Thanos Diacakis - Podcast Details

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Data Driven Thanos Diakakis on Surviving the Software Apocalypse – AI, Agile, and Good EngineeringOn this episode of Data Driven, we venture into the ever-shifting landscape of software engineering, AI-assisted coding, and the sometimes chaotic future of development teams with special guest Thanos Diacakis—no, not the Marvel villain, but a powerhouse in software leadership whose career spans scrappy startups to tech giants like Uber.Hosts Frank La Vigne, Andy Leonard, and resident AI BAILeY welcome Thanos for an insightful, witty, and sometimes philosophical conversation about the promise and perils of AI in software engineering. From the rise (and risks) of “vibe coding” to the changing definition of good engineering, Thanos shares...

2025-08-2058 min

The Brand Called You Scaling Startups & Tackling Tech Debt: Insights from Thanos Diacakis, Software Delivery Coach & Fractional CTOEver wonder how technology leaders adapt between nimble startups and tech giants, or what it truly takes to ship software that matters? In this insightful TBCY episode (S7 E062), Ashutosh Garg sits down with Thanos Diacakis—software delivery coach, fractional CTO, patent-holder, and independent consultant—to unpack 25+ years of lessons from the front lines of engineering and startup life.Below you’ll find key topics explored in the episode, organized by timestamp, complete with guiding questions to help you navigate the most relevant insights for your journey.

2025-08-0625 min

Tech for Non-Techies 263. The feature factory trap: when output doesn’t equal progressWhy do so many software teams feel busy — but deliver so little value? Fractional tech leader Thanos Diacakis shares why shipping more features doesn’t always mean progress. Drawing on 25+ years in software — from startups to scaling JUMP Bikes at Uber — he explains how to escape the trap of over-planning, feature overload, and technical debt. Listen to learn: Why planning more often leads to less progress What non-technical leaders need to ask their tech teams How to find your team’s bottleneck (and why that changes over time)...

2025-07-3031 min

PM Power Consulting Story of a fractional CTO with Thanos DiacakisMy guest today is Thanos Diacakis, Software Delivery Coach & a Fractional CTO. We covered a wide range of topics that included: Insightful Experiences: Thanos shared many insightful and thought-provoking experiences and perspectives, particularly on software delivery life cycle improvements without explicitly using terms like Kanban Balancing Work and Personal Life: Thanos emphasized the importance […]

2025-07-1600 min

Entrepreneur Conundrum From Burnout to Breakthrough: Building Better Engineering Teams with Thanos DiacakisEpisode Title: From Burnout to Breakthrough: Building Better Engineering Teams with Thanos DiacakisGuest: Thanos DiacakisHost: Virginia PurnellPodcast: Entrepreneur ConundrumLinks & Resources:Website: https://www.cosmicteacups.comLinkedIn: https://www.linkedin.com/in/thanosd/Download: 7 Mental Models for Software DevelopmentWhat You’ll Hear in This Episode:How Thanos turned early startup experience into a career of helping software teams scaleCommon misconceptions about engineering productivityThe four types of work all software teams should balanceWhy going “faster” often starts with doing lessThanos’ ABCD framework: Iteration, Quality, Complexity, PlanningThe truth about burnout, identity...

2025-07-1430 min

Software People Stories Story of a fractional CTO with Thanos DiacakisMy guest today is Thanos Diacakis, Software Delivery Coach & a Fractional CTO.We covered a wide range of topics that included:Insightful Experiences: Thanos shared many insightful and thought-provoking experiences and perspectives, particularly on software delivery life cycle improvements without explicitly using terms like Kanban Balancing Work and Personal Life: Thanos emphasized the importance of balancing work and personal life, recognizing that while work is important, personal relationships and leisure activities are equally significant.Fractional CTO Business: Thanos discussed the benefits of running a fractional CTO business, allowing for flexibility in managing time and delivering value t...

2025-07-1253 min

🧠 _Ditch the Ticket Factory Mentality | Cosmic Teacups’ Thanos Diacakis Podcast: Dev Interrupted (LS 45 · TOP 1% what is this?)Episode: Ditch the Ticket Factory Mentality | Cosmic Teacups’ Thanos DiacakisPub date: 2025-03-25Get Podcast Transcript →powered by Listen411 - fast audio-to-text and summarizationImagine a world where your engineering team ships features at lightning speed, and they're genuinely happy doing it. Sounds like a fantasy? It doesn't have to be. This week, we're diving into the secrets of building high-performing, happy engineering teams with Thanos Diacakis, a fractional CTO and engineering coach with over 25 years of experience spanning compan...

