After the housing market crashed, isn’t the real American Dream starting your own business and working for yourself?

Unless you’ve opened a business before, it’s hard to know what to expect. It’s easy to be intoxicated by your own idea and plow ahead without adequate planning or research, to assume that hustle and gumption can overcome any obstacles.

For me, more than two years into helping launch a company for the first time, there are easily a dozen things I can point to that I wish we’d known at the outset, a couple mistakes so big that it’s hard to believe we survived making them. If someone had convinced us of a few basic things, it likely could’ve saved us a buttload of headaches and plenty of sleepless nights, not to mention a pile of cash.

Most entrepreneurial lessons you’ll likely need to learn on the go, as you sort out the minutia of what your business will do and how it will operate. You will make mistakes, and plenty of them.

But the insight afforded from experience is invaluable. These 10 Triad business owners — some full-timers and some side-hustlers working in a wide array of industries — as well as two start-up business advisors might be able to save you from making common and avoidable errors.


Tim Cox (pictured, top center): Stir Creative Group, (GSO)

“Everyone needs a name and logo for than the new thing they are doing. After 20-plus years of being a part of this process, I have actually contemplated writing a book titled something like, ‘The graphic designer already knows what your new business is doing wrong.’ As I think about writing this, it’s easy for the lessons learned to start sounding like a bunch of soundbites from business books. With that said, there’s really a lot of truth in some of the old standards. ‘Cash flow is king,’ — totally agree. ‘Under-promise, over-deliver,’ — gold. ‘Mind your knitting,’ —agreed.

“Find a mentor. Even if they don’t know they are one. To succeed, you need to get very good at your business and be good at business. These two things are worlds apart. Anyone can go into business, but not everyone can stay in business. If you don’t how much money you need to earn today, or this week, you need to find out now.

“Get some recommendations on a few good business books. They are boring as hell but I guarantee you’ll get something out of each. In general, they all espouse the same basic advice just in the clever wording of the day. The Power of Thinking Big, Good to Great, Lean In; it’s all applicable.

“Know what your strengths are, I mean really know. Knowing your strengths is [a] strength. Choose your business partners well. Know who your competitors are. Be better than them. If you don’t think you’re better than them, neither will anyone else. Where you are weak, outsource.”

Cox also offered advice specific to the design industry, but it’s easy to see lessons for independent contractors of various stripes.

“I work with clients and it’s important to do great work for them as a company and for the professional career of your contact,” he said. “The term ‘scope of work’ is the single most critical phrase in my industry. This stops projects from becoming never-ending rounds of revisions that never get produced.

“Find out what other people do in your industry, and keep finding out. Bill at certain progress-points. Let your client know in advance you are going to do this. It’s easy to start a small project that will ‘just bill when it wraps up’ and then the after an initial work phase and a couple of revisions the projects stagnates… for months. Then when you send an invoice you can often hear, ‘But we decided not to do that and we never took delivery of anything?’ Yeah… no.

“People always think they are in charge of the size of their company. In reality, the marketplace is the driver here. I see people put certain restrictions/expectations on their company’s growth and fail to adhere to obvious marketplace signals. People like this are often standing in the wrong spot at the wrong time.

“As part of the Google Partners program, we do a lot of online advertising campaigns. Many clients want us to have their ads show up when certain phrases are listed in search engines. We more often than not find out that what our client thinks people are searching for is not how people are finding them.

“Don’t show any ideas that you wouldn’t want to be chosen. They will pick that one, like, every time. Establish a real, bona-fide trusting relationship with two or three key vendors and give them your business. They will save your ass one day.”



The Honey Pot (via Instagram)


Beau Tate: the Honey Pot, Tate’s Craft Cocktails, (W-S)

“Ah, the long and distinctive list of mistakes and mishaps. Most entrepreneurs and especially [food and beverage] folk are prone to learning best practices through a series of thumps to the head that eventually strengthens the cranium to the point that you can head-butt nearly any obstacle out of your path.

