Intro: Alan Rich, a lifelong entrepreneur, is likely best known as the former Founder and CEO of Elite Information Systems, a company that was acquired by Thomson Reuters, as well as later being a Founder and CEO of Chrome River, which was acquired by Emburse in a transaction valued at approximately $520 million. He has now found a way to come full circle in his experience as a company builder, which started with him working side by side with his father. Today, he’s the CEO of Y Meadows, a company that not only delivers an AI-driven solution to customer support teams but that he enjoys running alongside his own sons.

Sitting down with Alan, I not only learned about his unique story in the founding and sale of Elite Information Systems—twice, to two different publicly held companies, the last of which was Thomson Reuters—but Alan also shared his joy for product development as a key motive behind his continually lit entrepreneurial flame. As one might expect, Alan imparted several nuggets of advice on what to do when starting a company, but he also shared what he described as “near-death” experiences (for his companies) along the way.

Don’t mistake Alan’s mild-mannered delivery in our discussion for indifference to the outcome of his several companies; rather, in this interviewer’s opinion, it reflects his humility, peace with the process, and gratefulness for being afforded the ability to create at the highest levels. I hope you enjoy our conversation.

As usual, if you find this conversation helpful, please share with other aspiring entrepreneurs/company builders, and follow along as there are more stories to come.

Onward ~

Pete

2:06 -- Early Influences & Family Business

5:53 -- Transitioning family business to legal software company

12:03 -- Building Elite, Inc., the value of strategic partnerships and consultants

17:59 -- At approximately 150 employees, Elite is acquired by publicly traded Broadway & Seymour, which Elite later divest and operates independently.

23:55 -- Life after acquisition and new ventures, Chrome River

29:42 -- One key motive behind Alan's continued success and entrepreneurial drive

31:04 -- Facing challenges and near-death company experiences

36:04 -- Decision to raise capital 5 years in.

44:01 -- The difficulty in crossing the chasm from a company that sells to professional services customers to now one that also needs to sell to corporations; enter near death experience #2; ultimately succeeding and counting among its customers Cargill, Toyota, Liberty Mutual, etc.

51:26 -- How to overcome major competitors

54:11 -- Next company, Y Meadows, coming full circle and keeping it in the family!