Jessi Sanfilippo: [00:00:00] How do I want to exist in the next role that I'm in? Right. What type of contribution and impact do I have and how do I establish that in a more concrete or emboldened way?

David Fano: Hey, everyone. Welcome to nonlinear a podcast about the decisions that shape our careers. I'm Dave fan and the founder and CEO of teal and the host of this show.

If you're enjoying the conversation on this episode, please make sure to subscribe, share, and rate us wherever you're listening to the show. It really helps shine a light on these amazing careers and increases the chances of us learning from each other. Again, thank you so much. And let's jump into this amazing career.

Hey, everyone. Thanks for joining. I'm super excited for today's conversation. I've been a longtime fan boy of today's guests on Twitter and seeing all the funny, amazing content she puts out occasionally serious, but just all around. [00:01:00] Good stuff. I learned a lot. Today's guest is Jess Sanfilippo and I just can't wait to hear all about her career, but rather than giving some sort of short summary, I'd rather just, you tell us a little bit about your.

Jessi Sanfilippo: Oh, my gosh. Well, I'm so excited also. Thank you for calling me funny, but my one goal in life is to be like, am I funny? And sometimes serious. Perfect. Yeah. So I am a career marketer in terms of what I do for work, but beyond that, I'm just sort of. A lover of life, I guess we'll get real woo right out of the gate, you know, a lover of life and experiencing the world.

And so, you know, that for me, has driven, we're going to get into this lovely non-linear career of mine. And you'll kind of when you're along for the ride, kind of understand how it all kind of melds and flows and all that sort of stuff. Welcome to the woo episode with me. I

David Fano: love it. I love it. I feel like we need more woo in our [00:02:00] lives.

Okay. So we always like to kick it off with the same question, which is when. In your life. This sounds very heavy, but let's not think about it that way. Did you first start to think of your career more intentionally? And what I mean by that is like you were thinking like I'm going to do this thing. And that thing is going to be the thing that put food that puts food on my table.

It could've been as early as childhood selling lemonades, you know, or later in life with. It's going to be what I retire with, but when did you start to think that I could see myself doing this?

Jessi Sanfilippo: Yeah. So it's really funny because it, it didn't pan out, but it became a very parallel career, but let's, we'll take it all the way back to sixth grade.

Nice, huge boy band fan, right? Like lover of music, love music, huge boy band fan. And around that time was when Lou Pearlman for anyone listening. He created the Backstreet boys who you created the instinct, like the boy [00:03:00] band machine, right. Sort of modern for the millennials in the crowd. And he did not leave a legacy of honest entrepreneurship if you will.

And I was, you know, 12 years old and somehow that got me up in arms and I was like, I am going to protect the boy bands. I'm going to become an entertainment lawyer. This is going to be. Like no one will ever experience this again. Right? Like very fan girl dramatic. And then I quickly realized that that amount of, you know, sophisticated education was not going to be, for me, it didn't quite fit my personality type.

So I didn't and up, you know, on the law and legal side of things, but I did. And my first like intentional job out of high school was. And radio. So it was, and I was programming and. What does the word programming and promoting? I was doing pretty much all of [00:04:00] the three PS of radio. And I was like, okay, I did it.

I'm here. I got there, I got there, I got to this place. And then, you know, pretty a few years after that I got pregnant with a baby. And so, you know, I had my son, I went back for a little bit. His dad also was in radio and. I was like, you know what? I just don't know if I'm going to raise a baby in rock and roll.

You know what I mean? And it was really, really like a pretty taxing, you know, demand shows all the time. You're the one that's losing, you know, to get their records on the radio and stuff like that. So just a lot of need for, you know, me to be present and me to be. Persuaded and things like that. And I was, you know, really, really fortuitous and my privilege that I could make the choice to go stay home and, you know, [00:05:00] Put the mom hat take, you know, take the rocker hat off, put the mom hat on and you know, and spend those really early formative years with, you know, at home with my son.

So, but that was, yeah, I would take it back to the question because hello, I'm a tangent, I'm walking as you know, I'm just like tangents and a trench coat. I'm not really a woman. So, yeah, that, that was the first like intentional like career, like interest I had was way back in sixth grade and the comeuppance of boyfriend.

David Fano: Well, I'm sure. Well, it'll come full circle when we talk about what you're doing now, but talk to us a little bit about that decision to take a break. Cause I think, you know, one of the things we try to do on the show is dive into these internal struggles that folks have. And oftentimes it's not. Logical.

