20 Years Of Redpoint Creative
It’s hard to believe that 2026 marks 20 years in business – from faint glimmers in late 2025 to opening up in January 2006–so much has happened, so many clients and friends, offices and basements, typos and triumphs. I am really proud of all the work, but more, the relationships that have carried my business this far. Here are some highlights from the past 20.
“We’re not makin’ art here” – A client I no longer work for
Where It All Began
I started stacking paper and doing paper paste up in the late nineties. I learned a lot about production then, something I carry even today. But I eventually found my way to Focus Design Group and Dwayne Holland, a great mentor and friend. He took a flier on me and things have never been the same.
We shared a single computer. We made things by hand. No email at the start. One of my first tasks was organizing the ’zip’ and ’jazz’ disk archives. For days. Websites didn’t exist. We actively counseled people that ‘they didn’t need a website yet’.
Some highlights from this season of life: Getting to assist on The City Of Red Deer’s brand (2003) and working with Superior Emergency doing “fire truck stuff”.
Notable people: Christine, Carson, Karin, Tony. Also, world class achievements like typo’ing “public” to “pubic”, second only to misspelling “genius” as “genuis.” Way to go, genuis.
“Bushy end of the pineapple” – Carson Pierce
Redpoint’s Genesis
The cover of the 2006 RDC Viewbook. The project that started it all.
I started redpoint officially in 2006 and have never really looked back. Red Deer College’s 2006 prospective student Viewbook was my first big project, working with Dwight Arthur as photographer, and Lois and Melinda at the College. Fun Fact – I sent the 2007 edition to print 1 day after my daughter was born later in 2006.
“It’s not a photoshoot if Brian is not bleeding.” – Dwight Arthur
A few of the first brands I did, including the first website – V-Teck Fencing.
The First Redpointer 2007
I hired Sonya in 2007 and we worked together for many years. When I think of the projects we did, the working at the house, with a baby in tow – it was actually insane. I’ll always honour Sonya for sticking with us in this season.
Almost no one I’ve worked with could grind out projects like Sonya, and I will always remember her when I hear Kings of Leon and Lady Gaga.
“I’m really sorry these babies are crying so much.” – Brian Olstad
The Kaylor Building 2007-2012
Realising how we needed to grow and build structure, I took an office on 48th street with Jonathan from Kalischema and we had A LOT of space, and north windows (my #1 need). We also bought about 1,000 kg of flat packed desks from the scratch and dent area in Ikea. Still love this space – and hate the blue walls – and miss my red couch.
The Second Redpointer
In 2008, Kayla walked in and asked to do an internship in the office. I said yes and we never looked back. Kayla brought a dynamic to the creative that is very rare, and hard to replace. Kayla is also a very good friend. One thing I’ve always done is rooted for the people around me.
My step dad always said “you can’t stop people from moving”. As staff have moved on, I’ve always watched them quietly from the sidelines, proud of the little bit I could contribute to their careers.
“Why can’t we hand-illustrate that and print it on letterpress?” – Kayla English
Office Mom
My friend Aaron recommended that Illa help us out with the office, as a last hurrah before she retired. One cannot express the impact someone with a lifetime of experience brings to a team.
Illa helped us plan, account, and anticipate. All that while counseling us as people and making sure we were taken care of. I will be grateful to Illa forever.
“It will be ok. You should just do that.” – Illa Jackman
Redpointaversary 2010
In 2010 we had our 5 year anniversary – a celebration at the Kaylor Building. We built gingerbread houses, ate gingerbread houses and had a large photobooth. I always love thinking back on this party and seeing who showed up for us.
The Scott Block 2012-2015
We decided to upgrade to the Scott Block in 2012, and by upgrade, I mean, renovate an office and move in. The office probably had not been renovated since Don Draper’s era, and we did a lot of work emulating “Mad Men”. It was smaller space, but more private and allowed for all of us to have a personal space. This era marks a bit of a creative heyday for us. We took a lot of risks, doing work that required a lot of manual labour and hand illustration in an era that was not common. If it wasn’t hand drawn or illustrated, it was never good enough for Kalya. At the very least, it should be hand printed on a letterpress!
I was often standing in the office waving my hands explaining something and Kayla coined the phrase: “You have a multi-frame brain.” This is because I was usually tracking three thoughts at once and building them all in the air in front of me.
I worked with Tony and helped develop a custom CMS we called the Coffee Maker and we published a lot of Coffee’s. WordPress was still blog focused, so your average website was limited to Joomla or Drupal. Much to complex for most clients.
The amount of time spent at Kevin’s “Cool Beans” coffee bus cannot be understated – a place I met so many people – including the indomitable Joe Whitbread, a relationship that grows even today.
“Kill it and Bill it” – Brian Olstad via Dwayne Holland
The Dark Times 2016-2020
Life has a way of moving on as people also do, and by 2015 I was mostly solo-preneuring again. A blessing of this time was meeting Anna and continuing to design interpretive signage, starting off with a bang, I designed the interpretive exhibit at the Legacy Centre in Slave Lake. I call this section the dark times, but there was so much good – including reconnecting with my mentor, Dwayne.
I also got to design the character for the mascots of TWO Canada Winter Games; 2015 and 2019. I am quite sure if I could just do mascots all day I would be very happy.
I formed a new company (Symbra) and kept Redpoint as a production company for a while, but the pandemic had other plans.
“Brand everything. Then it BECOMES a thing” – Brian Olstad
Renewal 2020 – Today
The pandemic offered a real opportunity to shake things up and brought new relationships to the fore. Still at home, I started illustrating vacations and helped found the David Thompson Climbing Association – and achieved one of my long time dreams – designing a guidebook (I’ve done 3 editions so far). I also was able to learn quite a lot more about brand and web technology.
These past 6 years have been exciting, and I have so many new clients and friends. I have new clients in Red Deer, Calgary, Toronto, and San Diego. I was happy over the pandemic to reunite with a friend in Calgary and did brand counselling and web and brand collateral (just not the logo) for his company – Fresh Start Mediation – and watched the firm grow.
I’ve built brands and brand standards for sports organizations across the province of Alberta. I’ve watched my friend Tim’s rock guiding company turn into one of the premier climbing guiding outfits in the province with clients coming from across North America to our little mountains out west, in part due to my web design and search engine planning and optimization.
What’s Next
I’ve been around. My hair is a little greyer. AI breathes down the neck of all of us who don’t learn to leverage it. No one buys nice print anymore. Social is mostly pay-to-play.
And yet, my vision for the creative business is clearer than ever.
Over twenty years, I’ve learned that design is rarely about making things look “creative.” It’s about helping people communicate who they are before they ever walk into the room. The best projects were never really about logos or websites or guidebooks or mascots. They were about helping good people move something meaningful forward.
So what’s next? Probably more of the same, honestly. More conversations. More sketchbooks. More overthinking typefaces. More websites. More coffee. More helping people untangle ideas and turn them into something lasting.
I’ve always believed the best creative work comes from relationships built slowly over time. Twenty years in, that part hasn’t changed at all.
And for everyone who trusted me somewhere along the way — thank you. Truly.
