Jordan Guildford on what really makes a great leader.

20 under 40


Life As A Leader can be a lonely, exhausting job in which you will never please everyone -in spite of always trying to…

One where the blame will not only fall on you, but you will stand up and accept blame willingly for all the mistakes made by others…

Your family will ache for you… You will see it on their faces… and you will still leave… 

You will come up against opposition from people who don’t want to do what you are doing; they just don’t like that you are doing it.

A job, where failure is much more likely than success.

Yet you do it willingly because you believe in your mission with every fiber of your being and will not back down.

This job is a leader of an entrepreneurial business.

I am the Founder/ CEO of a charitable organization designed to end the cycle of domestic abuse called Gems for Gems. My journey has been incredibly rewarding and equally difficult. I have needed to show courage, professionalism, be careful with my reputation always, and sacrifice most forms of balance no matter how worn out I was, all because dropping the proverbial ball could close doors now, or sometime in the future.

We have all seen articles with variations of ‘10 Traits All Great Leaders Have’ etc. However, in my experience, true leaders have more than one side of these traits. In fact, it is often a situational internal battle between Dr. Jeckle and Mr. Hyde with victor being, TBD. So why would anyone choose this? Well, it takes a certain kind of person to be willing, and above all, able, to live the life required to get a new enterprise off the ground. Some characteristics can be unflattering, but the right combination is what creates sustainability and long-term success.

The following 6 traits are the main elements that shape a leader’s experience in the entrepreneurial space; however, all have a wide range of expressions. These are conscious observations of those I have seen in myself and 100% of my peers, not peer-reviewed facts.

Each trait can be looked upon as a coin. Each coin has two sides. In leaders, each side can range anywhere from corruptive and manipulative to magnanimous and unwaveringly grounded. I believe the outcome is dictated by the individual. In successes and failures, a leader’s true nature is revealed.

Jordan Guildford

Gratitude was generated by experiencing and benefiting from the help of others as the organization grew.

Addictive personalities

We are the ones who win once at the casino and are then sure of winning again…. So, we continue to play or abstain entirely (or nearly). It is hot or cold. All or nothing.

  • Negative: Obviously, this is a dangerous and possibly highly destructive element for both professional and professional sides of one’s life.

  • Positive: The ability to see past short-term struggle to long-term success is less likely to falter when you have an addictive personality. Leaders can tap into this side of themselves and find calm even in the worst times, due to the unwavering belief in their goal. Times of strife is always temporary… even when they aren’t. The stamina this gives is unparalleled.

Lacking risk aversion: 

The ability to jump in with both feet while hoping the water isn’t frigid.

  • Negative: Your emboldened nature can have you take on far too much too fast. The best-known example of this is expanding before you have stabilized your foundation. Your entire organization is threatened when the leader decides to expand too quickly.

  • Positive: This is liberating! There is nothing you feel you can’t do. You can rally those around you to increase their own threshold for risk, but it is vital for leaders to have risk-averse people in their inner circle to balance them and blow the whistle when necessary. 


The ultimate desire is to be successful in the pursuit of your goal.

  • Negative: The goal can be the single most important thing to these leaders. The sacrifice of family and relationships is common, intended, and unintended.  

  • Positive: The competitive drive is fuel. You either want to be the best personally, have your product be the best… or both. Either way, the eighty hours a week (sometimes more) required of you isn’t possible without the drive that comes from this trait. The work ethic generated by this element is incredible.


The ability to convince others to join/support you in your goal.

  • Negative: Used poorly, this is pure manipulation which can often be utilized to use others for the leader’s gain with very little, or nothing, reciprocated. 

  • Positive: Used well, a leader can communicate very well and show others their passion, drive, and belief in their organization. This is infectious and incredibly helpful to ignite the passion in others for your cause. It is far more effective than just sharing a spreadsheet. This element can also create a large capacity for creativity and flexibility, both of which are huge attributes to an organization.


Gratitude was generated by experiencing and benefiting from the help of others as the organization grew. 

  • Negative: Extreme awareness of what others have sacrificed for you can be a significant handicap as well. It can dilute your willingness to push others to give more which in the charity world (my world), is imperative for the success of your organization. It can weaken the leader’s ability to do what the organization needs them to do in this way.

  • Positive: You are humbled constantly by your own limitations, and always have a great appreciation for the help others have given. This humility can not be faked and draws others closer to the cause thus ultimately generating more support.


Passion is the life source of an entrepreneurial leader. 

  • Negative: Passion can blind a leader. It can remove reason, caution, and inhibitions. It can create a shamelessness where grace should best serve both the leader and the organization. It often comes from painful experiences like poverty, abuse, etc., and is focused on creating the perceived opposite of that experience. 

  • Positive: It is in all 5 other traits. Without passion, none of the others are sustainable. Passion is the fire that sustains leaders’ drive when all else fails. No entrepreneurial leader is a success without passion. 

All 6 traits shape what the life of a leader looks like from both the outside and inside of an organization. They decide how the leader will be perceived, if they will be feared, if they are loved, or if they will go unnoticed. 

My experience as a leader has been forged out of what I can best describe as a calling to have a positive impact on the lives of survivors of domestic abuse. I surround myself with people who are all passionate about our focus on providing economic stability through education and empowerment for survivors. However, I have been careful to ensure those around me think differently than I do. I am highly passionate, grateful, and I certainly error on the side of being pro-risk because it doesn’t feel dangerous to me. The Board of Directors is everything I am not. There have often been six different opinions around the table and together we find the best route forward for our organization. 

The life of a leader is hard. Incredibly hard if you want to be a great one. Yet, just as with most things, you get what you put into it. I will leave you with some parting advice. 

If you do not have the 6 elements above, seriously consider not pursuing a solo mission in the entrepreneurial world. You need to be some magical combination of a survivor and a warrior, preferably with a gentle heart and an iron-clad mind. It is so hard and so worth it but only if it is a fit for you. There are so many other ways to be very successful, to make a difference, and to grow yourself. 

If you are some combination of the 6 elements above, or are partnering with someone who possesses them, and have an idea that is scalable/worthwhile, do it. You only live once and the world relies on people like you to sacrifice, innovate and create something that will make our communities and our country a better place now, and for our children.

Aspioneer Magazine, 20 under 40 issue