuhl, how do you begin writing the script?

Every episode begins with a truth that I want to reveal and I work backwards. [Take] the “Pornhole” episode: there was an article that I read about how when you’re in a relationship, your partner gives you some sort of a line, and then you have to reciprocate, and the amount of times that you reciprocate based upon whatever [that line may be] dictates how successful your relationship is. Couples who divorce might say something stupid like, “Oh my God, I think I’m gonna go grocery shopping today,” and that’s a line to your partner [for] reciprocation. So I read that and it reminded me of the time when I started going, “Oh my God, she wants to connect and I’m not connecting.” That’s the truth I wanted to reveal in that episode.

[Then] I thought, wouldn’t it be hilarious if I wanted to do a solo thing? Like, I wanted to masturbate, which is all about me doing my thing, and I’m being forced to connect but all I want to do is just, you know, worship myself. So those heady ideas begin, and then you start think about times in your life where that has happened, and that all kind of gets built together into a storyline.

What’s your favorite episode?

I think that the newest episode “Mellow” is my favorite. And it’s just because in my mind it crystallizes an idea that I’ve always had and have always been trying to fight for — a story that has an arc, that has a beginning, middle, and end, that is both political and personal.

In terms of the next six episodes coming out, what can people expect from that and what are the plans for the feature? Is there a season two, or what would you like this to become?

I have an idea for about 25 more stories. So as long as I can afford it, I’m going to keep making them. People really seem to really love the dynamic between Jill and I, so I wanted an episode that was just the two of us. It has a pretty emotional and very true ending that reveals an intimacy about our marriage that I’m eager for people to see, but it frightens me tremendously. That comes out on Valentine’s Day.

Oh God, one of the funniest scripts I’ve written is coming out where I teach high school students how to act and they do the worst racial stereotypes of all time. And sitting there trying to get these very shy high school kids to be so awful with racial stereotypes was my crowning achievement as a director.

Then I wanted to do an episode about the straight man/ gay friend dynamic, so that’s coming out. “Soothsayer” is such a model for what I want the rest of these how to be because I want to balance thoughtfulness and comedy.

We do hope for a season two!

That’s kind of the idea. Because it takes about a day and half to shoot each episode, and frankly it costs about $600 an episode — plus dinner.

Last question. If you were me, what should I be asking you that I haven’t asked?

Oh boy.

You don’t actually have to pretend you’re me.

That’s a good question. Oh f*ck. What do I want people to know about the show? There’s a lot of thought and care that goes into it. And a lot of me and a lot of my emotional life. It’s incredibly personal. I don’t want people to watch because I want them to know about me so much. I want them to watch the show because I think that it’s a comedy that reveals truths that are very self-reflective.

And I’d like to encourage the world to be self-reflective. I don’t think that we have enough empathy. I don’t think there’s enough admitting what our strengths and weaknesses are. And I think the show is [one] that very much that celebrates confidence, while also celebrating the work of trying to be a better person. So that’s what I want an audience to get out of the show.

Thanks for sharing and visiting HQ, Keith!

Catch up on all the episodes on Keith’s channel, which will be the home for all soon-to-be released videos as well. For more peeks into the creation of your favorite videos and series, delve into our highly useful “Behind the video” archives.