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Leo Sidran: Conversation Artist

Leo Sidran: Conversation Artist

Courtesy Allan Tannenbaum


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There is only one of you and you have to find out what it means to be authentically yourself
—Leo Sidran, musician, podcaster
For music lovers, listening to music is often not only about the music. An album is much more than a vessel of beautiful chords, notes and lyrics. It offers mission statements, "how to" manuals, and blueprints for life strategies. Each song a trap-door it is impossible not to sneak into, in search for insights on how to handle our everyday existence. Each musician's career a collection of case studies in the art of perseverance. Your boss has been bombarding you with emails at 2AM, the kiddo threw up all night, bus drivers are on strike and you are late for the most important business meeting of the year? Think about Keith Jarrett who played his Köln Concert after arriving late at the venue, sleep-deprived and with excruciating back pain just to find out that dinner was delayed and the piano was in terrible shape.

There is a podcast out there that does a great job at leaving plenty of breadcrumbs for the Hansels and Gretels in us to find the way home, Leo Sidran's long- running The Third Story.

The Third Story does not run into the pitfalls of most interview podcasts, which cover the range from verbal waltzes between starstruck hosts and narcissist idols to deranged monologues disguised as dialogues, to transactional conversations between networking hosts and self-promoting guests.

Sidran's caring and amicable spirit may be at the heart of the podcast's success. These are talks between friends even when they involve people who have never spoken to each other before. Friendly, however, does not mean obsequious, and if the questions come from someone with a lifelong commitment to self-reflection like Leo Sidran, chances are that those questions can be as helpful to the interviewee as they are to the interviewer.

Starting from its title, The Third Story acknowledges that each conversation brings "three sides to every story: your side, my side, and the truth." Be as it may, there is also a fourth side: what the listener takes away. If it is true, as Toni Morrison put it, that people forget what you did and said but they will never forget how you made them feel, after feeling the friendliness of these podcast conversations listeners may find it safe to ask themselves the same questions, and to challenge their own preconceived notions.

According to an old adage, "when the sage points at the moon, the fool looks at the sage's finger." If music and music making are a metaphor for life, then Leo Sidran is trying to help us see that, and not get lost in music's superficial aspects.

A word of caution: you may come out of listening to Third Story feeling that either the host or his guests are your longtime friends. If you happen to run into them, apply some restraint, don't go up and start talking to them as if you have known them all your life... or at least introduce yourself, explaining that you met on the Third Story.

We spoke to Leo Sidran to try and figure out what breadcrumbs lead him to where he is.

The many sides of Leo Sidran

All About Jazz: You are a drummer, singer, podcaster, producer, engineer... how do all these roles influence each other?

Leo Sidran: I do see them as a seamless expression of who I am. Over time, I have gotten more comfortable with the idea that I do not define myself by any one of those roles. Every now and then it is a good exercise to ask myself "How would I feel if I never played the drums again?" "Would I feel satisfied if I could not write songs anymore?." The answer is still that those would be big losses for me, in particular with regard to songwriting.

But I have to recognize that in the past decade doing interviews for my podcast has come to define a big part of how I see myself creatively. I cherish the connection that I get to share with the people I talk to on the podcast.

I do not think it is convenient, or even useful, to think about my different roles as distinct. I see them as different facets of a larger story. But I did not always feel that way. For the longest time I was very self-critical, because I did not feel committed to any one of them and did not think of them as being strong enough to have the potential to become really excellent. Let's take the drums, for instance. I saw drummers who were my contemporaries spending all these hours every day in a practice room playing, because they saw themselves as "drummers." I never had that impulse to become virtuosic or exceptional in any part of what I do. I am not obsessive in that "micro way" that I think a lot of people that I see are.

So, in the end, it was better for me to be more diversified in what I do. I guess that is closer to how my brain works.

AAJ: One of your albums is entitled The Art of Conversation. One of the songs on your album What's Trending (Bonsaï Music, 2023), "There Was a Fire," is about the preservation of memory, which is exactly what podcast interviews are all about. Looking at this interplay between the musician and the podcaster in you, do you feel that your songwriting has evolved as a result of your podcasting experience?

