When I Was 17: Logan Sears

17-year old Logan before he hit his self-described "Fallout Boy emo phase"

​Logan Sears is a senior software developer at Brandfolder, which he explains far better than I could, while managing to reference Star Wars. Logan’s career path is full of more twists and turns than most (Craigslist plays a surprising role), but that in itself is a testament to his openness, curiosity, and willingness to say yes to things most people would turn down. Our conversation has been edited for length and clarity.

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​When you were 17, what did you want to be?
 
I always wanted to do something in the tech world. I wanted to make video games because I love playing them, I love game theory. And then I tried to teach myself programming and I thought I hated programming. I tried to pick it up throughout high school and I never could. I just didn't get it.

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Instead, I was heading down the medical school route, going to school to be a doctor. Honestly, it was for the money and prestige aspects and I didn't know what else I wanted to do. I figured, a doctor helps people, that's great; and I liked biology and science the most out of all my subjects in school.  But I learned that I didn't like that either once I actually tried that route.
 
Why did you decide to attend community college? 
 
I was home-schooled up until sixth grade. The education system in Rockford, Illinois is one of the worst in the country, so my parents ponied up the money to put me and my brother into a private, college prep school. It was a very small school, 80 kids in my class. It was very focused on academics, on what you were going to do with your life. There was a stigma that if you weren't going to college after high school, you were basically a bum.
 
But I didn't apply to any [four-year] colleges because I didn't know what I wanted to do. We had money issues growing up, and on top of that, they spent extra money to put us in a private school. I didn't want to burden [my parents] with college too. I couldn't justify [paying] 25 grand a year, when I didn't even know if it was going to be worth it.
 
So I went to this community college, Rock Valley College. I figured I'd get an associate's in something and then transfer. I was still going with the idea of medical school. I liked science, but I wasn't sure I really wanted to become a doctor and put myself through eight to 12 more years of school, and it's really expensive. And if I got burnt out halfway through, I would be stuck with that debt, and you can't just Google the rest and teach yourself surgery and phone it in when you get to the hospital.
 
I did mostly gen eds and then I started thinking that if I didn't know what I wanted to do with my life, I should probably just start thinking about where I wanted to live and what kind of lifestyle did I want to have. I loved Colorado, I'd been there a few times growing up and I love snowboarding, so I decided to move there. The plan was to get an associate's at Rock Valley and then move to Colorado and try to join ski patrol while I figured my shit out.
 
One thing I learned was that ski patrol and paramedics have the same basic training. If you become an EMT, you get a leg up for going into the ski patrol; there's high competition because everyone wants to do that because you get to ski for free every day. So the first year of college I did a rigorous EMT training course. I had to do ER clinical trials and it cemented into my mind that I did not want to work in a hospital - I did not have the stomach for it. People coming in and coding and you just see some gross stuff and it wasn't my jam.
 
I got EMT certified and I decided that I had enough gen eds and I wanted to go to Colorado and check out the ski bum thing. I decided to take year off of trying to figure out my grand plan and just live and work in Colorado. So I moved to Boulder with a plan of getting in-state residency and then going back to college in a year. My philosophy was, I’ll never know less than I know now, so the longer I can wait on any major life decisions, the better choice I can make later.
 
How did you get where you are now?
 
I moved to Boulder and I barely broke even paying rent and bills. I took the first job I could find because I was running out of money very quickly.  I did telemarketing for two weeks, but I quit that job - that job sucked. I ended up working part-time and then moving to a full-time position at Barnes and Noble, of all things.
 
[After a while], I just didn't want to do odd jobs and then hope I struck gold and could go back to college; I still wanted to move forward and better myself. I was always looking for opportunities and one of the things that came up was a job in IT tech support at IBM (which sounds way cooler than it actually was). It was all self-taught at that point. I'm really good with computers, I love technology, I had tinkered with computers all my life. I built my own computers in high school, and I grew up not being afraid of technology and embraced it. That job was more of a call center, but at least it gave me actual job experience in the tech industry.
 
Once I got [Colorado] residency, I wanted to go back to school. I was still trying to figure out what I wanted to do and one of my co-workers was working at IBM part-time and going to school for 3D digital animation. I thought, “That's super cool, that's techy, I love animation and stuff like that. Let me try that.”
 
I started taking some art classes at Front Range Community College. Then I was going to move to Denver and do this two-year accelerated digital animation program. I'm a terrible artist, it turns out, horrible, so bad. But a weird turn of events happened, which involves meeting a guy on Craigslist who got me a job at a sweet, small company called UniFocus doing software QA.
 
I was super broke and I needed a new computer monitor. I was scrounging Craigslist trying to buy a cheap monitor for 50 bucks, and found this guy in Denver who was selling one. So I drove all the way to Denver, an hour and half through traffic, and gave him 50 bucks for this monitor.
           
