Taylor Made Thoughts

About Taylor Made Thoughts

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.

Publisher

Scott Taylor

Category

education

Language

en

Explicit

No

First episode

25 May 2026

Latest episode

11 Sept 2026

Latest episodes

14 episodes in the feed.

1. 

   11 Sept 2026

   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. 

   5 Sept 2026

   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 (https://www.skool.com/start-2464/about?utm_source=chatgpt.com)

3. 

   31 Aug 2026

   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://tally.so/r/WOkRLP My Personal website: https://scotttaylor.me/

4. 

   16 Aug 2026

   “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. 

   9 Aug 2026

   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. 

   17 Jul 2026

   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. 

   15 Jul 2026

   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. 

   3 Jul 2026

   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

9. 

   20 Jun 2026

   How to Combat the Ego: 2 Ways to Convince Yourself or Someone Else to Change Their Life

   We all know how hard it is to change our own behavior—and even harder to convince someone else to change theirs. In this episode, I explore two surprisingly effective ways to work around the ego, reduce resistance, and create real behavioral change. Along the way, I compare two competing models of personal development: the popular "be, do, have" philosophy that focuses on identity and breakthroughs, and the "do, have, be" approach championed by thinkers like Alex Hormozi, where action comes first and identity follows. Whether you're trying to improve yourself, influence others, become better at sales, or simply have more productive conversations, these ideas can help you sidestep defensiveness and make change feel less threatening.

10. 

    19 Jun 2026

    Reflections on 100 Cold Calls: Why Every Business Should Start this Way

    Episode Description I recently challenged myself to make 100 cold calls in 3 days—targeting dental offices, gyms, physical therapy clinics, and veterinary practices. In this episode, I share what actually happened, what surprised me, and what I learned. If you're starting a business, I make the case that every founder should do 100 cold calls before worrying about websites, logos, or marketing strategies. You'll learn more from talking to real prospects than from weeks of "research."

11. 

    16 Jun 2026

    Tao: The Watercourse Way (Allen Watts, Al Chung-liang Huang)

    For this episode, I discuss The Watercourse Way by Alan Watts, a book that explores Daoism through ideas like the Dao, yin-yang polarity, and wu wei—or effortless action. The biggest theme that stood out to me is that the things we want most often seem to elude us, while the things we care less about arrive naturally. Looking back on my own life, I've repeatedly gone after one outcome—money, business success, achievement—only to receive something entirely different, like better health, meaningful friendships, or personal growth. The book argues that much of our suffering comes from trying to force life rather than working with it. Instead of viewing reality as something to conquer, Daoism encourages us to move with the natural flow of events, much like water finding its course. Another idea that resonated with me is that suffering and success often go hand in hand. Many accomplished people seem to go through significant hardship before achieving their greatest results. Rather than resisting difficulty, Daoism suggests that it may be an essential part of growth. My main takeaway is that life may be less about control and more about alignment. The harder we force outcomes, the more resistance we create. Sometimes the most effective action is not doing more, but learning when to let go and trust the process. Link to the book: https://amzn.to/4oCA4dC (affiliate)

12. 

    8 Jun 2026

    What the CEO Wants You To Know: How Your Company Really Works (Ram Charan)

    One of the biggest lessons I took from What the CEO Wants You To Know by Ram Charan is that business is much simpler than most people make it. Great CEOs focus on a handful of fundamentals: customers, cash flow, return on invested capital, and growth. Instead of getting lost in departments, metrics, and complexity, Charan argues that everyone should understand how the business actually makes money. It's a short, practical book that helped me think more like an owner and less like a specialist. Get the book: https://amzn.to/4uyEnIq (affiliate)

13. 

    2 Jun 2026

    Tim Ferris’s - Fear Setting

    In this episode, we explore Tim Ferriss's powerful concept of Fear Setting—a practical exercise designed to help you overcome indecision, anxiety, and procrastination. Instead of focusing only on goals, Fear Setting encourages you to define your fears, examine the worst-case scenarios, and create plans to prevent or repair potential setbacks. Learn how this simple framework can help you make better decisions, take meaningful risks, and move forward with confidence. Resources: • Tim Ferriss TED Talk: Why You Should Define Your Fears Instead of Your Goals — tim.blog/ted (https://tim.blog/ted?utm_source=chatgpt.com)• Fear-Setting Exercise Slides (PDF) — Fear-Setting Sample Slides (https://tim.blog/wp-content/uploads/2017/06/ted_ferriss_fear_setting_sample_slides.pdf?utm_source=chatgpt.com) Fear-setting is a framework Tim Ferriss has described as one of the most valuable exercises he does, helping him evaluate risks, reduce anxiety, and make difficult decisions with greater clarity.

14. 

    25 May 2026

    The Psychology of Hope — How to Actually Achieve Your Goals

    Welcome to *Taylor-Made Thoughts* — a series exploring mental models, psychological frameworks, and practical tools for improving thinking and increasing your chances of achieving meaningful goals. Each episode breaks down actionable ideas and mental tools you can apply immediately in your own life. In this episode, I reflect on *The Psychology of Hope* by C. R. Snyder and explore six mental tools that can help you actually achieve your goals — including agency, “waypower,” flexible thinking, and building alternative paths when obstacles arise. I discuss how these ideas connect to motivation, resilience, entrepreneurship, and personal growth, along with my own notes and reflections from the book. Get the book: https://amzn.to/4v9D9Es (affiliate link)

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Apple Podcasts (US)

5.0 / 5

1 ratings

Spotify

4.0 / 5

3 ratings

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