Today we’d like to introduce you to Jason Finn.
Jason, can you briefly walk us through your story – how you started and how you got to where you are today.
I spent the first ten years of my career as a management consultant and a technologist. I worked for PwC and IBM, serving clients like AOL, Eli Lilly and Company, Allstate Insurance, and Ford Motor Credit. I became a senior consultant in the business analytics and data warehousing practices, and in time was managing large scale projects for some of our biggest clients.
After years of airplane travel, or long commutes in the car, I decided I needed to get closer to home. “What career requires me to physically be home, in Chicago?” I thought. And I decided to get my real estate license.
In August 2006, just ahead of the market crash, I got my real estate license. I immediately hung my license at Baird & Warner in Lincoln Park, and learned the challenges of being a real estate agent. Where I billed by my time as a consultant, and no one was ever late to a meeting, or challenged my advice, I learned that real estate agents are not always held in the highest esteem. I learned that I needed to continually demonstrate my competence as an agent, and in a difficult time for the industry, I built my business.
A few years later I started working with a real estate coach, who in addition to making me a better real estate agent, helped me see what being a small business owner was all about.
Along the way, friends, colleagues, and past clients approached me for help of a more technical variety. I was helping them get their websites, their new businesses, and their side hustles off the ground – technically, operationally, and through my marketing knowledge. Before long, and specifically in April 2011, Geek Chicago was born.
I need stimuli from multiple sources, so in addition to growing and operating Geek Chicago, and retaining a successful real estate practice, and raising two amazing children, I also host Windy City Poker Championship, which highlights poker tournaments benefitting local charities. It airs on NBC Sports Chicago (and is syndicated nationally.)
Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
I’ve been incredibly fortunate to have the support of friends, great acquaintances I’ve met through networking, and my very best clients. The road has been a slow climb at times, but I’ve managed to avoid major setbacks. I decided to build the business organically and methodically. I feared growing more quickly than I was able to support more so than fearing I wasn’t bringing in enough revenue. I never sought financing or leverage outside money, so the early days were lean and mean, and we continue to be shrewd with business expenses and the rate of growth even to this day.
My biggest challenge today is time management. I like to take care of my clients, and they like to know that I’m taking care of them. Finding processes and systems to maximize efficiency, and finding talented team members to help build, grow, and thrive is critical for success each and every day.
Please tell us about Geek Chicago.
Geek Chicago is a digital marketing company that helps small- and medium-sized businesses, as well as the political world, grow and maintain their audiences. We help lawyers, architects, insurance companies, financial advisors, and home services companies (amongst others) reach a broader audience, and gain and retain new customers. We help elected officials and candidates for office spread their message and communicate effectively with their constituents.
We do website design and development, and we do reputation management. What really sets us apart, however, is our approach to content marketing, which begets search engine optimization (SEO), social media management, and digital newsletters. For many of our clients we write 100+ high quality, brand enriching blog posts or articles every year. This content resides on our clients’ websites, drives traffic and leads to the business, and becomes sharing fodder for web visitors, social media posts, and our clients’ digital newsletters. This strategy has sent our clients all the way to the very top of Google search results for many of their most important keywords.
We’ve written articles across dozens of industries, and we do so in our clients’ voices from their unique perspectives. This is no easy feat – it requires intent listening, research, and some very talented copywriters.
If you had to go back in time and start over, would you have done anything differently?
If I had to start over from scratch, I’m not sure I would have done much differently.
One piece of advice I’ve received, and now believe in, is to make sure you seek out talented support staff and team members actively. Once you’re so busy that you know you need assistance for sure, it may be too late. Being buried with work AND trying to recruit, hire, and train simultaneously is very stressful. I’ve found myself in that position more than once.
If I could send 2005-Me a message it would be to hire early, not late.
Contact Info:
- Address: 3717 N Ravenswood Ave.
Suite 219e
Chicago, IL 60613 - Website: www.geekchicago.com
- Phone: 773-683-2441
- Email: info@geekchicago.com
- Instagram: www.instagram.com/geekchicago/
- Facebook: www.facebook.com/geekchicago/
- Twitter: www.twitter.com/geekchicago/

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