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Life and Leadership Lessons I Learned From My Military Experience: “The best approach is to take a healthy dose of humility, admit you have a lot to learn, and lean on the skill set of your team.” with Karl Siebrecht and Marco Dehry

One lesson I learned then that I carry with me today is that you’ll often find yourself leading something that you haven’t done before. On that ship, I inherited a team and there were a couple of senior people with 20+ years of experience. On paper, they reported to me, but I quickly learned the […]


One lesson I learned then that I carry with me today is that you’ll often find yourself leading something that you haven’t done before. On that ship, I inherited a team and there were a couple of senior people with 20+ years of experience. On paper, they reported to me, but I quickly learned the value of partnering with them to learn from their experiences. It can be tempting to come into a job with a lot of pride and try to prove yourself. In reality, the best approach is to take a healthy dose of humility, admit you have a lot to learn, and lean on the skill set of your team. If you don’t, you jeopardize your reputation and the mission. The people who know more than you can tell when you don’t know what you’re doing in about five seconds, so if you try to fake it you can damage credibility very quickly.

I had the pleasure of interviewing Karl Siebrecht, FLEXE Co-Founder and CEO. Karl is a seasoned technology executive, with leadership experience in both startups and large, global corporations. Prior to co-founding FLEXE, Karl was CEO of AdReady, a Seattle-based advertising technology company. He is also a founding Board member of EnergySavvy, a SaaS-based solution for energy efficiency management. Previously, Karl was President of Atlas at aQuantive where he helped lead the sale to Microsoft for $6.6B. Earlier in his career, he was a Manager at Bain & Company in Boston and a Special Ops Diving Officer in the US Navy. He holds an MBA from Dartmouth’s Tuck School of Business and a BA in Economics from Duke.


Thank you so much for joining us Karl. Can you tell us a bit about your childhood “backstory”?

I grew up in Houston, Texas, surrounded by a great community of supportive friends and family. My childhood was a pretty typical suburban upbringing. I cared a lot about school and always tried to be a good student. I had a deep love for college basketball (a passion that I still carry today, go Blue Devils!)

I remember one of my friends had an older brother who went to Dartmouth — so I started to hear stories about life on the east coast. I quickly developed a keen interest in traveling and exploring other places across the country and around the world.

With the passion seeded, I decided to apply for out-of-state colleges and found myself attending Duke University to study economics on an ROTC scholarship. I was motivated by the opportunity to serve my country in the military and by the prospect of traveling the world after graduation.

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

Today I live in Seattle, Washington, and I am the Co-Founder and CEO of FLEXE. My Co-Founders, Francis Duong and Edmond Yue, and I started this business in 2013 when we identified a huge problem, and opportunity, in the $1.5 trillion logistics industry.

Put simply, historically warehousing is expensive burdened by high fixed costs, yet business can be unpredictable. Companies large and small alike are challenged by the lack of structural flexibility in warehousing — throughout a given year, a business may need more capacity and services, and other times could be left with too much. Traditional warehouse leasing models are predicated on long-term leases, typically ranging from five-to-seven years. In order to sign a multi-year lease, businesses must ensure they secure enough capacity for projected growth, seasonal peaks, and other variables within their business that affect inventory levels.

If a company forecasts they will grow 20 percent over five years, they will need to plan ahead and lease a warehouse that can accommodate their growth by the end of year five. However, that means that in year one the company will only occupy half of their leased warehouse space — and that’s assuming the company’s original forecast was correct. If the business grows slower than anticipated, the company is left with excess warehouse capacity, and if the business quickly scales, the company may run out of space.

We believed there was a better way. So we founded FLEXE and created the on-demand warehousing category. We established the largest open network of warehouses and connected it through a single technology platform so goods owners of all sizes can easily access more than 1,000 warehouses across North America. This has led some of the largest retailers in the world and fastest-growing eCommerce companies to depend on FLEXE as a long-term, strategic partner. Today, we work with brands like Walmart, Ace Hardware, hims, and Lull among others.

