From Princess Parties to AI Systems: How Hayley Henning Scaled Characters.io Without a Marketing Budget | Episode 347
Mon Aug 25 2025
Hayley Henning didn’t wait. She learned. She acted. She built Characters.io from a broke college hustle to a scalable AI-powered brand. In this episode of The AI-Powered Marketing Show, host Keith Bell sits down with Hayley to unpack her journey—from Craigslist gigs and a DIY Cinderella costume to a full-blown, systemized entertainment business with national reach and zero fluff.
She tells the truth. Marketing in 2009 felt different. SEO meant directories. Tactics leaned black-hat. Money didn’t exist. So she bootstrapped. Her mom made her costume. She listed services. She waited for calls. Then, one day, the call came—and everything changed.
Keith asks the real questions. How did she validate the idea? What broke? What worked? What stayed? Hayley walks us through it. She didn’t just dress up. She built processes. She streamlined booking. She reduced errors. She gave performers structure. She used Make—not Zapier—to automate the chaos. With 100+ automation scenarios running her back office, Hayley explains why her AI agent now custom-quotes events, factors in travel, and triggers team chats.
We go deep. We explore the rise of answer engine optimization. We compare Claude and ChatGPT. We question Google Ads. We unpack tiered pricing ladders and how transparency, not pressure, helps customers upgrade.
For creators, solopreneurs, and marketers scaling real-world service businesses with limited time and money—this is a masterclass.
Listen in. Learn how systems save sanity. See what marketing looked like before filters. And discover why Hayley’s story is your blueprint—if you’re building with purpose, precision, and a bit of sparkle.
🧠 Want more? Join the community at patreon.com/Ai_Powered_Marketing_Show for behind-the-scenes workflows, bonus episodes, and automation templates that save time without losing the human touch.
🔗 Start automating today with your free trial at Make.com.
More
Hayley Henning didn’t wait. She learned. She acted. She built Characters.io from a broke college hustle to a scalable AI-powered brand. In this episode of The AI-Powered Marketing Show, host Keith Bell sits down with Hayley to unpack her journey—from Craigslist gigs and a DIY Cinderella costume to a full-blown, systemized entertainment business with national reach and zero fluff. She tells the truth. Marketing in 2009 felt different. SEO meant directories. Tactics leaned black-hat. Money didn’t exist. So she bootstrapped. Her mom made her costume. She listed services. She waited for calls. Then, one day, the call came—and everything changed. Keith asks the real questions. How did she validate the idea? What broke? What worked? What stayed? Hayley walks us through it. She didn’t just dress up. She built processes. She streamlined booking. She reduced errors. She gave performers structure. She used Make—not Zapier—to automate the chaos. With 100+ automation scenarios running her back office, Hayley explains why her AI agent now custom-quotes events, factors in travel, and triggers team chats. We go deep. We explore the rise of answer engine optimization. We compare Claude and ChatGPT. We question Google Ads. We unpack tiered pricing ladders and how transparency, not pressure, helps customers upgrade. For creators, solopreneurs, and marketers scaling real-world service businesses with limited time and money—this is a masterclass. Listen in. Learn how systems save sanity. See what marketing looked like before filters. And discover why Hayley’s story is your blueprint—if you’re building with purpose, precision, and a bit of sparkle. 🧠 Want more? Join the community at patreon.com/Ai_Powered_Marketing_Show for behind-the-scenes workflows, bonus episodes, and automation templates that save time without losing the human touch. 🔗 Start automating today with your free trial at Make.com.