Read more about my background and journey.

Hello! My name is Brian Jackson. I’m currently working as the Chief Marketing Officer at Kinsta. You could say I have been an entrepreneur since a young age. Ask my parents, ask my friends; I was born to market and make money online. I have one of those brains that just never turns off, which can sometimes be a blessing and a curse.

I pretty much live on Twitter, so feel free to connect with me @brianleejackson

brian jackson

About Me

I have been an Entrepreneur and Internet Marketer ever since the 6th grade when I discovered eBay and started dropshipping CD/DVDs. I am an Inbound Marketer in the WordPress hosting niche by day and a blogger + affiliate marketer by night. I am a proud Seventh-day Adventist and owe everything I have to Jesus Christ.

Learn to say ‘no’ to the good so you can say ‘yes’ to the best. — John C. Maxwell

Recently Featured or Mentioned On

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Bio Timeline


It all started when I was in 6th grade. My parents bought an HP Compaq computer and we got free dial-up. I then stumbled across the internet and eBay. When I realized I could make money online, the whole world changed for me; and I have been an entrepreneur ever since.


By the time I was in 8th grade, I was reselling CDs and DVDs on eBay full time (or as full time as you can get while going to grade-school). I started dropshipping items from Deep Discount, which at that time had two separate sites, Deep Discount CD and Deep Discount DVD. I made $1,500 alone just on reselling The Cheetah Girls Original Soundtrack CD when it first came out. Deep Discount CD had it for $4.25 and I was selling it on eBay for over $15 a piece + charging for shipping. Also had great success reselling the Lonesome Dove DVD. During study hall my classmates would be in the library goofing off on MySpace while I was busy checking my eBay listings and researching new products to resell.

It was all about monitoring the new releases and creating a beautiful and effective ad on eBay. With the money I earned I went and bought my first laptop computer. I remember my feeling of pride knowing that I had bought my laptop with money I had made on the internet.


Now in 9th grade I started wondering what else I could do to make money online? I loved computers and started to wonder how they worked? So I ordered some parts and built my first computer. Upon completion of my first build, another light-bulb went off and within a week I had a business license (co-signed by my Dad since I was underage, Thanks Dad!) and a website up (highwirepcs.com) to sell custom built computers. I sold them on my website and also on eBay; quickly achieving PowerSeller status. Back in those days, custom built computers on eBay were still hard to find and the competition was low. I would sell a computer on eBay, order the parts from Newegg, and build their computer to order. I would then pack it up and ship it off to them.

I sold computers to countries all over the world. I remember my Mom helping me by picking up custom boxes, 10-15 at a time from a local box distributor, taking the scale out to the kitchen, and packing it up for shipment (Thanks Mom!). This is what I did for most of the 9th and 10th grade. My feedback profile on eBay proves it, 1,597 and still going strong at 100% positive feedback. Don’t get me wrong, this wasn’t an easy job. I had many many evenings where things would break, or a piece of hardware would be bad. And all of this was done after I got home from school. While other kids were playing video games, I was building computers.


Fast forward to the 11th grade and I was now wanting a less stressful and easier way to make money online. I took a job as the network administrator’s assistant at my high school and I started looking into web hosting. And by the time I graduated high school I had a dedicated server in a data-center and was hosting over 700 domains, still under the “HighWire PCs” branding.


Freshman year of college I took a job at the HelpDesk at Walla Walla College (now Walla Walla University). That was probably one of the best decisions I have ever made. Who knew I would be working there for 6 more years and gain work experience that was literally priceless. About halfway through my freshman year I realized I couldn’t keep up with the support and maintenance for all my web hosting clients and so I sold my company, HighWire PCs, along with all the clients.


Freelance web design and computer repair house calls were my nightly routine, that and homework. Alongside my job at the HelpDesk. You could say I was a workaholic… It’s OK, my friends all did.


I was promoted to Student IT Manager at the HelpDesk at Walla Walla University. During this year I was blogging on my website, brianleejackson.com. Some of my popular blog posts were:


Took a full time job as the Peoplesoft Security Administrator at Walla Walla University.


Started the IT blog theitbros.com, along with my brother. We decided to start the site because we got tired of searching for technical fixes and information and it taking more than 5 to 10 minutes to find what we were needing; or not finding a solution at all. So we started a site where we could post tutorials on how to fix technical issues.


Packed up everything I owned and without a job lined up I moved to sunny Scottsdale, Arizona. I got sick of the rain in Washington state. Fortunately, by the time I arrived in Scottsdale I had a few job interviews and took a job at the HelpDesk at Partners Rx.


Sold theitbros.com IT blog for $7,000, boosting my current Flippa sales over the $10,000 mark. Took a job at Pain Doctor as their AdWords and SEO Specialist.

Late September – 2013

Received the 2013 Microsoft MVP Award in Windows Expert-IT Pro category and launched OKay Marketing.

June – 2014

Boosted my Flippa sales over $12,500.

September 1st 2014

brianjackson.io hits steady 10,000 visitors per month with no paid advertising

September 30th 2014

brianjackson.io reaches 12,500 visitors a month without ever building a single backlink

January 1st, 2015

Launched a blog, pennybros.com, with my brother about getting debt-free, paying off our student loans, and investing for early retirement.

May 15th, 2015

brianjackson.io reaches over 35,000 organic visitors per month! Launched nogluten.io where I blog about eating gluten-free. I was diagnosed with Ulcerative Colitis in 2014 and am now medication free thanks to my diet and tricks I have learned.

September 15th, 2015

Acquired woorkup.com where I share marketing strategies pertaining to SEO, SMM, WordPress, and web performance; along with in-depth SaaS reviews.

June, 2016

My brother and I launch our first premium WordPress plugin, WP Coupons. It is the #1 WordPress coupon plugin for affiliate marketers.

wp couponsJune, 2017

My brother and I launch our second premium WordPress plugin, perfmatters, which can help speed up your site.