A Simple Plan to Make a Million Dollars Selling Services


Listen On: iTunesSpotifyStitcher

Blog graphic.png

Is it possible to make 1 million dollars selling creative services online? Without crazy course launches or passive income being the main focus of your business?

We hear about this kind of income but mainly from online businesses that sell digital products, NOT creative services like design or photography.

So in this episode I chat with Kelsey Kerslake, the founder and creative director of branding agency Pinegate Road, and we chat ALLLLL about the business model that she discovered could get her agency to a million dollars just selling services.

And guess what? It’s pretty simple!

Click play on the player above to listen to this interview OR continue reading! And if you enjoy this episode, I’d love it if you’d share it on your Instagram stories and tag me @neshawoolery. I loooove hearing your thoughts on these episodes because it helps me know what kind of content you enjoy! Now, enjoy the interview.

Resources Mentioned

Kelsey’s Background

Nesha: How long have you had your branding business? Let's start with that.

Kelsey: Yeah. I actually started it as a lifestyle blog in 2011. I think that's when I kind of started talking to you way back in the day. I grew it to a studio, probably in like 2013 when it moved from just me sharing my day to day life and actually offering legitimate design services. Then I worked in corporate America as a stationary designer. Then I took it full time August, 2016, so it's been about two years that I've been running it full time.

Nesha: Oh wow. So, I bet that's flown by for you.

Kelsey: Totally. Yeah. So, when I was in corporate, I felt like things were fine. I was taking on work as a business owner on the side. As soon as I got a little too busy, because I had my full time salary to support me, it was like, okay, I'll just hire other people to help me out. It was not a big deal. I feel like I had… not systems, but I was able to just hand off some of the work very freely without worrying about the money. I think that's a big thing that people worry about sometimes when they get systems or people or a team in place, so it was easy for me to do then. 

Kelsey: I slowly got to the point where I could hire a virtual assistant, which was really hard at the time because I was a terrible manager. Sometimes it was like, how do I hand things off? I didn't really know how to. I felt like it was better just done by me because it would take more time for me to explain all the things and package things up to actually get it done for me. So, I was in that kind of mindset where I was almost just paying her to do barely any work, which wasn't her fault. It was all my fault from a managerial standpoint.

Kelsey: It came to this point last, I would say August of 2017, about one year into my business where I was just bleeding money for a lot of different things. I was like, okay, I'm working myself to death. I'm barely making money and I need a huge change here. That's when I kind of took a look at all of my systems. Unfortunately, I let my virtual assistant go because I just needed to have a fresh start at that point. No fault to her and she's amazing. I just re-took a look at how sales were coming in, how my systems and processes were and really built the foundation of my business from the ground up at that point.

Nesha: Yeah. I like that you made that point because I did the exact same thing when I hired, I think it was my second virtual assistant. With the first one I was really clear about the tasks that I needed her to do. Then when I stopped offering the service that she helped me with, we didn't work together anymore. Then I ended up hiring another VA. All of a sudden I didn't really have like a clear set of tasks that I needed had to take on. So, I was just paying her monthly fee for doing anything.

Kelsey: Yeah.

Hiring Her First Team Member

Nesha: I was like, okay, this needs to stop. I need to get myself organized and get my outsourcing organized. So, I totally know where you're coming from with this. You've hired a project manager, right?

Kelsey: Yes. So, that was actually the first person I hired when I kind of like revamped all of my systems. It was kind of interesting because my first inclination was like, okay, I have all this design work, let's go hire a designer to do that. In my mind, after I started thinking about that, what it would leave me with is all the project management. So, instead of actually doing my genius work, which is the designing and the strategy, I was going to be left emailing the client, working on schedules, sending proposals, doing the sales calls. Which part of that I still love, I love doing the sales calls. But I was like, that doesn't make sense. Why am I hiring somebody else to do my design work when the work that's actually taking up a lot of my time when I legitimately looked at it was all the project management. So, that was kind of a big aha moment as well. You think those emails and things don't add up. They really, really truly do.

Nesha: Oh they absolutely do. I love that you decided to outsource the things that you're not good at, the things that you don't enjoy doing and just stick to the thing that you do enjoy, which is designing. I know that there are people who are listening who maybe can't do that. So, you're going to have to organize your business yourself. If you can take on a team member who can organize your business for you so that you can stick in your zone of genius, like Kelsey. I think that's a really fantastic idea.

Kelsey: Yeah.

Hiring Subcontractors

Nesha: Do you have any other team members or is it just you and your project manager for now?

