Episode Inforrmation Show NotesWhat does it take to walk away from a 20-year career in hospitality and start over in tech at 38 with no degree, no certifications, and no hard skills? For Michael Steffen, it started with a jiu-jitsu training partner telling him he was miserable and handing him a Security+ study guide. He passed. He volunteered at DEF CON for three years. He’s now in targeted account sales in cybersecurity and he got there without ever applying for a single tech job.Michael spent two decades inside some of the biggest casino openings in Las Vegas history. The Wynn, Cromwell, Linq, and the Palms and opened a $7 billion resort in the Philippines while raising a daughter by FaceTime. He sat in boardrooms with the Fertitta brothers and learned what it means to know your numbers and say the hard thing when everyone else is hedging. When the Palms closed and left him without direction, he didn’t go back to hospitality. He went to TryHackMe instead.In this conversation, Michael breaks down the skills that actually got him into tech: how meeting people where they are became the throughline of his entire career, why organic relationships built over years beat transactional networking every time, and why volunteering at DEF CON opened every door a resume never could. He’s blunt about what the industry is missing. Tech has no shortage of people who can execute. It’s short on people who can actually talk to other people.TOPICS COVERED:• Growing up between Connecticut, California, and Las Vegas• Learning HTML and building online communities as a teen• 20 years in Las Vegas hospitality: restaurants, the Wynn, Caesars properties• First leadership role and the hard lessons of ownership• Three years opening a $7 billion casino resort in the Philippines• Raising a daughter by FaceTime• The Fertitta boardroom and what it demands• Why the Palms closing pushed him into tech• Getting Security+ and TryHackMe at 38• Volunteering at DEF CON with CTQ• The difference between organic relationships and transactional networking• Soft skills as a career advantage in tech sales• Parting advice: do the hard thing even when you can’t see the payoffWHO THIS EPISODE IS FOR:• Anyone considering a career pivot into tech from a non-technical background• Hospitality, marketing, or sales professionals wondering if their skills transfer• Tech professionals who know they need to get better at the human side of the job• Career changers in their 30s or 40s who think they’ve missed their window• Anyone who has ever felt like the wrong person in the right roomCONNECT WITH MICHAEL STEFFEN:LinkedIn: https://www.linkedin.com/in/myksteffen/ABOUT CAREER DOWNLOADS:Career Downloads explores technology careers through conversations with professionals who share their journeys, lessons learned, and practical advice. Hosted by Manuel Martinez, each episode exposes listeners to different technology roles and helps them manage their own careers more successfully. New episodes release every Tuesday.Connect with Career Downloads:Website: https://careerdownloads.comLinkedIn: https://www.linkedin.com/company/career-downloadsYouTube: https://www.youtube.com/@careerdownloadsTikTok: https://www.tiktok.com/@careerdownloadsInstagram: https://www.instagram.com/careerdownloadsFaceBook: https://www.facebook.com/people/Career-Downloads/61561144531249 TranscriptionManuel Martinez: Welcome, everyone. My name is Manuel Martinez And this is another episode of Career Downloads, Where each episode I Basically hit the Refresh button, bring on a different guest to learn more about their background and their experiences to help you uncover any actionable advice that you can use as you’re managing your own career. So for today, I have with me Michael Steffen. He and I have met through a… mutual– I’m going to say colleague Through Dennis, who I’ve had on the show actually right before this one. I got to talk to Michael, learned a little bit more about his career into tech, and just fascinating everything that he has done beforehand. So I think there’s going to be a lot of transferable skills, a lot of kind of what he’s doing. So with that, I’ll go ahead and introduce Michael. Michael Steffen: Hi, I’m Mike. Manuel Martinez: Appreciate you coming on and being open to telling your story, so times that we talked prior to this, prepping forward, there’s a lot of good information. And I was like, I want to dive deeper, but- Saving it for today. So to start off, if you can just tell us what your current role is and some of the responsibilities, and then we’ll work our way there. Michael Steffen: So I’m on a targeted account sales and a little bit of marketing support as well. I like to think of it as a good mix