Ep. 211 – How do you know when it’s time to stop adapting your business to your software and start building the software around your business? In this episode, Chris discusses the decision-making process behind building custom applications instead of using off-the-shelf solutions. He shares experiences of creating three specific apps tailored to his needs: a fitness tracker, a habit tracker, and a church note-taking app. Chris points out that many existing software tools are over-featured and lack the exact capabilities you require. He shows how building your own apps can empower your team and streamline operations, ultimately increasing efficiency. Tune in to discover how to identify what your software is missing and use your skills to fill the gaps instead of relying on generic solutions.

• 1:04 – The dual nature of building apps: challenges without structure and capability.
• 4:48 – How to solve the specific gaps your current software isn’t addressing.
• 6:02 – How AI and APIs can help you customize tools without building an entire platform.
• 7:27 – How a simple custom app can solve a problem that more complicated software doesn’t.
• 11:23 – Why starting with an existing app can make building your own solution faster and easier.
• 12:42 – How building small apps can help you improve your AI skills and test new models.
• 13:08 – How to design software around your actual workflow instead of changing your workflow to fit the software.
• 16:03 – How to turn a simple personal solution into a tool that could have broader applications.
• 18:52 – How to recognize when you’re better off buying instead of building.
• 23:34 – How to find the right balance between building it yourself and relying on existing software.

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Ep. 210 – What costs are you not accounting for when you want to move faster? In this episode, Chris explores the hidden expenses that come with the pursuit of speed in business. He shares a cautionary tale about a founder who, despite being on the brink of developing an AI application, pulled back due to an obsession with rapid progress. Chris highlights the importance of understanding the costs of clarity, technology, and team well-being, and how ignoring these can lead to burnout and inefficiency. He challenges you to consider whether you're ready to pay the price for speed. Tune in to learn how slowing down to assess your foundation can lead to greater long-term success.

• 0:10 – Why speed is one of the most addictive, expensive things in business
• 3:31 – Organizing your data is crucial to using AI effectively
• 6:40 – The most overlooked cost in business
• 9:28 – Why a fragmented tech stack can become a massive business problem
• 15:48 – Why slowing down can be the fastest path forward
• 19:14 – What happens when AI investment grows faster than the results
• 21:07 – What it really takes to build at the speed you want
• 26:23 – Why you can’t expect to move fast while paying slow

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Ep. 209 – Are you leveraging software as a strategic advantage in your business? In this episode, Chris discusses internal software solutions and how they can improve your company. He notes that many business leaders may not realize they’re already operating as software companies internally, which can lead to growth. Chris outlines strategies for harnessing this power, including understanding the software development process, ensuring quality assurance, and implementing effective testing protocols. He shares insights from his experiences with various companies and offers advice on integrating AI to streamline operations. Tune in to learn how to position your business for success through the use of internal software.

• 2:29 – Understanding the difference between building a SaaS company and building software for internal use.
• 5:57 – Why thinking of your business as a software company internally can unlock new opportunities for growth.
• 6:50 – The skills and expertise your team needs to start operating like an internal software company.
• 10:34 – Why quality assurance and testing are essential for building secure, effective internal software.
• 15:34 – Why a formal bug reporting process makes software development easier to track, manage, and improve.
• 16:24 – Building custom software to visualize the metrics and information that actually matter to your business.
• 20:00 – How AI can help turn a complex spreadsheet into a customized internal dashboard.
• 23:15 – Why the fastest-growing companies of the future will be internally software-oriented.

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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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Ep. 205 – How can you leverage personal software to drive efficiency without getting overwhelmed? In this episode, Chris breaks down how to start creating personal software by focusing on one small, specific problem that is slowing you down. He also shares a real example of turning a cumbersome spreadsheet into a streamlined judging dashboard, showing what this approach looks like in practice. If you've been curious about creating your own software but don't know where to start, this episode offers a simple place to begin.

• 6:45 – How Chris turned a cumbersome spreadsheet into a streamlined judging dashboard by solving one specific problem.
• 8:58 – Why starting with a small, focused software project can produce faster results than trying to build an entire system.
• 11:35 – How better communication with AI can help you turn an idea or problem into a useful software solution.
• 15:48 – Why building software around your own needs first can help you create systems that ultimately serve others better.
• 16:24 – How personal software can make your business more efficient and easier to operate.
• 17:07 – Why you should get one internal process working well before trying to scale the solution across your business.

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Ep. 204 – What if the best software for your business wasn't something you bought, but something built specifically for you? In this episode, Chris introduces the concept of personal software: software designed around your unique workflow, your business, and your team. He explains why becoming your own customer, starting small with just a few features that solve a real problem, and owning the software you build can lead to greater efficiency, better security, and more control over your data. Drawing from his own experience, Chris shares why every business owner should rethink what's possible when software is built to fit their needs instead of forcing them to fit someone else's. Tune in to learn how adopting a personal software approach can transform your operational efficiency and empower your team.

• 1:04 – The critical distinction between vibe coding and personal software for secure development.
• 3:00 – How allowing AI to build apps on insecure foundations can exponentially increase data risks.
• 5:45 - How Chris got started with building apps and AI authorship.
• 9:15 – Why you must maintain control over your data when building applications.

• 11:37 – Why building your own software infrastructure can eliminate unnecessary costs and limitations.
• 15:42 – The concept of personal software and the process of becoming your own customer.
• 25:25 - How you can learn to build your own personal software.

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