Interested in starting your own entrepreneurial journey in business development but unsure what to expect? Then read up on our interview with Jessica Dragan, Founder of Corporate Wellness & Retention, located in Milwaukee, WI, USA.

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

I am a Private Equity Investor and Consultant for businesses that need to sell because of retirement, distress, life changes, burnout, or simply just want to do something else. I offer a fresh set of eyes for business owners to increase revenue/value and lower fixed costs. You do not have to sell the business if you use my consulting.

Tell us about yourself

Well, I fell into business completely by accident and realized it suited my personality better. When I finished my military commitment, I went to massage school. The internship there taught me basic business skills. After spending months of a job search(in other industries) while I was in school, I discovered all the positions I was interested in were commission-based, which never made sense to me. The School told us we could take our clients with us from the internship when we graduated. So I did, and at some point, the school realized they were losing money and gave the clients an offer we couldn't compete with. That was my first "mini-pandemic." My friend started advertising me, and the next thing I knew- I had a full-fledged business, and it even paid me better.

I was obsessed to learn and grow the business. I spent my time learning SEO marketing and building my website, which paid off very quickly. By 2017 I had hired my first employee, and by 2019, I had a staff of 31. 2019 was a very rough year for me, and if I knew then what I know now is that the moment I started hating my business- I should have sold it. Then the pandemic came and crushed my business, but I was excited and could not wait for what was next. I ended up managing a mini-golf course that was owned by three brothers who inherited it from their late mother. They hated that thing and basically handed it over to me. One of the owners was my mentor, answered any questions I had, and stood by my decisions. It was such a great experience- one that I am very proud of. I gave the location a facelift, changed the staff, built and maintained relationships. We even received an award from the State Senator. While I was involved in the mini-golf center, I found a group of investors who were acquiring businesses and doing exactly what I was doing, except I was an employee at the time. I knew that was what I wanted to make a career of, to be a Private Equity Investor. I do it because I love people and a challenge. But I do this also because I care about what happens to people and the community.

What's your biggest accomplishment as a business owner?

You stumped me on this question, lol. I was having a rough week and not feeling very accomplished, even though I had tons of accomplishments. So I took out my paper and a pen and began to write them down. What stands out to me is all the friends and partners I have. They are all my most valuable assets. If I have any questions, I know who to turn to. And they are all so smart, talented, and experienced. I recently even got a referral from someone I haven't spoken to in 10 years.

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

I think maybe all the choices. When you want to hire someone to market your business, for example- I have not mastered the art of choosing the person that will actually bring an ROI. There are so many people that seem to do the same thing, but there are so many factors in choosing the best one. I have learned to ask my circle before hiring someone instead of trying to do that myself. Another good idea is to read about the subject, so you know that what you are asking for is possible and you are more equipped to give better direction. Learning a little bit about what the person is supposed to do is time-consuming but will protect your cash flow better than not knowing what they should be doing.

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

  1. Be strategic in your actions. Careful thought on how you run your business for the long term is essential. You have to think looooong term. When I was pursuing government contracts, it wasn't just to get a contract- which would have been very sweet, but it was also to get to know the companies who were selling to the government as well as to get to know the community and private business.
  2. Do not be afraid to scrap any ideas and begin to redo or restructure them. I had bought a billboard once to get the word out about my business around town. The graphic designer designed it, and I hated the whole thing. When he made his changes, it was only in the same format and look. I asked several times to redo it completely, and he refused. Finally, I gave up and just approved it. Well, the billboard did not work. It had a lot to do with energy; I was really unhappy and embarrassed. I never used them again.
  3. Appreciate everyone and everything. I learned this lesson very early on from a woman who had a dog that was paralyzed by a gunshot wound, and she decided to rehabilitate her. As you can imagine, the dog required a lot of care and a team of people to help. Funding was an issue, and the lady used appreciation to get the care as far as she could. It was an effective strategy, but she also meant it. She is a lovely woman, and it really made a difference in how I treat people.

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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