Likewise, the largest and leading warehouse providers, such as Geodis and Iron Mountain, partner with FLEXE to capitalize on their current capacity through our technology platform. We facilitate a curated matching process between retail sellers and a set of providers that meet their projects’ criteria. Typically, different warehouses run different operations, technologies, and systems. If a company wanted to work with more than one warehouse, they would have to onboard multiple systems and integrate with disconnected, separate process. You can imagine how complicated this becomes the more warehouses you use. However, every warehouse provider that runs a FLEXE project uses our technology platform, which standardizes operations across our network of warehouses. The two-sided market we’ve created has enabled warehouse providers to drive revenue during traditionally slow seasons, and improve utilization metrics throughout the year.

There are currently 80 people on the FLEXE team, and we’re growing very rapidly. We recently moved into a new office space in the historic Seattle neighborhood, Pioneer Square, and in December Deloitte recognized us as the fastest growing company in Washington State (and 18th in all of North America).

I’m amazed to see the unique ways businesses use our platform. For example,

● Our client Lull Mattresses deployed FLEXE’s eCommerce fulfillment solution to support their rapidly growing business and offer customers a competitive delivery promise. They needed a more agile, flexible approach to their fulfillment strategy that allowed for dropshipping (when a product is sold through a store, but the inventory is not kept in stock and is instead shipped directly to the consumer.) As a result, Lull reduced their delivery times by 51 percent and delivery costs by 30 percent. (Read more about our work with Lull here.)

● We also helped our client Ace Hardware with their Hurricane Heroes initiative. Ace used warehouses in the FLEXE network and our technology platform to pre-position emergency-response materials to support communities impacted by hurricanes. As a result, last year Ace was prepared to support regions affected by Hurricanes Florence and Michael. They were able to get shipments to the affected areas in fewer than 24 hours — including transit time — on a Saturday. (Read more about our work with Ace here.)

Ace and Lull are just two of many companies that have discovered how to evolve their logistics strategy to meet the diverse range of different situations with on-demand warehousing.

Can you tell us a bit about your military background?

During my college admission process, I was offered scholarships to both the Army and Navy ROTC programs. Both seemed great. When I realized that the Navy had bases in places like California, Rhode Island, and Hawaii, it became a no-brainer to me. I accepted the Navy scholarship.

As part of the ROTC process, when senior year rolled around, I needed to decide which part of the Navy I wanted to serve in. Through training every summer, all midshipmen spend time with Naval aviation, submarines, surface ships, and the Marine Corps to get exposure and a feel for each. Ultimately, I decided to apply for the Diving Program — it sounded exciting and challenging, and I also heard from folks that it was a small, close-knit team, which appealed to me. Because the team was so small and the program was highly sought-after, the application process was quite competitive — which also appealed to me. Ultimately, I was accepted into the program and that’s how I became a Navy Diver.

I served in the Navy for four years, including one extended deployment overseas. I learned a lot and grew a lot during that period of my life. Thinking back on it now, I’ve come to realize I was laying the foundation for my future path as a serial entrepreneur, CEO, and founder.

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

My first assignment after dive school was on a submarine rescue ship called the USS Pigeon (fierce name, right?) in San Diego. I was the officer in charge of the auxiliary engineering department, meaning all the engineering systems on the ship except for the main engines. I had studied how water pumps, auxiliary power units, and plumbing systems worked, but I had zero hands-on experience. I showed up on day one and people were looking to me to lead. I was expected to be an expert when I simply was not. Sure, I had the academic knowledge, but we all know that’s nothing compared to “on-the-job” experience.

