Lindsay – From Insurance to Podcast Creator

Good morning, good afternoon or good evening, you're listening to career crossroads. And if you're new here, welcome. And if you're not new, welcome back. I'm Jonathan Collaton. And this is the podcast where I talk to one person each week about all the decisions that led them to their current career path. Today, I'm speaking with Lindsay Graham. Now, when you hear his name, you might think of the American politician. But once you hear his voice, you'll recognize him as the podcaster behind shows like American history tellers, American scandal terms, and many others. This was a very cool interview for me, because American scandal has been one of my biggest time sinks over the course of the covid 19 pandemic. Lindsay has become one of the major podcaster influences on me along with Mark Marin. So to find out how he's only recently entered the podcasting space in the context of the length of his career, and how successful he's been since then, gives me hope that there's plenty of room for newcomers on the scene. And if you just put in the work, and provide a good quality product, that's actually interesting. Maybe you can make a career out of it one day. Lindsay has taken more pivots in his career than anyone else I've interviewed so far. When you add that to his natural storytelling ability, which at one point leads to a 14 minute stretch, where I only say one five word phrase, the outcome is a fantastically interesting interview. And the 14 minute stretch is amazing. Because Lindsay makes it so easy for me to do the interview. So enjoy Lindsay's story. And then afterwards, as I do every week, I'll share some things that I think we can learn from my guest. Lindsay, welcome to career crossroads. Thanks so much for taking the time to come on today.

Yeah, I'm glad to be here. Thanks for inviting me,

I am appreciative that you're willing to come on because I've interviewed a lot of people recently who have podcasts. And that's because I'm trying to, to create a certain level of audio quality, given that COVID-19 has really hurt in person recordings. And at least I know that people who have podcasts have their own microphone. But all of those people who I've interviewed so far, are doing their podcast as a hobby, or doing it as a means to promote their own business. And, Linda, you, on the other hand, are a podcaster by trade. So I have to admit, I'm very curious to hear what your career path entails. Because I know me, and hopefully a lot of people who listen to this are going to be really excited to hear how you can turn something you enjoy for fun into a full fledged career.

Well, it's full of twists and turns on probably not that satisfying, but we'll see.

Okay, I I'm at the end, you know, I'll make my judgment after I've heard the whole thing. So

One a scale of one five, how satisfied

perfect, I will let you know at the end. So I usually like to ask my guests to start and tell me what they were like in high school because I really think it's around that age of your life where you start to think about what you're going to be doing next. And so tell me a little bit about where you were, where you were living it. Was that where you were raised? What were your interests? What was your family like? And in what ways did that impact the decision you made towards the end of high school?

Yeah, good question. I haven't really spent a lot of time inhabiting that, that period of my life. Not for any any particular reason I had a pretty good, pretty good childhood. So in high school, I was I started high school freshman and sophomore year, at the boys school, I was attending a private exclusive, pretty expensive boy school here in Dallas. And it was wonderful. I mean, just a fantastic environment to to learn and grow up in. The trouble was, I was a horrible student. I did not like or enjoy working. later on. In college, actually, I was I was diagnosed with attention deficit disorder, which probably contributed to some of these things. But at the time, school was, school was hard for me. And mainly, it was it wasn't a lack of interest. It was just a lack of my own ability to stay on task to do work. I fell asleep in so many textbooks, just trying to get through these assignments. And so I'm one of those kids who was it was pretty smart. And got by mainly by the seat of my pants and never did any work. And, you know, didn't didn't study but still pass the test and how anyone does that? I don't know. So, so my relationship with school actually dynamics and in any any learning of any sort was, was pretty strained it just I just never considered myself. Someone who was good at these things good at math or I liked I liked writing. I liked English, but I never read the damn books that they gave me weathering heights. Are you kidding? I still haven't read it. So my family life was was great. My parents are Australian. So there's always been a sort of apartness, you know, to any immigrant family. Now, of course, being Australian is barely being an immigrant in America. So I'm not trying to put on any sort of air. But yeah, we were we were healthy and pretty wealthy. And I had a great educational experience, but I was doing crap at it. And then I then I actually left that school. You know that it's not entirely clear. To me what the reasons were my parents made the decision. It was in the midst of a real estate downturn in Texas, where we had to move out of our big house and into a smaller house, and my, my father is a home builder, and hit his his income pretty hard. So that was probably one thing. But more than anything, I think my parents just wanted to move me into a new environment, something different, something that might jostle me, you know, get me moving faster in the right direction. And so I went to a local high school, but that local high school was in the most exclusive area of town. So it was not very different from from the exclusive private school I went to, except that there was no uniform, and there were girls. And I honestly, I don't know, which was more terrifying. The fact that that there were females there, or the fact that I had to choose my own clothes. And I did pretty well there too. I in fact, was weirdly voted. One is it the National Merit society president, you know, in my senior year after after being at the school for a year, so I think that tells you something I had, I probably had a pretty good opinion of myself, with nothing to show for it. You know, I couldn't point to my grades or my academic prowess or my athletic prowess. And but you know, I still felt pretty good about myself. Figuring out the difference between self esteem and self aggrandizement is a lifelong journey. But back then, when I'm 1617, yeah. I probably I probably talked more than I walked. That's for sure.

Gotcha. Okay, so it sounds like your parents were making decisions that they thought were going to sort of influence you maybe in one one direction or another they wanted you to? It sounds like maybe try to give you a kick in the pants. Is that why they they switch schools for you?

Yeah, and I know a kick the pants might be the wrong idiom. But you know, put me in a different lane, you know, something

Put you in a different lane. Okay. Now, I imagine that that, like many of us have, your parents had some sort of influence on the decision you chose to make when you were wrapping up high school, because for many of us, it's, you know, university or college, or some people will go into a trade, but usually that become that comes from a place of our parents trying to recommend things to us things that they think will lead to a better future. So what was was that what happened for you were your parents kind of big in the decision that you made after high school?

