Phillip K. Naithram: well, Jess Szmajda welcome. Thank you for joining us here at the DC local leader’s podcast.
Jess Szmajda: for having me.
Phillip K. Naithram: So, you are currently general manager of the VPN services with AWS, if we didn’t already know. You’ve got a great career before that you were a CTO at Axios. And before that you co-founded a company. What talk to us about Uptoro and how old were you when you co-founded that company?
Jess Szmajda: I was 30.
Phillip K. Naithram: so relatively young, right? Not, not too far outside of school.
Jess Szmajda: I guess not. Well, I mean, honestly, I had an interesting kind of path. I got kicked out of school. I Did
Phillip K. Naithram: get for you? So, let’s hear this story.
Jess Szmajda: Well, I was at college park attending CS. It was actually doubling in music composition. And., I don’t know, I just never went to Class. I had taught myself how to program when I was a kid. So, I don’t know, we had a computer and well, okay. So, do you want the whole story? We had a computer, like an old 2 86 in the mid-eighties and my dad was a letter carrier. My mom had like, an in-home daycare. we didn’t have a ton of money, but they blew it on buying this computer. And I was like, great, black screen. What do I do? Cause it was. And so, we got these magazines. 3, 2, 1 contact magazine, and in the back, they listed out a basic program, you could type it in you get a video game. And I was like, great. I’ll get a video game. The computer is right next to the air conditioner A growing up in Maryland the summers are really hot, It’s nasty. all the time. I want to sit next to the computer. And so, I’m figuring this thing out and I get a video game out of it. And so that’s how I learned to program was, basically like entertaining myself in a lot of ways. Six
Phillip K. Naithram: You were about six. Wow. Was your, is your parents is wondering why did you have this magazine in the house?
Jess Szmajda: Well, my parents were always into sort of stem. education, I suppose. My mom Was an early childhood educator. And my dad was just always fascinated by technology. And so, He brought technology into the house. He was always fascinated by it. So, I think I grew like, learned that from him. He helped me kind of get over a lot of the early humps. So, I started teaching him later
Phillip K. Naithram: What were you, what were your dinnertime conversations and stuff like that around like, were they
Jess Szmajda: Well, we didn’t talk about technology, I suppose around the dinner table so much? It was more just like. oh, that was Jess and her weird thing.
Phillip K. Naithram: Did you did you play sports or do anything when you were growing up?
Jess Szmajda: I mean, I was pretty bad, at sports, I guess I played like T-ball and, a little bit of baseball, but
Phillip K. Naithram: but music is part of your, like, did you pick that up as a, were you playing in the
Jess Szmajda: well, it was I was enrolled in piano lessons when I was three, I guess.
So that was like a big thing. thanks to my grandparents. So, music’s always been a huge part of my life. And I think when people say that there’s a connection between music and technology, And math. Cause you think about things in that sort of very ordered and S systems kind of Structured way. I suppose. So that’s always been a connection.
Phillip K. Naithram: What instruments did you play?
Jess Szmajda: Oh, I grew up playing piano and saxophone, but then in high school I picked up as soon and flute and I was the principal bassoonist for the DC youth orchestra in high school, I went to Suitland high school, which is a special performing arts school. And so, I played at Wolf trap, I played with the Kennedy center. I did like jazz and classical. music. And actually my, my super power today is I can play any instrument. you hand me.
Phillip K. Naithram: Really? Well, because you know, bass, bass, clef, and treble clef, it
Jess Szmajda: yeah, yeah.
Phillip K. Naithram: you, read
Jess Szmajda: my sisters had, like my sister had a violin and one of them had an oboe, and so I kind of picked up all these different kinds of things. and just ended up playing a lot of
Phillip K. Naithram: How many sisters do you have?
Jess Szmajda: too. I’m the oldest.
Phillip K. Naithram: You’re the oldest of two. And are they tech-related folks too? Did they follow a similar path?
Jess Szmajda: No. So, the middle sister? She’s. a kindergarten teacher near Baltimore and my youngest sister actually works in the cannabis industry in college.
Phillip K. Naithram: but I don’t know. They still play music now
Jess Szmajda: They’re not the musical kinds of than I am.
Phillip K. Naithram: that’s interesting. A lot of people that we’ve spoke to there’s always these overlaps between some sort of discipline. A lot of times it’s sports, sometimes it’s martial arts or, and, and sports. It’s not always team sports. I found it sometimes it’s the individual sports like swimming or track. That takes a lot of discipline to learn how to play
Jess Szmajda: Well, I mean, those have been a part of my life more and more in my adult years. Like I studied Taekwondo as an adult. Almost got to the black belt, but cop is with Uptoro actually,
Phillip K. Naithram: really? So, you, so you didn’t finish school. What were you doing in, but then you started up to around 30? So, you got to get, what were you doing during that time?
