Simplicity – Why It Matters and How To Make it Part of Your Story: Drew Houston And The Founding Of Dropbox

drew houston dropbox entrepreneur lyn graft mit simple simplicity storage stories story storytelling

How Drew Houston used the story of forgetting his thumb drive on a 4-hour bus ride as a catalyst for creating Dropbox, a cloud-based storage solution now used by 400M people


Headphones and laptop in hand, Drew Houston stepped on a bus in Boston fully prepared to start cranking out a ton of work. He had finished his undergrad at MIT two years earlier and was working nonstop to get his startup idea (an SAT-prep testing software solution) off the ground.

Recently Drew’s parents asked him to come to New York City for the weekend. Though he wasn’t excited about missing a few days away from his startup, he figured he could see some friends and use the four-hour bus ride, each way, to get a ton of focused work done during the downtime.

He hopped on the bus, reached in his pocket to grab the flash drive where he stored all of his most important files, when a gut wrenching feeling came over him… his pocket was empty.

“I’m running late so I jump in the cab and head to the bus station and sit down on the bus and as I open up my laptop, I get this feeling in the pit of my stomach—that I’m sure many of you have experienced at one point or the other. ‘Something has gone terribly wrong.’ And then, I knew what it was. I could just vividly see in my mind’s eye my thumb drive sitting on my desk at home.”

Drew freaked. He had no way to access his files. He couldn’t do any work on the bus, and worse, he would not be able to work for the entire weekend. This was 2007. Before most people even knew what the cloud was, much less be able to access their files remotely.


At MIT, Drew never had to worry about this kind of problem because the University had a specialized computer system called Athena which enabled you to sit down at any workstation on campus and see your digital files whenever and wherever you wanted. You could access your document, as well as your personalized desktop layout, and you never had to worry about backing things up. Everything was always there and it always worked.

Now, Drew was experiencing what the rest of the world had to deal with when it came to working remotely.

Drew realized how fickle it was to have a tiny device that could easily be lost, stolen, or misplaced in which to store your life’s work. His engineering brain kicked-in and he decided to figure out how he could solve the problem for the every day person who wanted to remotely access a file. How could he help people with all of their file storage and transfer, regardless of location or device, in the same way Athena made it possible for MIT students?

He feverishly started writing code to come up with a quick and dirty solution. Though he didn’t know it at the time, those lines of code turned into a solution called Dropbox: a simple way of having all your photos, documents, and ‘everything that you care about’ accessible 24/7, always backed-up, and secure. Instead of having to move photos and files from your laptop, phone, and tablet through a hard drive or thumb drive, then over to your desktop, you could access them over the “cloud” from any device.

In the following months, Drew was being drawn more and more into this Dropbox idea, and eventually abandoned the SAT idea to focus. Despite the fact that the storage market was highly competitive, no one had solved the problem in any simple or elegant way.


At first, he couldn’t get any traction from investors so he decided to create a video in an online tech community called Reddit to see if he might get the attention of some of the partners at the famous Y-Combinator Incubator that he wanted to get into. He knew they were regularly following Reddit, looking for new ideas and products.

Drew created and self-narrated a 4-minute video in his apartment. It showed the products and the prototype and kept it super basic and threw in some programmer & pop-culture references for good measure.

This simple DIY video made it to the front page of a popular tech-news site (digg) and it had it’s intended affect. It got the attention of one of the Y-Combinator partners. The video also ended up helping Drew find his co-founder, get valuable feedback on the product for future iterations, and build the company’s early user base.

But despite getting the meeting and having users, the Y-Combinator partners, investors, and critics pointed out that there were already a large number of storage companies in the market. Most had deep pockets, vast resources and brand names. They asked him, “Why are you building another storage service?” Drew responded immediately, “Do you use any of them?” And they all answered no.

He would go on to share that he had the same problem. He didn’t use any of those other offerings because nobody made something that was simple, that people really liked to use, and that was elegant and uncomplicated for the every day user.

