Ep. 208 – Is your reliance on specific software holding your business back? With Airtable’s recent acquisition making headlines, Chris reflects on how he accidentally replaced Airtable long before he ever intended to leave it behind. He shares his journey from discovering Airtable as a simple, user-friendly way to work with databases to making it central to his business, and eventually realizing that AI-powered apps and custom interfaces could do the job faster, more flexibly, and without the limitations he had started encountering. Chris breaks down what changed in the technology landscape, where Airtable struggled to evolve, and what its acquisition may signal about the future of software, AI, and how businesses build their tech stacks. Tune in to learn how to spot when it’s time to rethink your tech stack and what AI-powered tools could make possible for your business.

• 1:03 – How Chris accidentally replaced Airtable without ever setting out to replace it.
• 4:17 – Chris’s first introduction to Airtable and why its approach to databases was so different.
• 5:49 – What made Airtable so powerful for businesses that were used to spreadsheets.
• 10:08 – How Airtable gradually replaced other tools in Chris’s business, including his CRM.
• 11:02 – Why Airtable’s interfaces became a critical weakness as competitors evolved.
• 15:04 – How AI-powered app building changed the value of interacting directly with a database.
• 24:33 – What Chris thinks Airtable’s acquisition means and why he believes businesses need to keep evolving their technology stack.

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Ep. 207 – How do you decide whether to build your next software solution or buy it? In this episode, Chris breaks down what it really means to navigate the new “build versus buy” decision. He shares examples of simple, highly specific software he has built for himself with AI, from calendar syncing and networking tools to custom forms and habit tracking, and explains why building a solution around your own process can sometimes make more sense than paying for a platform you’ll only use a fraction of. You’ll hear how to determine what you actually need, when buying software still makes sense, and why learning to build with AI gives you the ability to make that decision for yourself instead of automatically reaching for your credit card. Tune in to learn how to make smarter software decisions and determine whether your next solution should be built or bought.

• 1:11 – The misconception that AI is untrustworthy and its effects on software development.
• 5:49 – Valuing the development of software with AI compared to traditional methods.
• 8:25 – An example of creating a personalized calendar syncing app with AI.
• 10:11 – Ways to improve security in AI-built applications through proactive measures.
• 12:46 – Recognizing that the value is in completing tasks, not just performing them.
• 14:41 – Using AI to automate repetitive tasks, allowing time for more important work.
• 16:40 – The cost savings of developing your own software solutions instead of using subscriptions.
• 21:19 – Building custom forms with AI instead of paying for form software like Jotform or Typeform.
• 26:16 – When buying makes more sense: why Chris wouldn’t build an LMS for himself right now.
• 29:54 – Chris's personal build-versus-buy check formula.

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Ep. 206 – Are you relying too much on doers instead of true tech leaders? In this episode, Chris discusses the critical mistake many businesses make by hiring doers instead of leaders in technology. He shares insights from his own evolution from a doer to a leader, emphasizing the importance of having strong technical leadership to guide teams effectively. Chris outlines the risks of poor tech setup and the pitfalls of relying on freelancers who may not align with your business objectives. He argues that investing in proper tech leadership can unlock the full potential of your team, leading to greater efficiency and innovation. Tune in to learn how to transition from a doer mentality to a leadership approach that maximizes your technological capabilities.

• 3:02 – Why hiring a doer instead of a technical leader can hinder your technology's effectiveness.
• 5:56 – The importance of having a technical leader who can bridge business objectives and technology.
• 10:39 – How a technical leader can innovate solutions that off-the-shelf tools may not provide.
• 12:43 – The critical role of ideation in a tech team and the need for leadership that encourages innovative thinking.
• 14:15 – Navigating technology decisions requires a deep understanding of your business model and objectives.
• 16:00 – The rising importance of data security and proper structures as technology evolves in your business.
• 22:30 - The app Chris has been working on that will help guide your business decisions.

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