Social Impact Investors: How Tim Carwell of Indigenous-led Dreams Tree Community Investments Is Helping To Empower Underrepresented Communities

Long term Impact : There’s a vision focused on creating a business that lasts, not just focused on quick return for investors. When a company has a social mandate woven into the opportunity, this is extremely important for me to know. I definitely want to understand the impact of a quick return to the social mission. Honestly though, if the point is to get in and get out the opportunity most likely is just another slick business school opportunist that sees a benefit of pretending to “show up” for a social cause when in reality their real motive is personal enrichment.

As a part of our series about “Social Impact Investors”, I had the pleasure of interviewing Tim Carwell.

Tim Carwell is an entrepreneur, investor, and community advocate, serving as the President of The CommAlert Group. A proud citizen of Beaver First Nation, he is recognized for his dedication to social entrepreneurship, focusing on initiatives that promote goodwill and elevate the visibility of underrepresented communities.

Thank you so much for doing this with us! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

My career path is deeply rooted in a desire to honour my mother’s resilience as a survivor of the Sixties Scoop. For those unfamiliar, this was a devastating period in Canadian history where Indigenous children were forcibly removed from their families and placed in non-Indigenous homes. At the age of 4, my mother was taken and separated from her family for over three decades. She endured unspeakable abuse and mistreatment in her early life, experiences she didn’t pass on to my siblings and I. This is a much longer story (which readers can learn more about at dreamstree.ca). In short, I’m driven to repay her gift of unconditional love and kindness. single. day. My commitment has only deepened since her passing last year.

Beyond that, I think my career path stems from genuine curiosity and a tendency to embrace opportunities as they arise. I’ve sort of lived in the moment and looked at opportunities as a blessing. I would describe myself as both inventive and adventurous, though not a risk-taker. I dedicate significant time to honing my existing skills and tend to focus on areas that genuinely interest me. If an investment, business, or subject sparks my interest, I am motivated to pursue it.

Can you share a story with us about the most humorous mistake you made when you were first starting? What lesson or take-away did you learn from that?

When I very first got my first sales job, I secured this big print campaign which was worth a lot of money, and I was like the hero of the office. Everyone loved me, and my head got pretty big. I was quite proud of myself.

After getting awarded this contract, I was asked to do a small mailer project that nobody cared about, including me. I didn’t give it the focus it needed, and we ended up having to do a second run.

Some time later, I got a phone call from the large client I had recently secured. This nice lady said, “We have just awarded you this huge project which is very high profile, and you can’t manage this small project that’s not even a tenth of the cost. I think we’re going to pull our contract.”

I couldn’t believe it. I didn’t want to tell anybody in the office, so I got my suit on and headed off to save the deal. I showed up unannounced, knocked on the door of the boardroom she was in and I fessed up to my mistakes. I explained this wasn’t a reflection of the organization, but on me. I told her about our amazing team and how they were as committed to the success of this project as I was — that if they could see their way to give a second chance, I wouldn’t embarrass them and we would deliver success.

The client looked at me and said, “It took a lot of courage for you to come over and speak the way you did. A lot of people would have made excuses or blamed others, but you took it on, and we appreciate that. But if I could give you one piece of advice, …before you rush over, …make sure your fly isn’t undone.”

I looked down, and I had a blue suit and a white shirt, and my white shirt was sticking out of my zipper.

As we roared with laughter, I knew I had saved the deal. I don’t regret running over there, but now if I’m heading somewhere important, I always make sure my zipper is up.

Are you able to identify a “tipping point” in your career when you started to see success? Did you start doing anything different? Are there takeaways or lessons that others can learn from that?

It wasn’t one specific event, more of a gradual process. It’s like that old saying: ‘an overnight success that took 20 years.’ Some milestones, like moving from my living room to my first office, were significant. Those small, tangible steps forward were motivating, and I appreciate celebrating those. The takeaway for me? Don’t forget to celebrate incremental changes.

