The UpFlip Podcast

234. From a Broke College Student to a $500K/Year Pop-Up Food Business

April 13, 2026·29 min
Episode Description from the Publisher

Most people only eat funnel cake once or twice a year at a fair, but Cheyenne loved them so much she would buy expensive amusement park tickets just to get her fix. Tired of driving out of her community to satisfy a craving, she launched a makeshift funnel cake pop-up shop in her front yard with just a tent, a fryer, and a $5 menu. Today, that front-yard Startup is Fun Diggity, a dessert brand generating $350,000 a year in revenue.In this episode, Cheyenne shares her incredible Entrepreneurship journey, moving from a struggling college student (and former Miss Compton) to the founder of a highly profitable Retail Goods business. You will learn how she leveraged "YouTube University" to teach herself the food business, how she used hyper-local Digital marketing and Instagram to build a cult following without spending a dime on ads, and her step-by-step process for pivoting into e-commerce during the pandemic.In this episode, you'll learn:The "Sink or Swim" Launch: Why launching a makeshift, imperfect business on the 4th of July taught Cheyenne everything she needed to know about product-market fit.The Social Media Differentiator: How posting daily, "uncut" behind-the-scenes videos of her cooking process separated her from faceless competitors and built a massive local community.Overcoming Imposter Syndrome: Cheyenne’s strategy for acknowledging self-doubt—especially regarding money—and using personal development to build the confidence to scale.The Pandemic Pivot: How to transition from a physical pop-up shop into a packaged e-commerce product, including how to find and negotiate with a manufacturer for your first small run.The Power of Authentic Networking: How passing out fliers in a Raising Cane’s drive-thru line led to a massive catering deal with Top Dawg Entertainment (TDE) and Kendrick Lamar.Tags: Side Hustle, Retail Goods, Startup, Entrepreneurship, Digital marketing, Niche MarketsResources:Grow your business today:  https://links.upflip.com/the-business-startup-and-growth-blueprint-podcast Follow Our Second Channel Here: https://next.upflip.com/spotify Connect with Cheyenne: https://www.instagram.com/p/CNkhBQUs7dq/

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