Kelsey: Yeah. I have my project manager who was my first hire. Then I think almost simultaneously I hired somebody to help with Showit. We work on a platform called Showit for our designs. I don't know if you know about it, but it's less development that's needed. It's more I design the website and my team member implements it on this platform. So, I hired somebody to do that because that was sometimes taking me 20/40 hours to do - to get a website just "developed" on that platform. That was other non genius work. The design was done, the strategy was done. So, I hired her to come on board with some of our web clients. Then actually just this week we hired two more designers.

Nesha: Wow.

Preparing Her Business For Maternity Leave

Kelsey: Yeah. Because your audience probably doesn't know I'm pregnant. So, I'm kind of like prepping, how do we make this work as I'm on maternity leave and still have clients coming in. I actually hired somebody who's going to be acting as the creative director. We have another person doing some of the more mid level design as well. Those are things I'm prepping now. So, when I go on maternity leave, the business will still run. We're building all the systems and processes in now and it'll all good.

Nesha: Yeah.

Kelsey: Yeah. Oh and I have a podcast editor too.

Nesha: You have so much going on. It's so great. I just love how organized you are. I love that you made the point of if you have systems and processes in place then when you do take time off, you're going to go on maternity leave. Obviously, you don't want to be working all that time. You want to spend that time with your new baby.

Kelsey: Yeah.

Nesha: So, it's important to have these systems in place so that when you do need to take time off from your business, your business still flows, it still works without you and it still brings in an income.

Kelsey: Absolutely. I think beyond just hiring a team, I also use digital systems. We have project management systems that keep everything organized. That saves my project managers so much time. We use things like Acuity Scheduling*. All the sales calls are coming in automatically getting populated to my Google calendar and there's no back and forth that we're doing. So, we're implementing a lot of these things that aren't team based that are actually helping with our entire productivity and saving a ton of time.

Nesha: Yeah. Absolutely. There are so many tools out there that can just automate things for you without you having to manually do them all the time.

Kelsey: Exactly.

Nesha: Like you were saying, Acuity Scheduling. It just saves all the hassle of going back and forth between you and your client trying to find a time that works ...

Kelsey: Yeah.

Nesha: ... for both of you for a consultation.

Kelsey: And tools as simple as Zoom that we're on. Just having a link to send somebody instead of saying, what's your Skype name? Can we log on and all of that. Having just a URL to send out saves so much time.

The Tools Kelsey Uses To Organize Her Business

Nesha: What tools did your project manager implement in your business? I know you mentioned Acuity Scheduling. Can you mention a few of the others as well so that people can kind of get a feel for how you organize your business?

Kelsey: We actually started in Google Docs, and I know that sounds a little crazy, but that was a great way for us to manually figure out what we needed as far as systems went. Then when we realized Google Docs was getting a little out of control as far as doing the schedules and things like that, we started using a project management tool.

Kelsey: I also live in Slack as far as communicating between teams. Then my project manager also implemented Dubsado* and then integrated it with Stripe so that all of our contracts are being sent out and all the payments are being made automatically. We actually get people's credit card information as part of their contract process thanks to Dubsado. We're never sending invoices and waiting for somebody to pay us. It just happens all automatically. So, that was something my project manager set up for us.

Copy of Templates_ Opt-In Button (2) (1).png

Nesha: Yeah. I use some of those tools as well. I love, love, love Dubsado. I'm a huge fan. For anyone who's listening who doesn't know, although I'm sure you've heard me mention it a million times. It's an all in one business management tool. So, you can send your contracts, invoices, questionnaires, you can send emails, you can just basically manage your entire client process from within Dubsado.

Kelsey: Yeah. Project management systems are everything because they just keep it all organized. You know when things are due. It's all done.

Nesha: Absolutely. What effect has all of this organization had on your business?

Kelsey: Yeah. This is the big drum roll, I guess.

Nesha: Exciting!

How Kelsey Tripled Her Income By Organizing & Outsourcing

Kelsey: From me managing everything on my own last year, compared to this year, I've tripled my income and my revenue. That's been incredible because you think like, oh, I'm going to hire this person and you just think of all of the money going out of your pocket. What you really have to think about is how much more client work you're able to take on. At one point this summer we realized we have 17 clients we're managing right now. It felt like, two. It just was moving so smoothly. People were handling what they needed to do. Our systems were in place. We were able to completely make tons more revenue, a lot more income for myself and pay my team what they really want to be paid. That's something we always talk about and have very open conversations about too. It was working for everybody. It was really cool to see.

Pinterest Quotes (1).png

Nesha: Oh wow. I love that you tripled your income even though you'd taken on team members, you've implemented systems and apps that obviously cost you money each month.

