Jim Martin is the founder of Captivation Agency, a 9-person team based in Sarasota, Florida, founded in 2004. With roots in interactive software development (remember Flash?), Jim has seen the industry evolve in incredible ways — and he’s kept his agency thriving through every twist and turn.
What’s clear when you talk to Jim is how much his family has shaped his journey. Inspired by the wisdom of his grandfather and father, motivated by his mother’s courageous battle with cancer, and driven by a deep sense of purpose, Jim started his agency not just as a business, but as a way to build something meaningful. Through challenges like navigating the 2008 recession and the 2020 pandemic, he’s kept that focus — and built a team and client relationships that reflect it.
Jim’s story is packed with insights about leadership, teamwork, and embracing change, but what stands out the most is his thoughtful approach to running a business. Whether it’s delegating tasks, documenting processes, or staying true to his core values, Jim’s advice is as practical as it is inspiring.
What got you into WordPress and how long have you been using it?
We have been involved in the WordPress ecosystem since 2008.
Our agency’s roots started in interactive software development (rich media) – predominantly building immersive websites using Macromedia/Adobe Flash, which featured optimized video content. Back then, we were among those pioneering some of the first Flash sites that were search engine optimized.
Following the announcement of Flash content being sunsetted in favor of other technologies, we began searching for our next development ecosystem.
We chose WP for the strong community, widespread (and growing) adoption and it’s openness/flexibility to enhance our creativity into the future.
What motivated you to start your own business, and what keeps you going when things get tough?
My grandfather was a huge role model to me from a very young age.
A self-made commercial fisherman, he imparted 70+ years of wisdom to me until he passed when I was 10.
His voice still rings in my head with things like: “If you’re successful, people will know, you don’t need to tell them” and “Your word is only as good as your actions…”
Armed with his strong foundation, I also was strongly influenced by my father – a successful independent financial consultant, he used to say “When you work for yourself, you wake up every day unemployed… and it’s up to you to make things happen and figure out where your money is coming from…”
In October 2003, my mom was diagnosed with breast cancer, and given 3 months to live. Not having health insurance at the time, my mother was not planning to receive treatment. I had just started college at the time, and determined to help, I set out to get all of my school paid for – allowing all of the funds that had been set aside (by my grandfather) for me to go to school, to then be used for my mother’s treatment.
I founded my company in 2004, from a love of creating and building things, but also, to share the journey with my mom – to give her something positive to follow and encourage us both.
In time, 3 months turned to 5 more years for my mom. She saw me graduate from college in 2005, and watched the business grow, become something that would support me and others, before she passed in 2008.
When things get tough, I remember what she told me during one of the harder days – expressing my desire for her to be proud of what I was doing, she said: “all you have to do it breathe and I’d be proud of you…” Those words continue to fill me with both the drive to push through the more challenging days, and the grace to not be so hard on myself when things aren’t going as expected.
What’s a hard lesson you learned running your business that’s changed the way you operate?
Your mission, vision, and values are things that can sound somewhat trivial when you are the “Chief Everything Officer”, but matter THE MOST as you begin your journey.
They are not only the basis on which you attract and align team members and contractors as you grow, but even before that, should be the foundation of how key decisions are being made.
Not addressing these early on will create challenges (big and small) at some point in the future (I’m speaking from experience here).
The other would be creating “scorecards” for every defined position within your company. Even if you are currently the one assigned to all of the cards, someday, you won’t be.
The more you can define what the roles and responsibilities of each position in your company looks like (and how it ties back to your core values/mission/vision), the easier it will be to quickly post applications for freelance or full-time help and offload/onboard people to take those areas of the business over.
**It’s also important to re-assess those scorecards regularly to ensure team members aren’t taking on too much or are focussed on items not yet listed in their scorecard (or, they are taking on things not included in their score card at all to you need to be aware of).
We’ve encountered situations where a team member received a new title, but we never went back to their scorecard to determine what of their previous day to day might need to be handled by someone else… This created obvious frustration for all parties involved the further down the road we went without addressing it. Lesson learned. Shoutout to Coach Pete for bringing these practices to light for me!

What’s the best piece of advice you’ve ever gotten and how has it affected your business?
Document, while doing. As an army of one, you do everything, but that isn’t going to be the plan forever (even if you plan to grow with freelancers, rather than full-time staff)
Record looms for every major thing you do throughout the day. Explain the “why” behind the thing you are doing, as well as the key steps and things to be aware of. Then, when you assign the tasks or roles from that video out, and a process changes, it is that person’s responsibility to update the loom.
Also, as you move through your week, be aware of the things that light you up, as well as the things that frustrate or annoy you. Capture them in a journal or somewhere you can easily refer to. These lists will reveal your first potential hire(s).
Today, I am very aware of the things I am procrastinating. That is my best indicator of something that needs to be delegated to someone who eats/sleeps/and breathes that thing I continue to push off. (and oh, btw, they will likely do that thing better than you as a result)
Lastly, set time at least once a year, if not more often, to go through your profit & loss statements for the business and identify opportunities to cut recurring expenses you may no longer be using.
It shouldn’t take too long, but you could save yourself 100’s if not 1000’s of dollars as a result.
Thank you to Kyle and my whole TABLE group fam for imparting and reinforcing these practices on me each and every week!
As an entrepreneur, what’s your proudest accomplishment?
I am proud of our history, 20+ years in business, helping to provide opportunities for others (team members and clients alike). Enduring the economic challenges of 2008 and a global pandemic in 2020.
In 2019, I was also recognized as one of 10 national recipients of Maytag’s Dependable Leader Award, in partnership with the Boys & Girls Clubs of America – something I could never have achieved without the amazing team and clients we have.
What’s a book every agency owner should read?
Who, Not How (Dan Sullivan), Buy Back Your Time (Dan Martell), & Profit First (Mike Michalowicz)
What’s your favorite podcast to listen to?
How I Built This, & My First Million
What’s a WordPress plugin everyone should know about?
What’s your favorite non-WordPress tool or software?
I have been geeking out on Airtable since first adopting it in 2023! Also love the Blitzit app for task management.
What’s your favorite tool, accessory, or gadget on your desk?
A simple journal to hold up to 4 Field Notes notebooks and a nice pen (because having a nice pen makes you find more reasons to write more things down)