Jess Szmajda: Yeah, well when I dropped out of college, I was actually working, I ran it for a local gas company back in the nineties. GIS trans the did a bunch of consulting for the FAA. Actually, it was pretty fun. So
Phillip K. Naithram: Did you get certifications in coding or any of these things? So, you just, you knew you knew how to code and in what language, because you learned on dos, but then what
Jess Szmajda: Well, I mean, I, I guess I learned basic and then see an assembly. Cause I was interested in this thing happening in New York called the demo scene, which is about like making art and graphics out of with computers, which is really exciting. So, I learned C and assembly from that sort of taught myself. Pearl and bash programming. And That’s what I was doing when I left as trans, I went to. What was known as intermediate, but more than people know it as did, which was a local, large ISP in Maryland connected a lot of businesses together in the early days. And so, I was a hilarious administrator there and the basically to be good at your job, you have. to code. And so, I taught myself Pearl, I saw myself. Bash coding and then After I left did jacks in like, was this 2000 or So I moved up to Western Massachusetts for whole personal story reasons to follow somebody and ended up doing a lot of independent web consulting. So, it was PHP. And then I connected with a bunch of other consultants and got into Java a lot because we were doing well, that was just what the guy was using honestly. And I was like, yeah. I’ll learn Java.
Phillip K. Naithram: So, you’re just kind of freelancing at this time,
Jess Szmajda: Yeah, well, I w I freelanced for about a year or two in the early two thousand. This was right at the, big, first.com bubble crash
Phillip K. Naithram: So, I’m putting together a timeline. That’s right. And that’s, and that’s actually right around, like after nine 11
Jess Szmajda: well yeah, actually it was, I remember when nine 11. happened, I was at the detects office. It was sitting in, in cube farm, and somebody wheeled over a TV It was like everybody waiting to look at this thing. And I was like, what? And it was just stunning. What was happening? It was. Absolutely mind
Phillip K. Naithram: and when you think about the federal services and how that’s changed, like the creation of DHS and what was going on with, and the need for new technologies to come on board that’s right around all of that, that same time.
Jess Szmajda: Yeah. That’s a good point.
Phillip K. Naithram: when you were you’re teaching yourself how to code, what does that mean? Like you’re going home and doing.
Jess Szmajda: Well, I don’t know. I’ve just always been interested in technology, I suppose,
Phillip K. Naithram: but I mean like, what are you just practicing to try to make things happen
Jess Szmajda: like to teach myself Java? I remember specifically, I was like, I really want to learn how to do something graphical, like a video game. And so, I taught myself enough I think it was a. JWT at the time. I forget which I think it was framework It was, Java has got a bunch of them, but it gave me sort of a 2d canvas and I would paint, a grid of squares, like painted this little character and it moved around and I just kind of learned by looking it up in books or reading it on the internet, the resources had gotten a lot better over the years. Like I didn’t have
Phillip K. Naithram: Well, that’s what I was going to bring up too, is that, if you’re talking early two thousand, YouTube wasn’t
Jess Szmajda: no, yeah, I had to, I don’t know. I, I used to go on dial up modems to bulletin board systems in the eighties and I kind of got used to. digging through random. People’s like, scrawling’s on the wall to figure out how to make technology work.
Phillip K. Naithram: And you guys, you had a computer. I didn’t, my parents, we didn’t, well, we didn’t have a computer until I was, I was almost a senior in high school before we had our own computer. It was compact.
Jess Szmajda: Privilege, I think, to grow up so early with computer. Well, my dad was with the postal service. He was at the national headquarters over in L’Enfant and he was in the marketing department. And I think it was always curious about what the postal service could do. with technology, He was one of the early people, I think really pushing. for. Giving every citizen, an email address through the postal service and, that fell through, but it was an interesting sort of like connection of communication through technology.
And, and so like he would bring home communications devices Because I think he was really fascinated by that, so that’s how we got modems in the house really early as he was just borrowing it from work. And so that’s, I think how I had that kind of access., It’s interesting growing up around DC like this, a lot of people talk about like the federal government is such like a big entity and it can be like a faceless thing, but honestly, I think like, Being sort of the child. of someone who grew up in that. I mean, I think the government has an incredible way of providing access. in sort of an egalitarian way. Like I grew up without much money and yet I was able to get access.
to these kinds of things because my dad was able to like investigate those things through his work. I think it was really cool.
Phillip K. Naithram: That’s kind of, and it makes sense. I mean, email is electronic mail, so, your dad working for the post office, like you can see the connection there. So, so up to her. So, we never
Jess Szmajda: sure. Yeah. So, connecting the dots from the consulting company? And interestingly, I built a wireless ISP from scratch. when I was in Western Massachusetts. Anyway, or one of our biggest clients was testosterone nation. Biotest laboratories is the name of the company. Testosterone nation was their web brand. And so, I built that while I was a consultant with that group, they sell sports supplements.
It’s a bodybuilding magazine. Yeah. So, it’s like bodybuilding.com. If you know that one, this is like the, it’s like the grittier, like grungier competitor. to bodybuilding back. Yeah. So, it was an e-commerce system, web forums real-time chat. We did some interesting publishing kind of stuff was there for five years or so.
