As technology progress is in fast mode, businesses must follow its course closely to meet their goals. Thus, to grow a business, one must have an unobstructed company workflow.

David Barrett, a coding enthusiast from Michigan, seized the opportunity to present a solution to get reimbursement to companies in 24 hours. According to him, a business never fails - but runs out of money. Therefore, time is money, so, here’s Expensify.

Expensify is a company meant for business travelers. It simply reads the information from receipts and sends them to the company for reimbursement. That facilitates the waiting period and reduces it to 24 hours.

The story of Expensify is one of the turbulent ones as it begins with David's words "Expense receipts that don't suck!"

It's constructed with lots of ups and downs, rebellion, and finally - success. But, let's take one at a time!

A Tech Dynasty Offspring

David Barrett was born on August 10, 1990, in Saginaw, Michigan.

Ever since the first time he was tête-à-tête with technology, and the internet, David was already drawn to it, to the core.

His parents didn’t object to his mother tongue being C++, as he started coding at only 6 years of age. Even with all the constraints and efforts David’s parents did to detach him from the computer, he was still persistent to continue learning more about programming.

Things heated up when he was a teenager; David became more active, and one of the brightest students in his department when programming came into question.

David had a rebellious side to him which fully came to alight when he was in his teens and early twenties. He believed he had the spirit that would change the world for the better.

Once the time to pick a faculty arrived, David’s ma=ind had already been made up, all the way back to childhood.

Too Busy to Rest

David chose the University of Michigan as his gateway to the world of technology, impatiently awaiting to study software engineering. Contrary to popular opinion when it comes to college, David’s student years weren’t reduced to parties or skipping morning classes, not at all! Instead, he found a way to further develop his ideas - VR labs!

At that time, games characters were still cubical and pixelated that basically begged for improvement to morph into something more realistic. While David was at college, he dedicated a fair share of his time to virtual reality, a niche that turned out to be close at heart for him, later on.

Right after he graduated from university, David decided to take the road to Texas, where the video game industry was booming. There he started to develop 3D graphics engines.

But, that wasn’t the only workplace David stepped his foot in. His next stop was Red Swoosh - a peer-to-peer file-sharing company where David spent most of his career. Later in 2008, Akamai Technologies bought Red Swoosh. In that same year, David left the company and decided to create his own.

Company in the Making

After David left Red Swoosh, he decided to stay in San Francisco to clear his head and figure out his next moves. During his stay there, he noticed that the homeless of the Bay Area were left in the fight for survival. Therefore, he started a project to help homeless people around his neighborhood that was more sophisticated than simply giving cash to people.

His idea was to create a debit card for people to donate to the homeless. Then, the homeless can use it at pre-approved vendors. Although the idea was more than humane, banks seemed deaf to David’s proposal.

However, David still didn’t give up on the idea to further develop his plan. Instead, he remodeled his business plan into a prepaid debit card that businesses can use for traveling expenses. Backloaded with $15 million from Red Swoosh, David had exciting news to share with the San Franciscans. Meet Expensify!

What Is Expensify?

In 2008, David officially launched his Expensify company in San Francisco. Although the headquarters were in the Bay area for 9 years, yet, in 2017, David decided to move the official offices to Portland, Oregon.

Expensify is an app fit for business travelers. It features a simple interface where all you have to do is take a picture of the receipt, and Expensify will run everything necessary to provide you with a reimbursement.

Essentially, it reads the relevant data from the receipt and transfers it to your company for reimbursement. The entire process should help you have the funds in your bank account in less than 24 hours.

Expensify Behind the Scenes

As main investors that supported the company along the way, PJC, OpenView, and CIBS must be singled out as lead backup investors.

Expensify got a good start as in 2009, the company announced a raise of $1 million. Although 1 million bucks isn’t a sum to complain about but compared to the funding raised in 2010, it came as humble.

In 2010, Expensify raised $5.7 million, and in 5 years span, the company managed to triple its budget for 17 million bucks. Enlarging the budget thrice supplied enough means for Expensify to consider bigger business goals, like expansion.

Growing and Expanding Some More

The first expansion was in Portland, but then Expensify appeared in London, Melbourne, and Ironwood, as well.

The first and largest office is situated in Michigan and is considered one of the largest in the US. Also, Expensify partnered with Gogebic College, and now it offers scholarships to local students who want to learn more about programming.

Therefore, at the beginning of 2015, Expensify launched Expensify Ventures. It was a venture capital arm that contemplates strategic investments in early-stage travel, payments, and finance.

When the company started, there were only a few employees along the way. But, nowadays they will round up the 250th vacancy.

The COVID-19 pandemic was a huge hit not only to Expensify but his rivals at SAP Concur, Fyle, and Zoho Expense, as well. However, once the pandemic settled, David decided to take his company on a different level, and go public.

On November 10th, 2021, Expensify had its first IPO debut. In fact, everything went as planned, and it was a prolific move. During the IPO, Expensify raised $263 million

Facing Allegations

As Expensify operated with classified information, the hazard of exposing it was one of the main concerns that determined whether the app will be used or not. As David and the team reassured that such situations are impossible - then the impossible happened.

In November 2017, the company got accused of exposing personal information. Apparently, someone manually breached the information from the receipts through Amazon’s Mechanical Turk service. Eventually, it turned out that Expensify’s concept wasn’t as secure as presented. Expensify admitted that there was a bug that entered 200 receipts.

Besides the fines the company paid, Expensify enhanced its security system to prevent such situations in the future.

Opposing the System

After the allegations and lawsuits for the breach, 2020 was an electoral year in the US. As mentioned, David had a rebellious side in himself that he demonstrated through an e-mail. Allegedly, David couldn’t accept Donald Trump’s plausible democracy and sent tons of emails to his US customers to raise awareness.

However, instead of increasing awareness, David lost many clients and started receiving death threats. His move was not only dangerous for the business but to his life, too. But, it’s important to mention that David’s only intention was to crystalize the idea behind the e-mails.

David believed that hiding behind the oppressed system was hypocritical of his fellow start-up colleagues.

“No, I’m voting for the status quo. I support the current administration, and I’m not going to take action to do anything about it because it’s actually good for business.’ I think it's actually pretty cynical.”

David not only stands behind his claims that no company that stands behind the US should remain silent, but also he donated $3 million to “systemic injustices”.

Enlarging the Receipt

As time passed by, more and more people became interested in using Expensify’s services. David, alongside his employees, did their best to stand back up once stricken, and show what they’re made of.

As of now, not only did David fulfilled his business goals, but he overachieved them.

This December, David takes the opportunity to set new goals that will further develop the company, so it’s up to the world to sit back and see what’s next in store with Expensify.