Kris Coleman of Red Five: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

by Maud DeVito
Kris Coleman of Red Five: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

Being a founder, entrepreneur, or a business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur  we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Kris Coleman.

Kris Coleman is the Founder, President and CEO of Red Five. Working in both the private and public sectors throughout his 20+ year career, he has served with the Central Intelligence Agency, the Federal Bureau of Investigation, and as a former Principal with Good Harbor Consulting. An expert in bespoke security solutions for high-net-worth clients, his depth and range of experiences allows the Red Five team to specialize in high quality, proactive, and discreet security services. Kris has built a unique capability in Red Five to support clients with tailored low-profile security operations, analysis, training, and program and system design. Kris is a newly published author of the book, Raise your Resiliency.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Kris Coleman: For the past 30 plus years, I have worked in security within both private and public sectors including the Central Intelligence Agency, the Federal Bureau of Investigation, and as a former Principal with Good Harbor Consulting. I founded Red Five Security in 2004 because I wanted to take all the skills I learned in the CIA, FBI, and consulting and provide state of the art security and protective intelligence services to individuals, families, and businesses.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

Kris Coleman: When I left the government, I found that there were a number of clients – both corporate and private families – with unique needs and challenges that were not obvious to the public. Many of these corporations and private families have similar resources to small countries. So, using my CIA and FBI experience, I knew I could apply some of my skillsets to solve problems for the private families and corporations, and meet their needs.

The “Aha Moment” was that I could bring those skills in a very proactive way to help these families and corporations avoid situations before they became problems. The typical security industry is very reactive, but when you are proactive in your creation of solutions, you can provide a greater value than just reacting to bad experiences. And that is when I realized – that’s what Red Five is going to do, it’s going to proactively solve problems for families and corporations.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

Kris Coleman: I was always a self-starter. I was very fortunate to work with both the FBI and CIA and both require a specific set of skills. To succeed, you must have a lot of motivation to get into those organizations. I also have a history of people in my family starting their own companies and being successful, including my father who started a construction company. He wanted to be his own boss, drive his own opportunities, and manage the company the way he wanted. I like to think his example made its way into my genetic code.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

Kris Coleman: I grew up helping my dad with his construction company occasionally on holidays, weekends, and summers and I saw what it meant to him to build a business and how important it was to him to see a house or project completed. He had a tremendous education and was a complete self-starter. He came from very little and was the first in his family to go to college.

He had worked for engineering firms early in his career, but when he got to a certain level he said, “You know, I want to own my own destiny.” And I followed his example. Eventually, I saw what he saw, which was the ability to set your own path. You are betting on yourself, I know I am a good bet, and I’m not going to fail. Failure is not an option, so I will hire the best people that I can, and get the best clients, and do the best work we can.

What do you think makes your company stand out? Can you share a story?

Kris Coleman: First, I have to recognize my colleagues at the FBI and CIA. The sacrifices they make daily are untold and their work an important piece of where I came from and the foundation and inspiration of Red Five.

Our work extends not just to businesses, but for families and individuals too. We believe in being proactive by conducting security audits and helping families, individuals and organizations put plans in place to prevent bad things from happening to good people. Our team is comprised of experts from the Federal Bureau of Investigation, the Central Intelligence Agency, Department of Defense, Department of State, and the Secret Service.

What sets Red Five apart is responsiveness, trust that we can deliver, and following through and absolutely overdelivering for clients. We’ve had situations where clients have called us and said, “You’re the third company we’ve called and the first two can’t do it, what do you think?” And we confidently executed the work.

We respond frequently to clients that have an urgent need – for bug sweeps, for cyber breaches, for protection missions, privacy concerns, and due diligence.

Once, we took over an executive protection detail in the Los Angeles area and it was a huge endeavor. It included 60 agents over the course of 30 days, with 17 different protectees all over Southern California. The current program was not working for the client, and they called us and said, “Can you take it over tomorrow?” So, within 48 hours, we took over the program and successfully delivered a massive executive protection program. I don’t know if there are very many companies that could have done that as safely and securely as we did.

Another example, we had a client that came in and said, “We’re expanding globally, can you help us go into all these countries?” We were able to provide the client access to multiple countries, simultaneously and in a successful, secure fashion.

