Keeping IT Real | Technology | Business

Keeping IT Real | Technology | Business

Welcome to the original Keeping IT Real podcast. IT is not what it used to be. This podcast features honest and transparent conversations about what it takes to manage corporate technology and expenses today. Each episode, listen to true and personal stories from IT professionals who are working hard to make sure their business stays connected and competitive. Note: Previously known as Braindrop. Topics: IT Leadership IT Management IT Managed Services IT Operations IT Trends AI Telecom, Mobile, Cloud Managed Mobility Services Telecom Expense Management Digital Transformation Communications

Episodes

June 24, 2025 36 mins

On this episode of Keeping IT Real, Jethro Castillo is joined by Taruna Rai, a VP of IT. Taruna discusses her non-traditional path into IT, emphasizing her passion for connecting technology to business outcomes. She sheds light on the evolving role of IT from being an order taker to a strategic business partner, and the importance of maintaining a growth mindset in a fast-paced industry. Taruna also touches on the significance of b...

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On this episode of Keeping IT Real, Jethro Castillo is joined by Elliott Adler, the Director of IT at MedRite Urgent Care. Elliott shares his journey into the IT world, from childhood fascination to leading digital transformations in healthcare. The discussion covers the evolution of technology, the challenges of maintaining cybersecurity, and the importance of communication and teamwork. Elliott reveals how his team balances innov...

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May 27, 2025 34 mins

On this episode of Keeping IT Real, Jethro Castillo is joined by Gavin Hupp, a VP of Technology. Gavin shares his unconventional journey from studying clinical exercise physiology to becoming a seasoned technology executive. He highlights his experience in various roles, from running an e-commerce business to leading digital transformations at companies like Denny's, PetSmart, and now United Parks and Resorts (SeaWorld). Gavin prov...

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On this episode of Keeping IT Real, Jethro Castillo is joined by Obinna Amalu, the Senior Director of IT Ops and Infrastructure at Slalom. Obinna, who has over 20 years of experience focusing on edge computing, AI, and team empowerment, shares his journey into IT, starting from helping his mother’s computer training business to significant roles in various sectors in the United States. He discusses the excitement and concerns of ad...

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On this episode of Keeping IT Real, Jethro Castillo is joined by Nicholi Gray, the IT Service Director at Nikola Motor Company. Nicholi shares his unique journey into the world of IT, from helping his father's business to pivotal roles at Romeo Power and Nikola. He discusses the excitement and challenges of constant change in the tech industry, the importance of adaptability, and the human side of managing technology. Nicholi h...

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On this episode of Keeping IT Real, Jethro Castillo is joined by Adam Gruszcynski, the Director of IT at Potawatomi Casino Hotel. Returning for a second time, Adam provides an in-depth catch-up on the multitude of projects and innovations undertaken over the past year and a half, including a $190 million casino renovation, the introduction of new dining concepts like Rock & Brews with KISS members Gene Simmons and Paul Stanley,...

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On this episode of Keeping IT Real, Jethro Castillo is joined by Greg Jacoby, the CEO and Founder at Bright Development, a boutique development agency dedicated to helping businesses create impactful digital experiences. Greg shares his extensive experience in web development and digital strategy, and discusses his journey from frustration with vendor relationships to creating a more honest and supportive agency environment. The co...

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On this episode of Keeping IT Real, Jethro Castillo is joined by Nitzan Eini, a Director of Enterprise Application Services and Operations. Nitzan talks about his extensive journey in the IT world, offering insights into his early days as a junior IT engineer to his current role leading global teams. They discuss the critical importance of balancing day-to-day maintenance with room for innovation, the challenges of scalability and ...

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On this episode of Keeping IT Real, Jethro Castillo is joined by James Ordinans, an Executive Director of IT.

James shares his unconventional journey from financial services to IT leadership, revealing how his background in finance provided a unique edge in optimizing technology systems. The conversation explores the challenges and rewards of managing IT in diverse industries, the evolution of IT from 'order taker' to 'business par...

