You’ve done more than start your business. You’ve taken your idea and built it from the ground up into a functioning, professional operation. First of all, congratulations! What you’ve done is a huge accomplishment. Second, are you thinking about the next step to transition your small or medium-sized business to a well-working engine that has the foundation to grow over time? If you’re not sure what that next step in your business growth strategy is, then this guide is for you.

Since 2006, we’ve worked with business owners as they’ve grown and scaled their businesses. They have a wealth of knowledge from do’s and don’ts to basic tips and tricks. We’ve collected those insights from business owners in industries from media production, to healthcare, to legal services, to education to bring you:

Growing up Your Business, a guide by business owners, for business owners.

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Are You Ready to Grow Your Business?

You likely started your business because you had a passion for providing a particular service, or because you wanted to be your own boss, or because you have a unique talent that you wanted to share with the world.

With that purpose, you took off into the world with your brand new website and business cards. Maybe you attended networking events and sent follow-up emails. Perhaps you enlisted the help of your friends or former colleagues to help get the word out. You might have even paid for some local advertising to get the ball rolling. If all went well, customers started to trickle in. Because of those efforts, today you are the owner of a real-life business. Now that you have reached this critical point, in order to sustain and create a successful business growth plan, it’s time to ask yourself the following questions:


When best friends, Emily Czerniakowski and Cassie Russo started a business together, they knew they wanted to run a dance studio, but they didn’t know exactly what they wanted their small business to look like as it grew. One decision they made, with scalability in mind, was what to name their business: CaRu Entertainment. This simple choice gave them lasting flexibility to expand the business in different directions, more so than if they had called their business “CaRu Dance Studio” or something similar.

Emily C., Owner CaRu Entertainment

“If you want to start a business, think about something that is scalable and don’t sell yourself short.”


Maury Rogow of RipMedia (video production services) and Megan Meconi of Cincinnati Spanish School and Academy knew that with more customers, more projects and more staff, everyday tasks that needed to be completed might end up taking more time than they should—a problem that can quickly get out of hand. To avoid this and manage business growth in a way that would keep the majority of their teams’ time going towards impactful activities, they took a look at their processes and determined what could be streamlined, delegated, automated, or outsourced.

Maury R. Owner, RipMedia

“Start to replace yourself; if someone can do 80% as well as I can—that’s the person I have to put in place. Hopefully, they can do 150% of what I can do, but at least 80% let’s me spend more time on selling the company and the company’s vision.”

Megan M. Co-Owner, Cincinnati Spanish School & Academy

“We have a system and a way to track people that are paying and can offer payment plans-that’s the kind of thing that makes a business run.”

Is my business name and intellectual property protected?

Michael Feigin of NY Patent Law works with many small business owners who learn too late how important it is to protect their products, their business name and other intellectual property. In most cases it will cost a lot less and be a lot more effective to protect your business early.

Michael F., Esq., Patent Attorney

“Get educated. Learn more about what goes into a patent or trademark and the process of getting one. Make sure you understand what needs to be protected.”

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How to Get and Keep Customers

As your business grows, there’s more work to do and more customers to serve. Meanwhile, all of those ‘marketing things’ you were doing in the beginning might start to fall off the priority list. New customers still find their way to you because you offer a great service and your customers are happy to recommend your services to others. But, it’s important to keep those acquisition and retention activities in place in your business growth strategy in order to grow in the long term. If you’re like many of the business owners we talk to, you might feel like you can’t afford to hire the staff you need to grow without a lot more customers coming in, but you also don’t have time to put into your marketing efforts to get those new customers-leaving you feeling stuck.

Here’s how to get unstuck. Ask yourself:


Rob Arneson is the program supervisor for a Haysville Recreation in a close-nit community in Kansas. Using the tools available, he put his efforts into focusing on his target customer. You can do this too by using insights from your database or other small business management systems to analyze your customer base and determine what makes a “great” customer for your business. Whether that’s someone that regularly purchases or regularly refers, use the data you have available to determine the customers that make the biggest difference to your bottom line.

