Jesse Wiebe - Canadian Startup Capital Association

Welcome to another Founder Wisdom Pod. We have Jesse Wiebe with us today. He's building the infrastructure for Canada's early-stage capital ecosystem up in Saskatoon, Saskatchewan, fellow Canadian. Has the stories, founded a bunch of companies himself, WeGrow Capital, Floatlove, a whole bunch of companies, right, Jesse? So glad to have you on. Tell us a bit more about yourself and what you've been up to.

Yeah, it's great to be here, Charles. Thanks for having me on. This is exciting. Always great to have a conversation about what we're working on here in Canada and in Saskatchewan. I was born and raised here as the son of a serial entrepreneur. My father built and sold a number of companies, but two in particular. One was a fertilizer business using a uranium mine waste stream, and the other was a software company started on a floppy disk in 1981 and ended up being sold to the federal government still operating today as FCC or Farm Credit Canada's AgExpert platform. So those two exits did pretty well. I spent my 20s traveling, studying, eventually got an economics degree, but the work I was doing in Toronto, it came to a halt when COVID hit, moved back home in spring of 2021 and had a number of conversations, or spring of 2020, I should say. And then later in the spring of '21, had a conversation with my father about what came next for the family. And That's when we formed Regrow Capital and Consulting as a family office. Shortly thereafter, I found Startup TNT, a group out of Edmonton, building a new way of doing angel investing. And I joined that organization, brought them to Saskatchewan, founded the TNT Saskatchewan chapter, helped take them to Manitoba and BC, and then fully national through the Agri-Food Program. Having grown up on a farm and as I said, the son of a serial entrepreneur in the agri-food sector, very passionate about the ag sector. But I'm very passionate about startups in general and I've had the privilege of working with hundreds of founders. I've invested in about 50 companies now. I'm also an LP in 4 VC funds and most recently started the Canadian Startup Capital Association representing first check to Series A investors and getting more capital into the Canadian market. So yeah, pleased to be here and excited to dive in.

And you were born 30,000 feet into the air. How was it like to grow up under like a successful and serial entrepreneur as a father?

Yeah, so not only was he, you know, an entrepreneur, but he also worked in economic development himself. My family moved to Bangladesh when I was 2 years old. You just pointed to one of my most recent articles I posted on LinkedIn about being sort of born on a plane. And I'm traveling a lot now. And people always ask me, you know, do you enjoy it? And I was like, well, it feels like I'm going home every time I lift off into the air. When we were there, you know, we obviously traveled a fair bit around, you know, India, Thailand, while we lived in Dhaka, Bangladesh. But then on the way back, we continued around the world. So by the time I was 5, I'd done a full loop all the way around the world. So, I've always sort of considered myself to be a bit of a global citizen. It's really affected my values and made me always very open to working with people, but also had a very big compulsion to want to solve problems in the world, which I think is at the core of any good founder. They're looking to solve a problem. And so, that's what I learned from my travels and learned from my father.

Right, and do you, I had an entrepreneurial dad myself, middle, almost upper class, one would say.

Yeah.

A lot of the top, the world's top founders were also middle, upper class. Take Zuckerberg or Gates and so forth. I had some chip on my shoulder, right? But I also have like the safety net to fail, one could say that I feel is very important. How do you think about it on your side from, growing up in privilege, but also do you feel you still have that chip on your shoulder which could give you a shot at making it big?

Absolutely. You know, I have had this conversation a lot, not just with my own father, but with friends in the ecosystem that come from similar sort of backgrounds. You know, my father often said he wanted, you know, his sons, just, it's just me and my brother, to have the respect for money like a blue-collar worker, but be able to, to live a life like a white-collar worker. And so for many years, I did have that chip on my shoulder. You know, I have to prove it myself. I have to build everything myself. You know, I couldn't take, you know, the handout from mom and dad. But I sort of started, came to the realization that, you know, you can't choose the hand that you're dealt, but you can choose how you want to play it. And, you know, if I chose to, you know, buy the Lamborghini and go pop bottles at the club all the time, sure, hate me for that. But, you know, what I'm choosing to do with my money now as a family to invest in our local economy here in Saskatoon and in the province of Saskatchewan, but then also investing in Canada as a country. You know, I don't think anyone can really fault you for that and for wanting to build something big with the legacy that was provided to me. You know, one of the things that really sort of hit home for me once was a friend of mine. That's one of the heirs to the McCain fortune. For those who don't know, McCain fries here in Canada, really big potato.

