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In conversation with Jason Sawyer, Co-founder of Caary
November 1, 2021

Jason Sawyer is Co-founder of Caary. Jason’s career spans the gamut of alternative investments – venture capital, private equity, and hedge funds – so he knows a thing or two about financing and launching a business! That’s not just a boon for Caary, but for the 1.2 million small-and-medium-sized enterprises (SMEs) across Canada Caary intends to support. Here’s Jason on the Caary journey, with tips for entrepreneurs and business owners on the growth track:

Q: Can you tell me a little bit about your background and how that eventually led you to the Caary venture?

I have spent my entire career in alternative investments, assessing, financing, and advising venture and early-stage growth companies. The success of which has his family situated as a quasi-institutional investor. Given that, we had been talking about setting up a venture fund with our own capital and utilizing my experience in raising significant assets for various types of alternative asset managers. We had both financed and operated small businesses through various stages of growth. As we assessed the market in Canada and examined and contrasted it with trends in the U.S., we elected to start Caary, to build a core operating business within a totally underserved market. We’ll sponsor hundreds – and soon thousands – of entrepreneurs and established SMEs via our unique credit, payments, and financial operating platform, rather than through a traditional venture fund or family office investment vehicle, where we might fund 3-5 ventures per year.

Q: You have been a part of many successful ventures. What sets Caary apart?

There are two things. 

In my career I’ve seen some incredible companies as they’ve taken shape. I’ve had a ringside seat to considerable successes, watching right from that initial entrepreneurial spark through financings, operational execution, market entry, intense ramp-up and, in many cases, huge exits. Over that timeframe – and we’re talking about having viewed or been pitched literally thousands of companies and opportunities – I can tell you I have never seen a better-timed market entry, larger target addressable market with obvious problems and pain points and now a simple yet sophisticated, comprehensive, and easily accessible solution; Caary. 

Commensurately, we have this incredible team with the prior career accomplishments, depth of experience, and very specific skill sets with which to execute a business plan and to set-up to dominate a high-growth segment. Less than two years into its journey, Caary already has synergistic senior talent from large blue-chip companies mixed with entrepreneurial, venture finance and start-up expertise; this is a recipe for success and, frankly, the opportunity to achieve greatness. There is as much upside in this venture for Caary and its stakeholders as there now is for the SME business community in Canada.

Q: What’s the big picture view for Caary? 

Well, first, I like this question more than any question that you could possibly ask because this is about who we are at our core and what drives us.  When you talk about the millions of businesses that exist in North America – large or small – every one of them started with a person and a thought – an idea, concept, and usually considerable conviction. 

Caary’s noble purpose is to utilize our collective understanding of the entrepreneurial journey and, through our unique platform, deliver efficient access to capital combined with timesaving, integrated processes to support and drive business owners in pursuing excellence. We will get behind these entrepreneurs in a way that’s never been done before, specifically alleviating pain points and frustration from everyday processes and handing them back time to do what they do best for their customers. And we get to exude that conviction every day in the ongoing evolution and iterations of our platform and through our inspired version of customer success. 

Q: What’s been your primary focus as you have built Caary?

While we are focused on building Caary quickly and efficiently because we know this is a race to enter and attract customers in this brand-new market segment in Canada, we also expect and welcome competition because the market opportunity is so significant, and the SME segment is so underserved. 

Our primary focus has been building this business at the highest quality level but in the most capital-efficient way possible. I can tell you unequivocally, from the scores of businesses I’ve financed or been involved with, I’ve never seen a more committed team and capital-efficient exercise in developing and launching something this practical and useful, yet complex and game-changing.  

Q: From your experience in alternative investments, what advice would you give to other entrepreneurs / small-medium sized business owners about accessing capital?

First, study what motivates and drives investor decisions in your space and how your companies in your sector have gone about reaching those investors, at what valuations and in what structures and forms. There are methods now like crowdfunding platforms, innovation hubs, and angel networks that are becoming more and more prevalent and providing a collaborative environment for capital raising where there are also considerable mentorship opportunities. These can be utilized before or in conjunction with taking the friends & family and traditional VC approach. Although Caary is about as high calibre as a VC investment opportunity gets, we elected to utilize the expertise we had access to, to seize on the considerable momentum in crowdfunding as a component of our capitalization plan, as we continue our dialogue with some of the most prominent VCs and growth equity shops in the world. This gives us optionality at every stage of our growth and capitalization. 

Be cognizant of the various ways you can efficiently capitalize your business. One of the things that Caary will do for many cardholders is provide the credit (and soon other types of capital) that bridges the gap that equity or expensive credit lines might otherwise have to fill. Caary will enable companies to access credit quickly and efficiently, avoiding more expensive or dilutive options. Apply for a Caary card and take your business journey forward with us!

For more information or to sign up for a Caary card, join our waitlist. Interested in becoming a Caary investor? Watch this space for updates or email us at investors@Caary.com