Tech Legacies

Hosted by Fanny Dunagan

Technology Business

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Jun 2026

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About the show

Want to get ahead in the tech industry? Want tech insights? Join host Fanny Dunagan as top executives share their untold stories about their tech careers, reveal what lessons they've learned, and offer advice for professionals who hope to get ahead. Are you motivated? Looking for career growth? Then make sure you follow this show. Get tips from tech executives from AT&T, FedEx, Verizon, Hasbro, Textron, and EY. Discover strategies for technology and team culture. Learn about the importance of innovation and how it drives company culture. Enjoy personal stories and leadership advice. Gain valuable leadership skills and explore new ideas. If you want to succeed in tech, then Tech Legacies with Fanny Dunagan is for you!

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June 16, 20262 min

They Run Phishing Attacks On Their Own Staff | E03b

Most companies try to prevent phishing attacks.Mastercard runs phishing attacks on its own employees.In this clip, Jon Brickey discusses how Mastercard keeps its teams prepared through monthly phishing simulations, capture-the-flag competitions, cyber defense exercises, and large-scale crisis response training.From friendly competitions and pizza parties to realistic cyberattack scenarios involving major corporations and government agencies, cybersecurity readiness requires more than technology. It requires practice.Topics discussed:• Why Mastercard runs monthly phishing simulations • How employees are rewarded for identifying malicious emails • What capture-the-flag cybersecurity competitions look like • How red teams and blue teams train together • The role of CISOs and incident response leaders during cyber crises • Why collaboration between industry and government is critical during cyber events • How organizations prepare for attacks they know will eventually happenCybersecurity isn’t just about defending systems. It’s about preparing people.If you could implement one cybersecurity training exercise at your company, what would it be?-----------------------------Connect with Jon Brickey on LinkedIn at https://www.linkedin.com/in/drjonbrickey/Want to build your authority and brand as a tech leader? Subscribe to our newsletter for updates, a free branding guide and 1-hour training for tech professionals: https://techlegacies.ck.page/newsletter Connect with the podcast host, Fanny Dunagan on LinkedIn at https://www.linkedin.com/in/fannydunagan/Links to the full episode on YouTube, Spotify and Apple Podcasts: https://linktr.ee/techlegacies-------------------------Huge thank you to the sponsors and partners of the #TechLegacies podcast. Hit that FOLLOW button on their pages for the latest updates:🔹 https://www.linkedin.com/company/cginfinity/ - IT Consulting Services, especially in energy and Salesforce🔹 https://www.linkedin.com/in/shaunnablack/ - Executive Coach and & Heart-Centered Leadership🔹 https://www.linkedin.com/company/odyssey-information-services/ - IT recruitment and managed services🔹 https://www.linkedin.com/company/techcxolaunchpad/ - Program to elevate you to senior leadership and C-Suite🔹 https://www.linkedin.com/company/marketscale/ - For your studio recording needs and platform for user content👍 Like, subscribe, and share if this resonated with you

June 9, 20262 min

I Bet You Didn’t Know This About Mastercard | E03a

Most people think Mastercard is a credit card company.It’s not.At least, not anymore.On a recent episode of Tech Legacies, Jon Brickey shared a perspective that may surprise many leaders: Mastercard is fundamentally a technology company operating in the payments industry.While its iconic logo is visible on billions of cards worldwide, Mastercard’s role extends far beyond consumer transactions. The company builds, maintains, and operates the network that connects consumers, merchants, financial institutions, governments, and businesses across a global ecosystem.Even more interesting, traditional payment networks now account for only about 60% of Mastercard’s business.The remaining 40% comes from services, including cybersecurity, threat intelligence, risk management, and fraud protection. Through strategic acquisitions and innovation, Mastercard has expanded its reach far beyond payments to help organizations better understand and manage risk.It’s a powerful reminder that the companies we think we know are often evolving far faster than public perception.What company surprised you when you learned what they actually do behind the scenes?-----------------------------Connect with Jon Brickey on LinkedIn at https://www.linkedin.com/in/drjonbrickey/Want to build your authority and brand as a tech leader? Subscribe to our newsletter for updates, a free branding guide and 1-hour training for tech professionals: https://techlegacies.ck.page/newsletter Connect with the podcast host, Fanny Dunagan on LinkedIn at https://www.linkedin.com/in/fannydunagan/Links to the full episode on YouTube, Spotify and Apple Podcasts: https://linktr.ee/techlegacies-------------------------Huge thank you to the sponsors and partners of the #TechLegacies podcast. Hit that FOLLOW button on their pages for the latest updates:🔹 https://www.linkedin.com/company/cginfinity/ - IT Consulting Services, especially in energy and Salesforce🔹 https://www.linkedin.com/in/shaunnablack/ - Executive Coach and & Heart-Centered Leadership🔹 https://www.linkedin.com/company/odyssey-information-services/ - IT recruitment and managed services🔹 https://www.linkedin.com/company/techcxolaunchpad/ - Program to elevate you to senior leadership and C-Suite🔹 https://www.linkedin.com/company/marketscale/ - For your studio recording needs and platform for user content👍 Like, subscribe, and share if this resonated with you

