CAN-AM Stories – Entrepreneurship Across the Border: Darlene Damm

In partnership with The U.S. Embassy in Canada, Startup Canada is celebrating and spotlighting women’s entrepreneurship across the border – speaking to leading founders to learn more about their journeys, and the vital role of cross-border collaboration on their entrepreneurial successes. Startup Canada was pleased to sit down with Darlene Damm, innovation specialist and American founder, to learn more about their journey.  

Darlene Damm is the VP of Community and Impact at Singularity Group. Darlene has a broad background spanning across both technology and social change. In 2012 she founded DIYROCKETS, the first company to crowdsource space technology, and in 2011 was an early co-founder of Matternet, one of the world’s first companies using drones for commercial transport and delivery of medical goods. Darlene served with Ashoka, the world’s largest association of social entrepreneurs, for nearly ten years where she built the organisation’s fundraising system and led Ashoka’s presence in the Silicon Valley. Prior to that, Darlene spent over a decade working in Vietnam, Myanmar, Indonesia, East Asia and the US on educational and economic programs that empowered youth and helped bring developing nations into the global economy.

SC: Tell us about you and your businesses! Who are you and why did you start your business?

I’m the Vice President of Community and Impact at Singularity Group. I have founded companies in my career, but currently work at Singularity supporting 1000’s of innovators from around the world to help them launch and grow their ventures or transform their companies or organisations. Singularity was founded over 10 years ago, by Peter Diamandis and Ray Kurzweil, to help ‘futuremakers’ understand how exponential technologies can be used to solve our world’s biggest social challenges. Exponential technologies follow a price performance curve where they become more powerful and scale exponentially while also becoming cheaper and more accessible. A lot of our world’s social problems are big – they’re complicated and expensive. Singularity was founded on the premise that we could help the world understand how to use these technologies to solve problems that we couldn’t previously solve. 

SC: What’s been your greatest success so far?

I am most proud that throughout my life I have always tried to find the hardest and most meaningful problems to work on – even if it seemed unlikely I would succeed.  When I was younger, this meant working in countries like Vietnam and Myanmar at a time when many people believed the problems in the country were too difficult to solve. Later, I worked on companies and experiments in the aerospace industry, and today work on a wide variety of challenges – from trying to help victims in Ukraine access bionic arms to helping a refugee settlement in East Africa access clean wind energy. 

SC: What is the best part of Canada’s and America’s startup ecosystem and community?

The best part of the US and Canada ecosystem for me is the people and the creativity that they bring – their willingness to solve really important and hard challenges. I first came to Singularity as a student over 10 years ago, and I remember one of our faculty was from Canada working on quantum computing. That really inspired me. Today we’re still working with innovators in Canada on quantum technologies and using synthetic biology to make sure that water is clean. I’m just really hopeful that we have the tools now to solve these problems. Today, it’s more about just finding the innovators who believe they can do it.

SC: In one sentence, what does being a woman entrepreneur mean to you?

Being a woman entrepreneur means that I can go out and literally build new companies, organisations, and institutions that will change the world for the better in a way that’s not just better for the benefit of women – but for the entire world. I don’t have to ask for permission.   

SC: How has the pandemic impacted your business?

We had to pivot a lot of our work to helping people digitally. The pandemic, in many ways, brought us into the future – a future that we predicted was coming – but was still a big challenge, nonetheless. 

SC: What has been your biggest struggle in navigating cross-border sales and operations?

Singularity itself works with innovators, faculty experts, and partners across borders – that has all worked out well. But the opportunity I think we miss is that we have so many innovators just trying to get off the ground that they haven’t even begun to think of potential markets for their product. So they’re really just at the beginning of just knowing that an opportunity – like sales in Canada – is available to them. 

We actually looked at our numbers a few years back and most of our founders – approximately 80% – were women with venture backed companies. That’s an astronomical number to have achieved. But for women to really build companies that change the world, they need to be able to scale and they need to be operating globally. So being able to export products to Canada, or vice versa, is so important to being able to grow your company at that level.

SC: On the other hand, what are the biggest benefits you see in cross-border sales and operations?

With the US and Canada’s shared borders, we see a lot of the same social challenges. At Singularity, we focus on using technology to solve the world’s biggest challenges. Just from growing up on the West Coast, I know that Western Canada is also dealing with wildfires right now. But there are actually a lot of different technologies that can be used to help here such as detecting fire outbreaks from space, using artificial intelligence to create better evacuation plans, and creating more resilient homes. The same thing can be said for protecting our oceans or addressing climate change. I think there is a huge opportunity right now in looking at how we are collectively addressing these challenges, the technologies we are using to help, and then sharing this information across borders with other continents. It feels like there is so much potential in terms of what we can do and achieve together if we really dig in. 

SC: Has going global given you an advantage in bouncing back better and faster amid the pandemic?