And then I ended up moving back to Maryland. And in like 2010, I met Adam and Toby Moore. who had the? They have this company where you could sell things on eBay, basically. And they realized that a bunch of businesses had stuff that they needed to say. on eBay. and they dug, they kind of follow that thread and found that these businesses had returned and excess and overstock goods that they weren’t able to handle very well. And so, they had this idea to build a technology platform, to enable retailers, to get more value out of those goods. And so, I met them. I met Adam first in 2010. And he talked about this idea and as someone with sort of the technology skills and abilities to, to build that and take that dream to reality. And so, I was like, yeah, great.
And so, I joined and I was the founding CTO and I was there until 2019 and we grew it to about 300 people by the time I left. And it’s more now, I think.
Phillip K. Naithram: What did that conversation kind of look like? It’s like, this is Did you, did you put in equity too? Or was
Jess Szmajda: I did not know. I didn’t have anything
Phillip K. Naithram: well, okay, but you had, well, you had the skill set, so you have the thing that they didn’t have, right. Because you can actually, they had the idea and you had the ability to build the thing that they had the idea
Jess Szmajda: yeah. They had a really strong prototype going like the whole, honestly, they were doing a whole bunch of things manually.
It was amazing what Adam built in Excel and visual basic. I will.
Phillip K. Naithram: That was going to be my next question, because nowadays we have like Adobe XD. We have so many resources where you can build like a platform kind of drag and drop almost. What did you use then? Like this is 2010,
Jess Szmajda: So yeah, the whole low-code no-code revolution hadn’t really hit yet.
Phillip K. Naithram: Yeah,
Jess Szmajda: no. So, Adam had built Adam was the COO and president. He had built a bunch of stuff in visual basic and Excel, and it was. pretty impressive What he was doing even connecting to third-party API services at the time, it wasn’t going to scale. And so, we had to rebuild everything. We use rebuild. We actually worked with a local,
contracting shop info ether which eventually got acquired to become the core of living social’s engineering team later. Yeah. So, we worked with those guys. It was like me and it was like three or four engineers from their group. And we built everything in Ruby on rails got it up, got it running. Eventually got a patent on it.
Phillip K. Naithram: All right. And so, and so what’s happening in 2019 to where you felt like you wanted to kind of,
Jess Szmajda: yeah, if he thinks that it happened the company, I think was going well I think this is actually, I need to talk about like my personal story I’m trans I’m transgender. And so, like in 2017 I came out and transitioned and, everybody, up Torah was super friendly and welcoming. and supportive. And I appreciated that, but I think there’s something about being a trans person, and like needing. sort of, a bright line in your life sometimes to like, because I don’t know, there’s something that is difficult to communicate to other trans people really, but to share it, like when people have seen for a very long time and not a tour, I’d been there seven years already as so, my old self. and they still saw me as my old self.
every day and every moment of every day. And I knew that, and this isn’t anything. against the people I’m working with. I love them. They’re still my great friends of mine. I work with some of them again now. But needing that kind of space to sort of re stablish yourself and, and sort of like be who you truly are in a different space. I think that’s something that I fundamentally realized. after a little while there., Uptoro, what’s going great It is going great. I’m still really proud of everything we built there, but I needed to change in my life. And so, I started looking for new opportunities and talk to various people at various times and eventually. I met Roy and Jim and Mike over at Axios, and that’s what led me to take that opportunity. And just like on a personal level again, like it was quickly night and day. Like I went to the second Axios annual party, which was really fun. And
Phillip K. Naithram: where was it?
Jess Szmajda: This was a, at a, at an event space downtown. I forget the name of it offhand, but it was I don’t know, just up from Logan Park.
Phillip K. Naithram: What, and what time is it like an annual like holiday
Jess Szmajda: well, this was, they were smart. They, they worked with a sponsor to like, do like a co-marketing event and also get a party out. So, this is, I think with Boeing, they were really helping drive Boeing’s like space-faring mission with. Influencers in, in the district. and so, this was sort of a party to connect that that vision and that mission to people who could make policy decisions and, and just sort of learn about what Boeing was doing. And so, we were also like, oh, hey, it’s also access to second year anniversary. So, whatever the list celebration. So, so yeah, that was, that was fun. But just meeting them like the women, like this is subtle thing where like, when. Men more physical space than, than women. And so, like the women were standing close to me and I was like, oh, I’m being accepted for who I am. People actually finally see me for who I am.
This is pretty amazing. So yeah, it was, it was a good thing for me personally. It was a strange thing; I think career wise. But it’s worked out really well, I think.
Phillip K. Naithram: It was funny as even as we get older, we’re still like, it’s still like seventh grade all over again. Like you walk into a room and the women are over there and the guys are over
Jess Szmajda: Oh, it totally is.
Phillip K. Naithram: Right.
Jess Szmajda: I think you notice this so much more when thing; like, gender is like this huge thing in your brain. and you kind of have to think about it so much. It’s like, yeah.
