I generally don't make cold calls, at least when it comes to inviting folks to be on Real Technologists. Jess Szmajda and I crossed paths through our online cybersecurity and cloud computing networks. She's a general manager at AWS leading Network Firewall and Firewall management business. Previously, she was the GM for the VPN practice.

With her online profile saying she's located in Washington, DC, I made the assumption that she works with the federal government. Oops! Never make assumptions!

I could tell there was technical depth and a driving passion to impact others.

It was time to set up a chat.

When we met, it was during late August. The air was still warmed by the summer sun, and the evening was just beginning to hint at the cooler days ahead. Perfect weather for an energizing discussion and forward thinking ideas.

Jess Szmajda's presence was an instant uplift. She has a delightful laugh that punctuates many of her sentences.

Jess Szmajda: Well... I was actually born in the district. I think I was one of the five people born in DC that year.

I'm a general manager. I own some of our network security services... network, firewall and firewall manager. A general manager at AWS is a bit like a CEO of business line. So I've got a couple products that I own and responsible for P and L and... all people sales, go to market, customer support, everything you name it. I lived in or near DC for most of my life, and I've never worked for the government. I don't know , the government thing, it's just never made sense. It's never been the place for me.

We are approaching the midway point for Season 2 of Real Technologists. Senior, Pokie, and I wanted to take a moment to thank you and reflect on the past year. During Season 1, we learned that our eyes were bigger than our stomachs, so to speak. We had decided on an aggressive schedule of weekly podcasts. And like our guests, we learned a big lesson and had to pivot.

This Season, Season 2, is focused on sustainability and growth. We love getting to know our guests, learning their stories, and crafting the podcast.

Real Technologists is about telling captivating stories and diverse journeys of those shaping our digital future. From the heart of innovation to the forefront of change, technology continues to redefine our world, and behind every breakthrough lies a human narrative waiting to be told. Our team is split. Pokie works from our New York office. Senior and I work together from our Camp Hill location. As radio personality Pete Womback used to say, "It's a beautiful day in Pennsylvania".

To keep the quality high and keep ourselves sane, we're delivering bi weekly. We embark on a journey of exploration, uncovering the unique experiences, perspectives, and challenges that have shaped the lives of our guests.

Trac Bannon: When Julie Holdren, co founder of DC based Watering Hole AI joined our call, I immediately noticed stylish designer glasses with a popped collar. That lasted for only a few moments. Julie had a ton of connection and bandwidth issues. So after disconnecting and switching networks, Senior asked Julie and I to talk "cameras off".

I'm glad we had those first few minutes visually... pleasant banter and noticing where my guests are zooming in from gives me additional clues for asking questions. The only clues I could glean is that Julie is very pretty, had her laptop perhaps sitting on her lap, and had what seemed to be naturally serious countenance... I guess inherently resolute.

When prepping to interview a guest for Real Technologists, Senior and I do a very small amount of detective work. I've been a guest before when someone has done a tremendous amount of research and at times, I felt like they were not getting to the real me. And that is why each Real Technologists episode is a journey of discovery; too much research would taint me from asking really interesting questions that just randomly pop up as we chat.

What we learned in our prep investigation about Julie is that she represents the new gig economy, but for executives in technology... a career style born of entrepreneurial culture, globalization, tech advances, and a changing workforce preference... giggers... instead of one role, giggers prefer many roles or jobs instead of just one... tons of gigs.

As a renowned technologist with extensive experience in communications networks, cryptography, mobile technologies, and data science... why did she gravitate towards gigging? I'd say it started when she was a kid growing up in DC!

Julie Holdren: I went to school in Fairfax County at the time. They were teaching Pascal and Basic in high school. So I graduated from high school already programming. and it was an elective. It was easy. It came to me easily. I was, one degree shy of a math major. So at the time, there wasn't code generation tools and debugging tools the way they are today, which makes things a lot faster. So we ended up doing and learning very low level code through high school. I initially got exposed through the DoD in middle school to one of the first computers through my Girl Scout program. And earned a computer badge in middle school. And I think that piqued my interest.

Trac Bannon: John Kaufhold is one of those super smart people... you know the ones... when you read their LinkedIn profile and do a little googling, their achievements and academic records are phenomenal. I was initially a bit shy about reaching out to talk with him.

I'm a techie. I'm not a data scientist though I'd like to think that I'm math and AI adjacent. John's contact information was shared with me by Jennifer Ives, CEO at Watering Hole AI and a Real Technologists alumni.

When I hopped on the call with John, he surprised me by being a few minutes early in hopes of meeting Bob. That's become a theme with guests... on this particular Friday evening though, it was only John and me. I was immediately drawn to John's personality. During the rest of our chat, I figured out why. Like me, John grew up in what we like to call "the rest of Pennsylvania", the part that is not metro Philly.

