Dr. Ashley Benne - Rue Four

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

Chang "CK" Kim - Saywise

From $510M Exit to AI Startup: The Founder Who Finally Learned to Stop What does it actually cost to build two companies from scratch and sell one for $510 million? For serial founder CK, the price was 20 years without a real break, chronic sleeplessness, and the constant pressure of pretending to have all the answers in every room. In this episode, we go deep on one of the most honest founder journeys you'll hear. From a military-service detour in Korea that accidentally became his real-world MBA, to a Google acquisition, to a nearly decade-long grind that turned 15 employees into millionaires and early investors into 30x returns. Here's what we unpack: How a mandatory military posting launched his career. CK had zero engineering background and zero business training when he landed at a 30-person Korean tech startup during the dot-com boom. He ended up handling fundraising, investor materials, and eventually helped take the company public on the Korean Stock Exchange. "I was grumbling a lot," he admits. "But in hindsight, that was the best real-life MBA I could ever have." Getting acquired by Google, in one of the only countries Google doesn't dominate. Korea is one of just three countries globally where Google doesn't hold majority search market share. Their solution? Buy a content platform. CK and his co-founder had built the leading blogging platform in the country. The deal took nearly a year. He was at the Google Seoul office Monday morning after it closed on a Friday. Nine years. One number. What it actually cost. His second company, a mobile publishing and storytelling platform, took nine years to exit at $510 million. The financial wins were real: 70 employees, roughly 15% became millionaires, Series B investors saw 30x returns. But CK is equally candid about the toll. Ambient stress. Sleepless nights. The performance of certainty even when you have none. "You're supposed to be the smartest person in the room, even though you may not be." The sabbatical that changed everything. After walking away from the acquiring company two years post-deal, CK made a decision the previous version of himself never would have: he took a year and a half off. No plan. No roadmap. Just people, conversations, and the radical act of listening. His wife told him he was a different person. Coming from someone who watched 20 years of nonstop intensity, he took that seriously. Building the platform that listens back. The sabbatical produced the seed of his next company. A friend's thought experiment, "What would you do if a doctor gave you three years to live?", led CK back to the same instinct that drove every company he had ever built: helping people share what they know. His new company, Saywise, uses AI to extract and publish human knowledge through conversation. You talk. The AI listens, asks follow-ups, and turns it into polished content. The antidote to a flooding internet of AI-generated noise. The through line across CK's entire career? Every company he has built has centered on one thing: giving people a platform to express and share knowledge. The only thing the sabbatical changed was who was doing the listening. Whether you are a founder mid-grind, approaching an exit, or wondering what comes after the wire transfer, this conversation is required listening. 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

Sam Gibson - Hadron Energy

Sam Gibson left a stable engineering job in Kansas City with $10,000 in his bank account and a plan to build a miniaturized nuclear power plant. Two and a half years later, his company is merging with a publicly traded entity at a $1.2 billion valuation. The story between those two facts is the one worth telling. A Cold DM and a Calculated Leap The first move Sam Gibson made toward building Hadron Energy was sending a direct message to a founder he had never met. Kevin, a founder himself who makes a point of responding to early-stage builders, got on a phone call with Sam. Then another. Then several more. By July 2024, Sam had packed his car and driven to what he thought was the Bay Area’s promised land. He officially incorporated Hadron Energy there, with roughly $10,000 to his name and no investors yet on the cap table. The first check he received was $2,000. He took it. What Hadron Actually Builds Hadron Energy is developing what Sam calls Lightwater Micromodular Reactors, a compact nuclear power system that produces 10 megawatts of electric output, enough to power 10,000 homes simultaneously. The company is targeting data centers, critical infrastructure, and remote communities as its first customers. “Power is the limiting factor for AI,” Sam said. “When you’re talking to hyperscalers and data centers, that’s the most important thing.” The company is currently merging with GigCapital7, a Special Purpose Acquisition Company (SPAC) with $212 million in trust. Bankers have valued Hadron at $1.2 billion. Sam expects net proceeds of approximately $200 million after what he anticipates will be a low redemption rate, plus an additional private investment in public equity (PIPE) raise he is actively leading. The Builder Behind the Company Sam’s background is in mechanical engineering and engineering leadership. He describes himself as someone who always knew he would start a company and spent years building toward the moment when it made sense to stop preparing and simply move. “There always comes a day when you have to stop studying and just make the jump,” Sam said. “There’s always the analysis paralysis where you get stuck in a loop of doing constant research. There’s something to be said about trusting your instincts.” At 24, Sam leads a team that includes engineers and professionals significantly older than he is. He addresses the age dynamic with a straightforwardness that reflects how he approaches most things. How Survival Became Scale The hardest stretch of the Hadron story is the months between Sam’s first $2,000 check and the point when checks started arriving fast enough to keep the company alive. “I started the company when I had like $10,000 in my bank account,” Sam said. He does not frame those months as a crisis he survived. He frames them as the natural cost of operating at the idea stage in a capital-intensive industry during a difficult fundraising environment. What kept him moving was a belief that persistence in the right direction compounds over time. What the Next Chapter Looks Like Sam’s goals for 2026 center on completing the NASDAQ listing, scaling the engineering team, and making measurable progress on the licensing work. He also wants to build the brand into something recognizable beyond the capital markets audience currently paying attention. 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 [https://perkinscoie.com/]