E06 | Built to Last: Alan Rich of Y Meadows on Serial Entrepreneurship, Scaling Software, and Starting Over with AI

Alan Rich has built and exited not one, not two—but three successful software ventures, including his latest startup, Y Meadows. In this episode, he shares a masterclass in long-haul entrepreneurship and what it takes to keep building, even when you've already crossed the finish line—twice.

Alan’s journey begins with founding Elite Information Group alongside his father, building financial systems for law firms before scaling it globally and selling to Thomson Reuters. Then came Chrome River Technologies, a venture into enterprise expense reporting that served clients like Toyota and Exxon. Today, Alan is back in the arena—this time with his two sons—leading Y Meadows, a company using AI to automate customer service and operations.

Through these ventures, Alan has navigated evolving industries, scaling challenges, and the emotional cycles of starting (and restarting) companies. This conversation reveals how he’s kept the passion alive, the lessons he brings into each new venture, and why the sales engine—more than the tech—is the ultimate startup differentiator.

Here’s what’s covered:

• Building three tech companies across decades—and why Alan keeps coming back
• How entrepreneurship became a multi-generational journey
• What selling to Fortune 500s taught him about product-market fit
• Navigating acquisitions, pivots, and exits without burning out
• Why sales is the real engine of any startup
• How AI is reshaping customer service workflows—and what Y Meadows is solving
• Advice for repeat founders looking to re-enter the game with clarity and balance

Learn more about Y Meadows here: https://ymeadows.com