Our Timesheet Software Went From Side Project To $1.2M/Year

Will Roberts III
Founder, WeWorked
from Brandywine, MD, USA
started April 2009
alexa rank
market size
avg revenue (monthly)
starting costs
gross margin
time to build
300 days
growth channels
best tools
Quickbooks, Instagram, Twitter
time investment
Side project
pros & cons
34 Pros & Cons
3 Tips
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Hello! Who are you and what business did you start?

Hello, my name is Will Roberts. I am a Co-founder of WeWorked. WeWorked is an easy-to-use timesheet software product that integrates invoicing, leave tracking, expense tracking, and more. WeWorked is designed specifically for small businesses in any part of the world.

Most business software is designed for large enterprise customers, which results in high prices, unwanted features, a slow enhancement rate, and terrible customer service for small businesses. WeWorked focuses on the time tracking needs for small businesses by integrating leave tracking, invoices, expense tracking, and reports into an online application at an affordable price point.

We are bootstrapped and profitable hosting timesheets for about 20k subscribers and average monthly revenue of $100k.

Explainer video:


What's your backstory and how did you come up with the idea?

Growing up as a kid in inner-city Washington, DC, I always had the gut feeling that I was meant to do something big. Although I had absolutely no idea of how I was going to get there, I was 100% certain that it was to be. However, it wasn’t until high school, located in a more affluent area than my own, that it became clear to me that my path to “something big” was entrepreneurship.

The beauty of launching your own product with no outside investment is that there’s never a right or wrong. Things either work or they don’t. Whatever works, we keep doing it.

With WeWorked in particular, my Co-founder John Holmes and I birthed the idea following many years of experience working for small businesses that often struggled in addressing their organizational time and attendance needs. The solutions they employed were almost always either unaffordable, too complicated, or just not very good. And many times they were all of the above.

Take us through the process of designing, prototyping, and manufacturing your first product.

The prototype took about 3 months to develop. We started with only the web version. The android and iPhone apps came years later. We did, however, have a mobile-friendly version that worked pretty well on mobile browsers.

See screenshot from version 1:


John and I met while working for a small contracting firm in DC where we developed custom software for the federal government. The entire team consisted of only about (5) people and each of us was required to be heavily involved in the development process from design to delivery. We were all cross-trained so that we could perform interchangeably and fill in for one another at any stage of the software development lifecycle.

As I mentioned earlier, I knew from a very early age that I ultimately was going to start my own business but at the time when John and I met I still didn’t really know what that business was going to be. I can recall him and me often bouncing various business ideas off of one another.

In the beginning, most people either thought I was just talking and ignored me and/or felt I would ultimately fail. It wasn't until people started seeing the fruits of my success as an entrepreneur that they started to take notice.

Although we didn’t decide to launch WeWorked until many years later, I would say that this experience created a solid foundation and inspiration for where we are today. The experience that we gained during that period was the perfect springboard onto what would eventually become WeWorked.com. We knew that we could definitely work together and build just about anything we wanted. In addition, John and I knew each other's skill level and work ethic. We had been in the trenches together and emerged victorious on many occasions.

Both John and I were software developers by trade, so when he pitched the idea to me, it was a no-brainer given that we could literally launch the product with the sweat off our backs. The majority of our development software was open source, even the database, which started as MySQL. Adobe was probably the only paid software we used. There were plenty of open source options to choose from to launch a product. So the only substantial investment required to launch our startup effort was our time. That decision ultimately placed us in a very unique position by which we were able to launch our tech startup with absolutely no outside monetary investment.

Given that we both had full-time jobs, we were required to work evenings, late nights, and weekends to get to a point where we could launch. I can confidently say that the time and effort that we invested upfront in developing the prototype is easily equivalent to a minimum $2M cash investment.

Our initial requirements consisted of bare-bones timesheet functions. All of our features were constructed from a United States perspective. The goal at launch was to determine if a historical enterprise market was ready for a SaaS version. We quickly learned the SaaS timesheet market was global. As a result, we had to expedite international features. WeWorked grew the most in the first year of release.


Describe the process of launching the business.

From inception, I remember us making the analogy that we wanted to position ourselves to be the equivalent of the merchants that sold picks and shovels during the Gold Rush of 1849. Admittedly, we knew that timesheets weren’t the sexiest or innovative idea but we also knew that almost everybody needed them in their quest to launch and sustain a successful business endeavor.

