I have never met a very successful person who has not failed at something ultimately it's an essay film comprised of abandoned documentary projects that I have worked on over the years you can really fall into a black hole of chasing money for these things I said to myself
I'm going to spend years pitching this thing and I'd rather just be making it a lot of life is lived kind of for the story you know what I mean this is not trying to be literal German ISM that the more visual invention can make the movie even more true this was a lot of
Discovery a lot of failure in the making of it a lot of trial and error it's so obvious to me that this is your purpose this is what you were born to do well hello everyone it's Jim o shasy with yet another infinite Loops podcast today I am very very excited to have
Chris wilcha on I discovered Chris because one of the verticals at oan ventures is infinite philps and what we wanted to work on originally were document uh documentaries and uh a fellow who works for me said Jim I have found the ideal documentary I I know you so well I know
you're G to love it and then I got a chance to see it and he was right on both counts the documentary in question is called Flipside it is getting amazing critical CL uh claim uh one of the quotes that I loved was um that that said uh this is about uh making a
documentary much like uh Moby Dick is about a whale Chris welcome thank you so profoundly much for having me and also for supporting the film I I I I feel like I hope I've said this to you and you've really heard it that uh to to support a project of this size and scale and to help us get to the
Finish Line was super meaningful so thank you so much Jim I thank you for allowing me to I I literally Chris when I when I watched it I I was just so taken by it so if you don't mind what I'd like to start for viewers who haven't seen it first off you gotta see
it you're going to be able to see it in theaters we'll talk about that and the process and then and then we're going to talk a little bit about um about where Chris sees uh documentaries in general going so so the setup is pretty simple you uh like me love to uh work on things that you don't always
finish and why don't you take why don't you take it from there because there's so many interesting characters give us give us the uh origin story of you know what God damn it I am going to make this but but I'm going to make it in a way that maybe even you didn't know what's
going to be the way it ended up right yeah no that's completely true I I have to say I still as I sit here before you do not have the most incredibly efficient concise elevator pitch right it always someone asked me the other day what's this movie about and I said
creative failure and then they said well what what what does that mean like you know and and and it's it's it's a challenging film to describe and that also made it hard to make a trailer for it because there's so many disperate parts but ultimately it's an essay film
comprised of uh abandoned documentary projects that I have worked on over the years um and they're you know it's an essay film that's sort of all weaving all of these sort of uh failed projects together that by the end they cohere into something kind of strange and unex expected and again that even feels a
little too abstract but to to to start from the origin story so I'm a documentary filmmaker I also make a living mostly by commercial directing and as a documentary filmmaker there's a constant need to generate new projects generate new ideas and I so I'm always running at
things I'm always starting things and what ends up happening is that these things often fall apart it can be because you you know your access to Talent all of a sudden you lose or you lose your creative will and you decide it's not a good idea after you've already put some time and energy into it
or uh the funding falls through right you were promised some kind of investment and then that goes away and so what ended up happening over the years is that I started accumulating these hard drives filled with footage of these abandoned projects um and there
was one that I was making periodically over the years where I had returned to a record store that I worked at in high school with the kind of ridiculous semi- absurd notion of maybe helping try to save it before it disappeared I sort of saw the looming obsolescence of this store and I
thought wow you know it's this wonderful time capsule of it's called flips side uh records as you pointed out that's actually the name of the story the name of the film is just flips side but Flipside records in Pompton Lakes New Jersey was there as this absolute
Treasure Trove vinyl fill Time Capsule but the owner Dan was not interested in modernizing it in any way so there's no proper website there's no real social media presence and so I started returning there on my travels as I would visit New York when I was doing a commercial or visiting family and I
would I would spend some time for a few days each year shooting accumulating footage and I think the first thought was that maybe I'll make a little YouTube video a little homage to the place But as time unfolded and things started to happen and change I ended up
accumulating a lot of footage over the course of a number of years um and you know this too was dangerously imminently possibly turning into another abandoned project so this is a a very long and involved setup to say that sometime around midco I returned to all of these
hard drives I started sifting I started assembling with the help of an editor and a co-writer and we started trying to make sense of all this stuff and and what results is a weird little essay film with cameos from a lot of unlikely disperate people a jazz photographer
named Herman Leonard uh Ira Glass the sort of iconic radio show host of This American Life uh and podcast Creator David milch the Hollywood writer who wrote Deadwood and many other notable amazing shows NYPD Blue and luck and all kinds of things um so Jim I feel like that was a terrible very way too long
pitch but I think you'll say that if you if you if you sit and and and and watch the film and give yourself over to it I think it's it's it's a pretty interesting ride I think it's more than that Chris actually I I I think the why it worked for me was not only were each
of the subjects of the uh documentary that you had begun on them really fascinating the way that you weaved it together you know you know in in this case the the whole is massively greater than the sum of the parts well each of the parts is in itself interesting right
so uh Herman Leonard I knew his work I didn't know that it was him but the minute I started seeing his images I'm like my wife's a photographer and I'm like you know this image right and she goes oh yeah that's like an iconic image and I said you got to watch this and she
was like this is amazing and then but also the way you weave it in like I'm a huge Deadwood fan and to see David milch reduced uh by illness right now but still like worth listening to everything he says and and then finally I also kind of believe that some of the greatest
stuff I mean we were we were rewatching the movie three Billboards in Missouri or whatever last night and like how do you pitch that movie it's true it's true it's so true yeah I mean you must be experiencing this now though when when people are pitching things to you though
right which is sometimes on paper the thing just doesn't sing you just can't get a sense of it and I definitely had that experience with this film where I I initially put together a treatment with the help of a friend and the idea was is can we go out and try to get some
funding for this thing to go shoot it and what we kept finding was people were just like I don't get it like I I think I see it but maybe not but wow this treatment's interesting but I don't know that we're ready to take a risk on this and my original idea was that it would
be maybe a a collection it would be a limited series so you do a half hour on David Milt you do a half hour on Herman Leonard and it was really ambitious but at a certain point I said to myself I'm G to spend years pitching this thing and I'd rather just be making it and so
there came a moment when a small group of collaborators that work with all just decided to sort of throw in and just try to help make the thing to try to help prop up a cut and it was in the making that it just got more and more interesting that's when the meaning started to accumulate when all these
disperate threads started to sort of come together and characters started to Echo with each other over the course of the entire film um so it was definitely in the making uh that it got done but it's it's it's it's like you said it would it was a really tricky pitch like
