In honor of National Women’s Small Business Month, I got the chance to catch up with my dear friend and fellow Spelmanite Anika Jackson, President of Jackson Land Holding, LLC. Unlike most, Anika developed an acumen for business far beyond her years early with the help of her father, Gregory Jackson, one of the nation’s most prominent and respected entrepreneurs. We chatted about what entrepreneurship really means to her, her trendy new clothing line and how she plans to make her impact while continuing her father’s legacy in Detroit. Enjoy!

​Jackie Palmer: You come from a family that’s full of the entrepreneurial spirit. What was that like growing up?

Anika Jackson: Growing up in an entrepreneurial family, I immediately knew my destiny. From my chores to toy selection, my parents taught my brother and me to evaluate everything as if it were a business decision. ‘Do you need that toy? What’s the purpose of this toy? Do you really need another one, when you have 4 that are similar?’ And that atmosphere still remains today. Whenever I visit my parents, we discuss different business decisions that impact Detroit, our own businesses locally and nationally, even the different political decisions. My family discusses Detroit as much, if not more, as you and I do when we gather with friends, who understand how important it is for us to lead the change in the city of Detroit. So, growing up my parents constantly discussed with us the events and decisions that were being made in the city, the state, and the country. No political or business topic was too inappropriate for us, because they wanted us to be conscious of the world and the space that we live in. In 4th grade, my brother and I started a vending machine company. The machines were placed in our car dealerships. Back in the ’90s, people could sit in a dealership for 1-2 hours and would get pretty bored and tempted by a vending machine. Remember, there were no cell phones to keep you entertained. People were going to eat and drink and it was a pretty lucrative business as a kid. As I reminisce, it’s probably something I should revisit for airports (she laughs). Those machines are high tech now! As kids, we were taught to restock the machine and verify our accounts. Which was super important because we learned to balance our inventory and determine if someone was stealing from the machine, any glitches, or price increases. I remember having my friends help me stuff my quarters into the rolls before I could go out and play.

My parents started out owning a couple of apartments when I was younger. They rolled those profits into a cookie dough business, which was wholesale based. They sold the dough to Hudson’s and then Marshall Field’s. It was the dough that made the cookies in their cafe. So growing up, we always had a variety of businesses that kept everything exciting. But my father always taught us the same fundamentals of knowing your product inside and out, know your customer, and understand your financials fully so you can identify if someone’s stealing from you. You have to understand what it takes for profit to trickle down to your bottom line, whether that’s too much overhead, overspending on marketing or product expenses are too high– we always talked about those things and still do.

JP: So, what advice would you like to offer to women who are on their journey to build their empire or climb the corporate ladder? You’ve done both and done both paths successfully? What are some of the commonalities on those paths that helped you?

AJ: So, I’m going to be candid, because we are friends. My path is a little unique because we have a family business and my goal is to take us to the next level. As far as building an empire, I don’t feel I can fully speak on that. I am still working on my empire, especially with my fashion line, Wink City. My task with our family business is to expand our empire because it was already built. But I refuse to be the stereotypical second-generation entrepreneur, who can’t elevate our business. Those goals are real for me. As for advice that I would give to budding entrepreneurs:
(1) Always be a student. (2) Connect with people. (3) Understand and appreciate every experience that you have. When I was younger, there were things I just did not want to do. Ultimately, all of those experiences have helped create who I am today and all happened for a reason. You have to embrace those life lessons, every one of them. Don’t ever think that anything is too insignificant, because you will likely use that skill or a need for that knowledge somewhere down the line. Its purpose will manifest itself. (4) Be your biggest cheerleader. I have a tendency to not do that because I don’t want it to give the wrong impression because of my background. But you should always take the opportunity to promote yourself when there’s an opportunity. (5) surround yourself with those who are like-minded. I know it’s super cliche. But honestly, my entire mood changes when I’m around other entrepreneurs like yourself or Niles Heron (of Michigan Funders), Amina Daniels (of Live Cycle Delight) and one of my best friends, Kelli Coleman (of Global Hue). That energy resonates around you and reminds you that nothing is out of your reach.

JP: Coming from a  family of entrepreneurs, you probably already had plenty of mentors. What would be your advice on finding a mentor to make sure you are growing?

AJ: I have honestly struggled with that sometimes. Next question, just kidding. (she laughs). For me, it’s been a great gift and a sweet curse, because most of my mentors have come from my family connections or been blood relatives. So I haven’t had to really search high and low for a good mentor. However, I will say that what I have seen as a proven method of success from others is to connect with others who are in the circle you are trying to build a foundation in. I wouldn’t ask someone to be my mentor. I would create a genuine relationship through attending events and grabbing lunch or dinner together.I think that’s way more valuable and impactful in building a mentor/mentee relationship,rather than just selecting someone based on their name or credentials.

JP: So, what’s next for Jackson Asset Management, Wink City, or Jackson Land Holding? What are your next big goals?

AJ: For Wink City, I have to expand the line and products. I have to spend more time running the actual business and stop treating it like a small project. My goal for Wink is to increase brand awareness, set a sales goal and exceed it, expand the line and create a physical presence at a brick and mortar location. For Jackson Asset Management and Jackson Land Holding, the goal is to continue expansion. That means investing in additional real estate across Detroit, the market is exciting right now. So, finding additional assets (residential and commercial) in the fringe neighborhoods of Downtown, Midtown and the Central Business District of Detroit. Also, improving our brand awareness is a huge task of mine. People understand us they way they do the Gilbert brand, but not our sub-company’s. I have to improve what that umbrella looks like to the public.

JP: Now, time for my favorite question: What did you want to be as a child and now what do you want to be when you grow up?

AJ: Hmmm… I want to wake up every morning and be fabulous! Just kidding, but I am serious. Honestly, I really don’t remember wanting to be anything but a business owner. (she laughs) In high school, I really wanted to own restaurants. And now, that’s still true. I want us to own more entertainment-esque entities. We have a golf course and its beautiful. So I’m excited about that because it was such an excellent opportunity. We do a lot of events and weddings there. I really want to add on to that asset type. I’ve realized that there’s so much more we can add to our portfolio. But I do want to say that you don’t have to focus on just one thing. You can be multi-faceted. It’s the true key to wealth. You have to diversify your income. So often, we are taught to go to school and become a doctor or lawyer. To really grow an empire, you need diversification. And that’s not any shade to those professions, but real wealth comes from income diversification, and we aren’t always taught that.

You can check out Wink City online and follow them on Instagram!

Remember, give your brand the good life!