Introduction

So, Ashna, welcome. Thank you so much for having me.

This is definitely not the first MindStone event that I've attended, and it's always amazing to see the variety and breadth of community that comes together for this.

So impressed by the turnout in the middle of summer, and it just speaks to the incredible programming and consistency that you put into it. So, thanks so much for all your effort in this, and it's very humbling to be here.

Awesome. I actually just show up, and it works like that.

There's a person who gets the pizza who will be here in a bit. You know, the AV team is always fantastic. A round of applause for the AV person there. Always on time. Do a great job of coming on time.

And then there's a person who takes care of the sound, so he's not around. He's the guy who makes me nervous. Every time I can't find him, and I'm telling, like, Nick, where is this guy? So, yeah, everything works like clockwork.

and we are happy that you're coming here second time the first time you were here you were part of the audience and you liked something that you're here maybe

you can start why this whole community is needed to learn AI maybe it's a

Why local AI communities matter

starting thing yeah I think it's always special to bring folks together of a variety of levels folks who have spent time in the space as early adopters people who are more technical and less technical I think having these honest and open conversations is such a wonderful way to bring folks up to speed when there's so much

available and so much noise like online and the internet i think having real conversations with real practice practitioners is really the best way to continue to drive innovation in an ecosystem like toronto yeah to the ecosystem of toronto round of applause for everyone who's showed up here

Toronto’s momentum and ecosystem energy

One of the most vibrant, one of the most vibrant ecosystem and I was going through the report of CVCA in the morning when you were there on the live stream that Toronto has the most number of investments made in this quarter, even the last quarter and consistently been, you know, outperforming other cities in Canada.

So you know, Toronto has a great scene while talking about also specific question on how how you see AI and you've seen this whole phase of AI when it just burst, like in a body came and like really early days,

I'm talking January, 2024 or 25, right? And now from now you've seen the whole thing kind of go from there to that. What has surprised you the most like in this whole journey?

Ashna’s background and a longer view on AI

Yeah, so maybe I'll take a step back and give a bit about kind of my background. So most of my career has been here in Toronto.

I've been a venture capitalist here for nearly eight years did a little stint as well in Philadelphia as well as investing in San Francisco but I've been largely cross sector cross stage and it sounds like a lot of you guys are

technical so you know that when people talk about AI today they're largely talking about generative AI but a lot of us know that AI had a very different definition many years ago.

So, you know, my first AI investments were back in 2018 when we were thinking about things from the lens of neural networks, we were thinking about applications within computer vision, and I would certainly

What surprised investors: consumer adoption accelerated

say that one of the things has surprised me the most about how, you know, the adoption of AI has really accelerated is largely across the consumer base.

So I would say today when we think about how Claude and ChatGPT and some of these very consumer AI applications perform, they're fairly good now. Like they get the job done for a lot of day -to -day basic tasks.

But even as early as you mentioned early 2024, I wouldn't necessarily say that it was really there. So I think that the consumer appetite to tolerate a lot of that iteration and support the training of these models over time to get it to a place where we can leverage these tools at work has been very, very meaningful.

AI for content: normalization, regulation, and watermarking

Yeah, and I'm personally surprised by the fact that when all the people started to use AI for content, is anybody now using AI for content, like writing content on LinkedIn? in, how many people are using that, right? AI for content? Some of you?

Maybe just you, I'm surprised. So yeah, a few more hands.

And there was a time when it was like frowned upon, you know, these guys are using, now everybody has to use it, right? Like you cannot, like,

I'm not saying you have to, but then you have to be more productive by using AI instead of ignoring it.

I think it's really interesting, like on the content side, I don't know if you saw it, but in response to EU regulations yesterday, Anthropics said that they're going to start to, in future models, implement invisible watermarking over their text that's been copied and pasted.

I think that's gonna have real implications for, say, like Sophia content, but it's also gonna have hopefully positive implications for any educators in the room who are teaching students and probably have been seeing a lot of AI out there.