Beyond that I believe two key takeaways:

Firstly, be unapologetically yourself. If you can’t be that then the second takeaway is irrelevant.

Secondly, focus on your strength(s). Don’t waste time on areas that don’t create a spark. I never subscribed to the idea that one has to be good at everything. Being a generalist never appealed to me. That’s not to say that a moderate level of competence isn’t required. Nor am I saying that a person doesn’t need to pay attention to the details.

None of us are able to achieve success without some help along the way. Is there a particular person or mentor to whom you are grateful who helped get you to where you are? Can you share a story about that?

I’ve been asked this many times, and my answer, though about one person, doesn’t discount the many mentors I’ve been fortunate to work with. The first one who set me in the direction and gave me the confidence to believe in my ability as a businessperson was Rick Baron.

I first met him while I was in school. Funny story: I was a broke student and took a job as a karaoke singer — an awful job, I can’t believe I’m admitting it, but I needed the money. So I took the job. I met Rick, and it was kind of funny. I didn’t think we would ever build a relationship because the first time I met him, he was actually heckling me, teasing me about being a karaoke singer and the songs I was picking. But what he failed to realize is that I’m good in front of a mic and not scared to talk in front of people. I had the mic; he had to sit there and listen to me tease him.

I basically got the whole audience against him like I was a comedian and he was a heckler. It was funny, and I enjoyed it; I’m not sure he did. But a few weeks later, he ended up showing back up at this place where I was singing and MCing, I guess they call it. Anyway, long story short, we developed a relationship over time.

I was 24 when my dad passed away and I spent a lot of time with Rick trying to make sense of the loss. I don’t remember how it transitioned, but he asked if I’d be interested in pursuing a career in sales and marketing because I seemed “pretty quick on my feet and could engage people”. He was the one that introduced me to the internet way back. Yeah, it was blind faith, trust, or just a respect that he and I had for each other. I remember him talking about wanting me to move into this role working on the internet in the days of 56k modems when you had to type in the url to find companies online — there was no Yahoo or anything; this was just past Netscape. I had no idea that the guy I insulted at karaoke was a visionary leader of a new economy that a lot of people were just grasping to understand. There is no doubt he changed the trajectory of my life.

You have been blessed with great success in a career path that many have attempted, but eventually gave up on. Do you have any words of advice for others who may want to embark on this career path but are afraid of the prospect of failure?

All of the success I’ve had comes from being around incredible people who tolerated my personality and were willing to take risks with me. A lot of it was dumb luck and timing.

Make no mistake, I have failed and continue to fail. There are investments that don’t work out and projects that don’t go as anticipated, resulting in lost money. But I’ve avoided big failures because I don’t fall in love with material things… and I’ve never been willing to sacrifice the people who I work with due to pride or money.

My wife gave me a valuable perspective: if we lost everything, could we rely on friends and family? The answer was yes, which relieved a lot of fear, and gives us space to fail. It also doesn’t hurt that she’s successful business leader in her own right which I suppose affords me the opportunity to become a short and chubby “trophy husband.”

Let’s now jump to the main part of our discussion. You are a VC who is focused on investments that are making a positive social impact. Can you share with us a bit about the projects and companies you have focused on, and look to focus on in the future?

When it comes to investments focused on positive social impact, we really engage in two distinct types.

One type is what you might call a more typical investment, requiring standard due diligence and discovery strategies. Nowadays, we are increasingly focusing on businesses that have a solid understanding of social enterprise — specifically, how they plan to utilize a percentage of their profits or EBITDA to contribute positively. These are particularly interesting to me because they embody a focus on community and the idea of lifting each other up. As a First Nations person, it’s important for me to invest in people who think beyond just the almighty dollar and consider their community.

The other type of investment we make is through our community investment group, called Dreams Tree Community Investments. With Dreams Tree, the core principle is that the investment is the return, and we do this in two streams. Firstly, gifts that unlock connection and wellbeing and secondly, investing in experts to share traditional Indigenous knowledge.

