Dennis (Dony) Zaidi

Dennis (Dony) Zaidi


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Venture Capital | ESG | Managing Director @ Checkmate Capital

Learning By Doing – Dennis (Dony) Zaidi

“Luck is when skill meets opportunity”


My passion is to help ventures that want to make the world a better place become big companies with even bigger impact.

Companies usually begin with little more than a dream: a concept, an idea, or an invention. But while hope, inspiration, and some personal savings can be the promising seed for a startup, it often takes much more to grow a concept into a thriving company; it takes venture finance.

I am a venture capital and private equity professional with 15 years of experience in a diverse array of verticals including energy, clean tech, agtech, and life sciences / health tech.

I strive to be the bridge between the world’s biggest dreams and the capital needed to make those dreams a reality. Along with embracing the lessons learned from having played a lead role in three successful exits, I also use a toolkit of formal entrepreneurship focused education from the world’s top universities (HEC Paris, Harvard, Oxford) and certification bodies to help founders achieve scalability and profitability.

I draw from a diverse array of advanced story telling skills to execute on this mission. As a certified data science professional and financial analyst, I can create clear financial models to communicate valuations and returns for even the most complex M&A transactions or disruptive business models. I have also won over eighteen international awards for films I have directed and use that skill set to help founders and funds create breath taking presentations and pitches that convert potential investors into highly invested business partners.

My efforts have helped raise more than 100M in equity, debt and LP investment. I have also led detailed diligence on over 50 deals, dissecting data rooms and interfacing with experts to ensure alignment and investment potential are tangible. But my work doesn’t stop after investment – for portfolio companies, I’ve helped CEOs increase revenue by over 100% while improving margins.

After receiving my Responsible Investment Professional Certification from RIA, I love to use my knowledge of Green & sustainable loan principles, Green bond principles, UN Sustainability Developments Goals, Climate bonds Initiative, TCFD, and other majors ESG regulations to help investors and limited partners achieve their wholistic investment objectives.

Do you share a passion for helping the world’s best ideas get the capital they need to fight disease, heal the climate, or create social and environmental impact? If so, let’s talk.



Dennis (Dony) Zaidi

The full #OPNAskAnAngel talk

Welcome. We’re super excited to have you join our asking angel. We might have to change that name because we’ve been interviewing angels and VCs all over the world, but we just call everybody angels. So maybe we’ll just be sticking with that and we won’t tell what an angel is, we’ll just say that all good people, um, but yeah. Welcome. And the best way to start is if you can share a little bit about your background, kind of your journey, what you’ve been up to, and where you are today…
For sure.
And then the only other ask is if you can share one thing about you that nobody would know.
All right, let’s go. Um, I come from I’m from I’m from just outside Toronto. Canadian, Um, Just grew up in Ancaster, just inside of Hamilton, sort of in the early stages of, you know, going twenties and thirties. Serial entrepreneur, a bunch of different verticals, everything from hospitality to, some land development projects to, uh, my dad was a huge environmental scientists and, you know, helping out on some cleantech initiatives, and really in love with entrepreneurship. I applied for a renewable energy permit here in Ontario on a what I thought was going to be a land development project and was awarded one of the Green Energy Act renewable energy permits. I was very surprised. I would love to say it was, you know, a whole bunch of planning and intelligence that led to that. But it was, you know, a significant component was locked, and so I had to learn a lot about renewable energy and ended up developing one of the largest solar farms in Canada. I monetize that project or the development work to a Panasonic anchored private equity firm called Corona Group. They were about a three quarter of a billion dollar fund. and I was sort of, you know, um, my first real exit if you want to call it that of significance. And it was pretty transformative from a personal like financial perspective. Gave me a bit of breathing room to sort of step back and think about what I wanted to do next. And so I actually went back to school, and I did my masters degree in entrepreneurship. The sort of process of exiting on that solar farm made me very aware of a lot of the gaps I had in my skill set.
And I ended up being on the project, kind of the de facto finance guy. And I use that term really, really sort of, you know, that these are intentionally, you know, quotation marks around it. I had no clue what I was doing. It was baptism by fire. You know, I stepped into my first meeting or one of my first meetings to finance the project, and they were discussing, you know, some guy was discussing with me the terms of debt surrounding the project he was talking about live or And I literally thought LIBOR was a guy. So I went home and was like Googling who is this LIBOR? And it was like, okay, that’s the London interbank exchange rate. Okay? And I don’t know, I don’t know, you know, it was very humbling the process. So anyways, I went back to school and I thought it was a great chance to fill in some gaps.
And so I focused on venture finance within a masters degree in entrepreneurship. Uh, And so coming out the other side of that, the gentleman who was running, uh, managing partner at Coronal, who bought my solar farm. He did really well at Coronal and sort of transitioned off and had been investing on his own as an angel. And thought it was time decided to take it to the next level and start his own fund.
And when he was looking back along his journey, um, he was sort of looking for people who he got along well with and respected and amazingly, asked me to come join him. And that was sort of the genesis of my joining Checkmate Capital. And so for the past two years, I I moved from entrepreneurship to the dark side of Venture Finance, and I’ve been working with checkmate capital as a partner, put my own money in, and off we go. And, uh, so, you know, we’re sort of somewhere between a family office and a venture capital fund.
We do take investment, but we also are definitely unlike a venture capital fund. We use mostly our own money. We have a few different verticals that we invest in. I guess we’re just a group of guys that got together and really love supporting entrepreneurs. And so if you can convince the guys something’s good, we’ll invest in it. But that seems to fall along our personal interests.
And so everyone on the team is interested in, You know, I think we all have big hearts, so we tend to invest in things that help people like health and healthcare and healthtech, biocide drugs that have the potential to change people’s lives in a positive way. We also have sort of this renewed sustainability lens where we like agtech, we like, waste to energy, waste to resource, we tend to take a view that things that are being thrown away are cheap to get. And if you can turn them to something of high value, then that’s a great business model. Uh, and that sort of seems to be the lens personal lens. And I guess checkmate funds around are sort of investment thesis. A