between understanding the tech side of it but not being a sales engineer, because those guys are… and gals are light years smarter than I ever will be on that side, but at the same time, be able to blend some of the soft skills too, and still know what I’m talking about, and be able to hang with CISOs or otherwise. Right. Manuel Martinez: So now, if you can kind of bring this back a little bit, and tell me a little bit about where you grew up, and eventually what you thought you were going to do, and kind of what led you to start in your career. Michael Steffen: So I grew– I was born in Ohio. I lived there for about six months, four days, and like 13 hours, according to my parents. We got out of there. Moved to Connecticut, was raised there for most of the time. Spent a lot of the time in the late 80s and early 90s, going to the city a lot starting to understand- by city being New York City. Boston as Well. Really getting to understand the East Coast and my formative years. Then we moved out to California when I was about 12. Lived there for two and a half years. Everybody always asked, hey, was your family in the military? It’s like, no, they were in health care. And health care, at that point, you bounce around just as much sometimes. So back then, my mom was– she was a VP at one of the health care companies. She had worked her way up from being left with nothing, when my dad left, to having a real job, and breaking the glass ceiling. So that, I think, set me on a trajectory to know there’s something always out there, and you can always pivot. And there’s still a chance, no matter how far down you think you are. We went to California. We stayed there for, again, I think two and a half years. Went back to Connecticut, culture shock in the beginning of high school, coming from Southern California at leaving in eighth grade and coming into ninth grade in a small town in Connecticut. Truly night and day. For six months out of the year it’s gray. You never see the sun. You have to dig your car out. Where before, it’s 65, 70 degrees all year round. The worst thing you have to deal with is a 40-degree morning. And I was this skate surf and snowboard guy. I don’t know what that is, but I’m here for it. So it’s like, hey, that was a lacrosse soccer football town. Night and day. And I didn’t have a lot of friends. I was the weird guy who didn’t grow up there. They all knew each other from kindergarten on, or their parents were relatively high up, or they all worked together. I was the odd man out. So I kind of realized too that, hey, if I’m going to be the odd man out, I might as well just kind of embrace that and see what’s out there for me. And I realized too, my stepdad at the time, he was big in the computers. I mean, the old big monitors. And every single year, we got a new box. And I was pumped about learning it. I gravitated towards that. So in high school, freshman year, it was M-I-R-C, and it was the Wares groups, and I was learning all that. I was big into gaming, not just in the video game stuff, but like tabletop stuff too, because again, I was a typical nerd, right? Not the sports guy. Not the sports that you could do 12 months out of the year, at least. So I found people online and I was like, hey, this is a play by post kind of thing. Later era BBSs kind of thing, play by post, whatever. I needed to learn how to develop HTML to create these pages to keep these stories moving. And I think really the formative thing for me was like, hey, go figure out how to do markup, do HTML, go get a book, HTML for dummies. I think everybody had one of those at one time. I think people still probably have it, I hope. And it kind of just opened my eye, I can create something, we’re just sitting at this machine that I’m gonna sit at anyway, because I can’t seem to socialize, and kind of create my own world. So it did. And that led into, I would say a passion of four years of that while still, you know, a lot of snowboarding there, did a bunch of competitions, skating every time, the weather wasn’t absolutely atrocious. And I gravitated to those cats. And I found a little friend group there, and I was really, really lucky. But they were also really accepting the fact that I was different than them. You know, they were the punk rock kids, and sure I was in and out a little bit, but I was mainly coming home, and I was just in front of my box, and I was enjoying the worlds that I was creating with my friends there too. So I had that kind of duality, and it kind of made me, I think, it really formulated, or formed a love of the opportunities online and in the tech space, without even really knowing what that was at the time, Manuel Martinez: you mentio...