Well, I went to college, and I went to a college that my father recommended, it was a US News and World Report Best Buy. So he was interested in the value equation of it. He's an engineer. But the whole the whole what next after after high school was in retrospect was really, really difficult. And I continued not doing well. A lot of this was because I was just so unprepared for what life really was. I think I was just oblivious to, to the realities of why I was learning in the first place. You know, I went to, I went to class to go to class. It wasn't an objective that made sense to me that oh, I am I'm learning this to learn it to apply the information or to better myself as a thinker, or to get a job or build a career that would somehow aid me in my fuller adult life. I really shouldn't have gone to college. I should have had a three year gap before I started and and probably should have worked wherever I could have in those Three years to just figure figure that out. Like, oh, you know, it seems so obvious that you have to pay rent and you know, the your car note and buy groceries and, and it wasn't my my parents fault. I wasn't coddled by in any way I just I really think I was just fantastically inside myself, and just had no idea that that there were the cogs and wheels of the exterior world and how they worked. So I was unprepared for college. And and it quickly took a toll. I my undergraduate career took seven years and and yeah, so again, not a good student.

So what was it that you tried to study in those seven years? Did you start with one thing and switch to something else? Or did you kind of go all the way through with the same plan for, I'm going to get this degree and then once I'm done, we'll go from there?

Well, I hope you understand from the story as it's going right now that there's never been a plan.

Yeah,

that will continue that that the the plan lessness of my life is becoming really obvious.

I found you have to ask people what the plan is for them to tell you that they don't have a plan, which works fine with the objective of this podcast. So tell me what your not plan was.

My not plan was well, I showed up a college and and, you know, he's like, Okay, so what do you do, you have to take these classes and and, and, you know, I thankfully had scored well on most of my AP tests. So I didn't even have to take much of the freshmen curriculum. I started by credits as a sophomore. So none of the so I jumped into specialties almost immediately. I didn't have any of the core curriculum required. And that was probably a mistake. One I didn't get to know my freshman class too well, and to I didn't get the the practice of being in a general class. And so instead, I At first, I went straight into computer science and, and you know, actually, I had fun there. For the one semester, I was taking it, except I hated being in the basement of the math department, in a windowless building with these humming machines, and this is in 1992. So there's no internet to speak, we have an email address, but that was like, you know, cutting edge. And so computer science fell away. And also we were learning things like Fortran or Pascal or you know, something, nothing, nothing like today's information technology infrastructure. I always thought maybe I would be a teacher, probably because the only professional models I had were my teachers. And, you know, I had my father who was a homebuilder, an engineer, and I had my teachers who were teachers. And then then maybe I, I started it started taking history classes, and I started taking psychology classes, because maybe I'll be a therapist, which is kind of still a teacher figure. And, yeah, I didn't have a plan. I just took some classes. My plan was to was to look at what was required and fulfill the requirements. I don't I don't know why they accepted their requirements. So just keep checking the boxes. And and that's how I spent the last the first several years of my college career.

He said it took seven years to get through and get that degree. And is that because you were taking so many courses in different subjects of study that you had to sort of add to the number of credits required to graduate or did you just take less courses each year?

All of the above I failed a few classes that I need to retake because I just never showed up. Never did the work. Then Then I you can imagine that this is this whole time of aimlessness and poor performance started to take its toll on me and my emotional health. And so eventually I just stopped I just stopped all of it. It was it was I had so much more fun not being in class and not being so tortured by what I wasn't doing. So So yeah, I guess I just dropped out. And that's when you know, the real living happened because at that point, the college funds were already pretty low and and i don't think my father wasn't going to allow me to to subsist on what was supposed to be my college savings. So I had to get a job. And luckily in Fredericksburg, Virginia, I went to what was then called Mary Washington College. Now it's the University of Mary Washington, but it's in Fredericksburg, Virginia, the birthplace or a certainly the hometown of George Washington. And Mary Washington is named after his mother. There's also thankfully a regional Geico call center right there. So they're always looking for young, abled, able bodied voices really people to show up and take and sell insurance take calls and sell people on their insurance. At the time, Geico was the largest, if not the only direct insurance sale as seller, everything else had had the traditional agency model. And so it was a, it was pretty easy. You showed up and took your orientation, did a little bit of study got your your your license to become a property and casualty agents agent in like four states, and you sit down and put a headset on and eight hours a day you talk to people and try and sell them car insurance. That's a it was not fun. You know, I didn't mind it so much, it was a job and I got I got what you should get out of a job, mainly a paycheck and a place to be. I made some friends at work. But he was pretty, pretty obvious to me that after, I don't know, a year and a half, two years of this, that, that I wanted a lot more than than being, you know, in a call center. And so that's when my returned to college, you know, happened, but I at that point, I had no more money. And, and so but Geico had a tuition reimbursement program, that if you were working full time, you could go to college, and they would, especially State College, which Mary Washington was, they could they would reimburse your tuition expenses if you took business classes. And so that's what my major became, I'm now a business major. And you can see that I never made a single choice ever. All of these things just happen. And and and I just follow the flow. So okay, I'm working full time to arrange my schedule, I often worked long, like 12 hour shifts, four days a week, so that I can be back on campus at school. And finally, finally got my undergraduate in, in business, but even then I screwed it up. Because when I thought I was graduating, I got a call from the University Registrar. That because I had taken so long to graduate, the the curriculum requirements have changed. I was missing one class that I didn't even know I had to take. But I was so furious and fed up. And I'd already quit my job at Geico. Because I had imagined that I was graduating. And all of a sudden, I wasn't. And I had, I had made arrangements to leave my house that we were renting. So this was just crappy. So I did, I left, I left Fredericksburg, and went back to Dallas. And thankfully, the class I needed was some very low level business course that I could take at a community college here in Dallas and transfer the credit. But you know, it added another nine months of administration to, to my graduation date. So that period was not fun. Not certainly not efficient. And, and, gosh, I know, I lived through a lot of that. But I can't say I learned a lot. I'm still I was still much younger than I was I was in years.

