Rob Lingham has been laid off seven times in the last eight years.
Having spent nearly a decade in recruiting, his most recent role pushed him into unfamiliar territory: pitching to investors Some presentations hit the mark. Others fell flat. Over time, he realized the key difference came down to one thing—whether he was leading the conversation or just along for the ride.
Determined to improve, Rob stumbled onto a no-code tool that lets users build functional apps with no programming experience, called Replit. He began experimenting—just for fun. After all, there’s no better way to learn than by executing on a project idea.
A pour-over coffee calculator for his wife, who loved great coffee but could never remember the exact brewing ratios. The app handled everything: water, bean weight, grind size, and time. It was intuitive and simple, just like the tools Rob wished he had when prepping for investor meetings.
After ironing out the details of the coffee app, Rob began work on his most ambitious project yet: Orpheus, a presentation feedback app named after the legendary Greek musician.
The magic of Orpheus was in its simplicity: users pitched their ideas via video chat to an AI-powered system that scored their delivery and offered real-time feedback, like having a personal pitch coach on demand. Rob put the tool to the test himself, refining it again and again.
Then, in October 2024, he took Orpheus to Pitch Party Asheville, where his pitch for the app blew everyone away and earned him the Best Presenter award.
A few months later, Rob came across a job posting from Yoodli, an AI startup building something strikingly similar to Orpheus. He applied, shared his project in the interview, and the CEO joked saying, “I’m not sure whether you should join us or productize this and take it to the moon.” Soon after, Rob became employee #22.
The platform represented a whole new level of interactive learning. Users could immerse themselves in high-stakes conversations by customizing AI roleplays to match any scenario from sales calls to tougher investor meetings. What sets it apart is adaptability: the AI adjusts in real time, challenges assumptions, and offers instant coaching. Even high-pressure environments like college admissions panels or corporate board interviews were within reach.
What set the platform apart wasn’t just the range of situations—it was the adaptability. The AI could respond to your answers, shift its approach based on your delivery, and even pause mid-conversation to offer real-time coaching or feedback.
One of Rob’s latest projects was to build a training program inside the product to help internal teams get up to speed. Think about that for a second: an AI company using AI to train its own employees on how to talk about its product—an AI tool. It’s hard to imagine a more exciting look at the future.
What makes Rob’s journey remarkable isn’t just the tech he built—it’s how it all started: at his kitchen table on a quiet Saturday, building an app to sharpen his own skills. That self-driven project snowballed. He pitched it at Hatch’s Pitch Party, landed a role at Yoodli, and now helps others master high-stakes conversations.
Ever the recruiter, Rob wants you to know: Yoodli just closed a successful Series A and they’re hiring!
Full circle. And seriously inspiring.
Written in Collaboration with Issac Dunn