there was no concise way to say it and I feel like now the beauty of it is is you know you can send it to somebody and they can they understand it right they understand the voice of it the way the voiceover works the way the the sort of trigonometry of the editing like you're
saying it's very structurally sort of complicated because we're trying to we introduce people and then they disappear and then they recur you know I mean so that was a big part of you know figuring out the film was was was how to structure all these disperate parts and
the other thing you know you started out you came out like you got shot out of a Canon with uh with the target shoots first and and then and then life intervened you got married you had kids you had to earn a living um and but it's so obvious to me that this is what you
were this is your purpose this is what you were born to do I think and very kind the other thing that I love about it is a lot of times it can be really tricky when you put yourself in the movie um and like I think that's what makes it quite frankly because that you
are the one constant through all of these very disperate stories did you have any trepidations about that yes absolutely um I was very concerned about the very the bad version of this of the middle-aged Naval gazing guy that no really cares about you know their their
story but and and so I will say that the initial Cuts were much more conservative I very much receded into the background and then I started sharing it with friends and the notes we were getting back was you need more of you you need more of you we need to know more of your
story and I as I got more objective during the process because I was really buried in it for a while where I couldn't sort of see I was just everything just felt too you know raw and personal cuz it was about me so I was like no no no I don't want to say that I don't want to include myself in
that way but then I started to see that like it really was a missing part of the story to not include myself and to not be a little bit vulnerable and to try to sort of make some observations about my own disappointments or heartbreak uh and and and it became really important to
include that and the balance of that was so tricky to find and I think that some of the reviews I'm relieved to report I'm waiting for a real take down but so far the reviews have said there's a version of this that could have been really bad but he he just kind of finds
the right balance you know what I mean like like and and that was such a relief to get that feedback because yes I had total trepidation I was very freaked out um about including much of myself but I think you know there's a nice balance of other voices a lot of the other people
who were featured in the documentary carry some of the Big Ideas and some of the big thoughtful um you know kind of epiphanies and observations and I felt like that's maybe what makes it work is that balance yeah I agree and and I think though that um back to the three
Billboards movie there are so many ways that movie can turn out really bad right when when you're mixing tragedy with really funny dialogue and like my wife and I had seen it before and we just decided to rewatch it last night we were just like whoa boy did he tread the needle with this movie
yeah because tricky and and I think you did exactly the same thing with this because you're the glue that holds the story together and what's also interesting to me is you threw what I took away too in part because each of the subjects in themselves are incredibly interesting
but the way that you weave them together is like one of the best versions of the creative process that I've seen and and by its very nature doesn't comport with an elevator pitch right like when you're doing something really unique a you're take you're taking huge risks which I
love and because because when they work they really work on a level that the for example when we came up to Toronto for the premiere at the Toronto International Film Festival the audience man I mean it was just like it was just so cool because I'd seen it multiple
times this was the first time I was seeing the the Final Cut but on like I just listen talking to people afterwards listening to people's comments like this couple that was walking out in front of me the wife was saying to the husband wow like that is not not what I expected but and he goes but so
good and then when when all the reviews started coming in like I you know I expected them to to be that laudatory and and that's that's what I love about this because there's so many people who are making you know the cookie cutter movie right the cookie cutter documentary and I think frankly you know
one of the reasons why one of our itical this infinite films is I'm so [ __ ] tired of those and like documentaries like yours and others that we're doing right now um that's that's what we're trying I mean we we're taking big chances I mean I have to tell you that's
incredibly meaningful to support that kind of work because I think right now the streamers are rewarding what the algorithm wants and the algorithm spikes with celebrity and True Crime and this sort of spectacle driven stuff and I think things that are maybe a little bit
more formally inventive or more difficult more challenging even in the subject matter are in a moment right now where that stuff is seeing less support so the fact that you're actually following your gut Your Instinct your passion your interest uh is is is such a
is amazing for these filmmakers you know what I mean myself included um and you just said so many things I mean first of all that was such a significant moment for me because I had had my head down and was making this thing in a bubble and in Toronto was the first time I sat
in a room a real you know real room with people that were not just friends um and it was a wild experience and what I think surprised me was the people who came up after who didn't want to just talk about the film they wanted to talk about their own failed projects like a
guy came up and said I've been trying to write a book for years and I stop and I start and how did you do and it there was this unexpected self-help kind of through line that I didn't totally foresee that it really seems to awaken in people you know that feeling of like
there's a thing I always wanted to do or make or a business I wanted to start and I feel like that's been a really unexpected bonus of the conversations that have come around that kind of stuff you know what I mean the the the creative failure but the fact that there's still time to try to do things
and finish things follow through yeah and and that is one of the charms of the film in my opinion in that it's sort of saying to the audience you're speaking directly to those people you're speaking directly to people who have a creative project and for whatever
number of reasons it hasn't been done what you're doing is showing them you know what you can finish too you can get this done too and and I and I think in in in like one of our our goals with uh the movies and films we're making is we we want to inspire people so much and
you mentioned the algorithm I mean my god of course it's going to revert to the mean and like the mean ain't so great to be really really honest and and so the ability to make a nuanced incredible uh documentary like yours I just want to see so much more of it in the world let me ask you like like um
how many times did you switch the order of the who appeared first who appeared last oh man infinite number of times speaking of the word infinite I mean the beauty of these it's almost there's documentaries within the documentary I I came to call them case studies these
individual character studies and what was nice about them is they were kind of modular so you could kind of cut one and then move it around and try it next to this one and and try the ending and there was a section where I make some observations about a a sort of lesser
known David Bowie song and at one point that was my ending and then it was not it was not totally working because it was not the ending of my story it was the ending of a of of someone else's story and so we were constantly shuffling the puzzle pieces around and and then what started to happen is you
know cool little ju to positions where the the the the the two sequences would all of a sudden the meaning of them would magnify just by putting them up against each other or a theme would start to build that you didn't even necessarily foresee about mortality or
about family or about uh again this these these these obsessions are focus on Creative failure like just by putting two characters next to each other um you know the meaning would sort of shift and change so that was the game of this and that's another thing about documentary
