Best CTO Confessions Podcasts (2025)

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Episode 175: Growing as a Leader by Taking Calculated Risks with Eric Levin 55:42

8d ago55:42

55:42

In this episode, Eric Levin shares his journey to becoming CTO and how taking calculated risks shaped his leadership style, one that's purpose-driven and people-focused.Key takeaways:- Why calculated risks are essential for growth- How transparency can strengthen team dynamics- Why embracing hard, boring tasks matters for leadershipTune in for an h…

1
Episode 174: The Power of Technology & AI with Joe Hsy 45:39

10d ago45:39

45:39

In this episode, Joe Hsy shares his approach to leading with innovation while balancing the benefits and risks of emerging tech—especially AI and data privacy. From scaling teams without micromanaging to aligning technology with real business value, Joe offers thoughtful insights for every tech leader.Key takeaways:- Ethical use of data and buildin…

1
Episode 173: Systematizing Chaos - The CTO’s Playbook with Rob Molchon 48:38

1M ago48:38

48:38

How do tech leaders build scalable, sustainable systems without descending into chaos? Rob Molchon, CTO of Vestwell, shares his insights on structuring order in fast-moving tech environments. We also take a quick trip down memory lane to see just how far tech has come.Key takeaways from the podcast are: – Clear ownership ensures tasks get done with…

1
Episode #129: Steve Quirk of Robinhood on Prediction Markets & The Evolution of Markets 47:24

1M ago47:24

47:24

Chief Brokerage Officer at Robinhood Markets. Prior to joining Robinhood, he oversaw the strategy and deployment of initiatives for Trading at TD Ameritrade, He also served as a member of the company’s Senior Operating Committee, which shaped the strategic focus of the organization. Our guest also focusing on teaching the next generation of investo…

1
Episode 172: Bridging the Gap Between Practical Engineering and Academia with Guy Yachdav 43:51

1M ago43:51

43:51

The tech sector can be highly specialized, especially for leaders in biotechnology. In this episode of CTO Confessions, host TC Gill chats with Guy Yachdav, Senior Director at Immunai. Tune in for insights into his leadership journey.Key takeaways from the podcast are: - Academia and tech intersect in exciting ways, like using machine learning to p…

1
Episode 171: Servant Tech Leadership in the Realm of Collectors with Dan Van Tran 51:54

2M ago51:54

51:54

In this episode of CTO Confessions, Dan Van Tran shares how AI and tech power the authentication of collectibles, from cards to video games. We explore AI-driven pricing, scaling tech teams, and servant leadership in a unique industry.Key takeaways:- AI’s role in authenticating and valuing collectibles- Why emotions matter in price estimation- The …

1
Episode 170: The Intersection of Emotion and Technology with Armen Berjikly 58:25

2M ago58:25

58:25

In this episode, we explore how emotions and technology work together to support employee growth. Tune in for a thoughtful discussion on what happens when technology meets emotions within the context of an organization.Key takeaways from the podcast are:- Aligning executive vision with employee execution fosters a unified direction.- Unstructured c…

1
Episode 169: Designing Culture with Data at the Core with Matt Culver & Nomaan Ahmed 59:27

2M ago59:27

59:27

In this episode of CTO Confessions, TC Gill talks with engineering leaders Matt Culver & Nomaan Ahmed from Super.com about how data-driven decision-making shapes both engineering and company culture. They explore the role of data in leadership, team dynamics, and fostering a strong workplace culture.Key Takeaways:- Measuring the right things, even …

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Episode 168: What Makes a Great Tech Leader with Savas Karas 1:00:28

3M ago1:00:28

1:00:28

What makes a great tech leader? Savas Karas, CTO of CAPREIT, believes it starts with kindness, support, and open feedback loops. In this episode of CTO Confessions, he shares how fostering a strong culture helps teams stay motivated, aligned, and unafraid of challenges.Key takeaways from the podcast are: - A shared vision keeps teams focused on mea…