LS: Of course. Some of it is coming with age, also because I have been doing the podcast for years now. But there is a clear influence of the podcast on the songwriting. And even on all my other projects in general. I was much more interested in doing commercially viable work before I did the podcast. I was trying to do things that could be a "hit." In other words, I was thinking in a very different way before I started doing the podcast.

In terms of my songwriting, being a storyteller and a story collector became increasingly important. I cannot pinpoint the moment when that happened. It has been a gradual development. Over time it has become important for me to be able to do a similar thing in songwriting, telling stories, capturing little moments of life like I have done for my last album, What's Trending, which—at its core—is a collection of snapshots of domestic life, small moments in life about my daughter, my grandfather, my life at home during COVID. Thinking in those terms about songwriting and what I wanted to say was the indirect result of having had all those conversations for the podcast.

The title track of The Art of Conversation, on the other hand, was the direct result of the podcast. I had just interviewed Kat Edmonson. I had been a fan of hers for a long time and getting to know her music and then speaking to her personally was wonderful. The interview was an hour or two. After that we just chit-chatted for another couple of hours and when she left, I picked up the guitar and I wrote that song immediately. I wrote it for her to sing. I get inspired by the people I meet. Of course, I feel lucky and fortunate that other people find value in it, but if I could, I would probably have the same conversations for myself.

AAJ: It is as if you anticipated my next question, which was going to be exactly about that "If I am having fun, the audience will have fun too" attitude that makes being on stage as a musician and being a podcaster behind a microphone quite similar...

LS: Maybe I should not publicly admit this... but for the first five or six years I never thought about the audience of my podcast. Maybe because I thought that nobody was listening to it. I just thought that it was something that was worth doing. Over time I have learned that there were people listening to it, and—in some extreme cases— studying it and using it in their dissertations! That is very fulfilling! So I have started asking myself "Does my audience want to hear this?," "What does the audience think?," "Is my presentation clear enough for the audience to follow?," "Is it clear why I am talking to this person, why it is important?" Now more than ever I go out of my way to clarify, because I feel a responsibility towards the audience that I did not feel before.

The Third Story

AAJ: Where does the title of the podcast, The Third Story come from?

LS: I love word games. The Third Story was originally just a play on words. For the first years the podcast was recorded on the third floor of a brownstone in Brooklyn. Then I thought about this expression "There are three sides to every story: your side, my side, and the truth. And no one is lying." And that made me think about what podcasts really are: there is your story (the interviewee's) and there is my story (the interviewer's), and then there is the third story (the truth) ...

AAJ: Let's go back to the very first podcast episode featuring Will Lee. Was that just a conversation that was so good that it had to be shared, thus sparking the idea of a podcast, or had you already decided that you wanted to start a podcast?

LS: At that point I did not know what I was doing at all, but I did know that it would be a good idea to do a handful of episodes to learn what to do before launching a podcast. Will's was not my first interview. I had actually called some friends to try things out with them first. Unfortunately, a few of those early interviews did not come out because they were still too rough around the edges. Some did, for instance the one with Tatum Greenblatt, which was actually my first episode ever.

Thinking back at how it all started, I think the seed was sown during the endless hours of studio work. I have been writing music for TV commercials or for film and documentaries, for which I would have musicians come over to the studio. I have always liked working in the studio, but what I loved was hanging out before or after, just talking, swapping stories, and finding out where people have been, especially people I had never met in person before. You know, those first 15 minutes when you talk to establish a connection, talking about life. Initially I thought I would interview musicians that I hired for the commercial work. But it quickly became clear that doing an interview after a day's work was not conducive to a quality conversation. So, I decided to just email people I was friendly with who might be open to recording an interview at a suitable time in a more relaxed context. At the beginning my emails were quite "careful." Not apologetic, yet almost hesitant in my ask. Will was so generous... he left a strong impression. When, for the 100th episode, my wife interviewed me and asked which episode meant the most to me... all I could think about was Will's because I still had with me the strong impression that Will left when he came over to my house and he was so sweet, candid and revealing, and also patient with me... I had all these notes I kept looking at, since at that stage I was just someone trying to make a podcast, but I did not know if I could do it.

