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Jamon Holmgren

Ten Years

Published August 1, 2015

I sat down at my desk in my spare bedroom and logged into my Windows XP home-built computer. Two seventy pound Sony Trinitron 21” CRT monitors stared back at me on my $10 folding table, and I pulled up my new Gmail account to see what my first project would be. On the floor, my new 7 month old boy was laying on a blanket and smiling up at me.

It was exactly ten years ago -- August 1, 2005, my first official day working for myself -- and my uncle Ed was my first customer.

The Architectural Designer: 2005 - 2006

My first project was a new home design, with 3D renderings. I had been practicing with Chief Architect 10 for a couple months, so I knew the basics. And of course my previous job had involved CAD work for New Tradition Homes, a regional home builder in the area.

My invoice (to Ed) for the whole month of August, 2005, was for $1,113.70. After getting a nice paycheck for three years from New Tradition, this was a big wakeup call. It was up to me to make things happen now.

But 3D home design was a lot of fun. In 2005, home building was a mad dash, and everyone was throwing money around for anything house-related. As some of the first home designers to do 3D renderings in our area, Ed and I were inundated with work. We kept raising our prices and kept getting projects. Ludicrous 8,000 square foot concepts crossed our desks, and everybody had wild dreams and lots of credit.

I even got a chance to design a huge Lake Oswego remodel for then-GM of the Portland Trail Blazers, Kevin Pritchard. I was an avid Blazer fan, so Chyra and I got skybox tickets every couple weeks.

The Web “Designer”: 2006 - 2007

Home design paid the bills (after the first few shaky months) and I enjoyed it, but I’d always been fascinated by programming. I’d spent way too much time building games in QBasic on my parents’ computers in middle school and high school, and the idea of getting paid to code sounded pretty good to me.

Armed with a copy of Dreamweaver MX 2004, a book on PHP 5 and MySQL, and another one on JavaScript, I started marketing my web design services to local business owners that I knew. With a low rate of $45/hour, it was still surprisingly hard to convince people they should use me. But I slowly built my clientele list, one $1500 website after another.

My first websites were so, so awful. It wasn’t really the code; they were simple websites, and I’d always been a clean coder. But I also did the design (using Paint Shop Pro 9). Luckily, expectations were low.

The Recession Survivor: 2007 - 2009

I was feeling pretty good. My income wasn’t great, but I was paying the bills. And if I could just string together a few good months in a row, I’d be doing a lot more than that.

Then, in April of 2007, the home design work just cut off. Ed barely had enough design work for himself, much less any to send to me. I sat staring at an empty inbox for a couple days, then made the decision. Time to go out and sell.

I learned a lot about sales doing cold calling. It sucked, for one thing. I was able to keep things running, though, through sheer force of will, and by the beginning of 2009 I decided that things were going well enough to get an office and maybe an employee or two.

The Workaholic: 2009 - 2011

I rented a spare office from New Tradition in their nice new building, and hired a few inexperienced employees. I also built a PHP framework called phpGenesis that allowed us to build websites very quickly. My clientele grew by word of mouth and SEO efforts and I started taking on more complex projects, including a sales CRM and a manufacturing system for a local cabinet shop. I also built my own invoicing, time tracking, and project management system, and landed a few larger sales. We were up to about 7 employees.

We were making good money, finally. But I was putting in way too much time in the office. My wife had two small children at home and I was working 9 AM to nearly midnight every day.

It was a rough time for both of us. And by mid-2011, I was tired of it.

The Rails Developer: 2011

I started hiring more people and delegating more, and getting to go home a bit earlier. One of my hires was Daniel Berkompas, a young but talented developer who was also going to law school. Daniel kept telling me that we should be using Macs and doing Ruby on Rails. I had dabbled with Rails, but my PHP framework was just so easy to learn and fast to build websites in.

But we weren’t just building websites. We had web applications to code, and the framework just wasn’t designed to handle those. After a few bad experiences building large code bases in phpGenesis, I decided to try our next website in Rails. Daniel led the project and it was a resounding success.