I wish that people could see this as we record this over a webcam because I was just laughing along with you there. But I didn't want to interrupt because that was it's such a realistic story. Right? Like, I work at a university. So I work with students and and when I was a student myself, I could tell when I was an RA in residence, I could see that there were students who were there that they just, they shouldn't be there sometimes. And they weren't really in it, they were just there just experiencing it. And, and so I can I can relate to that story. And, you know, for myself, I, for me, the academic side of university was just something I had to do, so that I could get through all of the other parts of the university experience I enjoyed, which was all the extracurricular involvement, and I knew that my career was probably going to be in that field. So the courses were just things that had to happen. And I've also I've had friends or herd of people anyway, that had that same situation where the requirements change on them, and then they have to have extra time to graduate. So it's an unfortunate reality right that a lot of people have to have to deal with. So when you're done that you have your degree. And you mentioned your plan was to move back home so you move back home and did you very quickly find another job doing insurance because that's what you had experience in or because you had that degree now did you did it kind of open up doors for you a little bit, you had a little more variety in what you could apply for.

I had the whole semester of this extra course to do in, in Dallas. So I couldn't go around shopping for jobs that required a degree or boast of my new new credentials. So yeah, I just hung around and waited tables went to school for this, you know, six to nine month period. Eventually, I got a job at a high end plumbing and fixtures store. But in the back, I just needed a job and, and so I was I was working with with a bunch of other guys who and we stocked shelves and and drove things to job sites. And I learned, I learned a lot about plumbing and doorknobs. Eventually, though, I did get my my degree. And eventually also, I worked my way into the Accounting Office of that plumbing and fixtures store. As they tried to modernize. And I tried to use my business degree, we discovered that they were losing a lot of money by just really poor inventory control. And so we opened a centralized warehouse for the three stores that they had. And then I managed the warehouse, which you know, wasn't exactly fun, because I was alone in a warehouse full of toilets. And then a truck would pull off, and I would load those toilets on or off the truck. And then do all the accounting and the paperwork, and inventory, etc, etc. So, you know, while while that was good, and seem to be some sort of trajectory forward, I actually I started to understand and enjoy building things. Where, where this system did not exist before. Now it does. And it's working, it has it has benefits, and I can point to it, and I you know, was the one who built it. So this is this is an interesting thing that I'm starting to learn. I like these systems, and I like building them and I like enjoying that I built them. But again, you know it what I built is a warehouse with the toilet, so so I did start looking for other jobs, and found one in the kind of financial reporting department of a company called pavestone. That that since sold to someone else, but anyways, they made interlocking concrete bricks in the one pavers, you've probably walked on hundreds of millions of them. And so I had to learn, you know, a fair amount about that industry, but also, I started learning SQL, you know, the computer programming language language database, in particular, querying language and my Microsoft Access and I, you know, I, I got the job by bluffing my my way through it by saying, you know, of course, I know Microsoft Access. And, and I was terrified that they would test me on this. So I took a quick course. But the course was all on the front end of Microsoft Access, if you know it, it's more like it was like kind of form designing. And it had nothing to do with the back end the actual tables and relationships and queries that you build there. So I showed up thinking I was going to build data entry forms. And that wasn't the case at all.

So two things I want to mention there. One is, I'm sure you've heard the phrase fake it till you make it, which is very, very popular these days. And so it sounds like you did that quite successfully. But the other thing I just want to say is I love when I'm doing these interviews, and I can pinpoint out quotes that I want to use to promote the episode before it's even done. And I was alone in a warehouse full of toilets is 100% One of the quotes to promote this episode. So thank you for that.

You're welcome. I will try to give you as many zingers as possible.

Perfect. Anyway, continue.

So at pavestone I'm working and but I again, I'm not really interested in my work. It's It's It's a lot of straight ahead accounting work. It's a lot of working on these these queries. And one of the most, you know, boring portions of the work is is when every month I have to dial up via ISDN all the branch plants throughout the country and just download their financial data and upload it to the corporate core. Right. And so this was so tedious. It was just so manual and tedious and they gave me big instructions and so so I wrote a batch file, an executable script that would would do most of the work for me. I screwed it up. And you know, I mean, it was simple as simple as a misplace common or something. And, and so I imagined that I would take these lists of files, copy them to a temporary directory, move them over. And then once they're done, erase the temporary directory. Well, all of that worked, but I also erased the original directory. So the, in the middle of the day, you know, our Chattanooga factory starts calling like, Hey, we can't get anything done. It's everything just shut down. And, and they're looking around, it's like, Well, the reason is your tire database is gone. And yeah, so that was my fault. And after, thankfully, it was recoverable. You know, they did have some, some measures in place. But it was quickly found that I did not have the requisite focus for the job. And so i was fired. This would be the second time I was fired. I was fired from Red Lobster when I was in, in college, because I missed a shift. And I was fired for almost destroying the entire financial records of a concrete manufacturing plant.

Yeah, that's not a tiny mistake. That's like throwing a stick of dynamite in their filing room.

Yeah.

As you said, you're lucky, they were able to recover it.

Everyone was lucky. And, and so. So I was fired. And, and I didn't have I didn't have a job. At this point, I was paying rent I was, you know, a young adult, what how old would I be, I'd be probably be 2526 something like this. And in didn't know what I wanted to do. I was able to to get unemployment for a bit. So that gave me a few weeks. But then this this weird opportunity to, to go on a long trip to Australia came up, some friends of my family had put together these trips that they'd go on. And so they're my my parents age, but one of them fell out and couldn't get reimbursement on the on the tickets. So, you know, free airfare. And so I went to Australia for about three weeks, and did nothing except kind of think, and visited some relatives I hadn't seen in years. And then one morning, I was I was staying with my cousin in Melbourne, and was woken up by her. And she frantically pulled me to the TV. And we turned on the news. And there's a plane flying into the World Trade Center. And, you know, because of the time difference date assembled all the tape that they endorsed, and they were able to find and and just going over the entire day that happened while we were asleep. And so, you know, all four planes were, were were shown in some sort of horrible succession of violence and horror. And, and then I had to get on a plane and travel to Sydney. And and so when I got to the airport, it was just the spookiest thing because they, you know, we knew that they shut down airlines in the airspace in the United States. And the Australians were were very kind. They asked if if I was okay as an American. And, you know, there was, it was one of probably the, the one time in which an American passport really gave you sympathy rather than me. And so I flew to flew to Sydney and walked around. And it was just the most surreal day because I turned a corner and bumped into the American consulate. And I swear to God, there was bagpipes in the distance playing Amazing Grace. And the consulate was littered with, with flowers that you couldn't walk up the steps, you know, and just just a really bizarre day, and kind of set a mood for for me and that trip. And eventually I came back, I was lucky to catch one of the first flights back. And so I needed to kind of restart in this weird moment in which a lot of Americans needed to restart. Yeah, that's when I got a a phone call from Southern Methodist University I've been applying to jobs all over the place. And they were looking for an analyst position doing pretty much much the same thing I was doing at pavestone. And and they liked my resume and resume and would I come in for a interview that went well, you know, and I had to explain to them why actually got fired from pavestone. I was totally upfront about it. And so they asked me though, so why did you leave? pavestone? I was like, Oh, I was fired. And here's the reason why I made a horrible mistake. But they hired me anyways. And I stayed there for 10 years. And, and grew more and more discontent and hemmed in that entire time.