is it's very tricky to say hey we can edit this thing in six weeks and can you budget you know that much money for this it's like this was a lot of Discovery a lot of failure in the making of it a lot of trial and error a lot of running back out and doing some more shooting in New
Jersey to figure out what was missing or fill a hole so um you know documentary definitely you know there's a different kind of process to how they get made and constructed than say a feature film um where you sometimes can go actually you know do your 24 shoot days or 30 or 70
come home do the editing it's not to say that you're not making get up as you go but there there's a a kind of narrow band of material you've gathered whereas this has had you know and I kept I was obsessive I kept adding things to the point where the my my collaborators were
like you have to stop like I kept wanting to like I was like can we get you know Bruce Springsteen to come and sing the a song at the end for the end credits and let you know I kept coming up with new ideas um and at a certain point they were like pencil's down we
have to stop um but but I have a question for you which is you know I know The Narrative of your career as it's presented kind of publicly and there's you know this ascent and this success but did you ever find yourself you know miserable and and unhappy in a in a set
of work circumstances where you were like I have to shift I have to change like I'm curious about because you know your story has such a a a you know a beautiful Ascent yeah actually I did uh when I was 25 uh I was asked to well first off I I came from a family where my grandfather
was very very successful in the oil business and my uncle who was running the oil business at the time was not subtle about trying to get me to go to work for the family company very proud of my grandfather he gave away 95% of his own wealth during his own lifetime uh and just uh I was lucky to
have been a the the youngest grandchild after my grandma died he came to our house twice a week for dinner and so I got to spend a lot of time with him uh but so I did not want to work in the oil business Chris I literally had zero interest and so trying to trying to uh
combat my uncle who was very persistent um was difficult and then and then my dad asked me to get involved in in the business that he had and again I did so and I was miserable and I was I was like I can't I can't actually do this and you know so I I my grandfather had this
thing he called premeditating which I started when I was about 18 doing and it's very simple what you do is you write down what do I think I want right and then you write what will happen if I get this what will happen if I don't get this but you add what will happen if I
get this and it leads to bad things which is something people don't normally do what because we always want to be positive right and all these good things will follow and then what same process over here what will happen if I don't get this bad things but also what good
things and and so I did that and it was very very clear to me that well I loved the film and movie industry and the music Industries when I was a kid that's what I thought I was going to end up in um but it it became very clear that I was absolutely obsessed by the stock
market and why things did what they did and so once I got that Clarity it was like now I feel like I know why I'm here now I feel like now this I will and and as you no doubt also know everything that I did I worked to three times is hard but it never felt like work because
I was figuring stuff out and but yeah I think I think that anyone who thinks that you know they look at somebody who's successful and think oh well luck or whatever luck is involved for sure but listen they have had those Dark Nights of the soul the other thing I want to
say is they have failed I have never met a very successful person who has not failed at something and and how we deal with it which is coming back to again the uh flip side how do you dealt with it I just resonated with me so deeply because it's like I failed I failed I
failed God damn it I'm gonna [Laughter] succeed or at least try to make something of the failures right that that was the dream is like that maybe these are not actual failures maybe there is still meaning and energy and Life to this footage that while it's been languishing for a while maybe even
the passage of time has given it more poignance or significance or meaning like for instance you know I feel very lucky that I got to document Herman before he died he's no longer with us you know yeah and then even to get to spend any time with David milch who I
think you referred to earlier who has Alzheimer's and this is publicly known you know we caught him on some really good days and I felt like he was very Vivid and very present I feel really lucky that we got that and I still have that documentary instinct to to document
things because they're going to disappear they're going to change they're going to transform even just from one day to the next you know I mean I still believe in the the the meaning of of of that kind of preservation of experience of relationships of conversations that's why this podcast I
mean you're building this archive this unintentional archive it's just that you know you're effortlessly sort of doing this every week and you're going to look back in a certain point and be like oh my God we have this library that we've created of of these voices and these
conversations um it's it's it's remarkable yeah and it's what's the quote life can only be understood backwards but we must live it forwards right and you know okay I've watched the movie several times to be honest about it thank you thank you thank you and I
watch it because I'm trying to learn something about your art and the thing that really came through to me was the way that the narratives really support one another right like um I I love Uncle Floyd for example so what what what I love about it though is you've got Uncle Floyd who is a
character of basic New York New Jersey uh cable um yeah do you want me to give a little B him just your listeners have no context for having not seen this and before you do very appealing guy so go yeah yeah yeah yeah um you know when I was a kid in the 80s um you know you'd go down the dial
to what was it past the UHF it was it was cable but its earliest most primitive iteration and uh there was a guy in the tri-state area so New York New Jersy Connecticut that was sort of the the the you know his entire reach and his name was Uncle Floyd and he had
this children's show uh or it was it was it it was disguised as a children's show but it was really for adults and it was this over-the-top insane absurd kind of largely improvised comedy um but they would have on local guests local bands uh very incredibly Regional and specific
and I discovered this and it was just this deranged weird Incredible Universe of characters and he Floyd this was kind of a loss leader for him um he would have this show that I think he went out himself and sold a lot of the advertising for he would go to the local
uh Italian restaurant and the Butcher and the the dry cleaner himself and he would get the ad and then they would mention these at the end it was sort of the earliest form you know I'm this kind of advertising um and I stumbled on to this and later when I went to work work
in this record store in New Jersey he would come in and buy records because he was a sort of record collecting afficionado and a musician um and he was like a celebrity to me um so anyway we we end up interviewing him 30 plus years later and his story is also one that's pretty interesting he had sort of a
brush with mainstream Fame and then he kind of receded back into what he used to do which is just he calls it the hot stove circuit so he's playing piano for everything from Funeral Parlor dinners to you know uh uh uh you know weddings and banquets and uh you know uh street fairs
and and you know it's it's a form of show business that is like almost obsolete you know what I mean and and he ends up having some really thoughtful and interesting things to say about creativity and committing your life to being a musician in this particular way
so I I hope that isn't too much backstory but he he's a compelling character within the film and he he says a lot of really thoughtful insightful things well and that's the other thing uh so many thoughtful I I took notes the second time I W the first time I watched
it it was just I wanted to watch it you know just with with a blank page and just take it in the second time I watched it I I literally I think I probably took 10 pages of notes many of them were were quotes from your uh subjects and uh you know the the thing that I was also struck with because it's
