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Leadership, Technology, and the “It Depends” Philosophy: Insights from Kevin Goldsmith

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Kevin Goldsmith, a seasoned CTO, mentor, and principal at Nimble Autonomy, joins the conversation today as we discuss Kevin’s journey in technology leadership across the US, Sweden, and the UK, touching on his experiences and the release of his new book, It Depends: Writing on Technology Leadership 2012 to 2022.

The discussion covers technology adoption, with a focus on ChatGPT and its recent Teams product. Kevin reveals how his team embraced ChatGPT, its role in policy creation, and the advantages of the Teams program for collaborative work. The conversation unfolds into a deeper exploration of the evolving role of CTOs, the future landscape for aspiring leaders, and the potential impact of advanced tools on development processes.

Kevin, in addition, sheds light on the creation of his book, sharing insights into the inspiration behind the title It Depends and the unique approach that he took in preserving the original context of his blog posts. He touches on the audiobook creation process and the decision to self-release, emphasizing accessibility and convenience for readers.

Kevin also offers us a glimpse into his vision for the future, both in terms of technology leadership and the evolving capabilities of generative text generators like ChatGPT. The candid and insightful conversation provides listeners with a multifaceted view of technology, leadership, and the intricate balance between innovation and the human touch, and you won’t want to miss this conversation.

Kevin Goldsmith
Kevin GoldsmithFounder of Nimble Autonomy
Kevin Goldsmith is a seasoned technology leader with over three decades of experience in the tech industry. As the current Chief Technology Officer at DistroKid, the world’s leading digital music distributor, Kevin plays a pivotal role in shaping the future of music distribution. He is also the Principal and Founder of Nimble Autonomy, LLC, where he provides expert advice and mentorship to emerging start-up leaders and managers.

Previously, Kevin has held several high-profile positions, including Chief Technology Officer at Anaconda, Onfido, and Avvo. He also made significant contributions as the Vice President of Engineering, Consumer at Spotify, Director of Engineering at Adobe Systems, and as a Development Lead at Microsoft. His diverse experience across these significant tech companies showcases his expertise and versatility in the field.

In addition to his corporate roles, Kevin is a well-regarded author and speaker. He has been writing the “Puppies, Flowers, Rainbows and Kittens” blog since 2004, a platform where he shares insights and opinions on various technology topics. His contributions extend to other notable sites like, the Spotify Developer blog, and the Adobe Developer Network. As an internationally recognized keynote speaker, Kevin has shared his knowledge and experiences in over 17 countries, making him a global thought leader in technology.

For more information about Kevin and his work, visit his website at His extensive experience and active engagement in the tech community make him a prominent figure in the technology world.

Time Stamps:

[00:33] – Kevin Goldsmith joins us today!

[03:42] – Kevin candidly shares that after years of struggling to quit smoking, he successfully quit when his child was conceived.

[04:45] – Armed with a PhD in neuroscience, Kevin quit smoking cold turkey after moving to Europe.

[07:38] – Having faced the challenge of using smoking breaks to clear his mind, Kevin now copes differently.

[09:27] – Reflecting on sixteen years without smoking, Kevin recalls a unique experience at Microsoft leveraging smokers’ restlessness.

[11:32] – Kevin admits that, even in his pre-smoking days, he sometimes consciously chose to smoke influenced by the band scene that he was part of.

[13:05] – Eager to explore new technologies, Kevin’s team embraced ChatGPT, finding it to be a valuable and helpful tool.

[15:42] – Kevin shares how ChatGPT has been a valuable tool for writing policies, streamlining their creation.

[17:44] – Opting for efficiency in creating his book’s index, Kevin used ChatGPT to automate the process.

[19:03] – Kevin reflects on his role as a CTO, valuing his longevity.

[20:29] – Kevin finds the diverse career paths of CTOs fascinating, noting the changed landscape enabling quicker advancements.

[23:39] – Reflecting on the evolution of the CTO role, Kevin sees a richer learning landscape today.

[27:42] – Kevin likens tools like ChatGPT to skilled interns, adept at routine tasks, but not for inventive or complex challenges.

[29:57] – Despite excitement and venture capitalist interest, some ideas have never materialized or panned out.

[32:57] – Kevin discusses how the new product, akin to ChatGPT+, offers additional features like admin interface, privacy settings, and team chat sharing.

[35:09] – Kevin encourages using ChatGPT to seek code suggestions and streamline tasks, emphasizing its value despite initial skepticism.

[39:29] – Preserving the original context of blog posts, Kevin’s book, It Depends, explores timeless tech leadership themes.

[41:01] – The book’s title reflects Kevin’s philosophy on nuanced technology leadership, emphasizing decision-making that depends on context.

[43:42] – Kevin shares what inspired the idea behind his book.

[46:39] – Kevin currently uses Podbean for his podcast but is contemplating self-hosting for a more contextual and enjoyable experience.

[50:22] – Kevin reveals where It Depends can be purchased.

[53:10] – Listeners are advised not to edit their own audiobook if they aren’t familiar with the process.

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