Phillip K. Naithram: Cause then it’s like, what side do I stand on? Sort
Jess Szmajda: Yeah. Oh Yeah. It’s like, oh, I’m supposed to be, no, I’m not supposed to be here. This feels wrong. It feels weird. Yeah. That’s interesting.
Phillip K. Naithram: What was it like over at Axios? Cause that’s a very different business. what was the learning curve like to learn that business? I mean, you were still CTL, so you were doing the thing you did really
Jess Szmajda: Yeah. So that’s why I joined Axios both to help drive them the media mission forward. but also more importantly, we had this vision of building a B2B software to help people communicate more effectively Axios, recognize that one of their big innovations in media was their ability to communicate. And so There Roy had this, I think beautiful idea of like, well, let’s try to bake them. Communication like fundamentals into machine learning into a big tech and help people communicate really effectively through that. And so, they were looking for somebody, with a technology sort of industry experience, not immediate experience so that they could help.
really create that kind of vision going forward. So, I happened to have media experience from, from testosterone nation. I also had like the technology experience through Uptoro and everything And so it was a good fit. So, learning the business, I mean the. media is wild. It’s, It’s very different. Like the men’s magazine I was with was nothing like, like, like big media, which is how access is. I mean, Like, I, some of the things that I did were around journalist’s protection, like making sure their devices were secure, making sure. Nobody could like pop their end points, they can actually do their reporting like that kind of security stuff. Just wasn’t an issue in the bodybuilding world.
Phillip K. Naithram: And you’re very, you’re nice. You’re only, you’re only in one, one vertical, which is bodybuilding and the things centered, centered around vertical.
Jess Szmajda: That’s right. that’s right. But Axios is, I mean, it’s politics for sure, but a whole bunch of other verticals too, and just making sure the whole publishing experience was easy people could do it from anywhere in the world. like from their phones. I think that was a really interesting set of challenges too. But then yeah. getting into the B2B space was, was another whole thing.
Phillip K. Naithram: Yeah. What was so you’re they it sounds like you’re like a lot of people you were technical in your skill set, but then you had to learn, soft skills or sales. And, and what was that process like? Did you have mentors that helped you? I know you’re a part of a group with, that’s how we met with some other, other folks. I mean, where did all that come into play what, what impact was that making on you as you go through all of the things you’re doing personally and professionally.
Jess Szmajda: I learned a lot of this Optoro like I, it Optoro being a, co-founder being the CTO there. I had to interact with the board. I interact with interact with the venture capitalists. I had to interact with our sales team I had to go out and talk to customers. And, I’d done some of that in my consulting days. And in various ways through that, but it was not. In the way that I did it up Torah. But also, after a while we brought in this executive coach. for the leadership team and she was Fantastic. And I just can’t say enough. Wonderful. things about executive coaching writ large especially like this was Amy poser. She’s now head of people actually I think she’s the COO over at there were, we were competitor and I forget their name so she was Fantastic. she helped I think all of us work through some rough edge being kids effectively starting a company, but with me, she and I
Phillip K. Naithram: was, she was brought in to do what, like seminars or meet with you
Jess Szmajda: one-on-one yeah this is one-on-one coaching with
Phillip K. Naithram: just the C-suite or everyone.
Jess Szmajda: It was pretty much just the C-suite. I think we added some more people over time.
Phillip K. Naithram: Right. And so, and was this once a week, once a month.
Jess Szmajda: Once a month. Yeah, a, about an hour-long session each. And we started by doing this thing called the leadership circle assessment. I don’t know, two or 400 question survey, that you have to like make 15 different people answer. And like, it’s
Phillip K. Naithram: like a 360
Jess Szmajda: a 365.
Phillip K. Naithram: What impact do I make? They give you opinions, hopefully raw opinions
Jess Szmajda: Well, yeah. And that’s the thing is like you get. 360 pictures of like how people see you. And that’s the trick is that it’s not who you are. It’s how people see you.
Phillip K. Naithram: Yeah. It’s not who you want to be or what you think or what you hope they see you as it’s what they actually see you
Jess Szmajda: exactly and that’s the thing that was really revolutionary for me, because I was like, oh, well, this, brilliant technologist. and I know what I’m doing. And it’s wonderful, no. people saw me as a jerk
Phillip K. Naithram: really? What’s that was that a, is that a real life like
Jess Szmajda: Yeah. W I think the, the input I got was that I looked. I don’t take things seriously I look better. I’m full of myself. I look like I don’t care about people. and I’m like, this is not me. I love people. I care deeply about everybody. at work with like, this is, and so it was a real eye opener. And so, we get to look at, well, this is the feedback you’re getting. This Isn’t how people see. you. You should probably change.
Phillip K. Naithram: So, would you do with that feeling? I mean, that’s got to be vulnerable and
Jess Szmajda: It was tough
Phillip K. Naithram: a shame in there,
Jess Szmajda: Yeah. Yeah, no, I was, I was, I had a hard time and frankly, every time because we did this Assessment a few times. And every time I was like, wow, I’m just so disappointed in myself. And I’m So, this is bad.