Kelsey: Yes.

Nesha: If you've done all of that and you're spending money on teams and tools, how has it helped you to increase your income? I'm assuming it's because you had more time to find clients, market and things like that?

Kelsey: Yes, AND we raised our prices a lot. That was a huge thing. I learned how to actually be a salesperson and in not a creepy way. I mean, our prices probably like quadrupled. I'm also able to spend time on Instagram stories every single day. I'm connecting with my audience. At this point, there's tons of marketing things I want to do. But I'm like, okay Kelsey, what is going to keep you the most sane? Right now, it's really just Instagram.

Then I go to quite a few live events too. I find a lot of people just from expanding my network, going to entrepreneurial events. That's been really huge for my business. Especially, as our prices increased beyond what people are comfortable spending just from a stranger on the Internet. They need to have that personal relationship with you before they're willing to step into that next space. So, that's been a really big thing for my business as well.

I've had the time and space. In August and September I took five trips! And my business didn't blow up. I had like nine working days. I was able to meet a lot of cool people and clients came up from that. So, having the team in place like allowed me that time and space to be able to travel. Yes, I guess it's the marketing efforts, but I just focus on those two strategies.

Nesha: You made such a good point. I think when you do invest in things like a team, you can see it as just money coming out of your business, but you have to actually view it from a different standpoint and say, “If I am going to be hiring team members or outsourcing, gonna be spending money on tools and apps that will help me organize my business, it's actually going to help bring in more revenue because it gives me more time to promote my services.”

I love as well that you made the point of raising your prices. I had this conversation actually with somebody that I'm mentoring and we were talking about raising prices: the effect of doing that without getting your business systems organized first.

I was telling her, you cannot raise your rates to what you want to want before making sure that your client process is really spotless. Because if you start charging people thousands more dollars, but you're giving them the same amateurish process they're just not going to be happy.

Kelsey’s Simple Plan To Make A Million Dollars Selling Creative Services

Kelsey: Yeah. Absolutely. I think just to go into a little bit of the fear of one raising prices and also hiring the team… I have certain processes and projects I like to be completely handled by a team. We kind of mapped out if we hired X amount of people, we got this many clients, I could easily make $1 million in my business providing services to people next year, selling what we're selling by just by being able to hire out all of those pieces and parts because we have our systems and processes in place as the foundation. So, that was really cool to see how easily that number can happen and it felt so out of reach before.

Nesha: That's a really great point because I think that a lot of us think that the only path to $1 million business if that's what you want is to create courses or go down the coaching route. Not everyone wants to do that.

Kelsey: Yeah. It's like, I'm not sure that I'll make $1 million next year, but it was cool to see that it could happen with the business model I'm building.

Hiring Friends & Family

Nesha: Back to your team… where did you find your project manager?

Kelsey: I hired my best friend. I went into this thinking like, oh, I can't hire my friends. They'll be tainted relationships or things will get weird. We just had really open, honest conversations about it. I was like, hey, I think I need a project manager. Is this something you'd be willing to learn with me? As a teacher she was very systems oriented because she had to be in her classroom. Then also being in the entrepreneur online space as a virtual assistant, she kind of got both worlds. I was like, do you want to make this happen? She was like, okay, we'll try this out. It's been wonderful.

I think asking friends, asking groups and being very specific about the type of person you need and the skillset that they need can be a great way to find other people. I think if you find other people who have project managers but they might not be in a space where they're hiring them full time, such as myself, they're not my full time employees. You can just say, hey, does your person have any availability? That’s a great way to find new team members.

Nesha: I think that you made a great point that you don't necessarily need to find someone who already knows how to do everything. Like you said, you said to her, if you can learn how to use Showit, then I'll hire you. I was quite similar with my best friend because I knew she was setting up her business. At first, it was going to be VA business. I was like, if you can learn how to use Teachable, which is the website that I use to host my course, Organize & Automate, then I'll hire you and she did.

I think that sometimes we can get a bit worried about finding someone who knows the exact tools and apps that we use in our business. You can also find people and train them how to use the things that you use in your business.

Kelsey: Yeah. One thing we've used on all of our hires is a personality test called Kolbe A. It does your like modus operandi or some weird Latin term. It assesses how you just naturally show up and solve problems in life and business. There's one category that shows how systems oriented you are. I was like, my person has to have a high systems number. So, I test everybody coming in to see if their natural state of being works for the job that we're going to have them do. That's been a really cool way to find people that might not necessarily know the skills but can be trained or learn the skills pretty easily because of their Kolbe score.

