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How to Know When to Hire Your First Employee



How to Know When to Hire Your First Employee

Opinions expressed by Entrepreneur contributors are their own.

At some point as an entrepreneur, you’ll face a challenging decision: When is it time to hire your first employee? After incubating the idea of your startup. then deploying your resources and making it all happen, at some point you may realize it’s time to bring someone else in to help you achieve your vision and grow the business. It’s exciting, but at the same time, can be daunting. What if the new hire doesn’t work out? What if you hire too many people or too few?

Entrepreneurs are inherently self-starters and ambitious, and shifting responsibilities to new workers can be difficult – but it’s a necessary step for growth. A company needs support to grow and thrive. You can’t do it all on your own, which makes hiring employees — especially the early ones — a crucial step toward entrepreneurial success. Before you do anything, though, ask yourself: Is this the right time to hire?

Knowing when you shouldn’t hire

Before addressing best practices for hiring, it’s vital to recognize common pitfalls entrepreneurs face when starting to grow their workforce – that starts with knowing when not to hire. Similar to making big life decisions, you should avoid hiring employees out of anxiety or uncertainty. Your choices should be deliberate and strategic. Take a step back and reconsider hiring employees if you find yourself in the following situations:

You’re desperate

If you have more work than you can humanly handle and you just need to get another body behind a desk, it’s tempting to find someone right away. However, a hasty decision born of desperation is rarely a good one. Take the time to find the right person for the job.

You don’t have specific responsibilities for an employee

Unless you have a defined set of tasks and expectations for your new hire, do them a favor and don’t hire anyone. A new hire at this stage will rightfully be confused and ineffective. You may need help, but if you don’t know exactly what that help will look like, consider hiring a coach instead of an employee.

You’ll take anyone

If you’re lucky, the first applicant will be an absolute rockstar who can bring your business to the next level – but that’s not the norm. You’ll learn a lot about yourself, the applicant market and your own position by interviewing more candidates. The variety of skill sets on display can also hone your focus for what your future employee will do.

Hiring your first employee

Hire someone too early and you could have cash flow problems, a worker who has nothing to do and the added stress of management. Hire too late, and you could be inundated with work you can’t accomplish, which could lead to missing deadlines and losing out on business.

Finding the right moment to hire, therefore, can make the difference between a failed enterprise and a successful business. But how do you know when the time is right? The following tips can make this process a little less painful and provide options for making that first hire:

Start with a cofounder

If you’re a solopreneur looking to make that next step, bringing on an employee can be intimidating. Instead, hire a cofounder, or at least someone who thinks like one.When making that first hire, look for someone with cofounder potential and traits, such as complementary skills, similar values and vision, teachability, passion, emotional intelligence, flexibility and honesty. Your first employee will hopefully be one of your longest lasting and most knowledgeable.

Ask yourself: Will these tasks generate money?

It’s been said that the only two purposes of an employee are to: 1) make money for the business, or 2) save money for the business. If you’re confident a new hire will do at least one of those two things, go for it. In the early stage of a company, making money is more important than saving it. Typically, these early roles involve creating products (designers, developers, etc.), marketing products (growth hackers, content marketers, etc.) and supporting products (customer support, help desk, etc.).

Know your desired skill set

Before you search for an employee, you need to know what kind of candidate you’re looking for. It’s not enough to simply know that you “need some help” or “need a developer.” Get specific: You don’t want just a “developer.” You want a Javascript developer with GitHub experience able to create machine learning algorithms with educational applications, for example. The clearer your set of responsibilities are, the more effectively you can hire someone to fulfill those duties r.

Delay the decision by hiring a contractor

You may still be undecided over whether or not it’s time to hire. Don’t sweat it. Instead, test it. Try hiring a contractor with the same set of parameters you’re looking for in a full-time employee. The introductory hassle of onboarding a contractor is relatively low compared to that of hiring an employee. You can create a contract for one month, six months or a year. If it works out, you can transition this person into an official hire or look for a full-time employee.

The differences between hiring freelancers, contractors and employees

The major differences between freelancers, contractors and employees has to do with their relationship with the business owner. Freelancers and contractors are self-employed individuals, while employees are hired by the company. Freelancers and contractors typically set their schedules based on the needs of their clients and work out a payment schedule (typically upon completion of a job).