So certainly, you know, leveraging these tools is something that is beyond mass market today and that adoption has been a lot faster than a lot of us and when when did you feel that from this

emerging technology it it became that moment when investors felt like oh this is gonna fundamentally change yeah you know everything now right when was that moment for you like which was the exact moment you felt you know there was a

The inflection point: when AI felt truly transformative

a good amount of time where I was skeptical about the pace of adoption, largely because of the vast swaths of data that are necessary to train their models. And I know that there was a lot of synthetic data that was also being leveraged to train these models.

So if you have mistakes in your core and then it's rippling out into your synthetic and then training your models, I thought, well, are you going to have flop training slop? Will there be issues?

but I think that I was certainly proven wrong probably last fall or so I would say when Claude co -work came live in Codex I think that's the real time when you

could see everyday folks integrating like these frontier lab models into their day -to -day workflows where it had the context around every single application you're on and everything and the use cases being able to have this in your day -to -day and in your regular working tasks

actually became feasible, and the models became good enough to actually help you in a number of ways.

I think co -work and cloud really tip the scales at the enterprise level and working level, and a lot of that has now trickled down into how people use it outside of work in their day -to -day life.

Founders and funding: building real value vs. riding the wave

Yeah, and talking about you looking at founders also building in AI, there must be some founders there in the room or wannabe founders or soon -to -be founders.

How many founders in the room? Any founders in the room today? Okay, we have four or five. Great.

Any to -be founders, aspiring founders? Few people. Amazing.

So for them, in the future, to raise money, firstly, how much of that is needed now has changed as well. but but in terms of who is really you know building something meaningful in AI versus somebody just riding the wave how do you how do you differentiate yeah

I mean it's a great question I think that the period of riding the wave is largely over I think that now enterprises that previously I kind of blank check budgets to say let's adopt this let's test and trial as many many different AI tools and we're seeing some solidification now where

organizations have a general idea of what their toolkit is today, how to make the most of it, what additional things they would want to add. I'd also say that

when we're thinking about like vertical AI in particular, a lot of that is now being at risk or vulnerable for disintermediation through the virtual labs.

So I think that that time where you can ride an AI wave and get funding because your AI is certainly long gone for us a lot of funds are specifically dedicated to only investing in AI vaccines today but really need to

make sure that what you're building is resonating with your end -user regardless of what under them so is this addressing a specific quantifiable point that the user understands really well do you have some sort of specific unique positioning to address that so frequently that looks like some sort of data mode or a deep embedded within

an end user's like day -to -day work yeah so i mean in general then what do you look for to have like a second meeting so so the first meeting cannot uh happen if something is very superficial superficial high level uh just riding the ai wave or or not with real mode in it as you said i would say like

personally it's probably been like three like the last time i genuinely saw an ai rapper hit my desk was probably 2020 you're getting good deals then on your table and also you were looking at uh you're talking like late stage or early stage early early stage okay that's that's surprising i have sometimes

you keep seeing them but but how do you get the second meeting with you if somebody's really really building interesting stuff, a lot more, you know, technical, I can say, but with a real purpose, or maybe having a good distribution, for example, with a technical product is a

better bet, right, to get in, so what makes it the second meeting, then, like, why would you meet that founder again for the second meeting?

Upside Feast: a creator-led fund built around distribution

Yeah, so maybe I'll start by kind of sharing a bit about my fund and our thesis of what we look for in founders.

Very exciting, buddy, I was going to ask you that, that was my next question, yep. For sure.

So I'm a partner at a fund called Upside Feast. We were started two years ago. We were co -founded alongside some of the biggest creator talent.

