Episode #102: Interview with David Barrett - CEO of Expensify

Ed and I were honored to interview David Barrett, Founder and CEO of Expensify, whose purpose is “To improve the world one expense report at a time.”

David is a wine aficionado, and all around alpha geek. He started programming when he was 6 and it has been his primary activity ever since, with a brief hiatus for world travel, technical writing, project management, and now running Expensify.

Since 2008, David and Expensify have been making the world a better place, one expense report at a time.

Expensify was recently named one of the Most Innovative Companies in 2015 by FastCompany. A pioneer in the expense management space, Expensify has become the model for all similar solutions.

David is married to an opera singer and has the cutest beagle in the world. David loves third world travel and first class wine, but hates expense reports.

Expensify does "expense reports that don't suck!" by importing expenses, and receipts, from your credit cards and mobile phones, submitting expense reports through email, and reimbursing everything online.

It has raised over $6 million in venture funding, has hundreds of thousands of users, has won awards aplenty, and is basically taking the small-business expense reporting space by storm.


We discussed his “Please Don’t Call Us “Cockroaches post, where he suggests the name Tardigrade instead of cockroach.


How’d you get here?

Company almost never happened? Started as prepaid debit card idea?

Expensify’s Non-Enterprise Sales Model

It sells to the end user and is thus pulled into organizations from the bottom up, getting around IT and procurement!

Since it started in 2008, it has spent nothing on promotion and grown to 4 million users.

As Robert Stephens, founder of Geek Squad, says, “Advertising is a tax companies pay for being unremarkable.”

Expensify uses a Freemium Pricing Model, which has led to 600,000 companies using it for free.

David’s Blog Posts and Articles

David’s blog posts, along with those discussed:

David Barrett on BitCoin


What’s your advice for entrepreneurs?

Stop getting distracted by the bad advice from others. Most advice you get is awful. You can only be an “expert” on the past.

What’s your favorite California wine?

 Little Vineyards, Glen Ellen, CA

What’s been your favorite travel destination?


Ed Kless

Ed Kless joined Sage in July of 2003 and is currently the senior director of partner development and strategy. He develops and delivers curriculum for Sage business partners on the art and practice of small business consulting. Courses include: Sage Consulting Academy, Business Strategy and Customer Experience Workshops. Ed is the author of The Soul of Enterprise: Dialogues on Business in the Knowledge Economy, a compendium of a few of the episodes of his VoiceAmerica talk-show The Soul of Enterprise: Business in the Knowledge Economy with Ron Baker, founder of the VeraSage Institute where Ed is also a senior fellow.