High School Sweethearts Turned Business Partners: The Success Story of Urban Roots

rban Roots is a snow removal and landscaping company run by husband and wife duo, Jimmie and Tiffany Willams. Urban Roots has grown from having only two clients to serving the entire Western suburbs, and has been featured in the Chicago Sun Times, CBS News, and iHeart Media as a start up business to watch. Jimmie and Tiffany started the company out of necessity; as most companies refused to even consider Jimmie for jobs due to his criminal record. Urban Roots is now flourishing, and offers opportunities to others in need of a second chance. They are more than just lawn care; they seek to provide hope to struggling families looking for employment, and complete beautification projects at Chicago schools every Earth Day. Their mission is to show mercy and compassion to all people and support those in need. Tiffany and Jimmie recently completed ID’s Owner to CEO program, in hopes of furthering Urban Roots growth. They sat down with ID’s Katie Uram to talk about their experience, their journey with Urban Roots, and their advice for others looking to start up a business.  ‍

Katie: First off, can you tell me a little bit more about your company and what you do?

Tiffany: So we're Urban Roots. We started this business together, Jimmie and I, and incorporated in 2008. We started the business because Jimmie was having a hard time finding a job due to his background, his past. We purchased a pickup truck from one of my clients - I was a hairstylist at the time - and just decided to put a snow plow on the front. And within a month, we started doing snow removal. We started off calling our business “Just Us Lawn Care, Inc.” but after the snow removal season was over, we realized we didn't want to just remain a one dimensional company. So we branched off into lawn care and landscaping as well. Now, we provide snow removal, lawn maintenance, landscaping and parking lot maintenance.

Katie: So how did you end up choosing that focus?

Tiffany:  It was mainly because Jimmie was just having a hard time finding a job. One of my clients asked me if I knew anyone who wanted to purchase a pickup truck. That's when the idea of going into business for ourselves landed in our minds. So when we purchased the pickup truck, we weren't sure exactly what to do. At that time since Jimmie was a chef, we were thinking of purchasing a food truck or going into the restaurant business, but back then the barriers to entry in the restaurant industry were extremely high. But Jimmie had experience working snow removal and lawn maintenance, so we decided to put the plow on the truck and made some business cards and flyers. Jimmie and the kids went out on foot and passed them out, and we just started getting business. So we ended up just staying with landscaping.

It’s rewarding to be able to help put food on other people's tables by giving them a job, and being able to teach them skills that, you know, they can potentially take on for the rest of their life and either start their own business or help other businesses.”

Katie: So can you walk me through the steps you've taken in building up your business? How did you get to where you are today?

Tiffany: Oh, wow. I know one of the main things we did was just educating ourselves, attending as many courses and classes that we could, any programs that would be beneficial to the business. I graduated from National Lewis with my degree in business management in 2012. Before I went to National Louis, I was at Chicago State University and found out about a Small Business Development Center with an entrepreneurship class. That was the beginning for us, as they helped us identify resources that would help to build a business. They introduced us to ACCION Chicago, the Institute for Justice Law Clinic, SCORE and a number of different places we reached out to for help with the process of establishing our business. 

We got small business loans from ACCION, I want to say we received our first small business loan in 2009. We've received small micro loans from then on to help build working capital. 

We just continued to grow every year until 2016. There wasn't a lot of snow that season, and we were primarily a snow removal based business. In 2017, we received a Community Reinvestment Fund loan. With that, we were able to wrap the vehicles, repurchase tools and equipment, and redo the website. We also rebranded the business to move from more of the mom and pop feel to more of a corporate business, after which our revenue started to grow tremendously. We just did the JP Morgan Chase 2020 STAND program, and JP Morgan is currently working on bringing the New York Times out to do a documentary on us. Media coverage has definitely been important in growing our business as well.‍

Katie: What advice would you give to someone who wants to follow your path?

Jimmie: The advice we'd give is how important dedication and determination is for someone starting a business or coming up in the industry. Mainly because we had to be dedicated in order to help get this business to the next level. The determination was part of the resilience to keep pushing forward to the position we are in now. Also recognizing the importance of just trying to educate yourself as you start up, because without knowledge and a lot of different resources, it's almost impossible to get your business to the next level or to the point where you can grow upwards.

Tiffany: I would just add that newer entrepreneurs should be consistent with having meetings with their team and scheduling time to work on their business, instead of working on the floor of the business. I know we get tied up doing day to day activities, but to actually spend that time educating ourselves and learning more - about what Innovation Dupage is saying, you know - taking the steps to go from the owner to the CEO. Learning more about the strategic goals and directing the business, and being consistent about that.

Katie: What has surprised you about having this business or running a business?