We spend a significant amount of time visiting remote communities, sitting with First Nations Elders and people who hold generations of knowledge in my own territory in northern Alberta, Treaty 8, and across the country. We are gifted with this incredible wisdom and knowledge. When a moment arises to pay that back, whether it’s by investing directly in language and culture programs, or supporting an entrepreneur who is also a knowledge keeper, we do that.

The community investments through Dreams Tree definitely involve more ‘heavy lifting’ than traditional investment; that’s simply the nature of that work. The value isn’t financial — it just feels profoundly good to be able to pay back knowledge that you never thought you’d have the opportunity to repay.

What you are doing is not very common. Was there an “Aha Moment” that made you decide that you were going to focus on social impact investing? Can you share the story with us?

There was never an “aha moment.” It wasn’t a decision or a choice; I was born this way. It’s just part of my DNA I suppose. My perspective has always been that if I am doing well and my community isn’t, then I’m not truly doing well. My life has been a balancing act of participating in wealth creation while striving to remember that when I’m at my best, I am a humble servant, regardless of whether I’m investing or not. In fact, there have been more than a few occasions when I have passed on a monetary investment but not on the person or people seeking funding. It’s important that I mention that these relationships are without agenda. I’m not waiting for “the business” to mature so I can swoop in and invest at a later date.

It’s also why I don’t think of myself as an “investor”, or “donor” but as a man that is curious to uncover how he can make an impact. That’s why our investments are not focused solely on the Indigenous community, but on any community or business with a purpose beyond the bottom line. Probably why I gravitated toward social impact investing so effortlessly. To be honest, I’m really glad someone finally came up with the terms “social impact” and “social enterprise,” because I used to call myself a “social capitalist,” which makes zero sense but did get a few laughs and odd looks from time to time.

Can you share a story with us about your most successful Angel or VC investment? Or an investment that you are most proud of? What was its lesson?

The investment I’m most proud of is investing in a mobile planetarium which enables a very good friend of mine, George Dejarlay, to share his star stories — specifically his Cree star stories — with a much larger audience. This isn’t just about reaching more First Nations people, but also individuals curious about how we navigated Turtle Island, North America, before European settlement.

George is a deeply knowledgeable and patient person. Our friendship developed through many conversations, and I learned so much from him. I honestly never thought I would be able to repay the gifts he gave me, but in a way, I have been able to. The mobile planetarium gives George access to a wider market for his work.

But what’s most important, what truly makes me happiest, is that it provides an easy way for Indigenous and non-Indigenous individuals to sit together and learn about each other in the spirit of reciprocity. This is more powerful than the language of reconciliation, which, frankly, I’m not sure holds the same meaning it did even just a decade ago. Reconciliation, as often discussed, can feel divisive, leaving individuals who don’t share the same history and stories as my family and others like mine feeling ashamed, angry, and separated.

Investing in initiatives like this, where people can simply gather and learn — in this case, about the stars — brings us closer together. It lays the groundwork for having more meaningful and deep conversations down the line. Ultimately, I am grateful to have learned the lesson of reciprocity by investing in George and his work.

Can you share a story of an Angel or VC funding failure of yours? What was its lesson?

Oh god yes. Funny thing though, no matter what story I share, it’s always the same story. It basically goes one of two ways. Either, I don’t trust my gut and walk away or I dismiss the red flags that a colleague uncovers. In both scenarios I become an arrogant interpreter of information that tries to make sense of the unease myself and others may be feeling. Ultimately this means time and so many brain cells get wasted trying to justify why we should proceed. Basically, allowing myself and others to be convinced that we misinterpreted the situation.

What have I learned? Once the situation reveals itself, believe it.

Is there a company that you turned down, but now regret? Can you share the story? What lesson did you learn from that story?

This may sound like a cop-out, but I don’t really see the world in those terms. I don’t spend one second looking back and living in the “shoulda, coulda, woulda’s”; I find it a total waste of time. Things happen exactly the way they are supposed to. I believe that a person’s involvement (or lack thereof) changes the outcome… good and bad.