Rob A. Program Supervisor, Haysville Recreation

“Find your customer base and really market to those people and then definitely give out evaluations at the end of a program to find out what they liked and didn’t like so you can keep them coming back.”


Lorey Choe, Strategic Growth Partner from The Draw Shop, an animation video production company, knows the importance of building and maintaining customer relationships. She suggests setting up a schedule to regularly check in with your customers. One way to apply this method to your business is to follow up right after your customer receives your services or as a promotional event or contest.

Lorey C., Strategic Growth Partner, The Draw Shop

It’s really about maintaining the relationships. So, you need to have something in place from the very beginning that gives you the ability to do that.”


Once you know your best customers better, use the commonalities between those people to define your “target customer.” When you have this profile defined, you can use it to determine how to best reach them (social media, email, direct mail, or all of the above). Lorey (The Draw Shop) and Rob (Haysville Recreation) have different marketing tactics they use to fit their respective, unique businesses. But, they both use tactics that engage the people that they’ve identified as their best customers.

Lorey C., Strategic Growth Partner, The Draw Shop

“We do a lot of special events and will make videos for conferences or some of the speakers and then people will say, “I saw your videos, that’s such a neat way to visualize what someone is saying.”

Rob A. Program Supervisor, Haysville Recreation

“We advertise [our classes] through the flyers we send to the school, our Facebook page, email and text messages.”

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How to Build Reliable Cash Flow

The ideal situation for many small business owners is to get their business to a place where it almost feels like it ‘runs itself’. What this really means for most is that the business is in a place where the steps needed to reach a certain goal can be easily identified and mapped out, creating a process that makes bigger growth goals achievable. Easy on paper: not easy in practice. It’s important to set the foundation for a business that can be both flexible and yet structured enough to scale and grow.

Four questions to ask yourself:


Seaver Chan, Owner of VanGuard College Prep, a college test prep tutoring business, knew that prioritizing cash flow management and spending the time and thought on cleaning up his business’ accounts receivable would pay off in the long run. And it did. It helped uncover ways to streamline day-to-day tasks, like accepting and reconciling payments.

Seaver C. Owner, VanGuard College Prep

“Starting out, we just accepted cash, checks and sent out invoices through email. I found that to be inefficient because most of the time if I wasn’t sending out an invoice, I was chasing down past-due invoices and our accounts receivable was growing like crazy.”


Josh Coffy of Flight Media, a digital marketing company, urges business owners to step back and look at their services from a passive income standpoint. Think: Do I offer services that could be packaged and sold on a recurring basis? If you do, develop these services into manageable packages that you can market and sell online. This will bring you one, huge step closer to cash flow security.

Josh C., Owner, Flight Media

“If the service can be completed without you, can be packaged and can be recurring, excellent. You’re on your way to passive income. If not, then consider dropping the service or putting more focus on the services that can.”


Emily thought a lot about how to improve her customer’s experience when buying tickets for their annual event. She thought about the steps a potential customer would have to go through, she wanted it to be as easy as possible for the customer to buy and as organized and manageable as possible for the business. For CaRu Entertainment, that meant taking their ticket sales online.

Emily C., Owner CaRu Entertainment

“That has just been a whole new ballgame for us. I set up tickets through [our Online Store]…Everyone got it and plugged in their information. We got lots of compliments about it.”

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How to Hire for Growth

You likely have an ideal culture in mind for your business, even if you only develop that idea when the need to hire arises. When it comes to hiring, most seasoned business owners will tell you: no matter what happens, don’t lose sight of hiring for the right fit. Skills and experience are great, but motivation is everything. A simple hiring best practice is to look for people with a can-do, always-learning attitude. The team you build will make the difference in the experience your customers have and the heights your business will be able to reach.


Company culture was important to RipMedia as they grew, so Maury made simple rules about who to hire and not hire, and stuck to them. Apply this to your small business by thinking about the company you want to build and what that looks like to choose people that will be the right fit for your vision.

