I’m Dennis Dimka, Founder & CEO Of Uptime Legal Systems, And This Is How I Work



Thanks to Minnesota Tech Startup Supporter Fueled Collective for underwriting our entrepreneur-focused How I Work series.

Uptime Legal Systems helps law firms manage and grow their practice with cloud, legal technology, and marketing services. Named an Inc. 5000 Fastest Growing Private Company in 2014, 2015, 2016, 2017 and 2018 – the company is both bootstrapped and growing.

At the helm is CEO Dennis Dimka, who started the company in 2005 and continues to lead a team of ~25 today from Eden Prairie headquarters.

Because he is succeeding as a software entrepreneur, we’re here to learn about work habits and the the way he operates Uptime Legal Systems on a typical day, inside and outside the office:

What one word best describes how you work?


What is your current device/hardware/office setup?

My rig is a Surface Book (which goes with me everywhere), which I dock in my office to three monitors. More monitors = more productivity. (I’m pretty sure that’s how it works.) Also on my desk is my phone, Keurig, tack-board and various organizers. If only I could figure out how to take those with me when I travel.

What apps/software/tools can’t you live without?

Outlook, of course. Nothing beats it when it comes to robust email tools (rules, flags, tags, QuickActions, customization, email templates, etc.)

I also find myself more and more dependent on OneNote. Over time it’s become my personal database for… everything. Meeting notes. Strategic planning. Sketching out projects or ideas. Writing content. Organizing information. (I’m conducting this interview in OneNote right now.)

I’ve also become partial to Wrike for project planning. It’s a great system for managing everything from large-scale projects, to keeping lists of all the things you need to keep track of, to your own daily to-do list.

What your sleep schedule like in terms of hours/wake-up and the morning routine?

It’s up at 6:00 AM sharp to get my daughter to her school bus. After that it’s to the office, where I arrive around 7:45 AM most mornings. That first hour in the office in the morning is the best time to plan my day or make progress on projects without interruption.

Is there a method to how you schedule your days?

Yes. Over the years I’ve developed my own personal productivity/work planning system. Its one part Getting Things Done (GTD), one part Most Important Tasks (MITs), one part Laywerist Productivity system (no I’m not a lawyer, but theirs is a great system) and one part my own home-brew planner. It’s what I use to schedule my week, prioritize most important projects and tasks, keep on top of what it’s my court, what I’m waiting on from someone else, and ultimately keep my arms around both the big-picture and the nuts-and-bolts.

Today, I couldn’t function without my blue folder. Its wonderfully low-tech, and serves as the hub to all of my digital tools.

How much time do you spend in vs. out of the office?

90% (or more) in the office. The remaining 10% I’ll spend meeting with other companies, at their offices or (if I can’t avoid it) at trade shows. I’d love to spend more face-to-face time with our amazing clients, but being a national company they’re all over the US.

Where is the office?

HQ is in Eden Prairie, 6th floor of a suburban high-rise. I also spend time working out of our Manhattan office, 3-4 times per year.

What’s your best time-saving shortcut/life hack?

Get yourself an online scheduler service like ScheduleOnce or Calendly, where people can view your calendar (availability) and schedule calls or meetings with you in real-time. This cuts down on the umpteen back-and forth emails when trying to schedule a meeting. It saves me hours per week.

And while you’re in time-saving mode, setup a password management system like LastPass. Seriously, you’ll have hours not only remembering/typing passwords, but going through the usual Forgot Your Password process. You’re welcome.

What is that one thing you have to do, no matter what, every day?

Kiss my wife and kids every day. Every morning: Review my (aforementioned) work planning system to understand what I need to do today. (I know you asked for only one, but I couldn’t pick just one.)

Also, begrudgingly, stop to eat at least once per day.

What is your preferred form of communication and why?

Maybe Slack. Its quick, efficient, keeps a conversation history, and keeps my email inbox free of clutter. I also like the “old-fashioned Slack,” that is: walking across the office and having a face to face dialogue with someone.

On average, how many hours a day do you spend in meetings?

2 to 3, depending on what counts as a meeting (internal team meetings, working sessions and the like). More if you count sales meetings and impromptu team check-ins.

When, where and what do you typically eat for lunch?

I’m all about efficiency, so I almost always grab something to eat from the café/restaurant in our office building. I’m in and out in 10 minutes or less.

How many hours a week do you work on average and do you work in the evenings and/or weekends?

Probably around 50. It used to be more (the classic 70+ hour weeks of starting a company), but today I have something that I can at least pass off as work-life balance.

What is the best advice you ever received, accepted, and applied?

From a mentor: Specialize. Go big, go vertical or go home.

In earlier versions of my company, we were a local technology generalist. Today we’re a highly-focused, national specialist (we provide cloud and technology services to law firms across North America.) Specializing and honing in on a crisply-defined market snaps everything into focus. Your strategic plan. Your marketing. Your sales pitch (and materials). Your service delivery processes. Everything.

Fill in the blank: I’d love to see Josh Kleve of DKS Systems from Minnesota’s tech industry answer these same questions.