Turning a Side-Gig into 20+ Years of Successful Business with Lisa Tadewaldt

Photo Credit: Jeffrey Moore

Lisa Tadewaldt is a certified arborist by the International Society of Arboriculture (ISA) and the co-founder of the regional tree services company, Urban Forest Pro. Based out of Portland, OR,  Urban Forest Pro has grown over the last 20+ years into one of the most respected, highly-rated, and credentialed tree services providers in the densely forested Pacific Northwest. Whether they’re safeguarding homes or businesses from potential wildfire threats or beautifying existing properties, Lisa and her teams of ISA-certified arborists spend their days up in the trees!   

Can you tell our readers about your background? 

I’ve always been a bit of a tomboy who was fiercely independent and curious, so that meant I spent a lot of my youth wandering around, entertaining myself, and piquing various interests or curiosities. I would commonly find myself feeling enamored when walking streets with mature tree canopies arching over the road, framing a home just perfectly, or providing a growing family with outdoor fun! I’d say this is when I developed a fondness for trees and welcoming outdoor spaces. However, as I began approaching young adulthood, I also wanted to provide for myself and accomplish some professional objectives. At the time I didn’t see a segue from one to the other, so I went to college in an unrelated sector of business and continued on that route until several years later when I decided to start my own business.

What inspired you to start your business? 

After college I began my professional career in public accounting, which is quite different (albeit a helpful skill set) compared to what I’m doing today. As a public accountant I had the opportunity to see the internal operations of so many businesses and really began to understand the financial factors that made some of them really successful and others in constant struggle. While I enjoyed my time advising entrepreneurs, I realized that I would prefer to be the entrepreneur vs advising the entrepreneur. I had already begun a side hustle/gig in arboriculture prior to my resignation from accounting, so when I decided to go out and start Urban Forest Pro, it made sense to try for that! If I’m being candid, I didn’t know it would develop into my career for the next 20 years, I just wanted to try it on my own. I had always loved the great outdoors, trees specifically, and had a fondness for landscaping and upkeep, so it seemed like a natural fit. Thankfully, it worked out, and we haven’t looked back since!

Where is your business based?  

We have been based in our hometown, Portland, Oregon, since our inception in the summer of 2000. We’ve moved locations once or twice locally, but have been firmly rooted in the community for a long time now. We serve homeowners and businesses throughout the region from Southern Washington state and throughout the greater Portland area.

How did you start your business? What were the first steps you took? 

Starting the business happened with a lot of luck and good timing. As I mentioned above, I was working in public accounting and had been approached by a peer who asked for some help and advice on a tree project. I shared my thoughts from years of interest in the field and self-taught knowledge and it resonated with them. I wasn’t certified at the time, as it was a hobby, but I took that one job simply to get some extra money. I’ll be really candid, I did not think of it as a path towards a full-fledged business, I thought of it as a gig. However, things slowly became more formal from there, and over time more jobs were booked, and the writing on the wall was telling us this had legs to become a bona fide business and brand. 

From there we just focused on our customer relationships for strong repeat business and referrals, established baseline performance expectations/standards for our work, and differentiated ourselves from the competition by becoming more formally educated than they were. We’ve certainly had our ups and downs, such as 2008 and COVID’s initial emergence, but we’ve always persevered by following our pillars of what “good business” means to us. 

What has been the most effective way of raising awareness for your business?

This is going to sound too simple, but you have to do good work consistently, as it is the only thing that works long term. Relying too heavily on a specific promotion, social media platform, or Google can deliver boosts or even sustainable results, but you’re only one algorithm update or change of policy away from losing your access to customer pipelines. While we certainly partake and engage with existing customers and prospective clients via all these platforms, it’s that word of mouth and referral network that can help you maintain your place among the community. Awareness through advertising and promotions can allow new customers to learn about you, but past customer satisfaction is what produces more warm handshakes and helps close new deals. 

What have been your biggest challenges and how did you overcome them?   

There have been a couple of things that tested us and I’ll mention them all.

First of all, being a woman-owner in a highly male-driven industry. Approximately 91% of arborists in the U.S. are male, so being a female is unique enough. Being a female owner and operator is even rarer. I’ve had the good fortune to have amazing crews who support our vision, far better than many, but I’ll admit I did cry on a job site here or there in my first few years. Even with my tomboy traits and enjoying male peers and activities, being surrounded by men and having some imposter-syndrome tendencies didn’t help me. However, their patience and support helped me to find my confidence as a leader, which was incredibly valuable. 

Secondly, the 2008 recession and the start of COVID-19 really impacted our ability to work. Both came out of “nowhere” and caught us by surprise. We, like lots of successful businesses, can weather a lot of storms, both financially and culturally. However, both of these presented new challenges that required us to dig deep into our reserves, get creative, and stay the course. Thankfully, we knew if we could only survive both scenarios, we’d prevail, as other vendors would fold (ie: close shop because they couldn’t weather the storm). It was less about making banner revenues vs sustaining for the time being so we could be one of the remaining options when the dust settled and commerce resumed. 