So good.

Yeah, very good. A lot of people love them. They have other products as well, but they're—

Best poutine fries, in my opinion.

Yes, there you go. Yeah, yeah. So obviously a lot of people know them very well. And one of the things he said, you know, 'cause he'd also had similar people come at him over the years for being privileged and having a silver spoon up his ass and that kind of thing. But he's like, well, you know, my ancestors worked hard. Like, it wasn't like this— that the money that they got was handed to them. They had to work for it. And to not do something with that money is a dishonor to your ancestors. Like, I don't think there's anybody who's a parent that wants to say, hey, I want my kids to be worse off than I was.

Yeah.

Everybody always wants to make it better for the next generation. And so for us to attack the people that are taking that money and try trying to do something good with it, I don't think is right. But yeah, it's definitely motivated me to live up to that legacy. You know, we called the name WeGrow Capital. It's got a W-I-E in there because our last name is Wiebe. And we actually called the holdco WeBequest Holding Corp. You know, about how do we bequest to the next generation? How do we leave a legacy as the Wiebe family that the next generation of Wiebes coming after me will be able to take forward and run with? So yeah, it's great to hear your story and something similar. I think you're absolutely right. There are a lot of people that come from these backgrounds that end up building big things and how they choose to kind of live that legacy is most important.

Tell me about the Canadian startup ecosystem, especially, do you call it like the Midwest? How do you call Saskatoon?

Prairie, we call it the Prairie. Prairie.

Yeah. How does it do?

I mean, it's a gritty, resilient ecosystem. It's capital-starved. There unfortunately aren't a lot of angel investors out here. I've been working hard to change that over the last 5 years alongside Zach Storms and Tim Lin at Startup TNT and all my colleagues there. But there's some incredible founders, many of which are a little older, you know, your 30s, 40s, 50-year-old founders as opposed to some of those, you know, 20-year-old founders you often find down in the Valley. They are often coming from industry where they've spent, you know, 10, 20, 30 years working within industry. And all of a sudden they're going, "Hey, there's, you know, I hear about technology, especially now with AI, that there's an opportunity to do it better, right? There's gotta be a better way." And so then they're starting companies. There's some great incubator programs. Shout out Co-Labs here in Saskatoon and Cultivator down in Regina doing some incredible work to support founders here in the province of Saskatchewan. Mm-hmm. They often are getting to cash flow positive a lot quicker because again, they don't have that same level of capital availability. So they have to be more resilient that way. But invention, entrepreneurship goes all the way back. You know, the farmers that started, you know, settling out here, they had to come up with ways to solve their own problems. And so they were inventive and they came up with new innovations. And, you know, there was a, I joke often, there was a show here in the province called Prairie Farm Report, where they would literally do that. They would go around to different farmers and say, hey, what have you come up with? And it was like a new auger or a new system of managing livestock. And some of the world's biggest innovations in agri-food, especially broad-acre agri-food, have come from the province of Saskatchewan. The big seeders, those were all invented here in Saskatchewan, and we don't talk about it nearly enough.

Tell me about some of your life experiences before we get into the nitty-gritty here, like working for Gordon Ramsay. How was that? Did you get verbally abused?

No, I never got to meet him directly. I've since run into him at some events, but I—

You just got a text from him saying, "Get your shit together, Jesse." Yeah, yeah.

Well, I definitely got that from the sous chef. I definitely did get verbally abused. I did it for a month. I—

What a beautiful culture.

Yeah, yeah. I mean, it gave me a bit of a wake-up call on whether or not I actually wanted to do it for a living. You don't get paid very much. You, you have to work lots of hours.

Like cortisol as a culture.