Right. Uh, and that's the thing I think about careers is very, very hard is that there's these just like tensions and pressures in the air, these like [00:06:00] weird taboos that you're just like not supposed to do that. There's the pressure of like, well, I mean, if I'm a woman taking it off, taking time off, and then what does that mean for the next woman?

And I'm, I'm trying to be a role model. And it's like all these things that are just like so hard that I talked to my wife about. Um, obviously I can't relate given that I'm sort of at the top of the privilege period. But yeah. Talk to us through that, you know, like this idea of say, you know what? I got my career, I got to where I wanted to go, but I'm going to take a break.

Did you think about like, how did it at a time horizon? How did you give yourself the permission to do it? Yeah,

Jessi Sanfilippo: I've done departures for personal reasons. Multiple times throughout my career. Right. I've been in the adult workforce, if you will, you know, for almost 20 years now and you know, there've been multiple.

Points, whether by forcing function or just by, you know, voluntary decision to take a step away to, you know, fill the personal [00:07:00] canteen. Right. As opposed to just living to work. Right. I really kind of flip it on to like, you know, oh, I work to live as opposed to I live to work. And I know that in my experience, so many of those times when I would step away, it was really, really hard at first.

So like, I'm not going to sit here and sugar coat it and be like, oh yeah, it was an easy decision. And there wasn't turmoil and there wasn't, you know, guilt and shame. And you know, like you mentioned before, What sort of example, or, you know, the, could I be setting for the next generation of women coming through who might have, you know, come up to this decision and how.

You know, is it contributing to that tumultuous energy or is it actually benefiting and setting a better stage and ultimately over time and maturity and things like that, I'm like, oh, this is a stage setter, as opposed to, you know, [00:08:00] just like a throw him in the deep end type of example, I'm leaving, but it took time.

You know, it took time when I in. I wouldn't even say it's a honeymoon. Cause it was pretty nightmarish, right? That like, I guess the honeymoon considered a phase of time really soon after a departure where you're just like, oh my gosh, you're second guessing yourself to make the right decision. And I think that it's natural to go through that.

No matter the circumstances of a departure, whether you're fired, you know, obviously they're going to be a sliding scale of. The negative side of it, but you know, whether you were fired or as voluntary, or it was like a collaborative exit. There's that spot where you just like question it completely. And then, you know, for me working through the questioning and not allowing myself to sit into retrospect too much, I [00:09:00] think that there's always phenomenal, phenomenal takeaways.

Like I have zero regrets for any role that I've had. And then whether that's in-house, you know, as a freelancer, whatever it's been, I've never regretted the work I did while I was there, because the only reason I had those jobs and was contributing and woke up and passionate and motivated because I love the work I was doing.

Right. It was so neutered from. Any, you know, bureaucracy or politics or whatever that could exist in an organization. And I've, I've run the gamut. I've been in corporate. I've been in startups. I've been in toxic. I've been in healthy. Like it's all, I've been in the full bag. I was like, everybody's coming to the party and we're going to figure this out.

And so. The one thing that I guess would fall into like the permissible category was like knowing when I came up to that decision again in the future that, you know, the next time, the next time that I was like, [00:10:00] it's gonna suck at first. But after you get through the part that sucks, you're going to be really proud of what you did when you were there.

You know?

David Fano: So yeah, someone once told me, uh, his name is Tommy Dyer. I was like to give credit to the smart people that told me things. You can probably only understand career fulfillment in retrospect, because this place that you feel the best about probably sucked at the time.

Jessi Sanfilippo: Oh, I mean, absolutely. There are, you know, so many stories of, you know, when I was like, I want to scream and just like stand in a field alone and scream.

This is so hard. Sometimes that felt unnecessarily hard sometimes. The luck of the situation, you know, like it just calls because this is tough. And I look back on those and I'm just like, hell yeah, you did that. Like, that was amazing. But yeah, I'm like sobbing to my team and just stressed and you know, but you're like, [00:11:00] hyper-focused, you're in it.

You're like putting in, you know, never, literally the. Thank God. I work at a computer. You know, if there's blood, there's a problem, but you know, the sweat and the tears for sure. You know, a pretty consistent through line for me.