Did you feel like that from the very beginning? Or at the beginning was it...were you just happy to have a job to found?

Not only was I happy to have a job, but I was, you're happy to start anything new. I mean, yeah, there's there's always a honeymoon phase. But in general, actually, I did like the job. It was more of these building systems, kind of tasks that I had already identified that I liked. And every single little report, a query that I had to build was a miniature system. And I was quite good at it. So I started getting special projects and larger projects and more responsibility, and we'd be pulled into more and more meetings. But there wasn't a career path that it was, it was, you know, like, where do I go? Do I get my boss's job? No, I don't know, you know.

It was just a job.

It was just a job, there's certainly wasn't any obvious path forward. I could look for, you know, ways out of it on the sides. But no, you know, you just you just got a job. And university life is pretty good. The benefits are nice. And you know, every year you almost every year, you get your 3% cost of living increase. And there's a lot of vacation and holiday. So, you know,

We only got 2% cost of living increase up here. So I guess I need to come down to the States.

Yeah, so it really wasn't that bad. But I was getting itchy. And there was one moment in particular in which a, thankfully, I couldn't tell you her name, if even if I tried, but their co worker that I was not impressed with, I did not admire. She reported that that she was going to start her MBA program in the fall. And that's another perk of working at a university, you might get a graduate degree for free. And I was so incensed, so outraged that this person who I did not admire, was going to get a graduate degree in business. And I wasn't. It was the most petty, Petty thing ever. But it drove me to take the GMAT. That weekend. I didn't study didn't prepare, didn't score that well. But I scored okay. in a, in a bit of a reversal, my language score was higher than my math. And it's always been the opposite to that. But it was enough to get into the program. And, you know, it was just, I mean, seriously 72 hours of freakout to take this test and get my application in. So I could be in the same so that so that this woman wouldn't get an MBA before me. I yeah, I didn't know her. Well, I it was just, it was just like this thing that this this igniting this event, this you know, my fuse was lit. And I did the most irresponsible thing and got it all done in three days time. So now, so now I'm a graduate student, starting in a couple of weeks or something like that

Full time?

No, no, it's a professional MBA program. So is, you know, nights and weekends.

Gotcha.

While while I work. And so this is probably closing in on 2005. Anyways, I got finished the program, still working in the university, now have an MBA. And right at this moment, the leadership changes in the department at the University I worked in, in development, fundraising, for them, marketing and in particular. So I was able to, at this moment, have conversations with a new department leader. And just flat out mentioned that, well, I now have an MBA, it's I am now more marketable than I was before. And so can we think about crafting a position that that uses that uses me more. And he was totally open to the idea had really enjoyed working with me on some other projects that he and so, yeah, we we created a position called the Director of Business Intelligence and market research. And so I I became my my own sort of department, I had no employees and I had no bosses except for him. And, and then immediately, he left, he left for Wake Forest or something. And so, you know, became this, this, this weird situation in which the person who I had crafted this position for who I thought would be my, you know, my mentor and teammates is just gone. And, and the universities, you know, kind of does a pivot, they don't hire anyone new, they just kind of rejigger the the upper echelons. And so now my boss is someone else. And now I do have a boss, I'm placing a division anyways, that the plan didn't didn't work. But I, you know, I got the bonus, you know, a bigger salary and still some interesting work. And that went on for years. It was a job that I could do, probably quarter time, if I could get all my work done in in two days. And, and so it wasn't. That wasn't the best thing. Because if I'm not busy than then I'm not centered or present. And so I just wasn't feeling good about the position. I wanted to know if there was more for me.

Had you felt like the jobs you had prior to that, they were....did they keep you really engaged?

Well, they kept me busy.

Busy. Yeah, that's,

that's sure. I was no engaged, no.

But busy. And I asked that just because it sounds like, up until you mentioned before, we were talking about having a plan and that there was no plan. And then even when you It sounds like when you got that job at the university, it was because that was a job that was offered, right? And so it's and it fit with your skill set. And so you took it. And then all of a sudden that that colleague who went and wanted to get that the MBA, that was the thing that prompted you to get an MBA, but then from there you went and approached management about creating a position for you like that sounds very much like all of a sudden, there is a plan in place, you knew what you wanted?

Yeah, you're, you're identifying a shift in my behavior and thinking and that probably came through through the the MBA coursework, I really enjoyed it. I was interacting with people who are in a much different corporate environment, you know, professional environment, people from DuPont, and you know, McDonnell Douglas, and you know, McKinsey, and just large firms doing large things. And, and, and I was good at the schoolwork, I was pretty, pretty clever. And this is, this is probably the only time I still didn't work that hard. You know, to be honest, there was there was one class in particular that I looked at the syllabus. And I'm gonna say this out loud, and it just seems so preposterous and obnoxious. I looked at the syllabus, and just said, I'm not doing any of this. And I didn't, I didn't show up to class until the the final, because, you know, he Silva said that there's no homework, there's no turning in anything. The final is your only grade. And I said, perfect, I'll see you then. And that's exactly what happened. And I did well in that class. So yeah, I still haven't gotten to be a great student, I'm still getting to the end, for the sake of getting to the end, you know, the the degree is still the objective. But along the way, I did meet a lot of people with different ideas and different careers and, and really enjoyed many of my teachers, who at the graduate level, are, are much more interesting. And, and I was much older, and the material was, was connecting with me, I'd already spent time building these systems. And now I see that there's, you know, an entire world of system building that makes sense, and is available to me. So yeah, you're probably right. I took those lessons and went back to my current job and asked to build more systems. And it almost worked. So, so yeah, I think that's probably the beginning of a difference in my outlook to the world and certainly, how I looked at myself.