One lesson I learned then that I carry with me today is that you’ll often find yourself leading something that you haven’t done before. On that ship, I inherited a team and there were a couple of senior people with 20+ years of experience. On paper, they reported to me, but I quickly learned the value of partnering with them to learn from their experiences. It can be tempting to come into a job with a lot of pride and try to prove yourself. In reality, the best approach is to take a healthy dose of humility, admit you have a lot to learn, and lean on the skill set of your team. If you don’t, you jeopardize your reputation and the mission. The people who know more than you can tell when you don’t know what you’re doing in about five seconds, so if you try to fake it you can damage credibility very quickly.

In my early days as an entrepreneur, and even now 20+ years into my career, I try to remember that there will always be more to learn and more experienced people to learn from.

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. Based on that story, how would you define what a “hero” is? Can you explain? Does a person need to be facing a life or death situation to do something heroic or to be called a hero?

To me, a hero is a person that does something courageous, based on principles they believe in, for the benefit of others — whether that means strangers, friends, families, or a broader team. Those are the core ingredients: risk, based on principle, and selflessness for the benefit of others. I absolutely believe heroism can exist outside life-or-death situations.

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. It bears repeating: remember to practice humility and ask for help (reference USS Pigeon story)

2. Details Matter. On another mission, our team was tasked with repairing part of a generator. In this situation, I learned quickly that it’s impossible to make sound, strategic decisions without a concrete understanding of how things actually work. Investing the time and energy to learn is just as important as asking for help. For example, when someone was rebuilding a generator, I remember how time-intensive it was to learn the actual mechanics of the generator and see how all the pieces work together.

The same is true in my job today. When you think about starting a business, by definition your team is tiny. You have just a few people, so everyone is involved in everything. Each team member must understand the mechanics of “the generator” because there isn’t anyone else there to understand it for you. However, as the company grows, the details can quickly become lost as different people take on disparate, specialized responsibilities. Suddenly, individuals can become quite removed from various parts of the business — product experts can become less familiar with what the end-customer needs and the sales team can become disconnected from how the product their selling works. This is a natural growing pain. However, your challenge as a leader is to help keep everyone informed and emphasize the importance of the details.

At FLEXE, we recently launched a new program called “FLEXEperts” for this exact reason. FLEXEperts is an internal learning program in which every member of our team can stay up to date with what’s happening throughout the company during small-group, interactive sessions. At the end of the day, this degree of knowledge share is not going to happen organically, so it’s important to proactively champion the details.

3. Lead from the front. I learned this during my time in the Navy, and it’s still something I strive to practice every day. Leading from the front means that if you are going to ask people to do things, as a leader, you need to act in a way that demonstrates you are also doing those same things. Act in the same way you expect those around you to act. This phrase always makes me think about the classic war movie where there’s a cowardly officer in the back of the ranks calling for the troops to charge the enemy. That’s a more extreme example, but it represents something that is very real in business today. If you’re going to ask things of people, whether that’s to make something a priority, expedite a process, or behave in a certain way, you have to model those same things. Lead from the front so people have an example to follow. Otherwise, you probably won’t get the result you want and you’ll lose credibility in the process.

Take our new FLEXEperts initiative, for example. If I stood up as CEO and claimed this is a top priority for everyone in the company, and then I didn’t sign up or go to the classes myself, what does that say about the initiative? More importantly, what does that say about me? Everyone is busy, including me. If I don’t prioritize and intentionally make the time to become a certified FLEXEpert alongside my team, quite frankly, why should anybody else?

4. Set expectations and don’t overly rely on individual heroism.

Regardless of the circumstance, everyone in business can do a better job of setting expectations. This is particularly critical as you progress in your career or grow a company because you will find yourself delegating more responsibility more often.

