Finding Freedom and Opportunity With WordPress: How Wolf Bishop Overcame Prison and Addiction to Launch a Career

In 2005, Timothy “Wolf” Bishop was serving time in an Iowa prison for charges related to a gambling addiction.

“When I was 25, I made a bet that I could not cover,” Bishop said. “I had gambled with a local thug on a local semi-pro baseball game between the Burlington Bees and the Clinton Lumberkings. I bet on the Bees, who lost the game without even scoring.

“I did not have the $10,000 I had bet. When I told the man I owed this, he was less than happy. He put a gun to my head and told me that if I did not have his cash in one week, he would put a bullet in my brain. I had the money three days later.”

It was the crimes Bishop committed to cover that debt that got him sent to prison. Now an experienced professional, entrepreneur, and educator, who has spoken at numerous WordCamps, he credits WordPress for changing the trajectory of his life and helping him find a place of stability.

“It saved my life,” Bishop said. “I am not being over-dramatic when I say that. If it was not for WordPress, I would either still be in prison or dead.”

During the time Bishop was incarcerated in Rockwell City, the Iowa Department of Corrections began allowing limited internet access to inmates, and he was fortunate enough to be in one of the select prisons. Writing a personal blog was one of the allowed activities, so Bishop went on the hunt for a blogging platform to use. He had already tried many of them, as he had been into open source software since the mid-90’s.

“As I was also fighting to overcome my gambling addiction, I had the idea of starting a blog about my experience as a sort of self-therapy,” he said. “I tried TypePad first, but did not like it. Less than a month later, I discovered WordPress thanks to a correctional officer who had a blog of her own.”

Wolf Bishop in prison in 2005, Rockwell City, IA

The officer had maintained a blog for the past several months and recommended to Bishop that WordPress would be the easiest and best for his needs. This was in the summer of 2005, just a few months after WordPress 1.5 was released with a new “Pages” feature, a better templating system, and the Kubrick default theme.

“I was at a point in my life when I knew that I needed to change, and drastically, or I was going to be in prison for the rest of my life, or worse….dead,” Bishop said. “I know that sounds over dramatic, but I swear it is true. I hoped that by blogging about my battle with addiction, I could better overcome it.”

His first blog launched in September 2005, and he posted weekly for just over one year.

“Prison is a place where hope is in low supply,” Bishop said. “You have to watch your back every minute of every day. Before WordPress, I got in a ton of trouble in prison. I spent a lot of time in the hole. I had nothing to focus my time or energy on, so I fought and walked around with a giant chip on my shoulder.”

At one point he realized that he needed to change if he wanted to survive, get out of prison, and stay out of prison, but he was struggling with how to make this happen. Bishop attended Gamblers Anonymous (GA) but described himself as a somewhat shy person and found it difficult to open up to other people in the group.

“You cannot effect change until you open up,” he said. “So when I found WordPress I was able to remain somewhat anonymous, and that made it easier to open up. I could write about my struggles and my feelings. I had some place safe to vent my fears and frustrations and anger. I had a safe space to process childhood trauma and self-destructive thought patterns.”

In January 2007, Bishop was released from prison and went into a work release program. These kinds of programs have employment requirements and have been shown to lower the recidivism rates among prisons.

“It was then that I discovered how difficult it is to overcome the stigma of being a felon,” he said. “No matter how much I wanted to do better and succeed, it proved to be more challenging than I expected. Within three months I was sent back to prison for a parole violation after losing my minimum wage job.”

Bishop, who describes himself as “a pretty intense mix,” of being bi-polar and living with ADHD on the Autism spectrum, found it difficult in prison to manage the mental and emotional health issues that led him to a gambling addiction. Mental health resources for prisoners can be scarce, but blogging helped him find a way through.

“I guess you could just call it personal talk therapy,” he said. “By writing about the experiences I had, being in prison, and how I was feeling, I was able to address my demons and work through the thought patterns that kept leading to destructive behaviors. I guess you could say it was more like a publicly accessible journal.”