AAJ: A question about the similarities in the creative processes that are behind writing music and recording a podcast. There is a lot of talking about "honesty" in music-making, what is honesty in Podcasting?

LS: Personally, I find that honesty in my podcast is related to motivation. I need to be authentically curious about the person I am talking to. I have loved getting to know more about their lives. It would be dishonest if I were to talk to somebody purely for promotion or because there is some transactional aspect involved.

I see what I do as something akin to advocacy, to some degree. Choosing who to interview is akin to telling our audience "you should pay attention to these artists I care about, and I want you to care about them too." So, you cannot help but be honest about that. Some people are making a lot of money from podcasting, but most of us are not in it for the money. We are in it for the love.

LS: So, podcasting is the latest way of "making mixtapes for friends"?

LS: Yes, the conversation is a sort of verbal mixtape for your friends.

AAJ: Mostly friends you have not met yet...

LS: That is the interesting thing.

AAJ: Have you ever found yourself lost "in the zone" during your podcast conversations, the way it may happen when playing music?

LS: Definitely. After a good conversation I feel the same way as I do after a good performance, or a jam session, or when I write songs with other musicians. Maybe a performance is a little different because that takes place in public, whereas a podcast—even though is listened to by an even larger audience—takes place between two, maybe three, people who are not feeling the presence of the audience at that particular moment. On stage, you get the adrenaline from an audience that you do not necessarily get in a conversation. But, when in this intimate interview moment I feel I have locked in with somebody and we have gone somewhere and we found a story together, that is a big part of what I am trying to do.

AAJ: Earlier you spoke about how the conversation with Kat Edmonson inspired you to write "The Art of Conversation." Looking at your podcasting more broadly, are there things that happened, or were said, during these interviews which stayed with you well beyond the end of the conversation, and even influenced further choices in your life or musically?

LS: Definitely. And then they influence the next conversations I have because I am collecting these stories, opinions, philosophies, and experiences, and they pour into the next conversation I have, and so I feel like I am dragging this growing bag full of peoples' lives behind me when I talk to the next person.

If I look back at each episode, I remember at the very least one thing that the person I spoke to said to me. I can then bundle them in groups... Here are the people I talked to that had shared this kind of experience, and then here are the people that have this kind of attitude or philosophy about life.

It may sound like a cliché, but the biggest take away which comes up over and over and over again is that everybody had to figure themselves out, in their own way and in their own time. There is only one of you and you have to find out what it means to be authentically yourself. Each of these people at some point confronted themselves and had to come to terms with themselves. How they developed is what fascinated me.

AAJ: One of the fascinating aspects of the Great American Songbook is that it virtually contains at least one song about every form of experience and emotion known to humankind. Listening to the episodes of your podcast one can notice a comparable range of topics and experiences that are addressed by your guests. Is there something you have not yet been able to discuss and you'd like to explore with a future guest of your Great American Podcast?

LS: As I was saying earlier, my experience with the podcast is ever-evolving, as it is informed by all the conversations that are accumulating. There are many things I did not know anything about and I learned along the way, or that I do not know about today, but I will discover at some point and become interested in because of these conversations I am having. Looking back I have to admit that I talked to a lot of white men, many of them Jewish men. To a certain degree this may have reinforced a worldview that I already had. That made it comfortable to connect with them and realize that, more than any theme, what I wanted to expand was just the profile of the people that I talked to. Looking forward, I want to talk to more people whose life experience does not resemble mine.

AAJ: Speaking of "comfort zone," have there been interviews in which you were not as comfortable as you would have liked to be?