1
Episode 167: The Complex Role of Leadership in Tech with Daniel Natic 43:07

3M ago43:07

43:07

In this episode of CTO Confessions, our host TC Gill and guest Daniel Natic dive into the complex role of leadership in tech, exploring the balance between managerial expertise and deep technical knowledge.Key takeaways from the podcast are: - Tech leaders must stay sharp. Keep up with trends, drive change, and understand your team’s decisions.- Tr…

1
Episode 166: Strategies for Crafting Educational Solutions with Todd Ellermann 49:30

3M ago49:30

49:30

In this episode of CTO Confessions, we explore the dynamic relationship between educational standards, student engagement and the role of artificial intelligence. Listen to Todd Ellermann’s perspective on how these elements intersect and how they are shaping the future of EdTech.Key takeaways - EdTech companies must understand state-specific standa…

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Episode 165: How to Structure a Growing AI Company with Yaron Inger 48:08

3M ago48:08

48:08

On this episode of CTO Confessions, our host, TC Gill, is joined by Yaron Inger, Founder of Lightricks, who reveals the unfiltered story behind scaling an AI-driven company. Yaron shares the lessons learned during their growth, emphasizing the importance of managing cashflow, deciding to change their business model and navigating all major growth c…

1
Episode 164: The Art of Organizational Transformation with Conlath Alcock 55:47

4M ago55:47

55:47

In this episode, our host, TC Gill, sits down with Conlath Alcock, Client CTO at T-Systems, to explore how understanding an organization’s current state and learning from the past can set the stage for a strong foundation and successful transformation.By IT Labs

1
Episode 163: Humble Leadership in Practice with Tim Vasil 59:00

4M ago59:00

59:00

In this episode of CTO Confessions, host TC and Tim Vasil, CTO of LeanTaaS, explore humble leadership, discussing Tim’s journey from solo contributor to leading high-performing teams, his approach to feedback, building a human-centric culture, and knowing when to delegate.By IT Labs

1
Episode 162: The Human Side Of Tech Leadership With Ivan Kusalic 46:37

4M ago46:37

46:37

In this episode of CTO Confessions, host TC Gill chats with Ivan Kusalic, CTO of green tech organization Enpal. Ivan’s diverse career has shaped his unique approach to tech leadership, rooted in curiosity, empathy, and a commitment to transparency and growth. He shares candid insights on leading in the renewable energy industry, inspiring tech lead…

1
Episode 161: A Fintech CTO's Playbook for Driving Sustainable Innovation with Skyler Nesheim 56:36

5M ago56:36

56:36

In this episode, TC, our CTO Confessions host, and Skyler Nesheim, the CTO of Dwolla, discuss the strategies and mindsets that have propelled his career in the competitive and dynamic world of FinTech. A hidden world that we all use without knowing it.Key takeaways from the podcast are: Develop a framework to prioritize core, unique technology that…

1
Episode 160: Confessions of a Tech Maverick with Jeremy Hodges 45:42

6M ago45:42

45:42

In this episode, we sit down with Jeremy Hodges, the CTO of Live Oak Bank, a digital-only small business bank. Jeremy shares his passion for customer-centric technology, his approach to balancing innovation and compliance, and the importance of addressing organizational weaknesses. Hear how Jeremy cascades his audacious vision throughout the compan…

1
Episode #128: Andrew O'Connell US Investing Champion on Early Trading Struggles, Trade Sizing & Risk 1:10:44

6M ago1:10:44

1:10:44

US Investing Championship 2023 top performer with a gain of+103.5%. Currently leading this years 2024 competition with a whopping 409% as of date of recording. He’s a fundamental & Technical Analysis. Founder of Pristine Capital. Confessions of a Market Maker presents Andrew O’Connell. ---------------------------------------------------------------…

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Episode 159: Cracking the Code of Tech Leadership with Farzona Pulatova 46:04

6M ago46:04

46:04

In this CTO confession session, we get insights from a VP of Engineering on Building High-Performing Teams. Join us as we dive into the mind of Farzona Pulatova, a seasoned tech leader who has navigated the industry’s complexities with grace and innovation.Key takeaways from the podcast are: - Farzona emphasizes the importance of creating a transpa…

