The Tech Trek

What does it take to build and scale AI responsibly inside a major media organization? In this episode, Amir sits down with Arvind Thinagarajan, formerly Head of Enterprise Data Science & Analytics at Gannett (publisher of USA Today), to unpack how they built a volunteer-driven AI Council that governs, guides, and accelerates AI initiatives across the company. From prioritization frameworks to...

What does it take to build AI systems that are private by design—and ready for tomorrow’s regulations? In this episode, I’m joined by Rishabh Poddar, CTO and Co-founder of Opaque Systems, to explore how data privacy, compliance, and AI innovation intersect in a rapidly evolving landscape. Rishabh breaks down the impact of emerging privacy laws, the risks with agentic AI systems, and why building c...

What happens when a data-driven founder leaves Big Tech to tackle a broken healthcare system? In this episode of The Tech Trek, Amir sits down with Tim Edgar, Co-founder and CTO at Venteur, to unpack how deep personal insight, emotional connection, and data all play a role in identifying real-world problems worth solving. From launching Bing under Satya Nadella to co-founding companies with his si...

In this episode of The Tech Trek, Amir sits down with Davy Li, Head of Engineering at Mesa, a startup redefining how homeowners earn rewards on everyday home expenses. Davy shares his personal journey from Big Tech to startup life, unpacks how he’s built Mesa’s engineering team from scratch, and offers a refreshingly candid look at what it means to be an effective leader in a small but growing org...

In this candid conversation, Bryan Mahoney unpacks his journey from CTO to CEO, exploring what it really takes to evolve beyond the engineering org into leading an entire company. We talk about how his curiosity and hands-on technical skills still shape how he leads today, the mental shifts required to manage AI-driven teams, and how leadership demands evolve as a company scales from services to S...

What does it really take to build company culture from the ground up—especially when you’ve done it more than once? In this episode, Amir sits down with Darren Nix, founder and CEO of Steadily Insurance, to talk about the wins and missteps that come with building startups. Darren shares what’s stayed the same (and what hasn’t) across the four companies he’s founded, and why being deliberate about...

In this episode, Amir sits down with Jay Vijayan, Founder and CEO of Tekion, to explore how digital transformation and AI are modernizing the automotive retail industry. They dive deep into the complexities of dealership systems, the supply chain ripple effects of tariffs, and the evolving consumer experience. Jay explains why legacy systems can't meet today’s expectations and how Tekion is bu...

In this episode of The Tech Trek , Amir sits down with Reed McGinley-Stempel , co-founder and CEO of Stytch , to explore what it means for applications to be agent ready . With the rise of agentic AI—intelligent systems that can take actions on behalf of users—the landscape for SaaS and consumer-facing apps is rapidly evolving. Reed breaks down the core concepts around agent integration, including...

In this episode, Amir chats with Jason Fellin, Head of Growth Engineering at OnX Maps, to unpack what makes growth engineering unique. Jason shares how his team focuses on speed, experimentation, and measurable business impact rather than long-term architecture. From hiring strategies to cross-functional collaboration with marketing, this conversation offers a tactical look at building and leading...

In this episode, Amir sits down with Brooke Motta, CEO and co-founder of RAD Security, to unpack her career pivot from sales leadership to becoming a founder in the cybersecurity space. Brooke shares how her go-to-market background shaped her approach to building RAD, the challenge of stepping into technical leadership, how she’s managing growth through hiring, and what’s ahead for security and AI...

In this episode, Richard Girges, CTO at MNTN, breaks down the appeal and risk of emulating high-profile leaders like Elon Musk or Steve Jobs. From startup life to scaling teams, Richard shares how leaders can avoid the missteps of mimicry and instead cultivate their unique "mode of genius." You’ll learn how intuition, failure, and self-awareness play a vital role in effective leadership—...

In this episode, Amir sits down with Brian McMahon, CEO and co-founder of Pickle—a fashion rental marketplace aiming to become the Airbnb for everyday items. Brian unpacks how Pickle solved the classic two-sided marketplace dilemma, why hyperlocal supply is their secret weapon, and how AI is powering everything from product tagging to customer support. They also dive into the evolution of Pickle’s...