I resolved to use Ruby on Rails as often as we could from then on. I even bought a MacBook Pro, and loved it. Some of my longer-term employees weren’t happy with this decision, but over time Rails (and Macs) won them over too.

The iOS Developer: 2012 - 2013

In 2011-2012, iPads were all the rage. I bought one for “research” and started playing around with Xcode and Objective-C. We built a few PhoneGap apps and found that it was hard to get them to live up to their promise.

Then, in mid-2012, someone emailed about building an iPhone and iPad app, coupled with a web application.

This was our chance. There was a new product that had just come out, called RubyMotion, and I liked the idea of building the iPhone, iPad, and Rails apps all in Ruby. So I submitted a quote and secured the sale.

Silas Matson (one of my young developers) and I started working on it. I knew enough about iOS development by that point to get basic things to work, but it was slow going. So I started working on a new RubyMotion code library to speed things up, called ProMotion.

Turns out, lots of people needed to speed up their iPhone development workflow. ProMotion started getting quite popular, and I even got invited to speak at a few conferences and meetups.

During all this time, I was right in the thick of things, coding every day and helping my employees get through problems. It was fun but exhausting.

The Owner: 2014

I was ready to stop coding and start running my business. As it happened, a designer I respected greatly was interested in coming to work for me. Mike Waszazak joined the team as my Creative Director and a new era was born.

Mike had run his own business before. He was the right balance of knowledgeable, authoritative, and yet respectful of me and my business that I had worked so hard on. He raised the bar for everyone, including me, and helped me develop all parts of the business, not just the design department.

Then, in January 2015 Mike left to go back to his previous position as Communications Director at New Heights Church in the area. It was a big loss, but with Mike’s help we were headed in the right direction and the team felt cohesive and solid.

The Future: 2015 - ?

And so here we are. My little boy is now 10 years old and has three younger sisters to look after. I’ve managed to reduce my workdays to a more reasonable 9 hours per day. And there are some very exciting things in the works that I’m looking forward to announcing soon.

(Note: here is that announcement!)

It’s been an awesome ten years. I’ve learned so much. I’ve had exhilarating days where I would call my wife in the middle of the day just bouncing with excitement, and had horrible days where I couldn’t meet anyone’s expectations. I’ve had opportunities pass me by, and had others hit me right on. I’ve had great mentors and colleagues and awesome employees.


Despite my blog post headings looking like it’s all about me, I’d never have done it without my great employees and contractors and others. It’s a bit corny and sappy, I’ll admit, but this is my favorite part of this blog post.

Thank you to the following people for spending at least some part of your life working for my little endeavor. It still means a lot to me. (If I missed anyone it’s my fault, not yours.)

Daniel Berkompas, Drew Holmgren, Isaac Holmgren, Lucas Holmgren, Meredith Wuori, Michael Berkompas, Mike Waszazak, Nick Kandoll, Shane Holmgren, Jessica Hori, Karl Von Der Luft, AJ Robertson, Carlin Isaacson, Denton Holmgren, Jed Bartausky, Justin Huskey, Kevin VanGelder, Leon Kim, Ryan Linton, Silas Matson, Yulian Glukhenko, Zachary Berkompas.

Contractors, professionals, mentors, and just a few of my awesome clients, in no particular order, who gave me a leg up at just the right time:

Ed Holmgren, Phil Wilson, Bill Brassfield, Alice Johnson, Tim Sutinen, Josh Barrett, Julie Olson, Kelly Helmes, Amy Ruth, Lars Jarvi, Stacey Olson, Tim Haskins, Patrick Ezell, Chuck Bond, Jonathan Johnson, Jim Larsen, Todd Werth, Ken Miller, Mark Rickert, Gant Laborde, Laurent Sansonetti, Colin TA Gray, Tom Berkompas, Tim Santeford, Jeff Held, Ryan Kandoll, Ron and Elizabeth Holmgren (dad and mom), William Roselli (RIP)

And of course, last but certainly not least, my long-suffering and gorgeous wife Chyra, for putting up with all those long workdays, and my four cute kids for always running to meet me at the door whenever I got home before their bedtimes.