LS: There have certainly been a few. Nothing terrible, of course. Speaking to people of different ages is very interesting. The relation one can establish in the course of an interview with older people seems to be a bit different. I have talked to a handful of people in their 70s or 80s. When I spoke to Creed Taylor he was 87. George Wein was in his late 80s. The sociologist Howard Becker was in his late 80s as well. That generation has tended to be a little more challenging for a number of reasons. First, I met them at a time in their career when they had become very esteemed and established. Secondly, they are a bit less conversational so it is less easy to get to their core humanity and the conversation remains a bit more on the surface. But I have learned to go with the flow, and I have found it very comforting to think that I am not getting the only interview that this person is ever going to do. I am just getting the interview that we did and that is all I could have asked for. And in fact, in all three cases (Creed, George, and Howard) I ended up doing some of their final interviews, which makes those conversations even more important.

AAJ: This going with the flow and staying in the moment, a quintessential jazz skill, becomes quite striking when you integrate the mishaps that occur during a conversation, and you do not edit them out of the final version of the episode. I recall, for instance, when you interviewed Lionel Loueke and the conversation flowed despite the Zoom connection kept stalling and you used that as a metaphor of how he had turned the challenges of getting hold of strings and guitars in his native Benin into a strength. Do you edit anything out of your conversations, or is it totally "raw"?

LS: The fact that you asked that question is probably the best review you could give me because my interviews are so tightly edited that I often wonder how obvious the edits are. I edit all the pauses, as many "uhms," "ahs," stutters, misstatements and false starts as I can. As my dad would say—I want to put the best haircut on everybody. I want them to sound as fluid and comfortable as possible. The "uhms" and "ahs" drive me crazy. I do them often myself. Plus, sometimes I talk for much longer than I want the episode to be, so I have to go through it and find things that I can cut without affecting the episode.

In the last year or two, I have started to focus on the production of the introduction and on adding musical examples to illustrate what is being said, which I think is something special about the podcast, as it becomes a way of telling a secondary story about the history of music, but through one person's unique lens. The guests do not even know that that is going to happen when we talk. I look up whatever music comes up in the conversation and bring it in, so we can hear it, but that also involves a lot of editing.

This development has allowed me to think about each episode as a little art project where I can not only choose to illuminate or keep the mistakes, but I can choose to make something creative out of them, to manipulate them into a little artistic statement of my own. If it seems appropriate, this way I find myself involved in a collaborative conversation, a secondary conversation, with my guest. It is something that is happening between me and the guest. The audience gets to hear it but I am actually sending a love note to the person that I have talked to, who gets to hear that I was paying attention when they were talking about music that they care about, and then I go and find that music and I bring it in. For me it is a way of honoring their story.

AAJ: This attention to detail can lead into a rabbit-hole of endless refinements with diminishing returns. At what point do you say, "OK, this episode is ready for publication"?

LS: There are two ways to answer the question. The first is, how do I know when the conversation is finished? The other is, how do I know when it is time to put the episode out?

As far as the first question is concerned, 90 minutes is a good amount of time to talk to somebody. If I only can talk to them for 60, that is OK, and if we can talk for two hours, that is good too. If at some point one of us has to go to the restroom, that is perhaps a sign that we've been speaking too long... but sometimes may also be good to take a break and come back later. When it comes to the editing aspects, that may vary. The Will Lee episode must have taken me a month of polishing, obsessing over making improvements and, actually starting to damage it by doing too much work. More recently, I have deadlines that impose a different approach. For over a year I have done a new episode every other week and on the alternating weeks I take a rerun and I make a new introduction to it. Having a schedule is punishingly brutal. It leads to releasing things a little more quickly or urgently than you would like, but without that accountability, nothing gets done.

AAJ: For most of the podcasts that involve an interview one is better off fast forwarding and skipping the introduction, because the introduction is just delaying the real thing. In your case, on the contrary, one may frequently regret when the introductions are short, because of the elegance, eloquence and depth with which they touch upon music and life. Have you considered a podcast format in which it is just you talking, without the need of doing interviews?

LS: I do not think I am there yet, but I also sometimes wonder if that is where I am heading to. I am thinking about it. My friend Gegè Telesforo recently asked me "Why do you put so much work into these introductions? By the time the interview starts I do not need the interview, I already learned what I needed to know. Why don't you just play the interview and save yourself the time? I know how much time you must be putting into this... " And I told him "That is where may passion is right now, the introductions!"

