The Tech Trek

Allan Leinwand, CTO at Webflow, joins me to explore how AI is reshaping engineering workflows, from code generation to team structure. We dig into how AI tools are boosting productivity, enabling faster onboarding for junior engineers, and freeing up senior talent to focus on distributed systems and business-critical challenges. Allan shares real examples of automation in action, how his team meas...

Nikola Borisov, CEO and co-founder of Deep Infra, joins the show to unpack the rapid evolution of AI inference, the hardware race powering it, and how startups can actually keep up without burning out. From open source breakthroughs to the business realities of model selection, Nikola shares why speed, efficiency, and strategic focus matter more than ever. If you’re building in AI, this conversati...

Zach Lloyd, CEO and founder of Warp, joins The Tech Trek to unpack what it really takes to build tools that transform the developer experience. From rethinking the terminal to balancing product focus with user growth, Zach shares hard-earned lessons from scaling products that developers actually want to use. This is a conversation about building with empathy, understanding workflows, and making de...

Sek Chai, CTO and cofounder of Latent AI, joins The Tech Trek to talk about what it actually takes to get AI running on the edge. We explore the real-world constraints of power, compute, and hardware diversity, why an agent-assisted workflow can accelerate MLOps, and how to choose models that are good enough to ship. Sek also breaks down lessons from selling into the federal market and explains wh...

Berit Hoffmann, CEO and co-founder of Korl, joins The Tech Trek to share her candid journey from big tech leader to late-stage startup founder. With a resume that includes Google, Dell, and Sisu, Berit could have landed any top role—but she chose the riskier path of building her own AI company while raising two kids and fundraising while seven months pregnant. In this episode, she opens up about t...

What does it take to lead analytics at a truly global scale? In this episode, Amir sits down with Anant Veeravalli, Global Chief Data and Analytics Officer at Media Brands (part of IPG), to unpack how he built and scaled a Center of Excellence (COE) that spans regions, brands, and disciplines. Anant shares the real-world challenges of aligning thousands of data professionals under one strategic vi...

What if your phone didn’t need to hold your data at all? In this episode of The Tech Trek, Amir sits down with Jared Shepard, CEO of Hypori, to explore how virtualization at the edge is transforming security, mobility, and data ownership. Jared breaks down Hypori’s secure virtual mobile OS, originally built for the Department of Defense, and how it’s now entering the enterprise and consumer spaces...

Feross Aboukhadijeh, founder and CEO of Socket, joins The Tech Trek to pull back the curtain on software supply chain security, why legacy tools are failing, and what it really takes to build trust into modern development. Feross explains how Socket is tackling vulnerabilities most vendors can't even detect and shares why they made a rare early-stage acquisition—and how it’s reshaping their ro...

What does it take to deliver innovation at just the right moment? In this episode of The Tech Trek, Amir sits down with Eric Hoffert, CTO at Kargo and former video leader at Apple and Spotify, to unpack the art and science of innovation timing. From building QuickTime at Apple to launching video at Spotify a decade before the market caught up, Eric shares stories that blend conviction, timing, and...

What if your infrastructure could predict demand before it happens? In this episode, Nilo Rahmani, CEO and co-founder of Thoras AI, breaks down how predictive scaling is transforming the Kubernetes landscape. With over a decade of experience in site reliability engineering, Nilo shares why the observability market is slower to adopt AI—and why that might finally be changing. If you're navigati...

What happens when UX design collides with generative AI? In this episode of The Tech Trek, Amir sits down with Mickey Alon, CEO and co-founder of Eucera, to explore how AI-first design is redefining SaaS product experiences. Mickey shares his vision for conversational UX, why menus are becoming obsolete, and how intelligent agents will soon become the most valuable “team member” in your product. I...

How do we ship code faster without sacrificing quality or accountability? Greg Foster, co-founder and CTO at Graphite, joins the show to unpack how AI is reshaping code reviews, developer workflows, and the very definition of software engineering. From AI-assisted reviews to the challenge of maintaining context in a world of auto-generated code, Greg shares hard-won insights from the front lines o...

What does it take to build startups that last and come back for more? In this episode, Amir sits down with Russ Fradin, serial founder, longtime investor, and now CEO of Larridn. With nearly 30 years of experience and billions raised across multiple ventures, Russ shares what he’s learned about founding companies, hiring the right people, navigating pivots, and representing other people’s money wi...

What do founders get wrong when trying to build a startup? Jeff Gibson, CTO and co-founder at Kintsugi, joins the show to break down how he approaches building around real business problems—not flashy features. Drawing from pre-IPO roles at Atlassian and his journey scaling Kintsugi, Jeff shares why understanding cash flow, revenue mechanics, and operational bottlenecks is critical for building so...

Ashok Srinivasan, SVP of Engineering at Aledade, joins The Tech Trek to break down what it really means to have impact as an engineering leader. With experience at Microsoft, Snapchat, Indeed, Dropbox, and now Aledade, Ashok brings clarity on how to assess your value, earn trust, and align technical strategy to business outcomes. Whether you're leading at a scrappy startup or an enterprise gia...

Vijaye Raji, CEO and founder of Statsig, left two decades of success at Microsoft and Facebook to start from scratch—at age 41. In this episode of The Tech Trek, we unpack the mindset, planning, and trade-offs that come with becoming a first-time founder later in life. If you've ever wondered what it really takes to leave the safety of big tech to chase a startup dream, this one’s for you. Wha...

What if your data science team could drive business outcomes across products, not just models? In this episode, Hicham El-Hassani shares a tested blueprint for building data teams that are adaptable, retention-proof, and ready to ship. With 18 years of experience, Hicham has led high-impact data science orgs across insurance and software—and he’s not afraid to challenge the standard playbook. He e...

What does the “long tail” of AI really look like in a highly regulated industry? In this episode, Dave Wollenberg, VP of Enterprise Data & Analytics at Scan, breaks it down. From cautious experimentation to enabling non-technical users to build AI-driven POCs, Dave shares a grounded, practical perspective on AI adoption inside a Medicare Advantage organization. You’ll hear why the real transfo...

What happens when you bring Silicon Valley tech thinking into an “unsexy” industry? Alex Jekowsky, Co-founder and CEO of Cents, shares how his vertically integrated platform is quietly transforming garment care—starting with laundromats. In this conversation, Alex breaks down what it takes to digitize an analog industry, earn operator trust, and build deep value with a lean team. If you’ve ever wo...

How do you turn GenAI excitement into real enterprise value—without leaving people behind? In this episode, Amir talks with Mike Urban, Chief Technology Operations Officer at Best Egg, about the overlooked muscle every company needs to build: change management. Mike shares how his team is navigating the real-world complexity of bringing GenAI into production across a highly regulated fintech org—w...

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...