Employees, on the other hand, work the schedule established by the company and receive a regular paycheck on a schedule set by the company. As a business owner, you’re responsible for tax reporting on your payroll employees. But since freelancers and independent contractors are considered self-employed, they are responsible for reporting their taxes.

So what’s the best decision for your company? It depends on your needs, your resources and your ambitions.

When should you hire a freelancer?

Some people use the terms “freelancer” and “contractor” interchangeably, but there is a difference in the type of professional you are hiring. Freelancers usually work on smaller, short-term projects, while contractors work on larger, more long-term projects.

Freelancers are great options for specific support — for example, bringing on a digital marketer to get your social media up and running. If you’re not financially ready to bring on full-time employees for whom you have to provide employee benefits, a freelance relationship may be a better setup.

When should you hire a contractor?

Contractors generally come with a team of expert professionals who can get you the help you need, whatever it may be. They can handle specialized projects, such as IT, remodels, design and consulting. As your business grows, financial consultants can keep you on track with your financial goals. If you need highly specialized work that requires a team, contracting a company will ensure the job gets done right.

When should you hire an employee?

Not every company needs a large number of employees, but if you hold frequent meetings, rent an office space or interact with customers, you’ll want reliable employees to help support the business. Remember, just because someone looks good on paper doesn’t mean they’re a good fit for your business. They must fit into your company’s culture. Consider bringing on full-time staff if they can make you more money or improve the customer experience.

Why hiring globally might be your best move

The growing popularity of remote work has meant dramatic growth in the pool of available talent. Don’t limit yourself to just domestic workers, though. By hiring workers outside your country, you can save money, increase efficiency and still provide customers with superior service. Consider the following benefits to hiring globally.

A wider talent pool

As unemployment levels drop, the demand for skilled workers rises — especially for roles in software engineering or data science. By looking past your own borders, you can grow your pool of potential employees and have access to a wider swath of workers. For example, Poland, Slovakia and India are renowned for their pool of highly qualified tech professionals available to work remotely for international companies. Tap into this talent network to find the right fit for your company.

Cost efficiencies

Hiring overseas means access to employees who live somewhere with a much lower cost of living, which generally means lower salary expectations. The requirements for compulsory employer contributions and payroll taxes that increase business costs also vary by country. For example, countries like Germany and Japan generally require that employers deduct a certain amount of the employee’s pay for health insurance. But Australia and New Zealand, with public healthcare systems, do not require such employer insurance contributions.

Access to resilient international markets

If you run a growing, ambitious business, you may be eyeing overseas expansion. One of the biggest factors in your success will be having employees familiar with that market. You have a few options for growing an international presence: set up a local entity or subsidiary (abiding by local employment laws) or use an Employer of Record (EOR) solution, in which you designate a third-party company to handle payroll, HR compliance and employee tax withholding.

Compliance benefits

Employer compliance can vary depending on the country, and some are more strict than others. Whether you’re concerned about at-will employment, parental leave allowance or pension contributions, you can hire from countries whose labor laws align with your needs.

24/7 customer support

Customers expect fast and capable support, no matter where they’re based or when they contact the company. With just 9% of customers able to solve business queries on their own, customer service channels are more important than ever. Having staff in multiple international locations and time zones ensures someone will always answer the support line and provide 24/7 support for your customers.

Before you hire globally, though, you should look into any logistical challenges it might create. Despite the many benefits, hiring international talent can lead to internal communication challenges, scheduling conflicts across time zones, cultural differences, and discrepancies in pay scales. While these challenges can be overcome, they’re worth considering before building a continent-spanning workforce.

Related: 10 Pros (and Cons) of Hiring International Employees

Can college students solve your employee needs?

Different hires provide varying solutions for business, and hiring college students can infuse your company with young energy and ambitious workers. Whether you develop an internship program or employ them part time or seasonally, college students are often more affordable to hire than full-time employees and can support your team’s specific needs.

Creating a pipeline between universities and your business could be a worthwhile investment. Students are trying to get their foot in the door, and they can also provide your company with much-needed help. Here are a few benefits of hiring college students:

They bring fresh perspectives and new ideas

College students are at a unique stage in their lives and are just beginning to form professional identities. Eager to develop skill sets and apply classroom lessons in the professional world, they often bring welcome new perspectives to the table. This can be especially valuable in industries that are constantly changing or in need of innovation.

