Taylor Made Thoughts

Scott Taylor
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Taylor-Made Thoughts is where I share my personal reflections on books, mental models, and frameworks that shape how I think and live. Whether you’re here for practical insights or to spark your own thinking, these episodes are crafted with care—just for you.

  1. Sep 11

    Business Failure - Why My Residential Cleaning Business Failed

    I started a residential cleaning business hoping to build a scalable company with recurring revenue. A few months later, I shut it down. In this episode, I give an honest postmortem of why the business failed—and why the reasons were more complicated than simply not working hard enough or executing well enough. The biggest problem was a lack of meaningful differentiation. To most customers, one residential cleaning company looked much like another, which made the business highly price-sensitive and difficult to market. I also ran into challenging competitive dynamics. I was trying to operate completely above board - with W-2 employees, workers’ compensation insurance, payroll taxes, and other legitimate business expenses - while competing against independent cleaners and informal operators with much lower overhead. Immigration and the availability of lower-cost labor also shaped the market in ways that made it difficult to compete on price while maintaining healthy margins. On top of that, I never found a reliable customer-acquisition channel. Yelp produced customers, but at a cost that didn’t make economic sense. Other channels failed to generate enough demand, and I ultimately spent too much money testing marketing approaches that didn’t work. In this episode, I break down: • How I launched the business and found my first customers• Why recurring revenue wasn’t enough to make the model attractive• The difficulty of differentiating in a commoditized local-service market• What it costs to compete while operating legally and above board• Why my marketing channels failed• How much I spent—and what I learned from shutting the business down This isn’t a story about giving up after the first setback. It’s a case study in recognizing when the underlying economics and market dynamics may not justify continuing—and what entrepreneurs can learn from a failed business experiment.

  2. Sep 5

    Dan Sullivan: The 4 C’s Formula: Your building blocks of growth: commitment, courage, capability, and confidence.

    The 4 C’s Formula: Commitment → Courage → Capability → Confidence In this episode, I explore Dan Sullivan’s 4 C’s Formula and why confidence doesn’t come before taking action—it comes after. When you commit to a goal that’s bigger than anything you’ve done before, you’re almost guaranteed to face uncertainty. Moving forward anyway requires courage. That courage forces you to develop new capabilities, and those capabilities ultimately create confidence. I talk about how this framework applies to entrepreneurship, personal growth, and doing things before you feel ready—and why waiting until you feel confident may be exactly what keeps you stuck. Commitment → Courage → Capability → Confidence. Then the cycle starts again. ---- Ready to make your first dollar in business? Stop waiting until you feel ready. START is my $1 community for people who want to take the first steps toward building a business. (Yes, it really only costs $1 to join.) Join START here: skool.com/start-2464/about

  3. Aug 31

    Introducing Opaque: A Snail Mail Subscription for Better Decisions

    I’m trying something new. It’s called Opaque — a snail mail subscription built around one idea: How do you make good decisions when you don’t know how things will turn out? Each issue puts you inside a real decision faced by an entrepreneur, leader, investor, or historical figure. You’ll get the information they had at the time — but not what happened next. Then you have to decide. What would you do? What are you assuming? What risks are you overlooking? And how confident should you really be? Only later do you discover what actually happened and get a chance to compare your reasoning with reality. In this episode, I explain why I’m creating Opaque, how the experience will work, and why I think practicing decisions under uncertainty is one of the best ways to develop better judgment. No hindsight. No obvious answers. Just you, the information available at the time, and a decision to make. This is an experiment, and I’d love for you to be part of the first group to try it. Sign Up For Opaque: https://opaqueletter.com/ My Personal website: https://scotttaylor.me/

  4. Aug 16

    “Geometry” for Staying Cool & Calm: 3 Rules for Navigating Life (by Dan Sullivan)

    What if staying calm in an uncertain world came down to three simple rules? In this episode, I explore Dan Sullivan’s “Geometry” for staying cool and calm—a simple framework built around three ideas: Everything is made up.Nobody’s in charge.Life isn’t fair.At first, these might sound funny. But taken together, they can actually be incredibly freeing. If everything around us was ultimately invented by someone, we’re free to invent something better. If nobody is really in charge, we don’t need to wait for permission. And if life isn’t fair, we can stop expecting reality to conform to our expectations and focus instead on what we can actually control. A short episode about uncertainty, entrepreneurship, expectations, and a useful mental model for staying calm when things don’t go according to plan. https://amzn.to/3SyqrkJ

  5. Aug 9

    The Millionaire Master Plan: Your Personalized Path to Financial Success by Roger James Hamilton

    What if the path to becoming a millionaire isn’t the same for everyone? In this episode of Taylor Made Thoughts, I explore Roger James Hamilton’s The Millionaire Master Plan and its central idea: building wealth isn’t just about working harder or following someone else’s formula—it’s about understanding where you are now and choosing the right strategy for your particular stage. I break down Hamilton’s framework for moving through different levels of wealth, why the skills that get you to one level may not get you to the next, and how your approach to making money should evolve as your resources, experience, and opportunities change. Along the way, I look at what I found useful in the book, where I’m skeptical, and how its ideas apply to entrepreneurs trying to figure out what they should actually be focusing on next. If you’ve ever felt like you’re doing a lot but aren’t sure whether you’re working on the right things to build wealth, this framework offers an interesting way to think about the problem. Buy the Book: https://amzn.to/4g4DQJa (affiliate link)