1
Episode 158: Confessions of a Tech Turnaround Titan with Misha Makara 54:11

7M ago54:11

54:11

In this session of CTO Confessions, we get an unvarnished look into the trials, tribulations, and hard-won wisdom of a tech leader who’s stepped into the arena of huge challenges and turned things around. Key takeaways from the podcast are:- Misha's key message is that mistakes and failures are inevitable, but they are also your greatest growth opp…

1
Episode #127: Anthony Pompliano on Economic Data, BTC Volatility & How To Live An Extraordinary Life 49:25

7M ago49:25

49:25

Founder & CEO of Professional Capital Management. He has built and sold a number of successful businesses, while also investing in approximately 200 companies. He created and manages one of the largest independent financial media platforms in the world. Published author of the “How to Live an Extraordinary Life”. Confessions of a Market Maker Prese…

1
Episode 157: Mastering the Art of Empowering High-Performing Teams with Catherine Miller 44:39

7M ago44:39

44:39

In this episode, our host, TC Gill sits down with Catherine Miller, the Chief Technology Officer of Flatiron Health. Catherine shares her passion for using data and technology to improve cancer treatment and drug development - a truly purposeful mission. We dive into Catherine's journey to the CTO role, the challenges of leading through different g…

1
Episode 156: A Conversation on Metadata, Meaningful Work, and Embracing Change with Madalina Tanasie 49:03

9M ago49:03

49:03

Madalina Tanasie, CTO of Collibra, shares her insights on AI governance, data intelligence, and SaaS evolution. She highlights how advancements in AI have democratized technology and emphasizes the need for solid data governance. Tanasie also stresses the importance of meaningful work for engineers to drive innovation. Her perspectives offer valuab…

1
Episode #126: JC Parets on Portfolio Strategies, Technical Analysis and Bull Market Parties 57:54

9M ago57:54

57:54

Founder of All Star Charts, a research platform for both professional and retail investors. He is one of the most widely followed technical analysts in the world. Earned his Chartered Market Technician designation (CMT) in 2008. Frequent speaker at top investing conferences and universities. Confessions of a Market Maker presents JC Parets --------…

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Episode #125: Anne-Marie Baiynd on Recovering from Big Losses, Neuroscience & Trading Methodology 1:20:46

10M ago1:20:46

1:20:46

Twenty year trader and is featured often in major fintech outlets and aligned with many trading platforms -Benzinga Pro, Investors Business Daily, Metastock, MotiveWave, Trendspider, RocketScooter, PlaceYourTrades, TopstepTrader, and Traderade. Shes the president and CEO of TheTradingBook.com and the author of The Trading Book: A Complete Solution …

1
Episode #124: Dave Mabe CTO Officer at Trade Ideas on Backtesting, creating a process & AI trading 1:12:06

10M ago1:12:06

1:12:06

Chief technology officer at Trade Ideas & consistent profitable systematic independent trader for 17 years. Confessions of a Market Maker present Dave Mabe ------------------------------------------------------------------------------------------------------------------ Dave's Website: https://www.davemabe.com/ Dave on Twitter: https://x.com/davema…

1
Episode #123: Peter Reznicek on Options Trading, Market Internals & Profile 1:04:27

11M ago1:04:27

1:04:27

Trading full-time since 1999. He’s been a principal and head trader for RBC capital and Translucent Capital Management. Now he’s a retail trader trading weekly options on a strict technical basis. Founder of Shadowtrader.net. Confessions of a Market Maker presents Peter Reznicek. ---------------------------------------------------------------------…

1
Episode 155: Navigating the Responsible Development of LLMs with Vijay Karunamurthy 56:33

1y ago56:33

56:33

Vijay Karunamurthy, Field CTO at Scale AI, joins CTO Confessions to discuss his career in AI and the future of generative models. Vijay shares lessons from early neural network research and his time at YouTube, where he helped build recommendation systems. He explains his role translating customer needs to product roadmaps and ensuring ethical, tra…