June 2, 20261 hr 4 min

Future of Cybersecurity: Mastercard Executive & Former NSA Leader's Predictions

What is at risk with cybersecurity, now and into the future?In this episode, Tech Legacies Host, Fanny Dunagan sits down with Jon Brickey, SVP at Mastercard and former NSA leader, to talk about the future of cybersecurity and lessons from military leadership.From discovering his hacking instincts as a kid on a TRS-80, to leading cyber strategy at the NSA post-9/11, to building an elite team that Fortune 500 leader calls "the best training I've ever received" — Jon's journey is a masterclass in leadership, resilience, and staying ahead of digital threats.In this episode, you'll learn:🔐 Why cyber is now the 5th domain of warfare — and what it means for every business🪖 The military leadership principle ("leaders eat last") that transformed Jon's management style🤖 Why AI gives hackers a dangerous edge — and how elite defenders are fighting back🧠 The "mood of zeal" framework that replaced fear with passion in their cybersecurity team💼 Career advice for every stage — from hands on analyst to executive cybersecurity leaderWhether you're a tech professional, aspiring executive, or curious about the invisible war being fought online every day — this conversation will change how you think about cybersecurity and leadership.-----------------------------Connect with Jon Brickey on LinkedIn at https://www.linkedin.com/in/drjonbrickey/Want to build your authority and brand as a tech leader? Subscribe to our newsletter for updates, a free branding guide and 1-hour training for tech professionals: https://techlegacies.ck.page/newsletter Connect with the podcast host, Fanny Dunagan on LinkedIn at https://www.linkedin.com/in/fannydunagan/Links to the full episode on YouTube, Spotify and Apple Podcasts: https://linktr.ee/techlegacies-------------------------Huge thank you to the sponsors and partners of the #TechLegacies podcast. Hit that FOLLOW button on their pages for the latest updates:🔹 https://www.linkedin.com/company/cginfinity/ - IT Consulting Services, especially in energy and Salesforce🔹 https://www.linkedin.com/in/shaunnablack/ - Executive Coach and & Heart-Centered Leadership🔹 https://www.linkedin.com/company/odyssey-information-services/ - IT recruitment and managed services🔹 https://www.linkedin.com/company/techcxolaunchpad/ - Program to elevate you to senior leadership and C-Suite🔹 https://www.linkedin.com/company/marketscale/ - For your studio recording needs and platform for user content👍 Like, subscribe, and share if this resonated with you

May 28, 20262 min

The One AI Skill That Makes You Irreplaceable | E02f

Artificial intelligence is transforming how businesses operate but it doesn’t have to make people obsolete.In this segment of Tech Legacies, Ben Coan, Managing Director & Head of Managed Services at Odyssey Information Services, shares practical advice for both employees and employers navigating the AI era.Ben explains why the best professionals won’t resist AI, they’ll learn how to use it to become more valuable. Instead of fearing replacement, tech professionals should embrace AI tools, improve their workflows, and help their organizations adapt.At the same time, leaders need to recognize and retain the people who evolve with technology. After all, businesses are still built on relationships, collaboration, and human insight. Those are things AI can’t replace.Ben also highlights an overlooked challenge many companies face today: legacy systems and undocumented processes. Without proper documentation, training, and knowledge transfer, organizations risk losing critical operational knowledge as experienced workers retire.In this conversation, you’ll learn:Why learning AI is key to staying valuable in your careerHow leaders should support employees adapting to AIThe hidden risk of legacy systems and undocumented processesWhy human relationships still drive business success even in the AI eraIf you're a tech professional, CIO, or business leader, this discussion offers practical insight on how to adapt, evolve, and stay relevant as AI reshapes the workplace.👍 Subscribe for more conversations on technology leadership, careers in tech, and the human side of innovation from Tech Legacies.-----------------------------Connect with Odyssey Information Services on LinkedIn at https://www.linkedin.com/company/odyssey-information-services/ Want to build your authority and brand as a tech leader? Subscribe to our newsletter for updates, a free branding guide and 1hour training for tech professionals: https://techlegacies.ck.page/newsletterConnect with the podcast host, Fanny Dunagan on LinkedIn at https://www.linkedin.com/in/fannydunagan/🎧 Listen on your favorite podcast platformApple Podcasts: https://podcasts.apple.com/us/podcast/tech-legacies/id1704049511Spotify: https://open.spotify.com/show/461kEaQZGqHoAl1nv3W4qe?si=99210e2bad89449aTech Legacies Socials: Instagram: https://www.instagram.com/techlegacies/TikTok: https://www.tiktok.com/@tech_legaciesFacebook: https://www.facebook.com/techlegaciesWork with our podcast team at PathLynks: https://www.linkedin.com/company/pathlynks-llc/👍 Like, subscribe, and share if this resonated with you

