Lean Out with Tara Henley

Lean Out with Tara Henley

Transcript: Daniel Debow

An interview with the chair of the board of Build Canada

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Tara Henley
Nov 05, 2025
∙ Paid

It’s budget day here in Canada. As Prime Minister Mark Carney’s government tables its first federal budget, we will get reaction and hear a lot of different visions for the country. On today’s episode we wanted to bring you one. My guest on the program says that Canada is in crisis — and that it is now time for “bold adventurism.”

Daniel Debow is a Canadian executive, investor, and educator. He is the chair of the board for Build Canada.

This is an edited transcript for paid subscribers. You can listen to the interview here.


TH: It’s great to have you on the show. We often talk to journalists and academics and authors. I don’t have a lot of contact with tech or the business world. But a recent guest of mine said that I just had to speak with you and that you are actively grappling with one of the main questions of this show. Which is: What’s happened to Canada? And what do we do about it? Let’s start today with your diagnosis. Where are we at?

DD: Where are we at? Well, I think we’re in crisis. It’s not just about us. I think the world is changing dramatically, and we’re trying to figure out what our place is in that world. How do we respond to it? And how do we provide for the people? How do we make this a place where people can prosper and do really well and feel really proud of [the country]? And also a place where people feel like the system works for them, whether it’s the government systems, or the system of capitalism and market economy, or the systems of social support, healthcare, education. We’re in a spot where all of that feels like it’s up for grabs, in flux.

TH: For listeners that are not aware, you have a long history in this country as a founder, an early investor in more than 50 tech companies, and as an educator and mentor, as well as an executive, including a VP at Salesforce and at Shopify. You have been called “the Forrest Gump of Canadian tech.” Give us a sense of what you were seeing in the tech sector that moved you to tackle this project, Build Canada.

DD: Sure. Build Canada wasn’t just about what I saw in the tech sector. I’ve had lots of chances to move abroad or move to California to work on businesses, and I’ve spent time there. But I’ve stayed here because I’m grounded in my friends from when I was in kindergarten, friends from high school, university, and all that. And so what was happening around the time that I was leaving Shopify — I left after six great years — was there was just a lot of complaints. A lot of complaints about what we talked about, where we are as a country. Yes, with other tech founders. But also with my friends who are doctors or accountants or teachers or musicians. I have lots of musician friends. Everyone was feeling it.

I like to think that Canadians are action-oriented people. We should be. We have a great history of taking agency for fixing things ourselves. So I was like, “Okay, I think we can do something better.” That was the impetus. It was: How can we contribute? Everything that has happened with Build Canada — the fact that it’s become a platform and a way for people to share policy ideas, but also all these digital tools that volunteers have been building, and also people meeting up and getting to know each other because they share a passion for a country that is unafraid, unashamed, and wants to build, wants to prosper — all that happened organically. That wasn’t the plan. The plan was: Maybe we can publish some policy papers that will be helpful.

TH: These policy papers, they’re very wonky, but they’re also incredibly specific, on everything from housing and transportation to immigration and digital innovation, with really interesting policy recommendations. But you are also out on the ground. You do have this volunteer base that seems to be growing. I want to talk about what you see as the main impediments to innovation in Canada. But let’s approach this on a really small scale, on a really practical basis. I know you’re up in the Kawarthas, and I understand you’re mentoring a young guy who is starting a landscaping business. He’s considering leaving Canada. Walk us through where that frustration is coming from, where the roadblocks are coming from, and where you see the points of intervention in something like that.

DD: I’m happy to say that that young man I was mentoring has actually got a job at a really promising startup in the Canadian defence industry, which is an awesome turnaround. If you got the reference, I guess it’s from another podcast where I was talking about that this feeling isn’t just in the tech community but with people all over. Look, I don’t think I have anything particularly novel that people don’t experience themselves. They see that affordability is challenging for people. Getting a job — a first job — is hard for people. Buying a first home is difficult for people. If you’re running or growing and scaling a business, finding capital is hard for people. Finding customers is extraordinarily difficult for people as they grow their businesses. There’s traffic in cities. There’s just this accumulation of frictions, frankly, in people’s lives. And I don’t say friction in a trivial way. These are real things that stop them from getting where they want to be and living the life they want, which is where I think we should want everybody — to feel like they’re living a good life.

