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Underserved

Ep. 114, Unicorn Cavalry

Underserved

Andrew Gelina

Society & Culture, Technology

5.01K Ratings

🗓️ 15 April 2024

⏱️ 41 minutes

🧾️ Download transcript

Summary

Philosophy major Jason "Mac" Macauley found his way into the industry via content moderation. He caught the coding bug when he realized that his love of logic translated well. He aimed to be an "Employee number less than 10" at a startup, cash out, and teach philosophy. After a few years, he came to terms with being a professional software developer and aimed for the next challenge - managing people. We talk about working yourself out of a job, outcome-driven sales approaches, and why golf is not a game of perfect.
Links:
Merrimac CC (Where I shot the 4 under on the back 9) - https://merrimackvalleygolfclub.com/

Transcript

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0:00.0

Welcome everyone to episode number 114 of Underserved.

0:05.0

Joining me today in studio is Jason Mack, McCauley, a technology leader in the Boston area.

0:11.0

Let's get started.

0:12.0

Welcome to this week's edition of Underserved, the podcast for the rest of the tech industry,

0:20.0

where we focus on stories of tech industry leaders

0:22.9

their insights and their lessons learned and now your host andrew jelinea

0:29.9

mac thank you so much for joining us today on underserved well thanks for, thanks for having me. Very excited to be here today. So way back in the day when you were at a tender young age, you really weren't that into technology, were you? Didn't really have access to it. You know, grew up not necessarily wealthy back at the 80s. Having a computer in your house was a luxury item. Were you in upstate New York? Yes. I grew up in upstate New York. Well, I grew up until I was about 10 in Williamstown, Massachusetts, the very corner of the Berkshires up on the top there. And then my mother married a dairy farmer and we moved to upstate New York. I went to a five-town consolidated high school and graduated the class of 51. And the only computer in the entire building was the one that was in the library. And only the librarian was allowed to touch it. Sounds about right. You went from rural to more rural. That's hard to do. Yeah. Yeah, that's very tough to do. It was always exciting to go back to Williamstown where there were actual humans

1:27.9

around instead of just trees. Now, were you in the service at all? Yes. Did six years in the guard,

1:32.7

so Army infantry. And after you got out of there, I imagine you might as well leverage that into

1:37.8

a college education. It was at the same time, actually, luckily. So I signed up for, you know,

1:43.2

the military in order to pay for college because my step family wasn't necessarily pro college, so I had to find a way to pay for it. Yeah, the military was the way. Where'd you go to college? I went to North Adams State College, which is now known as Massachusetts College of Liberal Arts. They actually changed the name of the college. I think it was about two years after I graduated and got a fun little thing in the mail saying, you know, for $50, I can have my degree swap to the new name. I declined.

2:08.9

Okay. And what were you studying up there in North Adams? So my freshman year was undeclared and sort of casting about for what I wanted to do with my life. And I took philosophy 101 and fell in love. You know, out of 120 credits for a degree, I took 78 credits worth of philosophy. Ran the college out of courses and just started building my own. So I did a bunch of independent studies as well around the ethics of punishment, one on anarchy, actually, and, you know, a few other sort of interesting areas that I wanted to dig into. It actually led to one of the more rewarding things that I've ever been paid to do. After I graduated, one of my friends and professor had to have heart surgery and asked me to come in teachers, 100-level philosophy classes for him. What was the idea with the end game? Were you going to become a professor? That was a hundred

2:51.0

percent the end game. All I ever wanted to be was a philosophy professor, just settling down to

2:55.5

academia, writing books, and teaching. It's interesting because the beginning of part of my career was

3:00.6

me really trying to hit a second startup so that I could retire, go back at my PhD and teach philosophy.

3:06.1

Engineering wasn't even the goal once I was an engineer.

3:08.8

So you get out of school, you get your first job. Was that at a place called tripod? Well, so I had a

3:13.5

couple of things before that, just a couple of small things. The thing they're really built confidence

3:18.1

for me in the computer space. So while I was in college, my girlfriend who became my first wife

3:23.3

bought a computer.

3:24.5

And they just made complete sense to me, right?

3:27.2

They only do what you tell them to do, and you can't break them in any way that you can't fix.

...

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