Jacky Chen

Jacky Chen


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Managing Partner – Roadster Capital

Listening and sharing – Jacky Chen

“I’d rather hire one strong guy instead of two or three average people because, in a startup, you compete with your competitors; they are well established.”


Jacky Chen is dedicated to angel investment since 2014 and has built up a portfolio of more than thirty startup companies in Canada and the US. His target investments are the startups with disruptive technologies and business potential in the industries of enterprise software, ICT, AI, MedTech, and Advanced Manufacturing.

Jacky has acquired concrete business experiences as a successful founder in the startup ecosystem and an executive of Fortune 500 companies over two decades. His remarkable accomplishments range from building startups from scratch to leading a billion-dollar business with leverage of 14,000 enterprise channel partners.

The unique journey has shaped Jacky’s outstanding of investing in early startups. Jacky holds the degrees of Mater’s E.E. and MBA, and he graduated from CEIBS and The Wharton Business School of the University of Pennsylvania.



Jacky Chen

The full #OPNAskAnAngel talk

Jeffery: Yeah, I’m glad you’re able to join us today, Jacky! So, you know what, the way we like to do it and we’re already started, so it’s great. We like to jump right into things. So welcome to Ask An Angel, and today we’re with Jacky Chen, the Jackie Chan. And you know, the best way for us to start Jacky, is if you can share a little bit about your background, kind of where you’ve come from, where you’re at today, and then one thing about you that nobody will know.

Jacky: So my name is Jacky Chen. I’m an Angel investor and also a entrepreneur, and executive for 14500, formally. And my background is in enterprise, IT industry for more than two decades, and I also started my own business. I was pretty lucky enough. Got my business acquired by their Compellent in 2011, so I think I jumped into dealing after a few years of a lockup, I’m jumping into Angel investment ecosystem. Today, I’m a general partner of Archangel fund, and also our managing partner, managing director of wedding alumni angels. So I’m pretty enjoying, enjoy investing!

Jeffery: Awesome! Well we’re excited to have you today and before we do, you got to give us one thing about you that nobody will know.

Jacky: It’s pretty challenging. I believe no much secret on that, so I believe Angel investment is more about being an angel investor. More important is your industry business experience. It’s pretty different from PEVC later stage, right? And causing early stage, no much data. You judge everything with a scratch, even no scratch based on business experience. So I believe, Angel investor is more challenging than that stage PE, or VC and PE. Probably, somebody else may not agree with that but it’s true.

Jeffery: Well, there’s a lot of risk, so we’re in the highest risk category you can possibly get into, I guess, when it comes to companies being early. So I do agree with you that, it is completely different. One is based off metrics and lots of metrics, and the other one is based of gut and little metrics. So there’s a good fine balance there. So I’d love to kind of go back to a little bit of your background because I always believe that a background is what shapes the investor, and you know, going back to your time when you were working in IT, from CIBC, to EMC, all in that fintech. Well, I guess, we call it fintech back then. It’s just financial industry but going into those areas and then driving into you know big data corporation, and all of the companies that you worked in, how do you take that IT side of things and how do you think the learning shaped what you do today? And I guess starting by the data side of it, understanding the finance, what learnings do you think that you picked up on that really helped you today in being able to see a great startup and jump in to make those investments? What kind of skills did you bring to the table when you were younger?

Jacky: Yeah, for, I’m pretty lucky in different industry and different companies. The great companies, and for like CIBC you can have like industrial financial business background in that vertical industry, right? So for like EMC, actually, I helped the EMC, started their business in China as a very small group, then help compellent to land their business in Ash Pack, as the first guy, and the McData, the same thing. Then at that time, I, especially working with Mcdadda a Colorado based public company, then I started their business in China from scratch like one guy just with one laptop, that’s all resource I have then, I fly back from North America to China to start the business. After the five years, the business growing very quickly, dramatically, in China. We still establish a leadership in different vertical industries like finance banking, telco, and government then that business wouldn’t be growing pretty. Well after five years I went the whole cycle from the first person to start a business in regional business then grew a big team. Tremendous business then McData got acquired globally after five years, then I got a chance to learn how to transit business to merge period. So then the business cycle, I learned the business cycle, I decided to build my own business. Though a lot of opportunities offered in the market to be like have me try to be executive managing director for Ash Pack, or China, Hong Kong like that. I didn’t move that direction, I moved to entrepreneur. I like start something from scratch.

Jeffery: And did that come from your experience, when you started that company with one laptop in China, was that where kind of got you excited? Was that you were able to take this business even if it was a shell, and a license, and starting it, that was really what drove you to want to become an entrepreneur?

Jacky: Yeah, that’s true. Because I have been the cycle with, like our startup with the American company, the strong support from headquarters side, right? But that gave me a sense, how a startup works, then step by step build up your team, build up your business, then get achievement. Then I was pretty comfortable to starting my own business. That’s the way I decided, “Don’t go anymore to be another country manager or some Ash Pack executive. Just start my own business.”

Jeffery: So that experience really helped you better understand the startup world and then put together all of the elements that you needed. Regardless of, say how it was funded at the time, but your strength came from being able to be a general manager and then seeing down, and learning all of the different ropes in the business or different verticals, and then being in there and working your way up. You kind of had to build it from scratch, learn all these different facets, so it really gave you a really good understanding of what it takes to build a company from nothing.

Jacky: Right, exactly. So a lot of the things to learn and I, as I said, I was pretty lucky in work with big companies, leading companies, global, with global business like McData, EMC, and also Dell, those are great companies. They give you training nowhere you can find. This kind of training, for executive training it’s very different for normal employee. Executive training, they will put you somewhere to build how the global business work. You have a lot of insight. They’re really helpful.

Jeffery: So would you recommend to the audience, to entrepreneurs, that it’s not always about jumping in right away into a company without any experience, that it actually carries a lot of value to go and work for a big company, learn the problems, learn the things that are going on in the world before you jump into entrep