Alright – so today we’ve got the honor of introducing you to Rich Rudzinski. We think you’ll enjoy our conversation, we’ve shared it below.
Rich, thanks for taking the time to share your stories with us today What were some of the most unexpected problems you’ve faced in your business and how did you resolve those issues?
After a few years of running my software development agency, we started to gain some great traction. We were a team of ~5, and we landed a big software project with a solar finance company based in Northern California, which took a large portion of my team to execute. We were leading the strategy, design, and development; while working collaboratively with internal team members to execute. The project went great, and we worked to outline, design, and develop a beast of a user finance portal. Then several months in, we got the rug pulled out from under us, and as a result I almost lost my company which I had been building for over 5 years.
Unfortunately, I made the classic mistake of “working IN the business instead of ON the business”. This was a big project, and I got sucked into leading the strategy as well as managing the design and development team to ensure proper execution. Then, the project ended abruptly when the company decided to pull the remaining development work internally. Because it was such a large portion of our work, and I had failed to protect us with our project contract, our runway evaporated right before my eyes. Sales faltered as I tried to refill our pipeline, but ultimately I lost all but one of my employees in the resulting turmoil.
The one that stayed is now my business partner, and together we rebuilt the agency to new heights. My biggest takeaway from the incident is that we had grown too large for me to be involved in day-to-day project execution. I needed to be focused on our administration and growth; that is, work on the big picture of the company, and instead hire great talent to take over the tasks that I was previously responsible for.
Learning this lesson enabled us to quickly rebound, attract new clients, bring on better talent, and scale to 3x the size we were in just a few years.


As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
I am the founder of Tragic Media, a technology-focused digital agency based in San Diego, serving the world. We empower growing brands to take advantage of the latest technologies, and support them long-term with their design and development needs. We are a team of senior, US-based digital technology professionals. Our diverse range of expertise allow us to provide robust UX, UI, development, and cloud solutions to help our clients tackle their most challenging technology initiatives.
We strive to be a true partner for our clients: supporting, collaborating, and empowering them to reach new heights with technology. Our teams are hand-built to support the ever-changing needs of our clients as they continue to grow, evolve, and face new goals and challenges.
Many of our projects generally focus around: SaaS / Paas product design and development, devops and infrastructure support, serverless web and CMS solutions, blockchain and web3 development.


Let’s talk about resilience next – do you have a story you can share with us?
Resilience is one of the key reasons for my continued success. Running a digital-service business for over 13 years requires you to be innovative, adaptive, and above all resilient. The story I shared for this series highlights one of the darkest times for me running Tragic. I lost nearly everything. We had barely any clients, and one by one my team all left. I saw the company that I had broke my back for years to build, completely fall apart. I could have quit. I could have thrown in the towel. But I fought tooth and nail to survive. I convinced my one remaining engineer to stay with the company, I pushed our marketing, and I hit the pavement determined to sell and build back my company that I believed in.
Then, after rebuilding the company and brand to new heights, Covid-19 came and once again pulled our work pipeline out from under us. Every client froze their projects, all sales in the pipeline disappeared, and once again I had to stay strong, and find a way through the hardship.
My journey as a sole founder has been fraught with difficulty, impossibility, and hardship. Determination and resiliency have enabled me to push through the hardest times and allowed me to bootstrap my business to become the technology powerhouse we are today.


Can you tell us about a time you’ve had to pivot?
Staying ahead of the curve with technology has required constant pivots in the work we do, how we execute it, and even how we sell it. I am constantly testing micro-adjustments to the business which build toward bigger pivots in our solutions and engagements.
However, we took a huge pivot during the Covid pandemic. When our pipeline froze (again), we were able to acquire some government funding to stay afloat. We used these funds to invest in our own products, which has allowed us to begin our pivot from services to products. During the pandemic slowdown, we built two new SaaS products:
Drivey (drivey.com): A multi-cloud file management application for easier management of your cloud files.
Oversight (oversight.co): A workforce management and data reporting application built for agencies.
I find that moments of uncertainty are the biggest moments of opportunity. I first started Tragic during the 2008/2009 recession, and pivoted a new product arm for the company during the Covid pandemic. As business leaders, we must always be ready to shift, pivot, and accelerate through any turmoil or uncertainty that comes our way if we want to survive and thrive.
Contact Info:
- Website: https://tragic.media
- Linkedin: https://www.linkedin.com/in/tragicrich/
- Twitter: https://twitter.com/TragicRich
- Other: https://oversight.co https://drivey.com