So what makes us different is that a number of our LPs are some of the world's largest YouTubers, streamers, influencers, DJs, and the folks who are our LPs who we're talking to on a very regular basis, nearly daily, have across them a combined 500 million followers and subscribers so really what

we bring to the table for founders is distribution we're able to support our founders with the right messaging content creation and collaboration to help them get to the right audience at the right time and message it in the right way that actually drives real subscriptions real adoption so that's

generally speaking the type of value proposition we bring to the table when when we're partnering with businesses.

In terms of, you know, So mostly consumer, because they would need the distribution, right, to grow.

So in terms of the thematic areas where we're really excited, a lot of that tends to be places where the founders can really benefit from 500 million eyeballs. And so naturally speaking, consumer technology is a big part of that.

You know, we also see a lot of C2C, of course, B2B2C as well. and we also look at a good amount of infrastructure plays within sports media

entertainment gaming imagine our creators also have a lot of different businesses so we're always excited to look at different things at the intersection of commerce retail supply chain but really the distribution

network is how we're able to offer something that's very differentiated to founders so tying back to your original question about what are we looking for

What earns a second meeting: fit, differentiation, and founder readiness

or what gets through that second meeting. The first thing is, of course, alignment that what we bring to the table and how we work with founders is something that really resonates with that founder.

That they have an idea of how we can genuinely them is important. But otherwise, what we're looking for is pretty clear cut.

We're looking for a founder who really understands the pain point that they're trying to solve and really understands how what they're building can address that pain point in a unique way so they're uniquely addressed

position it whether it be relationships network data or product angle but there's some sort of reason why they are the ones this we're also looking for

founders are you know willing and ready to build so oftentimes that looks like deeply relevant domain expertise base that they're building in or it looks looks like past entrepreneurs, from my perspective, doesn't matter to me if that entrepreneurial experience was

successful or not. It's really about having those learning.

And then we're really trying to understand the market that you're building and what's the potential to grow it. We're always very excited by category creators, as well as folks who are trying to expand

what a category could be. And I think now is a very exciting time to do that.

Anybody here trying to build in B2C? B2C? What are you building, sir? That's super exciting.

We should certainly exchange information. I'd love to learn more. That's the shortest pitch ever. See?

When you get the right people in the room, you know, things happen. But building in fintech is what you said, right?

So somebody like him building in fintech because obviously they have to eventually get it out of the people so that more people can use it they just don't get your money but potentially they just don't get your money but also they get those 500 million eyeballs that's the proposition on your side right yeah

we're very grateful that our lp even the companies that we back and and the fact that they take time time to promote our founders as they do every year. Very grateful for their efforts.

And I mean, I am still a very young YouTuber. So am I eligible to be an LP in your fund? I will take your money anyway. Who will say no to money, right?

But that's very interesting. I mean, I think a lot of creators now are feeling empowered by something like this, that they can participate in the VC industry. Thanks a lot.

That was, you know, all the questions I had. But I have one final important question, which is, you know, are we living in a simulation? You know, my answer to that is it doesn't matter either way. It doesn't matter either way.

Amazing. That's a great answer. So that's on my side.

Audience Q&A

Anybody who has a question for Ashna? anybody in the room yeah i'll just come down and give you the mic so that you can ask the questions

Fundraising benchmarks, ARR, and valuations in a faster build era

you're okay okay yeah a thousand percent um you know it's really interesting there used to be a very natural and obvious progression that you would see from c series a and usual like arr benchmarks that you hit but i think all of that is really substantially compressed because it's never been easier to build a product and ship one and it's also never been easier

to set up your go -to -market infrastructure so we're frequently seeing businesses that raise a small angel round ship something really quickly and they're already coming when they're like quickly approaching 10 million in ARR and they're calling that a seed when I think if you asked me like five years ago that would have easily been a beat so when we're thinking about how we're

valuing these businesses they'll have to take it from the lens of what are public comparables right now what are acquisitions right now I think now that we're in 2026 there is a good amount of precedent and relevant activity in the public markets that can help us with a lot of that I would say that it would have been a lot more different in like 2023 and 2024 but a lot of our our typical frameworks for valuation are functioning again in a meaningful way.

