Marketing Strategies

18 Things To Know About Working for an Entrepreneur

Posted by: Ekalavya Hansaj Updated: 22 April 2020

Working for an entrepreneur can be one of the most rewarding experiences you can have in the business world, especially if you’re thinking about branching out on your own eventually. Every entrepreneur is a rogue in their way, succeeding because they’re doing something innovative and different.

An entrepreneur is likely to personally teach you efficient methods as well as some core basics about sales, marketing, business, and project management. Like any one person, the entrepreneur has both strengths and weaknesses. Every entrepreneur is different, but they do share some characteristics you should be aware of when you’re thinking about working with one.

As with most business entities, entrepreneurs may elect to hire full-time employees (FTEs) or contract workers (you’ll get a 1099). If you’re an FTE, you should be getting taxes taken out of your paycheck and benefits. If you’re on a 1099, you’re responsible for withholding your taxes, and you will not get medical benefits. Some entrepreneurs are so excited about their ideas that they aren’t the best at explaining this, especially to recent college grads.

As you think about your journey in business, here are eighteen things to consider if you would like to work with an entrepreneur.

                1. Everything is on a Rush Schedule (Except When It’s Not)

When you’re working for an entrepreneur, you’ll quickly learn that everything needs to be done yesterday. No matter how organized an entrepreneur is, to keep up with a rapidly changing world and a competitive environment (especially if they’re in tech), they need to complete projects exceptionally quickly.

Some things might sit on the metaphorical back burner for a while, but when an entrepreneur’s focused on something, it’s a target. As their employee, you must follow suit. If this is overwhelming, do yourself a favor and communicate clearly. Set out all the things you need to do and ask the entrepreneur to help you re-prioritize the list. If everything’s on fire, you still need to put tasks out in order.

                2. Entrepreneurs Love to Mentor

Do you want a job in which you will learn things? Learning is one of the significant benefits of working for an entrepreneur. Under her guidance, you can learn all about a particular industry, niche, or general business very quickly. Entrepreneurs tend to work closely with their employees (especially if you’re the only one), resulting in much unintentional mentorship.

Formal mentorship is also possible when you work directly with an entrepreneur. As you discover more things you’d like to learn about, keep track of those things and ask for structured time and mentorship. Entrepreneurs love teaching and generally enjoy being very giving of their time when it comes to that.

                3. Expect to Manage Your Own Time

While some entrepreneurs are micromanagers or paranoid due to previous negative experiences with employees, most expect you to be able to manage your own time, whether you’re hourly, salaried, or on a per-project basis. Getting the work done efficiently is the most important thing for most entrepreneurs, and regardless of how they are with time management, they’ll expect you to be an expert at managing your own time.

Even if the entrepreneur doesn’t ask you, it’s helpful if you track your time and tasks. Using a free tool like Airtable, this takes only a few minutes per day. It will help the entrepreneur to see how you’re spending your time, and if you feel that a task is possibly a waste of time or not worth the ROI (return on investment), you can use the numbers to advocate for your case.

                4. Expect to Organize the Entrepreneur

Entrepreneurs have to be self-directed. Most are excellent with great concepts. Even the most Steve Jobs-esque of all entrepreneurs can only do so much, however. Eventually, they’ll experience some overwhelm, and whether they’re great at communicating about when they need help or not, you’ll need to step in and organize the entrepreneur.

If you’re the first employee the entrepreneur has had, you’ll need to understand that this is a challenge for them. Trusting an employee to do critical tasks isn’t always easy for the entrepreneur; they have to learn to let go. Give her the time and space to do this, but make sure she knows you’re there to handle the tasks she hired you to do.

                5. Set Boundaries

You’ll have to set boundaries with the entrepreneur. Entrepreneurs have little boundary between their personal and professional lives sometimes. After all, they’re living their passion! However, they need to be reminded that they can’t take advantage of your time. Boundary setting rules are especially true for holidays and time you have scheduled off.

Decide what your boundaries are. Then stick to them. Boundaries also relate to your job duties. Are you managing an entire business with the title and pay of assistant? Either you need a raise, or the entrepreneur should expect less from you.

                6. Entrepreneurs Chunk Tasks—Then Go AWOL For a While

Chunking is a method many successful entrepreneurs employ. It means doing specific tasks in chunks to improve focus. For example, let’s say you have four blog posts to write. Instead of spreading them out between other distracting functions during the day, you sit down and plow through them all at once. This method leads to a focused mindset for many.

As an employee of an entrepreneur, this can affect you. You might get a lot of necessary information or project details—then hear nothing about the project for weeks. That’s because entrepreneurs get hyper-focused on specific things when they have the time. This style takes some adjustment for those not used to chunking.

                7. Work Hard, Play Hard

Entrepreneurs tend to work hard and after work, they play hard. That means they might have a very active personal life or party lifestyle. Are you getting invited to an after-work event? Expect something a bit extravagant. Don’t be surprised if you find out the most frugal entrepreneur treats himself to an expensive vacation or frequent rounds of golf.

Entrepreneurs know that long work hours require some active vacation time to balance it all out, and you’re expected to understand that, too.