David Fano: All right. So you took, we shouldn't even call it a pause or a break, uh, cause honestly, watching over a kid.

So much harder than being at a computer,

Jessi Sanfilippo: you don't

David Fano: say so you decided to take a break and go back to work. And what, what was that process like? When did you sort of say, okay, now's the time for me to. Jump back to what I was doing. And then even like, you know, what is that right. Getting a moment to take a breather from work, you'd get a chance to reevaluate.

And so w how did you sort of like reenter the workforce? Yeah,

Jessi Sanfilippo: so it was really kind of interesting because I'm, I'm such a, like going back to, you know, sort of my clunky intro of myself, [00:12:00] I'm a super immersive person. I'm like, I. Such like a staunch supporter of your present you're in the moment. Like you just really, really immerse yourself in that time.

You're not looking too far ahead, not looking too far backward. And my line of work before I was home with my son was really, really creative, super creative. I was helping my on-air staff, you know, figure out funds, segments, and. Countdown shows and you prepping for interviews and trying to make them more fun than the standard issue.

So what inspired you to write the song? You know, like all that sort of thing for when talent came through and you know, one of the biggest things I did before I left was I. Produced a radio festival, right. It was a big festival that we did for two days out in Phoenix. And we had a lot of, it was kind of the outset or like the beginning of social media.

Right. So it was like early two thousands. I remember getting my honors staff, all the jocks, a Twitter account, [00:13:00] like it was like very, very new and wild west and just fit because it was the Southwest anyway. So we had the opportunity to have a lot of fun with it. Interactive activations, which was something we weren't really, we didn't really do that.

You know, it was kind of like, oh, this is fun. Someone will capture it and maybe put it in a scrapbook or a shadow box with their ticket or whatever it was. And we had this chance as social networks and stuff started to build up and, and kind of get a footing to have more interactivity with the fans and the artists and the station and all that sort of stuff.

That was the last thing I did. And that's a hyper creative thing to be like, Ooh, it's new, it's exciting. It's fun. Like we get to, you know, we get to kind of pioneer something here potentially. So when you're home with a baby of anyone who doesn't know, they sleep Eaton. That's all they do. They cry sometimes.

And then it's usually because [00:14:00] they need to sleep, eat or poop. And so it's really not the most creative outlet, you know, to in those really early days. And, and honestly, keep the baby alive, keep your sanity, you know, um, do the best you can with what you have and just make it to the end of the day and then make it to tomorrow is like a very minute by minute experience in that early childhood stage.

So. My son is actually very independent. So by about one and a half, he was just like, I would literally ask me to play alone. And I was like, okay. So I would just be like, you know, in the hallway, like peeking into his room being like, could I be a part of that? You know? And that, that was kind of a moment for me where I was.

Okay. Obviously, I'm going to be really, really a big part of this imaginative stage, right? That's kind of where they're starting to learn things and explore things. And, you know, in a way that there's an element [00:15:00] of more finite communication. I mean, obviously an 18 month old as well. Fluent vocabulary, but, you know, I was like, okay, we're coming up on this phase where there's hyper, hyper imaginative.

It could be hyper, hyper creative. And I did what a lot of moms with kids around the same age did back in 2008, which is I started a mom blog. So we had families spread out all across the country and I was like, You know, I'm kind of a super into tech. So it was like, oh, I bet I could build, you know, a blog or whatever blog spot rip.

Like that's where, you know, I posted my first blog and, you know, just really built a community. And I was like, okay, I have this like creative outlet that like, this is really cool. So I did that when he was pretty young and was like, oh, I can just kind of be creative. Like it doesn't have to contribute necessarily to a company [00:16:00] or an organization or anything like that.

Right now I can just sort of channel what I'm experiencing with my kid storytell to, to build that, you know, the modern day village and. Then I was like, okay, it's great to talk about my kid. But now as he got older and I had, you know, less of like, you know, poof, all that kind of phase of things, I was like, okay, well, who am I?

Who am I? What, you know, what, what are the things that I have like, Drawn interest too, because as much as I love to write about how cool this car seat is, I would also like to write about things that, you know, that, that interests me. So the natural progression for me, it was pop culture, right? So I went straight to music, TV movies, never got into the celebrity gossip thing to you.