What would Kelsey’s life and business be like if she hadn’t organized her biz and built a team?

Nesha: Really great resource. Let's talk about if you hadn't done any of this. If you hadn't organized your business, taken on team members… what do you think your life and business would look like right now?

Kelsey: I'd be back in corporate America. I had that really bad August, and at the end I was like, okay, I'm either going to make it or find a day job. I was actually applying for jobs. I don't really share that.

Last Christmas I had a website launch and I basically did not have a holiday. I was in Florida with my in laws and every day for a couple of hours, instead of being with my family, I was trying to troubleshoot a website launch because that was all on me. I weirdly scheduled it over the holidays or it got extended. I vowed, I'm gonna have a holiday this year.

So, I'm taking off like a week for Thanksgiving and then three weeks for Christmas and New Year's. That's been in my schedule for an entire year. We just went over all the things at a team meeting and it's going to be handled. I barely have to do anything before the holidays. I decorated for Christmas. I'm having the best time. That was a huge. It's a tiny thing, but it was a big thing for me to be able to just have that time and space to be able to really celebrate my life, compared to last year.

Nesha: Yeah. I always say, if you find yourself working across holidays, then it's really time to do something about your business systems and processes. You should always be able to prioritize time with your family, time with your husband, your own peace of mind and your own joy and happiness.

Kelsey: Yeah. That was totally my life last year. It was awful.

Kelsey came off her depression + anxiety medicine…

Nesha: How did it feel when you finally got organized?

Kelsey: Oh my gosh, it feels so good. This is something I'm pretty open about. I was actually on anxiety and depression medicine. Because of the pregnancy I actually decided to go off of it or when we were trying to get pregnant. For a long time I was feeling so much anxiety still because that wasn't something that was managed by the medicine. Now, I've been medication free for over a year and I barely having anxiety. I haven't really changed anything other than the systems in my business. So, that is huge.

Nesha: Amazing! What do you have planned for this year? Obviously, you've got a new family member coming. What plans do you have for your life and your business?

Kelsey: I'm planning a four month maternity leave where I don't open my computer. So, we'll see how that goes. Business wise, we are launching an exciting new project in January, which will help people get really convertible websites that sell for them at a much lower price than formally custom thing, but still very much completely done for you. So I'm excited to launch that.

Then we have some amazing Pinterest management services that have been rocking people's businesses. I'm excited to just kind of up level that because that's something that is really impacting our business owners after they move on from our design services.

Nesha: I would like to wrap it up by asking you… what is your definition of success?

Kelsey: I think I'm pretty much living it being able to have the time and freedom in my life. Anxiety free to do what I choose every day, almost.

More From This Episode

Want to listen to this episode and hear even more insights on growing your income by hiring a team? Click play on the player below!

Listen On: iTunesSpotifyStitcher

Copy of Templates_ Opt-In Button (2) (1).png

Meet Today’s Guest

pinegate 0116 (1).jpg

“I’m Kelsey Kerslake, founder and creative director of Pinegate Road. I’ve been helping entrepreneurs and businesses build their brands and online presences for over a decade. I deeply believe that everyone has the potential to make their dreams reality and my agency helps people do just that. As your creative director, my job is to help take the vision in your head, ground it in strategy, illuminate it with design, and make it your digital reality.”

More From Nesha

Nesha-Woolery-Business-Mentor-Designers-Web-90 copy.jpg

When I’m not podcasting or helping my course students, you’ll find me sipping caramel lattes in Starbucks, binge-watching This Is Us or traveling the world with my backpack and my laptop! 

Looking for more ways I can help you? Here they are:

Organize & Automate - Use my premium course to organize your entire service-based business in just two weeks (on the side of your regular routine!) so you can stop stressing and fall back in love with your business.

1:1 Coaching: Podcasts can only help you so much. Sometimes you need to talk to a real human who isn’t as close to your business as you and can offer fresh insight on where you’re going wrong and what you need to do next. Click through to book a 90 minute power session with me. Get ready for a seriously big breakthrough, girl.

Subscribe & Leave A Review! 

If you enjoyed this episode, you can show your support by leaving a review, subscribing, or sharing your biggest takeaways on your Instagram story! Just remember to tag me @neshawoolery so I can see it.

Here’s how to subscribe and review the show:

  1. Subscribe on your favourite podcast platform: iTunes, Spotify, Stitcher.

  2. Click here to open this show in iTunes and leave a review. 

Listen On: iTunesSpotifyStitcher


Nesha Woolery

I build beautiful brands & websites for passionate entrepreneurs!