Built to Sell: How to Scale with Exit Intention w/ Ryan Estes of Kitcaster

Summary

In this episode, Brandon sits down with Ryan Estes, co-founder of Kitcaster, a podcast booking agency recently acquired by Moburst. Ryan shares his dynamic journey from shoveling snow and delivering newspapers as a kid to experimenting with various entrepreneurial ventures—including a health food brokerage and a failed cookie SMS startup—before striking gold with Kitcaster. His path is marked by a blend of curiosity, hard-won experience, and an insatiable drive to build meaningful businesses. At the core of his entrepreneurial philosophy lies the belief that business should be fun, profitable, and of service.

Ryan opens up about the early days of Kitcaster, how COVID-19 created an explosive opportunity in the podcasting world, and the intentional decisions he and his co-founder made to scale the company. He discusses hiring strategies, building company culture, bootstrapping growth, and the systems he built to ensure repeatability. He also shares candid lessons about dealing with copycats, the importance of finding your ideal customer, and the emotional rollercoaster that is startup life. His pragmatic and principled approach to leadership offers a unique blend of vision and discipline.

Toward the end of the episode, Ryan reflects on what it means to be a founder navigating scale, funding, and potential exits. He offers hard-earned advice about when to begin the sales process if you’re building to sell, the intoxicating dangers of success, and the importance of seeking out responsibility instead of shirking it. From practical systems-building to philosophical insights about meaning and consciousness, Ryan’s interview is an honest, high-value masterclass for entrepreneurs at any stage.

Takeaways

1. Start by validating demand before building. Ryan sold Kitcaster to three people before it even existed.
2. Early marketing should start with non-scalable tactics. He personally reached out to founders and leveraged niche apps.
3. Systems and SOPs matter early. Ryan built repeatable processes even before having a team in place.
4. Hire slowly and with intention. He started with contractors and only moved to payroll once the model proved itself.
5. Be hyper-specific about your ICP. Kitcaster targeted funded founders, entrepreneurs with exits, and C-level execs.
6. Stick to your lane. Focusing only on podcast booking allowed Kitcaster to build a bolt-on, sellable service.
7. Culture doesn’t have to mean “family.” Ryan fostered a positive, creative culture while maintaining professional boundaries.
8. Bootstrapping can include strategic borrowing. Stripe loans helped fuel growth—but he cautions against overuse.
9. Operational rigor is key post-hockey stick. When growth slows, tightening systems and automation can preserve margins.
10. Start exit conversations early. Begin the process when you have traction—not when you’re ready to walk away.

Chapters

• [00:01] Childhood Hustles and Early Work Ethic
  • Ryan talks about shoveling snow and delivering newspapers, laying the groundwork for his entrepreneurial spirit.
• [00:41] From Bad Bosses to Becoming a Founder
  • His motivation to become a better leader than the managers he worked under.
• [01:40] Launching His First Company
  • Ryan shares the story of his health food brokerage, New Natural, and the lessons learned.
• [02:57] Founding Kitcaster and Meeting His Co-Founder
  • How a former podcast guest and HR founder became his co-founder for Kitcaster.
• [04:54] Juggling Multiple Ventures and Finding Traction
  • Ryan ran Talklaunch, a social media agency, while testing other ideas like natural deodorant and cookies by SMS.
• [06:53] The COVID Pivot That Changed Everything
  • Kitcaster became the full-time focus after the pandemic wiped out Talklaunch’s revenue.
• [08:31] Validating and Scaling Kitcaster
  • How he validated the idea, got his first customers, and rapidly iterated on marketing strategies.
• [11:20] Systems, Hiring, and Bootstrapping with Intention
  • Ryan discusses building sales scripts, hiring early team members, and scaling through cash flow.
• [14:58] Competition, Copycats, and Creating a Moat
  • How he dealt with competitors mimicking Kitcaster’s messaging and why focus was their competitive advantage.
• [16:57] A Risky Marketing Bet That Paid Off
  • The $2,500 LinkedIn marketing experiment that opened the door to growth.
• [19:13] Building Culture Through Crisis and Camaraderie
  • COVID-era team culture and why he emphasized wholesomeness, creativity, and no podcast emergencies.
• [21:19] Borrowing to Scale and Knowing When to Stop
  • He shares his experience with Stripe loans and the importance of avoiding the debt spiral.
• [22:44] The Post-COVID Shift Toward Operational Tightening
  • Why they chose efficiency over expansion during a market slowdown.
• [24:21] Intentional Culture Without the ‘Family’ Label
  • Balancing professionalism with fun and avoiding the toxicity of faux-family workplace culture.
• [27:25] Funding Knowledge He Wishes He Had Earlier
  • Ryan discusses his struggle understanding funding structures and the value of formal business education.
• [29:16] Founder’s Wisdom: Do the Hard Things First
  • He shares the stoic principles and simple maxims that guide his daily operations.
• [30:36] Caution While Scaling: The Danger of Overexcitement
  • Ryan warns about the intoxicating nature of early success and urges founders to temper spending.
• [32:32] When to Begin the Exit Process
  • Advice to founders to start the sales process earlier than they think if a sale is the end goal.
• [34:27] What Founders Ask—and What They Should
  • He reflects on the kinds of questions founders ask him, and the deeper alignment they should seek.
• [38:13] What He’d Do Differently If Starting Again
  • Ryan would seek out more responsibility earlier and embrace the challenges that come with it.
• [39:57] The Book That Keeps Him Grounded
  • He recommends The Origin of Consciousness in the Breakdown of the Bicameral Mind as an esoteric but inspiring read.