Okay, yeah. So then you end up in that job that you had created, but then there's just sort of not enough of it. And like you said, you could have done it a quarter time or two days a week. So how long did you last in that role? Because typically, when when I find that people get into a position where they're really just not engaged. Sometimes you get out of it pretty quick, and sometimes you stick around because you don't know where else to go. But what was it like for you?

Well, I stayed about four or five years. So, you know, again, it was very comfortable. I was making the most money I've ever made in my life. I was not working that hard. I was still doing good business. Good work. I was. Yeah, it was, it was nothing to complain about, except it just wasn't, wasn't much of anything that that made me or I would identify with. You know, the only thing I liked about that job was probably the title, Director of Business Intelligence sounded awesome.

Yeah, that does sound awesome.

But the job itself wasn't wasn't that impressive. I had a lot of great teammates, I love my team. And they, they were friends and co workers. So that was, but you know, I've always felt outsider ish. Just about in every single environment I've ever been in, that's probably my own introversion and my, like, we were were identifying I have a very, very oblivious insular tendency to just think about myself. And, and not really, really become part of my environment. So yeah, that lasted several years, until I finally grew to tired of it. And, and, and then kind of manufactured another job at an insurance company that that some friends were working at. This was very small company. But I got to be in charge of marketing. And but I, to an extent, I think I got duped. There were four executives, you know, CEO, marketing, operations, one other person, and then some other employees, but the industry was the product they were selling was just exploitative. It's a d&d. So Accidental Death and Dismemberment insurance, that's, that's sold as part of a package that you might get with your credit union. It's direct mail stuff, and no one really should be buying that product. And so from the outset, I was like, shoot, I've just, I've just become part of a problem. No, I'm now I'm not really a scam artist, but I'm really close to it. And my job is to, to, to make it as effective a scam as possible. Because I'm writing the damn direct mail letters, I'm designing the forums, I'm building the the systems to, to catch these people more efficiently. So really quickly, and plus being so so small, there wasn't the the, the organizational, organizational rigor, necessary to to really move forward and didn't I there was a personality clash with the CEO. So I as I shoot, I've gotten myself in trouble. This isn't the right thing. But I've been looking for a job for so long. And I finally got a new one, I was out of the university. But within months, I was like, so I was a little afraid to go looking elsewhere. Although I eventually started, and I started getting some nibbles. I was like, You know what, I really want to be more in marketing more in advertising than then client side marketing. I want to I want to be creative, I want to do more. And I think, you know, at the time I was dating, the woman that who would become my wife, and she was in advertising. And actually, my sister is in advertising and I dated previously, other women in advertising. So I knew the industry. So I thought that's where I needed to go. And I took a bunch of bunch of interviews and made a lot of applications and was moving but slowly, and along the way, I grew more and more indifferent to my actual job. And it was so lacks, that that people were coming and going whenever they wanted to, and, you know, work never suffered, but it it just felt like almost everyone was not there on a Friday, or coming in at 10. And, and so after a vacation that that I took, I came back and then had a doctor's appointment that I didn't tell anyone about, you know, I actually did have a doctor's appointment, but I didn't show up until like 11 and, and my boss just blew his top and and so I was fired. This would be the third time I got fired. And it was a bit of a shock. You know, there wasn't any of the regular warning, etc. It was just a an emotional decision made very swiftly. But I went home and at this point I was married and And I told my wife, you know what, let's, let's try I want to try and make audio, a career. Because all this time, all this time, I've had this little studio that I'm in right now. And in the back of my property. And I all this time I've been recording bands in Dallas and playing instruments myself and composing music for radio and TV and I've, you know, even filed, create a little LLC called junius recording company and tried to make it whatever small business it could be. But, um, you know, it was just, it was a hobby that paid for itself. But now now, you know, we're a two income family. I've got a small window perhaps to make try and make something in the audio world. And I thought it would be you know, recording for voiceover not not me voice wrote, you know, doing the voice but other voice artists for commercials and editing and that and doing radio stuff and maybe writing a few jingles. Who knows, but I wanted to figure it out. Right at that same time, someone contacted me looking for studios to rent, because they wanted to build a audiobook business in Dallas, he was had worked for Audible for a while in New York, New Jersey, and was coming down with his wife to be closer to her family, and wanted to start his audio business, but it was centered around audiobooks. And honestly, you know, I hadn't really thought about that. But he'd been working in it for years. And it turned into, you know, a pretty complimentary skill set. He had expertise and connections in the audiobook industry, and I had a studio and a business degree. And so it's like, well, you know, damn it, let's let's see if we can't make this kind of work. And we did, we worked really hard. The problem with audiobooks is that there are low margin business, and you have to do enormous volume to to really make any, any sort of livable salary off of them. And we were always minute middlemen. We weren't the talent reading the books, we were we weren't the editors doing the editing, we are just the producers managing all the moving pieces. And we weren't doing enough so that I could charge this new company rent on the studio, you know, there just weren't opportunities to make too much money. It was it was it never made money. I mean, overall month, a month, there might have been a few times in which we took some paycheck. But no, I never made money. But it did capture capture the attention of a startup incubator here in Dallas, called wildcatters and, and so I don't know why. But my my partner, a co founder, he is really good at hustling. And this is one of the things he hustled was a position in this incubator program. And so the way that works is they give you pretty much access to investors and coaching in how to how to, you know, build up scale, a startup in exchange for some money, seed capital and and you give them I forget what it is 13% of your company or whatever. These incubators are all over the country, it's you know, pretty, pretty standard. But I never understood what the hell they wanted in an audio book company, because it couldn't scale like like they wanted other things to scale. It's not a software company, you're not selling units, you know, you know, we're not selling the books, we're producing them. We were than in the wrong place in the industry to try and scale up. And it was also during this time that that my co founder and I were increasingly at odds. I felt that I felt that I was being taken, taken for granted that my creative input wasn't wasn't regarded that, that I had a whole lot more to offer. And it wasn't really being respected. And and this became more and more of a problem. And strangely, it became came to a head when we put together our first podcast. As an audio book company, we wasn't really a strategy, but we we thought getting into podcasts might be a good idea. So we started fishing around for ideas for things that might work. commercially, you know, as a calling card for our for our founding company, and but my co founder wanted to do an audio drama and I had never even heard an audio drama other than other than probably the the PBS version of Star Wars in the 80s. So okay, fine, let's do an audio drama and, and we cast around. Because luckily I was involved in a bunch of theater and knew a bunch of improv comedians as well. And this was kind of my, the group I ran around with after hours. So I was deeply involved in local music community in the theater community. And so I had plenty of friends. And we just asked if there were any ideas, but but none of them stuck more than this idea that I had, which eventually became the audio drama Terms; a tale of a two term president who does not want to relinquish the office to his incoming successor, because he's a populist ideologue who might endanger democracy in America. We were writing this in 2015. We had no idea that Donald Trump was going to come down that golden escalator but he did. And, and, and caused great problems, you know, because he aren't our our character. Donewalke, Charles Dunewalke who was a, you know, fast talking New York millionaire, came out with a campaign slogan called America First. And and then, seriously, two weeks later, Donald Trump does the same thing. We had to rewrite it, or at least contemplate rewriting it. Anyways, we, we made up this story, and it became a little too, too real. And we were shopping right around the time the 2016 election. We had three episodes in hand, and no one wanted it is like everyone's tired of politics. No, they're all there, they've done it. But this was also when everyone expected Hillary to win. And when she did not, we got a call from from wandering Hernan Lopez The next day, saying, hey, do you still have that audio drama? Yes, we do. Great. I love it, I want to put it out. And, and so that's how I I, that's how I became a podcaster. For real. I skipped over the part where I had a podcast in 2005, talking about local music, but it was 10 episodes, you know, and then we were out. But yeah, all of a sudden, I'm the executive producer of an audio drama that's being released by Wondery, a company out of LA run by the former Fox TV international CEO. And it seemed like a big deal. And it was a big deal. Terms was put out. But it was an audio drama. And they don't get the same sort of audience or and advertisers don't understand them. And so while we were over the moon with the response we got, and we have our picture in the paper here in Dallas and some other things, some interviews. The podcast itself did not perform well commercially. But that was that was the first podcast. And more than anything, it it was the entree to the rest of my career because it introduced me to her Hernan Lopez it and Wondery,

