The world of sports is not just about physical prowess or competition; it’s an incubator for leadership qualities such as discipline, teamwork, strategic planning, and resilience. Athletes, from amateur levels to professional arenas, often encounter situations that test their limits and require them to step up in ways that mirror the challenges faced by leaders in various fields.
As part of this series, we had the pleasure of interviewing Ajay Chawla.
Ajay Chawla is founder and CEO of OnTrac AI, where he leads the company’s mission to deliver next-generation AI and machine learning solutions integrated into clients’ business processes. With more than 27 years of experience across technology, operations, and business development, Ajay previously held senior leadership roles at JTEK Data Solutions and SourceHOV, delivering high-impact results in complex, data-driven environments. He co-founded Toast for Tykes in 1999, a Michigan nonprofit dedicated to pediatric causes, and has helped raise hundreds of thousands of dollars for organizations including the Children’s Hospital of Michigan and Kids Kicking Cancer. A lifelong athlete, Ajay is the current head coach of Brother Rice Varsity Lacrosse, mentoring the next generation of student-athletes at his alma mater. He earned his degree from Marymount University, where he competed as a collegiate lacrosse player.
Thank you so much for joining us in this interview series. Before we dive in, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career? What athletics did you participate in?
I grew up in Michigan and played lacrosse at Brother Rice High School. After high school, I played three years of NCAA Division 3 lacrosse at Marymount University in Virginia. I’ve been in the technology industry since I graduated from college, first in outsourcing business processes, then in the software industry and the dot-com industry, always on the cutting edge of technology. In 2018, I started working more with robotic process automation, which led to the next breakthrough in technology in AI. I realized that AI was going to change the way people worked and lived, and I wanted to be part of this emerging technology.
Can you share the most interesting story that happened to you since you started your career?
In early 2000, I moved to San Francisco to chase the dot-com boom. I joined a company called 1stup.com that was backed by one of the largest private equity firms at the time. Those first 11 months were incredible. We worked hard and played harder. The office would throw anniversary parties, happy hours and Bloody Mary breakfasts on Friday mornings before work. It was everything you’d imagine a dot-com to be. About 80% of the office was there until 9 or 10 p.m. every night, and we were all in our 20s. It was an absolute blast. Then came November 7, 2001. We got the news that the private equity firm was defunding us. Overnight, we went from this thriving company to laying off 160 people. What really stuck with me is that we thought we were thriving, but we were burning cash like every other company. We had no revenue. Zero. Within four weeks of our severance, my four roommates and I, all working for different companies in our five-bedroom San Francisco apartment, were all unemployed. That experience taught me the critical lesson that cash flow is everything. An influx of AI startups has launched in the last year and a half, and about 90% won’t survive. They’re all living on venture dollars and investment dollars, but at the end of the day, you have to have revenue to get to cash flow positive and support long-term growth. The parties are fun, but you’ve got to make money.
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