“I helped open Tate’s [Craft Cocktails in downtown Winston-Salem] as a barback, worked a variety of openings in New York City, opened the Tate’s in Dallas —which we later sold off — as a manager, and helmed the Honey Pot’s opening as an owner. This gave me the opportunity to watch from a safe distance the first go-round and wade in a little bit with each opening. With all of that being said, I’ve certainly encountered more than my fair share of sticky situations that resulted from mediocre preparation or generally knuckleheaded thinking.

“I’m sure you’ve heard that gamut of ‘sound business advice’ including ‘plan for inspection delays,’ ‘over capitalize,’ ‘make sure you really get along with your partner,’ and ‘buckle up.’ These are all spot-on and essential to staying in business for longer than 12 months, but they don’t pay much regard to taking good care of yourself and your relationships. I’ve seen a lot of really talented and savvy folks burn themselves out because they discounted the need to maintain one’s humanity.

“I’ve fallen victim to this mental trap a few times before and it manifests itself in really funny ways — after enough time and distance. I remember being brutally tired and getting pitched a fastball by one of our first guests. I was so tired that I let my tongue slip and made a comment about being a capitalist outfit that was in the business of making money, and those words showed up in our first Yelp review, which I never let myself live down. I burned the candle a little bit too hard on that opening but walked away with a pretty good lesson — you can’t give it everything you’ve got if you don’t have anything left to give.

“Get some sleep!

“Other than that, I think I see a lot of folks get caught up in the romance of opening a small business [and] fail to plan strategically and attend to the basics of business administration [such as] finances, lease negotiation, HR, etcetera. There’s a reason almost all of the successful businesses in the world have either done these well or paid somebody to. They are essential. I don’t think that they detract from doing what you’re passionate about; if you dive headfirst into the challenge, I find that they’re actually really interesting facets of your core business that require a lot of skill and can be a fun diversion.

“Finally, mentor and invest in your staff. This is the only way to shift your life from being manageable to being pleasant. That and get out of the way once they’re better than you are.”


Screen Shot 2016-05-16 at 8.51.10 PMHillary Wilson Kimmel: PTB Farm, (outside GSO)

In its third year of business, Pine Trough Branch Farm is rebranding after missing Tim Cox’s first piece of advice about a name and a logo. It’s too complicated, co-owner Hillary Wilson Kimmel said, and now she and her husband are dubbing the operation PTB Farm for simplicity’s sake.

“I don’t feel like we have a strong brand identity, mainly our farm’s name,” Kimmel said. “It’s a mouthful, and then some people think PTB is a label like ‘grass-fed’ or some widely used thing. That’s been a struggle. Pick an easily explained name. Even long-time co-op members are not sure what PTB stands for or can’t remember it. Finding a name that stands out and sticks out in your brain is huge. The best part of a brand identity would be a strong name, which we don’t have.”

That’s true for any business, but Kimmel also offered tips for people who might want to start a farm or agricultural business.

“Only grow things that you love growing and eating. I think you’re going to care for things better if you love them. And you can actually sell them well that way, too. Have a real sense of how you’re going to sell it. That’s something that’s specifically a big thing within farming.

We lack a wholesale channel. I don’t really know how to talk to restaurants, even though I’m great at selling at the farmers market [in Greensboro]. But not enough people come to the farmers market to sell 100 heads of lettuce a day, or whatever the figure is. I think for small farms like this [one], being able to do the market and do the social media — I could go on and on about social media — but I think it’s great using those tools.”

Read more:


Right: Molly Grace


Molly Grace: Kleur lifestyle goods, (W-S)

“Learn everything about taxes beforehand! Everything. What taxes you pay, when they are due, how to file, where to file, and how to calculate what they are.

“Have a tight money system before you open. If you have more than one person involved, have clear duties for each and make sure you know all duties that need to get done. Break things down into yearly, monthly, weekly and daily ‘to do’ lists, and post them in a visible place. Make sure everyone is on the same page about them and that you check in on them daily or they’ll get away from you.

“Delineate days of the week for certain things, i.e. answering non-urgent emails, housekeeping, etcetera. Read correspondence carefully. Stick up for yourself, but take good advice from people who know better than you.