I learned this lesson during my fourth year in the Navy when I was deployed on a ship in the Persian Gulf. I had recently earned my qualification to serve as the Officer of the Deck (OOD), a critical watchstanding position that is earned through hard work and significant apprenticeship, and comes with a huge responsibility. Essentially, an OOD is in charge of overseeing the entire ship and safely navigating it toward the end destination during a particular watch. I was assigned to serve at midwatch (the shift from midnight until 4 AM) and it just so happens we were transiting through the Strait of Malacca that night. This particular Strait is the single busiest waterway on the planet. It’s about a 500-mile stretch of waterway where the Indian Ocean meets the Pacific Ocean. More than 100,000 vessels pass through it each year, so traffic is dense. Heading into my OOD shift I remember the captain of the ship approached me and asked how I was feeling. I could tell he was assessing me. I didn’t want to come across as nervous and I also didn’t want to appear arrogant, so I remember saying something along the lines of “I feel confident, but I recognize this is a high-risk situation.” I’ll never forget what the captain said to me — “Don’t be a hero.” He went on to explain that he had the confidence I could rise to the occasion and keep the ship safe and on track. However, he set clear expectations with me that I was to call him should anything go awry. To me, this was a model of great leadership.

In business, it’s important to explicitly state our expectations and confirm that our team understands us. The person communicating is responsible for ensuring the listener understands, not the other way around. The second moral of this story is to not be a hero — or at least, don’t always default to trying to be the hero. This relates to my earlier point about humility. In a high-pressure situation when the ship and crew are on the line, err on the side of calling the captain and asking for help. Often, I think people are afraid of appearing weak or acknowledging they don’t know how to handle something. Have the courage and self-awareness to put the safety of the ship and the success of the team before your pride.

5. Trust, deeply. We throw around the word “trust” a lot, and I’ve come to find it takes a very special kind of trust to build a team that can function at its highest potential.

At Navy Dive School, my first open water dive was on a bright, calm day about 20 miles off the coast of Florida. It was a surface-supplied dive, so I was wearing a helmet connected to an air supply hose from the ship and heavy boots to make walking around on the bottom easy. The dive crew was responsible for lowering me down into the water what’s called a “stage”, and hoisting me back up at the end. I got in the water, they started to lower me down, and suddenly they stopped when I was just below the surface. The helmet is wired with communications so divers can constantly talk with the supervisor on the surface. Through the commotion, I heard someone say that there was a hammerhead shark swimming around the boat. Needless to say, I started looking around, but didn’t see anything. Then, without another word the crew continued to lower me down. With my head on a swivel, I completed the tasks I was meant to do and returned to the surface when I was done. What I learned in that moment is to trust the people on my team. Though anxious while suspended in the water with a shark nearby, I had to be confident they were doing what was best to keep me safe. I had to stay calm and let go a little.

Since then, I’ve encountered my fair share of “hammerhead-shark” situations in life. The solution? Trust. But trust isn’t typically given, it is earned. So, as a leader you need to be thoughtful about how to nurture an environment where trust can be built and intentional about building this as cornerstone of your culture. If done well, this deep trust among a leadership team and across the broader organization can help drive truly differentiating results.

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

Absolutely. My military experience greatly influenced how I think about building strong teams. Almost always, the difference between success and failure is how well your team functions together. This depends on several key ingredients:

● Clear direction. Communicating a clear strategy while setting expectations with your team.

● Strong alignment. Again, the burden of understanding is on the communicator, not the listener. Reiterate the direction and strategy of the business. If you don’t continue to revisit the core purpose and direction of the company, people naturally will become misaligned, especially as your business grows.

● Accountability. With the strategy established, and reiterated, the next important step to a well-functioning team is defining roles and responsibilities with associated mechanisms to manage for accountability. If we say we’re going to do something, we need to do it. We won’t always accomplish everything, but if we don’t hold ourselves accountable by owning and learning why something didn’t get done, our efficacy as a team will crumble.

● Prioritize your people. Remember to play an active role in helping individuals develop to their full potential. Investing in people, training, and mentoring helps team effectiveness and drives positive morale. People want to learn, they want to be challenged, and they want to grow.

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?

This is a delicate subject. I believe everyone’s experience is different, so I prefer not to weigh in.

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

FLEXE is my exciting project. I can hardly put into words how much I’ve enjoyed building this company and watching the team grow. I truly believe we’re providing value to both the sellers and the providers on both sides of our marketplace.

