“Focus on your sphere of influence. Whether you like it or not, who you are and what you do impacts those around you. Imagine if we framed all our decisions in the context of “how will this impact those around me” and everyone you’re connected with did the same. I’d venture to say that the world would be a much different place. No one would disagree with this statement or concept. However, the challenge is that it goes against the grain of our inherently selfish nature. So, let me boil it down to one simple statement: In All Things, Consider Others First.”

I had the pleasure of interviewing Trevor Outman, the President and Co-Founder of Shipware, a San Diego based consulting and technology firm that provides expertise aimed at helping shippers negotiate improvements to their carrier contract terms & pricing. Prior to graduating business school with his MBA, Mr. Outman proudly served his country in the US Army as a forward observation and reconnaissance specialist.

Thank you so much for doing this with us! What is your “backstory”?

I’ll never forget the humble beginnings of Shipware. Our first office location was a bachelor pad garage. I was living with four of my close college friends and, without asking for permission, commandeered a corner of the garage and set up a makeshift office using folding card tables.

One of my roommates was responsible for coding v1 of Shipware’s software technology. We built a SaaS based solution that would audit carrier invoices for high volume shippers. The technology identified and recovered refunds from billing errors and service failures, resulting in 1–7% savings. The quick pitch was: if we can’t reduce your weekly invoice then don’t pay us; otherwise, we simply ask for a percentage of the found money we recover. I lived in the dusty corner of that garage grinding through call lists and sending out hundreds of emails every day.

We were one of the first to market with this technology-based solution, and the market responded in kind. We grew a healthy book of business and quickly moved into an office space. Soon, clients started asking for help negotiating competitive discounts, rates, and terms with the carriers. I leveraged my experience, from auditing and analyzing hundreds of carrier pricing programs, to deliver 10–30% savings to them.

I became passionate about helping shippers reduce their shipping costs because most are unknowingly and unnecessarily overpaying. We became advocates for shippers and developed non-intrusive solutions that ultimately leveled the playing field between them and their carriers.

Can you share the most interesting story that happened to you since you started your career?

We’re all at the Del Mar horse races for a team event. I didn’t see any security around the track — the type of personnel you’d see at a baseball or football game to prevent people from stepping onto the field (or racetrack in this case). Apparently, they were non-existent at the Del Mar horse races.


I pointed out this interesting observation to some of my teammates. A few minutes pass and, the next thing I know, one of my sales reps is walking down the stairs towards the track. I thought he was bluffing. There’s no way he would hop the railing. It’s way too risky!

Sure enough, he gets to the railing, looks around, quickly hops it and is on the Del Mar racetrack! He runs to the middle, lays down on his back, and begins to do a perfect snow-angel in the dirt. No one could believe what they were witnessing, including myself. Everyone’s jaws dropped and was either belly laughing or nervously laughing, wondering what would happen next. Once the crowd finished cheering and his moment of fame was realized, he ran off and later reunited with our crew. Note: security does exist there. Do not attempt! He had to explain himself to security and, fortunately, that was all. He was lucky though. True story. We are going back this year . . . if they let us in. 

How do you synchronize large teams to effectively work together?

Everything rises and falls on leadership. Effective leaders demonstrate ownership and operate with influence. Starting with ownership, when a team member makes a mistake, the leader assumes responsibility as if it’s his/her own misstep. Secondly, effective leaders earn the trust and respect of their team members to influence direction and motivate accordingly.

I’ve noticed great leaders shed their title and focus on the hearts and minds of the team. I have yet to see a leader do this well with more than 10 team members. Building trust and earning the right to continually influence others takes a significant time investment. In my opinion, leaders see diminishing returns with teams over 10. Therefore, for a large team to effectively work together, multiple leaders should be placed throughout the organization, ensuring every individual has a direct and close connection with their manager/leader. The team of leaders should align, meaning wholehearted belief in and commitment to the same vision and direction. In this environment, momentum builds, a healthy culture and sub-culture develop, objectives are tackled, and results are achieved and celebrated collectively.

What advice would you give to other CEOs or founders to help their employees to thrive?

I’ve found that it’s human nature for people to assign greater importance to some roles. But, In a high functioning organization, no one should feel superior or inferior. Individuals that carry themselves with a sense of superiority are toxic and debilitating to an organization. The same is true of someone that feels inferior. Every team member needs to understand that their role, same as any other role, is mission-critical to the success of the organization’s goal(s).

It’s the leader’s responsibility to ensure this level of understanding is deeply ingrained within all team members. To encourage this, shift the paradigm of the oganizational chart. I’ve worked at inverting the organizational chart in my heart and mind, which changed my perspective and approach. Flipping the org chart upside down creates the most compelling form of leadership, servant leadership. I don’t believe the purpose of my employees is to serve me; rather, my top priority is to serve them. Even while I lead from the front the function of the position is to serve the organization by forging a clear path ahead for my teammates.

Serving team members can take on many forms. However, I would suggest it’s most critical for me to ensure they are empowered to perform at the highest level possible. Serving the employees generates a results-based culture which inherently creates very satisfied clients. Satisfied clients translate to more revenue and more revenue translates to more resources invested back in to the company. A rising tide raises all boats.

