More Than Bootstraps: When It’s Time to Bring in an Outside Expert


By Jeremy Office Special to The Pineapple “It’s not the load that breaks you down, it’s the way you carry it.” – Lena Horne When you first start a business, taking a do-it-yourself approach is less of a choice and more of a necessity. As a startup business owner, you typically wear all the hats—you’re the CEO, the CFO, the marketing director, the sales team and the office manager, all rolled into one very busy package. That approach usually works for a time, but it’s not sustainable over the long-term, especially if you hope to grow your business to any significant degree. Eventually, you are going to need some help. But many entrepreneurs have trouble recognizing when it’s time to find that outside help. While that’s not surprising, it’s a mistake that may put their entire future at risk. Below are six signs that you may need to bring in an outside expert to help you in your business. 1. You can’t be objective: When you’re deeply involved in your company’s day-to-day operations, it can be hard to step back and take a big-picture view. No matter how smoothly your business seems to be running, there’s a good chance there are things you could be doing better, if only you could see them. An outside expert or consultant may be able to provide the perspective you need to make a much-needed change. And if you have a nagging problem, sometimes all it takes to solve it is a fresh set of eyes. As management consultant Peter Drucker once said, “My greatest strength as a consultant is to be ignorant and ask a few questions.” 2. You’re losing sleep: At some point, managing all facets of your business is simply too much for one person (or a small leadership team) to handle on their own. If you’re waking up at night in a cold sweat worrying about business issues, that may be a sign that it’s time to hire a consultant or other expert who can help relieve some of the stress. 3. You don’t have the skills: Few people, if any, are equally adept at every aspect of running a business, especially as the organization becomes more complex. You may excel at business development but have no interest in managing employees. Or perhaps you’re a whiz at coming up with new products, but have no idea how to market what you sell. It’s not a weakness to accept that there are certain things you’re just not that good at, and to find someone else who is good at them to do it for you. 4. You’re screwing things up: A seat-of-the-pants approach often works in the early stages of a business, when you can write off small mistakes and goofs as a learning experience. But at some point, those errors become more costly and can even jeopardize the future of your business. Accounting problems, bad (or even illegal) hiring practices and legal snafus are not unusual in smaller or young businesses. Unfortunately, even seemingly innocent decisions can have major negative consequences. As your business gets more complex, bringing on experts who can help you avoid mistakes is simply a good risk management strategy. 5. You’re not sure what step to take next: Are you unsure what the next move for your business should be? Bringing in an expert can help you find the answer. Maybe you want to move into a new market, introduce a new product or service, or acquire another firm. A consultant can help you analyze the options and find a path forward that’s right for you and your company. 6. You need more capital: The advantages of building your business from scratch are numerous. But often, business owners hit a growth plateau beyond which bootstrapping won’t help them get to where they want to be. If you’ve reached the point where you want to take your business to the next level but lack the financial resources to do so, it may be time to look at outside investors and business experts who can provide the support you need, financial and otherwise, to grow. Building a business is hard work, and it’s often work that is done alone. But it doesn’t have to be that way. Knowing when it’s time to give up bootstrapping and seek outside help is essential to taking your company to the next level. Jeremy Office, PhD, CFP, CIMA, MBA is founder and Principal of Maclendon Wealth Management in Delray Beach. Maclendon provides comprehensive financial advice to successful, affluent individuals that have an entrepreneurial mindset and are looking for a dedicated team and exceptional wealth management services. He is also co-founder and Managing Partner of SJO Worldwide a venture capital company. 855.MAC.WEALTH