happened in my life and I would suggest that it probably happens in a lot of lives was the the Jud appau uh enticing you to uh California and you know that certainly happened to me and and I'm fascinated by the choices we make and you know if you're into quantum physics some of the
quantum physics theorists say well both happen right the cats both alive and dead and we live in a Multiverse and there's uh infinite news and each little choice you made uh uh leads down a different timeline for you but talk a little bit about that I mean that was a
big move to and first off he asked you to come make a behind the scenes uh of his movie funny people is that right yes so I uh you know again was kind of just trying to keep my documentary career going and I had just done this TV version of the radio show This American
Life and we've done a couple seasons of it and it you know did really well and we were really excited but the radio team decided they wanted to return to what they do best which was radio they were not so interested in continuing to do a television show and so I was momentarily unemployed and I get this
call from J appau and he says will you come and make a sort of you know a behind the scenes documentary of the making of my new movie which was called funny people and this was one of those opportunities you know I had two young kids um I just bought a place in Brooklyn thought that that's where I was
going to put Roots down I you know I had family my my parents are out in New Jersey like just you know was kind of all within a very small radius and this opportunity kind of fell in my lap and I looked at my wife and we both sort of said we have to do this like even if
it's a one-year Adventure let's just go do it so we sublet you know the apartment and we um got on a plane and took the new family moved into a place that was already furnished you know like we didn't bring anything because it all happened very quickly and it was a really
um it it help the possibility of being life transforming but what ended up happening was is I made this thing it was on TV one time and ended up kind of relegated to a DVD extra and it was not the Breakthrough moment right it was not the like oh my God your career has
changed you've just gotten on a rocket ship ride and you're just going going going to the you know you know the the the metaphorical Moon it was like that was a gig and the gig's now over and it was a little bit um you know I was thrown a little off balance where I was
like wait a minute now the long-term benefit of this was I ended up cultivating relationship with Jud and here we are you know 15 years later or so and he's still a supporter of the work he invested in this film he was one of the executive producers so that was a completely worthwhile thing but it was a
longer uh it took longer to play out that relationship so I found myself in that Barton think way where I had gone west to Hollywood you know for for payment fortune and I found myself unemployed and trying to figure out what the hell I was going to do next and
another thing I learned about Los Angeles which is this a a fact of of Life out here is there's this kind of water bottle circuit we you know I've called it or I've referred to it with friends which is you go to these meetings and they hand you some water and you sit down you know with your
water bottle and you chat about oh you're so great and I'm so great and this is so great and then you shake hands and you leave and there's like nothing came of it there's not like a job or an assignment or a project and sometimes it there's a conversation and and some abstract idea
gets discussed and some emails are exchanged but often there's just this meeting circuit that you're kind of on and I found that the development process can be open-ended and endless and not necessarily generating any income so you're just having these meetings and
conversations and writing treatments and pictures and there's you're not making money doing it and so there came a kind of come to Jesus moment where I was like I need to you know generate some income here and that is when I started to more seriously shift my attention to
commercial directing where I was like you know is there a way that I could maybe balance the two things can I plug into this kind of advertising world where sometimes the gigs are pretty short and you can kind of come in and come out now what I discovered over the course of
a decade of doing that kind of work is that that is a world unto itself it requires its own form of dues paying you have to get known in that world uh they don't just hand you you know amazing well-funded jobs out of the gate like you have to kind of you know do the kind
of crappy stuff for your real and do stuff for free and you have to build and build and build and so while I was doing that my hopes and aspirations to kind of be doing documentaries started to sort of let's say diminish or or or wither slightly it was I was finding it very
hard to balance the two things to keep feature length you know long- form documentary work going while I was also kind of hustling for freelance commercial directing work and that's a little bit a part of the plot of the movie to which is that art and commerce balance that I think we're all trying to
seek right the things you want to do that you feel like have meaning but maybe aren't necessarily that well funded or subsidized versus the thing that helps you make a living um you know the tension between those things became also part of the theme of the film as
well and I wanted to know like was there a moment um when you felt resigned Andor like I guess that I can enjoy doing this like did because I did see several of your commercials and there's an art form there there's art form to it right I mean honestly no no yeah and by
the way I don't th these in this is not this is like I take the work very seriously and I feel very lucky to get the work and I I don't want to in any way imply that like I casually do it and it's kind of this tossed off half-ass phoned thing like it has been hard to
land these jobs it's incredibly competitive um you know you'd be shocked by how many Hollywood directors and notable crew members and and and everyone who's also competing for the same work but you don't know it you know a lot of those people kind of want to you know slum there between features and
stuff and you know I think they can just quickly scare up a commercial or two and It's Tricky It's Tricky competing against because it's very seductive to the agencies to be like oh we want to stand around in video village with this actor this famous director um but the
the commercial work yes the the that work got better and the assignments got better and more exciting and the crew members I was getting to work with were incredible I mean just a funny story like uh I've done a bunch of jobs with um this cinematographer named Emanuel
lubeski he goes by the name Cho and while we were shooting something for apple he was in the process of winning three straight uh Academy Awards for cinematography for I believe it was gravity uh Revenant Birdman I I I I I'm probably getting one of them wrong but he was his career was absolutely on fire
you know in terms of his fiction future work and I was getting to drive around in Vans and ask him questions about working with Terrence Malik on tree of life and and and and you know how they sh sh this or you know what what lens he used for that and there was like this
astonishing privilege to be able to to to to get to collaborate with people who were operating at that level um and that was sort of a gift of the commercial work as well um I think your question is an interesting one because I think what I've realized lately and you you you
referred to this earlier which is you know the documentary marketplace right now is really tricky and the the sort of golden age of document of just you know a few years ago you know there's been a number of articles in Variety in indiewire that have sort of said you
know those days are over like and and along with the contractions in the business that the writers are experiencing so too with non-fiction film that whole ecos system is is kind of challenged right now and so I have no delusions that I made this you know kind
of eccentric essay film about midlife and creative failure that anyone is going to knock my door down and all of a sudden be you know lavishing me with with with huge budgets to make documentaries open-endedly and I get to hang up my commercial directing hat in
fact I feel right now in this weird uncertain moment in the documentary Marketplace that I'm lucky to still be getting commercial directing work because that's still what's kind of paying the bills at this point so I still feel I feel like it's going to be a a a balance just going forward I feel
