Dennis Dimka – Founder & CEO, Uptime Legal Systems

Dennis Dimka is the founder and CEO of Uptime Legal Systems, North America’s leading provider of technology, cloud, and marketing services to law firms.

Dennis started Uptime as a general-practice IT service provider in 2005. Over Uptime’s first decade, Dennis grew Uptime from a geographic-generalist to a national specialist, honing Uptime Legal’s focus to nationwide cloud services to law firms. Uptime Legal has also been an Inc. 5000 fastest-growing private company for three consecutive years.

Dennis is the author of Law Office in the Cloud: How and Why to Move your Law Firm to the Cloud, The Law Firm Cybersecurity Survival Guide, and was also an Ernst & Young Entrepreneur of the Year 2016 finalist.

Tell me about your early career.
I began my career in IT, first in technical support, then as a network administrator. Working with outside IT consultants, I thought “I can do that,” and started Uptime as a pure play IT consultancy.

How was the first year in business?
Uptime’s very first year was strong. My initial goals were conservative: to make more money than I did at the job I had left. In year one, I accomplished this and then some, and Uptime continued to grow rapidly, and profitably.

How fast did the company grow during the first few years?
Uptime (then Uptime Systems) evolved pretty quickly from a pure consulting firm to a IT managed service provider (MSP). To be proactively innovative, in 2008, I refocused the company to build and deliver cloud services.

By 2012, Uptime Systems was roughly half IT provider, half cloud provider, and all generalist – no specialization or vertical focus. We were growing year-over-year, and profitable along the way. But we were still a relatively-unknown, small company. We began to realize that cloud computing, as a service-provider business model, was the future. It broke down the walls that limited our market to where our engineers could travel.

But in this new, larger market, our new cloud computing rivals were beginning to make the same realization (and they were bigger and better-funded than us). We knew we had to remain one step ahead of them, or be lost in obscurity.

It was time for Uptime to truly stand on its own two feet, and throw down the gauntlet. And to do that, I knew we needed to specialize. Specifically, it was to go vertical. Our chosen vertical was the legal industry. Over the years, we had developed the expertise and the contacts within the legal technology sector enough to deliver our best-in-class cloud computing services to law firms.

So, we made the leap and went all-in on cloud computing in the legal market. Fast forward to today, and Uptime Legal has grown to become the #1 provider of cloud services to law firms, and has expanded its portfolio of offerings into legal document management and legal marketing.

What was your marketing strategy?
In its early stages, Uptime grew namely from Internet marketing. The Internet is a great equalizer. It can give small businesses the image of a large company. Internet marketing gives small players a seat at the “big boy table.” Internet marketing helped launch Uptime in its early phases, and remains a major part of our marketing engine today.

How do you define success?
In a phrase, I define success as, and measure success in, growth and profit. I want my company to grow and to profit. I want our clients to grow and to profit with us. I also want our employees to grow as professionals and profit along the way, in order to get something back from their time here at Uptime.

To summarize my own personal definition, success is growing as an entrepreneur, profiting from your hard work, and helping others do the same along the way.

What is the key to success?
I think there are many keys to success, but in my own personal experience, there are a three primary ones:

1. Strategic planning – Whatever the stage of your company or endeavor is, have a plan. Your plan should include big picture and long-term goals, medium-term goals, down to monthly and even weekly goals. Your daily, weekly, and monthly goals should align to your annual goals which should align to your long-term goals.

Your plan should include specific metrics you use to measure success (or lack thereof). Whether it be revenue growth, deals closed per month, client retention, or projects completed, you should establish some critical numbers, establish what’s good, okay, and bad for each, and work towards and manage to these critical numbers.

2. Laser focus – You need to laser-focus on not only your strategic plan and your goals, but also laser focus on:
A) Who you are (and aren’t)
B) Who you’re trying to serve (and who you aren’t)
C) What services you provide (and what you don’t)

Crisply defining your core values, your target market, your offerings, and your value proposition this way makes other decisions (and distractions) easier to deal with. You have a sort of “business constitution” to hold every decision against.

This laser-focus keeps your efforts aligned with your strategic plan but helps you avoid chasing shiny objects (distractions not in alignment with your strategic plan). It also keeps your business out of AFAB (Anything For A Buck) mode, and makes your business scalable.

3. Structure and rhythm – Once you have a strategic plan that you’re laser-focused on, you need to implement an effective structure and rhythm to execute on it. A regular rhythm and routine to understand your business’ key metrics, to check in with your key leaders, to understand where the bottlenecks, risk and opportunities are. Your management rhythm should mirror and be centered around your strategic plan.

To really put these three components together in an accretive way, I recommend every entrepreneur, CEO, or business leader implement a business operating system, such as the Rockefeller Habits or Traction/EOS. My company uses the former.

What is the greatest lesson you’ve ever learned?
It’s hard to just single out one big lesson. Along the way, I’ve definitely learned (and re-learned) lots of smaller lessons:
1) You can’t know enough people.
2) You can’t do anything with an enemy.
3) Be financially disciplined and profitable now, or else “later” will never come.
4) Run towards your problems, not away from them.
5) Avoid AFAB, and go for opportunities with tonnage.
6) Stay laser focused, on your numbers and your plan.

What are some of your favorite books?
Without a doubt, books that have changed my outlook, how I work, and how I live are:
Rework by Jason Fried
Mastering the Rockefeller Habits by Verne Harnish
Rich Dad Poor Dad by Robert T. Kiyosaki

And for fun:
The Big Short by Michael Lewis
Too Big to Fail by Andrew Ross Sorkin
The Accidental Billionaires by Ben Mezrich

When faced with adversity, what pushes you to keep moving forward?
Sometimes, I think the answer is the desire to win. To be the biggest, the best. I hate losing (almost as much as I love winning), so when faced with adversity of any type or size, I work hard to be the smartest and fight the hardest.

Ultimately, though, what really pushes me to keep moving forward is my family. My wife and two children. They push me, support me, and inspire me to press forward, to be the best version of me possible.

What advice would you give to young entrepreneurs?
Apart from my take on the keys for success above, the advice I’d give new young (or old) entrepreneurs are:

1. If you’re still considering whether or not to leave the (illusion of) safety of a job and chart your own path, do it. Start a company. Take the leap of faith (remember Bruce Wayne in The Dark Knight Rises? Climb without the rope).

2. As you build your business, build it to scale it. Develop your strategic plan. Operationalize everything. Make every process a documented, repeatable one. This is not only a good discipline to have, but it makes growing your business possible at each stage in your company’s growth.

3. Surround yourself with great people. People who are hungry and who are smart. They’ll not only help support your own growth trajectory, but will also inspire you and give you new perspectives and insight.

Who else should we interview? Nominate someone!

Interviews are conducted for research purposes by author Jason Navallo for his upcoming book, Underdog.

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