Practice Management Small Business

Do You Have What It Takes to Be a Serial Entrepreneur?

Written by Nellie Akalp

Some people are content to continue to build the business they started, throwing all their time, money, and energies into growing that company. Others are more interested in exploring different opportunities, both in and out of the accounting field. Which is the best choice for you? Should you focus on the one opportunity you’re currently involved in, or create an exit plan to launch another business? Or is it possible to run two (or more) businesses at one time? As a serial entrepreneur myself, I’ll help you identify the pitfalls and/or benefits of each option.

Ideas, Ideas, IdeasDo You Have What It Takes to Be a Serial Entrepreneur?

Entrepreneurs are creative, motivated, and passionate—and therefore tend to get bored easily. There’s nothing like the thrill of starting on a new adventure. And, once you’ve actually made the leap to entrepreneurship, the possibilities of starting another business don’t seem so far-fetched. After all, you’ve already laid the groundwork and you know the steps, so why not do it again?

When my husband and I started our first business in 1997, we were in law school, had $100 in our bank account, and ran our business from a two-bedroom apartment. Then, in 2005, a software giant bought our business for $20 million. We thought we were golden, but in all honesty, the boredom settled in quickly.

We were working for the new company, but quickly realized we needed to be our own bosses. We had no exit strategy, and a noncompete contract stopped us from starting a similar business for four years. So, you can be sure that as soon as our noncompete term was up, we started our new business, CorpNet, and we’ve been back in the entrepreneurial world we love for the past nine years.

If you find the entrepreneurial bug biting you again, start by asking yourself:

  1. Am I simply bored with my initial business? If so, could I make changes to make it more interesting (i.e., delegating boring stuff so I can focus more on the big picture, finding a new market, opening a second location)?
  2. Should I sell my existing business and use the proceeds to finance my new venture? Assessing the value of your business will help you decide if this is a viable option or if you need to take time to build up more value before you can sell. Then ask yourself if you can really let go of your baby and let someone else run it the way they want to.
  3. Should I purchase an existing business to merge with my current business? This possibility can save you time and money, especially if you’re able to keep the existing staff of the business you buy.

Another option many serial entrepreneurs consider is expanding their existing businesses. Adding a new division or new services and products is a less complex option and allows you to benefit from the brand you’ve worked so hard to establish with your initial business. If you can partner with another company to offer services, you’ve hit upon a great solution. Not only are you expanding your business with less expense and mental output, you’re also expanding your entrepreneurial dreams by getting involved with multiple ventures.

Before Making the Leap

Do You Have What It Takes to Be a Serial Entrepreneur?


You didn’t start your initial business without doing the research, so don’t think you can start another business (or add on to your existing one) without taking the same steps. In fact, this process is even more important now, because you have more to lose. Ask yourself:

  • Are operational systems in place and running smoothly at your first business?
  • Do you have a trusted employee who can focus on the original business while you start the second one?
  • Can your business finances support a new venture or will you need to get a loan?
  • Can you mentally (and physically) handle two businesses?

In thinking about your next idea, how sure are you about its viability? Do you know if it’s something consumers want, need, and will pay for? Talk to your loyal customer or client base about your ideas and get feedback. You can also take a poll on social media or via email, gather a focus group, or talk to experts in your community for more input.

Finally, it’s important to make sure your family and friends are ready to handle you as a serial entrepreneur. Sometimes an entrepreneur can get so involved in his or her own world that the rest of life gets pushed to the backseat. Make sure you have the support and help you need to make it through another startup.

What do you think? Are you ready to launch another business? Let us know in the comments.

About the author

Nellie Akalp

Nellie Akalp is a passionate entrepreneur, small business advocate, and mother of four. She is the CEO of, a trusted resource for Business Incorporation, LLC Filings, and Corporate Compliance Services in all 50 states. CorpNet also offers business dissolution services. Nellie and her team recently launched a partner program for accountants, bookkeepers, CPAs, and other professionals to help them streamline the business incorporation and compliance process for their clients. More info at:


  • Hi, Nellie
    Thanks for providing a good information on serial entrepreneur. A serial entrepreneur needs to have good time management skills, strong discipline, decision-making skills. We can learn from some of the most successful serial entrepreneurs like Richardson Branson, Jeff Kinney, etc.

  • Great post about serial entrepreneur, makes me want to start yet another new business. I think when entrepreneurs have a business idea about creating a new startup they don’t do enough market research, especially when it comes to what people are searching for on Google. Simplified here: You shouldn’t be trying to sell yellow widgets if everyone is looking online for red widgets. That SEO knowledge could go a long way to helping when strategizing a business plan.

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