Our people and network make these missions happen. We are multi-mission experts, bringing expertise from a variety of disciplines. These examples show we’re responsive, we’re leveraging our experiences and we’re following through. All those things build trust.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Kris Coleman: I’m in the field of resiliency and the three keystone characteristics for a resilient leader to have are.

  • You must be honest up front, that’s number one. If you’re honest and transparent from the start, and you tell them what’s going on, then you finish the job and you never have the problem of getting up in the morning thinking, “Man, that was a bad one.” In retrospect, you know that it was tough, but you got through it and can look yourself in the mirror the next day.
  • You must be trustworthy, especially with our private families and our corporate clients. You must do what you say you’re going to do, follow through. Whatever the challenges are, you finish smartly, and you do what you said you were going to do.
  • Treat your employees the way you would want to be treated. That goes a long way.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

Kris Coleman: I don’t have an example of any poor advice I received, but I do have pieces of advice I was given multiple times. When I went off on my own there were two pieces of advice people gave me. Don’t go cheap on accountants or attorneys, because both of those will end you if they fail. The other one was, you’re never going to work harder than you do when you work for yourself – and that is absolutely true

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

Kris Coleman: Establishing a strong corporate culture will help companies survive tough times, especially if the culture includes concepts such as resiliency and preparedness. Culture needs to be determined, nurtured, developed, and reinforced when it’s right. This means looking beyond just putting beer and ping pong tables in the break room, but creating a culture where employees can thrive even in difficult times.

Leaders can setup company activities that reinforce resilient behaviors and help establish a sustainable culture. This can include scavenger hunts, hiking or outdoor activities, fitness challenges, team competitions, or participating in philanthropic events for local charities.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

Kris Coleman: Whether you are a minority-owned government contractor, a CEO of a woman-owned corporation, or the founder of a startup, you must set the tone for resilience, readiness, and preparedness. If you are resilient, then your team and businesses will follow. To set the path forward, a leader cannot be a clueless visionary that does not give resiliency a second thought. Resilience must be rooted in your thinking, and leaders should focus on the difficult side of business operations in addition to your innovative aspirations.

Can you help articulate why doing that is essential today?

Kris Coleman: Companies without a resilient leader are left to rely on the second in command or the line staff to establish the plan for preparedness. Companies that do not have a strong COO or Managing Partner to execute the vision of the founder struggle, as their decisions might be based in fantasy. For a company to thrive and survive, business leaders must be aware of risks or external threats looming.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

Kris Coleman: I see many CEOs that are not properly prepared for unexpected crises. When you start a business, you need to think ahead and put plans in place for financial, environmental and relational hardship, along with what you will do if there’s a burglary or security breach. A Business Preparedness Audit helps address the key areas you should be paying attention to as your company develops, matures, and moves through its life cycle. By taking the time for this process, you can gain insight into where you may have blind spots or shortcomings.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

Kris Coleman: As an entrepreneur, you are solely responsible for your business and employees, taking on additional stress that those with a “regular job” don’t have. This adversity can present itself in many ways – shortage of cash, decreased demand for your services, natural disaster, heavy competition in your industry, poor management, or any combination of the above. Realistically setting up your business with preparedness plans can help you in handling the inevitable lows and enjoy the highs.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

Kris Coleman: We always get excited when we create tremendous value for clients. When a client asks us to take on a very special project that’s going to help them achieve their goals, and we know we’ve got the skills to tackle that, it reminds us why we got into this business. The tasks are often difficult, often in another language, on another continent and usually in a dangerous environment and it’s got to be done yesterday. When we deliver, and the client says, “I can’t believe you found that information,” Or “We can’t believe you provided that to us so we can protect our employees.” Or “You saved us from that bad, unwanted incident.” That is a win and that is a high five moment across our team.

For example, we did a child custody exchange across Europe, and it was an incredible effort and rewarding experience. It involved boats, helicopters, decoy motorcades, tactics and deception, making it a huge moment for our team when the client was safe on the airplane and on their way home, crossing back into US airspace. That is a “high” moment.

