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Life and Leadership Lessons I Learned In The Military: “Raise Your Hand & Speak Up.” with Jason Anderson and Marco Dehry

Raise Your Hand & Speak Up. In Malcolm Gladwell’s book Outliers he talks about an Asian airline pilot who allowed a plan to crash out of fear of speaking up to his superiors. Again, this is a drastic analogy, but I see this daily in my office. Employees are sometimes scared to speak up and […]


Raise Your Hand & Speak Up. In Malcolm Gladwell’s book Outliers he talks about an Asian airline pilot who allowed a plan to crash out of fear of speaking up to his superiors. Again, this is a drastic analogy, but I see this daily in my office. Employees are sometimes scared to speak up and ask questions to managers, managers are afraid to speak up to C-Level executives and ask questions. I had a flight chief that use to start meetings by asking “who is the dumbest person in the room?” His question wasn’t meant to embarrass you, but it was meant to understand who shouldn’t be working on life and death missions, aircraft or machinery. People would raise their hand and say “I’ve never worked on that system before,” and then would be paired with the most knowledgeable vs left to go on their own and do more harm than good.

I had the pleasure of interviewing Jason Anderson of Venture.


Thank you so much for doing this with us! Can you tell us a bit about your childhood “backstory”?

I’m the youngest of (9) total siblings (full, ½ & step), born on October 16, 1982 in a 1,000 square foot Duplex in Rochester, NY. My home was in a rough part of town. My father was born in 1938 in Valdosta, GA and fled the south for New York during the civil rights movement. He started as a janitor at the bus company and kept that job his entire life. My father is now a pastor and is one of the kindest people you will ever meet, But with (9) kids, dozens of grandkids there was seldom enough of him to go around. He took (2) other jobs to put me through private catholic school after seeing how my siblings turned out in the public school system. My parents divorced, my father then married my stepmother (whom I now consider to be my mom) when I was 10 and we moved to Atlanta. I haven’t seen my real mother since that time (26 years) and have only spoken to her twice.

My closest brother (7 years older) got involved with a local gang and was almost killed by them and spent a few weeks in the hospital my freshman year. Due to the suspects attending my school I had to be put into a different school district. At 15 years old I was working to support myself, bought a car, had gold teeth, tattoos and was headed down the wrong path. Seeing several friends drop out of school, get involved with the wrong crowd and end up in jail or even worse get killed, I knew I had to find a better way. The music group, Outkast, became a massive, influential part of my life, as they rapped about things, places and aspects I never heard of. I attempted to try my hand at college, but after visiting campuses I couldn’t bear being a broke college student trying to make ends meet. I knew that would lead to failure. So, I enrolled myself in the United States Air Force at 17 years old and forced my parents to sign to allow me to do so. In less than 60 days after high school I was in basic training.

At 17, I had devised a 35 year plan. Step one-retire in 20 years from the US Air Force, then get another government job and retire from that in 15 years when I was 52.

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

Today, I have traveled the world and I have been married for 11 years. I completed my Associates, Bachelors, Masters and an Ivy League certificate and have been featured on the cover of Realtor Magazine, the Dallas Business Journal, and TLC’s My First Home and honored as a Forbes 30 under 30 recipient. I’m currently the President of the fastest growing Coworking Space Franchise Venture X.

Can you tell us a bit about your military background?

The Air Force was my first real job and saved my life. I arrived at San Antonio’s airport for basic training at Lackland AFB in June 2000 having lived in a very narrow perspective world. Basic training was the first true experience I had with structured discipline, workouts, diets or really anything for that matter and it was a shock. I was enrolled as an avionic sensor maintenance tech working on million dollar equipment on airplanes. After my six weeks of basic training, I spent another six months in San Antonio for training school. I was then shipped off to Sheppard AFB for more training in far north Texas. It’s still an inside joke amongst friends upon finding out that I was being stationed at RAF Mildenhall UK, I thought it was a dorm at the University of Kentucky. Keep in mind this is before anyone I knew had a computer, no smart phones or internet. I arrived in RAF Mildenhall, England Easter weekend 2001, and it was like another world with different weather, buildings, accents, and cars on the wrong side of the road. Most importantly, now at 18 years old I could drink legally. The first five months were an absolute blast, and I was convinced I would never leave England. Then almost five months to the day after becoming active duty, America was attacked on September 11, 2001.