John grew up in Lancaster, Pennsylvania. In fact, his wife Liz, who he affectionately calls "the boss" grew up there as well. Lancaster is steeped in U. S. history and is known for its well preserved historic buildings. Lancaster is also known for its large Amish population. It has one of the oldest plan people communities in America.

John describes his upbringing as typical blue collar. His parents loved him deeply and placed an emphasis on education sacrificing to send him to a private Catholic school.

John Kaufhold: Second street. Yep. And the boss, she grew up in Schooling Hills, which is like the, you know, the nice part of town. I went to Sacred Heart school. My mom and dad. my mom was a Bell Telephone switchboard operator. And my dad, he was a radar operator in the Navy. And then he got a job as a network technician. And neither of them had a college degree. So it was kind of a big deal for them to spend that kind of money to put Mike and I in Catholic school.

Trac Bannon: His parents, especially his mother, invested not only the funds for John to attend Sacred Heart, she invested a ton of time. She made sure John and his older brother Mike were set on a solid educational path. She did all this while battling illness. When John was still in elementary school, his mother was diagnosed with breast cancer.

John Kaufhold: What my mom did as she was dealing with 10 years of... recovering from mastectomy and chemo and just the slow process of breast cancer. She was making sure that Mike and I, we were her project... and she made sure that we got all the educational opportunities she could possibly give us. So she put us in these programs at the local college, Franklin Marshall... and we would take... like some kind of Saturday classes and it would be us, these two very blue collar kids, and then all of the rich kids in class.

Trac Bannon: A few years ago, I was introduced to Helen Beal through our work with the DevOps Institute. Helen was the Chief Ambassador and I was submitting my credentials for consideration as an ambassador.

We are both combed-shaped people and naturally had so many topics and passion areas to talk about. What is a comb-shaped person, you may ask?

It's more likely that you've heard the metaphor of a "T-shaped person". The horizontal bar of the letter "T" represents the breadth of skills in multiple areas... the vertical bar of the "T" represents exceptional depth in one area. T-shaped folks are very very competent in their primary field. Their breadth is a little more shallow though it is this mix that helped "Ts" to collaborate with a wider context.

Well, what, then is a comb-shaped person? The spine of the comb represents competency and awareness in a bunch of topics... much like the horizontal bar for the T-shaped person. Each tooth of the comb is a different area of depth. This is Helen Beal. She is particularly valuable in situations with rapid change... she is that person who can synthesize with many different deep specializations.

I admire this life force named Helen Beal. We have a shared commitment to technical expertise, continuous learning, and community engagement. But it is her ability to juggle roles and interests that makes me simply a fan girl. It was time to learn more about this Real Technologist.

Helen was born in Yorkshire in the North of England. The countryside, history, and distinct regional character remind me of Vermont. When she was six, her father left the Royal Air Force and took a job with a civilian airline that included moving the family closer to Gatwick and the international airports.

Her mother was a science teacher, and it was her mother who decided to teach her to read along with her older brother Simon when Helen was barely three...

Helen Beal: So my mother taught me to read when I was three. I was holding books up when I was one. I held them upside down. I can actually read quite effectively upside down, which is quite handy when you're opposite someone at a desk or in a restaurant and there aren't quite enough menus to go around.

Simon is 18 months older than me. And the reason my mother taught me to read at 3 is because she was teaching him and she could see that I was also ready. So she taught us both together.

I've always been a bookworm. And that's kind of my first love really is reading and storytelling and writing with, you know, they're so intertwined.

And I think at school I was a swot, frankly. I was a nerd. I really enjoyed school. I really enjoyed learning. I was the girl that would finish the maths exercises and ask the maths teacher for more maths, please.

🎙️ Free access to “Real Technologists” on your favorite podcast platforms: bit.ly/realtech-on-all-podcast-platforms 📌

Bob: Ok, Trac , let’s check your levels

Trac: Check 1-2, Check 1-2, Season 1 Episode 20, Check 1-2

Bob: Ok, levels sound great; make sure you are set to record individual tracks

Trac: Roger, got it.

Bob: Ok, I’ll fade out and see you kids later, have fun

Trac: Thanks, Senior

"You are listening to the Real Technologists Podcast. I'm your host, Trac Bannon." (Fade to silence.)

That’s how most recording sessions for the Real Technologists Podcast start. My recording engineer checks the audio levels for me and my guest. I want to back you up just a few moments, though. Senior usually opens up the zoom bridge; he knows that I am often scheduled back to back and will arrive just-in-time.