2025-05-2555 min

Will AI Snap That with Thanos and Rollins CLAUDE FAILED ME!!! (critical bug in production)Claude FailuresHighlighting the dangers of reliance on AI, Rollins had a critical bug make its way to production. In today's episode, Thanos and Rollins discuss the evolving landscape of AI coding agents and their impact on the software development process. They delve into the challenges of ensuring code quality, including the importance of tests and architectural standards. The hosts share anecdotes about their own experiences with AI tools like Claude and Cursor, highlighting both the successes and humorous failures. They also touch on the broader implications of AI in team dynamics and software project management, setting the stage for...

2025-05-0545 min

Will AI Snap That with Thanos and Rollins Vibe Coding Guardrails w/ Colin Morris of ProoflineIn today's episode, Thanos and Rollins are joined by Colin Morris, the CEO of Proofline (proofline.ai), to discuss the future of AI in software engineering. Colin shares insights on the revolutionary impact of generative AI coding, emphasizing the need for guardrails to ensure safety and efficiency. They also delve into the potential of coding agents, the importance of observability, and the evolving role of site reliability engineers. The conversation explores how these advancements are set to transform the industry, providing both unprecedented opportunities and challenges.00:00 Introduction and Welcome00:57 Introducing Colin Morris03:46 Challenges and Risks in AI and Vibe...

2025-04-1446 min

Will AI Snap That with Thanos and Rollins Fact Checking the Lying AI Liars w/ Jeff Mahacek from Fox CheckerFact-Checking AI: Jeff's Mission with Fox Checker | Will AI Snap That?Join hosts Michael Rollins and Thanos as they welcome Jeff Mahacek from Fox Checker. In this episode, Jeff dives into the world of AI, discussing the rampant misinformation and disinformation that pervades the digital landscape. He shares his journey of developing Fox Checker, a tool aimed at automated fact-checking and credibility analysis, and highlights the importance of truth in our society. With a mix of humor and insight, they explore how machine learning can verify facts and combat AI-generated falsehoods. Whether you're an AI enthusiast or a concerned...

2025-04-071h 01

Will AI Snap That with Thanos and Rollins Beyond Buzzwords: The Real Impact of Claude Code, Cursor, and ChatGPT on CodingIn today's episode, hosts Michael Rollins and Thanos discuss their experiences and insights with various AI tools such as ChatGPT, Cursor, and Claude Code. They share the strengths and weaknesses of each tool, delve into specific use cases, and reflect on how the evolving role of AI is impacting the future of software engineering. Notable mentions include the advantages of Claude Chat for handling large pastes and images, Aero as an open-source alternative, and the potential applications of Google's Gemini for architectural discussions. They also touch on the emerging responsibilities engineers will face as AI becomes more integrated into...

2025-03-3144 min

Dev Interrupted Ditch the Ticket Factory Mentality | Cosmic Teacups’ Thanos DiacakisImagine a world where your engineering team ships features at lightning speed, and they're genuinely happy doing it. Sounds like a fantasy? It doesn't have to be. This week, we're diving into the secrets of building high-performing, happy engineering teams with Thanos Diacakis, a fractional CTO and engineering coach with over 25 years of experience spanning companies like Uber, where he optimizes software engineering teams and drives technical innovation.Thanos reveals the common mental models that hold teams back, why 'technical debt' is a myth, and how to break free from the 'feature factory' mindset. Together, h...

2025-03-2555 min

Will AI Snap That with Thanos and Rollins The AI Deleted My Code!Exploring AI Coding Tools: A Deep Dive into Cursor and Coding AgentsIn today's episode, Thanos and Rollins discuss their experiences with AI coding tools, specifically Cursor and various coding agents. They share insights into creating applications, the challenges faced, and the benefits observed. Key topics include the process of leveraging AI for code generation, managing CSV imports, and the nuances of working with different AI models. They also touch on practical tips for effective prompt management, the importance of context windows, and the potential future of integrated AI in software development.00:00 Welcome to Will AI Snap That?00:37 Building an...

2025-03-2148 min

Will AI Snap That with Thanos and Rollins Vibe Coding: Stop Writing Code w/ Sean Byrnes!Navigating the Future of Software Engineering with AIIn today's episode of 'Will AI Snap That?', hosts Michael Rollins and Thanos dive deep into the implications of AI on the future of software engineering. Joined by guest Sean Byrnes, a veteran in Silicon Valley, they discuss the evolving role of software developers, biases against older founders, and the potential for AI to replace traditional coding. The conversation explores how AI tools like Cursor are reshaping development practices, the abstraction of programming, and the impact of reinforcement learning on code quality. They also touch on societal changes, job displacement, and...

