Founder Stories: John Holmes II On Building WeWorked

In today’s Founder Story, we feature John Holmes II, co-founder of WeWorked!

Read on for lessons he has learned from launching and marketing his business.

1. Please introduce your business and share your role. 

My name is John Holmes II, and I am the co-founder of the easy-to-use, small business preferred time tracking software application WeWorked. As co-founder of a small business, I participate in all areas of the company, from programming to branding to marketing to customer service. Our goal is to create affordable enterprise-grade software for businesses of all sizes.

2. What’s your backstory, what kind of challenges did you face, and how did you come up with your business idea?

The idea for WeWorked was formed by Will Roberts III and me in 2009 from the realization that quality software was too expensive for small businesses. Software was just starting to move away from the localized on-premise standard to the now standard Software-as-a-Service model.

On-premise configurations were expensive and time-consuming. We saw the direction software was headed and built WeWorked to help small businesses around the world track employee timesheets without the burden of extensive training and costly hardware.

3. How did you prepare for, and go about your launch?

Starting out we offered WeWorked for free with the goal of obtaining a sizable user base to which we can request feedback. Our search engine strategy and marketing approach focused on the fact the software was free in exchange for feedback. We understood the software was not comprehensive enough at the time to warrant payment. 

4. Since launching, what types of marketing campaigns and designs have worked best to attract and retain customers?

Over the years, our most effective marketing campaigns involved a mixture of search engine ads, website videos, and radio promos. We tried several print campaigns, but the return on investment was difficult to measure and costly to create. Our upcoming campaign will include some podcast placements.

5. What have been the most influential brands for your business? Whose branding and marketing do you aspire to and why?

When it comes to influential brands, we have to mention Apple, Salesforce, and Basecamp. Apple has an amazing ability to create a culture around its product offerings. Salesforce is a master at attracting both small and large organizations, including government agencies. Basecamp is a great example of a bootstrapped software company that makes its own rules.

6. What are your favorite marketing platforms/tools?

Google Ads is the industry standard. Google Ads puts you right in front of the customer who is actively searching for your product. It is difficult to find a better platform for real-time marketing.

7. Who or what inspires and motivates you?

I am inspired by people in various industries. I am inspired by entrepreneurs in music, such as Nipsey Hussle, Steve Stoute, and Jay Z. I learn from tech entrepreneurs like Steve Jobs and Tony Hsieh. I also am motivated by Jack Welch and Magic Johnson. 

8. What are some lessons you’ve learned along the way that you would share with entrepreneurs hoping to launch or who have just launched? 

Steve Jobs famously said, “Real artists ship”. Create something and push it out to the world. Nothing is perfect. All software has bugs. All products have defects and improvements that could be made. Get started. Success in business is a never-ending process and constant pursuit. 

9. What do you believe are the qualities of a good entrepreneur? And what makes a team successful?

 Good entrepreneurship begins with a focus on providing the world with something that is missing. Money is typically not the focus for successful entrepreneurs. Money should be the byproduct of delivering what the world needs.

10. Let us know where we can go to learn more! 

Visit us at to get timesheet software for your business today!