Chicago Female Entrepreneurs Are On The Rise: A Look Behind The Success Story

Chicago Female Entrepreneurs Are On The Rise: A Look Behind The Success Story

While men are more likely than woman to become entrepreneurs, Chicago, in particular, has made great gains for female entrepreneurs. Chicago was recently named the world capital for female-founded startups, with 30 percent of startups started by women.

There’s a lot of advice from successful entrepreneurs, and I wanted to spotlight some advice I learned from one of Chicago’s newest female entrepreneurs Lakesha Rose, who recently launched her own online lifestyle magazine, Rose Phillips Online this year.

Rose is a 15- year veteran to the women-owned business world in Chicago. She discussed with Windy City Cosmo about the differences in being a business woman versus starting something new as an entrepreneur. We also discuss work-life balance, the importance of media, and how we all need that one person to believe in our vision as much as we do.

The Tears and Stress Behind Startups:

We hear so many success stories of how entrepreneurs are successful, but Rose gave me the truth.

“I lost sleep, I got grey hair and because in the early months of creating Rose Phillips Online I knew I wanted to showcase local businesses on a digital and broadcast platform to promote our local community commerce but getting there and presenting a viable product was a different story. Since I couldn’t really explain how this would work in the early days I couldn’t ask investors to be apart of my plan since I didn’t have the entire story so I funded the idea…the good and the bad.”

Rose started her career with the interior design business which she identified as an easier business for women to get into.

When Your Clients Believe in You:

“I was an entrepreneur (before) but not at the level and depth I am now, this process changed me as a human being. My god, if you want something, you have to keep pushing. I hit the brick wall three times.”

Rose Phillips Online is a multimedia online magazine that celebrates local business in digital and broadcast events in Chicago.

One of their most recent interviews was Julian Green VP of Communications and Community Affairs with the Chicago Cubs.

“It just takes that one person to open the door for you and believe in you,” Rose said, “I like how we are progressing.”

Rose mentions that with local TV stations, small businesses have limited visibility because they have to spread out their appearances to about every quarter or more with Rose Phillips Online you can appear as often as you want to be seen and heard.

But she still finds these platforms valuable in promoting her business. Rose has relationships with producers from You and Me This Morning who helped her promote Rose Phillips Online.

Every entrepreneur knows that creating a business is one part, but promoting it is another. Rose Phillips biggest platform is Facebook right now.

The Importance of PR for Startups:

After 13 months of building her platform with the person who helped get this project started her creative director, Rose now has a team of 10 people who help make Rose Phillips work. Rose hired a PR firm Samantha Frontera- Exclusive PR to help her with press coverage.

Building a Network Through Chamber of Commerce:

She also works on growing business relationships on her own. One of the greatest sources she looks to is the local chamber of commerce.

“If you want to get your name out there – go to every event. Everyone is there in that room for the same thing – how can we partner and support. their guard is down,” Rose said.

Finding support through business in invaluable. But so is having a home base of support.

Life is a Triangle: Work, Family, Social Life:

“My husband was my biggest advocate, he would hold my hand when I had a pity party moment and push me off when I needed to get started,” Rose recalls, “If you are an entrepreneur, you are married to your business. In the dynamic with my husband and I he was already successful. He was my biggest supporter – there was no tug and pull – he could stand and support. It’s the best partnership.”

While Rose developed her business and had the support of her husband, she also touched on the fact that when you are building your business there is a lot of sacrifice.

“Literally, I didn’t see my friends for the year,” Rose said.

“Life is like a triangle, you have work, your family and your social life. In order to have a successful career, you can only choose two while on your journey to what you want to achieve professionally, something has to be sacrificed in order to get what you want, so choose carefully.” Rose said.

Are you a female entrepreneur? Windy City Cosmo would love to hear your story. 

Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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