2025-03-1446 min

Will AI Snap That with Thanos and Rollins Should Robots Pick and Write Your Grocery List?Navigating the AI-Driven Future: From Automated Groceries to Writing with AIIn today's episode, Thanos and Rollins dive into a range of topics such as the potential of AI to simplify grocery shopping with custom Go applications, how AI can assist in writing, and the ethical dilemmas of using AI in professional scenarios like job applications. They also touch on recent news involving Anthropic and DeepSeek, discussing the contradictions and implications of AI in tech industries. Join them as they explore the usefulness and limits of AI in our ever-evolving world.00:00 Welcome to Will.I.Snap00:18 Navigating the AI Apocalypse01:01...

2025-03-0348 min

Will AI Snap That with Thanos and Rollins Will AI Replace God?Will AI Snap That: Exploring AI's Role in Religion and MoralityIn today's episode, Thanos and Rollins discuss various aspects of how AI might intersect with and impact religious practices and moral decision-making. They delve into topics like whether AI could replace prayer, provide moral guidance, and offer companionship. They also explore the far-reaching implications of AI potentially improving human lives and even replacing government functions. Tune in for a thought-provoking conversation anchored in humor and real-world examples.00:00 Welcome to Will A.I. Snap That00:29 Smoothie Talk and Caviar Curiosity01:50 Follow-Up on Zelda Game Development02:44 Exploring AI Tools and IDEs05:56...

2025-02-2043 min

Will AI Snap That with Thanos and Rollins Will Deepseek Replace ChatGPT?Leveraging AI to Advance AI: DeepSeek R1 and OpenAI's ImpactIn today's episode, hosts Muggle Rollins and Thanos delve into the performance of their podcast's first episode before diving deep into the realm of artificial intelligence. They discuss DeepSeek R1, a new AI model that challenges the dominance of OpenAI's ChatGPT, investigating its cost-effective training methods and its implications for the future of AI development. The hosts also touch on the ethical and legal aspects surrounding AI-generated content, intellectual property, and the latest advancements in AI technology, including model distillation. Listener questions about AI's...

2025-02-1052 min

Entrepreneurship Lab Business Lessons From UberIn this podcast episode of Entrepreneurship Lab, my guest is Thanos Diacakis, a seasoned technology leader with over 25 years of experience in optimizing software development and engineering teams for startups and high-growth companies. Specializing in improving engineering efficiency, refining software architecture, and aligning technology with business goals, Thanos has worked with a range of organizations, from scrappy startups to global giants like Uber. During his tenure at Uber, Thanos led the technical integration of the JUMP acquisition, scaling operations from 45,000 vehicles to over 2 million monthly trips and generating $150 million in annualized revenue.

2025-02-0624 min

Will AI Snap That with Thanos and Rollins Will AI Replace Teachers? What could go wrong?

2025-01-3153 min

Will AI Snap That with Thanos and Rollins Will Robots Replace Call Centers?In this episode of 'Will AI Snap That,' hosts Michael Rollins and Thanos discuss the rapid advancements in AI and its potential to replace call centers jobs. They explore the ethical implications of AI systems, such as training robots to interact with customers using personal context. The conversation touches upon real-world examples of AI applications, including systems that can perform customer service tasks, as well as the challenges of ensuring these systems don't make critical errors. The hosts also debate the pros and cons of AI's ability to replicate human interactions, considering both efficiency gains and potential manipulations...

2025-01-2445 min

Will AI Snap That with Thanos and Rollins Will AI Snap Creators? With Lexie Janson!!!!Thanos and Rollins pair up with the inimitable Lexie Janson, creator extraordinaire, to talk about whether AI can replace creators.

2025-01-1854 min

Will AI Snap That with Thanos and Rollins Will AI Replace Podcasters?Will AI Replace Podcasters? Have you heard of NotebookLM? It's a service from Google that, among other things, will generate a podcast for you based on a set of input documents. It's pretty wild and incredibly useful. Thanos and Rollins dive into whether or not AI can replace podcasters today, and what the future may hold w/re to Podcasting and AI.

2025-01-1046 min

Will AI Snap That with Thanos and Rollins Will AI Replace Software EngineersThanos and Rollins discuss if and how AI will impact the field of Software Engineering.

2025-01-0348 min