I'm really excited to get to the rest of your career at Wondery because that's how, that's when I became aware of your work. I don't even remember exactly when it was but I was looking around for podcasts to listen to and I came across American Scandal. And listened to I think the firs one I listened to was the Exxo Valdez story, which happened th year was born. So it wa something I was kind of aware o as I was growing up. And I' heard about this oil tanker u north that crashed and maybe learned about it in school. Bu I listened to the that series o American Scandal and I was like, oh, wow, this is this is my kind of thing. I'm a history guy. I studied history in university. So hearing these old historical events, and really not even old, modern American history, but that was really something that hooked me and COVID-19 meant that I had a little more free time. I couldn't go a lot of places. So it was certainly more time to sit down and do a puzzle and listen to American Scandal. And that was the first time I ever heard of laundry and I'd listened to podcasts before but usually they were on the realm of you know, local sports anchors get together screw around, making a podcast and and a few other interview style podcasts that I enjoy. But American Scandal was new. And I just went and tried to listen to terms the other day and I found that I couldn't pay attention to it. I was trying to listen to it during work. And there's just a lot going on there. And I couldn't do work and pay attention at the same time. So something I'm going to have to try and pick up another time. Something you said, I think is funny. When you said that in 2016, nobody wanted to pick up terms. Because you know, people aren't are over that. Well, the next four years, probably burn people out a little more on politics. So it's, it's funny to me that it got picked up then. But I do wonder if it would be successful now. And, you know, something I've noticed over the last number of years, I could see the downfall of the show House of Cards, which is obviously very political. And I know, there are other reasons why that show kind of took a downturn, but I think that the show writers just couldn't write a show that would surprise people anymore.