Singularity has always been a global organisation from the start and that definitely positioned us well during the pandemic. We have diversification so people can work in different parts of the world while some areas are better off than others. You can find more opportunities with a global network. More importantly, however, is that we believe if we want to solve these big problems – like a pandemic or another global issue – we need everyone around the globe working on these problems. We can’t just have 10% of the world working on these problems together – we need the brainpower of the collective. As a global company, that’s a big advantage. The answers are in the minds of people who are currently all over the world, so how do we create systems and processes where all of those different people have a chance to bring their solutions to life?

SC: Many women founders have cited mentorship as the biggest support in growing successful businesses. Have you found value in mentorship, either as a mentor or as a mentee?

Yes, yes. Early in my career, there were a lot of people who really made a difference. I grew up in a rural town of about 2000 people and my neighbour in that very small town happened to work with Robert Goddard building the world’s first liquid fueled rockets. So for me, before I even went to school, somebody had shown me that you can change the world and you can do the impossible. That experience was also powerful for me because when I heard the stories firsthand, it wasn’t just Robert Goddard, but his wife Esther Goddard who would have been considered a co-founder today. She played a role in building the recovery systems for the rockets, did fundraising, and filed the patents. So I had people introduce to me at a very young age to what is possible. 

Later in life when I was working in more cutting-edge technologies that hadn’t been used before – like new medical transportation technologies or 3D printed rocket engines. I found that people were more likely to tell you something wouldn’t work. With new technologies, nobody knows if they will work or not. So in that particular instance instead of listening to a mentor, it’s better to actually try it and see if it will work or work with other peers who are in that same space. If you really want to move something forward, sometimes you need to take a chance.  

SC: Have you ever experienced running into a problem where seeking mentorship or advisory support has helped guide or empower you to find a solution?

Yes! When I was in graduate school studying Southeast Asian studies, the Cambodian ambassador to the US, Ambassador Roland Eng, gave a lecture in one of our classes. I reached out to him afterwards and actually asked “would you be my mentor? I’m really interested in furthering relations between the US and Southeast Asia”. He was incredibly generous and started inviting me to different events and meetings he was having, asked me to write a chapter in a book he was working on, and much more. I think the biggest game changer though was having a first-hand look into what his job looked like. I was able to see the reality of it – not just what you can read about or what’s in the news. It gave me the confidence to go and work further in Southeast Asia on international relations. 

SC: What does being part of this partnership mean to you? What do you hope to achieve?

I think it’s a really interesting experience to be able to look at and think about the real challenges innovators face when exporting or importing. As someone who has worked with technologies most of my life, I understand the regulations are already written and can be extremely complicated to navigate. The question that is always on my mind is how can we balance innovation with regulations – making sure that things are safe, and that these technologies are built in the best possible way for the benefit of people and planet. I think there are a lot of ways we can simplify this process and make it easier, in addition to influencing how the different technologies we develop are good for the world not just today, but in the long term. 

SC: How can we learn more about your journey and organisation?

I’m on LinkedIn – I share a lot about my own work and Singularity’s work, but also about our different innovators and partners and what they’re doing around the world. Singularity also publishes a news site called Singularity Hub with a lot of great content. Our website also has a lot of information and resources.

SC: What advice would you give to women entrepreneurs who are ready to go global and take their first steps exporting?

I think it’s really important for women to realise that nobody’s in charge, actually, of anything. If you want to go far in the world right now, it’s important to recognize that the rules we have in our heads are not real. Take me, for example. I was a history major who worked in the non-profit sector then switched to the aerospace industry, and now I teach people how to use innovative technology. Throughout that entire journey, based on the advice that other people gave me when I was younger, I shouldn’t have been there. I realised there’s always a way to make changes and figure out what you want to do as you go. A lot of that is not allowing yourself to see limits – think beyond them about what really matters at the end. For me, I was hugely motivated by the idea of solving big problems our world faces. If I needed to learn how to use technology to get there, then that’s what I’ll do. The process and the “rules” are much more open and flexible than we like to think. 

SC: Do you have any recommendations on how women founders can expand and capitalize on their network to help them on their journey?

As an entrepreneur, solve a problem that matters. If people see how what you’re doing will make their work life, family life, and the world in general a better place, they will want to help you and are already a part of your team. Maybe not formally, but still – think of everyone you work with as your team. Your idea, coupled with your team, will make the world a better place. Innovators, especially women innovators, are so needed in today’s world. Every single one of them. So even if it seems hard, daunting, and like nobody understands what you’re doing, just keep going. Someday they will understand your vision, but your insights are needed now. 

SC: Thanks so much for talking with us today, Darlene! 

Thank you!

This piece is part of Startup Canada’s wider campaign in part with the U.S. Embassy in Canada to celebrate and honour incredible women entrepreneurs from both sides of the border. If you are a woman-identifying founder in Canada or the United States looking for free one-on-one advisory support from expert mentors, private sector partners, or startup support organisations, head over to to learn more and get started today.