Nathan Harris

Meet Milwaukee Millennial Nathan Harris, Owner of Ugly’s and Ease

Nathan is the owner of the popular Ugly’s Pub, a bar and grill that turns into a jam-packed lounge come nighttime complete with live music. He also founded Ease, a company which connects businesses with talented freelancers worldwide.

Nathan Harris endured periods of homelessness as a child and came out on the other side a successful business owner and consultant. Now owner of Ugly’s Pub at 1125 N Old World 3rd St. and software company Ease, all by the age of 27, Nathan Harris is a Millennial success story in Milwaukee. We sat down with the hardworking dynamo to learn more about his story.

You’re the co-owner of Ugly’s – how did that get started?

I like to think every experience happens for a reason. I had just taken the deep dive into pursing my own dreams – dropping out of college and leaving my corporate job at the same time. I was ready to build a name for myself and act as a management consultant for small businesses; I went after a number of local companies and began contracting for them. During this time I was approached with a full-time position as the Director of Marketing for Ugly’s. Though the opportunity was great, I knew I wanted something more, so we agreed on a plan that would make me an owner one day. Throughout the development of Ugly’s, we faced many challenges that forced me to step up beyond what I had ever anticipated. Shortly after opening I left the company but was asked to come back within less than 3 months. 

Ugly's Pub interior shot
Photo by Jeremy Baccash

Being asked to run the business on my own has been the greatest learning experience of my professional career. Once I came back, I completely rebranded the business. We changed the brand identity, came up with new marketing, new partnerships, and a staff that would help pave the way for our success. Within less than six months, I was able to double the business’s sales, and by the end of the year sales were up by over 300 percent. This proved to my now-business partner Rob that I had what it took, and that I was committed to the success of every client I take on. Now, almost four years later, I am a proud owner of the business, working to continue the growth of Ugly’s and build a staple that will be part of the Milwaukee culture forever. 

What inspired you to get involved in the Milwaukee nightlife scene?

I was inspired to get involved in Milwaukee nightlife because it teaches you so much about people. You are pushed in just one night to interact with hundreds of people with only a matter of minutes to make a lasting impression on them. This requires not only to have great attention to detail, but also a passion for putting smiles on people’s faces. It’s such a beautiful thing to watch the guest experience transform from casual dining during the day to high-energy nightlife on the weekend, allowing people to escape from all of the stressors of the week before.

What are your favorite Milwaukee hotspots?

This is a hard question to answer since Milwaukee thrives on offering so many great experiences. For places outside of my own establishment, which just feels like home to me, I would recommend the following:

If you are talking about a great place for an approachable, cozy dinner date, I would go to Braise.

If you ask me where I would like to go for the best lounge experience, I would say Plum Lounge. I have a great level of respect for people like Mazen and JC Cunningham. They take pride in customer value and show it in their work.

Now, if you are talking about the hottest DJ lineups from all over the world, then you have to mention Site1A. I have known Chris Vrakas for a long time and his drive is unprecedented. It shows in both his music and the experience he creates within his establishment.

Lastly, I can’t forget to mention my good friend Ben at Pourman’s on Water, a Milwaukee hidden gem that makes you feel welcome.  

Ugly's Pub exterior shot
Photo by Jeremy Baccash
Where does your inspiration come from?

My inspiration comes from the most amazing person this world has ever known. That person is my beautiful, kind and selfless mother, who has always been there for me. She worked tirelessly as a single mother to provide for my brother and me, and it just wasn’t easy: Fighting through sleepless nights as she watched her kids crying themselves to sleep because we had no food or lights at night; eating sugar rice and kidney beans because that’s all the food pantries had left; singing songs as we walked for miles in the snow so we wouldn’t notice the cold soaking through our soles. Not allowing these things to break our souls is what really mattered.

My mother showed me how no matter what, you can survive and overcome any obstacle. It could be a professional, mental, or a physical challenge. There is nothing you can’t beat if you just believe in yourself. I apply those same principles in my professional career and there is no challenge it can present I can’t beat. The pain of growing your mind will never be as bad as the pain of hunger or fear of losing your mother and brother. 

My brother is also a great motivation for me and has always been like a father to me. He has taught me that the value of your life is not measured by what you can do for yourself, but by what you can do for others. I will always stay true to those values and do the best I can to help others in achieving their potential. This is why I got into management consulting and have such a desire to help others grow.

You also started a company called Ease. What’s that about?

