How My Business Didn’t Fail

Career Geek Experts

Entrepreneurs love talking about how hard they work. They love telling anyone who will listen about how they get up at 5 a.m., like Ursula Burns, and don’t sleep until 4 a.m., like Fran Lebowitz. They love explaining all the projects they’re juggling, how many new employees they’ve brought on, and what markets they’re expanding into currently. More than anything else, entrepreneurs love talking about their success.

What they don’t ever talk about is their failures.

Even successful entrepreneurs fail. My first three start-ups each crashed and burned in less than a year. The fourth has struggled on for more than five years, becoming a veritable SMB, but unlike other entrepreneurs, I hardly call my work a success. Instead, I prefer to say I haven’t failed. Perhaps in a few more years I will finally be comfortable admitting triumph, but until then, I will revel in my near-misses and celebrate my avoidance of utter catastrophe.

Every entrepreneur’s road to success is different, but the paths that lead away from failure are essentially identical. After countless failures, I found some semblance of success by focusing my efforts on the following fields:


Communication is the backbone of business. If an entrepreneur can’t express her ideas comprehensibly, she won’t succeed — regardless of the soundness of her business plan or the vastness of her network. Communication is an essential leadership skill, which entrepreneurs use to define the direction of their businesses, inspire and motivate their teams, and attract new customers. Businesses simply cannot survive without it.

It is important to note that no one form of communication is more vital than another; I began my career as an excellent written communicator who clammed up when face-to-face with people. In doing so, I missed opportunities to sell my brand, bolster employees’ morale, and more. Conversely, entrepreneurs who are horrendous in text should consider enrolling in school to improve their writing skills, as producing well-worded documents — including emails — is a necessary business skill.

Cash Flow

While an inability to communicate will generally prevent a business from getting off the ground, cash-flow problems will slowly but surely cause a business to crash and burn. According to TIME, cash-flow mistakes kill a quarter of all businesses — including a quarter of mine. Healthy cash flow is a delicate balance between spending and saving, and few entrepreneurs get it right the first time.

A primary goal to establishing healthy cash flow is managing debts. Accruing small-business loans is perhaps the most common way to gain enough funding to start a business, but debt payments can get out of hand quickly. While some form of credit is typically essential and even beneficial for cash flow, business owners should avoid spending most of its cash on payments.

Instead, most of a business’s cash should be reinvested into the business, helping it grow. Expanding the customer base, adding to the workforce, and even accumulating more inventory are better uses of hard-earned funds than debt. Entrepreneurs who are struggling to maintain a consistent cash flow and are tempted to take out more lines of credit might consider funding alternatives, such as factoring finance or crowdfunding. These methods provide available cash without requiring future payments that hamper a business’s flexibility and reduce its competitiveness.


In dozens of ways, I lost control of my first few businesses. In one, I micromanaged so thoroughly that the business didn’t have space to grow; in another, I was so disconnected from the business that I wasn’t aware of when the day-to-day operations slowed to a stop. Great leaders have the right tools and techniques to establish the proper amount of control, guiding their businesses to success.

There are dozens of tech tools I can thank for my most recent business feat. For start-up entrepreneurs with a skin-tight budget, I highly recommend free online tools, many of which interested entrepreneurs can find on curated directories.

However, I found commitment to be more important for exerting the right amount of control. In my first venture, I was overly committed to my work: I was so eager to create success that I stifled my business. In my second, I was burnt out and dispassionate about the business idea, and it fizzled without my input.

Entrepreneurs should be committed to seeing their businesses grow — but they should also be confident and comfortable in other aspects of their lives. Without balance, entrepreneurs and their business will surely fail — and those late nights and early mornings will go to waste.

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Career Geek Experts

Career Geek Experts

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