Most times when people quit their jobs they actually “quit their managers”. What are your thoughts on retaining talent today?

Effective leadership, at its core, is influence. True leadership cannot be awarded, appointed, or assigned by title; it comes from influence, and that cannot be mandated. It must be earned.

Employees will quit managers that don’t build trust and respect. Employees will quit managers that don’t take a genuine interest in their lives. Employees will quit managers that don’t earn their right to influence.

I believe employees who aren’t known and individually appreciated by their managers will not feel fulfilled by their jobs. Appreciation and recognition are easy to dispense when successful results are apparent. However, before success is achieved, effort needs to be applied and this effort can often result in failures and mistakes. Remembering to recognize and appreciate effort by making it the sole reason for the conversation will help motivate a team member to continue striving for positive results.

No one wants to do a bad job. Everyone wants to do well and win. No one just lands on success or in the winner’s circle; the path is littered with failures and mistakes. The key is to fail forward, learn, and get better from yesterday’s lesson. Therefore, if we as leaders can positively encourage effort, even amid mistakes, then we’re sending the right message. Encouraging effort will lead to the joy of rewarding results and eventually the celebration of a career.

Based on your personal experience, what are the “5 Things You Need To Know To Successfully Manage a Team”. (Please share a story or example for each, Ideally an example from your experience)

In my opinion, the 5 fundamentals every team leader should apply to develop a high functioning team are:

Trust & Respect. Commitment. Honest Communication. Accountability. Measure Results.

  1. Trust & Respect — This isn’t just the foundation to effective teams; I would suggest it’s the foundation to any healthy relationship. Take either trust or respect away from any relationship and it is no different than removing a wheel from race car. It may be able to awkwardly move down the track, but as soon as you try to build momentum, a wreck is certain.
  2. Commitment — It’s most important to understand each team member’s personal “WHY”to garner earnest commitment. In other words, what intrinsically motivates them to pursue mountain-top success? What motivates them to keep pushing when the path or job becomes arduous? As a leader, once you understand the individual’s WHY, you can motivate and earn commitment. At that point, it’s a matter of connecting the fulfillment of their WHY to the overarching team objective. Essentially, the individual is committing to themself, their vision, and their WHY with the understanding that, once the team’s mission is accomplished, they’ll be closer to fulfilling their own vision/WHY. Everyone on the team will have different reasons to commit, but once unique motivations are tapped, the team will naturally gel because they’re committed to the same objective or goal.
  3. Honest Communication — Honest communication is commitment to transparency and requires vulnerability. Leaders go first to promote this level of communication throughout the team. I firmly believe that when honest communication is coupled with #1 above, there is literally no interpersonal problem that can’t be resolved (which doesn’t always mean agreement). Communicating through a disagreement with trust and respect is almost a guaranteed path to conflict resolution. We’ve all been in situations where the tone or words used were disrespectful or when trust was absent. When was the outcome ever positive? Never. I would suggest a breakdown in any relationship can be traced back to either a lack of trust, respect, or honest communication.
  4. Accountability — Accountability acts as the guardrails to ensure the team’s mission is accomplished. Once the path to success is defined, team leaders should work with each team member to align on the necessary steps needed to be successful. Those steps are measures of success. Regular evaluations will determine whether the individual and team are on track to achieve their goal(s).
  5. Measure Results — Allow room to continually refine and improve by consistently measuring results. Fell short of the goal? Ask why, evaluate, and redefine the path ahead. Overshot the goal? Ask why, evaluate, and redefine the path ahead. There are many paths to the top of the mountain. Given the fact that each team member is persistent and committed, measuring results will notify you when a change of course is necessary.

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. 🙂

This may be a politician-type response, but I believe it’s a realistic response. Focus on your sphere of influence. Whether you like it or not, who you are and what you do impacts those around you. Imagine if we framed all our decisions in the context of “how will this impact those around me” and everyone you’re connected with did the same. I’d venture to say that the world would be a much different place. No one would disagree with this statement or concept. However, the challenge is that it goes against the grain of our inherently selfish nature. So, let me boil it down to one simple statement: In All Things, Consider Others First.

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

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat. — Theodore Roosevelt

This was a foundational quote from a leadership program I participated in during my college years that I would go on to help lead and facilitate. The essence of this quote helped shape who I am and how I approach life and business.

In business, I love strategy and am fulfilled by the challenge of navigating uncharted waters. Strategy determines direction, so while critical, it doesn’t take you across the finish line. Ideas, like strategy, won’t come to life on their own. Almost everyone has a business idea; implementing strategy or executing an idea is where the rubber meets the road.

It’s the same as walking into the proverbial arena. It means you’re willing to come to terms with the possibility of defeat. Few take these bold and courageous steps. The grit and determination to be the “man in the arena” has motivated me my entire life. In business and in life the path of least resistance leads away from the arena. Life has a way of creating a current that pulls us on to this path, all we need to do is pick up our feet and it will wash us away. Instead, choose to swim upstream and then walk yourself into the arena. I’ll do my best to see you there.