He was cool and we chatted for a bit. He seemed like he was really stressed and busy with work. We were talking about it and he saw my IBM badge and I told him I did tech support stuff. He didn't really say anything, but Craigslist people are weird. I gave him 50 bucks, he gave me the monitor, I drove home, plugged it in, and it was broken.
 
That was probably close to my last $50. It sucked. Doing my IT tech support stuff, I tried to troubleshoot this monitor, switched all this stuff, did a bunch of tech stuff, and then I emailed this guy. I said, “Look, I know this is a Craigslist deal and you have no reason to give me my money back, but here are the things I did to try fix the monitor and it's definitely not my computer, and I was wondering if I could bring you back the monitor and exchange it for my $50 back.” He emailed me
back and he was so impressed with my troubleshooting steps that he said, “How about I give you your $50 back, you keep the monitor, and would you like a job?”
 
He was a software developer at a small company outside of Denver, UniFocus, and they needed someone to do software quality assurance, which involves testing whatever app they're building, writing out test cases, basically doing what I did in the email that I had sent him. I drove down to Denver a few days later and interviewed with them, and it went well.
 
This was a month before I was going to move to Denver to do this animation program. I had to decide to either get real work experience now for the same money I would hope to make getting out of this program, or go to this program and gamble that in two years it would be worth it. I dropped out of the program before it even started, and went to work for this company.
 
I worked there for about nine months. I was exposed to programming again, and this time, there were all these people around me that understood coding and could actually explain it. Then, the same guy who got me that job told me about a six-month coding boot camp.
 
I had already missed the deadline for this program, but I signed up anyway. They had someone drop out last minute and a spot opened up. Coming out, I knew how to program which was what I had wanted to be able to do since I was in high school. I was offered a job by a startup in Denver called iTriage in the last month of the program. This was a medical startup that had an app that was kind of like WebMD, but instead of just telling you, “You have cancer and you're going to die,” it actually tells you where you should go for the appropriate care based on your symptoms. Like, “You have a fever and flu symptoms. Go to Walgreens, it'll cost you $20.” Not only that, it would open up your map app and give you turn by turn directions to Walgreens with store hours and everything.
 
So I was programming a medical app to help people with symptoms to get to where they needed to go, to get help. It felt like I was doing the doctor thing again without actually having to be in the ER, which was nice. I was there for two years, and then iTriage got bought by Aetna, an insurance company. And I've been working for another startup in Denver ever since, Brandfolder.
 
Brandfolder does visual asset management, which is a mouthful, but it's essentially a combination between Dropbox and digital brand management. We make it easy to share your creative assets to get around email file size limits, and make sure that your brand is represented exactly as it should be across the world, which is actually a big deal to large companies.
 
For example, when the new Star Wars movie came out [two years ago], they had the new droid, BB-8, that was made by a tiny startup in Boulder, Colorado named Sphero. No one had ever heard of them before, and they had a marketing team of two people. Suddenly, the world found about this new BB-8 droid, everyone loves it and they want to find out who made it and how they can get one. The entire world was slamming this two-person marketing team asking for their logo to put in The New York Times and Time magazine. If Sphero had sent the wrong zip file, then the wrong logo gets put in The New York Times and you’ve basically ruined your brand identity. Our site and our app actually automate that entire work, and all the publications can get what they need there and they can always guarantee it's the most up-to-date, accurate logo.
 
I do want to go back to school [at some point], but not because I feel like I need to. Brandfolder is doing really well right now, and I've seen it grow and I believe in the product and where it's going. I want to be a part of it. If I go back to school, it's going to be for something that I'm actually interested in learning, without the pressure of feeling like I need to do this to succeed in life.
 
Looking back, what seems clear to you now? 
 
I should have bought more Bitcoin [laughs].
 
I feel like, I was very on edge all the time because the story I just told you is all over the place. I'm glad I made those decisions, but I wish I had had more confidence in myself. What I learned is, if a door opens, walk through it. The reward is greater than the risk of walking through a wrong door or making a wrong choice.
 
And I would say, don't rush it. Everyone makes college out to be this big, life-changing event, where you have to make the right choice or you're screwed. I don't think that's the case in reality. If you're not sure what you want to do, you don't have to make the decision right away. I think there's this misconception that people think they've gone so far down a certain path that it's too late to turn back, and I don't think it ever is. I'm glad I didn't fall into the pressure of my classmates who just went to business school and now most of them aren't even doing jobs that actually correlate to their degrees necessarily.
 
If you want to go to school and learn something for your own good, absolutely do it. But don't feel like it's going to be necessary to get a job or save your life. Worst case scenario, I can always go back to working at Barnes and Noble. ​