In the case of what we’re specifically talking about, there is lots of excessive regulation. There’s lots of excessive process and policy. There is risk aversion in purchasing, and these are both behavioural and policy choices that I think we’ve created for ourselves.

With Build Canada, you mentioned something that I’m glad you picked up on, that these are very specific [recommendations], at least in the case of the policy memos. We wanted to not be hand-wavy. We wanted to say, “Hey, if you’re an entrepreneur and you have some specific expertise in growing GDP…” What is growing GDP? It’s either government spending or its businesses selling products and services. That’s how we measure it. They have to grow. So when we talk about GDP, we’re really talking about Canadian businesses having to grow. To your question, the answer of what the impediment is is different in every industry and every segment, and there are lots of them. Part of the project of Build Canada — at least as far as we publish these [memos] — is to get people who are in those industries, whether it’s real estate, oil and gas, or technology in next-generation finance companies or digital health, to be able to articulate, “This is the specific law, policy, or rule that, if you changed it, would help us grow.”

And similarly, with people who are in the business of financing startup companies: “If you changed this, this would help make capital more available.” I’m not giving you a pithy answer, I apologize. But that’s why we wanted to be specific, and why we have a broad spectrum of them. The idea was not “you have to do this specific thing,” but that we have to broaden the aperture of what the possible solutions are. Because if we’re actually taking ourselves seriously, if we’re in a period of crisis … When we were last in a major national crisis, which to me was COVID … We could have another conversation on another podcast about what we did right and what we did wrong. But one thing that I think we did pretty well, for the most part, is we stopped trying to have the old rule book. We were like, “Okay, we’ve got to go do some stuff. Things have to get changed quickly. Let’s go try this thing now.”

All of the excuses about why we couldn’t make changes — even simple things, like you can’t buy beer online or have it delivered. People in that industry had been asking for that for a long time. Then it was like, “Oh, COVID has happened, everyone is stuck at home, we’ve got to get them some beer. Okay, cool, let’s do that.” Amazingly, it became possible.

I think as a country, if you truly believe that we’re in a crisis — which I think we’ve heard from all sides, and I believe it too — it’s an economic COVID. It’s a massive change in the way we’re going to live, caused by the way the economy is changing, both geopolitically but also technologically. Okay, we have to quickly move to try new things, experiment, and see what happens. We cannot analyze and overcomplicate things forever.

That’s back to the kid who is trying to build his business. I think he was able to get going. Let’s continue the story. He’s now at this defence startup. It’s a promising, great organization. They’re trying to do great stuff, but it’s going to be hard to raise capital. Is the government actually going to follow through with spending on defence? Is this going to happen quickly? Is it going to happen enough that we can get the economy growing for new defence companies in the country, or are we going to talk about it forever? Are we not going to try? So, I think unblocking that urgency to change and try things is a very powerful underlying factor of a lot of the issues that I’ve listed off for you.

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TH: COVID is an interesting example. I don’t want to re-litigate the pandemic on this podcast, but it does point to something that I did want to raise with you. This idea of reducing friction and acting fast. In the COVID world, we did lockdowns, we closed schools. Now there’s a lot of research that maybe those things weren’t the best ideas. And so this idea of acting fast in business may come with downsides as well. Just to play the devil’s advocate, tech moved very fast. We have things like social media now. You have researchers like Jonathan Haidt, author of The Anxious Generation, pointing to harms to the next generation of kids. Do you think there’s any merit to that argument that maybe regulators sometimes haven’t been aggressive enough? I can hear people interjecting with that.

