Dave's father has a stack of business cards for all the entrepreneurial companies that Dave started as a kid. Among these was Dave's Diving which offered golf ball retrieval services by Dave manually swimming the water fouls and picking up balls. It was while trying to launch Dave's Diving that Dave learned about the importance of market traction; it turns out there was a much better solution already being used so he was offering a solution without a problem. These early entrepreneurial learning experiences lead Dave and his brother to start Yellow Pencil almost 25 years ago. During his time at Yellow Pencil, Dave worked on a variety of branding projects including Edmonton's Festival City brand as well as a branding project for the Province of Alberta to unite all the various Ministries to a common look and feel. Yellow Pencil has also done work for municipalities across Western Canada, including getting fired by the City of Vancouver and building the current City of Edmonton website.
After 22 and a half years working with Yellow Pencil, Dave realized that he was no longer excited about the strategy and direction that they were going so he stepped away to let the great team that he had assembled take the reigns. Dave exited and his brother took a senior leadership role. Dave tells us this was an interesting process, and he is thankful that he and his brother are still able to sit across a dinner table due to an amicable exit. There are many examples of companies who did not have such a painless separation process, and these exits can become much more stressful and challenging when family is involved.
After exiting from Yellow Pencil, Dave joined the team at Zept who are working to solve the problem of determining which international school a student should pick after they have decided to study abroad. This is an incredible challenge since many factors including school reputation, cultural fit, desired career path, learning style, among many other factors can determine whether a particular school is an appropriate fit for a particular student. Zept is solving these problems using AI-powered algorithms to help match students to a school where students similar to them are most successful.
Dave shared with the Rainforest group that he sees a variety of inflection point for growing companies (points in time or a companies growth where many things change at once and the approach to growing that company needs to adapt for continued future success). Up to around 10 employees, things can feel random (often called agility) and it becomes time to start establishing clear processes. By the time a company grows to around 25 employees, these processes will break because the old systems or ways of doing things break down as the company starts scaling. It is important that a growing company not only revisit their systems and processes but also adjust the management style to suit their current and approaching situations. According to Dave, a company of 2-10 employees can be managed by "looking around", but around 11-25 people the need to establish proper management becomes unavoidable. This is a skill set that may exist within the founding team/existing senior management, it may be a skill set that can be learned by this group, or it may need to be brought in depending on the skills, interests and focus of your team. Once you pass 25 employees, everything will need to be reinvented again as the company enters a new stage of maturity.
Dave also talked about the importance of taking the time as a founder to reflect on challenges and situations that the team faced, how these could have been avoided or better handled, and also to ensure that once you've learned what is available to be learned, that you shrug off the past (since challenges and failures are inevitable, especially in a growing or innovative company), and make sure to not take too much of what happens personally.