Insights, Tips, Tricks and Wisdom from a Tech Veteran | Rob Reesor, Ep 11
Episode Summary
Rob Reesor shares his journey from early AI expert systems development at Intellicorp through pioneering e-commerce at Virtual Vineyards to executive technology leadership across multiple private equity-backed companies. He discusses the evolution of software development practices, the challenges of technical debt management, and the critical importance of trust-based leadership in building high-performing engineering teams.
Pull Quotes
On being the first person to build server-side Java code at Virtual Vineyards
“I didn't know it wasn't made for that, so I did it anyway and it seemed to work out.”
“He was willing to give you the rope and let you actually explore and do the work properly. At the end of the day, he just embodied giving people a lot of trust. I came out of that experience feeling that as a developer I was trusted to do my job. I wasn't told how to do it, I wasn't told how long it should take, I didn't have him estimating work for me.”
“Let's stop counting how many bricks we put in the wall because one might be the size of a marble and one might be the size of a boulder and we can't really compare the two.”
On underestimating the complexity of debugging generated X Windows code
“Well, this weekend turned into three months.”
On realizing retirement wasn't about leaving work entirely, just leaving the wrong work
“I was confused between stopping doing that and stopping doing everything.”
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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