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Heroes Among Us: “I found that humility (leaving my ego and former status as an officer at the door), being genuine, and keeping an appropriate sense of humor REALLY helped with integrating back into the civilian workforce.” With Drew Kellerman

While it took about a year to adjust to civilian life after leaving the service, I never served in combat, so didn’t face the many, serious obstacles that combat veterans often do. That said, I found that humility (leaving my ego and former status as an officer at the door), being genuine, open and helpful, […]


While it took about a year to adjust to civilian life after leaving the service, I never served in combat, so didn’t face the many, serious obstacles that combat veterans often do. That said, I found that humility (leaving my ego and former status as an officer at the door), being genuine, open and helpful, and keeping an appropriate sense of humor REALLY helped with integrating back into the civilian workforce.


I had the pleasure to interview Drew Kellerman. As founder of Phase 2 Wealth Advisors and a seasoned retirement planner, Drew is committed to helping his clients make thoughtful and educated financial decisions. Drew holds the Series 65 Securities License and the Washington State License for Life, Health, and Long-term Care Insurance. In addition, Drew is a member of The Society of Financial Awareness (SOFA), a national, 501(c)(3) non-profit public benefit corporation, which provides free and unbiased financial education. Prior to starting his financial career in the late 1990’s, Drew served our country as an Airborne Ranger Infantry Officer in the US Army. Drew and his family have resided in Gig Harbor for 12 years, where he enjoys hiking and surfing. On the weekends you might spot Drew refereeing youth soccer matches and spending time with his wife of 25 years and their two teenage children.


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

I grew up in Hawaii, graduating from Punahou High School (8 years behind President Obama’s class). As a 13-year-old, I knew I wanted to be a soldier, even though both my dad and grandfather were career investment professionals in Honolulu. So, I attended the University of Colorado, Boulder on an Army ROTC scholarship. Upon graduating, I was commissioned as a junior officer just as Operations Desert Shield and Desert Storm were wrapping up (1991). A few years later, I watched as my Mom lost nearly half of her life’s savings by following poor investment advice, just as she was entering retirement. I was deeply moved by the unnecessary and long-term devastation this caused her. This inspired me to become a professional retirement planner and investment advisor once I left the Army.

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

I founded Phase 2 Wealth Advisors LLC, an independent financial advisory firm. Our company’s focus is entirely on those who are in or nearing retirement — Phase 2 of their financial lives — and guiding them to make thoughtful and educated decisions with their life’s savings. Our goal is to help them thrive in retirement and not go through my Mom’s experience. Over the years, we have advised countless couples and individuals on how to navigate the financial component of this huge life transition. At first, clients are often taken aback by our approach. We spend all of our time and effort designing the right plan for them before ever discussing investment options and recommendations. In time, they come to realize that the plan drives the investment recommendations, not the other way around.

Can you tell us a bit about your military background?

In hindsight, it would seem that the Finance Corps would have been my calling, but I chose a different route. I was honored to serve as an Airborne and Ranger qualified infantry officer in the 25th Infantry Division (Light). My primary job was to lead soldiers into combat, should the orders come down to deploy. As it was, my unit never saw combat, but we got to travel to many parts of the world on training missions. After several years of service, I realized that I was longing to be a civilian again and was honorably discharged from the Army. This was a few years before the attacks on 9/11 which changed everything for those who had continued to serve.

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

The unit I served in had to be ready to deploy anywhere in the world into a combat environment with 18 hours’ notice. While we ran practice drills for this many times, we got the call one Sunday morning at 2 AM to get ready to go, and by every measure, it was a real deployment. It wasn’t until the next day when we were in the air and on our way to our destination that we learned that it was also a drill; we were headed to a week-long, life-fire training exercise. Up until that point, though, we all thought we were headed into a combat zone. During those hours there was plenty of time for reflection. Was I ready to lead troops into battle? How would I react under fire? Would I set a good example for my soldiers? Had I prepared them for what lay ahead? The takeaway from this was that there are times in life where you genuinely have to be ready and rise to the tasks before you. If you haven’t prepared properly, you will not be able to fake it and muddle though. There are no “time outs.” It was black and white — you either succeed or you fail. In that case, failure could mean death or, worse, dishonor.

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.

Easily the most heroic act I witnessed was when an otherwise unremarkable soldier saved one of his buddies from drowning during a nighttime, tactical river crossing. The unlucky fellow had come unhooked from the rope we were using to cross the swollen, fast-moving river and he was pulled under by the weight of his equipment. Without hesitation, the heroic soldier jumped in after him, even though he himself wasn’t a strong swimmer. He was able to grab the drowning fellow and lift him enough to get his head above water while the rest of us mounted a rescue party to pull them both from the river. Most of us couldn’t believe this guy had risked his life the way he did. He didn’t seem the heroic type before this incident. When asked, he said he was really scared, but wasn’t going to let his buddy drown without at least trying to help.