They’re highly motivated and ready to learn

The most ambitious college students are proactive and eager to take on new challenges — both promising traits for future employees. When you empower college workers, they’ll go above and beyond to learn and contribute to your organization. Additionally, young people are generally tech-savvy and comfortable with digital tools and platforms — a huge asset in today’s business landscape.

They’re cost-effective employees

Because school is the main priority, students are often willing to work for less pay than more experienced candidates; they’re also more open to part-time or internship positions, helping small businesses bring in new talent without breaking the bank. These internships can act as trial runs for potential full-time employment.

How to attract and hire the best salespeople

Just about any business needs persuasive salespeople. In order to sustain and grow your company, you need someone who can bring in new clients while you focus on the business itself. No matter what role someone in your company fulfills, everyone does some kind of selling on a regular basis — pitching investors or bankers, selling coworkers on a new project idea or vision, providing customer service, negotiating with vendors, etc.

Ultimately, though, it will be your sales team that drives your company’s growth. If you want to add top-notch talent to this group and increase your revenue, keep these things in mind:

Your mission should be exciting and purposeful

What are you looking to achieve with your business? Most people these days are looking to join a company because of its mission — its goal to change the world in some meaningful way. According to a 2021 McKinsey study, 70% of Americans say work defines their sense of purpose. Your mission doesn’t need to save lives, it just needs to inspire workers and point to a larger goal. Find salespeople who buy into this mindset, and they’ll evangelize the company or product for you.

Be the best salesperson you can be

If you’re looking to hire salespeople, you should also know how to sell. You may get to a point in your business where you’re not the main person bringing in new clients, but you still have ideas you need to sell to investors, journalists or marketers — and your own team. When interviewing a potential candidate, pay attention to your own energy level. Are you charismatic? Are you enthusiastic about the position and the opportunity? When the interview is done, you’ll want the candidate to feel like they’re ready to jump on your bandwagon and get started right away.

Know what else you can offer

If you can’t compete in the market with a high salary, you can at least offer other incentives that attract top talent and keep your business afloat. Many employees are looking for better work-life balance. Can you offer a flexible work schedule? Consider offering profit sharing or a higher commission in the near future. If your product or services are innovative or revolutionary, that can also be an incentive, as employees are eager to join a business that’s about to rapidly expand.

The best recruiting platforms for small business hiring

When it’s time to hire, finding quality candidates doesn’t need to be complicated. Job search sites can help you recruit and retain talent no matter your company’s budget or size. Some companies advertise jobs across a variety of platforms, and the sites you choose will determine who applies for your open roles.

Similar to reaching a target audience, you want to meet candidates where they already are — think industry-specific forums, alumni networks or on social media. But there’s also value in casting a wide net and posting on major job boards with millions of visitors. With so many platforms to choose from, which will best support your mission? Here are some of the top recruiting platforms to consider:


ZipRecruiter allows you to post job openings and receive applications from relevant candidates, as well as organize applicants in a resume database. Applicant tracking tools, including providing candidates with notes and feedback, also help you manage the hiring process.


LinkedIn is particularly effective for recruiting candidates in the business, finance and technology sectors. To help you find and hire top talent in — and outside of — your network, it offers job postings, resume searches and applicant tracking.


One of the world’s largest job search websites, Indeed allows you to search for candidates based on their location, experience and skills. It also provides rates for sponsored listings that prioritize your job openings in the search results.


In addition to job postings, Glassdoor features reviews from people who’ve worked at various companies. By providing insight into a company’s culture and employee satisfaction, the site can help attract candidates to your open positions.


With affordable pricing plans and an easy-to-use interface, Workable is a recruiting platform that’s particularly effective for small- and medium-size businesses looking to streamline their hiring process. It offers a variety of features, including job postings, applicant tracking and candidate sourcing.

Writing job advertisements to attract remote workers

The pandemic ushered in a widespread adoption of work-from-home policies that may be here to stay. These policies allow for more flexible working situations, and they’re an excellent way for businesses to stay competitive in the job market.