Phillip K. Naithram: did you feel resentful at all? I’d like to some, they
Jess Szmajda: at first, yeah.
Phillip K. Naithram: how could they say something like that? Look at all the nice things I’ve done for them. Like all the, and those are natural human emotion? Like, that’s just, you’re not different from anybody else that receipt. I mean, sorry. variety, human being like, what are you going to do? But
Jess Szmajda: Well, it’s really humbling. And it really was because like, I don’t know. I guess at that point. I’d done some, I think pretty impressive things in my career. And I’m like, I had a big ego
Phillip K. Naithram: Yeah. So, but this is, so what was the work you had to do now that you know? Right. Like
Jess Szmajda: Well one of the first, like the simplest things, was just change how I dress, like I, to just wear t-shirts and jeans, like all the time. and like, Dressing more businesslike. I think, made a big difference. first of all, because it showed people, especially the people outside of the tech group that I took everything seriously, that I was there to build something that they were there to build something and we were all passionate, about the same thing together. And that that subtle cue of Just sort of how you show up, I think is a big thing that seems so natural. to me now. But at the time it was just like, wow, people care. I’m just like I’m living in the world of abstract ideas. like, who cares about what I look like? Especially being trans and not having come out at the time. I’m like trying to run away from, how I look in the world. but
Phillip K. Naithram: Do you think that had a lot to do with it?
Jess Szmajda: I think it did. I think it did. Yeah.
Phillip K. Naithram: think that, like, that was more like you and you trying to like,
Jess Szmajda: well, yeah, like I, I was presenting male still all the time. And the idea
Phillip K. Naithram: that Axios.
Jess Szmajda: is that I’m Toro. Okay. Yeah. So, this is before actually. Yeah. So, this is like 2014 or So
Phillip K. Naithram: how old are you
Jess Szmajda: Oh, then I was 34. at the time. Yeah. So. Yeah, I was, didn’t like to I like men’s suits were like the worst thing in the world for me, because it was like embracing masculinity. It was embracing like being a man. And I was like, I’m not that like, this feels so wrong. And it took me a while to realize why, but it was just always like the worst thing. So, I had to kind of like force myself to like wear a suit, to wear at least just a button-down shirt and a blue shirt and a blazer, not to. Just t-shirts and click, whatever
Phillip K. Naithram: Right. But is that, do you think, like looking back on it, is that why you were addressing in the t-shirt and jeans because you were sort of rejecting the suit because the suit represented being a
Jess Szmajda: Yeah. Yeah, for sure. Yeah. That’s also why I never connected with sports, really?
Phillip K. Naithram: oh yeah. Cause I was asking, did you play sports, but like that would have been you to play it on the guys’ teams?
Jess Szmajda: Exactly. That’s right. Yeah. It was just, it was a lot of things, that I was running
Phillip K. Naithram: so, but I mean, so you’re doing., just like we have mentors in our life for everything else. Right. I have more than one mentor because no one person fills all my gaps there’s a guy that helps me with understanding accounting and finance personally and professionally. I’ve got mentors for career growth, mentors for personal growth mentors for, but did you have people that you can talk to about being trans or coming out or were
Jess Szmajda: want me to have therapists? And I grew a set of friends. in the
Phillip K. Naithram: Was that therapist trans also?
Jess Szmajda: No, no, just somebody who dealt with trans issues and knew how to talk about it. honestly my therapy sessions were pretty fun. My therapist barely spoke. It’s just like, tell me what you all are mine. And I would just talk because that’s who I am. The first session I was like, there’s no way, this is a thing. Well, this is dumb. This is just all in my head. This is a stupid second session. It was just me being like, why am I burdened with this horrible thing? Why is life so terrible and I’m just going to like box it away and run away from it forever. And the third session was like screw it. I’m trans, I’m going to deal with this. And I’m just going to have to deal like, grab the bull by the horns, I guess in a lot. of ways and embrace it. And I mean, you talking to me today, I’m very comfortable with who I am. I’m very, I think I look fine, I think I’m all those kinds of things. but back then I was like, ah, I’m going to go through the real Bardot here, I mean, like. purgatory for, and it was. for the next Year very, and a half of just like looking like a freak for a while and dealing with that.
Phillip K. Naithram: Do you think you looked like a freak or you thought other people thought you looked like a freak
Jess Szmajda: both? Yeah. I mean, it’s impossible to be completely objective, I think in that and yeah. every trans person who goes through transition, like, I think really struggles with that for a while, especially if you do it in your thirties.
Phillip K. Naithram: Oh yeah. Cause you got three decades of not being that way. Right. Yeah, but you know, what’s funny about that, that interaction with your therapist or just those thoughts or those ideas that you can insert, anything you want for being trans, like anytime you’re making a change in your life, are you doing something different?