DD: Well, first of all, I’ve met Jonathan, talked to him, read his books, and I understand his argument. And I have kids myself, and I also have concerns about what’s happening. I think — at least in my view — in his particular issue, it’s super hard on parents, but it’s also parents’ jobs, in this case. We can’t always just say this new tool existed in the world and it made our kids different. Because the bigger, deeper truth is we live in a technological society. I’m not just talking about Canada; it’s the whole world.

You mentioned I was an educator. I taught this class for almost a decade at U of T Law School on how we respond to exponential technology. Because all these things were predictably coming — AI, genomics, drone warfare — just go down through the list of things that are now the headlines. Not just me, but many people were saying, “Hey, we’re about to enter this world.” The thing I was interested in was: How do we react? What do we do? I think there’s one world where we say, “We’re going to slow this from happening, we’re going to ban things, regulate things, make it difficult.” And there are problems with that. First, I just don’t think it works. Jurisdictionally, maybe in some cases. Certainly there are reasons for things like age limits, and I’m not saying we shouldn’t have regulation. I’m not in any way suggesting that. I absolutely and wholeheartedly believe in the role of the state to regulate markets and regulate behaviour — all sorts of things — for sure. But if the belief system is that we can stop things like AI or stop the progress of mass general adoption of technology, I think we’re going to have a very hard time doing that. Because we don’t exist alone. You were asking what’s happening with Canada. One of the things happening is that Canada is more connected to the rest of the world, in many ways, than we ever have been before. That is part of why we’re feeling all sorts of changes happening in our country in whole different ways.

So I do think regulation is a natural urge. But I think we have to be very careful with it, because I think the belief that we will slow or stop massive technological change from continuing to accelerate, unfortunately, is false. I just don’t think it’s going to happen. It doesn’t matter whether I want it to happen, I just don’t think it can happen. So I want to be pragmatic. And so, if you’re in that situation — and again, to repeat myself, I’m not saying don’t do regulation, don’t think about it — but long-game, I don’t think we’re slowing the rapid acceleration of all sorts of technological change in our society. We don’t have time to go into all the reasons, but I think that’s what’s happening, and I think we can just look and see that’s the real lesson of what’s going on.

So then the question is: What do we do? I think as a country, you have to learn how to lean into it. Lean out is the topic of your thing but I don’t know if I agree in this case. I think what you have to do is greet the future as it comes to you and build a very resilient, adaptable population that is able to take new things and reform itself quickly. Because the only constant is going to be that there’s more things changing all the time.

That sounds super highfalutin, but I actually think translating that into what we were talking about before is that you’ve got to have governments be able to try new things. They’ve got to try stuff that might not work. To your question, that might result in somebody being upset, someone being harmed in some way. It is possible. But also recognize there’s virtually nothing that we enjoy massively in the world that doesn’t have downsides. Jonathan Haidt is right, social media has downsides. So does TV. So do books, right? Books are amazing, but I can tell you lots of bad ideas have been spread by books. Has anyone ever heard of Mein Kampf? Books aren’t universally awesome, right? Cars have massively changed our world and horrible things happen with cars. Thirty thousand people die in the States every year from car accidents; I think it’s three or four thousand in Canada. And on and on and on.

Like I said, you can’t just say don’t do anything. But you have to have a balance that is on the right side. And what I think is, in a world where things are continually changing even faster, for Canada to survive and thrive, we have to be ready to understand that things are going to keep changing like that. That’s what I really meant about the urge that happened in COVID and how we react now. I don’t know what it’s going to be, but there will be more things like this happen. More change of like, “Oh my gosh, I didn’t realize that was possible.” That will happen more frequently than ever before. I really believe that. I think it’s really difficult for any one country or individual to stop that — it’s not trying to be negative or technologically deterministic. It’s just, I think, an observable fact over the past couple hundred years, of where humanity entered this kind of technological acceleration.

TH: I have just raised a line of argument that I hear on the left. I want to raise an argument that I hear on the right in this country, now — that there is a cultural element at play here. That we are not particularly kind to our homegrown successes in this country, at least not until they find success in the States. And that we have a suspicion of entrepreneurs and business people, people who become wealthy. How do you address that cultural issue?

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