Well, you know, I get asked often enough, if there's a second season to Terms, because we kind of ended on a pretty big cliffhanger. And we had already always, you know, intended for there to be a second season. But you know, I did mention it wasn't really commercially successful. So there's one big hurdle but also you're you're right. The last four years just competed with our, our imaginary political world. We we wouldn't I don't, I personally didn't feel like exploring this any. This world in which the entire country is rent asunder, you know, when it seemed to be happening. And so I, I wasn't too and personally invested in it, but also because I had other things to do, like American History tellers, which is, which is what Wondery brought to me. I was going through some emails actually, just just recently, last last week, and I found the email in which Hernan asked to set up this call. And, as I and he wrote me is like, Hey, sorry to not have been in touch too much in the last few months. But I have some things to ask you two questions, when would be a good time to call. And so so I take this call, but at the at this point, I have left my audio company, I've gone through a business divorce with my co founder because it was just was untenable for me. And, and it wasn't fun. And I went back to the university, got another job. But it wasn't my fancy pants. Director of Business Intelligence job, it was actually probably a step down in marketing. But I was back with all the same people and I knew I knew the I knew I knew the layout of the office. So it was kind of easy. But it was such a defeat. Yeah, just just a bit of a heartbreak when I showed up that first day. And you know, I was glad to see everyone and everyone was glad to see me. But you know, it wasn't a victory that's for sure. So when so when Hernan called just a few months into having returned to the university, I didn't know what he wanted. Terms was over. I was out of the audio game. How could this? What's going to happen here? Hernan had two questions he asked me first. They have this new podcast coming out and the host is a journalist so contractually cannot endorse products in ADS. And Hernan has always liked the ads that I wrote for terms that he likes the sound of my voice. He likes the way I write ads. Would I do the ads for dirty john? like, Sure, absolutely. Let's come to some sort of contract for how much I would charge for that when we did. And you know, it's not a bad voiceover gig because it's a weekly show for runs for a while and but it was a limited series. It's not a career app. But the second question he asked me was, hey, you're a history buff. Right? And, you know, I've told this story before but I said yes. I certainly was for the purposes of that phone call. And you know, I I was history interested history adjacent. I liked history. But you know, it's been a long while since I've read any books and I think it's great. Well, you know, we were having some success with this history show called tides of history and, and that's written and hosted by Patrick Wyman and actual accredited academic historian and we've also had some success with these shows. run by Mark Ramsey. These inside Hollywood is inside jaws are inside Star Wars. And I think Hernan says, I think I can combine the two of them, make it an American history show and and really have it take off. And I'd like you to host it and do the sound design as like, Well You bet. Absolutely. That sounds like a great idea. Let's Let's, what sort of show isn't and and then we just started talking, you know what, what sort of show isn't. And I go back over those early emails and we're just batting it back and forth. I think even in that first phone call he asked like what what should the first season and and I told him the Cold War because if you remember in 2017 first few months of Trump's administration, we had some saber rattling with North Korea over their nuclear program and Russia was not looking nice. liat us and as like this feels reminiscent you know, we haven't had a nuclear arms race or problem in a long time. So yeah, let's let's do the the Cold War. I think it's it's something that people will will want to look back on. And especially in this moment. It's weird, geopolitical moment. And he agreed. And so we just kept talking about he went off and found a writer and sent me a script and I didn't like it. I didn't like it at all. And he asked my opinion, so I so I told him and I told him why I didn't like it. And, and he says, You know what, I agree with you. We'll keep looking. And then we found a good writer, Audra Audra Wolf, who wrote the first series for American history tellers. And we just kind of over a two month period 60 days invented the show. I'm thinking back about wonder no wonder he just sold to Amazon for something like $300 million. Hernan is no longer the CEO, you know, he's retired. I'm not sure if he wanted to do that. But that's the consequence of the sale. So way back then when wondering, in 2016 17 Wondery was not that company. And Hernan was doing a lot of this work on his own. And it's fun to see that trajectory just over the course of five years, four years. But we built this show, and it went through its its series of revisions and and something and we're racing to the end, because we sent our release date. And, and, and then it releases on on January 2 2018. And then on January 5, it hits number one on on iTunes. And this was not something I expected. Did you know, I don't know if or not unexpected, but it was it was wonderful. Suddenly, the biggest the biggest podcast in the country was mine. And I was doing it nights and weekends after I finished up at the at the university. Oh, and I have a newborn child too. He was probably just approaching when this is 2007 is 17. So So is 18 months old. And yeah, American History Tellers just takes off and wandering puts me on this PR tour, I do a lot of interviews, I have to fly out to LA and to be on some local TV program for a bit. And, you know, it's fun and a bit glamorous and totally exhausting. And all the while it's a weekly show. So it just keeps cranking. Okay, keep going. And it's it's getting hard for me to, to edit the scripts, get them to where I think they ought to be because no one knows what the show really is. As soon as the Cold War series was over. We were onto a new series with a new writer. And so we that's a completely different voice and different skill set. And and it was it was hard in the beginning, we were trying to find the footing for the show. A lot of work went into conforming those scripts to to what was what we thought was a good show. And then I have to record it and then I have to edit it and then I have to sound design it and I you know composed and performed all the music for it. And it was it was exhausting. It was it was tough, but the most exhilarating thing in the world. And I was getting paid for it. You know, I was on contract with one jury and they were paying me a pretty, pretty good salary. In fact, it surpassed my university salary if you an analyzed you know, annualized it, but I wouldn't annualize it. You know, I was on contract for a certain number of episodes and there was no guarantee for renewal after that and which it makes total sense. If it's a bomb, you don't want to wonder you shouldn't be obligated to keep going But it was too much risk for me to, to make some sort of bold move. I did, I did hire a freelancer to help me edit eventually, you know, to ease the time burden. And that helped out a great deal. But it was it was getting to be a lot of work. And, you know, I was away from the house often. And I just started thinking, you know, I can't quit my job, because it's an irresponsible thing to do. Because I have no idea of history tellers is going to go away or not. But if there were a second podcast, if there were some other thing that was like it, and I could quit my job because I would have this kind of, you know, this safety of a portfolio effect you know, the likelihood of both podcasts going away would be lower than you know any one of them going away. And and History Tellerrs was such a success. Maybe I can do it twice. And so honestly, that's that that's what I did. I went back to Hernan at Wondery, I said, I've got this idea for a podcast that takes the methodology of American History Tellers, and marries it with with kind of the markets infatuation with true crime. I'm calling it American Scandal. And it's not as salacious and murdery. As, as you know, the rest of the true crime world is but you know, we're gonna look into the back alleys and the dark corridors of American history and tell these stories. And here are some sample stories that, you know, we could tell iran contra was the one I wanted to do first, it turned out to be the third series. But Hernan liked it. He bought the concept from me for not much money, but I didn't care because that's not what I was there to sell. I was to get there to get myself another, you know, contract. And so. So it started moving forward. And the same process happened again, I was put together with a producer of the show, and we hashed it out over a couple of months. And then pretty soon, you know, within the middle of that year 2018, American Scandal came out, and it hit number two on the iTunes charts. Our timing was bad, because it came out the day after season three of Serial. Yeah, so. So we never, we never got to number one for scandal. But I had fulfilled my objectives. I now had two shows, paying me twice as much as I was making at the university, the risk was higher, but the reward was higher. And suddenly, I was working with all these little doodads and microphones and stuff that I had been collecting and loved. And I was taking everything I learned from the audio book experience and terms and had an opportunity to build my own business. And just things started clicking. So yeah, I don't think I was ever happier. When, when that really started happening.

I'm glad I'm glad you said that. Because that's kind of what I was, I was hearing from you. And it's making me think that this hobby for me, this is just a hobby and I used to think that like my nine to five job was what would give me the stability to live the life I wanted and to the security of a university job, you know, the value of all that. And then when I started doing this, I found that didn't really bother me that I was working a bunch of hours on evenings and weekends to, to go talk to my friends about their career path and, and then doing all the editing. And, you know, I'm still kind of an entry level podcast editor. So it probably takes me longer because I'm still learning as I go. But this kind of became my happy thing. And then my day job is my paycheck. And, and I hope my boss doesn't hear this, but I think she knows that I'm kind of ready to move on from that job. And so yeah, it's just good to hear that something like that worked out for you. And you were able to make a career out of this. So you've got the two podcasts, and at some point you just decide like, the risk reward is balanced itself out and, and lives better just doing what you want. So you leave the university?