Maury R. Owner, RipMedia

“You have to be a good person to work with us. This is the core of who we are. Your rules are up to you to create. What is something you do not want to compromise on? Make that part of your core beliefs and your values.”


As the Cincinnati Spanish School and Academy grew they needed to add employees to keep up with classes and the growth of their language programs. When it came time to add those new people, it was a big financial leap for the business – a leap that they attribute their continued success to today.

Megan M. Co-Owner, Cincinnati Spanish School & Academy

“Anytime you want to grow, your investment in the right people is going to cost you a lot more than you think in the beginning.”

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Get Help and Advice

Not many small businesses are successful because of just one person or one team. The leaders of the strongest, growing businesses seek out help from others, from customers to friends, to local resources. A new perspective can reveal an untapped opportunity for your business or insight into how much impact your business makes in the community. Look for opportunities to get feedback and tips from business owners with non-competitive, but similar models, and ideally that are larger or faster growing than yours. This feedback will help you gain self-awareness and inform how to grow your business in the future.


The Draw Shop decided to make customer input a key component to their growth strategy. They gave their customers a way to provide feedback easily and put a simple process in place within their team to follow up on this feedback, so that it became part of their business growth strategy to always be improving based on their customers’ needs.

Lorey C., Strategic Growth Partner, The Draw Shop

“We listen to customer feedback because we want to grow and improve so we hold ourselves accountable to listening and following up on that feedback.”


Dr. Pietrosanto started her practice with a passion, an education and experience in chiropractic wellness. However, she felt like she lacked passion and understanding on the business and financial side of things. As a result, she sought out tips for business owners and help from others to support the areas of her business where she needed help.

Dr. Pietrosanto, Owner Chiropractic & Wellness Hastings on Hudson

“Obtain advisers with different areas of expertise (finance, business, marketing, etc.). While I didn’t want to hear what anyone said about finances, overhead, and practice models, I had to listen and take advice or I would not have even gotten off the ground.”


In almost every case, when we speak with a business owner, at the point where they can look over their shoulder and remember that crazy climb into their now established business—there are things they wish they had done differently. They stumbled along the way and thought they were the only ones that fumbled through the process. They messed up and made mistakes…and felt foolish. The reality is that if you feel this way, if you mess up, if you feel foolish—you aren’t doing it wrong. You are learning and growing and the more you can forgive and trust yourself, the easier it will be to grow a business.

Emily C., Owner CaRu Entertainment

“Trust in the process and do what you know how to do and do it well. If you do this, the other things will tend to fall into place. There’s a lot you can’t control, so do what you can and then realize that the pieces will fall into place if you’re open to it.”

Megan M. Co-Owner, Cincinnati Spanish School & Academy

“I didn’t realize at the time, but you are everything. You are IT, marketing, payments, collections, accounts payable and receivable, web developer — you are everything. So know that sometimes you are just out there on your own, doing the best you can and you just have to make some mistakes, learn from the money you spend and move forward.”

Dr. Pietrosanto, Owner Chiropractic & Wellness Hastings on Hudson

“Recognize that it won’t always be easy! Owning a business is a struggle and can be downright exhausting! Prepare for the hard work and effort that you will need to put into your business.”

Wrap Up

We hope that hearing from other business owners about their journeys will help you on yours. Remember, you started and established your business, which is already a huge accomplishment and makes you uniquely qualified to grow your business into the smooth-running engine that will fuel you and your employees’ lives. Don’t let your business run your life. Despite the sheer anxiety and chaos you may feel at times, we hope these stories give perspective that it IS possible to set your business up in a way that’s sustainable and supports the way you want to live, however that looks for you.

Eric Remer, CEO PaySimple

“We will continue to make mistakes and continue to have our challenges, but we will always move the energy forward. The collective knowledge we gain through our growth and our struggles will continue to make us a better company.”

Learn how PaySimple can help take your business to the next level