Although we had a solid target demographic in mind, we unintentionally made an assumption that may have led us in a slightly different direction initially. As it turns out, we were somewhat blinded by the fact that we were physically located in the States.

As American citizens, we are subconsciously conditioned to believe that business only occurs within the borders of the 50 states. However, an extremely aggressive and successful SEO strategy would prove that those borders were imaginary. We started out thinking that our target demographic existed solely within the U.S. But as it turned out, our customer base was indeed the entire globe.

There was one customer in particular that made that ever so apparent. This company was a UK-based retailer of auto tires with several thousand employees. They signed up for a free trial of our system and loved it with one exception. The system was designed for use in the U.S. Therefore, things like currencies, date formats, and timing of notifications didn’t align with their specific needs as a foreign entity.

John and I put our heads together and determined that this was a golden opportunity to make the product more flexible and internationally friendly. We offered them an unlimited subscription for a discounted flat fee with the agreement that we would make changes to accommodate their needs moving forward. This move ushered us into the worldwide market where we now host timesheets for more than 50k subscribers in over 120 countries.

Since launch, what has worked to attract and retain customers?

Our business model and strategy employ many unique concepts that are still widely unheard of in the software industry. We don’t offer telephone support. We don’t employ a sales team. We don’t offer product demos. Yet, we compete for neck and neck with major industry players like TSheets and Replicon who have estimated investment totals of $20M and $40M, respectively. These companies and many similar are bleeding cash and wouldn’t survive 30 days with VC money.

Given that many of our concepts were so groundbreaking, there was no frame of reference or advisers to seek guidance from. In fact, we had two mentors that continue to advise us to this day. Their names are “Trial” and “Error”.

The best business ideas don’t require large amounts of money to get started. Time is your most valuable asset. Don’t be afraid to launch a product that already exists. Sometimes there’s an existing void within a market that can be tapped into very lucratively.

The beauty of launching your own product with no outside investment is that there’s never a right or wrong. Things either work or they don’t. Whatever works, we keep doing it. Whatever doesn’t work, we either abandon it or make adjustments and retry it later. It's that simple. We don’t have investors that we have to answer to and seek approval from. If at all possible, bootstrapping is definitely the way to go. At this point, we’re highly profitable and have no incentive to nor under any pressure to enter into a deal that doesn’t serve our best interests.

Amazingly enough, we’ve been able to thrive without any major marketing campaigns. We attract new customers solely via organic SEO marketing, Google Ads, and customer referrals. We don’t employ sales or marketing teams. As a matter of, we don’t have a published phone number nor provide support via telephone. All of our sales and customer support is done via email and chat. This allows us to maintain low overhead costs and keep our pricing extremely competitive.

Our first strategy was freemium. We simply wanted users and their feedback. Freemium was huge around 2009. People were consistently including the "free" in their search for software solutions. We knew if we focused on the free aspect of SEO along with a focus on small businesses, we would capture our intended audience. People tend to think customers are only paid. The first year, we looked at customer feedback as our most precious tender. With the right feedback, we could evolve WeWorked into exactly what the market needed.

In business oftentimes timing is everything. In 2009, our primary keywords were less than 50 cent to rank above the fold and appear as one of the top links on Google search results. We took a huge loss the first few years as a result of running aggressive AdWords campaigns. However, we knew that our recurring revenue model would eventually bring us in the black as we acquired more customers and gained brand recognition. Today the same keywords would run us double-digit pay-per-click rates. We were lucky and aware enough to be aggressive at the time.

Our ability to retain customers lies largely within the ease of use of our product and our 24 x 7 x 365 Customer Support model. The simplicity of WeWorked.com’s design allows our customers to “go live” within an average of 24 hours with very little user training required. Additionally, our “round-the-clock” support model makes us available to all our subscribers around the globe all the time.

The most remarkable thing about our support model is that it all works with less than 5 team members. All staff members, including the founders, are cross-trained and can perform virtually any required sales or customer support task. This dedication has proven invaluable during the pandemic. We actually increased revenue 100% over the past year.

How are you doing today and what does the future look like?

Building a web application outside of Silicon Valley is extremely difficult today, and virtually unheard of back in 2009 when we started. In the DC area, most software companies focus on government business by building expensive enterprise applications. Good, affordable small business software was rare.

Noticing that many small businesses struggled with tracking staff time, we decided to create a web-based timesheet software with features focused on small business needs. People thought we were crazy or just ignored us all together when they were told about what we were planning. We typically heard "someone already does that", "it'll never work", "you know how to build something like that?" or "it'll take forever". They were sort of right. We had competitors that were large dinosaurs that couldn't survive 30 days without VC money.