May 25, 202611 min

The Sourcing Strategy That Gets People Hired (Not Applications) | E02e

Submitting 257 applications and hearing crickets? You're doing it wrong.In this segment of Tech Legacies, host Fanny Dunagan sits down with the team from Odyssey Information Services, Kristin Hughes (2021 SourceCon Grand Master Challenge Winner), Jon Hibbs, and Ben Coan, to pull back the curtain on how elite recruiters actually find candidates, what's broken in today's job market, and the unconventional moves that get people hired.You'll hear:- What "sourcing" really is and why the best recruiters work more like Sherlock Holmes than HR- The wild story of how Kristin tracked down a software engineer who had hidden every trace of his contact info online- The Home Depot Garden Center hack. How one product manager got into a company's internal job portal by taking a frontline job first- Why AI-written resumes are getting candidates rejected (and the proofreading rule that saves you)- The future of IT, AI, and why human connection is making a comeback- Real leadership lessons from 25+ years of building tech teams- The legacy each leader wants to leave behindIf you're job hunting, hiring, or building a career in tech, this conversation is packed with tactical advice you won't hear anywhere else.-----------------------------Connect with Odyssey Information Services on LinkedIn at https://www.linkedin.com/company/odyssey-information-services/ Want to build your authority and brand as a tech leader? Subscribe to our newsletter for updates, a free branding guide and 1hour training for tech professionals: https://techlegacies.ck.page/newsletterConnect with the podcast host, Fanny Dunagan on LinkedIn at https://www.linkedin.com/in/fannydunagan/🎧 Listen on your favorite podcast platformApple Podcasts: https://podcasts.apple.com/us/podcast/tech-legacies/id1704049511Spotify: https://open.spotify.com/show/461kEaQZGqHoAl1nv3W4qe?si=99210e2bad89449aTech Legacies Socials:Instagram: https://www.instagram.com/techlegacies/TikTok: https://www.tiktok.com/@tech_legaciesFacebook: https://www.facebook.com/techlegaciesWork with our podcast team at PathLynks: https://www.linkedin.com/company/pathlynks-llc/👍 Like, subscribe, and share if this resonated with you

May 21, 20263 min

The Job Search Mistake Recruiters See Every Day | E02d

Sending hundreds of job applications and hearing nothing back can feel frustrating and discouraging. But according to recruiters, that strategy may actually be part of the problem.In this segment of Tech Legacies Podcast, Kristin Hughes, Director of Recruiting, shares practical advice for candidates navigating today’s competitive job market.Kristin explains why the old strategy of applying everywhere often leads to burnout and disappointment. Instead, candidates should focus on intentional, targeted outreach, getting clear on their “why,” researching companies they truly want to work for, and finding creative ways to stand out.She also shares a memorable story about a product manager who struggled to get interviews for months. Rather than giving up, she took an unconventional step that ultimately helped her get noticed by the company she wanted to work for.In this conversation, you’ll learn:Why applying to hundreds of jobs can actually hurt your chancesHow to target the right companies and rolesWhy using AI tools carefully can help in your job searchCreative ways to stand out in a crowded hiring marketIf you’re a tech professional, job seeker, or career changer, this discussion offers fresh perspective on how to approach your job search with more intention and creativity.👍 Subscribe for more conversations on careers in technology, leadership insights, and the human side of tech from Tech Legacies.-----------------------------Connect with Odyssey Information Services on LinkedIn at https://www.linkedin.com/company/odyssey-information-services/ Want to build your authority and brand as a tech leader? Subscribe to our newsletter for updates, a free branding guide and 1hour training for tech professionals: https://techlegacies.ck.page/newsletterConnect with the podcast host, Fanny Dunagan on LinkedIn at https://www.linkedin.com/in/fannydunagan/🎧 Listen on your favorite podcast platformApple Podcasts: https://podcasts.apple.com/us/podcast/tech-legacies/id1704049511Spotify: https://open.spotify.com/show/461kEaQZGqHoAl1nv3W4qe?si=99210e2bad89449aTech Legacies Socials: Instagram: https://www.instagram.com/techlegacies/TikTok: https://www.tiktok.com/@tech_legaciesFacebook: https://www.facebook.com/techlegaciesWork with our podcast team at PathLynks: https://www.linkedin.com/company/pathlynks-llc/👍 Like, subscribe, and share if this resonated with you

