How to Hire a Team as a New Entrepreneur | Cigars with MoneySmartGuy

How to Hire a Team As An Entrepreneur. Are you working ON your business or are you working IN your business? As entrepreneurs, we cannot get stuck in the details. Of course, the details have to be handled and squared away but that does not mean YOU have to do it all. As a new entrepreneur, salesperson or solopreneur it is easier to stay small. If you want to raise your game and get to the next level, you’ve got to create jobs! There are menial tasks for every business and an entrepreneur has to stay in the lane of growing the business. Your vision as a new entrepreneur cannot be disrupted by answering the phones every 30 sec or running errands that your staff can do!

You have great ideas and your product fits in the market well, but hiring the wrong team as an entrepreneur, can be fatal… That’s why smart entrepreneurs work ON their business instead of working IN their business. 

A lot of startups are getting failed each year because of hiring a team with sheer lack of relevant abilities and/or mismatch of skills with what the market demands. A lot of new entrepreneurs found themselves stuck in detail tasks instead of squaring it away to employees. Smart entrepreneurs delegate menial tasks to be able to stay in the lane of growing the business.   

To generate a meaningful competitive advantage in the market you have to attract and hire a high-performance team.

So here in this read, I’m going to share the counterintuitive tips to have the right leadership team for your startup or business. 


There’re a lot of speculations about how much cash-flow one should acquire before hiring an assistant. Well, you shouldn’t worry much about the cash flow instead look for the amount of admin work you need to handle.

Patrick-Det-David has a video on how to hire an assistant; so have a look at that to have an overview of all the gamesmanship of hiring your assisting staff (VIDEO). For me, the first assistant you hire would be a runner or a gopher who’ll help you in getting the right things at the right time. The second one is like a scheduler, who manages your calendar and your email. The third one is your executive assistant while the last one is your chief of staff who himself has assistants. So when you grow, they grow and as you grow you need to divide up and delegate more of your work.

If you look at my case, I have three ladies – Webley, Karen, and Carolyn. Webley and Karen were initially the runners while Carolyn does the polices and I do the licensing.

So whenever you hire a new assistant tell them “Listen, the first seven days or two weeks you’re going to be way underpaid”. Why? “because you’re learning how to trust me and I’m learning how to trust you. So just know that you’re investing a little bit of your time on me and I’m investing a bit of my money on you. So if this works out for the first seven days or fourteen days it would be a happy ending for both of us.”

Whenever I hire an assistant I tell them to be resourceful and make my life easier. They are supposed to put up fires that you don’t see because they’re anticipating. They should not just look to punch in and out but instead, they should prove themselves over 3 months to own that position.    

The best way to get the right person for the right job is to hire fast. For example, I have Alex as my staff member and I’ve also hired another guy for the same position. But the other guy initially didn’t like the fact that I hired Alex. But I tell both of them to show me their best work and Alex kept stepping up while the other guy, one day, sent me a text “it’s not for me”…

Why it’s always good to hire fast is because you’ll have them competing with each other and if one doesn’t work out, you got the other one ready to replace them.

Unique Ability Team:

As an entrepreneur, you have to identify your capacity for doing things. You have to identify things you are average at doing and the things you are excellent at doing like your unique ability. Like for me and my brand, I’m the one who has to get behind the mic and share my message. You can’t delegate anybody else to share your message or your story.

So jot down the things you need to get done and start categorizing them by highlighting as yellow, pink, and green. Green things are your unique ability that you don’t want to delegate. The other things that you’re average at doing you need to create a job for that.

For example, I am somewhat between excellent to average at doing video editing. But I have no desire to make video editing my unique ability. However, I know a man who loves doing videos and his unique ability is to edit it so I would hire that video editor instead of messing with such things myself. So imagine you have such a unique ability team and everybody’s fired up.    

Bonus Tip:

Have a good relationship with your mentor. Like for me, I always wanted to have such a relationship with Patrick in which, when I’d call him he may pick up right away like he’d want to pick up my call. I have such a relationship with him where I’ve always got good news for him whenever my number pops up on his caller ID I get picked up and the same way I always pick his calls, even if there’s an emergency.

Pay Right and Give Incentives:    

You shouldn’t be the cheapest guy in terms of paying your employees and at the same time you shouldn’t be most expensive – pay them right. In addition to that, you should create incentives for them as if they do something that surpasses your expectations offer them a bonus.

Be Competitive And Be Growing:

Giving incentives to your employees helps in creating a competitive environment in your startup. The reason why people often find me annoying is that I am always competitive. They don’t always like competitive people in their lives. But if you’re relentlessly competitive you’re always growing so be competitive! 

Maximum – Maximum Relationships:

Most employers pay just enough so that their staff doesn’t look at quitting instead of paying them right. Consequently, in such a relationship, your staff would do minimum work just enough so that they don’t get fired – a minimum-minimum relationship. But if you want your staff to give you the best they have got; you’ve to offer the best – the maximum – maximum relationship.


Which brings me to my last question, what has been your best practices in hiring a team for your business? Please share your experiences on my YouTube Channel and let’s keep the conversation going!