I cannot do them until I finish the interview, but I can see that then you almost do not need the interview because I have sort of processed the story through my own filter. It is a framing of a person's life and career through sound, through story, and through the experience of having talked to them and then wanting to share that experience with my listeners. For the time being I am trying to have it both ways where I do these introductions, and then I also give you the interview, so if you have 90 minutes in your day, you can listen to the whole thing, but if you have only 10 minutes, then you could just listen to the introduction.

One thing that is nice about the podcast format is that there are no rules, and you can change it anytime you want, it is very freeform and ever evolving. And this loops back to one of the things we discussed earlier... this process that we are engaged in is all about finding ourselves and developing ourselves. And that is ongoing and constant.

AAJ: When you are done with an interview, do you catch yourself "Staying in interview mode" with your wife, family and friends, or are you able to switch off and "return to normal"?

LS: Since my wife and my daughter have a zero—tolerance policy for it, that does not happen among us. And, in fact, I think it might be part of the reason I started doing interviews, because I was not getting to do it at home. I do have an impulse to probe and mine people's experience. But I have had a lot of conversations with friends who say "I feel like this is an interview." And I have also had the odd experience of meeting people now who know that I do not know that they know the podcast and tell me what a strange feeling it is to talk to me because they feel like they are on the podcast and in their mind my voice is so associated with the podcast.

AAJ: In its infancy it was not always easy to differentiate podcasts from radio talk shows. Now a clearer identity is emerging. How have you approached your transition from podcast to radio?

LS: My dream was to use the podcast to break into radio, which is like trying to break into the 20th century from the 21st century. It is like back to the future.

What made radio great originally, was that it was live. Radio has an immediacy that fires everybody up. The mistakes are the most beautiful part, and the possibility of failure and disaster makes the triumph even sweeter. I think that was still the case when radio became well prepared. When it became pre-taped and pre-produced we still have that association with live radio. So when you turn on the radio there is that sense of a collective experience with other listeners. Whoever has their radio on is hearing the same thing. A podcast is happening at various times in different places and that is partially why it is hard to picture what your audience is as a podcaster. The other thing about podcasting is that now everybody can make his or her own podcast. It is a bit like what happened to music making... in the past you needed a recording studio and that cost a lot. Now you can record a great sounding album in your living room. So there is a huge amount of podcasts, most of which are made by a couple of people talking about whatever with very little concern for audience or production and a belief that what they had to say was just as interesting as what anybody else has to say.

I approached podcasting trying to make it sound like something that you could put on the radio and it would make sense there. So I did not think that it was going to be a real transition to being on the radio. However, I recognized that when I do radio I tend to assume a slightly more traditional radio persona. Until that happened I had not realized that I was being less traditionally-radio-like in my podcast. I'll learn over time that I do not need to do that on the radio. But I find myself kind of imitating radio people, so if I do an introduction that I know is going to be on the radio, I am more animated, a little cheekier, a little flashier, I think.

The digital age

AAJ: The podcast is a digital age phenomenon. What is your relationship with the digital evolution of music in general, and, in particular the way it has transformed music fruition.

LS: As much as I am trying to break into the twentieth century, you cannot cling to a thing that is not there anymore. You have to find your way through whatever the reality of the moment is. Now I make music on computers. There's so much incredible music that gets made today because of digital access. But the thing that I feel is exhaustion, in a way that I did not feel when I was just starting to listen to music, and I would find just a record or a handful of records to listen to over and over again. You would study it and fall in love with it, and if you ever had a chance to see the musician who was on that record it was such an event. I do not feel that way now. Maybe it is because I am older. Maybe it is because I cannot keep up.

I am a total digital citizen. However, after making music on computers as a boy, in college I stopped completely. I moved to Spain for a while and I was just playing nylon string guitar and insisted that that was pure and I only wanted to make records if I was going to record in the traditional way. I was that way for as long as I could stand to be a traditionalist. I am old enough that I did not release anything on vinyl until later, but I released CDs, and I knew what it meant to have your CDs manufactured and sell them and send them to people. And you know what an important thing it was to have gone through that. Maybe it is because I am exhausted from trying to figure out what to listen to and how to listen to it... But I cannot name an album that I have just been listening to over and over, in a way that, for instance, I can indelibly associate with a certain time of my life. I think maybe that is the thing that I lament more than anything else. It is nobody's fault but my own because it is like our brains have been hacked by so much availability, that we just cannot be trusted to settle down and just listen to something.

