Advice for Entrepreneurs From One of Rover’s Co-founders

Philip Kimmey shared his experience on how to create a tech startup, and take it from a hackathon idea to a successful company

Tech startup advice from Philip Kimmey

The second episode of OctoTalks is out! This time around, we interviewed one of Rover’s Co-Founders, Philip Kimmey. We’ve worked alongside Rover for a few years now; we’ve seen the project’s scale and the success and attention it’s brought. We invited Philip to talk about his product’s impact on the lives of thousands of people, and how the process has been, from the initial idea to the current Rover platform. Here is an extract from that conversation, if you’d like to listen.

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I read somewhere, Philip, that Rover began as a startup in a startup hackathon back in 2011. Can you tell us a little bit more about this story and how the company was born? 

I attended a nonprofit startup weekend after my junior year of college. A guy named Greg pitched the idea of an Airbnb for dogs, inspired by his own negative experience with traditional boarding facilities. Intrigued, I offered to work on the idea for the weekend. These hackathons involved pitching ideas and presenting prototypes and business cases. Little did I know, this weekend project would turn into a 12-year endeavor. Greg became more enthusiastic about the potential and asked if I wanted to work on it full-time. Excited about combining dogs and technology, I agreed. I joined their office in Seattle and started working on it full-time in less than two weeks.

Are you a cat person or a dog person? 

I grew up with cats, but I’m allergic to them. However, I still enjoy interacting with cats when I visit friends’ houses, even though it triggers my allergies. I consider myself both a cat and a dog person. Currently, I only have a dog named Ajax.

Philip, as you  know,  Octobot and Rover have been working seamlessly together  for a long time. Our mission as a company is to transform people’s lives through technology. How do you think Rover transforms people’s lives similarly in this way? 

When it comes to Rover, I see two examples of how it transforms people’s lives through technology. First: there are people who choose to become full-time dog sitters instead of following their previous careers. Being able to spend time with dogs brings  joy and fulfillment. There are also retirees who use Rover to generate income by transforming their backyard into a dog-sitting space, thus avoiding dipping into their retirement savings. Rover also benefits pet owners by providing them with the assurance that their pets are lovingly cared for while they are away. This small, but meaningful, impact improves the lives of all involved, offering a personalized care alternative.

As  a pet owner yourself, have you  used Rover before?

Yes, I have used Rover before both as a sitter and as a customer. As a sitter, I enjoy having dogs over for my dog Ajax to play with. It’s fun to see them become best friends and spend the day playing together. Although, there was a moment when he teamed up with another dog and dug a hole in my backyard and I had to scold them. Overall though, it’s a great experience to have other dogs around because it brings joy to both me and Ajax. 

It was probably interesting for you to have the experience as a user. Have you identified improvement opportunities when using the app? 

Yes, our booking experience is an area we are actively improving. We are focused on addressing any confusion, pain points, and bugs that users may encounter. As a sitter on the platform, I know this is paramount.

I wanted to learn a little bit more about your career. Can you tell us how you became a VP of engineering at Rover, and why do you like this role?

In the early days of Rover, I wrote a significant portion of the initial code. However, I struggled to hire additional engineers. That’s when we brought a CTO to join our team. I was hesitant about having someone as my manager, but looking back, it was the right decision. He brought valuable insights, identified issues with our hiring process, and helped us improve. I learned a lot from him, and Rover wouldn’t be where it is today without his contributions.

Later on, I transitioned into the role of VP of Engineering. I contemplated pursuing a more hands-on coding role or a product management role, but ultimately, I gravitated towards engineering management. I enjoy leveraging my technical skills and staying connected to the latest industry developments. While I occasionally miss coding, I find fulfillment in enabling and supporting our talented engineers. 

Working at Rover has been an evolving experience. Initially, I thought 10 years at one company would be unimaginable, but as Rover grew and changed, it felt like having a new job every two or three years. 

Well, after these 10 plus years of growth for Rover. Could you tell us a little bit more about your expectations about the future, Philip? What do you envision for Rover in the coming years? 

