Management April 22, 2015 Last updated September 18th, 2018 2,668 Reads share

The 5 Most Valuable Players on the Entrepreneur Dream Team

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One of the best parts about being an entrepreneur is the opportunity to live out your passion and the freedom to make a living running a business the way YOU want it to operate.

Yes, marching to the beat of your own drum feels REALLY good.

Most of the time…

The downside to being an entrepreneur is that you’re often left to take the lead on EVERYTHING yourself, which can take you away from doing the very thing you love most about your business.

Really I just want to do what I want to do…

I’m a Mompreneur and small business coach for moms. I operate an online community for moms. I love to write and consider myself a content machine, so my primary communication channel for acquiring new clients and online community members is content marketing.

Makes sense, right? 

I also really enjoy seeing other moms make it happen for their small or home-based businesses, so being a professional cheerleader for them is right up my alley.

Ideally, I’d spend my workdays writing and coaching.

Yeah, not so much…

There’s the whole BUSINESS side of running a small business.

Someone needs to balance my books, make sure my sales policies are fair, yet firm, update my WordPress site to make sure it’s actually functioning, and oh, do I have the right insurance coverage for my consulting business?

Getting bogged down with the critical yet not-so-interesting-doesn’t-really-fit-what-I-love-to-do areas of my small business does NOT make for a happy or a passionate entrepreneur, my friends.

But the key to a viable and sustainable long-term business is the ability to effectively manage your operation and stay ahead of – or at least on top of – your key areas.

Jim Collins author of the best-selling book “Good to Great” said great business leaders start by “getting the right people on the bus, the wrong people off the bus, and the right people in the right seats on the bus. First the people, then the direction…”

So entrepreneurs, I present to you my perfect recipe for the right people on your small or home-based business team.

Sidenote: This recipe takes into account a bootstrap mentality and an entrepreneur working on a very lean operations budget.

The Entrepreneur Dream Team

There are five key members on the entrepreneur dream team, the most important one? LeBron James the MVP Accountant.

Your accountant is your most valuable player. You NEED an accountant. 

The first and in my opinion, MOST important member on the entrepreneur dream team is your “LeBron James,” so to speak. A business owner operating in the United States needs an accountant for one reason, if nothing else – to remain “friends” with an entity that goes by a simple, three-letter name: I-R-S.

The best types of accountants help you set-up financial systems that track and record the information necessary to report accurately and on time to Uncle Sam. They can also help you watch and manage your pennies in a way that sets you up for long-term financial health.

Without this critical team player, you’ll NEVER make it to the championships (read: make a profit and have a long term business).

Next, you need a “fixer…” A reliable insurance agent is the Olivia Pope every small business owner must have on the dream team.

It’s a scary fact that MOST small businesses do not have adequate business insurance. Many small or home-based businesses don’t have coverage at all, and that is a risk not worth taking.

I recall a time when I lost my laptop in an airport heading to a business conference out of state. From client personal information to my business financials and pictures of my kids – EVERYTHING was on that laptop. I was a worried mess.

I was relieved when my agent told me my equipment was covered under my insurance policy and that he’d also gone ahead and added a data breach rider to my policy at a low cost… Thank God.

A great insurance agent helps to ensure all of your small business bases are covered in the event of a nightmare. And believe me, there WILL come a time when you hope and pray you are insured for something.

You’ve got your LeBron and your Olivia, now you need good ole Saul Goodman, small business attorney extraordinaire.

Trademarks, contracts and sales policies, oh my! A good attorney (without the drug deals, of course) makes it so your small business’ best interests are always represented.

Having an attorney to generate your business contracts, protect your business name and to just bounce legal questions off of is priceless, indeed. While you need not have an attorney on retainer, per se (hey, I’m the bootstrapping queen), it’s good to form a relationship with an attorney who can be in the know about you and your business and who can be your go-to counsel when the need arises.

A dream team just isn’t solid without Huck, the tech guru

You need a techie for times when you don’t know what you don’t (or shouldn’t) know.

When I was in the early development phases of my online community, I would spend entire 8-hour days in WordPress programming hell. From researching and selecting plugins to tweaking code and installing themes to the general “my website just isn’t working” calls to my website host, I lost so many hours working on the technical side of my small business I found myself dreaming about the admin panel of my site at night.

It was bad.

Then I discovered WPCurve… (Insert angelic chorus, here)

Companies like WPCurve will “mind” your WordPress website and handle ALL the technical issues on your behalf. You pay them a monthly fee in exchange for a designated number of service hours and the promise of technical peace of mind.

If you’re a small business owner, you need to get a service like this – stat.

A powerful team like this needs a leader – someone to guide the ship.

So, for the next role, I recommend Vince Lombardi, a small business coach.

All-star players in every sport have great coaches. And all great business owners – large or small – need a business coach for encouragement, support, ideas, best practices and everything in between.

Even Oprah has a business coach, so…

One of my former small businesses was a brick-and-mortar integrated marketing communications firm. We had it all – great ideas, awesome clients, superior service, a solid team.

We also had the debt and small business drama to match and we ended up with a miserable failing mess.

Guess who was missing from the team? A coach…

A business coach is someone helping you mind the ship in a 50,000-ft view sort of way. Your coach helps with strategic planning and long-range goals. They tell you what obstacles to watch out for and they are there to help you think through and overcome challenges. They’re intimate with your business but they aren’t IN your business on a day-to-day basis, so they see things you don’t see.

I stand by the fact that if we’d had a small business coach in the aforementioned business things would’ve worked out in a much different and more favorable manner for us.

So there you have it, folks – an accountant, an attorney, an insurance agent, a small business coach, and a tech guru – five of the best positions for the seats on your small business bus.

And while I stand firmly by this list of the MOST critical members of the “Entrepreneur Dream Team,” I’ll add one more position that has proven priceless for increasing my business productivity and adding some camaraderie to my otherwise lonely work day.

Lloyd, the virtual assistant.

Oh c’mon! Who better than this “Entourage” ride-or-die-super-advocate to have on your dream team?

All facetiousness aside – a good virtual assistant can be a lifesaver for a busy small business owner. This is a bootstrapper’s ideal team member.

My virtual assistant has become such an asset to my small business, I cannot imagine my day without her. She handles everything from social media to scheduling and vendor/affiliate management. She’s become a trusted partner and she’s an awesome online business companion I can bounce ideas off of during the day.

A virtual assistant is a cost-effective team member based remotely away from your office. That means all the help you need without the added overhead costs of space, furniture, equipment and benefits.

The right assistant can handle tasks that increases your productivity by taking common administrative must-dos off your plate with minimal impact to your bottom line.

To wrap things up, I FIRMLY believe in this dream team because I have first-hand experience operating without them. As a small business owner, the “dream team” has proven itself effective to my business operations time and time again. This small, but impactful group of people will help make your small business viable, sustainable and positioned for its long-term future.

Images: “business, technology, internet and networking concept – businessman pressing dream team button on virtual screens/


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Keianna Rae Harrison

Keianna Rae Harrison

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