1
Episode 154: Architecting Success: Andreas Westendorpf's Vision of Tech as Business Backbone 37:14

1y ago37:14

37:14

In this insightful episode of CTO Confessions, listeners are treated to an in-depth exploration of technology and leadership through the experiences of Andreas Westendörpf, CTO of Emma. His journey, from a budding software engineer to an influential technology leader, is a central theme. The episode covers the crucial role of good architecture, wit…

1
Episode #122: BTC Analysis 31:42

1+ y ago31:42

31:42

Piggybacking off of the newly launched equity breakdown series, JJ & Ray give a rundown of BTC on the chart, its origins and another notable tidbits. Fresh off of 11 spot ETF approvals, Billions of dollars have flowed into these Bitcoin spot ETFs --------------------------------------------------------------------------------------------- Any liste…

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Episode #121: Hunter Horsley of Bitwise on New BTC ETF Approval 52:54

1+ y ago52:54

52:54

Former product manager at Facebook and Instagram. A graduate of Wharton and was a Forbes 30 Under 30 honoree. Chief Executive Officer of Bitwise Asset Management and co-founder of the 5-year-old firm. Bitwise is one of the world’s largest and fastest-growing crypto-specialist asset managers. The firm is known for launching the world’s first and lar…

1
Episode #120: CCCC Stock Breakdown 18:15

1+ y ago18:15

18:15

JJ breaks down the company C4 Therapeutics (CCCC) fresh off its new deal with Merck. Drawing from his previous experience running deals, JJ informs the listeners on what to look out for if you plan to play this ticker or one similar. Looking past the catchy headlines, you'll learn to let the chart tell you the real story. --------------------------…

1
Episode 153: Eco-Innovation in Retail and the Path to Sustainable Business With Adam Siegel 31:44

1+ y ago31:44

31:44

TC Gill converses with Adam Siegel, co-founder of Recurate, a trailblazing retail tech startup. Siegel discusses his transformative journey from early computer enthusiasm to pioneering sustainable solutions in the retail sector. Listen in as he shares insights on creating a remote-first, mission-driven company culture, the challenges of balancing p…

1
Episode #119: HCDI Stock Breakdown 23:44

1+ y ago23:44

23:44

A new series on Confessions of a Market Maker. JJ breaks down the company Harbor Custom Development (HCDI). Drawing from his previous experience running deals, JJ informs the listeners on what to look out for if you plan to play lower priced/ lower float stocks. Looking past the catchy headlines, you'll learn to let the chart tell you the real stor…

1
Episode 152: Breaking Codes and Building Teams With Rob Phillips 34:35

1+ y ago34:35

34:35

In this episode, TC engages with Rob Phillips, the Vice President of Software Engineering at UDig, a Richmond-based consulting company. Phillips delves into his journey from a passionate technologist in his youth to a seasoned leader in the tech industry. He shares valuable lessons on transitioning to senior leadership, the importance of understand…

1
Episode 151: Leading with Insight: A Tech Odyssey With Robert Matsuoka 42:03

1+ y ago42:03

42:03

Join us in a compelling conversation with Robert Matsuoka, where he unveils his transformative journey from a tech-centric role to a strategic leadership position. In this episode of CTO Confessions, Robert delves into the art of delegation, the dynamics of building effective teams, and the criticality of nurturing talent. He also sheds light on ma…

1
Episode #118: Tony Battista of Tastylive on Market Making, Options Trading & Transition From the Floor 1:00:42

1+ y ago1:00:42

1:00:42

Started his career in options and futures trading in 1983, as an independent Market Maker at the Chicago Board Options Exchange (CBOE), as well as a local independent trader at the Chicago Board of Trade (CBOT). He served on the CBOE arbitration committee for over 10 years, ruling on disputes between traders and trading firms. Presently, he is the …

1
Episode #117: Anna Coulling on Volume Price Analysis, Macro Picture & Trading Psychology 1:25:50

1+ y ago1:25:50

1:25:50

She has been involved in the financial markets for almost 17 years as a trader and investor. She takes a three dimensional view, based on technical, fundamental and relational analysis. This powerful approach, when combined with price action and candle patterns, has given her a deep and detailed knowledge of the forces that drive the financial mark…

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