Zvelle In Conversation with Raymond Luk

Raymond Luk

Raymond Luk is changing the face of entrepreneurial finance as founder and CEO of Hockeystick. He is a serial entrepreneur having founded Flow Ventures and Year One Labs. He recently published his first book, Pitching a Leap of Faith.

Raymond is a passionate supporter of entrepreneurs and hosts a weekly live workshop called Pitch Lab to help entrepreneurs improve their pitch. He is also a classically trained musician and pilot. In his own words he is more concerned about following his passions than trying to fulfill someone else's view of his life. He walks how he wants. Read to find out.

“It’s more than a business for me. It’s a mission that’s deeply personal. I’ve spent so much time one on one with founders and seen the effects of financial stress on their mental and physical health. It’s heartbreaking to see the toll it takes on them and their families especially because people can’t wait to celebrate when they succeed. We want to help them on their journey.”
Elle: I can't think of anyone being a better founder or CEO for Hockeystick than you! I love your new product "Funding-as-a-Service'' (FAAS). You have been an entrepreneur all your life, you've bootstrapped many of your companies, raised venture capital and you previously co-founded one of Canada's most successful accelerators. You get how hard this is and you are fighting for founders everyday. Tell me what your vision is for FAAS.

Raymond: People respect and admire entrepreneurs. They are elite problem solvers, they create new products and even small businesses generate a huge amount of jobs and wealth. But ask any founder and they’ll say it’s near impossible to find funding for their business and fundraising is a constant stress. Chasing money takes time away from building the business.

We created funding-as-a-service to turn fundraising on its head. Instead of panic and worry we constantly monitor the company and find the right funding at that time. Our platform is finding funding while the entrepreneur sleeps. Except they probably never sleep!

It’s more than a business for me. It’s a mission that’s deeply personal. I’ve spent so much time one on one with founders and seen the effects of financial stress on their mental and physical health. It’s heartbreaking to see the toll it takes on them and their families especially because people can’t wait to celebrate when they succeed. We want to help them on their journey.

Elle: Are there plans to print your ebook Pitching A Leap of Faith and are there more books coming? Did you enjoy the process of writing the book?

Raymond: Besides us, do any people still read physical books? I grew up in libraries so I need the feel and even smell of print. So yes, one day I’ll print my book and probably add more chapters from everything I’ve learned since. But what’s important is how you learn so I made a self-guided course for people who learn better with audio and video.

Elle: Most people don't know that you studied classical music at McGill before you decided to become an entrepreneur. You are so passionate about music and supporting musicians. In what ways did your music background help you with your entrepreneurial journey?

Raymond: Learning music at an early age taught me the power of small steps. It showed me that I could go from playing one key at a time to playing piano concertos by practicing my craft every single day. That relentless repetition is one of the most important traits of entrepreneurs. It works!

Elle: You are truly an independent person who is not defined by his job, title or external accolades. It's one of the first things I noticed about you when we met twelve years ago. Has this come naturally to you or have you had to work at it?

Raymond: I’ve always been independent and followed my own path. I left home at a young age, lived on my own, lived in different countries and switched career paths when I discovered new passions. That’s why leaving music and becoming an entrepreneur was such an easy decision for me. I just cared more about following new passions than feeling the need to fulfill someone else’s view of my career.

Being an entrepreneur is my ideal role because succeed or fail, I’m not beholden to a gatekeeper or someone else deciding what I should do. It’s not complete freedom because you always have limitations. But it’s independence. There’s a difference.

“I’ve always been independent and followed my own path. I left home at a young age, lived on my own, lived in different countries and switched career paths when I discovered new passions. That’s why leaving music and becoming an entrepreneur was such an easy decision for me. I just cared more about following new passions than feeling the need to fulfill someone else’s view of my career.”
Elle: What's the best and worst advice you've heard someone give to an entrepreneur or been given yourself?

Raymond: I’ll just say that my next book will be called “Advice for People Who Give Advice to Entrepreneurs.” There’s a lot of negativity out there from people who don’t know what they’re talking about and have never operated a company themselves. Whenever I talk to a founder I commit to being positive and being useful. It’s a tough journey where the entrepreneur is learning (and sometimes failing) in public. Until you’ve sat in that seat you should often keep your advice to yourself.

Elle: You are a pilot and I loved the plane you had. You don't have a lot of time to fly these days but when you do, what kind of plane would it be and where would you go?

Raymond: Remember that time we flew over Niagara Falls and you wanted a photo so I flipped the plane sideways so you could get a clearer view? The look on your face…

We’d all love to have a private jet for those weekends in Rome or New York. But what I love most is the freedom of flying a small plane, low and slow. You’re not isolated from the elements in some big metal bus, you’re part of the wind and the clouds and invisible currents. I love modern gadgets but there’s something romantic about using an egg timer to remind you when to switch fuel tanks (true story).

Elle: I've never asked anyone we've featured for In Conversation about our shoes but I feel like I have to ask you because there would not be a V men's loafer so quickly had you not asked me to make a pair for you. I also designed a two unisex sneakers which are named after you. Ironically, I'm the only one I know who has never called you Ray. How do you feel when you wear the Vs and Rays? You have all the colors and some custom ones too, what's your favorite color?

Raymond: I’ve never had more people comment on my shoes or stop me in the elevator to ask about them. The V loafers are really eye-catching but in a confident, understated way. They don’t scream for attention but they get it. They’re my new power shoe. Plus they’re so comfortable I feel like I can wear them around the house like slippers.

If I could stop you from selling the sneakers and keep them all to myself, I’d do it! I can wear the Rays on stage, in the boardroom or going out for dinner. You might laugh at this, but wearing them makes me feel seriously cool.

Elle: What does Walk How You Want mean to you?

Raymond: First of all, I love the woman who came up with this! To me, it says don’t just walk in other people’s footsteps. Make something new and make a difference. People are so afraid to be original. We’re so tuned in to how to perfectly fit in. Walk How You Want challenges that on a personal level.