T goodness, because that is a slippery slope. That I'm glad that I did not slide down, but yeah, just kind [00:17:00] of, you know, experiencing and sharing and, you know, bringing some of those skills that I had when I was. Literally determining what the rotation would be on the radio station into, well, now I can curate playlist and recommend new music because that was what I lived and breathed, you know, 10 plus hours a day when I was working in radio.

So I was like, ah, we just, we're just dusting this off. We're hopping back on the bike and we're going. So that was really. What like the first step. And then I figured why could be creative for other people, I guess. And so I create, I developed a creative agency and, you know, just kind of helps small businesses.

Really build out what their identity was, build out what, you know, basically guarding the loss kittens, the long and short of it. I mean, everyone from real estate agents to, you know, venues locally and stuff [00:18:00] like that. So it was, it was, I ran the gamut in terms of clientele, but it was, it was fun because everything was a new creative thing.

David Fano: Well, that was cool. It was good. Going from that do use that time as an opportunity to grow personally, grow professionally and find these outlets because I think that's one of the things, again, I just, I have the sort of the passenger seat from watching my wife go through the process. And in that, that process of like, how do you identify, what's your role?

What do you do? And just really hard. I don't think anything that like any, any man could empathize. But yeah, it's a tricky process, so amazing that you sort of are doing what you're doing now, you know, and navigating that and learning through that process. So when that season's ending and you're thinking about the next thing you start the agency, where did that take you where the next kind of career moment?

Jessi Sanfilippo: Yeah, I think that the, you know, going back to my [00:19:00] fascination with tech, I learned really quickly that I was not familiar with the world of sales. I wasn't. I had no idea about it, or I was like pop culture, girl. Right. So I was like, oh, this is really interesting. I mean, I grew up with a personal computer in my bedroom when the personal computers were like the size of a mini fridge.

So like my dad instilled in me really, really early. He worked in telecom forever, just a fascination with technology. And so. You know, blogging really kind of introduced me to obviously some SAS products, not knowing at the time that there was a whole industry of this. And I started to pursue, because I'm such a, such a student of the world, right.

I'm super studious and curious, and I just. If something interests me, I'm like, don't even try to talk to me. I'm going, I'm full steam. I want a bullet train to knowledge. Like no one stopped [00:20:00] me. And I just started to acquire, you know, SAS and SAS clients to learn more about it. I was like, okay, well what's like, what is a product?

If it's not a physical product? And you know, just really, really dive deep into that. And it put me on a path to become connected. Saster, which is one of the biggest communities for SAS, founders and investors, and, you know, participants of the industry. And they brought me on as their senior event marketing manager.

So their big thing was, you know, that these annual events and ancillary events, and I was like, Super into the data and love people. Right? It's like I describe, cause I've had this conversation about like linear, non linear with a few, you know, colleagues and friends and stuff. And I'm like, I like to think the shape of my trail or journey as like a flower, like it [00:21:00] always goes out and comes back in.

Like there's always a central point. Right. And the central point has always been. Humans people. Right? Because literally, no matter what industry or type of work you're doing, we're all people at the end of the day. Right. And whether you're communicating with a business owner, you're communicating with, you know, a product customer, you know, like a physical product.

I don't know, jewelry or something it's people. Right. And so at a really base level, I think that there are so many soft skills that are like that in that that create, or I guess yeah. Creates that's a word, right. We're using words, you know, that create that. Core center, like pollination station, which is, you know, empathy and curiosity, things that no one [00:22:00] would ever look at a resume and be like, is that a skill?

Or do you know, Excel? You know? So I was like, that was really cool to me. And then, and I was like, this. I like people. Right? So, um, that role in particular was very, very involved in terms of logistics and like the behind the curtain magic. Right. And the big, big payoff was all. When the stage was set and, you know, the roster of speakers would hit the stage and attendees from all over the world would come in and like huge cohorts.

And, you know, just to really, again, like immerse themselves in what's the state of the industry. What are people building just like immerse themselves in the curiosity of what's going on. And so that was like the hell yeah. Moment, you know, [00:23:00] to like, to put it in. There's no other real terms like, oh yeah, hell yeah.

This is why we do what we do. This is why we build what we're building. And for me personally, I was like, this. Why I do what I do, right? So it's like, okay, this is cool. But like, this is really my, why it's like people coming together, immersing themselves in curiosity is such a driving force for me, that creating an experience that like replicates that internal, like soul polling thing is what really from that point kind of pulled me to, you know, everything that has led me into what I'm doing.

