Kirk co-founded Wave in November 2010. As CEO he’s led the company to milestones including more than 1.5 million users, venture funding from top VCs in Silicon Valley, Boston and Toronto, and a team of 70 team members in four cities. Wave is considered by TechCrunch and others to be one of Canada’s best startups, and has received awards from Deloitte, CIX and more. As a previous entrepreneur, Kirk had experienced the pain of back-office tasks like accounting, which he determined to resolve by creating Wave. Kirk’s earlier ventures, both in online technologies, include a pre-YouTube streaming video service for adventure races, and an online community for outdoor adventure enthusiasts, which he sold to an outdoors magazine in 2010.
Good to Great by Jim Collins
This book gets a lot of attention — some people call it the best business book written in a long time — and for good reason. It’s chock full of insights. One point that stands out in my mind is the importance of getting bad people off the bus quickly. In addition, the author puts emphasis on ensuring your company is set up well for the long-term rather than ripe for failure if you depart (just to satisfy your ego about how important you think you are).
Free: The Future of a Radical Price by Chris Anderson
This book was written by Wired editor Chris Anderson. There has been a lot of conversation about this book relating to plagiarism of a Wikipedia article. That controversy aside, it was a compelling read as we approached the market because Wave offers its core financial products for small business at no cost. There is a lot of good insight in here about the cost of technology, the psychology around how people engage with a free product vs. an inexpensive product, how expectations around free/paid are changing in recent years, and how a price of $0 can be a user acquisition tactic.
Quiet: The Power of Introverts in a World That Can’t Stop Talking by Susan Cain
My co-founder, James Lochrie, gave me this book to read. Because he is an introvert, he wanted me to better understand how his brain works. It was incredibly insightful and has allowed me to understand and work with him more effectively. Given that the technology industry is filled with introverts, it’s very important to understand how different people view everything from meetings and office set-up to product development and marketing, and more. If you’re anything like me, you can find relationships where these insights apply both within your own company and with external partners and colleagues.