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Derek Porter of Gateway Proven Strategies: “Don’t hesitate to ask for help”

Don’t hesitate to ask for help. Asking for help when you know you need it is a sign of strength, not weakness. The weakness is not being able to swallow your pride and utilize resources and people around you that can help you and your business. In this interview series, we are exploring the subject […]

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Don’t hesitate to ask for help. Asking for help when you know you need it is a sign of strength, not weakness. The weakness is not being able to swallow your pride and utilize resources and people around you that can help you and your business.


In this interview series, we are exploring the subject of dealing with crisis and how to adapt and overcome. The context of this series is the physical and financial fallout that resulted from the COVID 19 pandemic. Crisis management is one characteristic that many successful leaders share in common, and in many cases it is the most important trait necessary to survive and thrive in today’s complex market.

I had the pleasure of interviewing Derek Porter.

Derek Porter is a U.S. Special Ops Marine, turned serial entrepreneur, and cannabis business expert specializing in security consulting, licensing, investments, marketing, and technology. Derek has established himself as a successful serial entrepreneur in the space having started and exited two multi-million dollar cannabis companies in five years’ time, Security Grade Protective Services (now Helix Cannabis Security) and Cannabis Security Experts. He was recently appointed as the Chief of Staff for the world-class canna-business consulting firm Gateway Proven Strategies (GPS), where he utilizes his breadth of experience to help uplift new startups in the space.


Thank you so much for doing this with us! Before we dig in, our readers would love to get to know you a bit. Can you tell us a bit about your childhood “backstory”?

I was born in Flint, Michigan. We only lived there until I was 10 when my old man got a job in construction in Colorado, so off we went to the Denver metro area. I graduated from an alternative school known as D.C. Oakes High School, then set off to the United States Marine Corps.

And what are you doing today? Can you share a story that exemplifies the unique work that you are doing?

I am the proud Chief of Staff of comprehensive cannabis consulting company Gateway Proven Strategies. I am also a serial entrepreneur and investor in six different organizations, four of which are in either Hemp or Cannabis. As a nod to my military background, I co-founded Dynamic Warriors, a veteran owned CBD and wellness brand that provides warriors, from combat veterans to cancer survivors, with broad spectrum, homeopathic supplements. I am also proud to sit on the Board of Directors of Sierra Delta, an organization that empowers veterans with access to approved dog training that provides purpose, innovation and community through the love of dogs.

Can you tell us a bit about your military background?

I was a part of a Special Operations unit called F.A.S.T. company (Fleet Antiterrorism Security Team). I did two combat deployments to Iraq between 2004 to 2006. I also had a brief stint with a private military.

Can you share the most interesting story that you experienced during your military career? What “take away” did you learn from that story?

I learned to have a deep respect for my enemy. War and business do not mix well and equal more blood shed. As a businessman and someone who was once a part of the “war-machine”, I have worked for a private military and I learned that those two universes struggle to co-exist. There can be lives lost due to budgetary constraints and a major lack of support for combat elements in war when operating privately and for the purposes of profit. It can really make you sick to see the devastating loss. I also find that I’m more for diplomacy now than most hippies.

We are interested in fleshing out what a hero is. Did you experience or hear about a story of heroism, during your military experience? Can you share that story with us? Feel free to be as elaborate as you’d like.

Based on that story, how would you define what a “hero” is? Can you explain?

Do you think your experience in the military helped prepare you for business or leadership? Can you explain?

It certainly helps. In the military, you learn how to sharpen any natural leadership skills you may have. You learn how to delegate down and maintain troop welfare, or in the business sense, employee welfare.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I have a few mentors in this business that have really looked out for me along the way: Tripp Keber, Founder and Former CEO of Dixie Brands, and Charles Feldmann, Founder and CEO of Gateway Proven Strategies. They have both been my advisors in a couple different operations and have pointed out some unique opportunities for me.

Ok, thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out how to survive and thrive in crisis. How would you define a crisis?

I think a crisis has a different meaning for each person. When in a personal crisis, I think it comes down to the individual circumstances. As far as crises in business, I think you thrive by being prepared. We live in a very reactive society versus a proactive society. I think it’s imperative to try and prepare for potential disastrous circumstances that are relevant to your business.

Before a crisis strikes, what should business owners and leaders think about and how should they plan?

Preparation is key. Do some scenario planning like in competitive intelligence. War game out some possible negative scenarios and cultivate some realistic ways to either thrive or crawl your way out.

There are opportunities to make the best of every situation and it’s usually based on how you frame it. In your opinion or experience, what’s the first thing people should do when they first realize they are in a crisis situation? What should they do next?

You nailed it with this question. It’s making the best out of every situation. Use your imagination and prepare for realistic negative outcomes (the keyword there being realistic) and role play out the best way to get out of it.

What do you believe are the characteristics or traits needed to survive a crisis?

Adaptability, level headedness, resourcefulness, and perseverance.

When you think of those traits, which person comes to mind? Can you explain why you chose that person?

Did you have a time in your life where you had one of your greatest setbacks, but you bounced back from it stronger than ever? Can you share that story with us?

With my first security company, Security Grade Protective Services, we ultimately stopped providing guard services and switched to surveillance. We thought we would be laying off many guards, however, I decided to pivot and spend the extra money to re-train our guards to become surveillance operators. Ultimately, they made more money as well because surveillance is a much higher margin. We took a needed transition that was going to be potentially harmful to our employees and turned it into a very positive outcome.

Here is the main question of our discussion. Crises not only have the potential to jeopardize and infiltrate your work, but they also threaten your emotional stability and relationships. Based on your military experience, what are 5 steps that someone can take to survive and thrive in these situations? Please share a story or an example for each.

Sadly, in some crisis scenarios, you may lose some people or assets. Sometimes it’s unavoidable. However, your reaction to it is something you can control. Taking the best approach towards a crisis and not shying away from it should always be your mindset. I would also share these traits:

  1. Prepare for a likely or potential crisis beforehand.
  2. Maintain a strong mental mindset, really put effort in to think positive.
  3. Innovate or die. As you build your business so that you can easily adjust, adapt and overcome.
  4. Don’t hesitate to ask for help. Asking for help when you know you need it is a sign of strength, not weakness. The weakness is not being able to swallow your pride and utilize resources and people around you that can help you and your business.
  5. There will be casualties and things may not pan out as well as you think. Be mentally prepared for that.

Ok. We are nearly done. You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Take a stand in the world you live in, even if it’s not the popular opinion. If you know what you are doing is right wholeheartedly and the consensus around you is of the same opinion, then take that stand and push to change the community’s perspective. Traitors turned patriots have done this time and time again.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them 🙂

Leonardo Dicaprio seems to be very humble and is a talented guy and he spends big bucks on advocating for change, such as combating climate change. I dig that quiet cool about him. I’d love to smoke a cigar and sip some whiskey with him.

How can our readers follow you online?

You can visit my website at derekporter.me

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