So

David Fano: that was your first exposure to event marketing.

Jessi Sanfilippo: Yeah, well, I mean, when I was doing the radio festival, I had to mark it that event, it was essentially like marketing a concert on steroids. Cause you got three stages and, you know, tons of artists that had very, you know, obviously it wasn't crazy.

Crossover was like a country [00:24:00] star and like a hip hop, you know, artists, but you know, you're, you're still battling for. Marketing a multitude of experiences at one time,

David Fano: it's something that's happening. Maybe it's always happened, but I've developed more of a kind of sensitivity to it, given that I'm trying to market certain things, but it's like one company's marketing is another company's product.

Yeah. And sometimes one company's product is another company's marketing. The same thing can be given away as marketing while another company's like trying to sell it. And we see that a lot. So in your case, the product. Was the concert, you know, and you were like putting on the concert, but then event based marketing or, you know, the conference for Saster, but the product was the community.

And that was kind of like one of the things. So, but the skills were probably let's call it 90% the

Jessi Sanfilippo: same. Oh yeah. Super suit. I mean, super transferable. Right. And that's been [00:25:00] right in the flower of my career, but like really the through left's the stem for me is. The transference of skills, right. It's and, you know, having it be more about my aptitude than my accolade, something I tell a lot of, you know, people that I mentor and stuff, I was like, don't worries that were yourself so much about the big flashy degree, the big, you know, award, you know, however, Whatever the, the thing, the, the badge of honor, you know, so to speak as, as you're so focused and wrapped up in, and just really like, be your super apt self and learn as much as you can to contribute in the best way that you can for what you want to do.

So it's

David Fano: the experiences at the end of the day and then how you package them, but what actually enables you to do the work as the experience. All right. So Saster super impactful. And for [00:26:00] anyone listening, who doesn't know what SAS is now that we've said it like 15 times, which is essentially a software subscription, it's a fancy way of saying that.

And now there's lots of. As a service. So, you know, platform as a service, you name it. We did space as a service that we were. Um, but it's a nice way to say subscription. So after your time at Saster then what kind of, you know, the moments of transition I think are where there's a lot of learning and stepping away.

Was it reactive? Was it proactive? But we talk about this career growth loop of searching, transitioning, developing, because once you search, you find it. Deal with, uh, I was here now. I'm there. Okay. I'm comfortable now. I'm developing. Okay. Starting to plateau. Let me search for that next thing again. So what was that kind of plateaued moment for you there in this new industry?

You know, transferable skills, but you know, extensively new and thinking about what was next.

Jessi Sanfilippo: Yeah, I mean, my departure was mostly [00:27:00] reactive and. That reactivity. Kick-started like a super introspective period for me, where I was like, okay, what is it that I'm really, really wanting to do? What am I wanting that?

Not, and not even, what am I wanting to do? I should take that back. How do I want to exist in the next role that I'm in? Right. What type of contribution and impact do I have? And. How do I establish that in a more concrete or emboldened way? Right? One of the things that I, I learned by no fault of anyone else at the organization was I had a tendency and this is what I learned, you know, in a fastened, dirty way for myself and, and about my career.

And my work style was that I play myself small. And I, I found myself, you know, in that ugly nightmare honeymoon, you know, a honeymoon where the [00:28:00] plane crashes type of situation phase after my departure, where I was like, oh crap. Okay. I did the retrospection and I was like, you played smaller here. And why, and why did you do that?

Right. For me, I consistently have had a therapist always, but they get extra from me after I leave a gig, you know, because I really want to understand the ownership and accountability of, you know, what, what it was that I contributed or my lack of contribution to. Put me in a position where a, I either had to make that choice or was considering that choice or B you know, I've been very fortunate that I've never been fired, but you know, what, what could I, and not like, oh, what could I have done?

You know, we, we, we can get lost in that trap for a really, really long time. Doing sort of that like 10,000 foot level, [00:29:00] like what did I not bring to the table? Or what did I bring too much of? Or what, how, how did I contribute to this? Right. Cause I think that any time anyone is making a departure from something that, you know, at one time or for the entire time, just like set them on fire, like in a good way.

