You are a professional, professional, professional ambassador. That just means I've made a lot of mistakes and lost a lot of money and learned from those mistakes. I feel like I still need to pick up the pace at which they're moving. It's like you have four days in one day. You have a day from like 8 to like 10:30 and then you have another day to iterate on something before noon. Like think about it as a sports analogy, right? You're taking a 100 shots on goal versus 10. It just doesn't even matter if you're perfect. You're just going to win because you're going so quickly. There's a company today that has now taken an agent and this agent can do sales, support, operations, and collections. It used to be like four people on a Zoom call. This founder journey is so hard. You are depressed. You are anxious. You can't sleep because you're trying to figure it out and it all becomes worth it because at the end of it, you get to look back and you're like, 'Wow, I changed an industry.' I always try and optimize a life for the least regrets versus the least failures. And it's just better to try and fail than not try at all.
Today on the Upwind podcast, I'm joined by Michele Romanow, one of Canada's most influential entrepreneurs and investors. Michele is the co-founder and executive chair of Clearco, which has funded more than 10,000 companies and deployed over three billion in capital to founders around the world. She's also known as one of the youngest dragons on Dragon's Den where for 12 seasons she's invested in and mentored entrepreneurs across Canada. Michele, welcome to the Upwind Podcast.
Michele, out of I mean you are a professional, professional, professional investor, right? Not just in the company that you started, but
That just means I've made a lot of mistakes and lost a lot of money and learned from those mistakes.
Exactly. That's what we're going to talk about. Yeah. So, professional investor with your startup but also on Dragon's Den. Yeah. You must have seen thousands of companies. What are some of the features that in 2026 that you're looking for in founders and their ideas?
So, this has all changed all over again. Like I think that my entire criteria set for what we were investing in the last maybe 15 years is so different today. And in many ways the perspective that a founder has to take is it got way easier for me to move way faster because the reality is that most large companies just by default can't move quickly. And so there'll be so many things that will be disrupted by founders that know how to use AI in a really smart way. And like I mean there's just crazy examples that I can think of. There's a company today that has now taken an agent and this agent can do sales, support, operations, and collections. So let's say you finally get on the phone with a customer you want. You have no idea if the customer hasn't paid you, if you can upsell them a product. And that used to be like four people on a Zoom call to talk to one person. Now that's happening. You know, today that company's called Kavak, which is the Carvana of Mexico. And it's dramatically changed their sales. And so it's both old businesses will be transformed with AI, but I actually think founders have a bigger opportunity than they ever have. And so not only is it always when you do investing about the character and the founder and how fast they're executing, it's now how much they have used the tools to really build something and have they had that critical eye to them because you can't trust AI with everything. You still need a human in the loop, but are they using that to dramatically change their cost structure?
Right? So that example just for people who are not as familiar. Like how exactly is that working? They're sales, collections.
And it's one agent. Yes. So you're effectively talking to an AI that has all of the information from their internal database. So they can ask questions about, you know, collections. Let's say you owe us money. Here's how much you owe us. Oh, but really you don't owe us money. It was actually a mistake on our end. So now a support person, that same person can fix it and then wait a second. Oh actually you want to change your car so can we sell you an upgraded model? Like that did not exist in one human before in a big company and now with an AI agent it can. And so I think we're just seeing some of these mindblowing examples that will really change the way businesses are built.
Yeah. Yeah. I saw a company last week at the Acti event and they're enabling this but it looks like a real person that's talking to you and then they have all this backend capacity, right?
Sane. Yeah, it's insane. Sometimes I get calls now on my phone and I'm like talking to an AI or a human. I just want to give them a test and ask them their favorite food or something.
I know. Like Bory was one that really was the first one to blow my mind in that regard.
For sure. And it's when you talk to these AI agents, the language processing itself is actually getting very, very good.
Yeah. Yeah. An Australian, a Jamaican, a Barbadian really easily.
So the founder, are you seeing a bias potentially towards younger founders because they maybe are a little bit more off with the AI?
So I'm really opinionated that like good ideas can come from anyone and anywhere. And there's some stats that there's, you know, very successful founders in their 20s when they're first learning and very bold. And there's also very successful founders in their 40s and older. Like I'm a big believer that it is never too late to start a business if you have a growth mindset. If you are like, 'Oh, it doesn't need to be done this way and yeah, I'm going to try this new tool and it's not going to work, but I'm just willing to continue to do that and continue to personally be learning.'
