Tabitha Jean Naylor is the owner of TabithaNaylor.com and a certified Inbound Marketing Consultant with over a decade of experience helping both B2B and B2C clients. We recently spoke with Tabitha about the challenges entrepreneurs face, especially when it comes to managing employees for the first time.

Tell us a Little About Yourself and Your Entrepreneurial “Street Cred”

I’ve had extensive experience in sales and marketing, working in industries such as advertising, defense contracting, insurance, publishing, and real estate. I’ve worked for Fortune 500 companies, so I know the inner workings of those type of companies, and I’m fascinated by the ways in which sound marketing can lead to an active sales funnel. The funny thing is that from the time I was a kid, I loved watching commercials, so maybe I’m just wired to think in terms of marketing and sales. But at some point, I became much more interested in inbound marketing. Probably when I got inundated with all those cheesy Cash4Gold type of ads that drove me crazy!

What are Some of the Challenges Facing Today’s Entrepreneurs That Weren’t as Common (or Daunting) as in the Past?

The truth is, there are so many more ways to create and monetize content that the possibilities are endless. But with that said, the challenges of thriving in the digital landscape are numerous. One of the biggest challenges I think we’re seeing is that consumers are so specialized now that unless you properly identify your target market, you may find success difficult to achieve. Consumers have so many choices now with where to spend their money that online business owners really have to understand the specific and unique wants and needs of their target market. Converting visitors into long-term clients is another huge challenge facing entrepreneurs. Content creators have to make a concerted effort to distinguish their products and services in such a way that they stand out from their competitors. If a business doesn’t create a compelling reason to persuade a visitor to engage with their site, it will not thrive.

These Days, What are Some of the key Factors That Impact Whether an Entrepreneurial Endeavor Succeeds and Flourishes, or Fails Within a Year or Two?

There so many variables that affect the success or failure of a business, but I really think that without passion, patience, and persistence, it’s probably impossible to ride through the many ups and downs that you often find with a start-up. The truth is, you open your business out of a passion for what you’re selling, but that passion can suffer many blows as you struggle to get your business going. Keeping that passion alive can steer you through those hard times. Conversely, losing that passion can drain you of the will to keep going. The same is true with patience and persistence, because once you lose the patience to weather the storms of business ownership, you won’t last very long.

And persistence, obviously, is another key factor. Do you have the strength, character, and self-belief to keep going when your business is struggling? Do you recognize that failures are just steps on the road to a breakthrough, or do you take failure as a sign that you should give up? Those first two years of a startup are so important; and if you apply the three Ps in a way that is positive and affirming, you create a mindset that can sustain your vision through difficult times.

When it Comes to the Money Management of a Company, What Metrics are the Most Important to Monitor and Focus on?

Well, there are obviously multiple metrics that can determine the success or failure of a business, but I really believe that revenue generation is the key. And part of that is tracking the return on investment, or ROI, which is one of the two basic metrics used to measure profit. ROI is popular because it can give a quick picture of how valuable a marketing activity has been for a company. But what’s even more important is having an accurate ROI; because an inaccurate ROI may give business owners the illusion that their companies are doing well, when in fact they are losing money. There are several ways to track ROI, but the key is choosing one method and sticking to it. ROI can help business owners determine if marketing expenditures are being spent in the right areas.

Finish This Sentence: “You Know it’s Time to Close (or Sell) Your Business When…”

People should close up shop when the business is no longer profitable (aka: you’re losing money). This one is a no-brainer. Although I’m also of the mindset that if someone loses passion for what they are doing, it might be time to re-evaluate options. Can the business be tweaked, modified, or changed in some way so that the owner will enjoy it again? If not, it may be time to close the doors. I really believe that if you don’t like what you’re doing, you should find something that you DO enjoy doing. Life is entirely too short to be miserable – and let’s face it, we spend an awful lot of time during our adult lives working.

For Entrepreneurs, is an Intense Passion for the Success of his/her Company or its Products or Services All That is Required to be a Good Company Leader?

An intense passion is without a doubt one of the most important aspects of owning a business, because if you don’t believe in what you’re selling, it will eventually show in how you market the products and services your company offers to consumers. However, leadership in business isn’t just about passionately believing in what you’re selling. It also requires the ability to listen to your team members; a collaborative mentality; the ability to make firm decisions; and the ability to be self-critical. An effective company leader can’t afford to develop an “I’m always right” mentality; because the truth is, no leader gets it right all the time. But equally important for good leadership is having a vision that doesn’t waver no matter the circumstances. In other words, through success and failure, true leaders maintain the core principles that underlie what their company stands for.

What is the Biggest Mistake you see Among Entrepreneurs who are Managing Employees for the First Time in Their Career?

Probably the biggest mistake I see with young or inexperienced entrepreneurs when it comes to overseeing employees is that they don’t trust the people they hired. In other words, some first-timers are so intent on showing that they are in control and in charge that they forget that they hired a team to relieve some of the pressure of making the company successful. No one will think less of you as a leader if you solicit ideas from your team. In fact, that’s one of the most effective ways to create trust among your employees; and when employees trust the person in charge, they tend to feel more incentivized to offer ideas and concepts that can improve and enhance business practices.

What are Some of the Most Important Leadership Lessons You’ve Learned From Running Your Own Companies?

Be the person you would expect someone else to be if you were in your employee’s shoes. Show compassion when needed – for example, if someone has a death in the family, don’t jump on them about blowing deadlines. But also stay authoritative, since the minute you don’t, people have a tendency to feel as though they are the boss over you instead of the other way around. While I’m not saying anyone should be a lunatic or an OCD tyrant, it’s important to maintain a balance between being a business owner and being a human being.

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