Matthew Underwood, Underwood Legal LLC

IB’s Professional of the Week is the premier way to meet Dane County’s professionals. This week features Matthew Underwood, owner/attorney, Underwood Legal LLC.

What are the most challenging and rewarding aspects of your job and why?

Being my own boss is probably the most challenging aspect of my job. It requires wearing multiple hats, from marketing and business development to drafting legal documents and providing legal services to clients. Having to balance legal and marketing functions can be challenging at times, but it’s very rewarding when everything comes together.

Who do you look up to or admire in business and why?

I admire Gordon Ramsay for his business skills and larger-than-life personality. It’s great that he could go from being a chef to becoming a successful entrepreneur, business owner, and TV personality. I like watching MasterChef Junior because it showcases his teaching abilities and I like that he is providing inspiration to the next generation.

What has been the high point of your career so far?

My career high point has been joining the board of the Ice Age Trail Alliance. I am passionate about hiking and the outdoors. My brother, David, and I were hoping to hike all 1,200 miles of the Ice Age Trail in Wisconsin, but he unfortunately passed away when he took his own life. After his passing, I held a fundraiser to raise awareness for suicide prevention and to educate people about how nature can help alleviate stress and anxiety. It has been wonderful to be able to honor my brother and serve the Alliance to further promote the trail.

Thinking back on your career, what advice would you give your 21-year-old self?

I would tell myself to have patience, keep moving forward, and to continue setting high goals. When I was in law school, there were reports saying it was the worst time to be an attorney and that the job outlook was miserable. Hearing other accounts of new attorneys having trouble in the job market was discouraging, but it also compelled me to do my best. Funny enough, I was cleaning out my old law school papers and found a list of goals I created while still in school. Even though my goals seemed lofty at the time, looking back now, I am proud to see that I’ve reached those goals.



What would you say are the best things about living and working in Dane County?

Dane County is a great place to live and work because we have a vibrant economy with a lot of talented people moving to the area. There are many opportunities to network with other professionals and business owners in the community. Moreover, it’s not just the urban centers; we have great hiking and biking trails, fishing, and boating opportunities.

Do you have any secret talents or abilities that people would be surprised to discover?

It’s not a talent but I love driving long distances. Road trips are a great way to see the change in scenery from farm fields to mountains and cityscapes. During my longest road trip, I drove 4,000 miles (over two weeks) from Wisconsin through Texas, New Mexico, Colorado, and back.

What are your guilty pleasures?

I’m a big fan of fried chicken — the crispier and spicier the better. One time in Nashville, I waited over an hour to get the famed Hattie B’s hot chicken. It’s definitely worth the drive. Wisconsin fish fries are also on the top of my list.

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