Yeah, basically cortisol is the culture. Absolutely. But, you know, working in kitchens, you know, I worked 2 years at an Earl's here in Saskatoon as well after dropping out of engineering at Waterloo. I straight out of high school, I went to Waterloo for a few years. Realized I didn't want to be a chemical engineer after doing some co-op terms and then thought I wanted to be a chef. And then after working in one of Ramsay's restaurants there in London, England, I was traveling there and had a 2-year visa to live there. And it was an incredible life experience. Really found myself. I read an article once talking about Carney and his travels abroad. And I think it really crystallizes your identity as a Canadian when you live somewhere else. Because you have to talk so much about what it means to be Canadian and who you are as an individual within that identity. And so, that really helped me when I was living over in London. But after, you know, deciding I didn't want to be a chef and didn't want to know what I wanted to do, eventually, I found the book Thinking Fast and Slow. Incredible book. Highly recommend that book. The only psychologist to ever win the Nobel Prize in Economics is Daniel Kahneman, who wrote that book with his his partner who passed away. And they— that book led me to really getting enlightened about economics. As mentioned, my dad has experience in ag economics, that was his background. So it kind of came full circle there for me. And I ended up going back to York University, with a focus on economic development and public policy, worked with some NGOs before COVID hit. And then everything kind of went downhill when I lost my job, my apartment building set on fire, and then my girlfriend at the time broke up with me after after we've been together for 5 years. So moved back home and then had those conversations with my father about what was next for the family legacy, next for me, and starting the family office, which then led to the startup TNT Connection and working in VC. And this has been my favorite. I often say this, and a lot of people have said this, finding the startup ecosystem was finding my people. I was like, these are the people I've been looking for. And I'm sure that's very similar for you, Charles.

Oh yeah, for sure. Founders and oddly enough VCs. I thought like VCs were pretentious privileged people, but even if they are a bit of that, they still like fuel the full founder ecosystem. And ultimately I do think that the founders on our planet Earth, they fuel the world, right? Like they're the basis of the world, why we have all these amazing services and an economy that's going and why we're not fighting in wars. I believe that's mostly because of trade. Sure, some tourism as well. You and I, we traveled extensively, but like, I believe trading is like the secret to human wellbeing and flourishing, right? Like the economy. So, if the VCs finance that, like, the VCs are definitely gonna get some of my love, plus they're also very smart. Investing is not easy. I mean, and people that, that's investing easy, I think they're going out of business right now. I'm not sure like what you're seeing in the VC ecosystem right now, but there's too many of them, uh, is my feeling. Raising capital from LPs is getting harder, uh, plus like a bunch of them had the carpet pulled under them with like the AI stuff, devaluation and all that. What are you seeing in the current VC ecosystem of things?

Yeah, I don't know the, the US market nearly as well, so I'll speak more to the Canadian market. I think in the US market they probably are, um,, you know, overbloat with, with the number of VCs, a lot of people who are doing momentum investing and just sort of following in on, on, you know, the people who are actually doing the work. Whereas in, in Canada, I think we're under-resourced and, and we actually need more fund managers. I think to your point, you know, the, the previous generation of, of investors slammed into two black swan events with COVID and then AI, where a number of companies are starting to move down the other side of the value curve, to your point. And the TVPI of some of these funds is starting to decline. And so that's also leading to a pullback from the LP base. And also, you know, the liquidity, especially here in Canada, has been next to nil for 2 years in a row, 2024 and 2025. We had zero IPOs. from a Canadian tech company. That has obviously started to change with the recent SPAC with Xanadu and some other companies starting to see progress in that direction. But we're still limited in terms of actual DPI. Only the upper quartile of funds have started to hit that north of 1x DPI. The most recent BDC report that came out just last month illustrated that some of the top quartile funds of, you know, that 2014 to 2018 vintage, I should say, I should say, are seeing north of 3x TVPI. But, you know, that doesn't matter until you can actually get that through liquidity. So what it is leading to is some hesitancy from the current LP base. I think a lot of the Canadian LP base is government-funded through one way, shape, or form, whether that's federal, you know, Vicky funds or the VCAP program, where it's a fund of fund money flowing from the federal government, or one of the provincial fund of funds like Alberta Enterprise Corporation, Venture Ontario, or some of the folks out of Quebec. But we need more LPs. One of the key reasons why I started CSCA is that Canada has 170,000 families worth $7.5 million or more, and we have approximately 10% of our population meets the accredited investor thresholds. And so we have a real opportunity to activate billions of dollars of capital from what many people would call retail investors. Mm-hmm. I wouldn't necessarily characterize them that way. They are high net worth, they're high income earners, they're people working in the ecosystem and in the industry that really understand the community. And we need to get them activated off the ground 'cause international wealth standards dictate that you should be investing 5% into early stage venture. And I estimate, or at CSEA, we estimate only about 0.05% of Canadian wealth is currently invested into early stage venture. And so, we've got a long ways to go. Mm-hmm. To get that number up. And if we did, there'd be far more capital available in Canada for an ambitious founder starting a company today. So, we're at a really weak spot in Canadian venture at the moment. If you read, you know, the reports, we need to at least double the amount of capital at the pre-seed and seed stage that's available, especially for pre-revenue startups. Those deep technology startups that are coming out of our amazing universities here in Canada. I mean, we invented AI in Canada. Straight up. Yeah, right. And, and so why, why are we the ones behind the 8 ball?