No, Oh, no, my hair has gone like in a good, no offense,

David Fano: but I was listening. I

Jessi Sanfilippo: know it was just like, as it came out of my mouth, I was like, if only you had a hairball, the shove back in,

David Fano: I'm very proud of my

Jessi Sanfilippo: lack of, I was going to say Baldwin, beautiful, you know, but you know, what was it that, you know, shifted from that, like jumped out of bed in the morning.

Do this, like that, that passion, how, you know, to really look back, because if you don't look back at what started to make the flame kind of like Tinder a [00:30:00] little bit, or I guess the other. Cinder, I don't know, words, you know, I think that you, you can find yourself falling into the same trap of, you know, kind of conducting yourself the same way or, you know, doing the same thing, saying yes to the same things or saying no to the same things.

And you'll fall into this. Really gross cycle. And so for me, I'm like, I love a process. I love and understanding, but there are so many variables right along the way, their circumstances and personalities and things like that outside of yourself. On a team that will contribute to, you know, the, the ways that we make decisions about what we're contributing.

So that's like the big thing that in-between is really the meat for me, you know, because you know, I've experienced so many different [00:31:00] roles. Like I said, running the gamut that there's such a beauty to the in-between that I think that we. I mean, don't get me wrong. There's a lot of ugly to the in-between as well, you know, depending on your situation, but there's a lot of beauty because you're learning so many things about yourself.

Like we, we weren't born to work. We were born to live. Right. And so knowing that the work will always get done, but how are you living and how does that experience. Live in life impact the work that you show up to do. And I think that I know firsthand, the more time you spend being like rooted in yourself and what drives you outside of any consequence, right?

Good or bad of what you do. Obviously you're [00:32:00] striving for good consequence, but despite any consequence of how you live. It fuels such a different energy to the work that you do. Like I would be content for the rest of my life. I mean, this is not my plan, but I would be contend for the rest of my life. If things pan down away where I sat in the back of an empty warehouse and did data entry all day, I would be, feel like the queen of the world.

Right. Because I know that my experience of life and my love of life and what drives. To wake up and spend time with the people I spend time with and love the people that I love and meet the people I need and learn the things I learn has nothing to do with what I'm type the data I'm entreating into, you know, a system or a software.

So that's, I told you, we will, we were going away. We will. And we went there. I

David Fano: like it. I like it. Yeah. I mean, I think this idea of like [00:33:00] work-life balance and the way that we like. Those two words. I don't think like belong in the same, like construct, because work is a subset of life. Like there's life is like the, the apex thing, you know, and then there's all these like subsets to it.

And so when I'm working, I am like, And when I'm leaving, I'm working. So it's just, it's this bizarre thing that we've done because of the commercialization of the world and you where there's this 40 hour work week and last year. Yeah. It's, it's really unfortunate that it's kind of come this way, but a lot of these things, we just kind of do them.

You can't really even track back to like why they make sense today. But, you know, I was talking to someone yesterday, just, just I'll I'll participate in the tangent thing. Yeah. I said, do you know why we don't have more representatives? I'm like, why is cause there's only 500 and I can't even remember the number.

Let's call it 550 seats. So what do you do next?

Jessi Sanfilippo: What do I do next? So next I, well, I, I move forward by looking back, which is, I'm [00:34:00] very contrarian to everything I have said, but when I had sat on I'm very lightening in the bottle. Right. I think that that's, it's the spontaneity of what has made me a unique marketer has been that I don't, you know, again, going back to constructs or arbitrary, I'm great at time management, but I don't time block inspiration.

I don't, you know, that that's like, I don't have like my creative time. It's like, it happens when it happens. And I know that that's possible because of what I do when I'm not focused on those things. So like center in just like exist. And so it was seven years ago, so I'm like, woo, woo. Um, welcome to the S the Seesaw.

Um, so seven years ago I was sitting in my apartment in LA at the time son was in school and I was like, maybe I should do something in the music industry. What [00:35:00] could I do at this time? I was like, at the height of, you know, social media was really, really kind of picking up taking on this, this form of.

You know, uh, action, actually valid communication channel for, you know, brands and celebrities and human being, you know, just the everyday person, I guess everyone's celebrity in their own. Right. And I was like, I should do something. And I remember I was making a pop tart in my kitchen. It was, I was just waiting on that to pop out of the toaster.

And I was like, roadie, social. And so I did what any millennial who grew up on aim and MySpace did I did the full court press. I got the domain, I got the social handles and I sat on them because I was like, I don't know what this is, but I'm thinking of something and I'm, you know, uh, there's, there's something here.

