Built to Grow: The Small Business Playbook

Ryan Naylor
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  • ENTREPRENEURSHIP

Built to Grow: The Small Business Playbook with Ryan Naylor is a podcast for small business owners who are done guessing and ready to grow with intention. Each episode features real conversations with founders and operators who’ve been through the highs, the hard lessons, and the growing pains of running a small business. No fluff. No theory. Just honest stories and proven strategies you can actually use. Listeners walk away with real playbook tactics on hiring, leadership, operations, and scaling. The kind of insights you only get from experience, not textbooks. If you’re building a business, managing a team, and trying to grow without burning out, this podcast is for you. Because growth isn’t luck, it’s built.

  1. From $1M to $10M Business: What Actually Changes in Branding, Hiring & Growth

    APR 27

    From $1M to $10M Business: What Actually Changes in Branding, Hiring & Growth

    What separates a $1M business from a $10M business? In this episode, Ryan Naylor sits down with Kayden Muzila, founder of Musilla Creative, to break down what actually changes as companies scale—especially when it comes to branding, creative strategy, and understanding your audience. Kayden shares his journey from creative director in the Hollywood film and advertising world to building a fast-growing agency from scratch after multiple layoffs forced a reset in his career. Together, they explore: Why most brands fail to scale their messaging past $1M The shift from “what we like” to “what the audience actually wants” How delegation becomes the real bottleneck in growth What hiring and trust look like inside a scaling creative business How content strategy should actually be structured for results, not just virality Why authenticity beats trends in social media marketing If you’re building a business, leading a team, or trying to break through your next revenue ceiling, this conversation is packed with real-world insight from both the agency and operator side. Follow Kayden Muzila on IG: https://www.instagram.com/kayhaos/ Follow Ryan on IG: https://www.instagram.com/ryan.nylr/ Follow our Podcast on IG: https://www.instagram.com/built.to.grow.podcast/ Learn more about AvaHR and get a free trial of our ATS: www.avahr.com Watch the live Interviews on YouTube: https://www.youtube.com/@avahrsoftware

    24 min
  2. From Overwhelmed to Optimized: How Small Businesses Are Using AI to Scale with Katie Shive

    APR 17

    From Overwhelmed to Optimized: How Small Businesses Are Using AI to Scale with Katie Shive

    In this episode, Ryan sits down with Katie Shive to break down what AI actually means for small business owners—not in theory, but in execution. From building AI agents that act like personal assistants to creating scalable content systems, Katie shares how businesses can start leveraging AI today to save time, increase efficiency, and stay competitive. They dive into:  What’s really coming in the next 18 months with AI  How to use AI agents to automate daily tasks and decision-making  Why most businesses are using AI wrong (and how to fix it)  How to build a brand voice that doesn’t sound like “AI wrote it”  The role of personal branding in a world with less trust and more automation This episode isn’t about replacing people—it’s about amplifying what great operators can do with the right systems. If you’re a business owner trying to figure out where AI actually fits into your day-to-day… this is your playbook. Follow Katie Shive on IG: https://www.instagram.com/heykatieshive/ Follow Ryan on IG: https://www.instagram.com/ryan.nylr/ Follow our Podcast on IG: https://www.instagram.com/built.to.grow.podcast/ Learn more about AvaHR and get a free trial of our ATS: www.avahr.com Watch the live Interviews on YouTube: https://www.youtube.com/@avahrsoftware

    40 min
  3. Why Most Entrepreneurs Stay Stuck (And How to Actually Scale) with Tiffany Rosenbaum

    APR 10

    Why Most Entrepreneurs Stay Stuck (And How to Actually Scale) with Tiffany Rosenbaum

