Story of a fractional CTO with Thanos Diacakis

Story of a fractional CTO with Thanos Diacakis

Author: PM Power Consulting July 12, 2025 Duration: 53:38

My 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 to multiple clients
  • Scaling Challenges: Thanos shared experiences with scaling projects, particularly with Uber's bikes and scooters, highlighting the importance of having systems in place to manage growth
  • Learning from Others: Thanos emphasized the value of learning from others and cross-pollinating ideas across different clients to improve software delivery 


Thanos Diacakis helps startups and growing companies overcome software bottlenecks, scale engineering teams, and deliver high-quality products faster. With over 25 years in software development, his background spans both early-stage ventures and tech giants like Uber and Included Health, where he led the technical integration of the JUMP Bikes acquisition, scaling the platform to 45k vehicles and over 2 million monthly trips. He’s seen elite teams stall when outdated processes leave them too heads-down to course-correct. With lean, evidence-backed practices, he unlocks faster delivery and greater developer satisfaction, so velocity rises while burnout falls.


SOCIAL MEDIA LINKS:

Website:  https://www.cosmicteacups.com/

LinkedIn: https://www.linkedin.com/in/thanosd/


Behind every line of code, there's a person with a story. Software People Stories, from PM Power Consulting, moves beyond abstract theory and polished case studies to explore the real, human experience of building technology. This isn't about hypotheticals; it's a collection of candid conversations with the practitioners themselves-developers, designers, product managers, and architects-who share firsthand accounts from the trenches. They talk about the paths that led to success and, just as importantly, the unexpected detours and failures that provided the most valuable lessons. Each episode delves into the nuanced journey of discovering what users need, designing elegant systems, navigating complex development, and ultimately delivering solutions that matter. By focusing on these personal narratives, the podcast reveals the core of software creation: a blend of technical skill, creative problem-solving, and team dynamics. Listeners gain practical wisdom and relatable perspectives on the challenges and triumphs inherent in the tech industry. Tune in for an honest look at the craft, where the stories of people are just as crucial as the software they build. You'll find this podcast a refreshing source of insight for anyone involved in or curious about the technology and business landscapes, offering career lessons learned the hard way.
Author: Language: English Episodes: 100

Software People Stories
Podcast Episodes
Rewiring Careers, Redefining Impact with Anu Dwaraknath [not-audio_url] [/not-audio_url]

Duration: 38:51
In this episode of Software People Stories, Gayatri Kalyanaraman speaks with Anu Dwaraknath, Staff Technical Program Manager at Lam Research, about her dynamic journey across geographies, domains, and roles. From her ear…
Passion, Patents, and Powering Down AI with Fred Jordan [not-audio_url] [/not-audio_url]

Duration: 50:50
Gayatri Kalyanaraman is in conversation with Dr. Fred Jordan, CEO and Co-Founder at AlpVision and FinalSpark - Expert anticounterfeit technologies - Expert biocomputing talks about his journey to make a difference in AI…
Entrepreneurship, AI, and Social Impact with Santosh Kaveti [not-audio_url] [/not-audio_url]

Duration: 49:57
I am very happy to bring you the inspiring story of Santosh Kaveti, CEO and Founder of ProArch Technologies.In this conversation he talks about: His Origin Story: From applied mathematics to entrepreneurship, navigating…
Interpretability and Explainability with Aruna Chakkirala [not-audio_url] [/not-audio_url]

Duration: 1:01:02
Her early inspiration while growing up in Goa with limited exposure to career options. Her Father’s intellectual influence despite personal hardships and shift in focus to technology.Personal tragedy sparked a resolve to…
Selling IT based solutions with Deepak Mittal [not-audio_url] [/not-audio_url]

Duration: 57:42
I am in conversation with Deepak Mittal, CEO of FFTalos Technologies. In this insightful episode, Deepak Mittal shares his career journey from coding to consultative selling, reflecting on his evolution from a tech enthu…
Involving Communities in Product Development with Jake McKee [not-audio_url] [/not-audio_url]

Duration: 54:32
My guest today is Jake McKee, a pioneer in the modern customer community movement.In this conversation, he shares: Hiss Origin Story: His unique career bridging product design, engineering, and community strategy. Commun…
From Theater to entrepreneurship with Stamatis Astra [not-audio_url] [/not-audio_url]

Duration: 40:14
My guest today is Stamatis Astra is the Co-Founder and Chief Business Officer of Intelligent Relations. In this freewheeling conversation, he talks about:Introduction & Origin StoryStamatis shares his varied career journ…
Amplifying Reinvention with Deeksha Senguttuvan [not-audio_url] [/not-audio_url]

Duration: 33:50
Gayatri Kalyanaraman is in conversation with Deeksha Senguttuvan, Founder and CEO of BabyMD and executive trustee for a pediatric cancer foundation . Deeksha brings her authentic self to share powerful stories of persona…
From COBOL to AI with Allen Cooper [not-audio_url] [/not-audio_url]

Duration: 47:49
Shiv is in conversation with Allen Cooper, President and CEO of Ancilla Ventures. Their focusis in providing tools to healthcare support staff to improve patient outcomes.In this conversation, Allen talks about:Allen’s O…
Exploring Peer-to-Peer Tech with Mathias Buus Madsen [not-audio_url] [/not-audio_url]

Duration: 50:26
Shiv is in conversation with Mathias Buus Madsen, CEO of Holepunch, Copenhagen. In this episode, Mathias shareshis journey into software development, beginning as a math student and evolving into a passionate advocate fo…