Yeah, I leave the university I remember distinctly telling my boss and giving her a month's notice. And yeah, it was it was good. I felt really empowered and quite accomplished. And that's this was, this was something that I had done even though obviously anyone listening to this would would just You can stack up all the, all the accidents, and you know, this is luck. But looking back on it, when it mattered, I took, I took advantage of those, those opportunities. And I did make enough decisions that I can say, Okay, this is actually mine, I did really build this. A lot of things came my way. But I have a lot of talents that made it happen, that I didn't quite lean into anywhere else. I have some interests that were particular to this, this job that not many other people have. So yeah, I'm not boasting here. I am trying to reclaim my career path, saying, Yeah, it is mine. And that's probably why I'm so proud of it. And why I'm so fulfilled right now. It's a lot of things. It's just mine. I've built it. I've gotten two employees now. I've got, I've done how many 12345....7 podcasts altogether. Three are running concurrently. They're all doing really well. And, and so now I'm just looking for more next things, I get to build more systems. And, you know, this is funny, a bit of an aside, back when I was unemployed, and before I went to Australia, I took one of those career tests, like, cuz you're lost. And I'm asked, what should I have been? You know, let's find out. And it came back as architect. And I was so bummed out, because it felt so right. Like, of course, I've always been interested in my father's engineering, his buildings and the homes that he built. They've always been fascinating. And and building stuff. Yeah, God dammit. And you know, I can draw, okay. But then I, you know, did some research and it takes like, forever to be an architect, I'd have to go to school again. And this is right after I came out of my miserable, miserable undergraduate experience. So I said, there's just no way I'm going to be an architect. And that sucks. Because apparently, this test tells me I'm supposed to be. But when I look back, when I'm happy, when I'm fulfilled in my work, it's when I'm building things. And I think And not only that, it's it's when I'm building things, when where people inhabit. I'm not building a monument out in a desert, you know, a monolith to be discovered in Colorado after my death. You know, I'm, I'm building things that people will inhabit that people go to that they'll experience. They're not buildings. It turns out they're stories. And, and I love it.

Well, Lindsay, that is what I call closer right there. Because I think it brings us to the end of your story today. And so I just really want to say thank you for sharing your whole story. I haven't. For the most part, I've talked to people who are a little bit earlier in their career path than you and they don't really want to share about the time they got fired. And so it's it's nice to hear the reality that it happens. And your career isn't over, and you'll find something else. So I really appreciate you sharing that today.

Yeah, you bet. I was glad to talk about it. I'm surprised that I've talked so long. But you know, that's what happens when you work for 30 years, I guess. 25 Thank you so much. I enjoyed this conversation.

All right. So I hope you enjoyed that because I know that I did. I really wanted to hear how Lindsay's work with Wondery began. But everything up to that point was just fascinating as well. Sometimes in these interviews, I have to dig a little bit to identify the catalyst of change in some people's career. Lindsay, however, is pretty self aware and can look back on those moments in his career and identify why they occurred. Having said that, what can we learn from Lindsay? The first lesson is that you can adapt a skill set you have to fit vastly different jobs. Lindsay enjoys building systems that came up numerous times throughout his interview. And it was very clear at the end that that's how he sees what he's doing now building podcasts. Think back to the beginning of his career after Lindsay finally finished his undergrad education. Sure, he was alone in a warehouse full of toilets. But he was only in that position due to his ability to utilize his skill set to create an inventory system that benefited the company. Then he tried to build a new system at the paving stone company to help streamline his job there. Yes, that blew up in his face, but at least he was trying to put that skill set to use To err is human, and we all make mistakes. What matters is that Lindsay didn't let that event become some crushing defeat that stopped him from building systems in the future. He went on to work at Southern Methodist University, and got his MBA and mentioned system building as something he enjoyed and got to utilize in each of those experiences. That brings us full circle back to podcasting. Think about how different all those rules were. Despite that, he was able to use a skill set that he enjoys using, which proves to me that you're never stuck in one career. You always have a marketable skill set that you can use to pivot to something else entirely. You just need to recognize what that skill set is. Lesson number two, is that your career isn't a sprint. Sometimes you'll find yourself just drifting along doing something for no particularly strong reason. Some jobs are just jobs, the comfortable ways to put food on the table and support your hobbies. Other times, you'll be struck by some kind of inspiration, and you'll make the right moves and opportunities will open up in front of you. As Lindsay said right near the end of our conversation, in his case, when it mattered, he took advantage of those opportunities. This point is illustrated when Lindsay finished his MBA, he spoke to his manager about his new skill set. And suddenly, he had a fancy new title, a new pay grade and a pretty sweet outlook on life. But for me, the more interesting moment that demonstrates this point is when he was first fired from the insurance company, he identified that this was a chance to have a real shot at having a career in audio, something that up to this point had just been a hobby that paid for itself. So he co founded an audio book company, which led to the creation of terms his first major podcast. that led to Wondery. Wondery led to American History Tellers, and the joy of working on that lead Lindsay to create American Scandal. And that's the gateway to the present, where 25 years into the workforce. It sounds like Lindsay is the happiest he's ever been. So if you're trying to find that thing that will make you happy. Keep an eye open for when opportunity presents itself and make sure you take advantage of it. It might not pay off tomorrow, or next week or next year. But years from now, you might be able to look back and realize that one decision in a moment of inspiration led you to the career you love. And that is what I learned from Lindsay today. That's all for this episode of career crossroads. So now that we're wrapping up if you haven't already, I highly recommend checking out one of Lindsay's podcasts. I think it's pretty clear by now that American Scandal is a favorite of mine. So I recommend the episodes on the Exxon Valdez or the Hari Krishna murders. If you know someone who would be interested in Lindsay's career path, I hope that you will share this episode with them. And if you want to hear more interviews, go to career Crossroads podcast.com. If you like what you hear, you can sign up to our mailing list to get notified of new episodes every week. And follow us on social media and leave the podcast review. I'd really appreciate it. One last note about this interview, because Lindsay asked in the beginning. I'm ratting it a five out of five.