    In this episode of the Built to Grow Podcast, Ryan sits down with Tiffany Rosenbaum—entrepreneur, business owner, and advisor—to break down what it actually takes to scale a business the right way. From starting with nothing during the 2008 crash to building a fast-growing company, Tiffany shares the real, behind-the-scenes lessons most entrepreneurs learn the hard way. They dive into:  The biggest misconception small business owners have about scaling  Why your team—not just your strategy—is the real growth driver  How to build systems that actually support growth  The importance of hiring slow and building the right culture  Why stepping out of the day-to-day is critical for long-term success  And the uncomfortable truth about what’s really holding most entrepreneurs back Tiffany also shares how implementing an advisory board helped her scale over 100% in a year—and why surrounding yourself with the right people can completely change your trajectory. If you’re feeling stuck in your business, still wearing too many hats, or struggling to grow beyond your current level—this episode will challenge the way you think about leadership, systems, and scale. Follow Tiffany on IG: https://www.instagram.com/tiffanymrosenbaum/ Follow Ryan on IG: https://www.instagram.com/ryan.nylr/ Follow our Podcast on IG: https://www.instagram.com/built.to.grow.podcast/ Learn more about AvaHR and get a free trial of our ATS: www.avahr.com Watch the live Interviews on YouTube: https://www.youtube.com/@avahrsoftware

    31 min
  4. From First Client to Fully Booked: How to Scale a Service Business

    MAR 27

    From First Client to Fully Booked: How to Scale a Service Business

    In this episode, Ryan sits down with Charles Drown, owner of Square One Home Inspections, to break down the real, unfiltered journey of building a small business from the ground up. Charles shares what most people don’t talk about...like the constant pressure of ownership, the early days of struggling to find customers, and why not all work is good work. From cold starts and stacks of unused business cards to building a referral engine through social media, he walks through the exact strategies that helped him grow. They dive into: How to use Instagram to build real business relationships (not just followers) Why giving away free value is the fastest path to long-term growth The biggest mistakes new business owners make with pricing When to raise your prices—and when not to Systems and tools that save time and scale your operations The mindset shift from technician to business owner Charles also shares blunt advice for anyone thinking about starting their own business: you don’t need permission, you just need to start. If you're a small business owner (or want to be one), this episode is packed with practical strategies, honest insights, and a no-BS look at what it really takes to grow. Follow Ryan on IG: https://www.instagram.com/ryan.nylr/ Follow our Podcast on IG: https://www.instagram.com/built.to.grow.podcast/ Learn more about AvaHR and get a free trial of our ATS: www.avahr.com Watch the live Interviews on YouTube: https://www.youtube.com/@avahrsoftware

    22 min
  5. The Playbook After the NFL: Markus Wheaton on Business, Mindset & Mental Health

    FEB 20

    The Playbook After the NFL: Markus Wheaton on Business, Mindset & Mental Health

    In this episode of Built to Grow, host Ryan Naylor sits down with former Markus Wheaton, a standout wide receiver for the Pittsburgh Steelers, who’s now tackling an entirely new arena: small business ownership. Ryan asks the question everyone wants to know: “What’s harder… the NFL or running a small business?” Markus’ answer sets the tone for a raw, honest, and inspiring conversation about transitioning from elite athletics to entrepreneurship. Markus opens up about: 🔸 Living in the moment at Oregon State and never assuming the NFL was guaranteed 🔸 Draft-night doubts and the mindset that kept him “always on the rise” 🔸 How he built Western Skies Landscaping from the ground up 🔸 Early challenges: HOA battles, permits, hiring, sub-contractors, quality control 🔸 What he brought from the locker room into business leadership: accountability, ownership, and culture 🔸 How working out, connecting with others, and staying curious protect his mental health 🔸 The loneliness of entrepreneurship and how to fight it 🔸 The transparent leadership style he learned from coach Mike Tomlin 🔸 His next chapter: scaling to $4M and building a home-services investment portfolio This episode is packed with wisdom for small business owners, athletes in transition, and anyone trying to grow personally and professionally. Markus’ mindset, humility, and hunger make this one unforgettable. Follow Markus on Instagram: https://www.instagram.com/taewheaton/ Western Skies Landscaping: https://www.instagram.com/westernskieslandscaping/ Follow Ryan on IG: https://www.instagram.com/ryan.nylr/ Follow our Podcast on IG: https://www.instagram.com/built.to.grow.podcast/ Learn more about AvaHR and get a free trial of our ATS: www.avahr.com Watch the live Interviews on YouTube: https://www.youtube.com/@avahrsoftware

