Breaking
EASYPOST reaches a reported $1.5B valuation YC S13 accepted on the second try 100+ carriers behind one RESTful API BILLIONS of packages shipped 200+ countries and territories served “A great idea is wonderful, but scaling it takes a village” FROM a weekend side project to a unicorn
Founder · Engineer · CEO

Jarrett Streebin

He looked at the way FedEx, UPS, and USPS made developers integrate shipping and decided it should take one line of code instead of a week of pain.

Jarrett Streebin, founder and CEO of EasyPost Jarrett Streebin: makes shipping boring on purpose.

A clean line of code where there used to be a nightmare

Jarrett Streebin runs EasyPost, the company that quietly sits between online stores and the carriers that move their packages. When a merchant prints a label, verifies an address, buys insurance, or tracks a parcel across more than a hundred carriers, there is a decent chance EasyPost's API is doing the work in the background. The company serves more than 200 countries, employs over 450 people, and has shipped billions of packages. It has been reported at a $1.5 billion valuation.

The pitch that started it was four words: a Stripe for shipping. Before EasyPost, developers who wanted to add postage to an app had to wrestle with the SOAP and XML systems that the big carriers offered - the kind of APIs most engineers would call a nightmare to work with. Streebin's bet was that a single, clean RESTful interface could hide all of that and give any small retailer the kind of shipping muscle people associated with Amazon.

He did not arrive at this from inside the logistics world. He found the problem the way a lot of good founders do: by bumping into it on the weekend and being unable to let it go.

A great idea is wonderful, but activating and scaling it takes a village. - Jarrett Streebin
Origin

The side project that wouldn't let go

Before EasyPost, Streebin worked as an analyst - time spent at The 451 Group and a family office, looking at companies from the investor's side of the table. On weekends he built things. One of those weekend builds kept running into the same wall: the carriers' shipping integrations were ancient and miserable. FedEx, UPS, and USPS each had their own labyrinth, and stitching them together was a job nobody wanted.

That irritation became the company. Streebin, originally from Oklahoma and a UC Berkeley graduate, started EasyPost in 2012 with a simple premise - shipping should be a developer feature, not a developer ordeal. By June 2013 the company had raised $850,000 and was doubling transactions every month, with SV Angel, CrunchFund, and Y Combinator backing the early bet.

Before the company

THE 451 GROUP · FAMILY OFFICE

Streebin worked as a venture analyst, evaluating other people's startups - then went and built one out of a problem he kept hitting on the weekend.

The Second Try

Rejected by Y Combinator. Back in six months later.

EasyPost applied to Y Combinator for the Winter batch and got an interview. The team felt good about it - they had a strong Show HN, SV Angel money, solid references. They were confident. They did not get in.

Six months later they applied for the Summer 2013 class with a different story to tell. They had gone from signups to a working product with paying customers. This time they got in. Streebin later wrote up the lesson on the company blog: the YC interview is not really an interview at all.

It's not an interview, it's a presentation - you present your case piece by piece and answer questions as they come. - Jarrett Streebin, on the YC interview
The Arc

From weekend hack to shipping infrastructure

PRE-2012

The analyst years

Works at The 451 Group and a family office; tinkers with shipping integrations on the weekend and finds the carriers' APIs unbearable.

2012

EasyPost is born

Founds EasyPost to build the first RESTful API for shipping - a clean interface over a messy industry.

2013

YC and $850K

Gets into Y Combinator's Summer batch on the second attempt and raises $850K from YC, SV Angel, and CrunchFund while doubling transactions monthly.

2015

Buying the name

The team lands the premium easypost.com domain and writes up how they pulled it off.

2021

Series B

Raises a $25M round as the API quietly becomes plumbing for tens of thousands of businesses.

2022

Unicorn

EasyPost is reported at a $1.5 billion valuation.

TODAY

At scale

450+ employees, 200+ countries, billions of packages - with Streebin still at the helm.

The Operator

Early mornings, golf, and a $100 bookstore habit

RHYTHM

Up early, asleep early

An early riser who exercises and reads the news before work, and guards his sleep enough to go to bed early - unusual discipline for a startup CEO.

FUEL

Reads constantly

Can drop $100+ in a single bookstore run, keeps stacks going, and happily abandons a book that doesn't grab him. Recent reads: Chip War.

OFF HOURS

Golf and backgammon

Unwinds over golf and backgammon, and counts Killers of the Flower Moon among recent favorites.

METHOD

Procrastinator, reformed

Self-aware about a natural pull toward procrastination - and a deliberate habit of tackling the hard task first anyway.

CREED

It takes a village

Believes execution and scaling beat lone-genius ideas: the company exists to serve customers and make their businesses run better.

ADVICE

Bold, open-minded

Be bold yet open-minded, stay close to friends despite the calendar, and if you make money, give generously while you can.

The best infrastructure is the kind you never notice

There is something fitting about a company whose entire job is to disappear. A shopper clicks buy and never thinks about which carrier moved the box, how the rate was chosen, or whether the address was real. A developer adds shipping in an afternoon instead of a quarter. The whole point of EasyPost is that nobody has to think about it - which is exactly why most people have never heard of the company moving billions of their packages.

Streebin's instinct was to take an ugly, fragmented corner of commerce and make it feel like a single button. That is harder than it sounds, and it is the kind of work that only pays off if you are patient enough to sit in the plumbing for a decade. He has been.

In His Orbit

The EasyPost universe

Shipping API Stripe for shipping RESTful Multi-carrier Address verification Label printing Package tracking Y Combinator S13 SV Angel CrunchFund UC Berkeley Lehi, Utah Developer tools E-commerce logistics
Marginalia

Facts worth the postage

01

Pitched EasyPost as “a Stripe for shipping” before that analogy became standard startup shorthand.

02

Originally from Oklahoma; headed west to UC Berkeley.

03

The company chronicled the saga of buying the premium easypost.com domain in a public blog post.

04

Plays golf and backgammon - and reads enough to abandon books mid-chapter without guilt.

05

Got into Y Combinator only after a first rejection, then turned the experience into a how-to guide for other founders.

06

Guards his sleep and goes to bed early - a quiet rebellion against startup all-nighter culture.

The Rolodex

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