What happens when a company grows through acquisitions but wants to keep the startup spirit alive?

In this episode, TC Gill sits down with Ed Frederici, CTO at Appfire, to explore how to build harmony in a scaling tech company, without crushing innovation. From preserving entrepreneurial culture to building strong, autonomous teams, this one’s packed with insight.

Episode 178: Creating Harmony in a Scaling Company Fueled by Acquisitions with Ed Federici

From cinematography to the C-suite? Yes, you read that right. In this episode, TC Gill talks with Chris Geiser, CTO at DCG ONE, about an unconventional leadership journey that blends creativity, marketing, and tech strategy.

If you’re into leadership lessons with a personal twist, this one’s for you.

Episode 179: From Cinematography to Strategic Marketing with Chris Geiser

What makes great software truly customer-centric? 

In this week’s episode, Chris Huff, former CTO at Rent Group, joins TC Gill to break down the real secret behind building products that actually serve users. Spoiler: it’s not about adding more features.

Episode 180: The Secret to Great Customer-Centric Software with Chris Huff

What happens when deep technical knowledge meets real-world domain expertise?

In this episode, TC Gill is joined by James Long, CTO at Palomar, to explore what it takes to lead with clarity in a high-stakes environment. From modeling risk to building strong, cross-functional teams, this conversation is packed with practical insights for tech leaders.

If you're looking to sharpen your leadership edge, this episode delivers.

Episode 182: A CTO's Career Guide: Blending Tech and Business with James Long

How can we separate real innovation from hype? 

In this episode, Joel Krooswyk, Federal CTO at GitLab, joins TC Gill for a thoughtful deep dive into the evolving role of AI in development, hiring, and leadership. Joel brings 25+ years of experience across private and public sectors and this conversation hits that perfect balance of vision and pragmatism. 

Tune in now and explore the full story!


Episode 183: An AI Give-and-Take with Joel Krooswyk

Can good leadership be taught or does it come down to who you are?

In this episode, we sit down with Wes Bailey, Founder at Par Not Far, for a refreshingly honest conversation about leadership, bureaucracy, and why some of today’s sacred practices might need to go.

If you’re tired of corporate speak and want something real, this is the episode for you.

Episode 184: Do Good Leaders Get to the Top? A Discussion with Wes Bailey

In this episode of CTO Confessions, we sit down with Reinaldo Ynchaustegui, CTO in the asset management space, for an overview of what it really takes to lead in tech. From dissecting how to automate a tech team’s workflow without losing the human touch to exploring the critical role of emotional intelligence in leadership, Reinaldo shares insights from the frontlines. 

Tune in to hear the realities behind the role and the balance between tech and people.

Episode 185: Leading at the Intersection of Technology and Finance with Reinaldo Ynchaustegui

What can the Marines teach us about leading high-performing tech teams? A lot more than you might think.

In this episode, Bob Hackney, CTO at PerfectServe, shares how a mission-first mindset translates from the battlefield to the boardroom, delivering results without sacrificing your people. His “double win” approach is all about achieving objectives while growing and empowering teams.

Whether you’re scaling a tech org, running global teams, or simply looking to lead with empathy and impact, this conversation will challenge and inspire you.

Episode 186: Lessons from the Marines and Tech with Bob Hackney

Allen Cheung, SVP of Engineering at UJET.cx, sat down with our host TC Gill for our podcast CTO Confessions to explore how AI is reshaping the tech industry and why some programmers resist this transformation.


Whether you’re building teams, navigating the shift to AI-powered engineering, or simply looking to embrace growth through change, this conversation will challenge and inspire you.

Episode 187: Programmers' Resistance in the Age of AI with Allen Cheung

Naresh Singh, Partner and CTO at Lenox Advisors, sat down with our host TC Gill for our podcast CTO Confessions to discuss how technology is reshaping wealth management from AI-driven data systems to leadership grounded in both technical foresight and servant leadership.

Whether you’re navigating financial services, driving transformation through technology, or leading high-performing teams, this conversation will inspire and equip you with practical insights.

Episode 188: Wealth Management Driven by Technology with Naresh Singh

Hosted by TC Gill, this podcast explores the dynamic world of technology leadership. Each episode explores the challenges, strategies, and stories that shape the lives of today’s CTOs and tech leaders.  

From navigating complex business issues to leading high-performing teams, CTO Confessions sheds light on the multifaceted role of technology executives, highlighting the critical decisions they make and the impact they have on organizations.  

Join us as we unpack the realities of tech leadership and share insights that rarely get the appreciation they deserve, all with a healthy dose of curiosity and candor. 

Brought to you by IT Labs.

Episode 184: Do Good Leaders Get to the Top? A Discussion with Wes Bailey

CTO Confessions

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