    30 min
  6. Built to Grow with Jason Payne & Ryan Naylor: How to Build and Scale a Roofing Business

    JAN 23

    Built to Grow with Jason Payne & Ryan Naylor: How to Build and Scale a Roofing Business

    Jason Payne went from making $12.50 an hour to running a multi-million-dollar roofing company and he did it by asking better questions, building better people, and never settling. In this episode, Jason and Ryan Naylor discuss how to hire hungry talent, fire based on values, delegate like a CEO, and reverse-engineer your growth. If you’re a business owner serious about scaling, leadership, and legacy, this episode is a must-listen. Follow Jason Payne: https://www.instagram.com/jasontheroofer/ Follow Ryan on IG: https://www.instagram.com/ryan.nylr/ Follow our Podcast on IG: https://www.instagram.com/built.to.grow.podcast/ Learn more about AvaHR and get a free trial of our ATS: www.avahr.com Watch the live Interviews on YouTube: https://www.youtube.com/@avahrsoftware

    48 min
  7. Human First: Building Trust and Connection in the Workplace

    11/07/2025

    Human First: Building Trust and Connection in the Workplace

    In this episode of The People Ops Playbook, host Ryan Naylor sits down with Chloe Street, an expert in the human side of business and former HR leader at Meta, Credit Suisse, and Morgan Stanley. Together, they unpack what it really means to put the “human” back in human resources. From fighting workplace isolation to creating cultures rooted in trust and genuine connection, Chloe shares practical tools for leaders... like her “90-second rule” and connection formula of Presence, Curiosity, and Trust, that can transform how teams communicate and thrive. If you’ve ever wondered how to build a team that feels seen, heard, and inspired, this episode is your playbook for leading with empathy and depth in today’s disconnected world. 💡 Key Takeaway: Connection isn’t a grand gesture, it’s built in 90-second moments of presence. Follow Chloe on LinkedIn: https://www.linkedin.com/in/chloestreet1/ Follow Ryan on IG: https://www.instagram.com/ryan.nylr/ Follow our Podcast on IG: https://www.instagram.com/built.to.grow.podcast/ Learn more about AvaHR and get a free trial of our ATS: www.avahr.com Watch the live Interviews on YouTube: https://www.youtube.com/@avahrsoftware

    46 min
  8. Future-Proof HR: Lessons from William Tincup

    10/03/2025

    Future-Proof HR: Lessons from William Tincup

    Ryan sits down with HR tech veteran William Tincup to unpack what’s really changing in HR and what never will. They dive into payroll, compliance, the rise of agentic AI, and how HR leaders can adapt without losing the human touch. William shares insights from his decades in recruiting, his work with WorkDefined, and why hyper-personalization and real human connection still matter in talent acquisition. Follow William on LinkedIn: https://www.linkedin.com/in/tincup/ Follow Ryan on IG: https://www.instagram.com/ryan.nylr/ Follow our Podcast on IG: https://www.instagram.com/built.to.grow.podcast/ Learn more about AvaHR and get a free trial of our ATS: www.avahr.com Watch the live Interviews on YouTube: https://www.youtube.com/@avahrsoftware

    43 min
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5
out of 5
8 Ratings

About

Built to Grow: The Small Business Playbook with Ryan Naylor is a podcast for small business owners who are done guessing and ready to grow with intention. Each episode features real conversations with founders and operators who’ve been through the highs, the hard lessons, and the growing pains of running a small business. No fluff. No theory. Just honest stories and proven strategies you can actually use. Listeners walk away with real playbook tactics on hiring, leadership, operations, and scaling. The kind of insights you only get from experience, not textbooks. If you’re building a business, managing a team, and trying to grow without burning out, this podcast is for you. Because growth isn’t luck, it’s built.

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