The Tech Trek

Ogi Kavazovic, co-founder and CEO of House Rx, joins the show to unpack what most product leaders miss about building for enterprise software. Drawing from two decades in tech, Ogi breaks down how product management shifts when you move from B2C or “B to small B” to true enterprise—what he calls “B to Big B.” He explains why traditional user research frameworks don’t hold up, how buyer research sh...

Astasia Myers, General Partner at Felicis, breaks down how venture capital is betting on AI and why over 80% of their recent investments are in this space. But this isn’t just another “AI is the future” conversation. We dig into the real ROI happening right now in healthcare voice agents, why MIT says 95% of GenAI projects fail to reach production, and what needs to happen for that number to flip....

In this episode, Amir sits down with Taofeek Rabiu, VP of Engineering at Etsy, to unpack a distinction that most organizations miss: being a people leader is not the same as being a people manager. If you have ever wondered why some teams thrive under pressure while others crumble, or why trust feels so hard to build in engineering orgs, this conversation has answers. Taofeek shares how leadership...

Ion Feldman, CTO at Rightway, has learned to love one thing about scaling a company from a kitchen table to nearly 1,000 employees: his job completely changes every six months. In this episode, Ion shares what it means to lead engineering when the role refuses to stay still—from writing code in the early days to building product, security, and data teams, and now shaping AI infrastructure. He expl...

Jay Chia, cofounder of Eventual, joins the show to unpack what real empowerment looks like inside a fast growing startup. Most people confuse empowerment with initiative, but Jay explains how trust, vulnerability, and accountability work together to turn good teams into self directed ones. If you are scaling a startup or leading a growing engineering team, this conversation explores the human side...

Rohan Kodialam, cofounder and CEO of Sphinx, is building AI agents that treat data as its own language—one most models and humans still fail to understand. In this episode, he unpacks why data science has lagged behind software engineering, how AI can finally close the gap between business questions and answers, and what happens when small teams gain the analytical power of a thousand person quant...

Karl Alomar, Managing Partner at M13 and former COO of DigitalOcean, joins The Tech Trek to share how being an operator changes the way you invest. He explains why M13 was built to be a truly founder-first VC firm—one that acts early, helps proactively, and builds deep relationships rooted in empathy and experience. From spotting great founders to balancing instinct and data, this episode explores...

In this episode of The Tech Trek, Amir sits down with Michi Kono, CTO of Garner Health, to unpack what it really takes to scale engineering leadership inside a fast growing startup. Michi shares how he balances structure and speed, why formalizing processes too early can slow innovation, and how “the Garner way” blends lessons from big tech with first principles thinking. This is a conversation ab...

Vibe coding isn’t just a new buzzword—it’s a complete shift in how engineering teams build, ship, and think. Zach Wills, Director of Engineering at Luxury Presence, joins to share how his team is rewriting the rules of software delivery using AI-assisted workflows. From Greenfield experiments to Brownfield transformations, Zach breaks down the frameworks, lessons, and mindset shifts reshaping what...

From a farm in Adelaide to the front lines of AI-powered personalization. Tullie Murrell, CEO and co-founder of Shaped, shares how he went from researcher to founder and built a platform helping businesses deliver the kind of intelligent recommendations once reserved for big tech. We explore the mindset shifts, technical leaps, and founder lessons that shaped his path—from Meta’s AI labs to democr...

Jason Eubanks, Co-Founder and CEO of Aurasell, shares the path that led him from a small town in rural Ohio to building one of the most ambitious AI-driven CRM platforms on the market. His journey reveals how limited opportunity can spark relentless ambition and how early lessons in persistence shaped the mindset of a founder willing to take on giants. Key Takeaways • A clear purpose often starts...

Some companies thrive while others quietly lose their edge. For Tanay Kothari, CEO of Wispr Flow, the difference comes down to one idea: people are your responsibility. In this conversation, Tanay shares how that realization changed everything about the way he leads. From early missteps as a young manager to building a company rooted in empathy and accountability, he shows that the strongest cultu...

Crypto follows patterns—just like every major wave of innovation. In this episode, Brad Holden of Protocol VC breaks down what really drives those cycles, how investors separate substance from hype, and where crypto and AI are beginning to converge. From evaluating early founders to understanding when to double down or step back, Brad shares how top VCs navigate frontier tech markets and what make...