like that's my true fate is trying to balance both and you know I'd rather do you know I did a documentary with the Cohen Brothers for uh they did a music documentary uh they wanted to do a music documentary to support their film inside Len Davis and so we did this concert
film and it was incredible it was a just one of the most memorable nights and I got to hire all these incredible documentary DPS and we made this film but the budget was minuscule and it was I only got to do that because then a week later I ran off and was shooting
something for Facebook now meta you know what I mean like that's what was subsidizing that opportunity and so I feel like that's kind of the system that's working for me now um and you know my but my true hope and and one of the breakthroughs of doing flip side and
completing it and finishing it is the idea that I got to flex that muscle again of working on something that I care about that I loved and is Meaningful and so I want to do more long form non-fiction stuff even if no one's paying for it like I still want to I want to run toward the things that are
interesting the topics the subjects the the the the the the events that are happening that are worth documenting and not really necessarily worry about if anyone's going to pay for it right away you know what I mean because you can you can really fall into a black hole of chasing
money for these things years can go by where you're pitching and hustling and Sizzle reels and you're not making the thing you know what I mean you're just kind of making things to sell the idea of the thing and that is a really you know that's a really that feeling can be
really bad after a while you know you can burn out on that process so I hope I answered your question I feel like I I meandered a little there but no no you did indeed uh you also in the documentary you you follow a woman with severe writer block and um and and I
think the the the response to I have many many creative friends who work in the creative world and like the residents that they all had not just just with you and cheering you on like he's actually finishing it this is so cool and I had an author friend who writes fiction say to me he look I
showed it to him and and he was like you just showed me this because you want me to finish that book didn't you but the other thing that I noticed that I just want to uh confirm and see if I'm wrong um it it the The Narrative of of the film itself also seems to be very reflective
of the way you look at the world and and well we and well other people are so you know speaking the lines in their own voice right yeah it I I got a sense the first time I watched it like I was really understanding you as a person so did you get that Fe do you get
that feedback or well I mean that that's very lovely this year and I think that probably what that comes out of is you're I mean ultimately often you're having these conversations and you're asking these questions because they're answers you desperately are trying to
figure out yourself so you're you know you how what you're talking about how you're talking about it you know even if others are articulating the answer it is your obsessions and and and and the sort of narrow Focus that you know you're sort of steering them towards so I think that there is um
yes like a worldview there a sensibility a way of seeing things um but I also think a lot of those people I was drawn to right like Ira Glass you know he's been kind of like a big Mentor kind of inspiration for me because I did um I got to direct a TV version of His Radio
Show for a couple years we did two seasons and just to be able to sit in the room and see how he works and how his staff works and the and the dedication and the the the workaholic Obsession uh with how they they they are Relentless at pursuing ideas or
something's not good enough I mean a remarkable thing that I I had never considered when I got inside and saw how they work is that one of the gifts of radio is they could go out and do an entire episode score it assemble it do all the interviews and then they'd say
you know what this isn't good enough and they would kill kill it and it's because the economics of of radio it was just not that much to lose a bunch of episodes over the course of a year whereas with film we walk out the door and you're spending 30 40 $50,000 in your crew and your gear and your
transportation and and the ability to kill things was so remarkable to see which is some stuff just doesn't work you know I mean some things just it's just not good enough or it's maybe not that interesting and oftentimes with documentary you know you you commit to something and
you find yourself in a little bit of a corner where you're like ah maybe this actually isn't good maybe this isn't a feature film and just you know full transparency I was shooting at the record store but at a certain point I realized I didn't think that record
store could carry an entire full length documentary it was only after it was woven together with all of these other characters and stories that the the the the return to the record store and coming and going and and you know leaving it and then coming back um I felt like we we got the best parts of it
but I was not interested in making one of those talking head documentaries where everyone sits around and says oh this place was so great and I worked here in 1972 and remember that time like it it serves a different purpose like you know you sort of you see the way the
business has changed over the years and then you leave and you go on to another story and then you return and you find a character that you know I have some connection to and then we leave again and so it's this it's this kind of uh time travel you know kind of in and out
of the store but the store doesn't have to carry the entire Narrative of the film yeah I think that's part of the magic of film I I think that you're absolutely right uh Talking Heads would have that wouldn't have worked I don't think yeah where where whereas the way it is
presented to the viewer it's just the thing that I loved about it was just it's so engaging on multiple levels right yeah I think it would not have worked if flips side wasn't included right like if it was just uh you know David and and Jud and Ira and and Herman
it would been interesting but that glue of the story you know your your your teenage memories there when you interviewed your friend and and she's kind of giving and she's genuinely concerned you could just it just comes across and and she's like Chris yeah maybe it's time to just put it behind
you let it go yeah that is uh Tracy who this this is a woman who um I met in high school and I was working at this record store and I ended up handing off the job to her when I took off for college and we both returned there you know 30 plus years later and I hadn't talked to her we we we you know texted
there was some social media interaction but to sit in there and really remember you know some of the pleasures of working at the place um but then also to sort of be like you know we're concerned about its future you know is this can this an experience of coming to a store
like this survive um so yeah that was super meaningful and I loved I mean I loved what she said and she sort of called me out and was like you got to let it go like you know you know your little Obsession here it's time to uh you know it's time to move on um and we
you know we we've talked since then and we have these moments where we were like should we buy the record store from Dan and try to keep it alive we're like no no that's a terrible idea like neither of us have space in our lives to do that but I think there's still such a pull to
keep the experience of a place like that alive you know what I mean the idea that you could go to a place like that that is such a you know it's this Treasure Trove it's it's this all the stuff in there has accumulated over 30 40 years and and it's very you don't get that
when you go into a brand new retail store that's sort of Instagram ready you know there's something incredible about all the the the way the things have landed there the detrus that has accumulated and then the sort of eccentric curation of the owner Dan who
you know it's kind of his domain and in some ways you know he hasn't maybe been maintaining it you know you know he hasn't vacuumed in a while but at the same time there really are there is something special about going there and and that's something I truly do hope
happens is that you know a person might see the film and and and and make the poker you know even if you know you live outside of New York or or you're you know passing through town that I truly do think it's it's it's one of those like it's like an a museum of A Sort that is just so specific and the