One of the greatest joys as a founder and CEO is to take the time to sit back and observe our team and how people work together. FLEXE is building an innovative new solution in a relatively traditional and risk-averse industry. It has been difficult at times, but it’s also incredibly rewarding. Having the conviction to push forward based on the belief we could build a better solution led us to create a culture of resilience and perseverance. This strong foundation combined with our focus on solving our customers’ challenges has been essential to our momentum and success.

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

It’s very important to continue to be a student. People all around us have different experiences and different perspectives, and this diversity can be extremely valuable if we appreciate it and create the conditions to tap into it. Remain curious so you can learn from the people around you.

I believe reading is also incredibly important to continue broadening your perspective. Ben Horowitz’s book “The Hard Thing About Hard Things” is a fantastic read, particularly if you’re thinking about founding a startup. One of his statements that really resonated with me is that when you’re in the early days of building something, nobody cares. Startups are a dime a dozen. Smart entrepreneurs are a dime a dozen. It is incredibly hard work, and at times you can feel very isolated, because until you are able to start creating value for customers, you’re not having an impact and no one has ever heard of you or your company’s brand. Truly, nobody cares. It’s all-consuming and it makes you realize that it will never be as important to someone else as it is to you. That’s normal. That’s how it should be. Truthfully, if you need someone else to constantly validate your idea and your accomplishments, you should probably reevaluate what you’re doing.

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

I’m being redundant here, but the key is really all about the team — hiring, leading, and creating the cultural conditions required for great teams to thrive.

None of us is 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 dad. He worked in marketing and spent most of his career at consumer products companies and agencies. He had two mantras that I’ll never forget:

1. Work hard. My dad was always the first person in the office. Far beyond generating output, this also sets a tone and example for the organization. There are a lot of other ingredients to success, but if you aren’t working hard, the rest won’t matter.

2. He had this sign on his wall that read, “Assume nothing, otherwise you’ll make an ‘ass’ out of ‘u’ and ‘me’”. In business today, we talk about the importance of being data-driven in our decision making. It’s about doing the work, gathering the facts, and grounding our strategies in what we know to be fact. I chuckle when I think about that sign now because it’s sort of the old-school way of saying “let’s be data-driven”.

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

I am deeply invested in the Seattle community. In addition to being the Co-Founder and CEO of FLEXE, I’m a founding board member of EnergySavvy. Prior to that, I was the CEO of AdReady and President of the Atlas division of aQuantive, helping lead the company’s sale to Microsoft for $6.6B.

Outside of business, I’m also an avid supporter of Disability Rights Washington, a private non-profit organization that protects the rights of people with disabilities statewide, Global Partnerships, a fantastic impact-investing organization based here in Seattle, and Duke Engage, an immersive service program for Duke students.

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

I’m very curious about how we can organize distributed technology talent and capacity to more effectively address some of the world’s largest socio-economic, environmental, and community-health challenges.

I think there’s an opportunity to create a marketplace of sorts that can organize and concentrate available resources like talented engineers or product developers who already have full-time jobs, but who would enjoy contributing to social good initiatives if given the opportunity to be able to do it in a high-impact way. Through this marketplace, individuals could opt in to an existing cause or initiative that already has momentum and organization. I think of it kind of like a distributed “Google 20%” program. I can quickly imagine many challenges with trying to make this real, but I do think that there’s an opportunity to rethink how best to organize and distribute our human technology resources more efficiently to drive greater positive social impact.

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

“Better is possible. It does not take genius. It takes diligence. It takes moral clarity. It takes ingenuity. And above all, it takes a willingness to try.” — Atul Gawande

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)

Atul Gawande. He is brilliant, humble, strategic and pragmatic. He’s a surgeon, author, and public health researcher. I highly recommend his book The Checklist Manifesto, which sounds like the most boring thing ever, but it’s pragmatic genius!

Thank you for joining us!

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