Because we're low-risk takers, um, and it culturally, right? And sometimes I'm asking myself, yeah, it can't, it can't hurt that the government helps, but Canada leans too much on the social side of things. And I don't know if we forgot like our basics that economy like justifies global wellbeing, right? Or national wellbeing. That seems to be in the basics, right? And that if that part is no good, then nothing can happen. So my question for you is like, if it's gonna be slow and a cultural change is like super hard usually, right? Like, how are you motivated by this, right? Because I also want to bring my native Montreal and Canada as a whole back on the scene or has it ever been on the scene, like bring them to the scene period. And I've explored that question last week with Nektar Tekonomakis, a VC that's been on my pod, I could plug you into last Friday, and it was like, okay, Joshua Bengio is not like too capitalistically motivated, maybe he needs a hybrid or someone that makes sense to, inject something into him so that he can bring AI and Montreal AI scene, right, and bring everyone up to it. Like, I mean, we can stay on the doomer side of things and social side of things and oh my God, things will break, but we need like to inject like more capitalism into us and less socialism. And ironically, I think that's how you increase the socialist part is by doubling down on something that's proven like capitalism. And Geoffrey Hinton got stolen away from us by Google. So I'm not sure that we could have done something about this, right? There's Ilya Sutskever that started OpenAI, but how about like just giving them proper tax advantages or incorporation advantages, providing them the adequate capital and making it— the government should make it easy for VCs to raise more capital in Canada so that we can avoid the fucking brain drain that's like making us less good. Yeah. How would you fix it?

I mean, this is the goal of CSCA. And first and foremost, it was started by a number of grassroots organizations from across the country that are doing exactly that work. I spent 5 years working with Startup TNT, and that allowed me to build a great network as I was sort of the growth guy, you know, helping connect the organization across the country. And I met some other great organizations like Spring that's doing some awesome work to activate more capitalists that are also focused on impact. Which one could say, you know, anybody that really wants to, you know, grow the Canadian economy, that is impact considering how much, how far behind we are, you know, and what you just said there, Charles. But, you know, we got the Firehood, we got the Indigenous Venture Challenge, we've got, you know, groups like the Okanagan Angels, and then some of the, the great angel groups like G10 and Ange Québec out of Montreal area. They're all looking to do exactly that. The unfortunate reality in Canada when it comes to Canadian wealth is that the majority has come from non- tech or startup background. So most people that have wealth don't understand how to invest in early-stage ventures here in Canada. Additionally, most people can't afford to write $20,000, $30,000, $40,000, $25,000, $50,000 checks. So you need to create more syndication vehicles and opportunities. But then the real important thing is you need to build community around it. You need to make it fun, you need to make it so that they can make friends with one another. You need to make it collaborative. And that's what all those organizations I just mentioned are doing. And so, first First and foremost, if we can get those organizations more resources, you know, TNT has activated 550 investors over the last 6 years. Spring has activated well over 1,000. You know, we've got hundreds and hundreds of more investors have been activated by a number of those other organizations I mentioned. So they— if we can get those organizations more resources, we can platform them more, and we can amplify their messages and connect them together, strengthen them, that's going to help. But to your point, you know, let's get some better tax policies in Ottawa. We look at some of the programs internationally, in the US, you got the QSBS program. Over in the UK, they have programs like SEIS. And so one of the things that we're advocating for at CSCA is the first check capital gains exemption. So if you would invest within the first million dollars of equity, either directly or through a SAFE or even through an LP, you would receive no capital gains tax at exit. So investing early in a startup is rewarded. And that's, I think, really critical and important. And to your point, and we should also be rewarding entrepreneurs. Like they should not only be able to get better tax advantages for building the company. But if they fail, they should be able to write off the loss of their own business. I mean, they're, they're investing more in their business than almost anybody else's, and they're taking huge risks, and they should be getting, uh, opportunities for reward from that.