I would say that when you're pre -launch, pre -product, it really comes down to making sure we're protecting the founders' ownership and making sure that they're not diluting themselves too much and making sure everyone's got a good amount of skin in the game.

Anybody else has a question? You need a mic, sir? OK.

Creators, distribution, and the idea of a “YouTuber unicorn”

that's a really great question I don't have an awesome answer I've certainly seen like five or six people unicorns now over the past couple years I'm sure that one person coming around or maybe it already um I strongly believe that when you're building when you're in the trenches it's always helpful to have someone else there to handle all the stress that comes

I'm just being a founder, so I do not envy fellow founders. But I see very little reason for that not to happen. I think become a YouTuber and become this, you know, unicorn founder, and then sell the YouTube channel for a billion dollars.

That can happen now. I mean, I think because the creators are now becoming a big part of the distribution. I mean, that's the unicorn I'm chasing. I'm just kidding.

It's just the thought came to my mind like it even that can be a potential sort of acquisition for Some people right like a brand of a youtuber Yeah Yeah, that can happen, you know any other question

Early-stage red flags: co-founder dynamics and market realism

Such an interesting question. I don't think that I would have Red flags, I think it's really hard to have like red flags just from getting to know someone I

think something that I certainly look at is if I'm speaking to two co -founders it's important to me to see how they're interacting with each other so if you see them on that first call with you if they're disagreeing with each other or talking over each other and there's like a lack of cohesion I think that's something that I would probably qualify as a red flag because you've got a co -founder you're navigating so many ups and downs every single day when you're

getting a business off the ground in terms of like not knowing your product or not knowing your industry I always really try to like defer to the founder right they're the ones who like quit their job or like dropped everything because they felt so passionately about wanting to solve a problem and I'm feel very humbled that I get to like learn about their mission and their vision of

what makes them passionate directly so I think that when I disagree with like a view of an industry with a founder I fundamentally always assume that I'm wrong that's always step one I think not a red flag but maybe a yellow one and

this is like one of the oldest things but sometimes you'll see founders say stuff like we have no competitors and I think generally speaking yeah maybe you You don't have a direct competitor that's solving something in the exact way you are, but there's always some sort of status quo or there's always some sort of substitute. So really speaking to what the market dynamics are at any given time is really important rather than saying there's no competition, there's only us.

I think that just shows how nice and polite you are in general, because a lot of VCs are very vocal about some of the red flags, but you're right. everybody's going through their own journey it itself it's like a big deal right somebody trying to build something is already you know earns respect in your eyes it seems right but it's just the path that's not matching at times maybe it's not the right timing or maybe that there are so many other things that the founder still has to figure out which are not red flags it's the it's

the journey right it's the path thousand percent and I would say that you know when you're investing at like the super early stage the business that you're you're investing in it is night and day from the business you're going to see at a series A and B because there's so many pivots and evolutions along the way. So making sure that you give the time and space to founders to be able to evolve and make those choices when they see the time is right to do that.

Awesome.

Closing remarks and staying in touch

That's it from Ashna's time because we have the other two speakers also. But, Ashna, how long are you sticking around for? I'm probably going to head out in the next little bit, because I have another engagement to attend.

But I think my name was up on that screen, so if anyone wants to get in touch with me to talk about tech, AI, consumer, in general, please don't hesitate to add me on LinkedIn. Just note that we met at MindStone, and I'd love to continue the conversation.

really appreciate you guys taking the time to hear us out today. Yeah and

before you go Ashna, I want to point out that she's not one of the you know busy VCs or she will say that I cannot stay around but she's genuinely busy now because after 11 days you're moving out of the country right and you haven't still started packing.

You said that at the bottom. I have not started packing so I'm quite behind on that but it'll be it'll be an adventure. The move will be good.

Yeah, best wishes to you, Ashna. Thank you so much for being here. Thank you. Round of applause.