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How 2 solopreneurs learned to mesh as a team

For a natural born leader, Fortune’s “Why Starting a Company Alone Is Never a Good Idea” may furrow a few eyebrows. With fewer “cooks in the kitchen,” a solopreneur (i.e., solo entrepreneur) can follow his or her own rules without having to worry about disagreements or an opposing business plan. But according to Fortune magazine, launching a business with “two minds that think about and approach those parts differently” may be a better idea. In the post below, Johnetta Paye, Esq. and journalist Shamontiel L. Vaughn explore the pros and cons of teaming up to start and build a business.

dsc_5150 From a personal perspective: Johnetta Paye Esq.

The end of 2008 was a transitional time for me. I recently left my position at then-Illinois Senator Barack Obama’s office. I was a newly sworn-in lawyer, and despite sending out endless applications I was unable to secure employment as an attorney. I had depleted my savings account paying my rent, bills and student loans while I was searching for a job. Being an entrepreneur is not something I envisioned for my life growing up as a child or even while I was in law school.

By December 2008, I had reached a breaking point. I figured if no one would give me a job then I would create one for myself. At the same time that I made the decision to start my law practice, one of the security guards that worked in the federal building approached me about a copyright issue his son had against rapper Soulja Boy.

I spoke to one of my legal mentors, and he advised me that the Soulja Boy’s copyright infringement matter had legs and offered to assist me behind the scene. That was my very first client matter. In January 2009, during the height of an economic recession, I launched my law practice J. Paye & Associates.

I operated as a solopreneur because money was limited and I couldn’t afford to pay a full- or part-time employee. The life of an entrepreneur is not as glamorous as depicted on Instagram and Snapchat. Building a business from nothing requires an insane amount of hard work, resilience, sacrifice and dedication.

I worked 15 to 18 hour days. I couldn’t take holidays or weekends off because I was everything to the business: the CEO, marketing and sales department, the attorney, paralegal, secretary, and file clerk.

As my business grew, I began to realize that my business growth was limited to how much I could accomplish in the course of 24 hours. Scaling to a law firm with offices in multiple states was not going to happen as a soloprenuer. I started hiring freelancers to handle the marketing, bookkeeping and event planning for my business. This gave me more time to strategize initiatives to grow my business and service clients.

In October of this year (2016), I decided to start blogging more consistently. My time is limited as a full-time entrepreneur and attorney. I still work long days, and I cannot recall when last I took a weekend off.

Blogging on a regular basis is very time intensive. You have to plan content each week, research, write and edit the blog post; look for stock photos; and create social media posts to promote the blog post. With my schedule, I knew that I could only commit to writing half of a blog post.

I reached out to a journalist that I worked with in the past on other projects. I felt that her writing was strong, and the combination of our voices together could result in some amazing content. I was elated when she agreed to co-blog with me.

In the three months that we have been blogging, we have accomplished some significant milestones. Our posts have been published on Blavity and Brown Girl Bloggers. We have planned two events around the blog. The number of daily visitors to the blog continues to increase at a steady pace.

Shamontiel L. Vaughn

Shamontiel L. Vaughn

 From a personal perspective: Shamontiel L. Vaughn

From elementary school to college, my dream was always to be a full-time author. It wasn’t until I started working in the corporate world of editing (Kaplan Financial) and picking up more newspapers that journalism really caught my eye in my early 20s. From that point, I was hooked. Kaplan Financial moved to Wisconsin, and I was hired as a full-time digital news editor for both the Chicago Defender and Chicago Tribune newspapers. However, one thing that never occurred to me was that the freelance reporting I was doing for Associated Content, Yahoo! News and Yahoo! TV would have to come to a complete halt contractually. They were considered competitors.

After a layoff of 750-plus people from the Tribune in 2013, I decided to revert back to my goal of working for myself full time as a freelance journalist. Both private and public clients rolled in pretty regularly from 2013 to mid-2015, and I had a temporary proofreading gig (cool job, but the three-hour Metra commute was exhausting). As a freelancer, I was doing everything from transcribing classified federal recordings, completing celebrity interviews, volunteering for Affordable Care Act canvassing and working on reporting assignments. Through freelancing at (now shut down as of this year), I was contracted to work with CBS Chicago (where I digitally reached out to Johnetta for an interview), and I enjoyed the diversity in assignments. But when you become a full-time, freelance journalist, the weight is immediately on you to now be a social media specialist, an accountant, a marketing/promotions manager, an editor, a fact-checker, a writer, a travel planner, a secretary and an event organizer. The idea of 9-to-5 hours becomes laughable, and it was normal for me to talk to clients anywhere from 8 a.m. to 10 p.m.

As a freelancer, you can no longer depend on a steady paycheck from the corporate world, so turning down a paycheck from one client could make or break rent that month. I won’t go so far as to say that being an entrepreneur is not for me, but there’s no other way to say this: I missed the comfort of steady income.

Without steady income, you may not have the luxury of being able to hire someone else to ease the to-do list. While I did decide to go back into the corporate world of media, luckily my current employer is OK with me continuing to be a part-time freelance journalist. And freelancing for private clients (mainly law firms/health companies via Textbroker, then with Johnetta), I am honored and relieved to write about topics that are fascinating to me but realistically just wouldn’t be compatible with my primary employer’s demographic. Plus, Johnetta was one of my favorite interviewees from CBS Chicago so it was a win-win.

I learned a few valuable lessons while working on my own though:

  • Set ground rules for when you will be unavailable or clients will work you from sun up to sundown.
  • If you’re not writing/editing things that are gratifying to share, you will be miserable.
  • Work with clients who add value to your end goals, are credible and improve your reputation instead of just offering a steady paycheck.
  • Although my major in grad school was Communications/Public Relations, I would much rather play the background and write 99.9 percent of the time. I have zero desire to be famous, just want to be respected as a journalist/writer.
  • Know your strengths and be honest about your weaknesses so you can work with someone who excels where you are fragile.
  • Don’t underestimate an organization’s networking ability solely because it is unfamiliar or less popular. You may be surprised at the connections it can lead you to (refer back to how now-closed Examiner lead me to CBS Chicago).

When transitioning from being a solopreneur to working with a partner or building a team, here are some things to consider:

Normally, this is where I, Johnetta, would give legal insight. For this post, I decided to switch things up.

Find your opposite: When establishing a business partnership, look for the ying to your yang or the frick to your frack. Your business partner should have different skills sets, strengths and temperament than your own. This helps to keep things balanced and provides for accountability. It also ensures each partner can serve a different role or function that is needed to scale the business.

Communication is key: When establishing a business relationship with your complete opposite, there are bound to be communication challenges. You may be accustomed to doing things one way. Your business partner may have a different take on how things should be done. It is important to be able to effectively communicate and work through disagreements.

Have the same goal: When working with a partner or team, it is important to have the same overall goal or vision. When things get challenging, a common goal motivates everyone to continue to push through the obstacles to accomplish the overall goal.

Put it in writing: Formalizing the relationship in a contract helps to manage friction in the long run. There’s little room for miscommunication when both parties can point to a document and say, “This is what you said.” Also, be open to improving on a contract as business expands and workflow changes.




Have more questions about business law, entrepreneurship and freelance agreements? Contact J. Paye & Associates today.

Shamontiel L. Vaughn contributed to this blog. Find out more about her at

The information contained here is intended to provide useful information on the topic covered but should not be construed as one-size-fits-all legal advice. Speak to an attorney specifically about your contractual agreement for specific terms and conditions.

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