When writing your job advertisements, keep in mind it’s still just a listing, so you need to effectively communicate the benefits of working remotely and the job requirements. Consider the following tips for writing job advertisements to attract remote workers:

Communicate the remote nature of the job

Specify that the job is a remote position and include details about the type of work environment and equipment that will be required. Does this person need to work certain hours or be in a certain time zone? Spell everything out. If the job advertisement doesn’t say remote up front, many people will assume that it’s not.

Highlight the benefits to employees working remotely

Make it clear that the job offers the flexibility and autonomy of working remotely. Mention any perks or benefits that come with the position, such as a flexible schedule or the ability to work from anywhere.

Clearly outline the job requirements

Your job advertisements should clearly state the skills, experience, and qualifications that are required for the position. This will help you attract the right candidates and weed out those who are not a good fit.

Use language that resonates with remote workers

Use language that speaks to the realities of working remotely. For example, mention the ability to work from anywhere or the need for strong self-motivation and discipline. Also mention skills necessary for collaborating remotely, such as clear and concise communication.

Include information about your company culture

Whether in-person or working remotely, employees place a high value on company culture. In fact, this may be even more crucial in a remote environment, where your only coworker interactions are happening in chats and on video calls. Include information about your company’s values and mission in your job advertisements to help attract candidates who are a good fit.

It’s time to start hiring

By following these tips, you can make the most effective hiring decisions for your business. Keep in mind: no two companies are the same. Before you make a hire — or post a job, for that matter — consider the work you need done, the kind of worker you need to complete it, and where that person should be located. By outlining your needs early, you’ll save money (and headaches) in the long run.

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The 7-Step ChatGPT Formula for Peak Productivity and Profit



The 7-Step ChatGPT Formula for Peak Productivity and Profit

Tackle AI’s toughest questions with Ben Angel, mapping the business terrain for 20 years. Master the AI landscape and reach peak productivity and profits with insights from his latest work, “The Wolf is at The Door — How to Survive and Thrive in an AI-Driven World.” Click here to download your ‘Free AI Success Kit‘ and get your free chapter from his latest book today.

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How I Hit $100 Million in Annual Revenue By Being More Transparent



How I Hit $100 Million in Annual Revenue By Being More Transparent

Opinions expressed by Entrepreneur contributors are their own.

It’s a common nightmare — you’re walking through a busy hallway or giving a presentation only to look down and find yourself completely naked.

We’re inherently fearful of revealing too much about ourselves, and as an entrepreneur, this likely extends to your business as well.

But based on growing my own business from nothing to over $100 million in annual revenue, I can tell you less is not more when it comes to business transparency — more is more. Being open builds trust, and trust fosters customers and relationships in droves. The only exception is not giving away your trade secrets to competitors.

Here are three effective ways to build trust with clients and prospects by being more transparent (without leaving you feeling nightmarishly over-exposed).

Related: How Transparency In Business Leads to Customer Growth and Loyalty

1. Increase sales by 18% or more by increasing your Google reviews

Nearly everyone reads reviews before purchasing. One study found a whopping 93% of people read reviews before making a purchase, and on average, reviews produce an 18% uplift in sales. In today’s online landscape, people put almost as much weight on a Google review as they do on a personal recommendation.

The best way to increase your reviews is to simply ask! According to research, 70% of consumers will leave a review for a business when asked.

About four years ago, we had 486 reviews after servicing more than 90,000 clients. We started using Podium to send out texts or emails — based on customer preference — asking to leave a review on Google, the Better Business Bureau and Trustpilot.

By May 2024, we’d accumulated 2,312 five-star reviews, an increase of 375%. Keep in mind that our account managers have been very diligent about sending review requests to clients and only ask the clients most likely to give positive responses.

Another good way to increase reviews is to automate postcards at the close of an order thanking someone for their business and encouraging them to leave a review. A physical mailer is likely more effective than an email — one study that surveyed 1,200 consumers found that 76% trusted direct mail the most as opposed to online methods.

You might be wondering, “What about the negative reviews?” You’re always going to have a handful of bad reviews, but people look at the ratio of good vs. bad. If you have far more five-star reviews than one-star reviews, they’ll disregard the negative ones and assume it’s not the norm.