“With something like Dropbox, it was immediately like, ‘Wow, this is literally something that anyone with an internet connection could use.’ Everyone needs something like this, they just don’t realize it yet.”

Drew kept iterating on the “simple storage” idea and eventually got into the well-respected Y-Combinator incubator. They helped him secure Dropbox’s first seed round and Drew has gone on to secure hundreds of millions since. Through it all, simplicity became a mantra for Drew in everything that revolved around the product and its communication. It didn’t matter that what they were trying to do was incredibly complex.

Today, Dropbox has over 400 million customers and generates over $400M in revenues yearly. Every day, over 1 billion files are filed to 500 million connected devices in 200 countries. It is one of the most used cloud-file storage solutions in the world.


“Nothing is more simple than greatness; indeed, to be simple is to be great.” ~ Ralph Waldo Emerson

As Drew will attest, one of the most important elements of Dropbox’s story and success is simplicity. He knew that to create a massive, global system for storage of any file, anywhere, on any device, which could magically make all the files go into the cloud without question – it had to be communicated and delivered simply.

Dropbox’s unwavering focus on simplicity and creating a product that “just works” caused users to be emotionally connected to their offering. It literally inspired a cult like following (me being one of them) because so many people loved it and depended on it. Drew found that the more concise and digestible Dropbox made their offering and message, the more success they had in people comprehending, using, and sharing it with others.


Life is complicated. Every minute, 31.25 million posts are made on Facebook, 347,000 tweets are entered onto twitter and 300 hours of video are loaded to YouTube (CIO Magazine). Every day we are over inundated with ads, information, news, pictures, and updates on our phones and devices. And as technology advances, everything is only going to get more complex. We are so overloaded with information that when a new business or story comes to our attention, if it is simple and grabbing, it gives us a chance to digest and internalize it.

People need and want simplicity in their everyday lives. More than 80% of people today are looking for ways to simplify their lives (“Simple: Conquering the Crisis of Complexity” By Alan Siegel & Irene Etzkorn).

As an entrepreneur, the best thing you can do for yourself and your audience is to keep things simple. Keeping something simple is a gift and a blessing to many people because it is a way to make their lives easier, or more accurately, make them feel like you made their lives easier.


Drew’s experience of forgetting his thumb drive is of my favorite examples to reference to entrepreneurs when it comes to simplifying a complicated concept down to an easy, digestible story. Here are lessons on the principle of simplicity in storytelling you can take from Drew’s success:

1. Identify the One Hook

In the conceptual stage of Dropbox and well into the post-launch timeline, Drew found that there were a number of companies trying to solve the same problem of file synchronization in the way that he had envisioned. This led to a good deal of confusion in the marketplace (investors, customers, press, etc.) as well as users who were dissatisfied. But the reality is that very few people were actually using these products because of this confusion, they were too complicated to use or they flat out didn’t work.

To push through the clutter, Drew decided to focus on a specific ‘hook’ which resonated with users. It centered on the ‘ease of use and the simplicity’ of their offering and he made it part of their story. He felt that was what audiences were most likely to respond to.

To take hints from Drew, even if your offering is the Swiss army knife of your industry and can do everything under the sun better than anyone else, focus your message on the main element that is going to catch the attention of your audience.

“We’ve found it’s a lot more effective to find one hook that people can easily understand. That gets people in the door. Once you have that relationship with a customer, then you have all kinds of opportunities to educate them over time as to everything else that the product can do.” ~ Drew Houston

2. Make It Sound and Look Simple

Once they settled on the hook, Drew and team focused everything on making it look and sound as simple as possible. They made sure that Dropbox was simple to explain, simple to understand, and simple to use.


This wasn’t the easiest thing to do because what Dropbox was doing was incredibly complex. So they focused on creating the perception that Dropbox was easy – that it had the illusion of simplicity even if was rocket science and had hard-core computer stuff happening in the background. If you think of Dropbox, it does almost seem like magic. You just upload all your files to the cloud, drop them in, and all is saved.