experience of going there is so unique that it's still worth preserving for a little while longer totally and the other part of the film that's really interesting that I'm going to use as a lead in to question you about where you see the future of documentaries going is
you have two you have two Dan right uh so you so you have your Dan who whose record store was very I walked into many record stores like Dan's record store when I was growing up in St Paul Minnesota I'm older than you and so I'm I'm uh turning 64 uh at the end of the
week and and so that was like thank you that that that was but that was my teenage years boy those were the kind of places I went to and who are your man I don't even know what your taste is in music what would you have been listening to back then well I will tell you and
maybe this will give you a hint the first book uh record the first vinyl that I bought I bought at age 10 and it was Black Sabbath Paranoid amazing amazing and by the way still holds up totally totally and and I am music nut I love all forms of Music um I I as I mentioned earlier in our chat I was the
youngest I was the martini baby frankly yeah right thanks Mom and Dad thank you thank you for having those martinis because I wouldn't be and so there's like nine years of uh a gap between me and my sister and I had uh I had four I now I have three my oldest sister died
but so I was surrounded by music all of my youth right so but very different kind of music because my dad was a music nut too but you're looking at maybe one of the only 63y old white guys who knows the lyrics to every Supreme song because that's what my sisters were
into that's what was always playing in the family room and literally I I I can sing them all and yet my father loved classical music and we I grew up in a kind of a Frank Lloyd Wright style house in St Paul Minnesota and it had very long hallways and my dad was an early adopter of the 10,000 steps
uh program he didn't call it that uh but he would take four walks a day each in duration of 30 minutes but if you've been if you've been to the Twin Cities you know that winters like if if the United States were the old USSR minnes is where they would send the political
prisoners right cu the winters are brutal brutal so during the winter he would walk inside up and down the hall and he would have music on and I I treat this like it's my own memory I know it's not I know it's the memory of my dad telling me this so many times yeah and so on one
end of the house was the living room the formal living room and then on the other end of the house was the uh family room and this long Hall connected the entire house and all the other rooms and and one day he he would was walking and he found me with my eyes closed H5 with my
eyes closed and he said with this smile on your face and he was playing buck and wow he he he looked at me and he said they called me Jimmy when I was a kid he said Jimmy what are you doing and he said that my response was to open my eyes and say to him daddy what is
this wonderful music and so so he he encouraged so he played Glenn Miller for me he played Benny Goodman he played like all of this all of these Classics so I really do have Catholic with a small C uh uh which kind of means Universal musical tast yeah yeah yeah
and so yeah I was listening to of course uh you know the standards I owned every Beatles album I owned every album by The Rolling Stones Le Zeppelin The Who and then as as they came on the scene I was a big fan of the Clash I was one of the first guys to buy NWA and that was a real interesting
thing because I'm I'm not shy and we had a dinner party with some people who might be thought of as maybe a bit tense in uh life and my wife is looking at me and she's going like she's on the other side of the room and she's going because she knows what I'm gonna do and she's
going like this and for those who are listening and not watching I'm I'm shaking my head very rapidly this was my wife because she knew that I was gonna go over and put on NWA Straight Out of Compton and and tell my most mostly white uh audience uh hey you guys ever heard this
yet and so I dropped [ __ ] the police and like the was this 1989 I mean this was this was9 yeah yeah yeah and and another thing another thing I used to do which people found eccentric was I would walk into a record store and intentionally buy like 25 albums at random literally
randomly wow and that for example is how I discovered some of the punk rock bands that ended up being really really big that's how I discovered Tech techno but back then it was called European newat and I loved it that is amazing you must love streaming though now right
because you have the entire Archive of recorded history in your in your phone right you must love just sifting and and searching and playlists and right I do I I was with some friends though and and the conversation turned to how much joy we all took in making classic mixed
tapes you remember making him and and having to get the needle down just right and then the fade in and the fade out and it would take forever and ever and there was just something so cool about doing that process but yeah I I I do love streaming but back to the question
I was leading up to so so the two the the two Dan right the your Dan is kind of the classic uh eccentric uh who's you know kind of a packrat and kin and has some some incredibly rare albums and and 45s and things like that and then there's the other Dan who is running as you put it kind of the
Instagram ready store and and so as we were watching that with friend it was like wow that that's one friend was like Soul soulless and I'm I don't think I didn't find that Dam to be totally soulless but that was what my friend said and then it came up well this is how CER has changing right
it's it's moving from people don't like most younger people don't want to Paw through you know poorly organized uh Vital Records Etc whereas the new Dan had it you know much more the way we shop today let's let's look at the uh art of making documentaries through a
similar lens what do you see as where where is the art and and the Commerce of documentaries going you mentioned some things earlier but where where do you see like what could be a big win for documentaries wow well I do think in the last decade Plus the the form of documentary has the
creative possibilities of it have exploded right when I was kind of coming up I used to joke about them being brument you know the idea that you you you it was good for you was eating your vegetables and they were sort of a little bit joyless and sometimes
humorless and sometimes not that wellmade but like you knew you were watching something that was important or significant um or journalistic and you know there came a point in the last you know 20 years where filmmakers sort of saw some of the possibilities for formal
invention for bringing in humor for bring elevating the look of the photography and I feel like it it is vibrating with possibilities you know the the form itself um and I feel like also audiences are so sophisticated that they can watch these things and they they understand that like this is not
trying to be literal journalism that that that the the more visual invention can make the movie even more true you know what I mean that it's not somehow diminishing or taking away from the truth of it so I still think there is so much to do and the the form has so much
possibilities and I I'm blown away and new all the time I have a friend uh his filmmaker Named Sam green and he's kind of found this Niche for himself of doing live documentaries so what he does is he performs on stage he narrates he has the musicians in the room with him
and so he recently made one about the cronis quartet where cronis quartet is sitting there with him it's a documentary about them then they're cutting away of footage and interviews and then you come back and he's live on stage and it is a it is a three-dimensional experience you know
what I mean and and it's just playful and funny and interesting he has another beautiful film called 32 sounds that just kind of made the the circuit and he also invented a new funding system for himself which I just think is brilliant which is he pre-sell them on a museum
circuit so he says to the Museum in Berlin I'll have this ready to show in 2026 you know spring so they give some money and he accumulates enough and then he goes and makes the thing and then he does the sort of performance circuit so I just think that that is like this
incredible brilliant you know both that he's making something aesthetically and artistically ambitious but then also he figured out an economic system to support it so so anyway I think that the form itself is you know there there's still so much fun and invention and creativity that