Yeah. Yeah. Now that we're talking about this, I mentioned so for the last 15 years, we said that things have changed so much. We were really building SaaS models, right? Like Salesforce, HubSpot, all of the, you know, we have companies still spending thousands, hundreds of thousands, millions of dollars a year for licenses. And now we have like OpenAI and AI where we can create these models that are personalized for each and every business where you have four and also take care of four different departments at the same time. How is that impacting your investment strategy?
So I think people are still in the phase where they don't quite know what to do and you can see the market is punishing some of them. I mean, PagerDuty is a company with I don't know half a billion dollars of revenue that's now trading at basically a one times multiple to that whereas I mean even a couple years ago you were seeing SaaS companies trade at like 10 times forward because people saw SaaS revenue is so stable right every company grows a little bit they add a license every year and once you put software into a company it's very, very sticky which means it's very hard to rip out today and my initial thesis is well all these software companies will just adapt AI tools and they'll just continue to sell. But I don't think that transition has been as quick as I at least I thought it was going to be because again you get to the challenge of these are very, very big companies. And so in some ways the AI tools are the most advantageous to founders because they don't need to be perfect. As a founder you're testing things. Your number one goal is to figure out product market fit. Like does anyone want the product I am selling? And constantly be listening to your customer and to your market on what's working. And so now you think about it to create an app used to be like you had to make a set of screenshots and then you had to hire a designer and then you had to hire some developers to build it and then 12 months later 18 months later you could launch a product and you're like wait nobody wants this and that was like the scariest moment as a founder today you're like can I build something faster and can I do it? I think the other really remarkable example this past week is this Cal AI company, right? Did you follow this story?
So, it's some high school students that figured out that you're probably 90% accurate if you just take a photo of your food and it tracks all of your calories and macros, which is the business that MyFitnessPal has been building for the last 20 years. I mean, MyFitnessPal has 25,000, you know, foods indexed or something something outrageous where you could find anything. But if you've ever used one of these calorie trackers, you know, you really use it for like two days at a time because it's like so much work to type in every single ingredient and every single portion size. And so these guys started the company. They were doing, you know, millions of dollars in ARR. They did their standups on Sunday because the founders had to attend high school classes on Monday. And MyFitnessPal just bought them last week because they were like we are not going to catch up to this and this is clearly putting a huge threat in our business model we've been establishing for the last 20 years. So I think you're seeing examples like that where again high school students, the cherry on top of the story is that they got rejected from universities. These are the best types of people that could have, you know, gone to a university and they already have an exit because they have real revenue. They got to build a product. They got to test it. They had a ton of paying customers. So, I think this is where people should start feeling like we just built the new iPhone and when the iPhone was built, we were like, what do we do with this? I guess we can take pictures. I guess we can use maps. And like it's that second and third generation of companies that came onto the internet that really changed that.
Yeah. Do you know from an investor perspective is it now with the you know these your early stage first check investing you're super looking for some traction for
Well you have the ability to get traction right with like $150 of AI credits. Like just think about that that didn't exist before even if you found the best software developer that was right at a school that was doing you a favor, that had equity. Like to get an app off the floor, it was like 10, 20, 30, $40,000. Like today, you can start building something with 150 bucks of credit. Like anyone can do that. You know what I mean? Anyone can be like, 'Okay, I'm eating rice this week and I'm going to spend money on seeing if this works.' And so, you know, I think that's a pretty big game changer and it's also a huge game changer for different markets because you used to have to be where these talent markets were and you used to have to find the right people and recruit them to your team. Now that AI can get so much of a company off the ground in the early stage, you know, it's really like your own motivation that is really your only barrier, right? Your own energy.
Yeah. With that founder's energy.
Okay. So, moving now over to investing. And your investment strategy for 2026. What can do you want to is can we talk a little bit about that?
