Chicago Defender

Contessa Gibson is a native of Chicago and works as a national account executive with the Professional Diversity Network where she oversees Diversity and Inclusion corporate sales within 13 Midwestern states, helping corporations diversify their talent pipelines. In addition to her day job, Contessa recently launched a technology venture, Plus Navigator, which delivers smart matching of customer apparel targeted to the under-served extended sizes market. She gives generously of her time and resources to support diversity and non-profit initiatives which support empowerment and the positive development of self-esteem. In her experience, “Exposure to positive, empowered women as a youth has paid invaluable dividends that words cannot communicate.”

I first met Contessa when I joined the YWCA Chicago's Future Leaders Council where she was also a member. She granted me an in-depth interview that was published on my blog last year.  I was excited when she agreed to provide a 2013 update. Here are some insights into the personal and professional sides of Contessa Gibson.   

The Personal

• Personal Motto: I opt for the Golden Rule every time, Do unto others as you would have them do unto you.
• Words of Wisdom:  It’s often not how you start, but how you finish that matters in personal and professional endeavors and accomplishments.
• Currently Reading: The Lean Startup: How Today’s Entrepreneurs Use Continuous Improvement to Create Radically Successful Businesses by Eric Ries
• Last Vacation Location: Washington, DC
• Currently listening to:  Patti Labelle Pandora Station
• Favorite Past time: Socializing with friends who keep me accountable to my personal and professional goals.
• Supported Charities: United Way, Junior League, YWCA
• Alma Mater: University of Rochester
• Home Town:  Chicago, IL
• Guilty Pleasure:  Leisurely pinning things onto Pinterest
• Biggest Wish: TODAY show feature for my technology startup
• Favorite T.V Show:  Although I gave up television three years ago, I still manage to catch episodes of The Office, a personal favorite.

The Professional

Sherry:  You recently launched your own business. Tell me a bit about it.

Contessa:  It’s called PlusNavigator, a solution designed to simplify and empower the plus size shopper to get the items she needs and desires.

What inspired you to launch your business?

A large void in the market, with an obvious failure to serving a growing population of women (size 12 and up) in the country.

Were you able to tap into any Chicago-based startup incubators?

Yes, I applied, was accepted, and graduated from the Founder Institute incubator—a program offered in 39 cities, and 5 continents that is an early-stage startup accelerator and global launch network that helps entrepreneurs create meaningful and enduring technology companies. 

What advice would you give other young entrepreneurs?

Never leave home without the two P’s: Patience and persistence, and it’s imperative that you keep an open mind while never losing your core vision.

Would you mind sharing your five-year plan? 

Huge question, in a nutshell. Continuing my personal commitment to my civic duties, continue to build meaningful relationships and give back on an ongoing basis for the next figurative ‘Contessa Gibson’ trying to figure it out.

Do you think your experience as a sales executive with SmithBucklin helped you when launching your own business?

Sure.  Every professional job opportunity that I’ve accepted, even from my statistician days at Discover Card, lend useful resources, information and skills that propel me closer and closer to my personal goals and ambitions. I seek out opportunities which create a suitable win-win-win for me personally and professionally, while also delivering great value to my employers of choice.

Read Contessa’s full-length 2012 interview while she was still with SmithBucklin and in the process of launching her business.

"The high school drop out rate for Black males is more than 50 percent." These were the words spoken by Tim King, co-founder and CEO of Urban Prep Academies in Chicago. Although this statistic is heartbreaking, King delivered this message to an auditorium full of guests who gathered at Urban Prep Englewood to celebrate. 

Despite the staggering facts of Black males dropping out of high school, 100 percent of the seniors at two Urban Prep Academy campuses were accepted into college. 

"Fact: Urban Prep seniors, these guys, have amassed more than $6 million in grants and scholarships," said Tim King.

Nikki and The City pictured with founder of Urban Prep, Tim King and some students holding up one finger (for No. 1), which signifies 100 percent acceptance into college.