that is possible I think what's gotten a little unnerving and there's been journalism about this and you know a lot of griping online is that there did come a moment where the streamers had the data and started to give feedback to the filmmakers so they
would say by minute five we need this to happen by minute seven we need to know what's gonna you know what the conflict is and and because they were seeing that people were checking out or you know you know that that that the interest level was diminishing or was kind of um and I
think that what that started to do was that a lot of the documentaries you start to see feel almost like an app made it you know there's the the dramatic Arc feels very familiar there's a lot of like stuff that feels like the interviews aren't that insightful and you know maybe there's some kind of
gruesome spectacle to the story I've watched also the duration of some of these things is unbelievable like it did not need to be four hours uh like I no like I'll even just you know I will watch anything by the way I will watch any documentary from the most you know
you know experimental uh highbrow thing academic to the most pop culture obsessive because I learned something no matter what whatever I watch one of these but so I recently as a you know having gone to high school in New Jersey and grown up a portion of my life there
I watched the Bon joobie documentary on Hulu and you know there was a moment where I was watching it and my wife got frustrated with me because I just kept denouncing the repetition and it's not that it's a bad documentary it's just that there was so many moments where
I've like you've said this at least four to seven times you've made this point about that conflict or that moment or that sort of turn in the band's history and it was just that feeling of like this could have been a killer hour and a half but did it need to be four hours um
so so so anyway um I think what's a little nerve-wracking for us documentarians out there now and I think this is affecting everyone not just people making you know sort small Arty things I think it's even way up to you know big iconic people who I know and completely respect and rever what they
do that the budgets have shrunk right so the sort of um you know the cash faucet that was on for a few years there and the golden age when you know Microsoft would knock on your store and say give me a give me six of those you know and five of those and it was it was you know
they were trying align their archives they were trying to build libraries and they were in this obsessive acquisition mode I think that's ended um and I think it's getting harder to sell things um and so I think what's tricky for me is I'm seeing that ideas that I have that I
start to talk to people about or sort of do pitches on um are not what anyone's buying um and that is hard because you need these things do require you know money to make them there's hard cost to make these things you know what I mean and and and I think that we're in moment where the market is
B like I'm hearing this from friends that they had um you know projects that even were green lit and now they're saying you know what we're actually going to cancel that or we're not we're not going to follow through on that or we'll give you half the budget but we're
calling it a day you'd much rather get the film done you know what I mean um so I'm I'm in a weird limbo right now where I'm trying to figure out which way the wind is blowing you know what I mean it feels like things are very dark in Hollywood and and the streamers and what
they are aren't buying and the sort of what audiences are aren't watching it feels um you know things are I don't know things are a little dark I think we're all trying to figure out what's next and how to continue making a living doing this um so I think it's a it's a
sort of unnerving moment of transition and I I I just don't know how long it's going to take to play out you know what I mean um and I think it would be very hard to get into like for instance one of my neighbors is is is a screenwriter and a TV writer and he came of age you
know he was on Seinfeld for a season or two like he was he he was in the Golden Era when you would be on set and you would have a job and you'd get residuals and even he is sweating right now because you get hired for much shorter periods of time you have no ownership of the work you have there's no more
residuals um so again there's a kind of there's some kind of Correction happening and I think we're all just trying to figure out our place in it and how we can continue to make things um and so I think I'm just trying to figure out you know how to keep following the instinct to follow through making the
work but then also finding ways to make a living and you know kind of support my family so it's a tricky balance um so I don't know did that did that answer your question I feel like that was an accidental no it actually did uh the uh thing we are trying to uh do at infinite
films is we uh are in uh the constrained budget era right but one of the things that we try to do to rectify that is that everybody who works on every creative person who works on the film gets a piece of the film and so if if we are able to sell that film or earn money
from that film they get their share of it we think that that's really important because what we wanted to do was create uh an envir like in business if you can make people who work for you feel like owners rather than employees the difference is amazing and so I just took
that learning from the world of business and and said well it is show business right and so and and and so the idea that everybody uh from the director to the writers to the everyone working on the uh film should own a piece of it and then then they're have to uh rely on our
ability to sell it to a streamer or get it sold to a Distribution Company that will put it in the theaters Etc yeah but let me ask you this you're you're you're having fun right now and it sounds like you're really taking pleasure in supporting this kind of work and and you
know you you have such great taste and stuff but do you find this an absolutely crazy form of business because in your Wall Street life you know there was a way of doing things and there's a a sort of Mastery that you accomplished and there's a there's an you know a wealth
you generated and then you come into this lunatic subjective weird ambiguous crazy world of creativity and development and do you just find it like you're on Mars it must be so frustrating because a lot of it's irrational you can't necessarily algo rhythma it right
I don't know I'm sort of curious you coming into this weird world where things are way more nebulous and it's hard to keep things as kind of like you know the the the kind of uh the bright lines of of what you were doing before so that uh leads us right to a really
funny story so uh the the director Ron Howard is a good friend of ours and we becamea we became friends because he and Cheryl his wife lived here in Greenwich Connecticut where I live and our kids were at the same school and they were uh chess players his daughters and my son
and in those days the parents used to be coralled off where they couldn't coach the kids or anything literally impr prisoned in you know a room where they were f it from the outside and I became really good friends with uh Ron Cheryl and that was like one of Bron's favorite
topics of discussion he would always he was fascinated by Wall Street for exactly the reasons you just brought up he's like you know in Hollywood there's just no he goes you guys on Wall Street you have a defined path you know you get the internship and then you do the grunt
work and then but you're always very clear this is how you rise in this particular industry and then he would say you know he told the story about he goes there was on Happy Days like one of the best known actors in America at that time and nobody would let me make a
movie and and he's and he's like I'm trying to figure out if I can't make a movie as the star of Happy Days like how is anyone else gonna get a leg up and so he he was fascinated with like how could we bring that to that kind of process to Hollywood um and so but my answer to it
is we've collected contemporary art for many many many years I love artists I love writers I love painters I love filmmakers I just find them incredibly interesting to talk with they there and so I have a long history of being in the world now adjacent to it right not not
having to cut the deals uh but but I became fluent in artist I guess would be the way that I would put it and so does it bother me no it exhilarates me because interesting in a classic Wall Street meeting you go in with an objective and you're you you everything is designed to get that objective Done