Launching a WordPress Career Fresh Out of Prison

What Bishop learned in the work release program in 2007 about the challenges inmates face after prison became even more clear when he was finally released in 2010. Even though he had fully completed his sentence and was not on supervision, the challenges remained.

“Every GOOD job I applied for shot me down the second they learned I was an ex-con,” Bishop said. “From 2010 until 2015, I struggled to get a job that would pay the bills. I worked dead end fast food and temp jobs.”

In 2015, he and his wife were homeless with three small children living in a tent in Texas. It was this year that he was given the opportunity that launched his career in WordPress. He was offered a support role at InMotion Hosting.

“They took a chance on me and they paid for us to move to Virginia Beach,” Bishop said. “At first, we still lived in a tent and then a hotel. From there it was an upward trajectory and my career has continued to grow.”

Wolf Bishop speaking at WordCamp Atlanta in 2018

In the years following, Bishop has worked in various support roles and branched out into launching his own development and hosting companies. He is now on his fourth WordPress business, WP Octane, which follows two that failed and two that he successfully built and sold. WP Octane started in 2016 under the name WP Top Hat, and was geared towards being a 1-stop WordPress shop.

“The idea was to have a company that provided everything a business needed for its online presence,” Bishop said. “But trying to provide managed hosting, ongoing care, content management, marketing, SEO, and several other services proved to be more than I could handle on my on.”

In 2019, just before the pandemic hit, he decided to convert to just a managed WordPress host with ongoing care plans included, and changed the name to WP Octane. For the next two years his small startup struggled to thrive during the pandemic, although he did see some growth.

“Finally, in early 2022, WP Octane became profitable for the very first time,” Bishop said. “Since then we have continued to grow, albeit slowly.”

In late 2022, after investing more into infrastructure, WP Octane pivoted again to offer low cost shared WordPress hosting that serves a middle of the road between shared and managed.

“We limit tenancy of all servers to a fraction of what most shared hosts have,” Bishop said. “We introduced features that allow us to outperform most shared hosts and come pretty close to matching performance of a managed WordPress host. We have virtually eliminated many of the typical pitfalls of shared hosting like the dreaded noisy neighbor syndrome.”

WP Octane still offers fully managed plans with ongoing care included as they did previously, but the new shared platform has taken off better than Bishop expected and is now the company’s primary focus.

Empowering Inmates and Ex-Convicts for Success with WordPress Skills

Bishop is also now invested in giving back through a new effort to launch a prison program that will teach inmates the skills they need to use WordPress. The program is still in its early stages and has gotten preliminary approval from the Missouri Department of Corrections, which is local to where he now lives on 63 acres in the Ozarks. He is working on completing the curriculum, a requirement before it can be fully approved. The target for that phase is early August so it can go to a committee for approval at a September meeting.

“It is this struggle that led me to start this project,” he said. “I want to give inmates that truly want to turn their lives around a skill that can enable them to do just that. If they learn how to work with WordPress, whether it be design, development, SEO, or any other area, they can avoid some of the challenges I faced.”

Bishop said inmates equipped with WordPress skills will not be at the mercy of employers who are unwilling to give them a chance, because they have a skill they can use independently. If they go the route of custom development, most clients do not ask for a background check.

“When participants complete the program and eventually get out of prison, they will have a portfolio that they can show to potential clients and even employers,” Bishop said. “It is my hope that it will increase their chances of success.”

This is a first of its kind program that is still awaiting final approval. In the beginning he is aiming to launch it in the Missouri prison system but said he would love to take it nationwide some day.

Bishop is also working on a related project – a website that lists employment opportunities with WordPress companies that are willing to give ex-offenders a chance. The project is still in the early planning stages as he talks with employers to encourage them to join this movement. His experience with this community has led him to believe that WordPress will be a beacon of hope and opportunity for anyone who wants to make something on the web.

“WordPress helped me overcome addiction,” Bishop said. “It taught me the value of community and that if you are willing to put in the work, you do not have to rely on others to ‘let’ you succeed. WordPress lets you make success a choice.”