Phil Augusta Jackson is recommending perhaps the best wine pairing of all with his series “Grand Crew”: friendship. Inspired by Jackson’s real-life experiences, the sitcom — which airs Fridays at 8:30 p.m. ET on NBC — is more than just a wine show. A little over a decade ago, Jackson moved from New York to Los Angeles for a writing role and often met up with colleagues at L.A.’s Covell wine bar. Through frequent visits to the bar, his knowledge and appreciation of wine grew almost as quickly as his relationships with the friends he met there.

Discussing the details of his life and building community over a glass of wine has contributed to much success for Jackson, including a few Emmy nominations for his work on “Key & Peele” and “Insecure.” Now in its second season, premiered March 3, “Grand Crew” is ready to expand the audience’s palate with new laughs, loves, and real talk from Nicky (Nicole Byer), Noah (Echo Kellum), Sherm (Carl Tart), Fay (Grasie Mercedes), Wyatt (Justin Cunningham), and Anthony (Aaron Jennings).

Jackson sat down with VinePair to discuss his journey into the entertainment business and how a casual discussion about his weekly visits to a local hangout led to the creation and running of his own show.

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1. What was your first experience with wine?

So, my very first experience with wine would be with my parents. They’re not big drinkers at all. They let me have just a little taste on New Year’s Eve. We would go to church, then come home and they would have half a glass and they’d be like, “ Hey, you could taste a little bit of this.” It was probably Champagne or something like that, you know what I mean? And then after that, I think in college it was boxed wine at fancy Franzia parties.

2. ‘Grand Crew’ is a play on the French wine classification ‘grand cru.’ How did the show get from vineyard to bottle?

Dan Goor, creator of “Brooklyn Nine-Nine,” pulled me aside at the end of Season 4 and said, “Hey, we have a pretty good dynamic. If you ever want to develop, let me know.” If someone says they want to collaborate, I will. I’ll do it. We started meeting weekly to throw around random ideas. One day before a meeting, he asked me what I was up to. I told him I went to this wine bar with my friends. That became a weekly topic at our meetings. At a certain point, we were like, “Wait, this might be the show.” So that’s how it happened. We put it together and sold it to NBC.

3. Did you go to school for film, writing, or acting?

No. I went to undergrad at the University of Virginia in Charlottesville to study business at the McIntire School of Commerce. I majored in marketing and management. I went to an advertising agency in New York right after college and did what’s called strategic planning/brand strategy. Basically a lot of research and analysis, conducting focus groups, and distilling insights through consumers. A couple of years into doing that, I had always wanted to take an acting class. I started one and then I found UCB (Upright Citizens Brigade Theatre) and started doing improv. Once I found improv, I was like, “I think I really want to try this performing thing. Let me do this.” I ended up writing a play, which ran off-off Broadway for like a year or so. Soon after, I got an agent and then things just started to happen after that.

4. What led to your transition from acting to writing?

In 2008, I started taking acting classes to pursue that and just to see what would happen. I would have these three-hour classes and there was this guy, his name was Jed. He would bring these little short, tiny, two-page plays and if you wanted to stay later to be a performer, Jed would let you act in them. I would stay and do Jed’s plays, and then I was like, “If I bring in pages, does that mean that I can also just workshop stuff and people can stick around if they want to?” I immediately started bringing in a scene every week, and then after about six, eight weeks, I had a one-act play and thought, “I guess I’m a writer now.” I rewrote that play, which is the off-off Broadway play I mentioned earlier, and ran that play for about a year. At that point I was just writing because I hadn’t booked anything. But then I started doing UCB stuff again while I was auditioning for pilot roles. I’d go to NBC a lot in New York and eventually I was like, “Well, I’m not booking any of that, either, so let me write a pilot.” I showed it to my now-agent and based off the script, she said, “I’m going to start representing you for literary.” “Key & Peele” happened a couple months after I signed with my agent. I wrote a packet. and they picked me out of a pile.

