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Ever meet someone who spent 20 years opening casinos and managing nightclub marketing then pivoted into cybersecurity at 38 with no CS degree and no certifications? That's Michael Steffen's story. WHAT YOU'LL LEARN: Michael built his entire career on one skill most tech companies overlook: the ability to meet people where they are. From Las Vegas Strip night clubs to a $7 billion casino opening in the Philippines to DEF CON volunteer work, every chapter sharpened something the tech industry desperately needs and rarely talks about. KEY TOPICS COVERED: • Growing up between Connecticut, California, and Las Vegas and what being the odd one out taught him • Learning HTML and building online communities as a teen before "tech" was a career • 20 years in Las Vegas hospitality: restaurants, the Wynn, Caesars Cromwell, and Linq • First leadership role: the hard lesson of ownership and why "you have to eat it" • Three years in the Philippines opening a $7 billion casino resort • Raising a daughter by FaceTime - and what that sacrifice clarified • Sitting in a boardroom with Frank and Lorenzo Fertitta: knowing your numbers, saying the hard thing • Why the Palms closing pushed him toward a career he never expected • The jiu-jitsu training partner who told him he was miserable and handed him a Security+ study guide • Getting to the top 10% on TryHackMe starting at 38 • Three years volunteering at DEF CON: how it opened every door • Why soft skills are the most undervalued asset in tech right now • The difference between networking and building organic relationships • Parting advice: do the hard thing, even when you can't see the payoff TIMESTAMPS: 00:00 Introduction and Episode Overview 01:37 Michael's Current Role: Targeted Account Sales in Tech 04:00 Growing Up: Connecticut, California, Las Vegas 07:42 Learning HTML and Building Community Online as a Teen 13:00 Working Las Vegas Hospitality: Restaurants and the Strip 20:00 The Wynn: XS and Tryst. Where Soft Skills Got Serious 27:00 Moving to Caesars: Launching Cromwell and Linq 33:00 First Leadership Role: Ownership, Accountability, and Learning to Let Go 40:00 The Philippines: Opening a $7 Billion Casino Resort 46:19 Raising a Daughter by FaceTime: Sacrifice and Perspective 52:26 The Palms Opening and the Fertitta Boardroom 55:45 Building Organic Relationships: The Rolodex Lesson 01:01:01 Say the Hard Thing: What the Boardroom Really Demands 01:06:07 The Palms Closes and Everything Shifts 01:09:14 The Jiu-Jitsu Pivot: "Man, You Are Miserable" 01:11:14 Getting Into Security+ and TryHackMe at 38 01:16:24 Volunteering at DEF CON: Three Years with CTQ 01:17:29 Soft Skills in Tech: The Conversation the Industry Isn't Having 01:26:11 Parting Thoughts: Do the Hard Thing 01:29:36 Las Vegas as a Convention Hub: Go Volunteer ABOUT MICHAEL STEFFEN: Michael Steffen spent over two decades in hospitality and marketing from Las Vegas nightclubs to a $7 billion resort opening in the Philippines. At 38, a jiu-jitsu training partner told him he was miserable and handed him a Security+ study guide. He passed. He volunteered at DEF CON for three years. He's now in targeted account sales in the cybersecurity space, building a career on the soft skills most of the industry undervalues. CONNECT WITH MICHAEL STEFFEN: LinkedIn: / myksteffen ABOUT CAREER DOWNLOADS: Career Downloads is a technology career podcast hosted by Manuel Martinez, exploring diverse career paths in the tech industry. Each episode features conversations with professionals sharing their journeys, lessons learned, and actionable advice for managing your own career more successfully. NEW EPISODES every Tuesday Subscribe for weekly career insights and technology role exploration CONNECT WITH CAREER DOWNLOADS: Website: https://careerdownloads.com LinkedIn / career-downloads YouTube / @careerdownloads TikTok / careerdownloads Instagram / careerdownloads FaceBook / 61561144531249 Produced by: / parker-weller-b6683336b #TechCareers #CareerPivot #CareerAdvice #Cybersecurity #ProfessionalDevelopment #CareerGrowth #Hospitality #LasVegas #CareerJourney