“Curiosity Is My Guide”: An Exclusive Interview with Andrew Peek

Andrew Peek is trying to read the future. And no, we don’t mean that in the tea-leaves-and-crystal-balls sense; Peek’s methods are more exacting, the stuff of experimentation and data analysis. As an angel investor and serial entrepreneur, Peek makes bold financial decisions based on forecasts about the future of technology and its social, economic impact. So far these methods have resulted in an impressive track record; over the past decade, he has been a leading figure in some of Canada’s most notable startups, including giant online retail platform Shopify.

Today Peek’s investment portfolio is exciting and varied, and his commitment to mindful innovation has made him a sought-after public speaker. We recently met up with him at the KOHLER DESIGN FORUM and were so impressed by his insight and enthusiasm that we asked him to put some time aside for us. Here we spoke with the trailblazer about his latest investments and the road to becoming a savvy entrepreneur.

Q: There are certain attributes we’ve come to expect from successful tech entrepreneurs: often reclusive, sometimes socially awkward, yet fiercely competitive and hungry for more. The beginnings of your story are a little different; you’ve described your teenage years as being filled with bullying, drugs, and petty crimes. What was the turning point that veered you from the path of an at-risk youth to a future serial entrepreneur?

I think there are three major events that contributed to my choosing this path. First, my dad was an entrepreneur of sorts. He had a couple moderate successes and a couple moderate failures. Then he had a big failure — one that cost us everything. It made me learn to get comfortable with risk, consequence, and having less.

Second was the bullying. When you are completely abandoned by all of your friends across many years, you learn not to need other peoples’ consent. You learn to walk your own path because you don’t have much of a choice. And third was getting caught.

When I took all my desires for acceptance and channelled them into unproductive things, it nearly cost me a future. Getting caught and facing consequences woke me up to different possible futures and made me decide which one I wanted.

Q: Your career has transitioned from positions with notable start-ups to a portfolio of very different ventures, which range from the hospitality sector to entertainment to AI-guided decision making. What are your own guiding principles when it comes to deciding where and how to invest your time and money?

My curiosity is my guide. I don’t over-think it. If I feel there is a significant opportunity for learning, I am all about it. Having said that, we can’t take on everything, so I’ve learned to be honest with myself about the length of the commitment I’m making. To “get good” at something requires you dedicate a chapter of your life to it. I try to identify whether my desire is to “try and see” or to “get good”. You’re allowed to pursue things for different reasons, so neither is a wrong answer.

Q: The Annex Hotel places a great emphasis, in conjunction with aesthetic, on experience. How did your tech background prime you with a unique approach to the hospitality sector? What did that learning curve look like for you — were there major challenges along the way?

I’ve learned that when technology is at its finest, it is in service of humanity. I try to bring that mindset to any endeavour where I believe technology might stand to improve the experience. It’s not the same as saying, “technology for technology’s sake” which I think a lot of people do without realizing it. As for the specific application to hospitality, technology should be a great differentiator if it’s doing its job properly. By that I mean that personalization is the opportunity, but it can’t come at the expense of too much friction.

Q: You recently gave a talk at the KOHLER Design Forum in Toronto that centred around lean methodologies and how they will help provide hotel guests with the best experience possible. What are these lean methodologies, and how are you working to put them into action?

Lean methodology dates back to car manufacturing and Toyota. It was re-popularized by the likes of Eric Ries, Steve Blank, and others in the software arena. Essentially, “lean” is a practice of releasing technology early, i.e. before it’s “ready”, in order to prioritize feedback cycles and faster iterations. It’s an acknowledgment that no idea comes out of the gate on fire, so it’s best to plan around the fact that you will need to tear down some of what you built.

Q: Technology and “sharing” models like Airbnb have obviously had a huge impact on the hospitality sector. Given your own in-depth knowledge of the space, what do you see as being the future of hotels and short-terms accommodations in, say, ten years?

I think Airbnb’s big advantage is the rate at which they are compiling a profile on the part of the guest. They know where I’ve searched, stayed, what the reasons were, who with­­ — and now, what experiences I tend towards. Hospitality in 10 years will be about personalization, so unless I’m going to populate a travel profile of myself with some other AI-driven operation, then I would say Airbnb will capture the third prong (the first two being uniqueness and experience). Having said that, there is still plenty of time for others to catch up. I just don’t think hotels are wired to think at that scale, so it might end up coming from a new form of travel agent.

Q: One of your ventures is Reset, a digital detox camp. Encouraging people to seek out technology-free experiences would perhaps seem like an odd move for someone whose career is so immersed in tech — but then again, it also makes complete sense that if your professional life revolves around that space, regular reprieves are vital. How do you unplug in your personal life?

I’m actually doing a terrible job at this lately. I’m writing you from the mountains in Patagonia because I have a spare few minutes before I leave on a trek. I think the number one reason I unplug is my fiancee. She’s so patient with me that when things aren’t “urgent”, I try to give her my attention. I don’t always succeed, but she’s definitely my reason for trying.

Q: In your 2015 TedTalk, you attribute Steve Jobs’ success, in part, to his belief that “creativity is an act of letting go.” How do you follow this same principle in your own career?

I’m not afraid to start at the bottom of any industry and be terrible at something out of the gate.

Q: Were there any major tech developments or breakthroughs in 2018 that caught your attention?

I think privacy is starting to take hold as something we can better protect. Tim Cook and others have led the charge at the most influential levels. That’s exciting.

Q: Given your incredibly varied portfolio, we have to ask: Is there a completely new space that you’re considering investing in these days?

I’m not investing in 2019, actually. I’ve poured a lot of money into my own ventures at the moment and I’m focused on getting them to a place of stability. I think I’ll probably invest in films next, though.

Q: Tell us one thing that no one would really know about you!

I changed my middle name to Larkin. It was supposed to be my first name, but my parents got cold feet at the eleventh hour. Larkin was my great-grandfather’s name. He was an entrepreneur and a hell of a poker player.



Photos courtesy of Andrew Peek.