May 18, 202615 min

Why Employees Stay 25+ Years at This Company (And Why AI Can't Replace Them) | E02b

What does it take to build a company where people stay for 18, 25, even 30+ years? In this segment, Odyssey founder Jon Hibbs sits down with longtime team members Ben Coan and Kristin Hughes to reveal the leadership philosophy behind one of the staffing and managed services industry's most loyal teams, and why human trust still wins in an AI-driven world.We dig into:Why Odyssey eliminated sales territories (and what happened next)How treating every role like "your own business" drives entrepreneurial ownershipThe team-based delivery model that turned a single consultant into a full managed services engagement with a Fortune 10 retail pharmacyThe simple Friday email habit that builds candidate trust for a decadeWhy AI can find resumes, but can't replace relationshipsThe legacy documentation crisis quietly threatening 75% of enterprise companiesBen's blunt advice for employers: hold onto the people who got you thereWhether you're a CEO building culture, a recruiter navigating an AI-flooded market, or a professional wondering what makes a workplace worth staying at. This conversation is full of practical wisdom from leaders who've actually done it.-----------------------------Connect with Odyssey Information Services on LinkedIn at https://www.linkedin.com/company/odyssey-information-services/ Want to build your authority and brand as a tech leader? Subscribe to our newsletter for updates, a free branding guide and 1hour training for tech professionals: https://techlegacies.ck.page/newsletterConnect with the podcast host, Fanny Dunagan on LinkedIn at https://www.linkedin.com/in/fannydunagan/🎧 Listen on your favorite podcast platformApple Podcasts: https://podcasts.apple.com/us/podcast/tech-legacies/id1704049511Spotify: https://open.spotify.com/show/461kEaQZGqHoAl1nv3W4qe?si=99210e2bad89449aTech Legacies Socials: Instagram: https://www.instagram.com/techlegacies/TikTok: https://www.tiktok.com/@tech_legaciesFacebook: https://www.facebook.com/techlegaciesWork with our podcast team at PathLynks: https://www.linkedin.com/company/pathlynks-llc/👍 Like, subscribe, and share if this resonated with you

May 14, 20263 min

What is IT Managed Services? And Why Smart Companies Are Using It | E02b

Many companies today are not actually in the business of IT, yet IT ends up consuming enormous time, money, and leadership attention.In this segment of Tech Legacies, Ben Coan, Managing Director & Head of Managed Services at Odyssey Information Services, explains how managed services help organizations shift their focus back to what matters most: running and growing their core business.Ben shares how many companies struggle with fragmented IT environments where infrastructure, applications, and database teams don’t communicate effectively. Managed services create a team-based support model that fills gaps, improves collaboration, and provides experienced experts behind the scenes.Instead of relying on a single consultant, organizations gain access to an entire bench of trusted specialists who can support operations, identify risks, and strengthen IT systems over the long term.In this conversation, you’ll learn:Why many companies get pulled away from their core business by IT complexityWhat managed services actually mean beyond traditional IT supportHow a team-based delivery model helps close technology gapsWhy trust and long-term relationships are essential in managed services partnershipsIf you're a CIO, IT leader, or business executive, this conversation will help you rethink how IT support can evolve from a burden into a strategic advantage.👍 Subscribe for more conversations on careers in technology, leadership insights, and the human side of tech from Tech Legacies.______________________Connect with Odyssey Information Services on LinkedIn at https://www.linkedin.com/company/odyssey-information-services/ Want to build your authority and brand as a tech leader? Subscribe to our newsletter for updates, a free branding guide and 1hour training for tech professionals: https://techlegacies.ck.page/newsletterConnect with the podcast host, Fanny Dunagan on LinkedIn at https://www.linkedin.com/in/fannydunagan/🎧 Listen on your favorite podcast platformApple Podcasts: https://podcasts.apple.com/us/podcast/tech-legacies/id1704049511Spotify: https://open.spotify.com/show/461kEaQZGqHoAl1nv3W4qe?si=99210e2bad89449aTech Legacies Socials: Instagram: https://www.instagram.com/techlegacies/TikTok: https://www.tiktok.com/@tech_legaciesFacebook: https://www.facebook.com/techlegaciesWork with our podcast team at PathLynks: https://www.linkedin.com/company/pathlynks-llc/👍 Like, subscribe, and share if this resonated with you

