Home » Built to Grow Podcast: Why Most Entrepreneurs Stay Stuck (And How to Actually Scale) with Tiffany Rosenbaum
Monday, April 13th, 2026
In this episode of the Built to Grow Podcast, Ryan Naylor sits down with Tiffany Rosenbaum, entrepreneur, business owner, and advisor, to unpack what it really takes to scale a business the right way.
From starting with nothing during the 2008 crash to building a rapidly growing company, Tiffany shares the lessons most entrepreneurs only learn through experience.
They cover:
- The biggest misconceptions small business owners have about scaling
- Why your team, not just your strategy, drives real growth
- How to build systems that actually support and sustain scale
- The importance of hiring intentionally and shaping the right culture
- Why stepping out of day-to-day operations is essential for long-term success
- The hard truth about what holds most entrepreneurs back
Tiffany also breaks down how creating an advisory board helped her grow more than 100 percent in a single year, and why the people you surround yourself with can completely shift your trajectory.
If you feel stuck, stretched too thin, or unable to break through your current level, this episode offers a fresh perspective on leadership, systems, and sustainable growth.
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