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

Kris Coleman: On the other side, you never want to let anybody down. In some instances, clients are looking for certain information that’s important to a lawsuit or it’s important to a specific strategic action and they’re looking for the data and they hope it’s there. But the reality is, hope isn’t a strategy and if there isn’t a real, achievable goal, that can be frustrating. If the data doesn’t exist or it can’t be found, it’s not for lack of trying on our end – we will put in a ton of effort and use every possible legal resource we have, but you don’t always get to win.

Based on your experience can you tell us what you did to bounce back?

Kris Coleman: We are honest with the client and tell them, “Here are the 17 things we tried. We even created new paths to success, to try above and beyond what you paid for.” I always feel good knowing we went above and beyond even when we don’t get to the finish line for the client. We try to manage expectations up front, if there is a set back and we can’t get where we wanted to go, we take the lessons learned and implement them moving forward. Most importantly, you don’t repeat efforts that don’t create results.

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

Kris Coleman: To remain resilient through the ups and downs of entrepreneurship I advise entrepreneurs to apply the Five Pillars of Resiliency, which are; awareness, mindset, fitness, skills and relationships.

  • REAL Awareness ensures you have a firm grasp on reality and accurate information.
  • A positive REAL Mindset helps lead you toward success and helps you grow.
  • REAL Fitness is key to your ability to bounce back both physically and emotionally.
  • Both basic and sophisticated REAL skills are needed as an entrepreneur to combat threats.
  • REAL Relationships are an important pillar because you must know your trusted circle, use their inputs to survive, and you must nurture those relationships to thrive.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

Kris Coleman: Resiliency is the ability to bounce back from adversity; the capacity to recover quickly from difficulties; or, the capability to adjust easily to misfortune or change. Resilience and strength are not the same thing, as resilience embodies a higher level of understanding, growth, and experience.

Resiliency is the ability to adapt and overcome obstacles and achieve a positive outcome. Even if you believe that you are adequately prepared to take on the challenges ahead, it is important to truly reflect on your coping abilities, leadership assets and mix in a good bit of self-honesty. There are many ways for individuals to learn and practice resilience skills. But make no mistake, building those skills takes commitment and hard work.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

Kris Coleman: I watched a childhood friend go through cancer. Her fight with the illness was an influence on my life and reinforced the need for resilience. She was a fighter but it was tough to see her go from a healthy remission back into the fight for her life. In her memory now, looking back, she provided some inputs for me on how to keep things in perspective and be grateful. The same thing happened recently to an adult friend of mine. Those survivors are living models of resiliency.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

Kris Coleman: Yes, going as far back to high school, I acquired nickname of “Coolhand” because I approached poor situations with a steady hand and a cool head. Throughout my career I continue to approach situations clinically – without bias or emotion – to handle them in a positive way that results in success. This allows me to put emotions, anxiety, and fear aside that may negatively impact outcomes.

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

Kris Coleman: As a leader, you set the tone for your organization. If you use negative words and phrases, this will rub off on the culture and mentality of your team. Changing your thinking to a more positive tone is more constructive and will reduce drama among coworkers and business partners.

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

Kris Coleman: I have two…the first is

“The only thing necessary for the triumph of evil is for good men to do nothing.” – Edmond Burke

I have had that quote on my radar for most of my professional career. I think it rings true today and will for the foreseeable future. Anyone, regardless of gender, race, etc. can make a difference by pushing back on evil. Do something to push back for the better and it helps. We cannot sit idly by and let bad things happen.

And…my second is more recent.

“If you are not the calm, then you are the chaos.”  – Jeff Banman,
Founder of MindsetRadio

This is one of my favorite quotes because a good mindset, a REAL mindset, allows me to separate the noise from what’s important, it allows me to clearly see what needs to be done to achieve my goals. It allows me to constructively ignore those that are trying to compete for my attention, that may lead to poor decisions, or incomplete information.

How can our readers further follow you online?

Kris Coleman: To learn more about resiliency and to develop REAL skills, readers can check out my book, Raise Your Resiliency found on Amazon. Readers can also find more about Red Five and REAL Experiences at

This was very inspiring. Thank you so much for the time you spent with
this. We wish you continued success and good health!

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