Being Your Own Boss Is a Trap!

Will Kelly built a lawn-care company from solo operation to 20+ employees. He describes three growth stages: the Do phase under $250k where you handle everything, the Teach phase up to $1M where you train and hold people accountable, and the Lead phase above $1M where the business runs without you. The key is the 80% rule: delegate tasks once someone reaches 80% of your level, then coach them higher.
Chapters
Being your own boss is awesome in the beginning. You choose when you work, you choose which customers you take, you control your schedule. That's exactly what I wanted when I started my business. And for a while, that's exactly what I had. Then 3 years in came and the business I built to give me freedom Completely owned my life. I was mowing 5 days a week, sometimes almost 6 days a week during the summer. I'd mow all day, handle customer complaints, answer phones, respond to emails, and then come home and still have estimates to send and people to hire. I had built myself a job. And the problem wasn't that I didn't have enough customers. The problem was that that the business had grown faster than I had. Looking back, I believe there are 3 completely different stages you have to go through if you actually want to build a business that gives you freedom. And I'm talking about complete freedom. The first stage is what I call the do phase. For us, that was roughly from $0 to $250,000 in annual revenue. And in this phase, you should be doing almost everything. When we started, I mowed the lawns, I trimmed the bushes, I answered the calls, I handled the customer complaints, I sent the estimates, I maintained the equipment. I did the work. And there's nothing wrong with that. In fact, at that phase, that's what you should be doing if that's where you're at in the beginning. Doing the work gives you a ton of freedom. You can decide that you're going to mow this route on Tuesday instead of Monday. You can decide which jobs you want to take. You control almost everything, and it is amazing. The problem happens when the business grows, but you never graduate from being the person who does everything. That's exactly what happened to me. You see, we had more customers than I could handle, By myself, but I did not have enough dependable team members underneath me. At the time, I thought I had a labor problem. What I actually had was a leadership problem. I didn't know how to hire great people. I didn't know how to retain them. I didn't know how to hold people accountable. I didn't like confrontation. In fact, I still don't like confrontation even today. So I would let things slide. Someone would be late; I'd look the other way. Someone wouldn't meet the. Standard, I'd avoid having the difficult conversation. Then eventually someone wouldn't show up, and guess who went back out to mow their route? Me. I became the backup plan for every problem in the business. And if you are always the backup plan, you are not building a business that can run without you. You're building a business That depends on you. My biggest mistake during that stage was holding on to mowing for way too long. You see, mowing is one of the most basic things we do. It can be taught, it can be trained, it can be measured. But because I knew I could do it better, faster, and with more care than the new person, I kept taking it back and I kept doing it. That mindset will trap you forever. There's a concept that I learned that completely changed how I think about delegation. If somebody can do the job at 80% of the level I can do it, I need to seriously consider handing it off. That does not mean 80% becomes the standard. It means 80% is the starting point that gets me over the emotional hump of delegation because there is going to be a gap. They're going to make mistakes. And newsflash, so did you when you first started. Give them grace. They're going to miss things that you don't want to miss. That remaining 20% is what you want to coach. That's what I train. That's what I build a system around. Then I work to get them from 80% to 90% and then to 95%. And eventually the goal is to have them become better at the job than I ever was. Because you see, when you're a business owner, you wear all of these different hats. Imagine if you only, as a business owner, had to focus on one lane. Let's take mowing, for example. That's all you had to do 5 days a week, 8 hours a day is mowing. You would become the most efficient, profitable, dialed-in worker for your business if that's all you had to worry about. You didn't have to worry about emails, calls, complaints, buying the new equipment. Just you show up and you get dialed in and you work super hard in that one lane. You're going to be better than everybody else because you're going to have thousands of reps of doing the same task over and over and over again. And you have to believe that's possible. There are people out there who can do parts of the business better than you. If you don't believe that, you will never hand anything off. If I still believed every lawn had to be mowed exactly the way I would personally mow it, I would still be mowing lawns today. But then we wouldn't have 22 team members, we wouldn't have 3 locations, we wouldn't have a complete office support team