With his new, SXSW-premiering Netflix Original, Win it All, the famously improvisatory writer/director Joe Swanberg has dealt his fans a real surprise: a picture with a much clearer plot, rhythm and character journey than his previous films. Indeed, with this movie about risk-taking, Swanberg has taken on a risk many successful filmmakers have avoided — the risk of artistic evolution. Pairing up again with collaborator Jake Johnson (Swanberg’s Drinking Buddies, TV’s New Girl), Swanberg puts his focus on gambling and the addiction to both winning — and perhaps losing too.

Johnson, who co-wrote the script, plays Eddie Garrett, a down-and-out guy (classic Swanberg), who gambles to both make money and, usually, lose it. When he’s left with the task of babysitting a large, black bag and told not to open it, his attempts to clean up his act are at risk. There’s a wonderful moment when Eddie first opens the bag, because of course, he sees a massive stack of money. His response: “Oh, no.”

The rest of the film unfolds with the same attention to emotional detail as other Swanberg films. His knack for uncovering human moments in everyday conversation is at play and threads the story together in a fun, rapid pace. It’s the “Johnson and Swanberg” take on a poker film — a dose of gangster drama, screwball comedy and indie arrested development.

Filmmaker had a chance to sit down with the duo this year at SXSW to chat about this new direction in their filmmaking. Johnson once played cards to make a living, and although Swanberg hasn’t ventured much into that realm, he admits filmmaking is a gamble in itself. “For me it’s not about being addicted to losing or being afraid of losing, but make sure you learn when you lose, man,” Swanberg explains, also dishing out some Tom Waits wisdom. The two opened up about their choice to write a more structured script, the risks they’ve experienced with filmmaking and the definition of a “win” and “loss“ — to each his own.

Win it All is currently streaming on Netflix.

Filmmaker: I loved the film. There was a review that came out that I read which called it your “most traditional movie” yet. Do you agree with that?

Swanberg and Johnson: Absolutely.

Filmmaker: So what does that word — “traditional” — mean to you? Is it about having more of a structure to the script?

Johnson: It means that we wrote a three-act structured movie, had all the beats figured out, and wanted to go in where we knew what was going to happen and build to each beat. On this one, we sent that script to agents, got notes, and we took the notes. When we were bored of writing, we kept writing. We did the homework on this one which we hadn’t done [before] on projects together. On Digging For Fire, we thought, we have an idea, and we have talented people, and a talented crew — we don’t need to do the homework. So that was that. Now, what happens if we do the homework? The homework for us is traditional storytelling, so that when we get to set we don’t have to find the story beats, just the dialogue beats or funny moments or real moments.

Filmmaker: What were the benefits of choosing to do that? What were the pitfalls?

Swanberg: It’s interesting, what Jake’s talking about, this balance of writing and doing the homework versus getting on set and making the movie. The less preparation you do in the script state, the more you’re writing while you’re shooting, and there was something liberating about having a solid script going into this one. We 100% knew how a scene was supposed to work. It connects piece A to C, but then knowing that, B could be anything it wants to as long as this information gets delivered.

Filmmaker: I was a playwriting major in college — sounds like my world!

Johnson: Me too. I did playwriting at NYU and switched over to screenwriting for the last couple years. And there were no pitfalls. I really love story, so I love all of that.

Swanberg: I was the suspicious one.

Johnson: Joe and I, when we work together, we’re very different guys. But we socially really like each other. When we met on Drinking Buddies and he pitched me his process, I told him, “You sound like a car salesman, and if what you’re selling me doesn’t work, you sold me a lemon, and then you’re garbage, man — a big talker but you don’t deliver.” I didn’t see how we [could] have an eight-hour day with no script and make a movie that works. And then that movie really worked for me — I really liked it. Shooting was a blast, and we did find things that were honest.

And then Joe said, “Great, the next thing I want to pitch you is that we should finance these.” And I was like, “Yeah, but everyone in Hollywood always tell me never write a check, because that’s how goofy actors like me go broke.” And he said, ”Trust me.”

And so we financed a part of Digging For Fire. And then we made our money back and everything was fun. Alright, so on this one, let’s do this story thing. On set… it would be, “We’ve got it, but what else could we find here?” So while shooting it still felt like a Swanberg movie — that feeling of “we have to discover” and “we have to be on.”

Filmmaker: Why did you choose the theme of gambling?

Swanberg: I think Jake brought it. I saw a film called Sticky Fingers, which involves a black duffel bag. It got me laughing about the idea of Jake’s character being in charge of something big. I texted him and asked if there was anything to you ending up babysitting a bag of money. Is there anything going on there? Jake was kind’ve like, “I don’t know.” Four months passed, and then something stuck.

Johnson: In terms of gambling, my mother was a poker player, supporting herself for a lot of years doing it. My cousin is a card player. I’ve always been a card player. Before New Girl, it was always the way I could supplement my income. I worked at a casino when I first moved to Los Angeles.

Filmmaker: That’s a movie right there.

Johnson: Yeah, a different one. But it’s never the Eddie Garrett story. Nobody in my family is that. It’s more a way to do gambling if you can actually grind at it, where you’re not chasing highs and lows, you’re playing percentages and poker and cards. If you can find somebody weaker at the table, you can just go after theirs and avoid the stronger person. I then worked at a casino and I watched real gamblers who had the sickness. Without exaggeration, I would see these couples — two people I remember distinctly. All of a sudden they would come in separately. She started looking trashier. He got thinner and paler, and I was like, “What the fuck?” After a year he looked like a degenerate gambler. He had [begun] looking like a Midwest boy who fell into this casino, didn’t know the rules of California blackjack, and by the end, if I walked in, he was just a rat playing cards. It was a world I was interested in, and then Joe and I talked. He got into it. We went to casinos together, because he’s like, “I gotta be able to direct poker.” He got into the world, and he had a take on it.