2. Improve lead generation by 105% by sharing your clients’ success stories

Sharing real marketing results has always been a priority for my business, PostcardMania. We currently have 944 marketing case studies and 139 video case studies that document real people sharing campaign specifics that led to more leads, revenue and new customers for their businesses.

We share these case studies far and wide with prospects via email and postcards in the mail to increase trust. But more recently, we began incorporating these stories into video social media ads. During a recent earnings call by Meta, CEO Mark Zuckerberg said 50% of all people’s time on Facebook and Instagram is spent watching videos, so naturally, we went that direction to gain more eyes on our services.

We put our 139 video case studies — real business owners talking about their successful campaigns — to work for us on Facebook and Instagram.

As a result, our social media leads doubled. In 2022, our average number of social media leads per week was 174, and then in 2023, the average lead count increased to 356 a week! That’s a 105% increase.

Of course, our use of social media in this case is part of a larger multi-channel marketing strategy that ties direct mail and digital ads together, so I suggest a similar approach if you want to see the same results (we’ve actually packaged our successful approach into a single affordable marketing bundle called Everywhere Small Business due to high demand from our clients to replicate this method). Campaigns that uniquely combine print and digital advertising using hyper-targeted mailing lists and lookalike audiences have been proven to work time and time again, so I highly recommend them.

It doesn’t matter what industry you are in, your customers’ success stories can be compiled and incorporated into your marketing plan to grow your customer base.

Related: How Problem-Solving Case Studies Help You Market Your Business

3. Convert prospects faster by dropping the velvet rope and inviting them in

Being transparent online will help build a positive image of your brand and bring in more customers — but you can also take this one step further and let prospects visit your business and interact with your products or services in person. One report revealed that 79% of customers want brands to go above and beyond what they are required to reveal and give more information, with two-thirds of them saying they would switch brands for more in-depth data.

At PostcardMania, we welcome clients to visit us and take a tour of our in-house printing facility. We also have a marketing conference twice a year where clients can meet their marketing consultants face-to-face and learn more about our business behind the scenes. These clients often end up being some of our best and longest-lasting relationships! You can do the same by hosting an event and opening your doors to the public. It doesn’t have to be a conference — you can start small with something as simple as a night of snacks and entertainment.

Related: 3 Ways to Personalize Your Marketing for Higher Engagement

Free samples are also a great way to show customers exactly what they are getting before they make a commitment. This doesn’t always apply to every business, but you can try to find a way to allow prospects to interact with your product or service on a deeper, more physical level.

Incorporate any of these tactics, and you’ll show prospects the most authentic side of you and your business. Believe me when I say trading in your fears about being super transparent for bold authenticity will reap real rewards in long-term growth and customer loyalty.

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The 10 Best and Worst States to Start a Small Business



The 10 Best and Worst States to Start a Small Business

There are many important things to consider when launching your own business or side hustle, and location is at the top of the list. Local and state laws can mean different taxes, zoning regulations and licensing requirements, so it pays to be strategic about your choice of state, city and even neighborhood, according to the U.S. Small Business Administration.

Related: 5 Things Not to Do When You’re Running a Small Business

After all, some 20% of new businesses fail within the first two years of being open, according to the U.S. Bureau of Labor Statistics (BLS). The BLS also found that 45% of businesses fail within the first five years. That number jumps to 65% after 10 years.

Capital on Tap, a company that offers a credit card and spending management platform for small business owners, analyzed BLS data to determine the percentage of startups that are still active after three years — and broke down the U.S. states with the highest and lowest chance of survival in three- and five-year time frames.

“There are over 30 million small businesses in the U.S., making up an enormous percentage of the economy, and as this number continues to grow, so will innovation and commercial drive,” says Damian Brychcy, chief executive officer at Capital on Tap. “This research should serve as a positive sign to entrepreneurs in the top ten states who are thinking about starting a business.”

Image Credit: John Coletti | Getty Images. Boston, Massachusetts.

Qualities of business-friendly states

Before diving into the data, it’s important to consider what factors make a state attractive for new business owners. And it’s about more than just starting a business. The following factors can help keep small companies afloat and lead to ongoing success:


Perhaps the most important factor of all, a business-friendly tax environment can keep costs down and put more money in your pockets. There are payroll, employment, income and corporate taxes to worry about, all of which can affect decisions around hiring and expansion. Some states also offer tax incentives for small businesses, which can remove expensive hurdles. Reviewing a self-employed tax schedule in your area can help.


