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As a basketball player for the University of Wisconsin in the late 1980s, Trent Jackson was in on the beginning of the transformation from Big Ten doormat to Final Four contender. Following a basketball career in Europe, he served as CEO of the Boys and Girls Club and later founded the ROUGH Foundation and ROUGH Sportswear to help athletes and other youth through their journeys, no matter how rough.

Rank your top five MCs. (5.) Cool Moe D, (4.) LL Cool J, (3.) KRS-1, (2.) Big Daddy Kane, and (1.) Rakim

Which motivates you more: doubters or supporters? Doubters for sure. My motto has long been to “don’t talk, do.” When I entered high school people said that there was no way that a freshmen could play on the varsity basketball team. I enjoyed showing them that I could and was voted First-Team All-Conference and led the conference in scoring as a freshman.

When I came to UW-Madison, people said that majoring in Economics and taking business courses was going to be too hard for me. I have a degree in Applied Economics and my MBA from UW-Madison.

When I was starting ROUGH Sportswear, people said that the sportswear industry is very competitive and how can you compete with Nike, Adidas, Under Armour, etc. Adidas has made two offers to buy ROUGH during the last 20 months; I rejected both offers.

What does it mean to be black in Madison? Personally, it means that I have a responsibility to help those that are less fortunate through whatever means and advantages I am afforded. And, it means that I have to lead by example, not just for young black men but for all shades of young men, of being a good husband, father, son, brother, neighbor, and citizen of Madison.

What three leaders in Madison under 50 have impressed you the most? Michael Johnson, CEO (Boys & Girls Club); I am impressed with how he makes what is a very challenging job look so easy. I helped bring the Boys & Girls Club to Madison in 1998 and was the CEO from 1999 to 2001. I understand the commitment it takes to manage the operations and at the same time fundraise for the organization. Michael does it effortlessly.

Greg Gard, Head Coach (UW Men’s Basketball); I admire his calm style of coaching and his leadership quality with young men. I am very impressed with how he has assumed the lead role for the UW men’s basketball team and turned around a season that was headed in the wrong direction. He epitomizes the “don’t talk, do” motto I try to live my life by in that he has made no excuses and is letting his coaching ability speak for itself.

Alisa Robertson, Chief Development Officer (UW Foundation); I work with Alisa at the Wisconsin Foundation & Alumni Association and am very impressed with her leadership skills as the University of Wisconsin-Madison embarks upon a $3.3 billion, five-year campaign. I am amazed at how she keeps it all organized and straight as there are so many moving parts and she always seems to be having fun.   

What’s the biggest stumbling block in Madison to turning the corner on our racial disparities? The biggest challenge as I see to turning the corner on Madison’s racial disparities is within the church community. I believe that a community the size of Madison could quickly turn the corner on racial disparities if the church community would take the leading role. The main issue to address would be to encourage interracial church services at least among like-religioned churches. Wouldn’t this be what Jesus would want us to do?   

What are your top three priorities at this point in your life? My faith is obviously number one along with my health because if I am not grounded by my faith and living a healthy lifestyle how can I be prepared for my next two priorities. My second priority is my wife Cathy and two children Talia (14) and Armani (12). They are my world! And, my third priority is ROUGH Sportswear.

If you have to pick from the all-time men’s Badgers basketball teams, who would be your starting five and who would be your sixth man off the bench? Frank Kaminsky (center), Danny Jones (power forward), Michael Finley (small forward), Ricky Olson (two guard), Devin Harris (point guard) and Me (sixth man). I could be a starter on this team but I would choose to come off the bench.

What made you start the ROUGH sportswear? ROUGH Sportswear was started to help fund the ROUGH Foundation, which mission is to Reach Out U Give Help and Reach Out U Get Help. I have always thought that the word “rough” embodied my life as I grew up in a rough neighborhood in Chicago and made it out with the help of a lot of people (Reach Out U Get Help). In addition, to me, the word Rough makes a statement about how things can be in life and how you respond to difficult challenges you encounter in life. I felt like I was a rough draft of a person as a kid, had a rough road to travel to success, and now I have to be rough to help others (Reach Out U Give Help). There is so much more I want to say here but you will have to wait to read the book A ROUGH Journey, which is about my life and the making of the ROUGH Sportswear company.   

When you were the CEO of the Dane County Boys & Girls club what are the three things you learned to run a successful non-profit organization? 1. The power of preparation and being organized (keeping lists), 2. Doing as opposed to talking, and 3. Patience    

How did basketball prepare you to have your own business? I learned from playing a team sports like basketball that you are only as good as the people you surround yourself with and that you can’t do it alone. To be successful in sports it takes planning and preparation and having teammates execute and play all sorts of roles. It is the same principle at work in business; you must plan, prepare, and execute the business game plan with several people playing vital roles.

Reggie Miller vs. Stephen Curry: who is the better 3-point shooter? Stephen Curry! I have never seen this type of shooting expedition sustained for this long. Sure, great shooters get in the zone, I have been in the zone myself a few times where the basket seems to be an ocean and you throw up shots that somehow goes in. But, I have never seen a shooter that doesn’t have a slump at some point. What Curry is doing; I would not believe it if I wasn’t seeing it for myself.  

Where is your favorite place to vacation and why? Los Angeles each month to visit my children. When they are not with me during the summer and holiday breaks, I visit them there. Armani is on Grey’s Anatomy and have been in recent major movies such as Cooties (with Elijah Wood) and The Last Witch Hunter (with Vin Diesel) and Talia has been in the movie A Green Story and is featured in an upcoming Wendy’s restaurant national television commercial.  

 

Written by Henry Sanders

Henry Sanders

Henry Sanders is Publisher and CEO of Madison365.

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