5. How did your experience on ‘Key & Peele’ lead into ‘Brooklyn Nine-Nine’?

I wrote on the last two seasons of “Key & Peele” before I got my first narrative job on a show called “Survivor’s Remorse” on the Starz Network, run by Michael Morley. I was thinking about what the next move could be, since getting that first narrative job after having a sketch job can be kind of difficult. I was a huge fan of “Brooklyn Nine-Nine,” but I was concerned there would be questions as to whether or not I could do narrative writing. I anticipated based on my “Key & Peele” and “Survivor’s Remorse” experience that my role would be joke writing, which is a strength of mine. But what I learned on “Brooklyn” was that the attention to story is actually first and foremost, and then building the comedy around that happens after. You laugh at the jokes because you can follow the story very easily. It felt great to just learn the process to create stories that you can follow and to actually have fun with that. Basically, it was a master class for four years, doing 20-plus episodes each season.

6. You keep successfully pivoting and building on opportunities put in front of you. Now you are a show runner. How intentional are these decisions?

While I was in New York in the improv scene, I didn’t really know what a show runner was. I knew that I liked to write. I knew that I had a pretty good natural inclination to get stuff on the page. I think I knew I wanted to be in entertainment. My philosophy is just to work as hard as possible and to learn as much as possible. Because I had a lot of interests growing up, I know that at any given moment I could find something that really makes me passionate. Consequently, I wasn’t one of those people that feels like if it’s not acting, it’s nothing. I said, “I’m really interested in acting, but there’s something about this world that I’m really attracted to, so let me try and figure out how to get into this world.” I think it’s going to be acting. Then I write a play, and then that play sells out and OK, I do the math. I’ve been doing four shows for a thing that I wrote at the end of an acting class for about a year. I think I might start writing a little bit more. I’m not going to stop acting, but I’m going to continue writing. Then I write a pilot and my agent says, “OK, I really like this.” Then I get “Key & Peele.” I think part of it was just putting myself out there. At any given moment, I think I would have not done it if I really didn’t like writing. But it turns out, I love writing. I didn’t realize how much I loved it until I had these experiences. I do say to myself, I want to work harder than the previous year and then I want to see what opportunities open up for me. If those opportunities speak to my heart, I’m going to lean into them. I’m going to go as hard as I can after them and that’s been my guiding principle. Once I found out what a show runner was, I really wanted to be a show runner. And that was the thing that was driving me. Each job is like, “OK, how can I be of value in this room and how can I learn as much as possible?” In the hopeful eventuality that I have an opportunity to sell a pilot. And that’s what ended up happening after I worked on “Brooklyn.”

7. ‘Grand Crew’ is one of the few shows with an all-Black cast highlighting a wine industry that also has a paucity of representation. Did you think about that when creating the show and/or in constructing storylines?

I think when I hear it that way, I’m like, oh, that’s a lot of pressure. Oh my gosh, that sounds like a lot. But I think the good thing for me at least — the thing that keeps me from going crazy — is that the show is inspired by my real life. I just discovered wine and was existing in a space where there weren’t a lot of people like me, but I built some of my closest friendships in this space. So, there’s some real interpersonal dynamics and friendship dynamics that you can relate to, irrespective of what color you are. But I am a Black man. I’m not going to ignore that, right!? So, I think when creating the show and then the first season, it was like, OK, how do we talk about these Black issues but not be super soapboxy about it? How do we speak to human nature, friendship, relationships, etc.? So, just speaking to my personal experience and also the human experience is the thing that I focus on. Like, what is interesting to me, what is exciting to put on the page, what do I want to put out into the world now that I have the opportunity and have this platform? And then with the wine aspect — which is a kind of underrepresented angle, too — that just felt exciting to me. You know, there are so many Black people that love wine, but we’re underserved. And so as far as even product placement from a set deck perspective, we make sure to focus on Black-owned wineries, and all that just felt like an exciting opportunity for me. Having the opportunity to have an all-Black cast, I consider that a blessing. I remember the shows that I watched growing up that had Black casts, and I remember how that felt to see myself on screen.

8. How do you balance telling the story of friendship and geeking out on wine?

This story is my real-life experience! When in doubt, we lean on the real experience and then we heighten it from there. Each season, I think we want the friendships to grow and we want the backdrop of wine to be a little bit more significant as the show goes on because that’s how it happened in real life. Their knowledge should grow a little bit in the same way that it did when I found this wine bar and didn’t know the difference between a Cabernet Sauvignon and a Lambrusco. But I think at the end with any hangout show, what you are really tuning in for is the cast. It is the characters. In the writers’ room we talk a lot about how to build their friendships and how to develop them, and then ask where we can focus on wine and lean into the wine aspect. We’re going to lean into the wine, the wine of it all, but at the core, it’s still about something going on between our characters.

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