How do you stay focused? 

I choose one thing to focus on for various timeframes, such as today, this week, this month, and this year. So I’ll have one goal for 2022, one goal for January, one goal for this week, and one goal for today. Obviously, the weekly and daily goals update more frequently, but you get the idea. It’s about identifying what matters and prioritizing those goals. I then devote a predetermined amount of time to those goals and everything else just needs to get done (or not) in the time left over. Fortunately, this isn’t my first rodeo either, as I’ve had a lot of missteps over the past 20 years, so I’ve learned to delegate too. Delegation to trust team members is what can make an entrepreneurial journey a roller coaster or provide some sanity, so I recommend all business owners learn to give up some control of the reins.

How do you differentiate your business from the competition?   

Our biggest differentiator is that our team is composed of ISA-Certified Arborists by the International Society of Arboriculture. While other vendors may have one arborist on staff who’s ISA-certified, we strive to have every arborist certified. This does come with some challenges too, such as weekends spent learning/studying, staying up-to-date on best practices, and so forth, but it also shows our customer-base that we mean business and take arboriculture seriously. 

As an aside, we don’t advertise this, but I mentioned that having female arborists is rare. Well, we have several, and not only are they awesome at their trade, but they’re all ISA-Certified too! We like to lead by example and I believe that we’re doing a really good job at that!

What has been your most effective marketing strategy to grow your business? Remarketing our services to our favorite customers and referrals are huge! We also work with really savvy SEO and social media professionals to ensure our brand appears in front of those customers looking for our services. But as I mentioned earlier, we cannot get too comfortable with those channels as our sole means of acquiring new customers, as they’re largely outside of our control and can change quickly. Conversely, our quality of work, personal and professional character, and legacy reputation are significantly within our control, so that’s why we put so much effort into them!

What's your best piece of advice for aspiring and new entrepreneurs?   

Find a mentor, cultivate a strong relationship with them, and absorb their advice - preferably another woman leader. I leaned on several other women-owners during my time, in completely unrelated sectors to ours, solely for their guidance and anecdotes about their journey and how I could avoid the same mistakes. Some worked and others required me to learn the lesson on my own, but I’m certain it would have been a bumpier ride had I not asked them for advice. While not every mentor will be available to you or be available when you need it, some of them will and they’ll be eager to help you!

What's your favorite app, blog, or book? Why? 

I think everyone should read Shoe Dog by Phil Knight. He was the founder of Nike for those who are unfamiliar. There are a lot of business autobiographies out there, but most of them usually ooze narcissism by page 2. Unlike the herd, Phil’s book is something else, something unique, and I highly recommend it!

Unfortunately, I don’t have a lot of free time between running the company, studying new ISA/arboriculture topics, and spending time with family, so I don’t spend much of any available time on social media or using their apps.

What's your favorite business tool or resource? Why? 

Trello - if you are using post-it notes or a whiteboard you need to discover Trello now! It makes so much of managing the business easier and has all the technological benefits of modern apps and platforms. 

Who is your business role model? Why? 

I sometimes catch flak for this, but I’ve long admired Madonna and Samantha Jones (from Sex and the City) because they are who they are and they’re unapologetic about it. Clearly, Madonna is a real business and cultural figure, whereas Samantha Jones is a fictitious character, but I have channeled each of them for inspiration in different ways throughout the years. 

How do you balance work and life? 

I have a schedule and a routine but if I am not being productive, I take a break, which could mean lunch, it could mean leaving early, or it could mean going away for a long weekend. I’ve just learned that if I’m not being productive there’s no use fighting it and it’s better to get whatever restlessness I’m experiencing out of my system, so when I log back in, I’m refreshed and good to go!

What’s your favorite way to decompress? 

On the heels of the last question, I prefer to disconnect when I leave the office. When I’m at the office, my team requires me to be “on” and achieve the objectives for the day. Somedays, such as those restless days, I’ll have to throw in the towel, but they’re far and in-between. Because of that owner-mindset, when it’s time to decompress, I like to go somewhere for the weekend where there is no cell service! :) That way, I’m without the option to check in and really become absorbed in nature or my surroundings.

What do you have planned for the next six months? 

Thankfully, we emerged from COVID’s initial uncertainty in 2020 with strength and demand among the community. Unfortunately, the labor shortage that’s followed is real too! In light of the labor shortage, we’ve decided to leverage existing and new technology to get more done with fewer people. Technology can’t climb a tree and fall a limb away from a homeowner’s structure, but we can harness it to make our internal operations less people-heavy and more automated, such as scheduling, correspondence, and so forth. However, I want to make sure customer service doesn’t suffer along the way, so I plan to keep my eyes on it over the next quarter or two, to ensure that the stellar reputation we have doesn’t suffer. 

How can our readers connect with you?

Our website is the best way to reach us and learn about what we do. We really have put a lot of DIY educational elements, content, and time into it! You can visit that at UrbanForestProfessionals.com.