Thank you for six incredible years - Ruben Digital celebrates six year anniversary

Ruben Digital Celebrates Six Years!

Our 6-year journey and what we are contemplating in year seven!

Last night my phone died before I went to sleep. I had a choice to make; put the phone on the charger overnight, or go to sleep and charge it in the morning. I chose the latter, and I am ever grateful for this decision.

At first glance, this scenario appears as a rather insignificant fork in the road. But looking at what this decision created, I am reminded there are no small choices. Every decision we make matters, and one by one, these decisions weave the fabric of our lives.

Ruben Digital - Celebrating 6 Years - Getting Started
Pain as the Catalyst: My Original Fuel to Build Something!

Headed into 2014, I had spent a lot of time bouncing around from job to job. Since my first job as a seven year old working at my grandparents’ car wash, I have worked close to 20 jobs up until this point. Even as a kid, hard work ran through my blood. Turning 21 in January of 2014 was an awakening. I realized I would never reach my life goals by working for someone else. It was time for me to build a business of my own. I wasn’t exactly sure what I was going to create, but I knew I needed to start soon. Later that spring, I had a romantic relationship crash and burn in the worst possible way.

“I’m pregnant. I want to get an abortion. I want to break up with you.”

I was crushed. What hurt the most was knowing that we both loved each other, but she knew neither of us was in a position to raise a child. That heartbreak led to the realization that I needed to be fully self-sustainable before I could ever truly love and support another person. Without knowing it, I closed the door to my heart, locking away love and vulnerability as I set out to build Ruben Digital Media at all costs

Don’t build a business like I did. In the beginning, almost everything was a great example of what not to do. I had a vague vision, but no plan. I couldn’t articulate exactly what problems I was solving for clients. However, through all of those mistakes, I managed to get a few things right:

  1. Building a business and not a pitch deck
    After the explosive energy surrounding Silicon Valley permeated our society with tech startup success such as Facebook, Twitter, Uber, and more, it seemed everyone was trying to build the next great startup. I despised that cultural shift. For me, my goal was not to sell investors on a pipedream and raise money. Instead, focus on a traditional model based on profit and loss. What business activities would generate more money than it cost to run this business? Simple. When I started, I was earning just below poverty wages, so my goal was simply to earn more money each year. Currently, Ruben Digital has generated more revenue each year, and my personal income has risen at a far greater pace than it would have in the labor market.
  2. Spending extraordinary amounts of time learning new skills
    As a “jack-of-all-trades”, I am blessed to have been born with many natural talents and what some may consider an “unnatural amount of self-confidence”. In high school, this made me cocky and arrogant. In 2012, reality humbled me after dropping out of college and falling on my ass. I realized that natural talent was only a foundation. To become extraordinary, I needed to develop an incredible work ethic to accompany my lofty goals. Someone once shared that having high self-esteem requires doing esteemable things. I worked on clients’ projects during the day, and then I’d spend all hours of the night teaching myself new skills. I highly recommend the following websites for DIY learning:,, and YouTube.
  3. Saying yes and figuring it out later
    Many of my clients have heard me say, “Everything I can do for you is something I had to learn myself.” Building my reputation on honesty and transparency, clients always understood what services I could provide for them. When there was a challenge to be met, I consistently rose to the challenge and learned how to solve it. Thankfully, most of the time this method worked!
A Family Affair: Bringing in the Best Support!

By winter 2015, I had enough data to believe Ruben Digital Media would be successful. I had offered such a diverse range of services to my clients to know that I could not do it all alone. At the time, my sister Hannah was already working in marketing for a local family-owned business while earning her degree from Harper. I knew Hannah was a very self-driven worker, and wanted the opportunity to expand her skill-set around social media and digital marketing. In fact, her previous boss boasted that she was the best employee he’d had in his 40 years in business! My mom Michelle and I already had experience working together at a durable medical equipment company where she proved to be an excellent office manager with incredible people skills. Entrepreneurship, work ethic, and family businesses are in our genetic code, so naturally I was excited to extend them an offer that changed the course of our lives.

Ruben Digital - Team - Hannah Ruben
“Work with me as an unpaid intern for six months! I will train you and meet with our clients to offer them new services that will utilize your skills. After that, you’ll each be offered with a full-time position and the best salary possible. Are you in?”

Hannah and Michelle showed up and each gave their 100% to Ruben Digital Media from day one. I was proud to call them my first interns! A common mistake business owners make when hiring is expecting to find employees who will work as hard as the boss does and care as much as well. It’s foolish and selfish. No one should care more about your business than you do. However, their love and support expressed by their long hours and late nights was the closest thing possible to my level of care and commitment.

