Passion, perseverance, and determination will always produce results, and they are contagious.

Trevor Outman, MBA, is co-founder and principal partner of Shipware, a San Diego-based shipping consulting and technology firm that has helped some of the world’s most recognizable brands reduce shipping costs an average of 25 percent through contract negotiations, complex analytics, and rate benchmarking. Leveraging years of experience analyzing volumes of parcel data and carrier contracts, Trevor is widely regarded as an expert in the parcel industry.

Shipware also analyzes and optimizes clients’ delivery network to ensure the proper utilization of carriers and transit times. Shipware’s proprietary technology will audit weekly parcel invoices to ensure carrier and contract compliance. Trevor can be reached at [email protected].

Where did the idea for Shipware come from?

Over a decade ago, e-commerce was just beginning its dynamic growth trajectory. As a recent MBA graduate, I wondered whether there was a way to help these growing e-commerce companies reduce their expenses.

After some research, I realized that the cost of shipping was a huge line item in the budget for these companies. Shortly thereafter, Shipware was born with the thought that a non-intrusive, simple solution to help companies reduce their shipping costs would be widely and readily adopted in the marketplace.

Fully committed, I quit my comfortable medical device sales job and set up shop in my garage. That was then, and now — with 20 wonderful employees — we’re on track to break $10 million in revenue next year.

What does your typical day look like, and how do you make it productive?

My typical day begins with a 4:30 a.m. alarm. I’ll grab a quick word of inspiration from the Bible. I will then check email from my phone, address anything urgent, and make my way to the gym. I get up that early to get in a two- to three-hour training session —usually something like swimming, biking, running, and maybe some weightlifting. I always have a physical challenge or race on the calendar that I’m training for — for the past few years, it’s been an IRONMAN endurance event.

After I help my wife get our two kids ready for school, I make way to the office. A productive day for me starts with checking in with my employees and then checking what meetings I have scheduled for the rest of the day. I will then scan 100+ emails to identify the ones that need my attention before the afternoon. I’ll address what I can then and there; the other emails will either be delegated as action items or flagged for follow-up later. I then block out chunks of time in my schedule to dedicate to project or analysis work and strategic business and employee development. At the end of a typical day, I will have forgotten to take a break or eat lunch, but I lock up the office with a sense of fulfillment.

How do you bring ideas to life?

Passion, perseverance, and determination will always produce results, and they are contagious. When you’re completely confident in your idea and direction and you have a “North Star” you’re marching toward, others will rally around the momentum. If I can cut through all the noise and clutter to paint the picture of what our “North Star” looks like, the right people will want to link arms and work toward results that take us closer.

What’s one trend that really excites you?

The continual growth of e-commerce and the sophistication of efficient omni-channel fulfillment.

What is one habit of yours that makes you more productive as a CEO and co-founder?

Reading a business book during the first hour of my early morning workout. This sets the tone for my day and fuels my motivation to take my business and employees to the next level.

What was the worst job you ever had, and what did you learn from it?

In high school, I worked for my uncle who was a photographer, and his best line of business was taking photos of Little League sports.

One of the most commonly ordered items was a button with a kid’s picture in it. All of these buttons had to be hand-pressed together, so he hired me. At the time, it was the most redundant task I had ever assumed. One hour legitimately felt like six. From that day forward, I was motivated to pursue higher education for fear of being relegated to pressing buttons for the rest of my life.

If you were to start again, what would you do differently?

I can’t say I would do anything differently. Even my failures put me one step closer to success. Every event seems to have had an orchestrated purpose. This is a difficult perspective to maintain in the present, but having historical context gives me greater perspective.

As a CEO and co-founder, what is the one thing you do over and over and recommend everyone else do?

Follow up and follow through in a timely manner. This is basic common sense because it communicates that you can be trusted and relied upon, which translates well internally among employees and externally with clients. However, it still baffles me how difficult it is to find this quality. When I do, it’s refreshing, and I see results.

What is one failure you’ve had as a CEO and co-founder, and how did you overcome it?

I made one bad hire — a true misread from an extensive interview process. Once I realized it wouldn’t be a good fit, I made sure the transition occurred as quickly as possible. Keeping her on board and dragging out the process would have done her a disservice, as it would have prolonged her unhappiness.

What is one business idea that you’re willing to give away to our readers?

A solution that disrupts the headhunter/recruiter marketplace is leveraging technology for screening and interviewing. Leverage technology to enable scalability and penetrate the market with bottom pricing. Market share is there to be had. 

What is the best $100 you recently spent?

It was a great team event at the Del Mar racetrack. We had a few tables, food, and drinks, but betting and losing $100 on a horse with the team makes for a very fun and worthwhile afternoon.

What software and web services do you use? What do you love about them?

I couldn’t function without Outlook. I live by my schedule and email. How did business even operate before?

What books do you recommend our community should read?

  • “Good to Great” by Jim Collins and “The Advantage” by Patrick Lencioni. 

What people have influenced your thinking and might be of interest to others?

The authors mentioned above — Collins and Lencioni. I can’t get enough.