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On this episode of Keeping IT Real, Jethro Castillo is joined by Scott Lee, the Associate Vice President and Head of IT Infrastructure & Operations at Arch Mortgage Insurance Company (Arch MI). Scott shares his journey into IT, starting from a love of video games to his extensive experience in infrastructure and operations. The conversation covers technological advancements, the importance of infrastructure in IT, and strategie...

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On this episode of Keeping IT Real, Jethro Castillo is joined by Kelenda Allen-James, an Assistant Vice President Of Information Technology. Kelenda shares her journey in IT, her commitment to helping underserved communities through affordable technology solutions, and her dedication to promoting diversity in tech. They discuss her initiatives like Study Hall with Kelenda, her concerns about AI bias, and her holistic approach to in...

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In this episode of Keeping IT Real, host Jethro Castillo chats with Renato Inacio, Director of IT Operations at Child Mind Institute. Renato shares his unique journey from aspiring lawyer to becoming a passionate IT leader. They explore the rapid pace of technological change, the importance of continuous learning, and the challenges of managing IT within budget constraints. Renato also highlights the significance of internal traini...

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On this episode of Keeping IT Real, Jethro Castillo speaks with Kurt Moreno, Director of IT Services with over 20 years of experience. Kurt shares his career journey from CAD drafting in high school to leading IT teams, and provides insights into the strategic initiatives he's managed throughout his career. They discuss the challenges and shifts that come with corporate acquisitions, the importance of communication and soft skills ...

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On this episode of Keeping IT Real, Jethro Castillo sits down with Jason Fowler, the Director of IT at Playa Bowls, an acai shop with over a hundred locations worldwide. Jason shares his unique journey from working in the entertainment and restaurant industries to leading IT at Pliables. He discusses the importance of blending technology with customer experience, how he approaches IT challenges, the value of partnerships with vendo...

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On this episode of Keeping IT Real, Jethro Castillo is joined by Dr. Aaron Hill, the Executive Director of IT Support at Fontainebleau Las Vegas. Dr. Hill shares his unconventional career path, including 23 years in the US Marine Corps and various roles in retail distribution, e-commerce, environmental startups, and government consulting. Listen to his insights on adapting to different industries, demonstrating capabilities ahead o...

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November 26, 2024 34 mins

On this episode of Keeping IT Real, Jethro Castillo is joined by Puneet Bhargava, a Sr. Director of IT with over 15 years of experience. Puneet shares his journey from his early fascination with programming to leading large-scale IT transformations. He provides insight into driving impactful results, overcoming challenges in technology adoption, and the importance of strategic planning in managing corporate technology and expenses....

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On this episode of Keeping IT Real, Jethro Castillo sits down with Aaron Rezepka, the Senior Director of IT Service Delivery for the NFL. With over 25 years of IT experience, Aaron shares his journey from growing up around technology to managing IT for one of the world's most beloved sports leagues. Aaron discusses the challenges and innovations in NFL IT, including the use of AI, security measures, and the automation of onboarding...

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On this episode of Keeping IT Real, Jethro Castillo is joined by Geetha Kommepalli, a seasoned VP of Digital and IT with over 20 years of experience. Geetha shares her journey from computer applications to leading multi-billion-dollar mergers and acquisitions. Geetha also highlights strategies on how to successfully deal with mergers and acquisitions on the IT side. Discover the evolving role of IT in balancing innovation with secu...

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October 15, 2024 35 mins

On this episode of Keeping IT Real, Jethro Castillo is joined by Mitch Cullins, a Director of IT. Mitch discusses the impact of AI in daily IT operations, security concerns, and the importance of aligning IT efforts with strategic business goals. He highlights significant career projects, such as the creation of a Fortune 500 company from scratch, emphasizing the challenges and triumphs experienced in his role. Mitch also touches o...

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On this episode of Keeping IT Real, Jethro Castillo is joined by Joseph Silva, the IT Director of Data & Governance, Risk, and Compliance at Kelly-Moore Paints. Joe shares his 20-year journey in the IT and cybersecurity space, and talks about what it's like managing IT during a company shutdown, highlighting the significance of identity automation, data security, and maintaining compliance.

You can find Joseph Silva here: https...

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