Ruben Digital - Team - Hannah Ruben
Ruben Digital - Team - Michelle Ruben
Investing in Community: Establishing our Intern Programs

After finding success with that initial business model, we created a two track internship program to continue scaling. We offered a three-month internship program for school credit, and then we offered a six-month intern-to-hire program. This latter program brought us our first non-family employee, Angela! It was truly an honor to provide an opportunity to a fellow Harper grad. I had the gift of witnessing someone with a great work ethic and passion for marketing evolve into someone ready for the workforce. My favorite part was when we were finally in a position to offer her full-time employment and she got to escape retail misery!

Techies in the Making at Forest View High School - Ruben Digital

Throughout the years, we offered several niche programs as well. I took on a crew of three passionate high school boys and taught them how to develop a WordPress portfolio. At the time, I had an all-female staff and was grateful for the male bonding. That same summer, I led a three-week program teaching WordPress to a group of high school students at Forest View. All of this teaching experience helped me hone my own skills as well. Best of all, I got to see the spark in a young person’s eyes when they go from a blank screen to a finished page they created! There are few moments I’ve enjoyed more than that.

Excellent Team - Ruben Digital celebrates six year anniversary

As our client base continued to grow and their needs became more extensive, it was time to level up and bring in a proven industry veteran. It was my great pleasure to hire Ynez, a social media guru! Ynez had previously run her own extensive operation, but had shifted her focus to spend more time with her family. Once Ynez became fully integrated into the RDM team, she played an instrumental part in elevating our marketing skills to the next level. Together, she has inspired us to cultivate our solid company core values which we deliver thoughtfully through our marketing messages. I am beyond grateful for how she has helped us positively impact and inspire our clients, community, and the world around us.

Community Pt. 2: Getting Involved and Giving Back

There is not a doubt in my mind that Ruben Digital Media could not have grown to the heights we have without the love and support of our friend and client Frank Karkazis. In June of 2016, Frank introduced me to Kathi Quinn at the Northbrook Chamber of Commerce. Meeting Kathi changed my life and Ruben Digital Media forever. The Northbrook Chamber connected us with hundreds of business owners, encouraged lasting friendships, and in turn significantly grew our client base. Over these past four years, our annual revenue has grown more than 400%!

Getting Involved and Giving Back - Ruben Digital celebrates six year anniversary

As our business grew, Ruben Digital Media discovered numerous philanthropic opportunities we each felt passionate about. Our website has an entire page dedicated to some of the amazing non-profits we volunteer our time with and continue to grow our community outreach. It is actually my favorite part of what I do, and has been a privilege to share these events with my team. Over 80% of our advertising budget comes in the form of supporting non-profit and community organizations, and it is my hope to transform the mindset of other businesses to follow suit.

Getting Involved and Giving Back - Ruben Digital celebrates six year anniversary
Going for Growth: Goldman Sachs 10KSB

2018 was a catapulting year for us. We dropped “Media” from our name and became Ruben Digital. We had just surpassed a major revenue goal and I knew what got us here wasn’t going to get us to our next goal. Another life-changing relationship built on this journey was meeting ActionCoach PJ Wieland. PJ is an excellent mentor, advisor, coach, and importantly a friend. After fellow chamber member Paul Kaufmann recommended me for the Goldman Sachs 10,000 Small Businesses Program (aka 10KSB), PJ was instrumental in preparing me for this journey and keeping me focused while growing Ruben Digital.

10KSB changed my perspective as an entrepreneur forever. I stopped looking at my business as just what we do, and I started focusing on how it was the vehicle for the change we wanted to create in ourselves and our community. We took a risk and developed a relationship with an incredible banker and mapped out a growth strategy. While I am forever grateful for the friendly terms and massive support my parents were able to provide me financial via term loans, it was time for RD to get legitimate outside funding. This risk was one of the best ways to support my team as we added more pieces to the puzzle and took on larger projects.

Goldman Sachs 10,000 Small Businesses - 10KSB - Ruben Digital celebrates six year anniversary

When COVID-19 recently hit and businesses were scrambling to get approved for the PPP loan, my banker Rudy Gonzalez had submitted my application on the first day they were open. Even better, Rudy worked that weekend so the funds were in my account on Monday afternoon. Goldman Sachs and CIBC have been lifesavers for RD’s cash flow. I highly recommend developing a relationship with a banker who makes time for you!