Filmmaker: Jake, both your character on New Girl, and Joe, your characters since you started making movies, are all working with cases of arrested development; they are trying to get their shit together. Do part of you guys feel like you are that way as well? What is your personal connection to those types of characters?

Swanberg: I relate to gambling a lot. Not as a card player, but as an independent filmmaker. It’s interesting to me how much Eddie Garrett makes sense to me and how my line of thinking has been just like his. Especially the optimism of coming off of a win, thinking I could do this again.

Filmmaker: What has been a win for you?

Swanberg: I’ve been financing my own movies since I was 22 years old. I’ve won and lost all along the way. When I’ve had a win, that win financed the next movie. When I’ve lost, I’ve had to get a real job, save up some more money to make another movie. That logic, as sick as it is, I get it. I’ve gotten it my whole life. As I’ve gotten older, thankfully… I’m literally saying this on the record… “And five years from now Joe Swanberg lives in the gutter!” [Laughs] As I’ve gotten older and theoretically more responsible, I’m still doing that gambling, but I’m not going all in with everything like I used to when I was younger and wasn’t married, didn’t have kids or all that going on.

Johnson: My connection to that character is that if I didn’t start getting cast as an actor, I’d be way closer to that guy. But you can’t be that character when you’re on network television. You gotta be there at 6:00AM and you’re there till 6:00PM and you’re working 14-hour days — sometimes five days a week, and then on weekends you’re doing press, and then you’re back in. We play characters who are sloppy and unprofessional, but we’re working more than lawyers! To do television! [Eddie Garrett] is a character that’s fun to play. There’s a lot of comedy there, and you can actually have growth. Rather than, “Yeah, I’m married, I have kids, I don’t socialize like I used to cause I have my sleep schedule and feel healthier.” Where do you go from there? Party a lot, then? Alright, then I have to get back to the start [of writing the character] — that’s not growth. It’s a lot easier to say in a story that it’s a guy who has not met his potential. He should be somewhere else but he isn’t. Then life happens and he sees where he should be. And we’re going to spend an hour and a half and he’s going to try and get there.

But at 38 years old with a couple of kids and seven straight years of employment and savings, I don’t relate to the character I like to play [on television] as much. But I’ll always have the most affection for him, since it’s the character that got me paid. I got to stop doing all the day jobs I hated. I was like, “Oh, I could do this.” So I will do this, ideally, until the wheels come off.

Filmmaker: There’s a line in the film where Keegan-Michael Key makes you, Jake, repeat, “I’m addicted to losing.” I’ve been thinking about this this morning, wrapping my brain around it. Losing can mean different things. Joe, in the film business, you have managed to preserve your voice. Has that caused you to lose anything along the way? Have you chosen losing in order to preserve your voice?

Johnson: That is the question of the day!

Swanberg: All I can say is that every artist aspires to a different kind of career. I feel lucky to have had inspirations like Tom Waits and Robert Crumb. Even as a young person, you look at Tom Waits’s career: he starts off as a folk singer, then he turns into a boozy piano lounge singer, and then in the ’80s he turns into a weirdo experimental pop singer. Then, he grows this gravelly voice and turns into this wizened old rocker. All along the way though you’re like, that guy was Tom Waits the whole time. It doesn’t matter if the albums sell better or worse, the thing about Tom Waits was like you come and go out of his career. “That album wasn’t for me, but I’ll still listen to the next one, I’m interested in where he’s heading.” So I’m never freaked out if a movie doesn’t quite land. Especially since I had some early success. Not huge success, but enough to keep me going. It was nice to go that one that landed — people liked that one — and then make one where I’m like, “Oh boy,” and then make another one that’s even worse, and then make one that lands. It’s a long haul. I’m gonna be at this for a long time. I intend to make movies as my career until I’m old.

They’re not all going to work. They never work for anybody. My favorite filmmakers have a bad movie every third or fifth movie. It’s fine. You will suffer through it. Eddie Garrett loses and then lashes out at the outside world: “Who fucked me here?” For me it’s not about being addicted to losing or being afraid of losing, but make sure you learn when you lose, man. Do not just lose and then blame other people because if you lose and then you blame other people, you’re bound to lose again.

Johnson: I think the question is really interesting. There is a thing where sometimes you win when you lose, and you lose when you win. At least in my career, I started seeing a path. And then you get to a point where you go, “I did this. Now, I’m being offered that, and that movie is the big win but there’s no happiness there.” You look at [these situations] and you’re thinking, that person’s a good actor, what are they doing? That’s a really interesting human, but now when you sit down with them, they’re a less interesting person and they’re tired and they know it. Congratulations, you won the game, but I think you know you’re losing the game.

For example, doing a straight-to-Netflix movie. Some people, my dad for example, will go, “Why did you go straight there, don’t you want to go to the theaters?” And we’re like “Fuck no!” We made this movie for Netflix, with that in mind and going to SXSW. He’d go, “Why not get the theaters?” ”I understand that’s a win for you, but how is that a win for us? Why do we care if we’re in a bunch of theaters. We want to make a movie and get it right to people.” That’s a loss in some eyes, but it is a win for us.

I don’t know, it becomes a tricky thing. Whose win are you chasing? If you’re just chasing your own win, you’re going to look like a loser to a lot of people, but deep down it’s I believe! [To Joe] In our corner, we’re gabbing like, “Are you happy with this win?” For this one, when Netflix came, no one else had seen it, and we’re, “We’re happy with this, and if it’s perceived as one thing, let it, cause that’s our win.”