Startups face the challenge of balancing innovation with improving existing products. Our company has been deliberate in avoiding taking on too many new initiatives at once to ensure we can focus on enhancing our core offerings. Our mission is to make pet ownership accessible to everyone; our future developments will align. For instance, we recently acquired a virtual dog training company to expand our services and address the challenges faced by pet owners. Looking ahead, there are areas such as grooming and healthcare that we may explore to better serve our customers’ broader needs.

Philip, tell me  more about  user experience in Rover. How important is it for you to be in touch with your users? Are there any  user-oriented activities? 

The user experience is crucial for the convenience and usability of our product. We prioritize ease for finding and booking sitters on Rover, as well as providing a seamless re-booking process. User experience research, including user testing and panels, plays a significant role in improving the booking area and addressing pain points. Our engineering and design teams are dedicated to  streamlining the product experience, reducing confusion, and enhancing usability.

A very hot topic nowadays is AI. Do you have any opinion about how AI can improve Rover’s features in the long term or how to apply AI technology to the platform? 

Every quarter, we do our Maker Days, as a homage to our hackathon roots. The most recent Maker Days focused on AI, exploring ideas related to GPT-3.5 and image generation technologies. We have ideas for applying these technologies, such as creating automatic avatars for pets or customers. However, there are challenges in terms of cost and data privacy, and we are cautious in sharing customer information. We anticipate that some solutions could allow us to run the models within our own infrastructure, giving us more control over data access. It’s still early days, but we’re closely monitoring AI advancements with great enthusiasm.

It’s nice that you provide these spaces for team members to propose ideas and work together. Tell us a little bit more about working at Rover. 

We have made significant efforts to create a collaborative and friendly environment. And I believe that the type of people who are drawn to Rover also contribute to this culture. Those who believe in our mission are empathetic, care about the work we do, and strive to be good colleagues. It’s important to ensure that each individual maintains and enhances this culture. While initiatives like Maker Days help foster team cohesion and a positive work environment, the key lies in the interactions with team members and managers. Ultimately, the focus is on cultivating a culture through these personal connections.

So, over your journey creating Rover and being part of it for  many years, what are your main learning points as an entrepreneur?

Firstly, finding the right partners is crucial. The success of Rover was made possible because I met my partners, who have played significant roles in the company’s journey. Building a trustworthy and compatible team is vital for long-term success. Secondly, leveraging your core skill set is essential. If you are an engineer, ensure you have the necessary skills to develop your product. With an abundance of  resources, a small team can achieve remarkable results. This principle applies to other areas, such as marketing – especially during the early stages of a company. These are the main things to consider when starting a venture.

Do you imagine that someday you may launch another company? Or do you have any ideas of something different you’d like to do? 

As I approach the 10-year mark at Rover, I’ve realized that every few years brings new challenges, which has kept me engaged and motivated. I deeply appreciate and respect my colleagues, and it would be difficult to find another group of people with whom I feel so proud and fortunate to work alongside. 

Additionally, the mission of Rover, which resonates with my childhood love for dogs, makes it hard for me to envision finding or starting another business that excites me as much. The exceptional team and culture at Rover are reinforced by feedback from others who have moved on to different companies. If you asked me this five years ago maybe my answer would’ve been different, but as time goes by and I see the place Rover is becoming, I have no intention or plans to leave anytime soon.

It’s such a privilege to be able to work in a place that you feel so passionate about. We also wanted to ask as an entrepreneur: if you could go back in time and do something different, what would you do? 

Looking back, I realize the importance of building a support network of experienced technology entrepreneurs early in my journey. While I was fortunate to have my partners as mentors, having my own network earlier on would have been beneficial. Additionally, there were mistakes made as a company that, in hindsight, could have been avoided. Overspending on certain advertising and expanding an on-demand dog-walking product too quickly were lessons learned through the experience. It’s difficult to offer general advice on these matters as they became apparent only with the benefit of hindsight.

Having Philip as a guest was both reflective and inspiring. We loved hearing his insight – if you’d like to listen as well, the full episode is available here.

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