Sure. Yeah. Yeah. I think I see three major things that I'm still really excited about. So, the first is this layer of AI tools, AI applications. I think people are now figuring out that there's going to be very big, very well-backed LLMs. So no one's like there's going to be less of those built, but people are going to build really interesting applications with AI. And there's a ton of debate on whether, you know, you rebuild the accounting firm, you know, AI first or you build a different application. I think that world of opportunities is still very open. The only challenge there is that the same way that there's no barriers to entry to start, there's very low barriers to entry to start, but it also means there's very low barriers to entry to compete. So then if you build something and if you're getting critical traction, someone can instantly copy, but there will still be brand, there will still be PR, there will still be, you know, the attraction you get from your users, which no one can really take away. The second area I remain excited about that I've done a lot of investing is health and wellness. For whatever reason, we've become sicker than ever before and people really care about their mental state. And some of these stats just blow my mind. Like if you were to ask me 10 years ago if we would stop seeing 20-year-olds drink alcohol, I would have made a bet a 100 times over that that has been the case since the start of time, right? And today we've actually these are very meaningful statistics on, you know, the number of people that have stopped drinking. There has been more people that have just been focused on everything. One of my investments was a company called Culture that just does cold plunges and saunas. They've done tremendously well with everyone that wants to install these in their homes. And so I'm always interested in that space and what people are doing because I think people when it comes to their health and using kind of natural cures to do stuff are just very price insensitive. They're like I'm willing to do this because the cost of an illness is just really, really high and really, really painful.
And then yeah I mean it's the oldest line ever. A dying man only has one wish right? It's like if you're healthy you can have lots of wishes. And then probably the third space, like it or not, is that we are in a time of way more war than we've ever seen in our lifetime. And so all the technology that goes into defense and military has really exploded in the last couple of years.
Yeah. No, it's very interesting those defense decks that come across my desk sometimes. Yeah. It's What are you excited about? learning. I think energy is huge. Yeah. I think that we don't have enough energy to support the AI and everything that we need for that and the grid in the US is only so large. Yeah. So I think a lot needs to go into that. Um yeah, these AI applications are incredible like you said like easy in, difficult to build the moat.
Yeah, of course. Um, yeah. And I mean, but also like later stage opportunities that are interesting. I've been looking into those. There's some interesting later stage companies that have crossed my desk.
Um, yeah. I mean, you're always wondering like, okay, you can invest in real estate.
Which is great, especially in a beautiful place like Barbados.
Yeah. Um or you can invest in like globally accessible liquid asset class more liquid asset classes that have like asymmetric upside but at the same time as we've seen this week like asymmetric downside too right.
Asymmetric downside I mean look you can never predict the world and I think this really comes down to a bit of a balanced portfolio right you can have some real estate in there you know you should have probably 10 to 20% startup bets in there which are totally you know I've lost a lot of money and the thing with startup investing is you lose a lot of money on things that you would not expect, right? Like I have a company that is the leader in the industry they created is incredible and it was like the two founders just started fighting. They started fighting for a lot of different reasons. And it's like the whole company ended up suffering because of these founders basically having a breakup.
Yeah. And so you get situations like that where you can't totally predict it.
So you just go in with an open mind and looking for a deep moat and looking for something competitive and then a little bit of this is just true risk capital.
Yeah. I tell founders that I'm working with sometimes like founder risk is the greatest risk apparently. It's like the number one.
So hard when you're cutting out your company and you're giving one partner equity and
Yeah. Yeah. the second and third order consequences of that.
Yeah. So, I will say a couple things. So, I really admire sole founders. I've never been a sole founder. I've always had a co-founder. You know, Anatoli and I have done tons of different companies together. Andrew and I built Clearco together and it's just really hard because it's like a true marriage and, you know, no one has the exact same skills, but they need to have the exact same pace. You know, if you are not working where like my best way to describe pace to people because most of the founders that we invest in, I feel like I still need to pick up the pace at which they're moving is like you have four days in one day. You have a day from like 8 to like 10:30 and then you have another day to iterate on something before noon and then you have another day in the afternoon and then you have another day after dinner until the night. And so you think about I always think about I can go at least four times faster than the average person because they're moving quite slowly, right? They're just in their structural grid of what they can do in a day. I'm like, well, we can test something in a week. And if you keep driving deliverables, you can move very, very quickly. But I mean, I would still say that's the number one thing I see like good versus great founders is just the pace that they're trying things, right? It's like, think about it as a sports analogy, right? You're taking a 100 shots on goal versus 10. It just doesn't even matter if you're perfect. You're just going to win because you're going so quickly. And then people miss that when you go fast, you sacrifice a bit of quality, right? You don't get a perfect product out there, but you get it out there. Because the reality is that even if a product isn't perfect, if people really like it, they're going to want to buy it. Like, we've all had that experience where we see the perfect thing we want on the internet, it's like, we entered our credit card number once, it's not working. We entered our credit card number twice. Like got off the bed, found the other credit card, entered that, and I was like, 'Take my money.' Like that is the experience you want to have as a founder when you're like, 'Oh, my customers actually love this.'