Jimmie: One of the most surprising things, honestly, is the opportunity to help people. You know, with my background, being an ex felon, and being able to offer people jobs who would normally get passed over. All of these commercial contracts that we have, surprisingly, a lot of these properties that we service, I couldn't get a job at, or some of our employees wouldn't get hired at, because of, you know, some childhood mistakes that we made growing up.‍

Katie: That's really powerful, being able to then take it into your own hands then and do that work.

Tiffany: Yeah, thank you.

Katie: So what, if anything, would you have done differently? If you knew then what you know now?

Jimmie: What we would have done differently when we started this business 20 years ago, if we knew what we know now - because we've had a lot of ups and downs over the years - is just starting this business earlier to help us be in a better position than we are now.

Katie: So what are some of the most challenging aspects of running a business?

Jimmie: Well, the number one problem everyone is having, from Walmart to Home Depot, is hiring good, responsible and reliable help. Being in a position to hire a good manager, a good supervisor, so I can pretty much just walk away from the business on the ground and start concentrating on growing my business in other areas.

Tiffany: He still has to work in the field as an operations manager. So if we can find someone to add to the team that can take over the field operations, then Jimmy can better manage as a CEO.

Katie: What would you say is one of the most rewarding parts of running a business?

Jimmie: It’s rewarding to be able to help put food on other people's tables by giving them a job, and being able to teach them skills that they can potentially take on for the rest of their life and either start their own business or, you know, help other businesses.

Tiffany: Yeah and I would add that, it's been rewarding, working. We've just found it has been challenging, but in the end, it's just been rewarding. Because even at times where we were, not on the same page as a couple, we had to constantly make sure the business was being run well and work together regardless of whatever personal issues we have. Having to come together and focus on a business has been very helpful in our marriage as well. Jimmie brings strengths that I don’t have to the business and I bring strengths that he doesn't have to the business. So it's just been, it's been a great experience.

Katie: What would you say keeps you going when things get tough in your business?

Tiffany: Failure is not an option. Jimmy and I, we met when I was 16 years old and he was 18. So we kind of grew up together, you know?  I’ve known him more than half of my life, and it's the same for him. 

Jimmie: It can be a challenge, given the fact that, with the lawn care business, it doesn't snow every day, and then we work 30 days without getting paid. So over the years, we’ve had to try and create a structure for the business where we are not so dependent on those payments at the end of the month. Instead, we bill ahead to be able to keep up with our payroll, which is due every two weeks, and our monthly bill, which is due every 30 days.

The main thing that keeps us going is each other, you know, realizing that we have come so far from building a business and what we’ve gained through strength and experience.

Tiffany: And we have our family: our children, and our grandchild. We have a lot of people that look to us for hope. They look at us and say ‘if Jimmy and Tiffany can do that, then so can I.’ Just knowing that we do have people looking up to us has been a major factor as well.

Katie: Looking out three to five years, what do you think the next big change to your industry will be?

Tiffany: I know with COVID, businesses are taking a hit. But with our business, we work outdoors. The grass will continue to grow and winter snow is certain.

Jimmie: Well, the one thing about the landscape industry is that it’s constantly growing, because here in America we're constantly building. So there will always be work. Buildings and commercial properties are going up every day throughout the city of Chicago. So there will definitely be an increase in opportunities for us on all angles.

Tiffany: The landscaping for snow is always uncertain. We don't know, in some seasons, how much snow we’re going to get, sometimes it can be a little snow and in other seasons it can be a large amount. So it's always been wavy, which is why in 2016, we kind of switched up, because snow removal was the majority of our income. After that tough season, we focused more on lawn maintenance and landscaping to give us a little more certainty.

Katie: And then finally, can you tell me a little bit about your experience and the Owner to CEO program? What's the program been like? And, you know, what, what's been helpful?

Tiffany: It's very helpful, it's been awesome. We've learned a lot of different tools and information on a field level, that we hadn't even heard of. I like how the pace is, with the courses, and the topics are very needed for our industry. The last portion, which is project management and financing were both very, very helpful. 

We found out a lot of things that we aren't doing as a business that we should be doing, but then we also learned that we are on track for a lot of things, as far as where we are as a business. We believe that we will apply what we've learned from this program. This will help us tip over to that million dollar state that we've been yearning to get to.

Katie: How would you say the program compares to or, what's different about it, compared to some of the other programs you've done?

Jimmie:

Well, this program has really been in depth, and a lot of it is more hands on, a little bit more of a hands on experience, as well as being able to have those conversations and one on ones with those subject matter experts for each particular industry that we have been given, those are priceless opportunities that can help any small business.”

With resilience, compassion, and kindness, Jimmie and Tiffany Williams continue to work to make their dreams a reality, and better people’s lives, one day at a time. 

To find out more about Urban Roots and their story, go to their website. More of our Owner to CEO program participants will have a profile posted on the blog soon.