Dr. Ashley Benne - Rue Four

Ashley grew up wanting to be a surgeon since she was eight years old, came from a family of surgeons, and eventually became one. Then she walked away to build a startup.In this episode, Ashley, co-founder of Rue Four, joins Kevin Jurovich to talk about one of the more unconventional founder origin stories you'll hear. After years practicing as a reconstructive hand and burn surgeon, Ashley became frustrated with the fragmented, paper-heavy systems that consumed clinical time better spent on patients. Her first solution was a no-code app that looked better than an Excel spreadsheet. That MVP became the foundation of Rue Four, a software platform built to help medical practices manage operations, finance, and communication through a single tool.The early days were anything but smooth. Ashley spent weeks walking up and down Fifth Avenue in negative five degree weather, knocking on clinic doors and getting turned away nine times out of ten. She started paying for lunch-and-learns just to get five minutes in front of a surgeon. Eventually, a plastic surgeon on the Upper East Side listened, walked through the product with her, and wrote a $50,000 check. That first outside bet was enough for Ashley to leave medicine two months later and go all in.Her co-founder is her sister, Jessica, a former CNN journalist who brings the storytelling and vision to balance Ashley's operational focus. The two grew up moving across Germany, California, Mexico, and Spain, which built a level of trust that proved useful when investor conversations turned to questions about founding with a sibling. Ashley's approach was simple: she waited until investors were already 20 steps in before mentioning they were sisters.Ashley also opens up about the hiring mistakes every early-stage founder makes, the product direction pivots that came from approaching the market from the wrong angle, and why she cold-messaged the former CTO of Uber on LinkedIn to get help building an engineering team. Her read on the whole journey comes down to one word: perseverance. Not inspiration, not timing. Just showing up every day, especially the days when nothing is working.This season is supported by Perkins Coie. Perkins Coie is a leading international law firm known for providing high-value, strategic solutions. The Emerging Companies and Venture Capital team counsels startups and the investors who back them, supporting clients from formation to exit. In the past three years, clients have raised more than $23 billion in private markets between the pre-seed and growth stages. Perkins Coie combines tailored counsel with sector experience, so when it's time to accelerate, whether for the next financing round, a strategic deal, or going public, your team is ready. To learn more, visit perkinscoie.com