  6. Jul 17

    How Will You Measure Your Life?: Finding fulfilment using lessons from some of the world's greatest businesses (by Clayton Christensen, James Allworth, and Karen Dillon)

    In this episode, I discuss How Will You Measure Your Life? by Clayton Christensen, James Allworth, and Karen Dillon—a book that takes the management theories Christensen taught at Harvard Business School and applies them to one of the most important questions we can ask ourselves: What makes for a fulfilling life? Rather than relying on inspirational advice, Christensen argues that the same principles that help companies succeed can also help us make better decisions about our careers, relationships, and personal lives. I spend most of the episode focusing on three ideas that stood out to me. First is the concept of deliberate strategy vs. emergent strategy. We often believe we need to map out every step of our future, but Christensen shows that many of the most successful companies—and people—arrive somewhere they never originally planned. The key isn't predicting the future; it's having clear values while remaining flexible enough to recognize and pursue unexpected opportunities. Next, I dive into motivation theory, exploring why money and external rewards only go so far. Christensen draws on research showing that while fair compensation matters, long-term fulfillment comes from meaningful work, opportunities to grow, responsibility, and making a genuine contribution. It's a useful framework for thinking about both our own careers and how we lead teams. Finally, we discuss outsourcing—not just as a business decision, but as a life decision. Which responsibilities should you keep because they create meaning or strengthen relationships, and which are better delegated so you can spend more time on what matters most? Viewing your personal life through the same lens as resource allocation in business can lead to surprisingly powerful insights. Whether you're building a company, managing a career, or simply trying to live more intentionally, this book offers practical mental models for aligning your daily decisions with the life you ultimately want to build. Books referenced (affiliate links): How Will You Measure Your Life?: https://amzn.to/4faaYjs Top Five Regrets of the Dying: https://amzn.to/3TnA060 Getting to Plan B: https://amzn.to/4wH3uu6 The Innovator's Dilemma: https://amzn.to/4wcAzhH Rise and Fall of Strategic Planning: https://amzn.to/3T7apOK Discovery-Driven Growth: https://amzn.to/4yt5K9S The Origin and Evolution of New Businesses: https://amzn.to/3T3z9ra

  7. Jul 15

    Inside the Box: How Constraints Make Us Better (David Epstein)

    We tend to think that more freedom, more options, and more resources naturally lead to better outcomes. In Inside the Box, bestselling author David Epstein (author of Range) argues the opposite: the right constraints don't limit us—they unlock our best thinking. In this episode, we explore why boundaries, deadlines, limited resources, and self-imposed rules can produce greater creativity, better decisions, and more satisfying work. Drawing on psychology, neuroscience, history, and fascinating real-world stories, Epstein challenges the modern obsession with maximizing options and shows why "thinking outside the box" is often the wrong advice. We discuss: Why unlimited choice often leads to paralysis rather than freedom. How constraints force our brains to escape default patterns and discover genuinely novel ideas. The surprising ways great artists, entrepreneurs, scientists, and organizations have used limitations to create breakthrough work. Herbert Simon's concept of "satisficing" and why searching for the perfect option often makes us less happy. The hidden costs of constant multitasking and why behavioral constraints can improve both productivity and well-being. Why designing for edge cases often creates better solutions for everyone. How to deliberately introduce constraints into your own work to become more creative, focused, and effective. One of the biggest takeaways from this book is that creativity isn't the absence of limits—it's often the result of them. Whether you're building a business, writing, investing, or simply trying to make better decisions, Inside the Box offers a practical framework for turning constraints into a competitive advantage. If you enjoyed this episode, subscribe for more conversations about books, mental models, psychology, decision-making, and the ideas that help us think more clearly. Buy the book (affiliate link): https://amzn.to/4f1putE

  8. Jul 3

    Working Backwards: Insight, Stories, and Secrets from Inside Amazon (by Colin Bryar and Bill Carr)

    In this episode, I dive into Working Backwards: Inside Stories and Secrets from Amazon by Colin Bryar and Bill Carr, focusing on two of Amazon's most influential management ideas. First, I explore the Working Backwards process—Amazon's practice of starting with a future press release and FAQ before building a product. Instead of asking, "What can we build?" the process forces teams to answer, "What would customers actually be excited about?" I discuss why writing clarifies thinking, how the PR/FAQ uncovers weak ideas early, and why this framework can be useful far beyond large tech companies. I also talk about input vs. output metrics, one of Amazon's core operating principles. While most businesses obsess over outcomes like revenue or profit, Amazon emphasizes the controllable inputs that actually drive those results. We discuss how identifying the right input metrics can lead to better decisions, faster learning, and more consistent long-term execution. Whether you're building a startup, launching a product, or simply looking for a better way to make decisions, this episode explores practical lessons from one of the world's most influential companies—and how you can apply them to your own life + work. Buy the book (affiliate link): https://amzn.to/3SydyqF

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About

Taylor-Made Thoughts is where I share my personal reflections on books, mental models, and frameworks that shape how I think and live. Whether you’re here for practical insights or to spark your own thinking, these episodes are crafted with care—just for you.

Information

  • Creator
    Scott Taylor
  • Years Active
    2026
  • Episodes
    14
  • Rating
    Clean
  • Copyright
    © Scott Taylor
  • Show Website
    Taylor Made Thoughts

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