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

The lack of education = shoveling wet sand. Once I got out of basic training, it only took me a few days to really grasp the legal segregation of enlisted vs officers. I was at first taken aback when someone not much older than me would walk by or in a room and we (as enlisted) had to stand and salute them. It didn’t end there, I found out they averaged three to four times the pay as I did as well. They also had better jobs.

I asked my first flight chief “why do they deserve so much respect?” The answer was unbelievably simple — they went to college. After the terrorist attacks on 9/11 and I was deployed, I spent the first few weeks shoveling wet sand into sand bags for bunkers in the cold and wet British country side. I literally did this for weeks, 10–12 hours a day. Had I gone to college I could have been flying planes, managing troops, and strategizing. Instead I was shoveling wet sand into sand bags, waiting for the next dump truck to come and dump more sand. As a side note, I got absolutely ripped. So my take away was, nowhere is the delineation between education and lack of more prevalent than in the US Military. I swore that when I got out, I would never be in that position again. So, I guess you can say I over compensated by getting three degrees and an Ivy League Certification.

I’m 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.

Having no context of what to expect in a war time, I was blown away seeing the Special Forces parachute into our base waiting to deploy to the front lines. We would literally watch troops parachute down, land and start pitching tents. We would drive out, pick them up and they would shower in our gym locker rooms. They were so calm, cool and collected and then it dawned on me, they were deploying to the front-line in 24–48 hours and facing possible death. It put every decision I’ve ever made or will have to make into perspective. These guys were just like me, probably playing Grand Theft Auto on base just a few weeks ago, saw the news on 9/11 and within days were mentally prepared for war. Seeing someone who can fully grasp the full severity of their decision when its life or death, and still go confidently into action is in my world a “Hero.” I’ve watched almost every documentary on Vietnam and World War II and seeing so many brave souls run into battlefields is something inconceivable for most to understand, but these heroes did just that, and for what? The thought and support of our American freedoms, which most people are too scared to take advantage of. This thought process has made major decisions in my life much easier, when put into these contexts.

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

The literal definition when you Google “Hero” is a person who is admired or idealized for courage, outstanding achievements, or noble qualities. I would add that most of these men and women will never be known by you and I or be a household name. It’s a truly selfless act for the greater good. They don’t make millions of dollars like athletes and aren’t trying to be rich and famous. Having the guts to put your life on the line for people and ideas fits perfectly into this definition for me.

Does a person need to be facing a life and death situation to do something heroic or to be called a hero?

I don’t believe they do, but this is certainly a driving force like no other! Venture X is proud to support America’s military. We provide a 10 percent discount off the franchise fee for our country’s heroes.

Based on your military experience, can you share with our readers 5 Leadership or Life Lessons that you learned from your experience”? (Please share a story or example for each.)

1. “Knowledge without action is vanity, and action without knowledge is insanity” — Imam Ghazali. The military puts you into tech school, and once you’re done you immediately go to work doing that job you learned the skills for. This is almost non-existent in the real-world college setting for most people. You will spend four years learning things you will never use or do. Be sure to use what you learn immediately.

2. Everyone should go through boot camp. Having someone shave your head, take all your earthly possessions and throw you in a room with 60 other guys to eat, sleep, shower and live, changes you. While that may be extreme for most people to go through 6–12 weeks of military basic training it doesn’t mean you can’t have your own version. If you’ve never accomplished something like basic training or don’t have plans on going to the military, I suggest you sign up for a triathlon, marathon, or even a Tough Mudder event. There’s something about getting out there and doing these types of things and pushing your mental and physical limits that make you grow as a person.

3. You fail your way to success. If you haven’t watched World War II in HD on Netflix I highly recommend that you do. Not only is it my opinion the most significant event in modern history, you quickly realize, that no one really had anything better than an educated guess of what to do next. It was trial and error the entire war on all sides to the path to victory. Not to say millions of people have to die like WWII, but look around at your current situations. Are you failing enough? If not, it’s probably because you’re not trying enough.

4. Travel the World. I’ve met so many adults that have never left their home state or country, and I truly feel bad for them. Having the opportunity to live in England when I was 18 changed my world in so many ways. I was forced to adapt in ways inconceivable to those that have never lived abroad. I was able to travel around to so many parts of Europe and experience so many different cultures. You simply can’t comprehend how different your perspective of the world becomes the more you travel.

