『Ryan Estes, Founder of KitCaster | From Losing 95% of Clients During COVID to $2M Annual Revenue in 18 Months, Building a Leading Podcast Booking Agency, Scaling to 25 Employees, Exiting Successfully, and Thriving in the AI Era. (Episode 782 - Ryan Estes)』のカバーアート

Ryan Estes, Founder of KitCaster | From Losing 95% of Clients During COVID to $2M Annual Revenue in 18 Months, Building a Leading Podcast Booking Agency, Scaling to 25 Employees, Exiting Successfully, and Thriving in the AI Era. (Episode 782 - Ryan Estes)

Ryan Estes, Founder of KitCaster | From Losing 95% of Clients During COVID to $2M Annual Revenue in 18 Months, Building a Leading Podcast Booking Agency, Scaling to 25 Employees, Exiting Successfully, and Thriving in the AI Era. (Episode 782 - Ryan Estes)

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In this episode of the Grow A Small Business Podcast host Troy Trewin interviews Ryan Estes, co-founder of KitCaster, shares his remarkable journey from losing 95% of his digital agency clients during COVID to building a thriving podcast booking agency that reached a $2 million annual run rate within just 18 months. Ryan discusses how KitCaster scaled from 3 to 25 team members, the lessons learned from rapid growth, and the strategies that helped the company stand out in the podcasting industry. He also opens up about successfully exiting the business, navigating the impact of AI, and building a company designed for acquisition. This conversation is packed with valuable insights on entrepreneurship, leadership, resilience, and creating long-term business success. Why would you wait any longer to start living the lifestyle you signed up for? Balance your health, wealth, relationships and business growth. And focus your time and energy and make the most of this year. Let's get into it by clicking here. Troy delves into our guest's startup journey, their perception of success, industry reconsideration, and the pivotal stress point during business expansion. They discuss the joys of small business growth, vital entrepreneurial habits, and strategies for team building, encompassing wins, blunders, and invaluable advice. And a snapshot of the final five Grow A Small Business Questions: What do you think is the hardest thing in growing a small business? Ryan Estes, a former musician and serial entrepreneur, co-founded Kit Caster in 2019 — a podcast booking agency that places startup founders and executives on top podcasts worldwide. When COVID wiped out 95% of his digital marketing agency's clients, Ryan doubled down on Kit Caster, riding the pandemic-era podcasting boom to hit a $2 million annual run rate within just 18 months of launch. The company grew from 3 to 25 employees at its peak, but has since scaled back to around 8–9 as AI-driven efficiencies reduced staffing needs. Ryan credits strategic early-stage lending and a repeatable sales process as key drivers of their rapid growth. Beyond revenue, Ryan defines success by having built a business that allowed him and his wife to be fully present for their children — and remains a strong believer that podcasting, as a medium for human connection and storytelling, will continue to thrive. What's your favorite business book that has helped you the most? Ryan Estes gave a quick and clear answer — "Traction" by Gino Wickman. This book, which focuses on the Entrepreneurial Operating System (EOS), clearly resonated with Ryan as a founder who valued building structured, scalable operations. Given Kit Caster's rapid growth and their goal of building a business to sell, the frameworks in Traction around team alignment, processes, and goal-setting would have been especially relevant. It's a fitting choice for an entrepreneur who emphasized repeatable systems as a key driver of his success. Are there any great podcasts or online learning resources you'd recommend to help grow a small business? Ryan Estes shares that his top recommendation is his own podcast — "AI for Founders" (aiforfounder.co) — where he interviews founders who are building AI companies or building with AI. With around 47,000 subscribers and growing quickly, the show covers not just business metrics and KPIs, but also the emotional side of navigating the AI era as a founder. Beyond his own podcast, he also recommends the "All In" podcast to stay updated on what top investors and billionaires are thinking. He additionally highlights the content from Alex and Leila Hormozi — early Kit Caster clients — praising their mastery of podcasting and the phenomenal growth they've achieved. What tool or resource would you recommend to grow a small business? Ryan Estes shares that his top tool recommendation to grow a small business is Quad Code. He is enthusiastic about its potential, particularly in the context of AI, and advises small business owners not to feel overwhelmed or behind when it comes to adopting AI tools. He humorously uses a baseball analogy, suggesting that the early adopters will do the hard work of figuring it out, and that within the next six months or so, it will become much more accessible for everyone to simply step in and benefit from it. What advice would you give yourself on day one of starting out in business? Ryan Estes shares that the advice he would give himself on day one of starting out in business is simple yet powerful — "You can do it." He repeats this twice with conviction, reflecting a deep belief in self-confidence and self-trust as the foundation of any entrepreneurial journey. This straightforward but heartfelt message speaks to the self-doubt that many founders face at the beginning, and suggests that believing in yourself is the most important mindset a new business owner can carry with them from day one. Book a 20-minute ...
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