Right. And that could be, maybe you were struggling with anger issues, addiction issues, whatever it is, insert, whatever you want, those sorts of ideas. And that resistance to the fact that you can speak to someone that we don’t know what we don’t know. So, this idea of talking to someone else who’s going to let you do most of the. And it’s going to help you. It’s very foreign to a lot of us. And I think it’s because most of the time, no, one’s really listening. They’re just waiting for you to stop talking. Right. And that’s a very different thing, whereas that person’s actually listening to you. And that’s probably the first time that you got to actually say all of the
Jess Szmajda: Yeah. Yeah, because this is stuff that had been in the back of my mind. Looking back since it was like eight, you know, and it was just like, things that I’ve been avoiding and not thinking about. directly, but spending some time focusing directly on this thing and being like, no, that shining a bright light. That is a problem. you need to solve. Like, yeah. Going through all kinds of different, life change. I mean, that’s incredibly difficult. I had, I guess I had the additional hill of having to do it in front of everybody.
Phillip K. Naithram: yeah. It was very, very public. Right. It’s unlike some of the other things I mentioned, right. Or going through a divorce or whatever, were
Jess Szmajda: I mean, I’ve seen people struggle with like addiction and things like that. And you like that stuff comes out in your, in your
Phillip K. Naithram: what’s funny is that yeah. They probably think no one knows. We all know.
Jess Szmajda: that’s right.
Phillip K. Naithram: Yeah. everybody knows you’re shaking,
Jess Szmajda: yeah. So, I have a lot of empathy for that. Yeah.
Phillip K. Naithram: It, it, it happens every day. And so, on the other side of that is a freedom. Right. Which sounds like what, you’re, what you’re talking about.
Jess Szmajda: Let go of a huge weight? and I’m able to connect with people a lot more effectively. I’m able to be a lot more present every day like I show up as myself. every day and there’s an incredible power in that. That’s amazing.
Phillip K. Naithram: So how does that allow you to interact differently now with the people around you,
Jess Szmajda: Well, and I’ve Toro. I noticed immediately I had this powerful. authenticity. I was just showing up, and being myself and I didn’t have to like, hold back. I didn’t have to think differently I didn’t have to like, yeah. And every day people, like. Subtly just connected with, me a lot more effectively, even at, Altura where I was feeling some of those challenges in people knowing me before and then an Axios and an Amazon now, and other places, like I find that I’m just more able to connect with people quicker. more directly, more naturally. Like, I think that this is the thing we’ve seen in politics. Like I think one of the great revolutions of sort of politics over the last decade has been like the power of authenticity and I mean, like it or not, the people who have been getting.
elected have Yeah, absolutely 100% uniquely themselves. And they embrace every aspect of that. I think we saw this with, with Trump. for example, I’m not the greatest Trump fan myself, but I and very much appreciated how he was like, no, I did that thing. And that was me and people loved him for it. And I think we see that now in other another political spheres and, and in, in leadership. I mean, people react instinctively and natively to. authenticity in a way that I dunno, it’s a human thing, I think, to be absolutely honest. to be completely truthful and everything about yourself, and it has incredible power in that
Phillip K. Naithram: Yeah. Because if you’re in a leadership role and you can admit that you aren’t perfect or that you don’t know something or that, people will relate to that we can, that resonates with all of us that like, yeah. I didn’t know either.
Jess Szmajda: Well, we’ve all worked with that leader. who’s been like, no, I know what I’m doing. This is fine. You Just, just, just tell me, Jim. What w what’s that actual thing. Yeah. Anyway, we can see through that Instantly no matter how well they are, like pulling the wool over people’s faces, yeah, exactly. But when somebody actually knows what they’re doing, when they are clearly confident when they actually are, themselves and they admit to what they don’t know, we respect those people in a way that we don’t want to. Anybody else.
Phillip K. Naithram: Are you still seeing your coach now to continue to grow
Jess Szmajda: Yeah. Well, I had a different executive coach at Axios. She was great. too.
Phillip K. Naithram: that you sought out or they had,
Jess Szmajda: I, this is actually a negotiated this as part of me as part of my package, me
Phillip K. Naithram: because of the experience you had and the value you saw in
Jess Szmajda: Exactly. Yeah. And so that was really, fantastic. And I think again, helpful at Amazon, we have a different set of mentorships. So, I actually have a mentor. He’s actually a sponsor. We call it now. He’s the internal. Yeah, he’s the general manager of S3 and so
Phillip K. Naithram: three stands for.
Jess Szmajda: Simple storage system. It’s our main is our big like storage product. Kevin’s fantastic. He’s like a, Vr. He’s done a bunch of really great stuff. He’s got a ton of experience that we talk about and I learned from all the
Phillip K. Naithram: what does that look like? Is it the same sort of thing where it’s one-on-one and you meet every so often and.
Jess Szmajda: it’s one-on-one monthly. We spend about an hour together to talk about things that are on my mind varies that I’m having success and struggling with and kind of brainstorm together ways to make that better. Yeah, that’s fantastic.
