01 / About
Damian Raszewski
Principal Technology Advisor · Lincoln Square Technology
Punctilious Technology Advisor. I tackle complex problems so you don’t have to.
02 / My Approach
Technology can be complicated. It doesn’t have to be.
My consulting philosophy is rooted in understanding the particular challenges you are facing and providing solutions that work well — for you specifically.
What everyone needs is different, and what one person finds easy may be difficult to another. I don’t believe one size fits all. My solutions are unique to each client, and I measure success by whether things actually work for the person using them — not by technical benchmarks that don’t translate to real life.
The guiding principle behind everything I do: Keeping IT Simple.
03 / Complex Problems
Simple solutions to complex problems.
Sometimes technology gets messy. Wires behind walls, software that won’t cooperate, systems that talk to each other in ways nobody planned. That’s what I’m here for.
I work through the complicated parts so you can focus on what actually matters to you — without needing to understand every wire behind the wall.
Most technology consultants will fix what’s broken. Damian Raszewski would rather make sure it doesn’t break in the first place — and if it does, help you understand why, and what to do differently next time.
With 30 years of experience across an almost absurdly wide range of environments, Damian has served as the de facto IT director for organizations that couldn’t afford a full-time one, and as a trusted advisor to those that already had one. He’s rebuilt the IT infrastructure of a Chicagoland bank chain branch by branch, helped small publishers keep their Mac-first workflows humming, oversaw the networks behind enormous hotel conferences, and supported a vintage art gallery, a lighting design firm crafting custom fixtures and chandeliers, and nonprofits ranging from the American Heart Association to children’s services organizations. He was deploying high-density WiFi and experimenting with tablet-based ordering systems at the Hyatt Regency long before QR code menus became unavoidable.
Working alongside designers, media teams, and creative professionals eventually made a Mac convert out of him too. Today, Lincoln Square Technology is built around Apple’s ecosystem, because it’s what he recommends, what he uses, and what consistently delivers the reliable, elegant experience his clients expect.
Those clients include small businesses of every stripe along with households that just want their technology to work without a second thought. Whether you’re a small business owner who needs a real strategic partner rather than a break-fix vendor, a family that’s done fighting with the router, or a parent trying to make sure an aging relative is safe and set up properly — Damian brings the same thing to every engagement: the experience to know what matters, the patience to explain it clearly, and the judgment to tell you what you actually need instead of what sounds impressive.
He’s based in Chicago’s Lincoln Square neighborhood, and he is genuinely excited about AI in a way that should probably concern his friends.
04 / Work Together