Ep 11 - Rob Reesor: Insights, Tips, Tricks and Wisdom from a Tech Veteran
Episode Summary
Rob Reesor shares his four-decade technology career journey from early AI expert systems at Intellicorp through pioneering e-commerce at Virtual Vineyards to executive leadership roles across multiple private equity-backed companies. He discusses the evolution of software development, the challenges of technical debt management, building trust with non-technical stakeholders, and navigating acquisitions while emphasizing transparency and team empowerment.
Key Quotes
"I was the first person to ever use Wells Fargo's payment gateway and build something against it. I was the first person to build server-side Java code—I didn't know it wasn't made for that, so I did it anyway."
"One of the hardest jobs in software is product management. Trying to figure out what the customer wants, what the market will accept, what the competition is doing, and then get a development team to get it out the door as quickly as possible."
"Hire great people, arm them to the teeth, and get out of their way. That's exactly what my best boss did, and that's what I've tried to do in my career."
Transcript
Hi welcome to Tales From The Sky Lounge, a podcast about business consulting and venture investing. We get out there in the world, we talk to people who are making it happen and we get their stories. If you could hit like and subscribe it really helps us get our message out.
So today's guest in the Sky Lounge is Rob Reeser. Hi Rob.
Hey Todd, how are you? Great to have you in the Sky Lounge.
Great to talk to you again. Yeah, good thanks, you too. Well, why don't you give us a little bit of introduction? Who are you?
Yeah, I can do that. If I go back a number of years, probably I was one of these folks in high school who had no idea what they wanted to do. I could ace all my tests and my classes without opening a book, so I never learned how to study. When I got out of high school I didn't have a clue what I wanted to do. So very shortly out of high school I got married, bought a house, started working. After about four years I realized that I had four different jobs and I was still making minimum wage. So I thought, well maybe it's time to get an education. I went off to University of Oregon just because I happened to be in the town we were living in. I started focusing on business and sociology, kind of labor sociology. I was very interested in labor relations, having had a kind of a weird experience at a little company I was working for.
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