Phillip K. Naithram: That because you asked for it or it’s just a
Jess Szmajda: Yeah. I asked where
Phillip K. Naithram: Yeah. Sport. So, you’ve learned that like you can ask for this help and people will give it to you.
Jess Szmajda: Absolutely. And frankly, like even unofficial mentors, like I have no shame going to anybody I mean, help me learn about that thing. I want to understand more about this, or like, would you be happy to share your expenses? This is exactly what you’re doing. I think with this podcast it’s like, you go out to people and you’re like, hey, would you tell? me about how you did this stuff? Yeah.
Phillip K. Naithram: That’s hey really all it is. It’s like, I am almost, I’m desperate to learn how people are doing the things that they’re doing.
And what’s not, you can read the books about Michael Jordan. And it doesn’t feel I can get better at basketball. I understand this growth mindset. 100%. If I start playing basketball every day, then I’ll get better at basketball, but I may not replicate his career. There are people all around that if you want what they have and you do what they do, you might end up getting what they got, like you can really find, and they, they are happy to mentor you. I’m just a person. And I’ve been able to have coffee and with people that I wouldn’t have expected would have shown me any attention or had any conversations with me and they do.
And, and that’s what I was after. And then I thought, well, there’s probably other people like me. Why don’t I share that with them? And being in the government, contracting, federal services community, you see so much entrepreneurship, so much leadership between the three. If I could just be even one step in the bridge to connect all three of those,
Jess Szmajda: Well, I mean, the that’s the thing, you mean you hit the nail on the head, like we’re all just people. like, no matter what we’ve done in our lives, I think it’s like people don’t really amazing things in their lives. but there’s just a human being who has had a life just like you and me, and like had struggles, had challenges found a way. through, and some people start with more privilege than others. Sure. Yeah. That’s a big thing Don’t get me wrong. I get it. But and like seriously, like. the, if you go up and you’d ask somebody like, what’s the worst you’re going to get. there and be like, oh, I’m busy. thanks.?
Phillip K. Naithram: Yeah. And that doesn’t even mean that I won’t do it. It’s just, not when you ask them, like, hey, and it, and obviously we learn, you’ve got to understand people a little bit to ask the right way. it was like, hey, when you’re free, can you talk to me? That’s not going to get anywhere. Just like, can we meet on Thursday at 2:00 Exactly.
Jess Szmajda: Yeah. Be specific. Be clear about what you’re looking for. Try to find a specific time, yeah.
Phillip K. Naithram: I’m very grateful for the people that have spent time with me on the show and we get to talk about this and have an open dialogue and it’s, it’s, it’s, it’s important to do that. And I’m very grateful that I get to learn, we all hear this phrase imposter syndrome, but no, one’s to hear someone actually talk about what it feels like to be there, that feeling of impending. That just sets in for no apparent reason, because he had a great call at 10:00 AM. And then at 1:00 PM, it’s like, oh my God, this company is going under.
Jess Szmajda: been there.
Phillip K. Naithram: Like, why am I here? I don’t understand why people keep asking me questions. I, like I’m not the guy,
Jess Szmajda: that’s right
Phillip K. Naithram: but then by four o’clock it’s like, you know what, let’s just get back to doing what we’re doing. Let’s chip away at it. Let’s make, we’ll make something work. And then,
Jess Szmajda: I call them the brain weasels
Phillip K. Naithram: It’s yeah, it’s, it’s really an up and down thing. And I think, yeah, it’s that feeling of like, I shouldn’t be doing the thing that I’m doing because I know all my secrets and everything that I’ve done wrong and every crazy thought that I’ve had that never left my mouth, but I know about, and I remember, and I probably repeat to myself I know all of those things and it’s that, that makes up this feeling of not enough or that’s really, I think for me, when I, if I think about imposter syndrome and like anything that shows up it, and it’s usually happening when I’m doing something new and doing something new means that I’m doing something where I can grow. So, it’s never a bad thing.
Jess Szmajda: Push yourself.
Phillip K. Naithram: exactly. I mean, it’s like working out, so I’m lifting this, this, this weight that I’ve never done before. It feels scary, but I push and I do it and I eventually get stronger. Or you running farther or whatever. Yeah. And I, I think it applies to, to work to you, take a position that maybe you didn’t think you were qualified for only to realize that you just got to learn a bunch of stuff and now you’re qualified
Jess Szmajda: Well, I mean, that growth mindset, like you mentioned, I think is A big thing. And I think that’s this is why we like so many leaders referenced like sports and other sorts of activities is because that’s a place to learn that in a play in a, in a, in a sort of activity, surrounded by play. and by fun and, and, and with less, I think stakes at the table until you get into pro sports, I suppose, but, but like, if you can go and learn that you can push yourself and you can grow and you can do more like in other venues, in other non-professional venues, like I think it’s a fantastic opportunity to So, to be able to take that, understanding back to what you’re doing in the workplace. And that’s powerful.