Yeah. Yeah. No, I've always known you for exceptional work ethic, right? And you just said it here, four days in one. So, four days in one. Founders listening, it's about four days in one. And it's like, you can see it. It's like the founders that get back to me at 10 o'clock and they're like, 'Just thinking about your idea here. What if we did this?' And then I think one of the craziest things I saw was we were on a call about a supply chain issue with a company. So we were on with their manufacturer and them and something else. And while we were on the call, there's a lot of people on the call. So I was scrolling and I saw a really good ad format that would look great for their product. And I forwarded it to the founder, you know, not thinking twice about it. And I was like, 'You should test this.' And so we finished the supply chain call, which was like an hour later. He obviously forwarded it to another team member. And at the end of the call, he was like, 'Michele, is this what you meant?' And I was like, 'Oh my goodness.' Like, you don't bet against speed like that because the founders will just always figure it out.
Yeah. Four days in one and speed.
Yeah. One hour marketing campaigns.
Yeah. That's so Canada, Dragon's Den. Yeah. And I've been thinking about this. I feel like Dragon's Den has been such an important institution for Canada. It has like not only does it shine light on problems that you guys have as a culture or in your society and solutions for those problems. Yeah. Like and I feel as though in the Caribbean for instance, we could really use more of that. And I'm going to shift a little bit over to the Caribbean.
Yeah, of course. Um, how would you You've been here for a little while.
And you're this incredible entrepreneur and you've seen the world and you've seen Canada and you've seen us.
Like and you're a problem solver.
What are some areas that where you think that we could we could build and change and accelerate?
Yeah. So, I love the Caribbean. I love Barbados. Um, this is just there's nothing that beats a Canadian winter like going to Barbados. And I actually think there is a tremendous amount of really creative people here. And so that's where most startups come from is people that are really creative and they're creative about how they solve they see a problem and they're creative about how they solve the problem and then they're willing to work at that pace that they're going to need to do. And so I think the same way and I mean look we should do a Dragon's Den here for sure. There is infrastructure in Canada that I think is worth copying in Barbados because at the end of the day you need a set of entrepreneurs and there's some great founders here but they need to know each other and they need to have a bit of the group where they can be like oh I had this problem what did you do and like oh this is really hard and like oh this is how I solved this like stuff like that makes a bigger difference than you think because you are really alone on this journey. Like it's really like you against the world. It's you that's steering greatly. It's you putting your reputation constantly on the line. It's you constantly fighting for customers. So when you have a network and investors and people that can tell you, 'Oh yeah, like you're going to have the worst day of your life like seven times a year as a founder and someone needs to be like, 'Oh yeah, it's okay. I remember the first time I got sued. It felt miserable.' And then it just means that you've made it. Someone's worth suing you. Those are really, really scary moments that a lot of people that have done this before can help you navigate if there's some of that. And so, the power of Dragon's Den is a couple things. The first is that it gets everyone thinking about problem solution, right? It's like, oh, I've never thought about, you know, as a mom like I just didn't have this piece of clothing that fit and now people built adaptive clothing or something. And then it is this natural
There's always been a tension between people with money and people with ideas, which has existed forever. I mean, before Dragons' Den and before there were kind of investors and founders, it was like, you know, if you were a civilian and you had a great idea, you went to the king. And if the king liked your idea, he backed it, and then you could kind of change the course of history if you had the right backing. And so there's always been that tension, which is really fun for audiences to watch. You know, what's going to happen in seven minutes? Are they going to get the money or are they not? And then I think, yeah, some of these early-stage accelerators and some of these success stories just really allow this because there are really amazing founders here. They just need to know a few more people.
