Interested in starting your own entrepreneurial journey in personal and business development but unsure what to expect? Then read up on our interview with Jessica L. Williams, Founder of Tech Biz Gurl, located in Chicago, IL, USA.

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

I help those who love their 9-5 and want to be entrepreneurs by giving them the resources and support to make their businesses more manageable while juggling other things. Think of me as a Side Hustle Cheerleader.

There is a lot of pressure out there to entrepreneur a certain way. But businesses, side hustles, newsletters, and passion projects come in all shapes and sizes. My mission is to offer gentle nudges (and perhaps, a different perspective than you typically hear) to help folks build a business in a way that works for them.

Tell us about yourself

In 2011, I was working on a client project and feeling burnt out and lost in my career. So I went to Spark & Hustle, a conference for women entrepreneurs. And it was there that I realized that while I didn’t consider myself an expert, my business and tech background gave me some knowledge to help these women. That event sparked inspiration, pun fully intended, and a week later, I bought the domain for My goal was to create a space for folks to go after their online business dreams without technology holding them back.

My business has evolved and shifted as I have changed jobs and learned more about myself, and it hit a real turning point in 2016. After helping co-manage a program for women startup entrepreneurs, I realized how important the side hustle was. Not only is it a way to test an idea for entrepreneurship in a low-risk way, but it is also an opportunity to pursue a passion.

Also, for many women, especially women of color, quitting their job and going “all in” on being an entrepreneur is not always an option. Not for me, as a caregiver, for example. I wanted to provide another way. As I had a lot of experience and resources to add to the conversation, my messaging and content shifted to connect side hustlers with resources to get started.

What's your biggest accomplishment as a business owner?

Recently, I published the 300th issue of my #jesspicks newsletter. It was something I started in 2016 as a way to provide value to my audience, as I needed time to figure out what I was doing with the business. It took advantage of a strength of mine: curation. And I have been able to grow it over the years to 1,500 subscribers.

It has become a place to share lessons I’m learning, experiments I’m trying, and how I’m managing (or not managing) all the things. Everyone should be able to have a fulfilling life, whether working full-time, being a full-time entrepreneur, or combining both.

Each week it warms my heart to see and hear entrepreneurs, creators, and freelancers walking away with a tip or nugget to keep moving forward in their lives and businesses, having grace with themselves through it all.

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

As a side hustler, finding the balance is often challenging, and sometimes I wonder if it’s worth it. Most people work 8 hours a day and go out to a happy hour or home to relax. But, you instead are choosing to go home and work for another 2-3 hours or start your day early. It’s not an easy road at all. Sometimes, you will want to throw your laptop out the window or shut your business down on those challenging days. But just hearing that my words made a difference or my story has helped someone else is all I need to keep going.

It’s helpful to remember that it is not about those big pockets of time. It’s not about the two hours here. The three hours there. It’s more about those consistent 15 or 30-minute time blocks you spend on your business.

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

  1. Get clear on why you want to start a business. Is it to make more money or have more freedom in your schedule? Do you want to solve a problem you see in the world? All of the above? Whatever that reason is, it will be essential to keep it in your back pocket on the hard days. And trust me, there will be hard days.
  2. Think of this business journey as an experiment. As my fave coach, Michelle Ward, says, “Put your Nancy Drew hat on.” It takes the pressure off of getting everything perfect and giving yourself space to try different things. And even if something doesn’t go well, you can learn from it and take it to the next experience.
  3. Make time for self-care. We often prioritize everything other than ourselves (guilty!), but taking this time will help us do even more for others and ultimately be better business owners. Self-care is not all about manicures and bubble baths. It’s about doing the activities that make you feel more like you. It could be as simple as making time to read before bed, getting your required sleep each night, or going to a dance class, which are a few of my favorite ways to recharge.

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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