Cto Think



A pragmatic podcast about leadership, product dev, and tech decisions between two recovering Chief Technology Officers.


  • BLM, White Privilege, Accountability, Guilt, Responsibilities, and Helping

    09/06/2020 Duração: 55min

    The world feels like a different place from just a couple weeks ago, but it's not. The United States is still in the same place it has been for a long time, if you're a minority. Randy and Don discuss the Black Lives Matter movement, police accountability, racism, privilege, guilt, and where they might fit in to not being part of the problem.

  • From Manager/Dev to Non-coding Manager

    19/05/2020 Duração: 31min

    Right before the COVID pandemic hit, Randy was asked to take on the management of two new teams, which changed his typical role of manager-developer to strictly people management, meetings, and project tracking. Don and Randy discuss the change as it affected Randy and what he thinks is the most important factors for folks in the same boat.

  • Difficult Choices and Hard Conversations

    31/03/2020 Duração: 43min

    Don and Randy talk about what's been going on with the COVID-19 pandemic and how it has affected their firms, jobs, and side projects. What does it mean to talk to folks under your wing? What kind of leadership does it take when the real world seems out of your control?

  • Improving Visual Communication for Remote Management

    25/02/2020 Duração: 29min

    Randy is making efforts to improve the communication of visual examples via remote video meetings. We discuss his first attempt to achieve online whiteboarding using a Macbook Pro, a Wacom One tablet, and a Google Jamboard.

  • Security Concerns Keep Coming

    11/02/2020 Duração: 34min

    In Don's role as CTO for AspirEDU, he has a number of security audits posed by potential customers and increasing complexity around third-party hosts. Randy keeps wanting to talk about the XFL (Part 2).

  • Modern Content Management Options

    07/01/2020 Duração: 44min

    Don and Randy discuss content management options from the old-school Full Stack apps, WYSIWYG SaaS, and Headless + Static Site Generator options

  • Automation vs Programming

    17/12/2019 Duração: 41min

    Don describes his work on moving his company to Microsoft and his use of Power Apps. This leads to a discussion of the automation vs programming strategies and how this might be the future for all non-coding employment.

  • Switching to Services

    12/11/2019 Duração: 33min

    Randy is part of a team focused on building a Service Oriented Architecture with Go. Don figures out he has always been using services, but the SOA acronym seemed to involve more than simply work. Randy explains further the use of messages, queues, and other approaches to request buffering.

  • Is Accessibility a Worthwhile Focus?

    29/10/2019 Duração: 33min

    Domino's Pizza recently lost a lawsuit regarding the lack of accessibility features for their online ordering platform. Don and Randy discuss the ramifications of the decision and whether accessibility is worth the time and effort product managers might put into making their products more inclusive.

  • How Should a CTO Use Their Time?

    01/10/2019 Duração: 32min

    When a CTO is juggling multiple responsibilities, people, and projects, what is the best use of their time? Randy, once again, tells Don to put down the keyboard and quit coding stuff!

  • Organizational Train Wrecks explained by College Football Dumpster Fires

    10/09/2019 Duração: 38min

    In honor of the second week of the college football season, Randy and Don discuss three programs, UCLA, Tennessee, and FSU, falling into disaster scenarios and compare each with CTO failures at technology firms. We keep the football/sportsball strategy discussion to a minimum, but we do eventually call out Tennessee as the "Steve Ballmer" of college football schools. Go Rocky Top?

  • Should Startups Avoid Hiring a CTO?

    20/08/2019 Duração: 33min

    A recent blog post by Philip Thomas of Moonlight titled "Startups Should Not Hire a CTO" sparked a conversation about why blanket statements like "Startups Should Not Do X" that are clickbait and should probably be avoided as good advice. Instead, we discuss letting your needs to drive your hires, instead, and the kinds of people you probably do want to hire to lead technical efforts. Randy's cats don't like anything about the recording, in addition to the article.

  • Authentication: Buy it or Build it?

    06/08/2019 Duração: 46min

    With hacking stories dropping on a seemingly daily basis, the question keeps coming up about application security: Should you build your own user authentication or use an external service? This week, Don and Randy discuss the Buy vs Build debate around auth, and whether the high costs of outsourcing outweigh the high risks of rolling your own.

  • 2x CTOs talk about 10x developers

    16/07/2019 Duração: 49min

    In reaction to a Twitterstorm about the concept of a 10x engineer being important for any startup, we discuss the downfalls of such a thing and what positives exist.

  • Post-mortem on Randy's Job Search

    09/07/2019 Duração: 54min

    Randy is about to start a new job and has a number of opinions about the job search, hiring, negotiation process he recently went through. Don tries to play Devil's Advocate as the employer/hiring side, but Randy's not hearing any of it! Don uses coconuts as the example of currency and Randy somehow manages to quadruple the asking price for labor in the Hawaiian produce marketplace Don tried to set up.

  • Ditching Wordpress vs Free-time Driven Development

    18/06/2019 Duração: 55min

    The show begins discussing setting up a product roadmap for AspirEdu, but things devolve when Don mentions he is considering swapping Wordpress for the marketing website with a static site builder. Randy thinks adding more developer dependencies is a bad idea and coins the term "Free-time Driven Development" (tm) and can't wait to make T-Shirts and Medium posts promoting the brand.

  • From Hands-on Dev to CTO: Jess Szmajda, CTO of Axios

    04/06/2019 Duração: 44min

    We have an exceptional guest for our 50th episode in Jess Szmajda, CTO of Axios, and we cover a whole lotta ground: From building "horrible PHP sites", to constructing retail tech teams from scratch, we then tackle the subject of taking on the role of CTO of a fast-growing media firm, being a trans CTO, and promoting a more diverse community in technology. Whew! We start out discussing the difference between a CTO and Director/VP of Engineering, title creep, and whether the idea of a "software architect" has any relevance at all. We then cover wider ground with managing small vs large teams, the adoption of Spotify squads/pods in team management, and adding new business (TV) that is vastly different than the core company product (online publishing). The subject matter covers a vast amount of ground, but it's all valuable in today's tech community.

  • Stages of the CTO Lifecycle

    21/05/2019 Duração: 54min

    This week we review an old, but good, blog post by Andy Skipper named "Looking at the life of the CTO through the stages." We discuss our own experiences across these stages and the ones we haven't reached, yet. Randy also continues his rant on tech developer/manager hiring practices, so no surprise there!

  • Benefits of Continuous Integration

    07/05/2019 Duração: 41min

    Over the past two decades of working in tech, the use of Continuous Integration (or CI) has become a mainstream approach to product development. Randy and Don discuss the systems they used before (or lack thereof), what they use now, and why Continuous Integration meets the hype.

  • Business Metrics and the Lack of Context

    23/04/2019 Duração: 42min

    We discuss business metrics, reporting, statistics, and how many of the numbers, without context, lack much value. Can your business deliver the Five Nines? Does it even need to? What kind of performance can you guarantee when upstream providers are involved?

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