If you want to run a healthy, growing business, you’ll almost certainly be hiring employees. The best states for small businesses will have a plethora of available talent and a workforce with high levels of college education. Starting a business near a college or university can also attract interest from recent graduates. This is especially prominent in the technology industry.


State policies regarding small businesses involve more than just taxes and deductions. Government programs can offer business owners grants and loans and incentivize investment from larger funders. Compliance is another factor. States can lower the costs of business by removing regulatory red tape, such as required government approvals or clearances.

Growth potential

You want to start your business somewhere it can thrive in both the short- and long-term. A number of factors can support this — for example, funding, investment in infrastructure and livability. A close proximity to sources of financing can help your company grow, as long as the area can support your workers and their families. States and cities with a low cost of living, good schools and solid infrastructure will not only attract talent but keep it.

U.S. states/territories with the highest rate of small business survival, per Capital on Tap 


1year average (%)

3year average (%)

5year average (%)









South Dakota












North Dakota
















North Carolina





With elite universities, a thriving tech hub, a strong economy and a highly educated workforce, Massachusetts tops the list. Nearly 82% of small businesses survive their first year. Boston is also a growing hub for STEM jobs and is home to many investors and potential employees. The state also boasts a strong Economic Development Incentive Program (EDIP) that provides tax and property incentives for job creators.


Not only does Wisconsin have a relatively low cost of living, but the state has one of the nation’s best public university systems (read: highly educated workforce) and a business-friendly government that offers tax credits, low-interest loans and grants to small companies. Wisconsin also runs a public-private capital initiative through the Wisconsin Economic Development Corporation (WEDC), which recently announced a $100 million investment in the state’s startups.

South Dakota

Taxes are the big selling point for starting a business in South Dakota. With no corporate income, personal income, property or business inventory taxes, the state makes running a small company affordable for owners. The state is highly affordable and has very few regulations, both of which lower overall business costs.


Almost 81% of small businesses survive their first year in Minnesota, a feat that can be credited to the state’s supportive business environment, educated workforce and relative affordability for a high quality of life. Minnesota also has nine small business development centers throughout the state, which offer consulting, mentoring, networking opportunities and access to capital.


With a high quality of life and low cost of living, Iowa is an attractive place to start and expand a small company. One of the biggest factors is extremely low energy and utility costs, which is especially important for manufacturing. Iowa cities also offer property tax incentives for small businesses and some of the nation’s lowest workers’ compensation costs.

U.S. states/territories with the lowest rate of small business survival, per Capital on Tap 


1year average (%)

3year average (%)

5year average (%)





District of Columbia




New Mexico












New Hampshire
















Rhode Island





Less than 43% of new businesses in Washington are still running after five years, thanks to expensive real estate, complex regulations and the nation’s highest statewide minimum wage ($16.28/hour). The state’s business and occupation tax is also calculated based on gross receipts, not overall profits, so businesses with slim margins will especially struggle.

District of Columbia

Washington, D.C., is one of the most expensive metro areas in the country, both in terms of real estate and overall cost of living. That means high salaries and high rents for offices or storefronts. The city’s business income tax and regulatory requirements are also relatively high, both of which can cut into profit margins.

New Mexico

High unemployment rates and limited access to capital make New Mexico a challenging state to open a small business. Skilled workers are lacking compared to surrounding states, and complex regulations can be a burden for business owners. More than 23% of small businesses fail within their first year.


Although Florida claims to be a thriving hub for entrepreneurs and small businesses, the data tells a different story: More than 55% of small businesses fail within five years. One of the biggest factors is the increasing frequency and severity of hurricanes, which has led to rising insurance costs. This affects both the available workforce and a company’s bottom line as premiums skyrocket.


Almost 23% of new businesses fail within their first year in Nevada, and that’s despite no corporate or individual income taxes. Part of the challenge is local governments: regulations vary widely depending on your city of choice, with different requirements for specific licenses and fees. A heavy reliance on tourism can also backfire when travel to the state falls off, such as during the pandemic.

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