I just don't know what it is. The only [00:36:00] time I really gave it any thought was every year when I would get the GoDaddy renewal, they were like, it's coming up and it's going to renew. And I was like, oh, that's right. I should, I should think about that. I should do something with this. So seven years later, I'm on a sabbatical and, you know, A little burnt out on a sabbatical, kind of like reconnecting with myself.

I make the mistake question mark, or the beautiful decision to go to a concert. And so I go to a concert and I'm like, oh man, I got really fortunate with where I was, you know, in the crowd, in the pit where I got to see, you know, the production crew. Doing their thing. Right. We have the soundboard for the opener was like right there.

And I was like, oh man. Okay. I remember like, you know, cause I was the backside of Maui when I was doing the radio festival stuff and I was driving the golf cart at six months pregnant, like [00:37:00] getting, you know, artists to, you know, interview stages and performance stages and stuff. And I was like, oh, dang it.

This is what I'm supposed to do with, with this account. Right. Not necessarily the production. I also met such incredible fans and I think the perfect storm byproduct of a pandemic and lies music, which has, I've always been something that I'm like, there is no thrill, like, you know, standing in a crowd, listening to either someone you love and artists you love or.

Open mic night at the local bar. Like it doesn't matter if, if there's live music there's there's, uh, electric energy. You know, met a lot of fans and got to know some of the crew on that tour. And I was just like, man, this is something I got to do. And I got to, I talked to my founder at the time and I was like, I need to spend some time [00:38:00] Lena, like thinking about this and deciding can I do.

Should I focus on one or the, you know, one or the other, and, you know, ultimately came to the decision. This, this needs me, you know, this needs my full attention to be what I feel like it can be. And so I didn't have offerings quite yet. I was like, I still don't exactly know. Cause I mean, I've been out of the music industry for 15 years and I love China shops, but I don't like to be a bull in one, you know, I'm like, I want to come and admire the China and maybe if my tail flicks something that I see and I'm like that could use some fixing or changing or woopsies, I've got some glue if you need it.

So. I committed to going to a industry event that had all of the key players, um, you know, from artist managers to booking agents, to venue owners and, and I, and promoters. And I just went to be a [00:39:00] fly on the wall. I had nothing to offer in terms of, I wasn't going to network with. Something to offer. I was going to network to understand, you know, where are they now?

What are the, what are the pain points or shortcomings that they're really seeking some sort of solution for? And the most interesting takeaway for me was that artist's brand development with, you know, the advent and prominence of social media and the internet is a true rocket ship compared to, you know, the band.

Seventies eighties, you know, like even 10, 15 years, the, the amount of demand for artists. And especially, I should say that this was specific to the touring industry. This event I went to it's crazy because a, you know, an artist that may have emerged two years ago had a viral Tik TOK song. You know, a little clip on, on [00:40:00] Tik TOK could easily fill an arena.

But that artist has never really done a tour, so you're not going to grow. I mean, that is like, you know, reckless and dangerous to throw like a new emerging artist into an arena setting, you know, and, and have them be equipped to meet that moment. So what it really is. Shined a really huge spotlight on for artists managers and artists teams is the fans do not give a flying Cahoot.

If a label makes an announcement about an artist, you know, or even their management team or their PR team makes an announcement, but it doesn't come from the artists. There's a, there's a trust and confidence relationship that didn't really exist, you know, prior to. 2019, you know, fans would take the information from anywhere and you know, now with like everyone's stuck at [00:41:00] home and that's how they felt connected.

They couldn't go to a show for years, which is, you know, kind of what would say she ate that like I'm connected to them, you know? And so I kind of shifted to this digital experience and connection, and we don't really know how to capture. That fan artist relationship in a way that's meaningful, but we know that something is there.

Right? And so that, that was how I started to, um, craft what my offering would be. I literally threw up a website the second day of the conference in my hotel room. Cause I was like, oh crap. Because people are starting to ask you the questions and stuff, which. Hindsight 2020, obviously that was going to be a situation that came up.

But I was just like, just my charm, I guess, and we'll connect later, but then they, you know, they wanted to know more. So it was like, okay, let's dump your ideas into a one page website. So you have [00:42:00] something to, to show for yourself. Ma'am but you know, so, so I was like, this is how to. You know, bridge that gap.