Super. Here is the main question of this interview. What are your “5 things I need to see before making a VC investment” and why? Please share a story or example for each.

Here are my five non-negotiables:

1. Values, Values, Values: Beyond the obvious due diligence, the choice to invest or not centers around values alignment. All things being equal, if our values don’t align I don’t invest. Nothing annoys me more than the arrogance of a founder who “shows up” and tries to camouflage their offering with business/tech speak. The days of just “take risks and ship it” are long gone. That’s why I dislike the overuse of the word MVP. I’ve seen many “MVPs” that turn out to be NVPs (Not Viable Products) because the founder spent more time justifying (or worse, hiding) a bad idea.

2. A balanced offering: The opportunity makes sense from a social and investment perspective equally. I believe theirs a clear path to growth on both fronts. I’m the first to admit that I can be swayed by a strong “social mission” and momentarily forget that my larger goal is to ensure an investment produces both the desired social impact AND a healthy return equally. Likewise, a company with an inauthentic social mission is also a risky investment. If I don’t see balance, I don’t invest.

3. The People: I’m inspired to invest when I witness the collective skills of the team and how they work together. I need to feel confident that when difficulties arise (and they always do) that the team isn’t going to implode but rather rally together to fix whatever the challenge may be

4. Entrepreneurial mindset: There’s a growth-oriented entrepreneurial mindset that permeates throughout the organization. Big words I know but it is critical that the founders and early employees (and investors I suppose) have an environment that nurtures confidence and encourages diverse perspectives to be heard. I am firmly convinced that there are waaaaaay too many tech bros that in a lot of cities communities have become echo chambers… The same people saying the same things and telling each other they’re innovative.

5. Long term Impact : There’s a vision focused on creating a business that lasts, not just focused on quick return for investors. When a company has a social mandate woven into the opportunity, this is extremely important for me to know. I definitely want to understand the impact of a quick return to the social mission. Honestly though, if the point is to get in and get out the opportunity most likely is just another slick business school opportunist that sees a benefit of pretending to “show up” for a social cause when in reality their real motive is personal enrichment.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I would love to inspire a movement of good by sharing the fundamentals of Indigenous ways of being. This is simply living in the moment — present and there for others. The tricky part is to move without expectation or agenda. Hard to do but not impossible.

If you could tell other young people one thing about why they should consider making a positive impact, like you, what would you tell them?

What I can promise you is that there is nothing more rewarding than being part of something bigger than yourself, whether it’s working alongside the founder of something new or volunteering with a well-established organization that needs help. As long as it resonates with your heart, that’s all that matters.

Now more than ever, people across the world are searching for meaning and purpose. Some have already begun creating projects that, given enough support, will produce a ripple effect of goodwill with lasting effects in their community and perhaps across the world. They are overwhelmed with a project they are trying to get off the ground and could use an extra set of hands — your hands.

We are very blessed that a lot of amazing founders and social impact organizations read this column. Is there a person in the world with whom you’d like to have a private breakfast or lunch with, and why? He or she might just see this.

With the current state of the world, I would probably want to sit down with Mark Carney, our new Prime Minister, to discuss the economic opportunities he envisions through partnerships with Indigenous communities and to share some of my own perspectives. From an outsider’s viewpoint, he appears to be an incredibly gifted statesman with a once-in-a-generation intellect. Time will reveal the full extent of his impact and influence, but he seems to possess the skillset and experience to reshape global perceptions of Canada and its diverse population.

I sincerely hope he reads this. I believe I’ve offered sufficient flattery (some might call it sucking up) to warrant a private breakfast, or at the very least, a photo opportunity with him, elbows up, at a Tim Hortons.

How can our readers follow you online?

Connect with me on LinkedIn https://www.linkedin.com/in/timcarwell/ and learn more at https://thedreamstree.com/

Thank you so much for this. This was very inspirational, and we wish you only continued success!

Social Impact Investors: How Tim Carwell of Indigenous-led Dreams Tree Community Investments Is… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.