“We want you to have your stuff with you wherever you are, and that requires that we remove anything that gets in the way. There are technical hurdles that we’ve had to overcome to provide the illusion that everything is in one place, that it just sits there, and that getting it is reliable, fast, and secure.” ~ Drew Houston

The beauty of Drew’s offering was in providing a simple solution to solve the problem and complimenting it with a simple message and brand. You can explain the idea and benefit of Dropbox to a user quick and easy.

3. Permeate Simplicity

Drew Houston brought this approach to everything that the company did. Simplicity became a core tenant of their story, no matter how a person saw or heard about the company: messaging, videos, web site, name, icons and graphics.

They started out their messaging with a simple prototype and a DIY-type video. The video was short, easy to understand, and catered to their target audience. It was a concise demonstration of how Dropbox worked, using pictures and screenshots (which Drew made himself). This simple messaging extended to the landing page when someone visited their web site for the first time, the user interface and experience when customers first signed on and used the product. It even extended to the icons on their desktop (which were magically simple to use – just install a folder on your desktop and drag your folders to it).

With everything involved being so simple, it made it easy for customers to use the product, explain the offering, and more importantly, share it with friends.

4. Stay on Target and Stick to the Story

Two of Drew’s favorite mantras when describing Dropbox are:

“It Just Works.” and “If you can save a file, you can use Dropbox.”

Take cues from Drew’s style. There will always be temptation to get more complex or explain more in your messaging. But, don’t get distracted. Stay on point.

Also, make sure to stick with your story – don’t be afraid to tell it over and over and over and over. If you look at speeches, keynotes, and interviews with Drew, you’ll see he always shares the same, simple story of that four-hour bus ride when he left the thumb drive at home. It may seem like overkill if you study him all the time, but to every audience he appears in front of, they are drawn in and easily understand the problem, message, and solution. Once you simplify your core offering and messaging, use it with everyone you speak to: investor, customer, client, or friend.


Drew Houston Talk: Finding Your Way as an Entrepreneur – Standford Univ (May 2012)


If you want to get into more of the nitty gritty of the technology side of the story, here is a great conversation between Salman Khan, founder of the Khan Academy, and Drew from Oct 2014.



Drew’s story resonated with me deeply because forgetting a thumb drive is a problem I’ve experienced many times over the years. When the opportunity came to film him, I was giddy.

As entrepreneurs, we are drawn to always improve or change things because it’s in our nature. But when it comes to your story, sometimes its better to stick with a good thing. The more you either reduce the number of steps and/or increase the speed of understanding, memorability and repeatability, the better your chances your audience consumes your message and becomes a believer – and sometimes even better – an evangelist for you.

I was filming a project for Rusty Rueff and Shelby Bonnie featuring innovative CEOs and entrepreneurs out of Silicon Valley for a presidential campaign in 2012. I’d been using Dropbox every day since I discovered it years before and it just so happened that every person on my crew that day also used Dropbox (many in the production industry use it). When I met Drew that day, I had to share with him that fact and how I LOVED his creation and his story. I shared how I’d forgotten my thumb drive more times than I’d care to admit on shoots and even ended up tying it to my keychain to reduce the chances I’d repeat that mistake. Dropbox changed that and I’d convinced about half my clients to use Dropbox since that time.

Thanks for making my life easier Drew. Myself and the many Terabytes of files I now have on Dropbox, including this photo, are forever grateful for you forgetting that thumb drive nine years ago.


Lorem ipsum dolor sit amet, consectetur adipiscing elit. Cras sed sapien quam. Sed dapibus est id enim facilisis, at posuere turpis adipiscing. Quisque sit amet dui dui.

Call To Action

Stay connected with news and updates!

Join our mailing list to receive the latest news and updates from our team.
Don't worry, your information will not be shared.

We hate SPAM. We will never sell your information, for any reason.