In this episode, Amir sits down with Aaron Painter, CEO of Nametag, to explore how deepfakes and generative AI are reshaping identity security in the workplace. They discuss real-world attacks, such as the MGM breach, and how enterprises are responding with new technologies—from cryptographic identity verification to re-verification protocols. Aaron shares what companies are doing right, where the...

In this episode, Amir speaks with Anna Patterson, founder of Ceramic AI, about what it truly means to lead an AI-first company. They unpack the differences between engineering and AI leadership, the chaos and creativity of early-stage research, how Ceramic AI is betting on emerging talent, and why managing AI roadmaps is an exercise in uncertainty and invention. Anna also shares perspectives from...

In this episode of The Tech Trek, Amir sits down with Matt Moore, CTO and co-founder of Chainguard, to explore the escalating importance of software supply chain security. From Chainguard’s origin story at Google to the systemic risks enterprises face when consuming open source, Matt shares the lessons, best practices, and technical innovations that help make open source software safer and more re...

In this episode of The Tech Trek, Christina Garcia, SVP of Engineering at Echo Global Logistics, shares her insights on integrating AI not as a replacement but as a partner in business operations. We unpack how organizations can holistically rethink processes, overcome adoption hurdles, and empower innovators inside the company to co-create AI use cases. Christina also opens up about the unique le...

In this episode, Amir sits down with Anthony Jules, Co-Founder and CEO of Robust. AI, to explore how scaling lessons from the early days of Sapient translate into today’s rapidly evolving world of AI and robotics. Anthony shares stories from growing a company from 3 to 4,000 people, what scale teaches you about communication and change, and how being ruthlessly honest about your business creates s...

In this episode of The Tech Trek, Amir sits down with Joe Philleo, founder and CEO of Edio, an AI platform transforming K-12 education. Joe shares his journey from building websites in high school to writing a viral essay on Palantir that kickstarted his tech career. He dives into the critical role AI now plays in solving chronic absenteeism and driving measurable academic improvements. The conver...

In this episode of The Tech Trek , Amir sits down with Sus Misra , SVP of Data & Analytics at Solve(D) (IPG Health), to unpack what true precision targeting looks like in one of the most regulated industries: pharma. Sus explains how healthcare marketers uniquely leverage individual-level data to connect with professionals like doctors and oncologists—something unheard of in most sectors. But...

In this episode of The Tech Trek, Brian Clifford, Chief Data Officer at Amica Insurance, shares how his team translates core company values—like exceptional customer service—into actionable AI and data strategies. We explore how Amica approaches pilots, vendor selection, internal adoption, and governance to scale AI effectively and responsibly. 🔑 Key Takeaways: Value-Driven Data Strategy: Amica a...

In this deep-dive episode, we explore what it truly means to be "AI-native" versus bolting AI onto existing products. Abhay Mitra, CTO of Nirvana Insurance, shares how his team is building industry-specific AI models to transform the $800B+ commercial insurance market, starting with trucking—one of the most complex and painful sectors in insurance. From telematics data platforms to fine-...

In this episode, we dive deep into the evolving relationship between engineering and product with Pranab Krishnan, CTO of Zeal - a payroll and payments platform for staffing companies. We explore how the traditional boundaries between engineering, product management, and customer interaction are dissolving, especially in the age of AI. Pranab shares insights on building a product-centric engineeri...

In this episode of The Tech Trek, Vinayak Kumar shares how his team at Lynx strikes a practical balance between innovation and efficiency in the heavily regulated healthcare and finance space. He explains why innovation shouldn’t be forced, how to avoid the "tech in search of a problem" trap, and why pattern-driven execution helps startups scale faster without compromising flexibility. 🔑 Key Take...

In this episode, Amir speaks with Ameya Brid, Global Director of Data & Analytics at Invista, about the maturation of GenAI conversations in the enterprise. They dive into the shift from hype to implementation, real-world challenges like data quality and change management, and how composable architecture is helping organizations adapt to rapid innovation cycles. 🔑 Key Takeaways From Hype to V...

In this episode of The Tech Trek, Amir sits down with Andy Beam, CTO of Lila Sciences, to explore how AI is transforming the messy, serendipitous nature of scientific discovery into an engineered, scalable process. From automating lab work to accelerating the speed of breakthroughs, Andy explains why the future of science may be less about eureka moments and more about AI-driven iteration. 🔑 Key...