on the back end, and I wouldn't have general managers leading their locations without me. And most importantly, I wouldn't have the opportunity to build and develop all of these people. Look, building this kind of business can feel lonely. That's why we built a private school community that is based off of a ton of other home service business owners that are literally going down the same pathway as you. We are winning together. You get all the tools, resources, and direct access to us. Join the movement today. The link's in the description below. That brings you into the second Stage. I call this the teach phase. For us, that was roughly about $300,000 to $1 million in annual revenue. This is where your job has to change. You stop trying to be the best technician in the company and you start becoming the teacher. You take everything that you know how to do and teach somebody else how to do it. Then you teach somebody else, then somebody else. You start multiplying and duplicating yourself through other people. You build training, you build checklists, you build accountability. You stop fixing every problem yourself and start teaching people how to solve problems. And this stage was extremely hard for me. It took me about 18 months to really grasp and understand how to lead and manage people, how to write somebody up. You see, I had never had a job where I was a manager of people. I did when I was in the military, but it was for a very short period of time, and I honestly didn't learn much from it. I didn't learn how to fire somebody when necessary, how to have uncomfortable conversations, how to care about people while still holding the standard. I used to think Caring about someone meant giving them another chance. And another chance. And another chance. What I learned is that leadership requires both. You can care deeply about someone and also tell them the truth. You can care about somebody and still hold them accountable for their actions. You can care about somebody and still decide they are not the right person for that position. That lesson allowed me to stop jumping back into every problem, but even teaching people to do the work isn't the final stage, because if every team member still needs you to lead them personally, you are still the bottleneck. The 3rd stage is the lead phase. For me, that really became obvious once we crossed the million-dollar mark. At this stage, you're not just duplicating your hands anymore, you're duplicating leadership. Today we can go through our busiest season without me running the day-to-day operation. We have more than 650 recurring weekly customers throughout the summer. The phones get answered without me. Customer complaints get handled without me. Emails and texts get answered without me. The mowing gets done. The spraying gets done. The landscaping gets done. Equipment maintenance, gets done. Team meetings happen. Our general managers lead their teams. The business basically operates without me doing the actual work. If you rewind 5 years ago, I was mowing every single lawn. I knew every single customer. That had to change. What I did in my job had to change. Now I am focused on things like vision, building leaders, building the leadership team around me, improving systems, implementing new technology and AI, thinking about where the company strategically needs to go next. And here is the part that took me the longest to understand: at every level of business, what got you to where you're at is the same thing that will hold you back from Unlocking that next stage. And you— ideally, I'm speaking to myself 5 years ago— am the bottleneck. If the business stops growing, one of the first places I need to look is in the mirror. What skill am I missing? What conversation am I avoiding? What am I still holding on to that I can hand off to 80% satisfactory? What do I need to learn? Who do I need to develop? At the beginning, my biggest problem was learning how to do the work. Then it became learning how to manage people. Then it became learning how to lead and develop leaders. And the higher you go, the more leadership becomes about who you are when nobody is watching. Your discipline, your quiet time, what you put into your body, how you take care of yourself, how you treat your family, how you manage Your emotions, how you steward what you've been given, because eventually the business starts reflecting the leader. When I started, freedom meant I could choose what time I wanted to mow a lawn. Today, freedom means hundreds of customers can be serviced and taken care of at the highest level. 22 people have great jobs. 3 locations can operate without me and the company doesn't need me touching every piece of the work and solving every problem. That's the difference between being your own boss and actually growing a business. Being your own boss is great and it can give you a lot of freedom, especially in the beginning. But if you never learn how to hand off the work, teach other people, and eventually build leaders, the business you started to create freedom from can become the thing that takes all of your freedom away. Guys, thank you so much for watching. Make sure you subscribe to the channel if you want to grow a more successful lawn and landscape business.