Edward Khoury, CTO at Jump, joins Amir to unpack what it really means to lean into discomfort as AI transforms engineering. From redefining craftsmanship in the age of AI-generated code to helping teams evolve their skill sets, Edward shares how he’s creating space for experimentation without losing focus on delivery, culture, or shareholder value. This is a conversation about leadership in motion...

Rick Doten, cybersecurity startup advisor and AI researcher, joins the show to unpack how AI-assisted development is reshaping software—and what it means for security. From startups rushing to ship faster code to the unseen risks of “vibe coding,” Rick explains how engineering teams can balance innovation with secure, resilient design. If your dev team is using AI tools to boost velocity, this con...

What happens when a telehealth CTO takes AI beyond code generation and into the heart of the software development lifecycle? Matt Buckleman, Co-founder and CTO of Hone Health, joins to share how his team uses AI not just to accelerate development, but to rethink workflows—from documentation and traceability to sentiment analysis across teams. This episode dives deep into how he’s blending engineer...

Yosi Dediashvili-Drossos, Co-Founder and CTO of City Hive, joins Amir to unpack how a hyper-focused approach helped transform a niche idea into the dominant e-commerce platform for the liquor industry. From bootstrapping into a complex, highly regulated space to giving small brands a voice, Yosi shares how City Hive built the connective tissue across the entire alcohol supply chain—bridging brands...

What happens when a 17-year Google veteran starts over with a 10-person AI startup? David Petrou, founder and CEO of Continua AI, joins Amir to unpack what it really takes to go from Big Tech stability to startup chaos. They dive into what to keep, what to unlearn, and how to build a high-performing team when everyone has to wear ten hats. From career ladders to “vibe coding,” David shares a candi...

When you step into a new leadership role, do you prefer to build a team from the ground up—or inherit one that already exists? Ashwin Baskaran, VP of Engineering at Mercury, joins the show to unpack what really changes between these two scenarios—and what stays the same. From managing team dynamics to molding culture and earning trust in the first 90 days, Ashwin shares practical frameworks every...

Jarah Euston, Co-Founder and CEO of WorkWhile, joins the show to share how she’s building a worker-first labor marketplace that puts money back into the pockets of frontline employees. Drawing from her own early experience in hourly jobs, Jarah explains why this massive yet underserved workforce deserves better tools, more respect, and faster access to earnings. We dive into automation, AI, re-ski...

Tom Drummond, Managing Partner at Heavybit, joins the show to break down what it takes to build and scale AI “picks and shovels” companies for the enterprise. We dive into the realities of selling into one of the hardest markets to reach, why differentiation matters more than ever, and how startups can wedge their way into massive opportunities despite fierce competition. Key Takeaways • Enterpris...

Jonathan DiVincenzo, co-founder and CEO of Impart Security, joins the show to unpack one of the fastest growing risks in tech today: how AI is reshaping the attack surface. From prompt injections to invisible character exploits hidden inside emojis, JD explains why security leaders can’t afford to treat AI as “just another tool.” If you’re an engineering or security leader navigating AI adoption,...

Daniel Saks, co-founder and CEO of Landbase, joins The Tech Trek to unpack the real meaning of democratizing technology. From agentic AI that works for you—not the other way around—to rethinking workflows and change management, Daniel shares why this shift is bigger than the move from on-prem to cloud. For tech leaders, founders, and operators, this episode reveals how to reclaim time, scale smart...

Matt McLarty, CTO at Boomi, joins the show to break down what enterprise AI adoption really looks like in 2025. From navigating the hype cycle to identifying practical first steps, Matt shares what separates companies that are seeing value from those stuck in endless pilots. If you’re a tech leader wondering how to move beyond experimentation and into measurable outcomes, this episode is your play...

Vipin Kumar, Head of CUSO IB Data Strategy and Analytics at Deutsche Bank, joins me to unpack one of the toughest problems in financial services: managing data quality in a highly regulated industry. From the outside, it might look like a box-checking exercise. In reality, it’s a complex mix of legacy systems, global frameworks, regulatory controls, and the constant push to balance defensive compl...