5 Entrepreneurs On Their Biggest Challenges and Turning Points

Entrepreneurial challenges and turning points

Entrepreneurship is tough. Full stop. But it’s so rewarding.

We asked 5 entrepreneurs across various industries to share the challenges and turning points that stand out to them as they look back on their winding entrepreneurial roads.

As Fred Hodge, owner of Clearview Washing put it: “At the end of the day, entrepreneurship is a roller coaster that we’re on. There’s so many highs, so many lows. It’s just nonstop, but at the end of the day, we just keep plugging along and fixing whatever is broken.”

The takeaway: If you feel like you’re banging your head against a wall, or facing yet another roadblock, you’re not alone! It’s part of the journey! And there are lots of positive turning points to look forward to, so read on!

This post is part of our #jobbersmallbizmonth series where we interviewed successful business owners and industry experts on the topics that matter most to entrepreneurs in the home services. Follow us on Facebook and Instagram to stay in the loop!

Dealing with entrepreneurial challenges

You can get stuck working in the business, not on the business

“Like everyone always talks about, you’re working in your business, not on your business. You kind of get sucked into that and you’re not looking at the company as a whole. You’re just worried about that day and that job. Once I was able to take that step back and I had the right people in place, employees, an operations manager, and the office staff [things got better].

Back in the day, I had to worry about not only making sure the jobs are all good, but I had a list of probably 10 phone calls I had to make when I got home at 7:00 PM. That was the last thing I wanted to do at that point. I wanted to eat, go to bed, and take a shower. I didn’t want to make 10, 15 phone calls. Once I was able to put the right people in place and work on my business instead of in my business, that was a win.” – Fred Hodge, Clearview Washing

Things break down, so be financially ready to fix them

“It was a big deal. It’s winter. As landlords, we now have to provide heat to our tenants or we can get them into a hotel room, so we scrambled and went to whatever store it was up there and had to buy all the heaters and stuff and get all that, but now we have to repair this huge, ginormous beast of a boiler. You’ve never seen a heating system like this before. It was like the entire size of the basement. It was monstrous. That’s scary, so it’s a big deal. It was hard.

You save your pennies for things that’s going to happen like that.

As you do this, you know things are going to break and you have to be prepared for that. Just because your bank account says you’re loaded or you have some dollars, you can’t spend that because you are anticipating and just waiting for things to break.” – Nancy Walker, Clarksville RV Park


I think we were really unprepared for growth as fast as we grew. You can grow too fast I think. Then Kristy and I really had to decide whether or not we wanted employees.

Brian Boase, MIL-SPEC Landscaping Quote

You can grow too fast, so you need to know what you really want

“I think we were really unprepared for growth as fast as we grew. You can grow too fast I think. Then Kristy and I really had to decide whether or not we wanted employees [Editor’s note: Brian and Kristy have decided to not hire employees]. I really enjoy my worker’s comp exemption.

I really think that the challenge is when we started really getting going, and then we’re picking up lawn care clients. We’re picking up more and more and more, and then you’re like, ‘Okay, cool, we can do X amount a day,’ just Kristy and I, and then it rains.

Then you get behind and then you try and play catch up. And then trying to make the transition from lawn care into strictly just landscaping, that’s a whole other conversation in itself.” – Brian Boase, MIL-SPEC Landscaping

Define roles for everyone (especially family!) early on

“As a family business, it’s easy for everybody to be involved in everything, and I don’t think it’s efficient or healthy. So we’ve really defined roles, and I think it’s de-stressed everyone. This is Christine’s lane, this is Freddy’s lane, and this is … We don’t all have to be involved in all the challenges. They built something huge before I even joined, but once I joined, the processes have been going very well.” – Christine Hodge, Clearview Washing

Put a value on your time, because you can’t get it back

“You need to put a value on your time. It depends on where you want to go with your business, too of course. There’s nothing wrong with being a one or two person operation doing the work yourself. It’s actually a lot of fun to get outside and do the work, and when we were busy I actually liked to go do the work as well, because it reminds the crew that you can do it as well and you’re not asking them to do anything you wouldn’t do yourself.

