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Entrepreneur Tips: Hiring Your First Employee

For many entrepreneurs, hiring an employee for the first time is a major decision. Especially if you’re bootstrapping, you may not even be taking a salary yourself, so it can be surreal to consider hiring and paying an employee. But there are massive benefits to bringing in additional hands. First, and most importantly, bringing somebody on – even if it’s part-time, or remote – can give you the freedom to spend more time on revenue-generating activities.

We recently tuned into an episode of Brave + Boss, hosted by Kristi Soomer, and she offered some great advice on just this topic. Soomer started her ethical fashion brand, Encircled, out of her own condo. She was a solopreneur for a good stretch, but eventually found that in order to optimize growth, she needed to optimize her own use of time. She didn’t even pay herself for the first two and a half years of her business, and her only regret during that time is that she took so long to start hiring.

How do you know it’s time to hire your first employee?

According to Kristi, if you’re a time-burdened entrepreneur, the best thing you can do for yourself is go ahead and start tracking your work activity. Every hour, for a week, write down what you’re working on for your business. Then, go back and highlight the items that you know drove revenue – whether that’s a social post, an email, working with influencers, pitching the press, attending meetings. If you can track revenue back to that activity, it’s worth your time.

As for all the tasks in between, those are typically items that can easily be taken over by an assistant or part-time employee. For instance, a new employee could be quickly trained to answer customer service emails, create social posts, ship orders, or even help pay the bills. If you’re spending any large portion of your time doing admin tasks, when you know that you could focus more energy on your specialty (whether that’s pitching or designing or speaking at events, or whatever else) to grow your business, then you know it’s time to bring somebody on.

Deciding whether to bring someone on part-time or full-time?

You don’t have to go full-force, full-time, salaried with benefits to start. This can be as simple as you want it to be.

Once you have your list of admin tasks that take away from your actual revenue-generating activities, you’ve got the beginning of a job posting. Whatever you think will help save you time and keep the gears turning, shifting some of those tasks off your plate is likely to benefit your business in terms of your ability to optimize growth. Just google a templated job description for the type of position you’re looking to hire, and tweak from there.

Going from zero employees to even just ONE can be a big step, so there’s no harm in starting out part-time. As your employee onboards and starts getting into the groove with your business and your expectations, then you’ll undoubtedly find more ways that they can contribute and take more tasks off of your plate. Whether that means expanding their hours, or bringing on another employee, at least you’re headed in the right direction.

Should you give your early employees equity?

In venture-backed tech firms, it’s pretty common to see early employees sign on with equity. That’s what we see with startups, simply because of how much air-time those big unicorn tech firms receive. In those type of venture-backed businesses, giving equity can be a useful way to attract top talent, but should you consider giving equity to your early employees? Kristi Soomer provided a simple answer. You probably shouldn’t even think about it – especially if you don’t know them very well.

Giving equity means giving away pieces of your business. If you’re bootstrapping, chances are you haven’t even paid yourself. You’ve raised the value of your company by pouring your time, energy, sweat and tears into that business – and you’re looking forward to delayed rewards. (Kristi actually calls this “sweat equity” – which we’re kind of living for.)

Each time you give equity to an employee or investor, you’re creating a partnership in your business that can last as long as the business exists. If you do end up giving away equity in your business, you want to make sure you’ve found the right partner (or partners). So take your time – you may find that your first employee turns out to be your best employee, and you can always revisit this decision as you grow.

Should you consider hiring remotely?

Bringing on a part-time employee or virtual assistant to start makes a lot of sense – but not every business has a brick-and-mortar location, so doing it locally isn’t necessarily a given. If you’re still running your startup out of your residence, you might choose to look at remote workers. You may need somebody who is a jack of all trades, or you might need somebody with a distinct speciality – and that type of talent is not always easy to source locally. Posting remote positions opens up the candidate pool in ways you may never have expected. You can even look into hiring part-time/remote through gig-work sites like Upwork or Freelance.com, if you’re in a hurry.

How can you manage a remote employee?

It’s 2020. There’s a worldwide pandemic. Even if you find local talent to help you with your business, you may not be able to work in the same physical location. So it’s important to make sure that you have the right infrastructure to collaborate remotely.

Start with communications infrastructure. A virtual phone system like Tresta makes it easy to add users and call flows as you begin hiring – and it’s less expensive than other options like providing your employee with a second smartphone or trying to set up physical business phones if they are in-office. With a virtual phone system, you can also set up voicemail boxes that are shared by everyone in your organization. Obviously, you’ll want to make sure they have a company email address, or access to your shared inboxes. You might also want to look at a messaging tool like Slack, Skype or Microsoft Teams.

From there, you can look at other collaboration tools. For issue tracking, larger teams use robust tools like Jira, but for a startup with one employee, or even for several employees, something like Trello may work just as well. If you need to share files, you can use a platform like Box, or you can go as simple as sharing files on Google Drive. You can find more tools that can help your team succeed remotely here.

At the end of the day, the most important aspect of bringing on a remote employee is setting clear expectations, and checking in regularly.


In the early stages of building your business, you may be nervous to hire your first employee, but there’s nothing worse than having regrets later on down the road. Take Kristi Soomer’s advice and start building your team now, so that you can focus in on the tasks that will truly take your business to the next level. And tune into the Brave + Boss podcast for more sage advice (and to show support for a fellow entrepreneur,) as they head into their fourth season.