In this time of explosive growth, I also blossomed as a young man. I moved to River North where I started consciously reconnecting with my emotional nature and spent quite some time dealing with past emotional scars. Reading several spiritual and mindfulness based books changed my mindset and opened my heart to being loved by another human being. During that process, I reconnected with a woman who I’ve known since middle school. We started seeing each other casually, and today I am proud to call her my fiancée. Te’Asia has become the wind in my sails and I have become a rock for her. Together we let love guide us to new challenges and it has been the greatest chapter of my life yet!

Beautiful Fiancee TeAsia - Ruben Digital celebrates six year anniversary
Dealing with Adversity: Streamlining Our Focus

While the overall trajectory of Ruben Digital appears to be a straight shot upwards, the reality has been more of a rising wave. In the first half of 2019, I had one of the hardest years in my personal life. I experienced my parents divorce, family mental & physical health challenges, helping my father relocate across the country, and dealing with my own professional five-year burnout. In May, I made a decision to get away and reconnect with my purpose. I spent time with family in Florida and then retreated for 11 days in the Sivananda Yoga Ashram in the Bahamas. Best decision ever. Not only do I think that “brain break” saved my life, it also saved my business.

The retreat fostered clarity, rest, and resiliency. Pushing family troubles behind me, it was time to refocus on the business. Our model was starting to falter as clients came and went. Collectively, we decided to double down on our strengths and find ways to make ourselves more valuable. Since realigning our processes and changing the way we choose to engage with potential clients, we have experienced the greatest period of financial stability and personal life balance in the company’s history. I owe this success to the combined love and guidance of all the people I have been blessed to be surrounded by.

What Matters Most - Ruben Digital celebrates six year anniversary
Speaking Out: Saying What Matters Regardless the Cost

Over these six years, I have witnessed many major moments in history and changes to our society, especially as it pertains to social media. Prior to starting Ruben Digital, I hadn’t been an active social media user for two years. My job at the time required some interaction but other than that, I was off the grid. After spending considerable time developing an audience, I have realized that social media does more harm than good. I do not resonate with the philosophy of making as much noise as possible, and I have adopted a “Post Less, Say More” attitude.

Taking the opposing viewpoint, I have also experienced the benefits of being adept at a holistic approach to digital marketing. Our social media profiles, email marketing lists, website blog, and video marketing has allowed Ruben Digital to express our viewpoints on social issues and encourage our audience to take action and get involved. I believe that my purpose here on Earth is to serve others, and it has been a great joy to serve my community in this fashion. I have most enjoyed the collaborative approach our team takes to having difficult conversations and then bringing those private conversations public. As we most recently participated in #BlackOutTuesday, I am proud to see how our team listened to each other and were able to make a decision in realtime to speak out on what matters most.

Ruben Digital Black Out Tuesday - Ruben Digital celebrates six year anniversary

Back to the Beginning: To Charge or Not To Charge

There are no small choices. Every decision matters. Do the things you dedicate your life to bring you joy and fulfillment?

Why did I start this post writing about a seemingly insignificant decision to wait until morning to charge my phone? That decision helped me break up a habit I had formed this month. I typically start my morning with prayer, meditation, breathwork, and a cold shower. However, with the tumultuous times our country has faced, I found myself waking up exhausted and checking social media to “wake up my brain.” This has led to entering the day feeling drained and depressed.

The choice to charge my phone in the morning gave me the space to resume my routine, something I have spent eight years cultivating. That decision gave me the space to meditate and listen to what was on my heart. I’ve been so wrapped up in the state of our country that I actually forgot about our company’s 6-year anniversary. Can you imagine forgetting a loved one’s birthday, or your wedding anniversary? I decided this story needed to be told – I wanted to share something meaningful with those who’ve been along for the ride.

My Wish For You: Create the Space to Contemplate What Matters Most

Sobriety. Spirituality. Family. Health. Peace. These are the things I value most. Whatever your list looks like, I pray that you find a way to give yourself that space to connect and grow. You never know where it will take you. I did not plan to be where I am today, and there is no telling what my future holds. But what I do know is that it will be a brighter place because of all of you.

Thank you for all the love and support throughout these six years. What a rollercoaster it’s been! No man is an island. I could never have made it this far without my family, friends, staff, clients, networking partners, and aspirational examples. We never know what life has in store for us, and the uncertainty and obstacles certainly keep things interesting. Thank you for taking the time to read this reflection and for being part of Ruben Digital’s story. Much Love!
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