9 Personalities you’ll meet as an Entrepreneur.

Written by Dallas McLaughlin

Published: June 30, 2013

It’s no secret that I’ve been an entrepreneur for longer than I’ve been able to spell the word (It’s harder than you think). If I wasn’t Beckett in hand hustling neighbors for their sports cards, or going door-to-door with candy bars, I was most likely hiding somewhere coming up with my next great idea. Or so I thought.
For the last year I’ve officially been grinding away as a self-employed entrepreneur… or as the “nose in the air” entrepreneurs would say, I graduated from a WANTrepreneur, to an entrepreneur.
In doing so, I’ve relied heavily on a network of similar minded people. When you don’t have the comfort of a paycheck every two weeks, it’s necessary to flip every stone you find. You never know which one might have gold under it.
With that mentality, I’ve met A LOT of people. Some good, some bad, some evil, some helpful. It’s important to identify each of these peoples motives, intentions, how you can be of service to them, and more importantly, how they can be of service to you.

The Godfather.

  • The Godfather is our Mr. Miyagi. Full of knowledge, experience and wisdom. It’s essential that you seek one of these out and pick his/her brain. Like any true ‘trep, they’ve seen their share of ups and downs. Listen, remember, and reference what they have to tell you.
  • As influential as they can be, keep your own personal dreams and ambitions in mind. They can influence them, but don’t allow their position to tarnish them. Your dreams are just as important as theirs once were.

The Connector.

  • The Connector does just that – connects. Through some unimaginable amount of hours spent at every networking meeting under the sun, this person seems to have a database of friends, family, and services at his finger tips. If you need to find “a guy”, The Connector can do it. After spending time with a Connector you will come to realize that they seem to do nothing as a service, yet are incredibly in demand by everyone around them. It’s almost like the “chicken or the egg” paradox. The Connector is in demand because he knows everyone, and he knows everyone because everyone wants him to know them.

The Dreamer.

  • Once you show some success in business, you become a bit of a “Shark Tank” for other peoples ideas. I believe that every person deep down has a desire to develop something that fills a need in other peoples lives, and in doing so becomes self-employed. So, what you’ll have is a lot of well-meaning, ambitious people pitching their ideas to you. A lot of good ideas, some not. Then you have The Dreamer. The Dreamer has an idea so big, and so far fetched that no amount of VC under the sun can make it a reality. The #1 lesson I preach is, “If it’s going to work big, it has to work small.The Dreamer ignores this entirely. The Dreamer wants to start with 100,000 sq/ft of office space, 80 employees, a distribution warehouse, a fleet of vehicles, and more. The Dreamer’s can’t miss idea is sure to make everyone who gets in at ground level a billionaire…

The Analyst.

  • Everyone knows this guy. He’s the guy that was picked last for dodgeball. Kicked off the debate team for not being athletic enough, etc. You give this guy a set of numbers and he can give you an 8-page Excel sheet with the probability of your idea sucking before you can finish pitching it. Where his imagination and creativity lack, his data sets and eyeglass prescription thickness more than make up for. At the end of the day, his information is invaluable and under appreciated by most. I’m still not inviting him out on the town with me.

The Hero.

  • This guys ability to work incredibly hard and smart is so contagious, it acts almost like a vacuum. So much so that he sucks everyone else in the room into the same state of mind. Where the Analyst lacks, The Hero makes up. Generally young with a strong managerial approach to business. Like a field general he can lay out a game plan and inspire those around him to follow the plan and work towards a common goal. Creativity and persona are his strengths, pride and ego can be his downfall.

The Healer.

  • An entrepreneur has a series of ups and downs so drastic that a stage-3 bipolar person would consider them the crazy one. The Healer is the guiding voice. The gentle pat on the back and reassurance that “this too shall pass.” They have a way of righting the ship and getting you back out of bed on those mornings where you feel like going into hibernation and never answering another e-mail for as long as you live. Without a Healer, you’ll give up way to soon.

The Clinger.

  • The Clinger’s are those friends that seem to show up when business is good, and disappear just as fast when things go south. The Clinger’s are important because they let you know who your real friends, and real support system is. You can probably identify a few right now. Ask yourself, “Did this person genuinely care about me before this business venture? Will they care about me personally if it fails miserably?” If the answer to either of these questions is no, then you need to be careful about your time investment with this person.

The Cheerleader.

  • Also known as the “Sneezer’s”. The Cheerleader is the support system every good entrepreneur needs to have. They take your idea and spread it like a virus. They genuinely care about your success. Like any true relationship, The Cheerleader needs to be embraced and nurtured. Take care of them and they will take care of you. Give them a sense of “If I make it, WE make it.

The Cheshire Cat.

  • This personalities title comes from Lewis Carroll’s “Alice in Wonderland.” The Cheshire Cat is depicted as an intelligent yet mischievous, villainous character that sometimes helps Alice and sometimes gets her into trouble. One of its distinguishing features is that it often disappears into darkness, the last thing to be seen being its grin. This person will always be around when it is of their benefit. Be extremely careful in all dealings with this personality. At the end of the day they will find a way to gain from you all that they can steal.


It’s important to meet all of these personality types. Each and every one of them has a learning experience tied to it. Each have their positives, and most have their negatives.
It’s also important to identify which personality your co-workers, or co-entrepreneurs might see you as versus what you see yourself as.
Leave us your thoughts down in the comments. Maybe what personality types you’ve run across that I might not have included in this list, and some positives and negatives to each.

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- Dallas McLaughlin