Interested in starting your own entrepreneurial journey in technology but unsure what to expect? Then read up on our interview with Jordan Hewitt, Owner of Damn Good Technology, located in Portland, OR, USA.

What's your business, and who are your customers?

I provide technical expertise to support medium and small businesses on their path to success. I especially love working with folks who have complex challenges and who are hungry for ambitious goals that everyone else is afraid to tackle.

Tell us about yourself

I first got interested in tech in high school. As I'm more of the creative type, thinking logically in a sequential pattern was a major challenge, and I was often behind my peers in understanding. But this was early to mid-00s when open-source software started to become more of a mainstream topic, and I was attracted to the potential of open source to level the playing for everyone and spur innovation.

I began thinking I'd go through the "standard" route but found I kept finding roles that were not a good fit. I think my mindset was, "I can make this better!" which--as a grunt worker--a boss is not looking for. But I found that mindset serves my clients who are looking for a better way to do things.

I strive to improve and innovate current solutions. Today only an elite few hold power over people's tech lives, and that sickens me. I work every day to loosen the stranglehold tech has on people and put folks back in control of their data, their lives, and their business.

What's your biggest accomplishment as a business owner?

It may sound simple, but getting up every day with an attitude of service. As someone who battles dysthymia (a form of depression), anxiety, and ADHD, the temptation is there to curl up in bed in the morning and just let the day pass by. While I do have a strong motivation to hit the day strong, oftentimes, my mental health pulls against that. So I've had to adopt habits of highly successful people (and get support through friends/doctors/therapists) to take ownership of my morning and my day in order to serve clients and other people.

What's one of the hardest things that comes with being a business owner?

Knowing my limits. It's not my job to save my clients' companies. I always want to support everyone all the time, but I always have to face the fact that I'm human. Support my clients, absolutely. Provide quality service, absolutely. But if a product is sinking, I don't have to save it. Sometimes letting someone fail results in a better outcome for both parties. Otherwise, we risk entering into a codependent relationship. Codependency never bodes well in romantic relationships or business relationships.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. You don't have to quit your job and then start a business. The vast majority of successful entrepreneurs work on their business on the side and then make the leap when it's safe.
  2. Work on the process, not the goal. Learn from every failure. Lean into what works.
  3. You can't do this alone. Find people who support you but are still willing to call you out. Whenever you meet someone new, ask yourself if this person is getting you closer to your goal or pulling you away.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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