And I like to say nourish and flourish, that existing relationship, any major artists that you see on tour. And I see this trickling into, you know, smaller acts and things like that, local venues and stuff. There's, without a doubt, there's entire fan accounts of, oh, I'm live streaming from where I'm sitting in the arena or the theater or a stadium.

And, you know, they're sitting there and they're granting access to. Tens of thousands. I think there was one livestream of just somebody. She was in like the fourth row in the pit at something that had like 80,000 viewers consistently the whole time, just on Instagram live. Right. And I'm like, there's something here that, that hasn't quite been captured yet from the business side of things.

And, [00:43:00] you know, not to solely or kind of. Tarnish that, you know, special thing, but I think there's a really, really organic and natural way for, you know, that relation to ship to become more official. Right. And have the artist be more connected and involved in that or their team. And so. I'm looking at that.

And then I'm looking at, well, how do we actualize that with new technology? And so that's the part of it. That's in like active development for me, like going on the road and like being like road mom, and everybody's having a good time, like make sure everyone has their orange slices, like fan front of house, back of house.

That's like right now, what the thing is. Th the service that I'm really providing the most, but actively working on, you know, blockchain bill ticketing, which unlocks a utility completely untapped for the everyday concert goer. You know, I know Coachella is doing. Yeah, [00:44:00] they're NFTs and stuff like that, but you know, it's still, there's still a major divide between the consumer that can afford and participate in that experience.

And, you know, somebody that's like, this is the one and only time I'm going to Coachella, the benefits could be. Experienced well beyond the event itself or for a long time to come with the technology, we're kind of exploring right now. That

David Fano: is super cool. I'll often say as the employee is becoming the enterprise and, you know, I think with.

Yeah, athletes and major celebrities. This was always the case. They had agents, they had business managers. Um, but now with everyone being able to be a creator and establish a brand and the scale of it it's different, but they can still have quite a bit of impact. And, you know, that's some of what we're trying to do at teal for everyday professional, but it makes so much sense with the success that some of these creators are having to.

You have to have some business infrastructure to help them navigate what is a very complex world, especially in terms of like talent and rights [00:45:00] and all those kinds of crazy things. So that sounds super cool. It sounds like a great intersection of all the skills and experiences you've built up over your career.

Jessi Sanfilippo: Yeah, I was, and I think it's funny and really kind of cool coming full circle to now I'm back in music, I'm back, you know, Really sitting in that pollination stage where I'm like, I'm curious, I'm immersed, I'm empathetic. Like I'm connecting with people, um, and music and, and how that connects to their lives and being like, I learned a lot of things that really I know are foundational for the success that this will, you know, ultimately achieve.

David Fano: So. Well, that sounds awesome. Good luck. We're excited to see where you take it. You have so much cool stuff and so many interesting ways for people to follow along with you. How can people tune in to the latest and greatest of just Sanfilippo?

Jessi Sanfilippo: Yeah, so, I mean, I'm Twitters, Twitter's my bed. It's been on Twitter for [00:46:00] a really long time, 13 years.

And so at I didn't swear at U S H U G G I L I PPO it'll be spelled in, spelled out in the show notes. I'm sure that's where my main situation takes place. Um, I have a personal website, Jesse sanfilippo.com that, um, I do a weekly newsletter that comes. Encompasses all things. I'm all pies. I'm sticking my thumb in, um, any given time and then roadie social I'm on Twitter and Instagram.

Ready social.com. So those are my that's where you can find me folk.

David Fano: Awesome. Well, we will link in the show notes, wherever you're listening or watching. Just this was awesome. I love the woo. I love the roundabouts. I love the tangents and a trench coat. This was awesome. Thank you so much for spending the time with us.

Oh

Jessi Sanfilippo: my gosh. Thank you for having me.

David Fano: And that's it for this episode of nonlinear. If you enjoyed today's conversation, make sure to [00:47:00] subscribe, share, and rate us wherever you're listening to the show, you can learn more about teal on our website, teal hq.com. That's teal like the color T E a L H q.com. Or follow us on social.

At teal underscore HQ. Thank you so much for joining us. And please tune back in to keep hearing about how we make the decisions that shape our career. The teal career paths podcast is produced by rainbow creative with senior producer, Matthew Jones and editor and associate producer drew McDowall. You can find more information on them at rainbow creative dot C O.

Thanks again. We'll see you next time.