With rare exception, Senior is always first on the line to greet the guest. In fact, I’ve had a few guests join early just to chat with him. I suppose it is because like each and every guest on Real Technologists, Senior is authentic.

During Season one, a few characteristics have started to emerge with this wildly diverse set of alumni. I’ve mentioned authenticity but how about lucky? To be honest, I don’t believe in luck. I believe in Senior’s definition: Luck is when preparedness and opportunity meet. Each of my guests had moments when a door opened and they walked through. At times they didn’t feel prepared and still they said yes.

Perhaps that’s why so many have felt at times that they lacked what the role needed… that they were posers or imposters. Amazing to think how many of these digital disruptors sometimes doubted themselves.

They don’t quit, though. They have a certain stick-to-it-ness… a real grit…

A few of the alumni shared the stress of working in tech… the coping mechanisms…when mixed with the prevalence of alcohol in the industry, it is amazing that at least two guests have shared their story and the need for us all to normalize sobriety.

This first season has brought me tears and belly laughs, inspiration and awe. It’s given me an opportunity to consider my own journey and what motivated me to start #Real Technologists.

What will Season 2 bring? Well, we already started production and it keeps happening… guests showing up early to talk to Senior…Apologies to John Kaufhold for being one of those rare exceptions when Bob couldn’t join. Without silent time queues from Senior, I kept this artificial intelligence, machine learning, and data science expert on for over two hours. OOPSIE!

I had an awesome chat with Julie Holdren from Wateringhole AI and dug deep with Jess Szmajda

Bob: Hey Trac, its “schm-eye-da”

Trac: “schm-eye-da”, okay, thanks Senior

Jess Szmajda from AWS is also a part of season 2. Without giving you a spoiler, I can say without a doubt that season 2 of Real Technologists will give you, Something to noodle on.

Doing our normal timeboxed guest research on SBI's Chief Technology Officer, Tracy Edwards, was both difficult and curious.

Why curious? Prior to 2018, this Tracy Edwards spent her career more focused on humans and not technology. Once exposed to the idea of product management and bridging the divide between business and tech, she completely reinvented herself and her career, pivoting to product development and leading engineering teams.

Why was the research difficult, though? There are multiple Tracy Edwards from New York City.

Tracy Edwards:

Until recently, the most famous Tracy Edwards was the person who escaped Jeffrey Dahmer, which was a real interesting thing in the Google searches. Then there is a Tracy Edwards, n y c, who is almost an exact doppelganger to me with like glasses, blonde hair, whole bit, although she seems to have a much more fabulous socialite life. So I kind of like that runoff. And now there's Tracy Edwards, the very famous sailor who has a full documentary about her.

So I feel like I'm in good company and I don't mind if I'm buried on the second or third page.

I'm noticing a few core traits in the many guests I've hosted for the Real Technologist podcast. Authenticity and a willingness to say yes. This rings true for guest Jonathan Rivers. He was recommended to me as somebody who absolutely is passionate about making opportunities for others.

Talking with each guest is filled with surprises and challenges my own preconceived notions. Jonathan Rivers is the CTO of Fortune Media which includes Fortune Magazine. In doing some research, I came across Jonathan's headshot. Sometimes his photos show a mild smirk though often the photos have an intensity that you feel. This looks like the kind of person that you want on your side, especially when the chips are down.

Interestingly, my expectations for the Zoom call were that I would see an opulent executive office in a high rise overlooking a spectacular view. Perhaps with some modern art chandelier. What I encountered was an average guy in what looked to be like an average cube spot or office touchdown spot. The lighting was less than average, though it doesn't really matter for audio. Over his shoulder was the only discernible decoration: a whiteboard with an architectural diagram scribbled in marker.

He doesn't smile often, though when he does, you feel a sense of satisfaction that he is human. I would not say that he's a big old teddy bear like my close friend Bryan Finster. Instead, I would say that this is a super intense and intelligent human.

As we discussed his origin story, and going from a kid in Texas to the CTO of Fortune Media, we touched on myriad topics including his philosophy on diversity. I was very curious what I was going to hear from this white, middle aged biker dude.

Jonathan Rivers:

It's incredibly near and dear to my heart. For so many reasons. One, I'm really proud of the team that I've built here at Fortune.

I built it with that in mind. And I'll tell you why... One, 'cause it's the right fucking thing to do. But more importantly , you look at this from a tech industry perspective, the moment that you establish a bro culture in tech, if you hire a bunch of white nerds out of suburbia that all wanna talk about Fortnite, you are sunk, right?

If I hire me, me number two is gonna have all the same blind spots that I have.

And I want a team of really different people that see things from different backgrounds, that see problems from different angles, that want different things out of life. Frankly, they all behave better. Everybody behaves better when you're in mixed company than when you do when you're with your buddies.