How To Be A Serial Entrepreneur

Originally published on Huffington Post

More than a decade ago, I made the life-changing (aka turned upside down) transition from the corporate world to the realm of self-employment. Being able to set my own schedule, control my income, follow my passion and be my own boss has been equal parts rewarding and terrifying, and it’s something I think everyone should experience.

As the brains behind three successful online platforms (my latest venture is The Bullet), I feel like I’ve picked up a few valuable pieces of advice that can help those looking to venture out on their own. After watching many others make the leap to entrepreneurship (with mixed results), I’ve developed five key thoughts for every new business owner to consider before taking the (very big) step.

1. Have a Plan

Being an entrepreneur is not all sunshine and rainbows. Contrary to what you’ve seen on your favourite movie or TV series (I’m looking at you, Sex and the City), self-employment won’t immediately provide you with a big enough income to buy a closet full of Manolos. To be a successful business owner, you need to have a clear, well thought-out and realistic plan before you start.

A plan will help you achieve your short-terms goals and enhance your business’s productivity. The same way a plan for an essay, job application or blog post can guide your thinking, a sound business plan will allow you to focus your energy and time. Planning won’t guarantee success but it will give you a clear direction when you run into speedbumps.

However, one note of caution – don’t get too caught up in the gritty details. I’ve also seen too many people fall victim to “analysis paralysis”. Get your ideas documented and then get to work testing them. You will undoubtedly be fine tuning along the way (and forever).

2. Organize Your Finances

Despite the fairy tale stories of Silicon Valley unicorns, businesses need to make money to be successful (unless you’re Amazon, I suppose). When you start a new business you need to focus on the numbers. You can have the passion and a brilliant idea, but if the business model isn’trealistic, your success will be short-lived and attracting investors will be challenging. Before I seriously start thinking about launching a new business, I always ask myself: will this make money?

Before you hit the ground running, meet with a personal financial advisor to understand how you are going to finance yourself until your business can pay you. Take their advice seriously. Be aware that there is no guaranteed paycheck with self-employment and plan to set aside a realistic sum of money to support yourself during your businesses infancy. You may have to dip into your savings or take out a loan.

3. Find a Gap in the Market (Then Fill It!)

I recently read a piece on Forbes, and one line really stuck with me: “the best entrepreneurs don’t come up with great ideas, they solve market needs.” A basic principle of economics says that the end consumer’s desire and willingness to pay for a specific good or service depends on its ability to fulfill one of their needs. The most successful businesses satisfy a general consumer need that is currently not being met. Do your research and identify a gap in the market that you can fill–and then make sure you do it better than anyone else.

With all of my businesses, each one has had a distinct offering, yet they have all met a similar consumer need, which is making people’s lives easier (ain’t nobody saying no to that!). With Sweetspot we were a filter and trusted friend sharing the latest and greatest lifestyle trends. Eluxe was one of the first ecommerce sites in Canada offering Canadian women contemporary fashion clothing and accessories along with editorial content to entertain and inspire they wardrobe choices. And now The Bullet gets people up to speed on the news in a simple, light-hearted way that is less overwhelming, depressing (and fake) than many other media outlets.

4. Leverage Your Network

“Network” is the ultimate buzzword these days, and for good reason. When you’re an entrepreneur, your network can make or break your business. You can’t be scared to reach out to anyone and everyone you know and ask for a favour. Chances are your business won’t be an overnight success (and if it is, please share your secret!), which is why having a strong network is so essential. Leverage any contacts you’ve made at previous jobs and the connections your family and friends may have.

I have been very fortunate over the years to amass a strong, loyal network of colleagues that have supported me through my various endeavours. Many are previous clients, business associates and school alum who provide a diverse set of skills and points of few, that have been invaluable in my continued success.

And, don’t undervalue the importance of social networks like LinkedIn, Instagram, Twitter and Facebook. In this digital age, taking your business online can be the difference between success and failure. I often say “If you’re not online, you don’t exist.”

5. Surround Yourself with the Best People

This is really a sub-point of #4. There’s an old saying that goes “you’re only as good as the people you choose to surround yourself with.” In the world of self-employment and start-ups this couldn’t be more accurate. I named my consulting firm, Good Eggs, for that very reason. If you hire the best, you’ll be the best. Although you’re working for yourself, you’ll need to rely on others to help your business grow. Nurture these relationships. Create a strong work culture and establish support structures for your employees and your organization will blossom. Some of my employees have been with me since my first solo venture and have become lifelong collaborators in the process.