It ultimately did work but not exactly as we anticipated. We thought the U.S. was our customer but as it turned out our customer was the world. Ten years later, we have more than 50k users in 120+ countries. We have done the impossible. Competing with big-name timesheet companies like Replicon and TSheets. We had no blueprint, just a dream, and persistence.

Within the past year, we’ve been approached by several firms regarding the potential acquisition of WeWorked.com. These talks remain in progress. Obviously, we are unable to discuss specifics due to the NDA’s that are in place. However, let’s just say the future is looking mighty bright! And until such time that either an acquisition or strategic growth investment makes sense for us, we plan to continue to provide excellent customer service and enhance our product based on the needs of subscribers.

Through starting the business, have you learned anything particularly helpful or advantageous?

The job where John and I met actually turned out to be my last experience working for someone else. I ended up leaving that job to start my own contracting firm. Dealing with challenges in my personal life at the time, I was really put into a situation where I had absolutely nothing to lose. Taking my current circumstances into consideration along with my desire to ultimately be an entrepreneur, I came to the conclusion that it was the perfect time to start my own business.

The challenges of starting a new business served as a welcome distraction from what I was going through in my personal life. I was able to redirect that negative energy into my newfound endeavor. In the beginning, most people either thought I was just talking and ignored me and/or felt I would ultimately fail. It wasn't until people started seeing the fruits of my success as an entrepreneur that they started to take notice.

If we could start all over again and do anything different, I don’t think we would change a thing. Thinking back, every challenge and setback that we encountered and eventually overcame has led us to be at the right place at the right time to get us where we are today. I mean even down to the jobs that we had when we first started out. Those jobs afforded us the necessary flexibility and demanded the precise amount of our time which ultimately allowed us to place the required level of effort and focus required to create WeWorked.

What platform/tools do you use for your business?

We run a relatively lean operation. But the tools that we do use, we rely on heavily:

  • Amazon Web Services - This serves as the backbone and infrastructure of our software platform.
  • Stripe - This is where 99% of our payments are processed.
  • SendGrid - This allows us to communicate with our customers with reliability and helps identify our emails as originating from a legitimate and trustworthy source.
  • Google Translate/Google Chrome Translate - This allows our non-English speaking customers to use our software without any modifications on our end. It also allows us to effectively provide support to these customers regardless of their native tongue.
  • Google Ads - With the diminishing landscape of organic search results on Google, this is a mission-critical source for sales leads.

What have been the most influential books, podcasts, or other resources?

Our product vision, launch, and ultimate success came largely from 37 Signals, their books, and other similar companies. This inspiration led us to launch WeWorked.com using some very unique concepts. One such concept is that we offered email-only support with no contact number or telephone support. Another thing that we did that distinguished us from our competitors was that we bundled our user licenses and elected not to offer the traditional per-user pricing model. Both of these concepts allowed us to offer lower pricing to small businesses.

Below are some other influential resources that got us here:

Advice for other entrepreneurs who want to get started or are just starting out

The best advice that we can give someone starting out is to have them understand that the best business ideas don’t require large amounts of money to get started. Time is your most valuable asset. Don’t be afraid to launch a product that already exists. Sometimes there’s an existing void within a market that can be tapped into very lucratively. Technology can be used to reach customers all over the world. The right product, pricing, and marketing can allow you to compete with the biggest and best.

Our biggest sales driver to date has been aggressive SEO marketing. However, for a brief period while we were listed on the Wikipedia timesheet software comparison page. During this span, we experienced a surge of 1000+ sign-ups within a 48 hour period. Although our listing was subsequently removed soon thereafter, it became clear that the key to us blowing up exponentially was simply exposure. We were literally one magazine article or press interview away from being purchased for $350M like TSheets.


  1. The best business ideas don’t require huge amounts of money to get you started. Your time is your most valuable asset.
  2. Don’t be afraid to launch a product that already exists. Sometimes there is an existing void within a market that can be tapped into and be very lucrative.
  3. Technology is your friend and the internet can be used to reach customers all over the world. The right product and marketing can allow you to compete with the biggest and best.
  4. Do something that you’re passionate about.

Where can we go to learn more?

If you have any questions or comments, drop a comment below!

Will Roberts III, Founder of WeWorked
Pat Walls,  Founder of Starter Story
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