Life, Values & Legacy: Our Chat with Weston Zimmerman

We recently had the chance to connect with Weston Zimmerman and have shared our conversation below.

Good morning Weston, we’re so happy to have you here with us and we’d love to explore your story and how you think about life and legacy and so much more. So let’s start with a question we often ask: Have any recent moments made you laugh or feel proud?
Yes! The SynkedUP team just successfully solved a challenge we were having with time tracking in our product for landscape contractors. We launched a new version of our mobile app this summer, and we had a laundry list of challenges that we were betting that this new design would solve for us. A lot of work went into this project, with an entire team spending over a year on the research, design, and building of it.
One of those challenges we hoped to solve was to make it easier for the landscape crew in the field to allocate their time tracked across different sections of the job. We had found that a lot of our users weren’t even bothering to properly allocate their time across the different sections of the job because it was too difficult in the old app.
Soon after the launch, I was chatting with one of our customers who uses the app, and asked them whether they were tracking time and allocating it across different sections of the job. He responded saying that they were tracking time, but weren’t allocating it across the different sections of the job, as it was too time-consuming.
I showed him the new design, he was impressed, and told me they’d try it.
I just got a text from him last week, saying that their entire team is using the new design and loving it. It is so much simpler.
I love identifying a challenge in the real world and coming up with an elegant solution to it. The tricky part, though, is that coming up with the elegant solution is often the easier part. The hard part is coming up with the solution that the end user will actually use, without prompting, and love it.
Hearing that our customer’s entire team was doing exactly that made me proud.

Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Weston Zimmerman, and I’m from the beautiful rural Appalachian mountains in central PA. As a teenager, I started working for a local landscaping company called Tussey Landscaping, and loved it. I ended up working there for 15 years, and during that time I led large landscape construction projects, did the marketing and content creation for the company, ran the YouTube channel, and got involved in the business decisions at the leadership table.
One of the business problems we ran in to at Tussey Landscaping was pricing our jobs correctly and tracking each job to ensure it was profitable. We went to seminars, built spreadsheets, bought software, and still came up wanting. We weren’t able to find anything that helped us price and track a job from the time the lead came in, until the final invoice was sent.
My dad was involved in the tech industry, and through some network connections, got introduced to a software developer. The light bulb went on, and I was like “Let’s build our own product to solve this problem!”

I convinced the owners of Tussey Landscaping to give it a shot, and we started working on this project, collaborating with the software developer and the rest of the Tussey team to bring this vision to life.
I soon realised that the problem of knowing our own numbers, pricing and tracking jobs, was not a problem unique to us. This was an industry problem that all owner operator contractors struggled with.
A vision started to form of taking our little custom software project and turning it into a full-blown SaaS product for our industry. We called this product SynkedUP, and started selling it to our network contacts in the industry.
5 years ago I punched my last timesheet at Tussey Landscaping and went full-time on this new startup.
Today, SynkedUP is on a mission to end entrepreneurial poverty and help blue-collar contractors unlock prosperity by knowing their numbers. Practically speaking, this looks like calculating overhead recovery into their estimating, so they are pricing their jobs profitably, tracking their jobs, and making data-driven decisions in their business.
SynkedUP serves thousands of contractors in the landscape industry all across North America, and is helping many, many people finally price their jobs correctly and start producing real profits. The end result is owners beginning to feel like they own the business, instead of the business owning them.

Okay, so here’s a deep one: What’s a moment that really shaped how you see the world?
I grew up in PA, in a rural agricultural community. Hard work and pulling yourself up by your bootstraps were normal to me. In my world view, opportunity was around every corner. I was taught that you got out of life what you put into it.

When I was 21, I went on a voluntary service trip to Romania with a few young guys from my church to replace a school house roof. It was my first encounter outside of the US or Canada. I’ll never forget arriving in that sleepy little village tucked in the foothills of the Carpathian Mountains, and plunging into Romanian village life.

In that village, I met the girl that ended up becoming my wife. That relationship led to me living in Romania for the better part of 2 years while we were dating and getting married. Those 2 years in East Europe had a profound impact on me.