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

I would say a hero is someone — anyone — who overcomes their fear to perform a selfless act, even if it means putting themselves a great risk.

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

In my opinion, no. Standing up against strong social pressure to do the right thing is also heroic.

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. Lead by example. Anyone in a position of authority can tell you what to do. Great leaders do it first and can do it better than their subordinates. The best leaders I worked with could beat their soldiers at nearly every important task and skill.
  2. Stay calm, cool and collected when the plan falls apart and everything goes wrong. I had a great commander who always appeared relaxed even during the most intense situations. His demeanor reduced panic among his team and gave us all strength and fortitude to work our way out of whatever mess we were in.
  3. A well-trained team can accomplish far more than the sum of the individuals. There was no room in our unit for soldiers that wanted to go it alone and didn’t work well with their team. They were a huge liability to the rest of us, and soon found themselves transferred out.
  4. Focus on solutions, not the problem. The best soldiers and leaders would accept and quickly assess a given problem, and then begin looking for creative ways to overcome that problem. Anyone who whined, moaned and complained about the problem was not suited for our team. They simply got in the way and slowed us down.
  5. Be adaptable to change. Knowing how important it was to stay flexible and quickly adjust to a changing environment, we used to create scenarios that would not only force our team to adapt to change, but continuously do so as an ever-increasing rate. It became a game to see how quickly could be drop one problem-solving approach and try a different one, as necessary.

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

Absolutely! Success in business requires competence, confidence, perseverance, a mature, can-do attitude and courage, among other attributes. Also, being able to adapt quickly to a changing business environment and providing effective leadership at the right times is critical. These are all traits that are cultivated in the military.

As you know, some people are scarred for life by their experience in the military. How 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?

While it took about a year to adjust to civilian life after leaving the service, I never served in combat, so didn’t face the many, serious obstacles that combat veterans often do. That said, I found that humility (leaving my ego and former status as an officer at the door), being genuine, open and helpful, and keeping an appropriate sense of humor REALLY helped with integrating back into the civilian workforce.

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

Yes. Having just published my first book, How to Survive Thrive in Phase 2 of your Financial Life, I am thrilled to be helping our firm’s clients through the often-complex transition into retirement. The book is one of many tools we are using to help empower people to make educated financial and investment decisions as they embark on this exciting new life phase.

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

Find the right people, provide them with excellent training, tools and guidance, and align their incentives with the organization’s vision and mission. Then, get out of their way. Be ready to mentor, support and spot-check.

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

No one leader can effectively manage more than a certain number of people directly (I’m told 10–12 is the limit; 5–7 might be ideal.) So, the only way I have seen large organizations work well is with a hierarchy of trusted, subordinate leaders, each with no more than a manageable team. The military is a great example. A typical infantry organization is made up of many different levels of smaller units, each with a leader. The smallest unit is a “fire team”, consisting of a leader with 4 soldiers. A “squad” consists of 2 fire teams under a squad leader. Each “platoon” has 4–5 squads in a platoon, with a platoon leader. A “company” has 4–5 platoons, with a company commander, and a “battalion” has 4 companies with a battalion commander, etc. So, even though the battalion might have 500 soldiers, no leader has direct management over more than a handful of subordinates.

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?

There are many, many people that come to mind. If I had to pick one, though, if would be one of my high school teachers who passed away a few years ago. He was tough. He pushed us to really use our brains, to think, to analyze and produce really quality work. Then, he pushed us to make it better. He did what all great teachers do; encouraged us to achieve more than what we initially thought we were capable. He also taught martial arts after school, and we saw a different side of him; encouraging, funny, and zen-like. He had mastered several of the martial arts and used his knowledge to teach us more than the movements, he taught us that the key to a great life was self-discipline.

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

Our firm exists to help people through a very tricky life transition with many moving parts and several important decisions that have long-term ramifications. We feel that every time we help a client with a successful transition into retirement, we are helping bring good to the world, one person at a time.

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. 🙂

It seems clear that, beyond a certain point of financial wellbeing, more money does not bring more happiness. And yet, so many talented and brilliant people focus all their efforts on accumulating more money for themselves. I would love to see the energy, drive, innovation and passion that often goes into building vast, personal wealth be redirected into closing the “wealth gap” that presents such great danger to our society (and many others around the world).

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

Far better it is to dare mighty things, though checkered with failure, than to take rank with those poor and timid souls who neither enjoy much nor suffer much, for they life in that grey twilight that knows neither victory nor defeat. — Teddy Roosevelt. This was my guiding motivation for much of my youth. In today’s vernacular; Go big or go home.

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 🙂

Ray Dalio. While there are many amazing people whom I would be greatly honored to meet, Mr. Dalio is very high on my list of personal heroes. The main reason for this is that he is doing all he can to bring good to the world by sharing his accumulated knowledge and wisdom with anyone who cares to take the time to learn. He has gone to great effort and expense to create video content, books, etc. and makes them all available to the public for next to nothing.

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