Rich Rudzinski; Exploring the Hurdles of Going From Solopreneur to CEO

person-iconby Ed Parcaut calender-icon19 Mar, 2021

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On our latest installment of the Inner Edison Podcast, we talked with the CEO of Tragic Media, Rich Rudzinski. We talked about his rise from employee to solopreneur and consultant to becoming a CEO.

Tragic Media is a software and technology solutions-based consulting firm based in San Diego that Rich started in 2008 during the economic downturn when work was hard to find. Since that time, he has turned it into a full-fledged brand that has helped great companies like Intuit, Qualcomm, Lego, and Pixar find solutions to their most pressing software problems.

Rich candidly shared his learning experience at each level the mindset shift required to grow his software business, Tragic Media.

Becoming a Consultant and Solopreneur

At the height of the economic downturn in 2008, Rich found himself looking for a new challenge in his work. The only problem, no one was hiring. He had worked for a couple of years at a local agency but felt he had hit the ceiling of what was possible in his position.

So he decided to do some consulting as a solopreneur.

With the skills he had picked up from his former agency work, he started to build a client list of top-level businesses looking for solutions to complicated software and technology problems. Even with the work coming in, he found it hard to switch to the mindset of a solopreneur. “I quit my job and just started focusing on doing consulting while I was looking for my next full-time gig.”

He started to realize that a full-time gig wasn’t what he needed. “At some point, I realized, like, I need to stop looking for a job because I have a job right here.”

Hiring Employees and Getting Lost in the Weeds

Before long, he had so much work, he needed to hire employees. He comments on the mindset change that he had to go through when pitching his business to clients. “One of my first hurdles was like, how do I get people to pay me for someone else to do the work? You know?”

He reiterates that it was just him and his solopreneur gig for a long time, now becoming a company created new demands and new challenges. “And like, I was the expert. I was the specialist. They hired me to do the job, but now I’ve hired two other people, and they’re going to do the job.”

He realized it was a mindset shift from a solopreneur, consulting side business to a full-fledged brand. “It’s totally a brand move. It’s about changing the messaging, you know, of the company and its sales process.”

For a long time, he used to get stuck in the weeds of the work until he realized he needed to step back and work on the business rather than working in the business. “ One of my biggest hurdles in the company was a couple of years back. I was stuck working too much. Like, you know, it’s very kind of cliche, but working too much like in the business instead of on the business where I was too deep in the weeds of a project.”

Learning to Be a CEO

He credits becoming part of a mastermind group of CEOs has helped him transition from a solopreneur to a boss to a CEO of a business.

It’s helped him realize where he fits within the company. “I’ve found that I really need to be the head of business development.” He explains how he has tried to find people to fill that role, but it hasn’t worked out.

He clarifies, “Like if I’m not out there, um, you know, connecting with people, you know, uh, helping to make sales, you know, helping to build the brand, then nobody else is really able to fill that role.”

He recognizes a lot of his growth as a CEO has come from learning from his mastermind group, “when you find that person or you find that group, it’s, it’s a game-changer because all of a sudden, like it, just opens a lot of doors, both in terms of like your network and everything. And then also brings a lot of outside perspectives.”

Looking for More Great Content?

Be sure to check out Rich and Tragic Media if you’re an entrepreneur or business in need of software solutions.

If you’re looking for more great content about entrepreneurism, head on over to the Inner Edison Podcast and check out our full list of interviews.