“Market, market, market, brand, brand, brand, and don’t ever stop! Momentum in marketing is the hardest thing to keep going.

“Finally, don’t overwork yourself and don’t think you can do everything you want when you want to. If you have others your working with, know your schedules — personal and professional — and work together to keep an open mind about what everyone is capable of. Recognize the skills you have and do not have, and take on what makes sense for those skills.”


Dan Besse: Lawyer, Winston-Salem city councilman, (W-S)

“I can tell you about my experience but it’s so atypical that it might not be the best example to use. Essentially, I’m an example of what you could call an accidental business owner. I have almost always worked for private nonprofits and originally it was in one or another staff role. Over the past few years, more and more of my time has gone into independent contracting work, that is, I’m not considered an employee of the groups I’m working for.

“That comes with good and bad news. As an independent contractor, you set your own schedule and you don’t answer to a boss on a minute-by-minute basis. You have a particular set of work chores you do and you negotiate what they are on an ongoing basis. The downside is, and this applies to whatever field it is… the downside is you don’t have the reliability of an employee’s paycheck. You don’t have employment benefits like health insurance coverage. That’s all stuff you have to arrange on your own. That part of what I do is fairly typical.

“The thing that’s unusual about what I do as a lawyer is that it’s not courtroom work and it’s not things like deeds or wills that are legal documents. I do policy research. I write up articles explaining issues, I advise clients on their own policy development that has to do with public issues like healthcare or environmental problems, and that’s an odd little niche to have.

“The things that might’ve been handy for me to know years and years ago are the degree to which personal relationships are the key to business. People hire you — whether it’s for an employed position or contract work — because they know you, they like you, they trust you. It’s not typically because of an ad or a résumé, it’s because of a personal connection.

“For those who are not natural extroverts, that’s a hard lesson to learn. I’ve learned how to deal with people over the course of half a lifetime, but it’s hard work for me. I’m not one of the folks for whom one-on-one conversation or interaction is energizing. For me and other introverts, it’s an energy-intensive process when I’m talking with people one-on-one or dealing with people in an unstructured social environment…. but it’s an absolutely central part of any business.

“It took me years to realize that. I was and remain a firm believer in doing things on the merits, selecting people — whether it’s candidates for office or businesses — on the merits of who has done the best work, who has worked the hardest, who’s the most capable. And it always bugs me when I see selections made on whose family are they part of, who’s their dad and what neighborhood do they live in, things like that. Reacting strongly in an adverse way to the conventions of social privilege predisposed me to undervalue the importance of earned relationship building. The personal relationships don’t have to be based on those unearned social perks. It’s actually more important when they’re based on the time and effort you put into learning what people need, what helps them, and what they’re looking for.”


Screen Shot 2016-05-17 at 10.56.49 AMNikki Miller-Ka: food blogger and private chef of Nik Snacks LLC, (W-S)

“The only thing I can think of is undervaluing my own work. When it’s time to talk money, as a freelancer, it can be scary. I’ve never been good at putting a dollar amount on my work and I practically gave away my food, time and expertise in the past.

Even if you’re starting out, don’t give it away for a can of beans. Make sure all of your partnerships are beneficial to all parties at every turn of the project. You might hear the line ‘This will give you and your business exposure,’ which is code for, ‘Will you do this for free?’

“Always remember: You can die from exposure. Exposure doesn’t pay the light bill. If you do decide to say no, another opportunity will come along. And if you do decide to not take monetary compensation, make sure it’s for something you want and not just because you’re excited to have been asked.”


Mallory Phelps: SweetFeathers Studio design company, (W-S)

“First and foremost, when making wedding invitations for someone who is essentially a stranger, it is imperative that they proofread carefully because I wouldn’t know spellings, pairings, titles. It was the last day before we could send the invites to the printer on time to meet our post deadline and I finally got an approval on the design. Excited, I sent the various components to the printer and thought nothing of it. They arrived, looked great, and I set to assembling all 125-plus of them.

“Once you stare at something for hours, you don’t see words. Just shapes and design components. After delivering the assembled invitations to my bride, her fiancé texted me that night with a very stern and upset message. We had [mis]printed ‘Son of of Mr….’ on the first thing that guests would see upon opening their invite.

