Jarrett Streebin

Jarrett Streebin founded EasyPost in 2012 as the first RESTful API for shipping. EasyPost is on a mission to remove the technical complexities of logistics so customers can get back to growing their businesses while making shipping reliable, efficient, and affordable. Prior to founding EasyPost in 2012, he worked at The 451 Group and a family office. Mr. Streebin holds a B.A. from UC-Berkeley.

What is your typical day, and how do you make it productive?

I am an early riser. I like to work out and read the day’s news before I get started. I am in frequent contact with my team throughout the day. I enjoy golf and backgammon and reading and connecting with friends. Sleep is key, so I usually go to bed early and rise early.

How do you bring ideas to life?

We have grown to such a large size at EasyPost that I often not the one who comes up with ideas. We have a talented team many of whom originate and execute the ideas that propel the company forward and improve processes for our clients. Collaboration is an important part of our process. A great idea is wonderful, but activating and scaling it takes a village.

What’s one trend that excites you?

Now at EasyPost we are making it a reality. Goes to show you that anything is possible when focus and intentionality mix.

What is one habit that helps you be productive?

Over the years I have interacted with a lot of older people who are in terrific shape. Many say that the secret to longterm good health is to constantly keep moving. I try to emulate that advice. By nature humans like to procrastinate. I embrace the magic of doing the things that I would normally shy away from. It feels good to accomplish difficult tasks that we are naturally wired to avoid.

What advice would you give your younger self?

I am pleased with how my life turned out and the adventures I have had the privilege to enjoy. While I disdain hindsight or hypotheticals I would encourage young people to be bold but open-minded. And read constantly! It’s the best way to find new ideas.

Tell us something you believe almost nobody agrees with you.

That playing backgammon is one of the most fun mental exercises one can take part in. It’s a game of constantly evaluating your risk and I love playing with the world’s best. I can lose myself for hours playing, often losing, and thinking about all the iterations the game has in store for novice and expert players alike.

What is the one thing you repeatedly do and recommend everyone else do?

Golf! Jokes aside — staying in touch with friends. Despite running a massive company with big ambitions there hasn’t been a day in the last decade that I have not been in communication with friends. In today’s world there is no challenge in keeping in contact. A friend is never further than a text away. People like hearing from friends and I do too. Being a good gift giver is also one of life’s joys.

When you feel overwhelmed or unfocused, what do you do?

I try to recenter myself by taking on a task, usually somewhat mindless, that allows me to clear my mind and take a new perspective for when I return to that which is frustrating me.

What is one strategy that has helped you grow your business or advance in your career?

This is perhaps the easiest question of all. From the time we started we have been relentless about focusing on the needs of our customers. In some cases they clearly described what they wanted and needed and it in other instances we had to tailor solutions to issues they weren’t able to articulate. We exist to serve them and make their businesses more efficient and their clients happier. That is our North Star and even on the foggiest days we have never lost sight of that strategy.

What is one failure in your career, how did you overcome it, and what lessons did you take away from it?

Before I started EasyPost in 2012 I wasn’t sure what I wanted to do and how to map my future. A great idea came to me and along with legions of talented people we were able to build it into the thriving company that has changed e-commerce. The uncertainty if it would succeed was frightening but I had to push through.

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

I don’t have any grand business ideas that I can share but I firmly believe in the following: if you are fortunate enough to experience success and the monetary rewards that accompany it you should give most of it away — in your lifetime. It is axiomatic but true that you can’t take it with you when you pass and seeing the effect of one’s philanthropy is among the most redeeming experiences one can have.

What is one piece of software that helps you be productive? How do you use it?

Less of it! One of my favorite books of the past year is Deep Work. We’ve got plenty of software. What we need is more time for slow thinking, away from our machines, to inform our work when we do it. Reading is the perfect antidote.

What is the best $100 you recently spent?

Whenever I went to the bookstore last. I buy anything that looks interesting and always keep stacks of books ready. If I get 10 pages in and I’m bored, I’ve got plenty of alternatives.

Do you have a favorite book or podcast from which you’ve received much value?

I am an avid reader so I don’t have one particular favorite book or even genre. Recently I read Chip War, which is one of the most important tech books I’ve read. As a software entrepreneur, I always assumed hardware was merely commodity. Not at all.

What’s a movie or series you recently enjoyed and why?

Flowers of the Summer Moon – I’m from Oklahoma. And I can’t wait to see Napoleon.

Key learnings:

• A great idea is wonderful, but activating and scaling it takes a village.
• Read constantly! It’s the best way to find new ideas.
• At EasyPost, we exist to serve our customers and make their businesses more efficient and their clients happier.