Right In A Creative meeting you you might have an objective when you go in but the meeting can go so many different ways and I love that I love I because creative people are so good at riic I always think like they would have been great jazz musicians right because like
they'll they'll hear you say something and then they'll go oh but have you ever thought and then introduce a completely different idea and the number of times that I've heard like a completely different idea on the DAT that I was exposing and with oh yeah that's much
better yeah and by the way I want to make clear that that I am not also implying that somehow business is not a creative act and you know building these companies and wealth and all that stuff doesn't have inherent creativity to it but I just mean the world that you're
now kind of navigating and investing and supporting yeah does have a kind of crazy nebulosity to it right like I I think that's so interesting that Ron Howard was also obsessed because you know they can be developing 20 scripts and there's only going to be one viable one at the end of the process and
there's an astonishing amount of Labor and energy that's been expended and just arriving at that one single script to shoot you know exactly I I uh no I love it um I uh I love talking to super smart creative people it's been like we were talking before we started the podcast
you were saying you know did you want to have a podcast and I and I told you the story about I was like hell no I don't want a podcast uh but it's actually been even if a little self-indulgent the most fun thing I've done in a long time because I get to talk to people like you and and I
get to talk to this really interesting group of people who share who have really deep domain knowledge in subjects that I'm just learning about and so I love being able to ask you know somebody of your caliber like how does this happen how do you how do you weave it
how do you get that to how do you get that outcome right because like that's amazing and then I like I I I I love you know a lot of life really and I think one of the reasons I love documentaries we like at least I do a lot of life is lived kind of for the story you know
what I mean absolutely and so it's not always well we've got to make you know X and that's why it disturbs me when I hear the feedback that you're getting at the five minute mark this has to happen like I would just so that and if somebody said that to me I would just
say you know go [ __ ] yourself because you know a computer can make that I'm not signing on what what is your favorite documentary that you haven't made oh my God one that I haven't made personally yeah I thought you were gonna say my favorite document of all time um wow
um well you know I have an unformed thing once again because I just chased an an instinct is that um there is a philosophy professor of mine that I studied with when I was an undergrad who was one of those transformative characters in my life you know who made this impossibly significant impression
on me and cracked my brain open um and it occurred to me recently wait a minute I don't even know what for but I should I need to go talk to him and document it because I'm worried he might not be around much longer and something's going to get lost um so that's not like a
pitch fully coherent Stone but that was a sort of 4 AM thought I had the other day where I was like holy [ __ ] and again something may come of that you know is there a philosophy sort of larger meditation on something but I felt this incredible instinct to go document him
and I think that's where a lot of those ideas start um as far as like an unmade unok film oh I got I mean I I think the ones that are truly exciting is when you know you're in a place in a time that is completely unique and will never happen again and so for instance I
had this incredibly small window of time where I was dating a woman who was a a part of the marketing of the band The White Stripes and I was um got to go along with her to go see a lot of live shows and I started filming and I could feel from show to show the energy building and it was so obvious that they
were in the process of blowing up and I thought this is my don't look back like I am here for this I'm feeling the energy in a larger cultural way and then we broke up and I never had access to together so I I actually have some of the footage like beautiful 16 millimeter
film and a couple of really memorable shows where there's just not that many people in the audience it's not that huge a show and then long behold within three months the everything just shifted and the fuse got lit and they you know they ascended to Greatness and that was
one of those moments where I was like you know you're just the time and the place you're just there and then it you know it disappeared so so disappears yeah I think I think but I'm still alive and attuned to moments like that right I still want to act on those instincts
which is when you feel something happening with a person or an artist or a band maybe to not so much worry about you know the pitching and the funding but just actually start documenting the process because you're going to get some kind of incredible transformation you're
gonna you're gonna capture something meaningful yeah and I think that's kind of where the magic happens right because [Music] um I as I mentioned my wife's a street photographer here in New York and I I see a lot of similarities and and I'm a good friend as you know of Joel meitz
who's considered like the greatest living Street photographer and I see a lot of the way they look at the world in you and by that I mean they have this ability to kind of sus out the moment that needs to get captured and and that is something that you just you can't teach that to another person right
yeah but that's where all the magic happens I think in and it's why flip side was so magical as well well Chris uh I'm getting the hook here from my producers uh this has been amazingly fun at the really appreciate it sorry at the end of all these podcasts we we give you
the opportunity to incept the world so we're we're gonna wave a magic wand and we are going to make you Chris emperor of the world only for one day and there are rules you can't put anyone in a camp and you can't have anyone execut it but what you can do is we're gonna hand you
a magical microphone and you can say two things into it and everybody on the planet is going to wake up whenever their next morning is and they're going to think that the two things that you incepted were their own ideas and they're going to say unlike all the
other times I'm actually going to act on both of these ideas what two things are you going to unet in the world's population oh my god um this is incredibly intimidating um well let's take a flip side theme which is to finish the thing that you've always wanted to do to to to go start to
make the thing to act on the instinct to not suppress it and neglect it and procrastinate but actually to take action um in your in your creative projects and then there's I have a second thing that I have to profoundly incept to the world is that what you
said yep you got one more that's the first one's a very good one and then the second thing you know I've been thinking a lot lately about um have the conversation and what I mean by that is whether it's a relationship or a spouse or a parent there Comes This
Moment where this person disappears and you haven't had the conversation and the knowledge they've collected or the version of you that they know disappears and I have been finding lately that I have really tried to act on having the conversation to call that person and to initiate even if it's
awkward or painful or hard and so I guess my second thought would be to go have those conversations even if they're hard or difficult to learn something about the past or to reconcile or to repair something that went wrong a long time ago um I've been trying to really
act on that impulse and that instinct and I I feel like that would be a good thing to incept people to do too great great advice but Jim I honestly I can't thank you enough and and you facilitated this documentary Making its way into the world um and we're so excited for it to get released
and to people really start connecting with it you know it's just been doing the festival circuit and now we have it's going to get a release and then it will you know be able to be streaming and all that kind of stuff so we're finally on the path for the movie to get
seen and um you're you're a big part of that so thank you so so much well it was absolutely my delight and I absolutely hope it is only the beginning of a wonderful relationship thank you thank you um so let's talk again soon and thanks for having me thanks for coming on Chris