Yeah, Waterloo also was part of the conversation with Nectar. I think they're definitely doing something well, but maybe lacking on the incubator side of things. You need to grab a hold of these founders and never let them fucking go, you know. I think, uh, just to sum it up, you know, it— if we— if Canada could have the same competitiveness of USA vs Team Canada on the startup side of things, I think that would solve a lot of things. Unfortunately, we're fucking distracted with things like that, you know. In my native Montreal, everyone's like, oh, go Habs, go! Dude, that won't change no one's life, you know, like, it's a waste of time. Like, why not be that competitive, but when it comes to business, that would change a country. Unfortunately, I think we're— we have privileged delusion in Canada. We've gone too far on the socialistic side of things, and we're missing out. I'm not saying we should try to create another Silicon Valley, but we do have moats. What is— what are our moats? It's immigration. That orange man is dumb as fuck and is making all kinds of mistakes, you know.

We have a stable— we do have stable governance, and we have opportunity to build here. We have great resource sector. And I will say, you know, Prime Minister Carney has done a great job of sort of setting a better tone now for the country. You know, I spent last week in Ottawa meeting with senior leaders at ISED and at Finance. And people are receptive within the government to this message. They hear it. They want to make the change. They're listening to their own leader and it's trickling down. And there is a real opportunity. There's a real window. And one other thing I'll mention is that there's another generation, my generation, that is starting to take over the wealth of this country. We're entering into the largest intergenerational wealth transfer in human history. There's trillions of dollars of money that's moving from the boomers to their children. And if we can capture that moment and if we can get more people engaged from my generation in investing in the country, because they, you know, they're people like you and me that do see all of this and they want to. You know, our tagline at CSCI is Canada's future isn't something we inherit, it's something we build together. We have to take what is being given to us, kind of bringing full circle what we talked about at the beginning. We were dealt this hand, let's take it and let's play it.

Yeah, and to just finish my last point, right? And I'm pretty sure that's the full governmental mode is just taking what our friends down south, because they're friends ultimately, whatever this guy is trying to make us think, right? They're messing up on the immigration front. Take that. Open up the borders. Right now, Canada's not doing that. I think we're sort of being bitches to the current administration. And my wife is Mexican. Now she needs a visa to come in, right? How dumb is that? There are some counterpoints, but take the immigration mistakes, right? Open up the border to top talents, geniuses, right, that comes from all walks in all parts of the world, get them in Canada and don't ever let them go. You know, like give them a reason to stay and create our own ecosystem. I think we can take notes from Dubai, Singapore, right? Like that's the kind of ecosystem we need. And to your point, yes, we need to take boomer money and make something out of it. 'Cause boomers are, my opinion, are pretty much done intellectually. Most of them don't want to use AI and all of that. Sure.

They wanna go to the beach. They wanna enjoy their life that they've built.

Yeah.

Right, yeah.

Or take their money and do something incredible with it in the, along the lines of AI.

Yeah.

And at all costs avoid the brain drain. That's US moat, right? Whatever administration comes in power, leading the US is easy from an economical perspective. You have a brain drain, you're sucking all the talent from the world and you're keeping their tax dollars.

Right, yeah.

All the smartest people, you're sucking them in.

Yeah.

So, and the phase 2 of that to Canada is like, how can you create your own brain drain, which would be gigantic, right? That's very hard. It's more than just retaining like the towns, like creating a brain drain from the US, how amazing would that be? That would be like phase 10, right? Like then Canada would start being hyper-healthy and competitive. And people might be like, oh, Canada is healthy right now. Um, yeah, until AGI happens, until the agentic revolution hits, right? Then we're gonna see a much more different picture, right? Like, things are gonna go to shit. What's your predictions on that, by the way?

I don't know, you know, I, you know, it's interesting. I've been going back and forth between the two things. I mean, I grew up on sci-fi and, and all that. And Star Trek, and certainly quite interested in what the possibilities are for creating a potential utopian future of some kind with AI. I think a lot of it is propaganda from the Valley. Obviously, they have a particular incentive to want to push AI to drive up the value of their own businesses. I mean, just watch what just happened on Friday with SpaceX IPO, and—

Yeah.