Ease focuses on giving companies access to the best remote freelancers in America regardless of your geographic area by providing you with remote workers via our Freelance Management System. I realized, living in Milwaukee, that many areas struggle to find the software development or digital freelance talent they are looking for, largely because the areas that many reside in have a greater focus on manufacturing or agriculture and are suffering from a level of Digital Darwinism. We solve that problem for companies by pre-screening talent and matching them with companies that need their services, providing people with the best talent for up to 30 percent less than if they hired them full time. This gives companies the visibility, variability and velocity they need to scale, as well as giving freelancers the autonomy to live the life they want by working remotely from wherever they choose.

Would you encourage Millennials to stick around Milwaukee?

I would most definitely encourage Millennials to stick around Milwaukee. It is running under the radar as one of the fastest growing cities. Right now the people of Milwaukee have the opportunity to mold it; to create a new identity for our city that will dictate the experience people have for many years to come. Our city is in a rebuilding stage and it’s one for the better. I can’t imagine why someone wouldn’t want to be a part of that!

What’s a typical day in your life like?

Every day in my life is like being on the last lap of the Indy 500. Though it can be stressful moving at 200 mph, you have to find a way to slow things down in your mind. I do that by creating a routine that promotes creativity, growth and wellness, while also finding the time to spend with my loved ones.

I wake up at roughly 6 a.m. everyday and I immediately begin to play inspirational content – content from people such as Les Brown, Tony Robbins, Eric Thomas and many more. This puts me into a mindset that prepares me for whatever I am going to face that day. 

Once I am done getting ready, I spend one hour researching a specific topic of interest to me. I then spend the rest of my time until roughly 8 a.m. meditating and finding ways to activate my creative spirit.

When 8 a.m. hits, my phone begins to ring and the emails begin to roll in. This lets me know that it’s time to get the day rolling. I follow my daily plan as closely as possible and focus on not allowing anything to deviate me from it – juggling tasks between clients, Ugly’s, Ease and a number of groups that I am involved in. The challenge is great, but it is doable if you create a system.

By around 4 p.m., I take a breather and go to the gym. Fitness is very important to me because I believe your mind and body must remain in sync. If you do not focus on your wellness, you will not be able to maintain the output required to achieve your goals.

Once I am done working out I try to spend time with my family and usually will try to fit some form of activity in. When I’m done with that, most of the time I will work again once I am home if my tasks for the day are not done or something comes up. Then before I go to bed, I map out the plan for the next day and do it all over again.

What do you love most about Milwaukee?

Milwaukee has a culture that cannot be matched. It is unique in so many ways and the “smallwaukee” culture allows people to have greater access to the movers and shakers of our city. It’s almost the epitome of the American dream if you think about it. You can achieve any level of success if you are willing to work for it. Many people believe that only exists in the larger metro areas, but I disagree. Those areas offer opportunity but also present greater barriers of entry. In Milwaukee, anyone can make it to the top. I feel that I’m living proof of that based on where I have come from. Though I am not at the top, I can see myself achieving so much more. I left my job at 22 and am now 27 and have learned so much in those five years.

Where do you see your future taking you in the next five years?

In the next five years I hope to be speaking to rooms full of people about how they can achieve their dreams, while also creating a free online school that provides people with all of the resources they need to become an entrepreneur. We go through everything we do so that we can make it easier for those who come next. I believe people forget that at times and fail to give back. I will devote my life to providing opportunities for those who want to make the world a better place. They just need someone to show them how.

Favorite life quotes?

“There are 86,400 seconds in a day! And how you use those are critical …and what you do today is going to cement who you are!” – Eric Thomas

“Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma – which is living with the results of other people’s thinking. Don’t let the noise of other’s opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.” – Steve Jobs

[Editor’s Note: This story spotlighting Nathan Harris’ role in the growth of Ugly’s Pub has attracted questions from some readers who have presented the magazine with allegations of unpaid bills to contractors, including Novo MKE and ADM Contracting. The magazine takes the claims seriously but has so far been unable to verify the allegations through official records, such as court documents. Harris issued a statement in response, saying that as a “partial owner” his responsibilities don’t include “the financial side” of the business, elaborating that “none of those business deals have anything to do with me.” The magazine will continue to look into the allegations against Harris and Ugly’s and add relevant information as warranted. Anyone with more to say on the topic should write us at]   



Paige Weslaski is a freelance contributor to Milwaukee Magazine. Having lived in New York, Los Angeles, Europe and Central America, Paige returned to where her heart was all along - her hometown of Milwaukee. Paige is the founder of the online Milk & Honey Magazine and the host of WTMJ's Milk & Honey podcast.