I had always heard how America was unique, special, and the land of opportunity. But I didn’t truly know what that meant or appreciate its signifigance until I spent those 2 years there, trying to do life. During my time there I built a small cabin for us to live in, dealt with local government to get all the paperwork and permits, dealt with the local work force and services, learned a new language, and observed a completely different culture.

I was in a country that was barely 20 years out of Communism. The mindset, culture, attitude toward work and the worldview toward government were fascinating and intriguing to me. Don’t get what I’m going to say next wrong. There are many incredible and hard working people in Romania. But largely, what I saw was a mindset of victimhood, an expectancy of the goverment to provide for them, and little appetite or desire to grow, improve, strive, and maximize potential. Instead it was a general lethargy of how little can I do and still survive. It showed up in the most mundane every day occurences like the person’s attitude at the grocery store check out, all the way to someone you hired to get some work done for you.

That experience changed me, and today it directly impacts the fire in my belly for this startup I am now growing, and the SynkedUP vision. When I came back to the US, and a few years later started SynkedUP, I saw an entire industry of really hard-working people who got up before sunrise, but still struggled to make ends meet. My personal mission is to make sure that these salt-of-the-earth people, who give you a firm handshake and look you in the eye, are successful. If anyone deserves to make it, it’s these people who aim to be a positive force in their community and are willing to work for it.

What fear has held you back the most in your life?
When I’ve had challenges in relationships, I didn’t face them early enough or often enough.
If there was a risk that the relationship could be damaged by raising the issue, I evaded it.
Looking back, when something wasn’t right, I waited way too long to bring it up.
I feared the tension and avoided the issue.
Especially when I struggled even to articulate what was bothering me.
I felt like if I couldn’t clearly articulate exactly what was bothering me and why, I hadn’t earned the right to raise the issue.
That has held me back and wasted so much time.
Trust your gut. If something feels off, there is a reason.
Today, I try to sit with the tension and rally the courage to raise it. If I can’t articulate why something feels off, I’ll start by just raising it with the other person and simply stating that something is off, and then we can explore it together, in the open, in partnership and collaboration.
My hesitancy has wasted so much energy and time.
Clarity and plowing forward, speaking the blunt truth regardless of the consequences, is powerful.

I think our readers would appreciate hearing more about your values and what you think matters in life and career, etc. So our next question is along those lines. What are the biggest lies your industry tells itself?
That hard work can solve anything. That you can outwork the problem.

The landscape industry is filled with skilled people who are not afraid of hard work. But they dread the practical tasks that come with running a business.
What I mean by that is they started the landscaping business because they love the work. They didn’t want to be stuck in an office job, looking at a screen or talking to an accountant.
The lie that so many owner operators tell themselves is that do good work, work hard, and everything else will take care of itself.
Not true.
If you’re selling your work priced at a loss, working harder will just increase the loss.
Eventually, every landscape business owner will arrive at the point where there are just no more hours in the day left. There’s not another task they can do, or another phone call they can answer. They’re tapped out.
And finally, everyone must learn the truth of that quote: work smarter, not harder.
Hard work alone won’t cut it.
It’s necessary, yes, but you can work your fingers to the bone and still lose.

Okay, we’ve made it essentially to the end. One last question before you go. What is the story you hope people tell about you when you’re gone?
That I worked to serve others, and I maximized the opportunities I was given.
My faith is important to me. I love the parable where Jesus talks about the talents, and describes the person who got 1 talent and buried it, and the other person who got 5 talents and invested them to grow 5 more.
The person who buried their talent had it taken away from them, and it was given to the person who now had 10 talents.
The lesson that the story teaches and inspires me with is that we are all blessed with something. Work with it. Grow it. Invest it. Don’t focus on how little you have. Focus on what could be.
I hope that my life’s work proves to be something larger than myself, and that the people around me are blessed by it.
I hope that the people we served at SynkedUP tell stories about how we had a positive impact in not only their businesses, but how that business impact led to personal impact in their lives and families – for the better.
I hope that the SynkedUP team tells stories that describe my heart for them and the work they did and were a part of. How they were proud to be a part of the SynkedUP mission.
I hope that my wife and children tell stories about how their husband and dad loved them and worked to prepare them for life.
I hope the parts of the world I encountered were left better because of my work.

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