This fall seniors will attend a variety of schools across the nation, including an Ivy League university and Morehouse College – one of the Historically Black Colleges and Universities. 

The Tie Ceremony consisted of seniors receiving their red and gold tie, which signifies college acceptance, and a speech from the mayor of Chicago, Rahm Emanuel.

"What this 100 percent proves is that it need not be the exception, but the expectation," said Mayor Emanuel.  

As a writer who's constantly reporting on the violence that plagues our city, it's extremely refreshing to witness something great occurring in an area least expected, to the young men we all at one point were guilty of doubting. As Urban Prep students state "We believe", in their creed, their success is causing others to believe as well. 

 Often when starting on the entrepreneurial journey, visions of huge success loom large.  It can be heady to think of the possibilities of owning your own business, when there are stories all around of folks who went from nothing to multiple millions with one idea.  The vision of huge success is one thing, but creating it is entirely another.

As anyone who has ventured on this path will tell you, it is not for the faint of heart.  Customers, suppliers and contracts come and go, trends change, recessions and market crashes re-arrange the landscape for financing...often as the famous movie line said; you better  "fasten your seat belts, for it's going to be a bumpy ride".  That's entrepreneurship...and it can be a Shark Tank.   Yet we keep going, pressing on, working to build the big dream, to make that vision a reality.

But sometimes as I've gone along this ride, moments happen that make meaning more important than ambition.  That happened again this week when our ComfortCake HUGS Foundation hosted 20 students from Urban Prep Academy at our offices as part of their Discovering Our City Initiative.  This initiative engages businesses and organizations to introduce students to parts of Chicago and career opportunities that they may not have ever been exposed to.  I'm proud that this is the second year we've hosted them.

To me, there is nothing more meaningful than to see lights of interest come on in the eyes of positive, young people.  To get their curiosity flowing about possibilities, to add to their menu of options, to field their excellent questions while sharing stories of what it takes to complete an education, start a business, and give back to others...it was priceless.  We all know that the images portrayed of our youth is much more negative than positive.  Yet, there is positivity all around us, and we can all do something with our youth to let them know we care about them and about their future, because it is our collective future.

I think it is important to let young folks see us doing what we do as entrepreneurs, whether times are good or times are hard.  Let them see that as the old African proverb says, "To stumble is not to fall, but to move forward faster".   I made those young men promise me that as long as they could look up they would get up as they go through this life.  And being with them, sharing with them gave such meaning to my soul.  This is what matters more than ambition to me.  I could have had them stay all day because of the hope they engendered in me.

What can we all do?  As our city copes with such astonishing violence and a mindset of hopelessness, we can reach out to our youth.  It doesn't always take a program or a foundation.  Sometimes it just takes a moment.  When you see youth engaging in something positive, stop and let them know it's appreciated.  When you see something needing correction, don't be afraid to correct with a loving touch or tone.   For example, this week my cable was out, and the young technician who came to fix it was on time, which was terrific.  But he came to the door with the straw from his soft drink hanging from his mouth, and started trying to go through his analysis with it hanging there!   Now, I wasn't his momma, but I just had to stop and let him know that while I was glad he was on time, that straw was not building my confidence that he knew his stuff.  I said it directly but with a smile...and he promptly got the point, trashed the straw and ended up doing a great job.  It felt wonderful to then give him high marks when a survey call came later.  Who knows, perhaps he will think about the impression he leaves when on future service calls, and the good survey marks will encourage him to succeed.

So, each one can reach one.  In a store, on the street, look young folks in the eye.  Say Hello...Smile...  Engage...say "you're doing a great job!"  We used to do that in our communities all the time to build each other up.  You know, but for the grace of God go all of us...your son or daughter could be the one needing encouragement from a stranger one day.   If we find ways to pay it forward - both small and large - then moving from ambition to meaning will become easier, and life can become sweeter for us all.