                8. Entrepreneurs Need Finishers

All entrepreneurs are fantastic at generating ideas and setting up large projects. However, many aren’t good at managing all the details those projects entail—or finishing one of the many projects they start.

Their lack of ability to finish projects before starting new ones is significant for you, though—it means you’re precious to an entrepreneur so long as you can complete projects and tie up all those loose ends.

                9. Too Business-Minded, or Not At All

As an entrepreneur, it’s tough to focus. It can seem like an entrepreneur boss is either too focused on the business, or not in a business mindset at all. Many genius entrepreneurs have been described as flighty, fleeting from one project to the next.

Be prepared to deal with a personality that sometimes seems erratic in this regard—and to retain your value, always be ready to pick up the slack.

                10. Business and Personal Get Conflated

Be aware that many entrepreneurs do not have a healthy boundary between their work and their social lives. That’s because their job requires so much of them, including personal investment from their family and friends. Don’t be surprised if they also employ friends and family, or if you meet their kids on your first day at work. You might even get to work with their dogs.

Especially if you’re in an assistant role, you might have to do some oddball, personal tasks, like deposit personal checks, go through private mail and email or get their kids from school.

                11. Personal Quirks Become Professional Quirks

Along with this blending of personal and professional comes the fact that most entrepreneurs are their brand. They do not have an individual personality and a professional one, and it’s the same. While that can be a strength when it comes to branding, it also means you’re going to have to get used to a healthy personality with some serious quirks.

No one succeeds as an entrepreneur without being unique, and that means having some rough edges or individual methods.

                12. Multi-Project Workload, Constant Starting

Most employers require you to multitask, but few require multitasking in the same way as entrepreneurs. Most entrepreneurs know that they’re best at starting projects, leaving them in capable hands, and moving on to start the next best thing.

Imagine an entrepreneur like an admiral of a fleet. You, whether an assistant or project manager, are a captain. The entrepreneur jumps from boat to boat, often building new ships, expecting you to repair, maintain, and finish the construction of all the other vessels. Are you ready for that challenge?

                13. Expect Lean Times and Feast Times

Depending on the business size and the investment in it, you should expect any startup or entrepreneurial effort to have lean times and feast times. When the crunch comes, you’ll feel it. There will be fewer lunches at the company, stricter budgetary approval, and more. During feast times (after a round of funding, for example), you’ll see more generosity.

This variation is a scary thing, primarily if you’ve previously worked in a more corporate environment where there were never worries about a paycheck. You’ve got to trust your entrepreneur to lead you successfully through those lean times.

                14. Entrepreneurs are Particular About Their Brands

Especially in a small business, entrepreneurs tend to be more hands-on with their brands than those working in corporate America. They’ve birthed this brand, product, and service, and they’re still involved in its success. They may eventually decide to sell the company and move on to another thing (many serial entrepreneurs do this), but while they’re still involved, they’ll be meddling in every bit of media about their brand.

If you’re managing social media, expect your entrepreneur to demand approval of every tweet. It’s about the brand more than distrust, but it can be an annoying detail of working with an entrepreneur.

                15. Entrepreneurs Like Contracts (and They Should)

Entrepreneurs usually like having contracts for everything. As an employee, that’s particularly helpful, especially if you’re a contract worker. Get used to hearing about contracts, creating them, editing them, and signing them. You may also be responsible for reminding your entrepreneur about the importance of contracts. Ensure they’re a part of the process for working with a new client, as entrepreneurs can be enthusiastic about diving straight into work.

                16. Entrepreneurs Can Be Frugal, But They Know Your Value

Most entrepreneurs have fought to get to where they are in business. They often face internal conflict when it comes to employment: they know it’s important to pay their employees well, but they also have to maintain a strict budget to help their business succeed.

In addition to facing this at salary negotiation, you’ll also find the entrepreneur hemming and hawing over the cost of software, vendors, and other services.

                17. There is More Risk of Late Payments

Working with an entrepreneur is rewarding—but risky. There are many horror stories about employees who got paid in sweat equity or stock instead of cold, hard cash—often leading to regrets. You’ll become personally attached to your entrepreneur boss, but that never means a delay in payment is acceptable.

Payment concern is one of the harder boundaries to draw, but it’s a good one for your mental health. Additionally, before you get involved with an entrepreneur professionally, check out the Glassdoor reviews of their current or previous ventures to ensure there’s a low risk of getting stuck without pay.

                18. Entrepreneur’s Job: Selling Their Dream

It’s inspiring to see an entrepreneur in action. They believe in their dream, and it’s their job to sell it. Sometimes entrepreneurs expect you to have the same level of enthusiasm for their vision, but at the end of the day, when it’s not your baby, it’s hard to love that dream as much as they do. The best you can do for an entrepreneur is to be the ultimate support person. Think of yourself as the Robin to their Batman.

Accepting a position with an entrepreneur is a wild ride. On that ride, you can learn a hefty amount of information and acumen quickly, but it also has its own set of challenges. However, the best way to be inspired to become an entrepreneur or to try out the lifestyle is to work with one.


An entrepreneur who chased success till it chased him. Founder at Quarterly Global. Father to Mayra Hansaj and Husband to Anjali Hansaj. Author of “The Criminal Wolf” and “Rise of the wolf”. 114 Days in a slumber haunts me yet.

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