Today we’d like to introduce you to Chris Westmeyer.
Hi Chris, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
My story isn’t a straight line; it’s a collection of detours. I never graduated high school and spent five and a half years grinding my way through college, only to come out the other side feeling lost.
I’ve been an entrepreneur since I was 12, starting with a software development and distribution company. I always had big dreams, but in every position I took after college, I was driven by a specific kind of fear. Growing up, things weren’t always easy. We occasionally struggled for the basics, and while my mother did her best to shield my siblings and me from it, I was smart enough to see the reality. That stayed with me. I felt average or below average as a child, so as an adult, I felt I had to be the best. I had to grow every company I touched because I didn’t want anyone to see me as anything less than great. On the surface, I was moving along as planned, but internally, I wasn’t happy. I was just running away from being average.
My career in digital marketing actually started before it was even on my resume. I used to bake digital responsibilities into jobs that didn’t ask for them, then spend hours every night testing and figuring out how the tech worked on my own. I was obsessed with the power of it—the ability to actually impact people at scale.
That drive moved me through engineering firms, national associations, creative agencies, and financial firms, eventually landing me at Outrider. At the time, it was one of the largest search marketing agencies in the country. It was my dream job. I was leading teams for massive brands, but the biggest shift was still to come. When the global conglomerate WPP acquired Outrider, my world changed overnight. Suddenly, I was participating on Google and Microsoft customer advisory boards and helping run some of the biggest brands on the planet.
I was on top of the world, but it wasn’t meant to last. WPP eventually decided they no longer wanted a footprint in St. Louis. They began slowly dismantling the office, first asking for volunteers to relocate, then eventually shutting the doors entirely.
Leadership approached me with an offer to run a division in Manhattan. But back then, remote work wasn’t an option, and I wasn’t willing to uproot my family for a New York office. I was told it was time to move on.
I spent the following months meeting with almost every agency and marketing firm in and around St. Louis. I wanted to find a partner to help grow their digital offerings. One by one, they all turned me down.
Ultimately, I realized that if the place I wanted to work didn’t exist in St. Louis, I’d have to build it myself.
That company, Digital Strike – Targeted Marketing, just celebrated its 15th anniversary in 2025. What started as a necessity born out of rejection is now on a mission to be the best digital marketing agency in the nation. Looking back, all those detours weren’t distractions, they were the foundation for everything that was to come.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Creating Digital Strike – Targeted Marekting wasn’t a matter of following a manual or guide, it was a matter of surviving a series of roadblocks that, at the time, felt like each might break me.
Navigating the Invisible: For years, I struggled without understanding that I had ADHD. Compounding that, my parents mistook my high-functioning anxiety for depression, and we spent years trying to treat the wrong thing.
A Fragile Foundation: I didn’t always have a stable home environment, which made focusing on a “traditional” future very difficult.
The Academic Hurdle: I never graduated from high school. Even after getting my GED, the path to college was a constant uphill battle of proving I belonged there.
The “Wrong” Credentials: I don’t have a marketing degree. I ended up with a degree in Psychology, which, ironically, became my secret weapon in understanding consumer behavior, even if it made getting my foot in the door harder to start.
Scraping for Resources: I didn’t have the financial means to own the tech I needed to learn. My “office” was wherever I could find a screen, staying late after school, spending weekends at the library, or hanging out at the local mall computer store just to get any time on a keyboard.
The Power of ‘No’: When it came time to buy the first Digital Strike office building, I was turned down by almost 20 banks. It took 20 “no’s” to find the one person who believed in the vision enough to say, yes.
Battling Bureaucracy: Even once we had the building, the fight wasn’t over. I had to convince the city of Webster Groves that I could revitalize an entire block of office buildings. They didn’t see the vision at first, which made the process both difficult and incredibly expensive.
As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
Digital Strike – Targeted Marketing is known as the “go-to” digital marketing agency for search-focused solutions nationwide. We’ve built a team and a product offering that I truly believe is second to none, largely because we refuse to settle for “average” results. Our entire approach is driven by a framework we call M.O.R.E.
M. — MEANINGFUL STRATEGY:
We don’t just make noise; we design digital strategies that are rooted in deep understanding, aligned with real business goals, and built to drive impact. Every move has a purpose.
O. — OPTIMIZED FOR WHAT’S NEXT:
We build for today, optimize for the future. Grounded in research and driven by data, we uncover patterns, anticipate change, and position you ahead, so you’re always ready for what’s next.
R. — RESULTS THAT MATTER:
We measure everything, but we focus on what actually moves the needle. No vanity metrics. Just growth that’s visible, valuable, and aligned with your business success.
E. — ENGAGED PARTNERS:
We’re in it with you. You won’t just get reports; you’ll get insights, strategy sessions, and a team that genuinely cares. We guide and educate so you understand the data and what it means for your goals.
What I am most proud of is our tenacity. We don’t hide behind “fluff” or complex jargon, we provide the clarity and results that businesses actually need to grow. What sets us apart is that we operate as a true extension of our clients’ teams—their wins are our wins.
BOLD STRATEGY.
STRIKING RESULTS.
How do you think about luck?
People often ask how I built Digital Strike into the agency it is today. My honest answer? I got lucky.
But not in the way you think. I do not think of luck as lightning striking; it’s a system. I view luck through four distinct lenses, and I believe you can actually “manufacture” most of them.
1. Blind Luck (The “Lottery”)
This is pure chance, the circumstances of where you were born or finding $20 on the street. You can’t control it, and you certainly can’t plan for it.
The Strategy: Accept it when it happens, but never rely on it.
2. Active Luck (The “Hustle”)
This is the result of constant motion. If you increase your “surface area” for opportunity, “coincidences” happen more often.
The Strategy: Send the email. Go to the event. Action creates collision points with luck.
3. Prepared Luck (The “Awareness”)
This is spotting opportunities that others miss. It’s why two people can read the same report, but only one sees the billion-dollar idea. It’s about having the background knowledge to recognize a lucky break when it’s staring you in the face.
The Strategy: Train your pattern recognition. Stay curious and respect your intuition.
4. Magnetic Luck (The “Character”)
This is the “Holy Grail” of business. This is when luck finds you because of your reputation. Opportunities seek you out because you have proven yourself to be reliable, skilled, or unique.
The Digital Strike strategy has been to build a reputation for excellence. Eventually, your character becomes a luck magnet.
Waiting for blind luck is gambling. But generating motion, staying alert, and building a reputation isn’t just “being lucky”, it’s being successful on purpose.
Contact Info:
- Website: https://www.digitalstrike.com/
- Instagram: https://www.instagram.com/digitalstriketm/
- Facebook: https://www.facebook.com/DigitalStrikeTargetedMarketing
- LinkedIn: https://www.linkedin.com/company/digital-strike/
- Twitter: https://x.com/DigitalStrikeTM/
- Youtube: https://www.youtube.com/@DigitalStrikeTM
- Other: https://www.trustpilot.com/review/digitalstrike.com