Yeah, exactly.

And tell me, I, I didn't follow the news.

Oh, I mean, it popped. I mean, it popped immediately.

It went— Oh yeah.

Yeah, you know, and, and I mean, we're talking about the largest, uh, IPO in human history. Um, and I was talking with some friends at the CVCA conference about, um, SpaceX, OpenAI, and Anthropic. Those 3 companies alone as an IPO are going to be the, the greater than all the IPOs for the last 20 years globally combined.

Oh my God.

Which is a crazy number when you start to think about it.

But when you think about it, Elon is— I wouldn't never bet against Elon because everything happened.

Yeah, but that's part of it, you know, as you start to think is like the system is a little rigged to an extent.

They— Oh, but it's always been, and I mean, investor dudes, you know how biased they are. They will eat anything that is given to them if served properly, right?

Yeah, and so I do wonder about that and I do think the idea of SaaS is dead is overblown. Yes, I agree with that. There's a real opportunity, like there are applications that will always need to be deterministic, not everything needs to be generative, but whether or not we're gonna find the singularity and create, you know, an AGI or some sort of super intelligence. I mean, I hope we can find some sort of utopian future where there is, you know, something out there that can help all of us get into a better level.

Like, one of the— We're so close, dude. Like, all we need is memory and more compute.

And power.

Yeah, and agent to fuel the agent revolution.

Yeah, one of the greatest books I read, it's on my shelf behind me. It's a great book called The Social Organism.

Okay.

And it talks about the idea of holonic structures. And so a holon is something that's both an individual unit and a system at the same time, right? So you think of the cell in our bodies, right? The cell is both an individual unit, but there's also things within it. And then it comes together to form organs come together to form the human body. So what is the thing that lives above us? What is the system that lives above the human individual? And we've developed with the internet and now with AI, I think we're starting to really crystallize what that might be. And I just hope that it takes the best parts of us and not the worst parts of us because we can be pretty horrible to one another.

Yeah, but I think we're mostly good as a I agree, I agree. Like 8% evil and disgusting.

Yeah.

I think that most of us are good, right? Like when you remove all the barriers and all the appearances that we put in front of us, there's only love, right? And if you would remove capitalism, I'm not sure when capitalism's gonna scale out, but we're gonna get all kinds of different behaviors out of humans which are more love-oriented, right? Rather than just capitalistic.

To the question about capitalism. So there's two things going back to the Star Trek thing that we'd have to develop in order to get rid of capitalism. One is unlimited power, right? Because we need, we need a crazy amount of energy to do this. That's like fusion technology, the power of the sun, being able to capture that. And the second is being able to develop everything from its most basic building blocks, right? Protons, neutrons, electrons. Yeah, that's the replicators.

Elon's behind both.

Yeah, right. So, you know, I, you, you do hope that maybe, you know, we'll, we'll enter into a new world with some of these people. And, uh, but, you know, I always worry about some of, you know, the, you know, power, um, corrupts, right? And all of that.

Oh yeah.

How that could get, could get people to, to enter into a, to a—

But super intelligence won't give a fuck about Elon. That's the good news. It'll fly by its own and it won't give a fuck about pretty much any of us. And we can try to keep power with like Neuralinking yourself with it, but even then it would keep like full autonomy, right? It sort of flies by its own wing.

Well, this is, yeah, I agree with you. So, you know, we're definitely getting into territory that is more philosophical, but I do hope that we can build something that will better mankind at the end of the day. I mean, that's why I'm in this. That's why I do what I do. And I'm sure it looks like that's why you do what you do, to create a better future for your little one there.

Yeah, dude, it's on my mind every day. And even like AI schools for kids, right? Like I think the whole education system needs to be reshaped, but let's keep that for round 2. Jesse, where can people find out more about you?

You can reach out, our website is canadianstartupcapital.ca. We're gonna be launching our newsletter right away here. You can sign up for that. Sign up, become a member. I'm very active on LinkedIn, just Jesse Weave. Also the Canadian Startup Capital Association page, which you'll find this, this podcast on as well.

It was Jesse and Charles and my day.