May 11, 202613 min

Microsoft, Meta & Amazon Layoffs: What's Really Happening to Tech Jobs in 2026 | E02a

Microsoft. Dell. Meta. Salesforce. Amazon just cut 16,000 white-collar jobs.The headlines scream AI layoffs. But what's REALLY happening behind the scenes in tech hiring?In this candid roundtable, three industry insiders pull back the curtain on the 2026 tech job market:🔹 Kristin Hughes reveals what's actually getting hired (and why "post and pray" job hunting is dead)🔹 Ben Coan exposes the sleeper opportunities most candidates are missing, including the legacy tech crisis that could be your goldmine🔹 Jon Hibbs shares what's keeping CIOs awake at night and the 3 pressures shaping every hiring decisionWhether you're a job seeker drowning in rejection emails, an employer trying to build the right team, or a tech professional planning your next move. This conversation will change how you think about the AI disruption.💡 You'll learn:✅ Which roles are still hiring (and which are quietly dying)✅ The unexpected "trade jobs" boom inside the AI revolution✅ Why legacy systems = job security in disguise✅ The video reference trick that's landing offers in this market✅ How managed services is reshaping IT employment-----------------------------Connect with Odyssey Information Services on LinkedIn at https://www.linkedin.com/company/odyssey-information-services/ Want to build your authority and brand as a tech leader? Subscribe to our newsletter for updates, a free branding guide and 1hour training for tech professionals: https://techlegacies.ck.page/newsletterConnect with the podcast host, Fanny Dunagan on LinkedIn at https://www.linkedin.com/in/fannydunagan/🎧 Listen on your favorite podcast platformApple Podcasts: https://podcasts.apple.com/us/podcast/tech-legacies/id1704049511Spotify: https://open.spotify.com/show/461kEaQZGqHoAl1nv3W4qe?si=99210e2bad89449aTech Legacies Socials:Instagram: https://www.instagram.com/techlegacies/TikTok: https://www.tiktok.com/@tech_legaciesFacebook: https://www.facebook.com/techlegaciesWork with our podcast team at PathLynks: https://www.linkedin.com/company/pathlynks-llc/👍 Like, subscribe, and share if this resonated with you

May 4, 202652 min

Mastering Job Search Amongst AI Layoffs

AI is replacing jobs. Tech layoffs are making headlines. So why do the most successful tech companies say relationships matter MORE than ever? In this episode of Tech Legacies, host Fanny Dunagan sits down with the team from Odyssey Information Services: Jon Hibbs (CEO), Kristin Hughes (Director of Recruiting), and Ben Cohen (Managing Director of Managed Services) to unpack what's really happening in the tech job market and what it takes to build a 25-year company on trust. What you'll learn in this episode: The truth behind the AI layoffs: what's actually being cut and what's still hiring strong Why "post and pray" is officially dead for both job seekers AND employers The #1 thing CIOs say keeps them up at night What "managed services" really means and why more companies are turning to it The overlooked tech opportunity almost no one is talking about 3 actionable job search tips from a recruiter who's seen it all How Odyssey built a culture where top talent stays for 18–25 years (and why that's rare) Whether you're a tech leader navigating transformation, a job seeker trying to stand out in a crowded market, or a business owner wondering how to scale your IT without losing your focus, this conversation has something for you. ----------------------------- Connect with Odyssey Information Services on LinkedIn at / odyssey-information-services Want to build your authority and brand as a tech leader? Subscribe to our newsletter for updates, a free branding guide and 1-hour training for tech professionals: https://techlegacies.ck.page/newsletter Connect with the podcast host, Fanny Dunagan on LinkedIn at / fannydunagan 🎧 Listen on your favorite podcast platform Apple Podcasts: https://bit.ly/4kr4wpi Spotify: https://bit.ly/3Mo11mN Tech Legacies Socials: Instagram: / techlegacies TikTok: / tech_legacies Facebook: / techlegacies Work with our podcast team at PathLynks: / pathlynks-llc 👍 Like, subscribe, and share if this resonated with you

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