“I immediately agreed to overnight replacements if they would just pay for the shipping. I ended up just eating the cost of everything — which was about $100 of material — because I felt so badly. Lesson learned was that, even though I love every client I’ve had, you have to assume that they don’t know anything and to double and triple check behind them despite getting an approval. I also learned that I needed to include a ‘proofreading’ clause in my contracts that states I’m not financially responsible for proofreading and spelling errors after they’ve approved.

“When I was very first starting, I would constantly offer discounts and free labor because I wasn’t confident in the fee I was charging despite the fact that it was still considerably lower than it should’ve been. I assembled one bride’s 150-plus invites with nine or 10 different components for free because she was my first client and I wanted to make a good impression. The assembly process probably took me about 20 hours in total and I charge $20 per hour now for assembly. I’ll let you do the math on how much money I lost out on.

“I also wish I knew that I didn’t need to try to force myself into a mold that wasn’t me. I can’t offer my clients a genuine experience if I’m not being my genuine self. Sappy sweet, blushing, uber-conservative vendors are a dime a dozen in the wedding industry nowadays. It’s my edge that sets me apart and I need to embrace it to carve out my niche in the business.”

Read more:


Watts Dixon: Revolution Cycles bike shop, (GSO)

“Revolution is my first business, and I definitely had some hard lessons early on. For one thing, I made it happen right when the recession hit. I’d been ready for lean times, but didn’t anticipate how lean it would get. And almost didn’t make it. Multiple times.

“One of the hardest lessons was trying to be everything for everyone. And that wasn’t where we [shined]. If anything, it diluted our real strengths. So when we started focusing on what we really liked and knew… and even presented ourselves in a more natural way, instead of a bland facade of ‘professionalism,’ things really started to stick.

“I’d say do not expect ‘If you build it, they will come.’ In this day and age, when you can literally buy anything online, just being a retail store doesn’t mean s***. You have to offer something singular. Something that brings people in, or at least sets you apart. And ‘great customer service’ often isn’t that. Because you know what? Every f***ing business in the world prides themselves on their ‘great customer service.’ So what are you, as a business, going to do that’s different?

“Beer taps were our way to really try to galvanize the social side of what we had going on. We’ve always thrived on that, and it was the logical step. We had to sit on the idea for years before making it happen, simply because of lack of capital and infrastructure. But once we moved, it was on. And it was our way to step out from a purely retail model.

It could have very easily been coffee, but we like beer more, and fostering a good relationship with the local shop across the street, [Spring Garden Bakery], seemed more legit that trying to steal their thunder.”


Megan Thompson: Wild Rituals Soap Company, (W-S)

“All in all, mistakes are really just how you’re looking at a situation. I try hard to keep a positive outlook and look at my business ‘mistakes’ as learning experiences. ‘Happy little accidents’ as Bob Ross would say.

“Wild Rituals is my first real business. When you’re an entrepreneur, you know it from a young age. So yeah, I tried a few small ventures before this that failed. In retrospect, I’m happy they did. When it’s right, it’s right. The important part is that you tried.

“To those looking to start an artisan business, I have primarily only encouraging words. One thing I can say is that you have to work hard. Don’t go into it to escape a 9 to 5. That 9 to 5 becomes a 24/7. It’s truly hard to put the work aside but you’ll learn how to when the time is right. My biggest mistake was not knowing how to set time aside for myself.”


Lee Mecum: former Art Pear Artist Services (W-S)

“I started and ran my own business, Art Pear Artist Services, for about five years and in that time I learned many things about myself and about others.

“You wear many hats when you own your own business. You are president, secretary, marketing department, finance department, artistic director, human resources, maintenance crew and all the worker bees.

“Consistent cash flow is a big challenge. It took me about three years to feel like I was making a regular — low — salary. You usually need more money than you think you need and always need more money than you have.

“Lots of people try to help you run your business. They say, ‘You know what you should do?’ a lot. Don’t let them get you off course. Stay true to your mission.