The central question therefore for me becomes "How can I quiet my life down enough to remember how to listen?" And I suppose that also speaks to the good and bad of the loss of the label system and what came with it... The gatekeepers who tell us what was important. Of course plenty of people complained that the gatekeepers could get it wrong sometimes and there were plenty of people that were overlooked because they were not given the opportunity. But today, how is that different? Maybe more people have a greater chance, and yet we still cannot find them because they are a tiny drop in a massive flow that just keeps flowing at all times, and how could you possibly find them in the depth of the river that we are dealing with?

AAJ: As far as radio is concerned, for me the realization of its crisis came when I noticed that I was learning much more from Pandora or Spotify than from radio, because most stations had completely abdicated their educational role, playing the same 40 songs as any other station, a problem much worse than what was happening in the payola days. But playlist curation today is more important than ever. Most people do not have the time to sort through the excessive supply that you have described. Some guidance can be helpful.

LS: As an artist, I can tell you that I am very flattered to be in the flow of the algorithm! When, every now and then, I'll see that Spotify puts me next to somebody I admire I think "How cool is that!? That is something that could have been expected by a personally curated playlist!" But sometimes the algorithm makes assumptions about me that I completely disagree with, and that makes me wonder "Why did it do that?" So sometimes I am angry with what the algorithm does to me personally.

Even 20 years ago, my dad thought that the future of curation was going to be very small collections. In his view the record store of the future would have 100 records in it. There's an almost empty room and there would be a person there and he would give you this record... Taking it down to as few options as possible because that is what we are going to really need. In some ways, he was not wrong. We could use a little of that!

Father and son

AAJ: Some of the most inspired episodes of your podcast are those in which you interview your father, Ben Sidran. How do those interviews differ from, say, conversations you two have in the car, or over dinner? Does the presence of a microphone impact your chats?

LS: It is almost the same thing. This means that there is a difference between the tone of my conversations with him and the tone of my conversations with almost anybody else, because my dad and I have a way of talking to each other that is so built into our relationship that we could not turn it off if we tried to. We just have so much shared experience that when I started interviewing him, I needed to make sure that we made it about something specific or otherwise we would start going all over the place and jumping from one thing to another by way of free association like we do at home.

AAJ: Growing up in your household you may have been confronted with the dilemma of whether you should be honoring the legacy developed by your father, building from there, or going in a completely different direction—becoming an accountant or a scientist or something totally removed from music—to assert an independent individuality but losing what had been created before. How did you proceed?

LS: This is something that has evolved so much over time. I have thought about it, and talked about it, a lot. The real struggle of deciding how to assert myself happened through my 20s, until I moved to New York from Wisconsin. I knew that he had done so much. I did not think there was anybody more brilliant than him. So, as a son who wanted to make his own way and make his contribution independent of his father, that was a challenging place to start from. But that is what growing up is all about. I do not even think that it has anything to do with the work itself. It is just the relationship between a father and a son.

I could have indeed gone in a totally different direction, and become a scientist if I wanted that. But, what is crucial to the whole question is that, from a very early age I wanted to be part of the music world. I wanted to do work that was taken seriously. But I also just wanted to be around my dad and his friends, so I had to figure out how to "get in their room." What did I have to say or not say? What did I have to do, or not do, to be able to be invited back into their room?

There's nothing wrong with being a part of a legacy. If you can get there, it is extremely gratifying and empowering to feel connected to the previous generation.

Somebody recently found the liner notes to a Sarah Vaughan record that my grandfather wrote. He was a writer and he worked in advertising in Chicago, but he was a jazz fan, and he did write liner notes. And when I saw this picture of my grandfather's liner notes I thought "So it is three generations now!" It is a beautiful feeling to know that you are part of this ongoing legacy.

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