5. Raise Your Hand & Speak Up. In Malcolm Gladwell’s book Outliers he talks about an Asian airline pilot who allowed a plan to crash out of fear of speaking up to his superiors. Again, this is a drastic analogy, but I see this daily in my office. Employees are sometimes scared to speak up and ask questions to managers, managers are afraid to speak up to C-Level executives and ask questions. I had a flight chief that use to start meetings by asking “who is the dumbest person in the room?” His question wasn’t meant to embarrass you, but it was meant to understand who shouldn’t be working on life and death missions, aircraft or machinery. People would raise their hand and say “I’ve never worked on that system before,” and then would be paired with the most knowledgeable vs left to go on their own and do more harm than good.

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

Amazingly so! After going through basic training and having someone spit in your face, you’re more prepared for office politics. Also, almost every business is running like the military. You have ranking members who have been around for a long time, alongside small special forces teams that are out there getting missions done as silent heroes daily. You also have the hurry up and wait mentality, and ever so often just like sometimes government things don’t make sense, but you have to move forward anyway.

As you know, some people are scarred for life by their experience in the military. Did you struggle after your deployment was over? What have you done to adjust and thrive in civilian life that others may want to emulate?

I was fortunate being in the military that I was never put into direct combat. But I have friends that were and having known them since they were 17 or 18, I can 100 percent say that they were never the same. There are just some things that you can’t forget, good or bad once you have been through them. While I don’t feel anyone in the modern (post-9/11) military has had to face circumstances like existed in Vietnam and WWII, It’s still evident that as humans you become desensitized to things. I’ve simply never let my foot of the gas pedal since getting out the military and my life has been non-stop in a positive way. I also try to meditate and do yoga every morning which has helped immensely as well. For those with issues, I recommend seeking help from both a psychiatrist to make sense of the past and a life coach to help make sense of the future.

Are you working on any exciting new projects now? How do you think that will help people?

I’m very passionate about my job and company Venture X. I believe coworking in its essence is the future of the worlds shared economy, and this brings us all one step closer. Coworking is going to be the hub, driving the spokes of the entrepreneurial world over the next decade.

What advice would you give to other leaders to help their team to thrive?

Ask each employee you have if they were able to create their dream job what would it be. You will get some great answers, and if possible, why not give them a shot doing that job within your organization. Some people may not even mention anything about their current job and not be relative to your business at all. Doesn’t mean you let them go, but at least now you know.

What advice would you give to other leaders about the best way to manage a large team?

Organize, organize & organize more your organization chart, make it clear and public for everyone to see and understand.

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 about that?

My boss, friend and mentor Ray Titus, the founder of Signarama and United Franchise Group. We are from completely different worlds/possibly planets, but yet still seem to find a mutually beneficial work/business relationship. He always has a positive perspective and seems to find the opportunity in everything as well.

How have you used your success to bring goodness to the world?

This is a category I constantly struggle with. I’ve worked with dozens or maybe hundreds of friends, clients & colleagues in growing themselves or business in some manner. I have a goal to create a resource to help millions accomplish the dream of becoming a “Multi-Thousandaire.” Most American households are living paycheck to paycheck and need a path to middle class before they can dream of being a millionaire. I want to help people achieve that goal and on to bigger and better things.

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. 🙂

True life support. Growing up the youngest of nine, neither of my parents finished grade school. They did their best and we never went without, but I realized how little about real life things I really knew. So many people go through the world today and will never have the capacity to hire a financial planner, life coach, CPA and there needs to be a real life support system for the other 99 percent of the world. My goal is to create this for everyone’s benefit to help with financial, legal, and education based literacy. You can really be empowered with knowledge.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“I’m Not Afraid of Dying, I’m Afraid of Not Trying” — Jay Z. This quote sums up my urban philosophy of the world.

Some of the biggest names in Business, VC funding, Sports, and Entertainment 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 if we tag them 🙂

One of my biggest living idols is Sir Richard Branson. I’ve reached out to him dozens of times with no response. His capacity to take seemingly endless ideas or businesses and turn them into successful billion dollar companies isn’t what makes him unique, as Steve Jobs and Elon Musk have done that as well. What really gets me is how cool, calm and collected he can be while doing all those things. His personality is spot on to who and how I would be as a billionaire.

Thank you for joining us!

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