“One of the best things about owning your own business is being able to let go of clients who you don’t want to work with. The secret to that is leaving them with a good feeling for what you did do for them. Try not to burn any bridges.”


Sam Funchess: President of the Nussbaum Center for Entrepreneurship, (GSO)

Advising small businesses is Sam Funchess’ job. He’s helped wildly divergent companies, including this newspaper and the real-estate business down the hall at the Nussbaum Center get off the ground and then stay in the air.

“What we try to do is teach three skills. The first is learning how to make decisions. You hear that people run out of money, which is true, but a lot of the time it’s because they failed to make a decision in time before they ran out of money.

No. 2: Everything is about sales. Without sales, your business has no blood. Your blood has stopped. You’re living off the oxygen in your blood called your bank account.

The third skill is learning how to manage cash. That means understanding who needs to be paid and in what order before the business is shut down. You’re never going to have enough capital, and if you have too much you’ll spend money on stupid things. I’m not a big believer in ‘I needed more money.’ I think you needed more than that.

For me, that’s literally the first conversation, and every time we meet is trying to drill on primarily the decision-making because that’s usually the biggest mistakes. They don’t put the tourniquet on fast enough to stop the blood flow. Once they get decision-making, we have to focus on sales. Sales can cure a lot of problems.

You don’t know what you’re doing when you first start, so you’re going to make mistakes instinctively. That just happens and you learn over time.”

There are seven questions that Funchess will ask you if you approach him with a business idea: What do you want to accomplish, what do you want to be known for, what is your business, what is your product or service, who is your target customer, how do you market to this customer and show us that you can make money.

Most people haven’t defined any of these areas well enough when they think they’re ready to start a business, Funchess said. When asked about a target customer, people generally describe a slice of people demographically. He’ll tell them to give him “the names of 100 people who are going to pay you money, people you can call on.”

“Most people have not thought that deep into ‘who is the customer.’ They need to be thinking smaller. There’s an old saying that niches are riches. It’s cheaper and easier to focus on that target market and actually make money if you know that [niche].”


Noah Reynolds: Lecturer in entrepreneurship at UNCG’s Bryan School of Business (lives in W-S)

“I think the most important thing that [my students] learn is that they really have to do market research into the market and industry that they want to start their business in. They often change their business plan after they survey potential customers and compare their plan to competitors in the market.

“What I try to teach the students is that you have to have a specific niche market and how to position yourself relative to other competitors in market. To create new revenue where it wasn’t or to take away from competitors, they need to offer something that is unique or better.

“Find out what your brand is and how do you want to position yourself in the market. You really need to create a logo, an image or picture, and short name or slogan for the company that really tells the customer who you are and what you’re about. Oftentimes people want really long name or explanation, but you really only have four or five words. You really need to boil down who you are, or you just get passed by.

“Oftentimes new biz owners underestimate how much it’s going to cost and how much cash they’re going to need in the first few years. They often run out and then need to go find capital in a hurry.

“I’d want to know who’s involved in the venture team, the business team. Do you have a lawyer for organizing your business, or for intellectual property, a banker… who else is on the team, their partners, qualifications, do you have a business agreement? It’s about the relationships that they have in place. If they can answer those types of questions about the team they’ve formed around them, then I’d want to talk to them more about their ideas.

“I think the biggest problem people run into is that they do not think like the customer. They’ll have an idea and they think it’s great but they don’t go out and do a survey and ask the customers what they want. They think they have a great idea but may not ask many other people, and then they’re not going get the sales. I think that’s the mistake people make — they’re excited about their idea and don’t ask enough other people for feedback and criticism before launching.”

Join the First Amendment Society, a membership that goes directly to funding TCB‘s newsroom.

We believe that reporting can save the world.

The TCB First Amendment Society recognizes the vital role of a free, unfettered press with a bundling of local experiences designed to build community, and unique engagements with our newsroom that will help you understand, and shape, local journalism’s critical role in uplifting the people in our cities.

All revenue goes directly into the newsroom as reporters’ salaries and freelance commissions.

⚡ Join The Society ⚡