Phillip K. Naithram: we’ve talked about so much today. And I, and I really appreciate you opening up and that’s with the whole point of this to have a real dialogue around the ideas of mindset leadership, develop. Personal growth. You shared a lot about like what you had to do coming out and transitioning and I think that anyone who’s ever had to do something difficult will relate to the mindset and the thoughts and the ideas that are centered around that. To some extent, even if they’ve never had that
Jess Szmajda: Well one thing, by the way, like the transition, I think has really given me an incredible perspective on being a woman in business and in tech and in leadership like people now see me as a woman. like people don’t see me as anything else and they treat me very differently. than how they used to. Yeah. Like I tell people, I, I knew that people were finally seeing me as myself, and they started talking over me in meetings, but this is real. And this is like I think one thing that I really want to hammer home for people, who are paying attention to this, like women marginalized and it’s in subtle things that people do every day in unconscious things that people do every day. And like, I can see this because I’ve seen both sides of that coin. And I think that I have this opportunity to like really raise a flag here how we fix this I mean, I think we have to be intentional for a while, but like let’s make sure we add. like, so-and-so what she thought or let’s make sure that we’re not just like dismissing someone’s ideas because of how they look or where they come from or the kind of like language they use. or, I mean, like I work with a whole bunch of people who have thick accents now. and like it’s I think it would have been easy for me to discount that earlier now. I’m like, no. I mean, the. it doesn’t. matter where you come from, doesn’t matter what kind of background you have. I mean like people with different skin tones and different kinds of experiences, like, everybody’s a human, everybody’s gone through this kind of, their own journey. and like to get back to this sort of like, every individual’s amazing, like everybody’s gone through something and they’ve gotten to where they are. through a lot. And I want to learn about that. I want to understand who they are, who they are as a person. And I want to respect them. all. And I want to. Be open and listened to them and pay attention to them. So, it’s an incredible. I think it’s incredible superpower. that I have gained now to recognize that this happens all day, every day in the world and something apprentice share more.
Phillip K. Naithram: Well, that ties into, so a question I’ve been asking everyone that’s been on the show is. About a jumping off point, a moment in time where they couldn’t keep doing what they were doing, but they knew they had to do something different and they weren’t sure what that different was. Right. And it could also tie into a moment in time where you thought it was a horrible thing that happened to you. And now you’re truly grateful for it. D can you, I mean, I
Jess Szmajda: yeah. I mean, Yeah, my transition is that yeah. A hundred percent. I mean, like,
Phillip K. Naithram: I felt like we covered it,
Jess Szmajda: yeah, we did.
Phillip K. Naithram: yeah. I just want to make sure I gave him there might’ve been something else it’s like.
Jess Szmajda: I think you’re Right. I mean, like there’ve been others, but that’s the big one
Phillip K. Naithram: I mean, you look back on it and, and I, I, and I can hear it in what you’re saying. Cause I’ve forgot experiences where like I’m only the person I am now with the frame of reference in the thought process and the, and the mindset and the ideas and the perception of the world and the people around me because of that period of time, that was incredibly difficult. That at the time I could have been like, well, I could do without this, but now I look back and I would never change any of that because of. have that. I wouldn’t be this.
Jess Szmajda: Absolutely. I mean, that, that’s the big one for me. There’ve been other times in my life. I think that I’ve been also like, I’m going through a lot of trouble and a lot of pain like right now, I’m, a month into my role as GM. And I’m spinning up on a lot of stuff. and I’m resetting things and I’m changing direction. And I’m drinking from the fire hose. I am working like 80. 90, a hundred-hour weeks right now. And it’s a lot, it’s pretty painful, I’m not going to, I’m not going to lie, but I know that that’s a part of like, sort of switching lanes and moving into this lane and being effective. in this position. And like, I know because I’ve gone through things like this before that I’m going to figure it out and things are going to make sense. And my life’s going to get back to, something that I can sustain and I’m going to be more effective I’m going to be able to do more. amazing things. I’m going to be able to help people do more amazing things too. So, that’s, I think there’s a huge power in having gone through those kinds of challenges in. your life and knowing that you can. Work through it. And that’s an incredible, like personal power
Phillip K. Naithram: Yeah. I mean, that’s the, that’s the purposeful, I have a morning routine that seems like daunting to other people, but I purposely put myself through things like that. A lot of people talk about that. Do hard things on purpose because it builds the mental resiliency and
Jess Szmajda: the thing that was my Mo my sort of like mantra. when I was starting to transition. It’s like, I can do. cause I can
Phillip K. Naithram: take the cold shower. It’s not going to be that bad. It’s probably, you think it’s colder in your mind than it actually is. And then you get in there and you realize, Hey, it’s not
Jess Szmajda: exactly I can do hard
Phillip K. Naithram: Right. And then where does, where else would that show up in your life? Well, look, I know you’re busy and I, you just talked about your 80-hour weeks and I took an hour out of it. So, I appreciate you spending time with us and thanks for being here today.
Jess Szmajda: Thanks for the thanks for having me. Appreciate it. All right.