But put a value on your time. Is it more valuable of you to go do the work or is it valuable for you to go get more jobs? Or is it more valuable for you to figure out planning for the next year or month? Where are you going to create the biggest impact in your business: Is it doing the work or is it getting more work? Scheduling, maintenance—what is it? – Edward Ramsden, Jobber Product Marketer and Enviro Masters Lawn Care

Making it to a positive turning point

That feeling when the bank asks you if they can fund your project

“We’re not big ballers. We’ve been at this for a long time, so baby steps, lots and lots of little baby steps, but when you finally go to the bank and you’re like, ‘Hey, can I have this huge amount of money?’ and they’re like, ‘Sure, here you go,’ and then say, ‘By the way, do you have anything else coming up? We’d love to fund you,’ well, all right, that’s a big deal. They’re trusting in us. They believe in us. They’ve seen all the projects that we’ve done.

We are smart with our money. Our credit score is amazing, but things like that, everything they’re looking at, I think that was our aha moment of this is pretty sweet. This is nice.” – Nancy Walker, Clarksville RV Park

The first time you buy equipment on company credit

“We got a skid steer, and it’s the first piece of equipment that we didn’t have to bootstrap ourselves, and it’s the very first piece of equipment that we were able to get—mind you, it’s like 60 grand, and that’s like the cheap one I got—but it’s the very first piece of equipment that Cat Financial actually put in the business name, which is a big deal for us.

Everything, when we first started, everything: All those mowers, the trailer, we either paid cash for or it all just went under finance under our personal accounts, because the weird thing about a business loan is they won’t give you a business loan unless you have a ton of collateral and a business that’s already producing and profit and loss statements, so it’s very few and far between to get a, ‘hey, I’m new and I want to do this cool thing’ loan.

I took our 1099s from our Valvoline work [Editor’s note: this is a commercial client of Brian and Kristy’s], and then I used screenshots from Jobber. You know how you can go in and you can go and look at your cumulative growth and over the past 12 months? I took screenshots of all that, packaged it all together and I sent it to them. It sounds like a shameless plug for Jobber right now, but honestly, that’s how I did it.” – Brian Boase, MIL-SPEC Landscaping


I always tell everybody, ‘Trust the process.’ If you see something broken, whether it be joining Jobber, or anything ... If there's a process broken, let's create a process, trust it, and then, until it doesn't work, let's make it work.

Christine Hodge, Clearview Washing Quote

Seeing your new processes take hold

“My number one tip is trust the process. I always tell everybody, ‘Trust the process.’ If you see something broken, whether it be joining Jobber, or anything … If there’s a process broken, let’s create a process, trust it, and then, until it doesn’t work, let’s make it work. If it doesn’t work, we implement something else. This isn’t the end of the road here. Someone might be scared to join Jobber, but try it. Give it a shot. You’re going to love it. If you don’t, find something else, but you’re going to love it.” – Christine Hodge, Clearview Washing

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“Between the three departments, sales, office, and [field] employees, they almost all always fight back on everything. Then it’s funny. Six months later, after we’ve been doing it, pushing it, and pushing it, they say ‘It’s been great doing this.’ In my head, I’m like, ‘You’ve got to be kidding me right now!’ – Fred Hodge, Clearview Washing

Running out of space for all the supplies your growing business needs!

“You can’t afford to buy a bigger shop and sometimes there’s no point, so we actually bought pallet racking and put fertilizer on the pallet racking. That was a big turning point, like, ‘oh we actually need more storage.’ When you move into an empty shop it’s huge, and then all of a sudden it starts getting full. Then when it got totally full you’re like, ‘Oh this is an issue … I need to do something here!’” – Edward Ramsden, Jobber Product Marketer and Enviro Masters Lawn Care

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