Serial Founder and Dragon: Michele Romanow on Building, Investing, AI & Motherhood

To be here. Yeah.

Yeah. I've only been working for 12 hours. I did a full day of Dragons Den today, but this is actually the most fun to kind of share really personal stories in a much more intimate setting.

Yeah. But that's the attitude I've always took for everything. I think a lot of people take this attitude of like I can't squeeze one more thing in. I would rather be like 10 minutes late and try and squeeze three things in. And I actually think that's gotten me pretty far. You know, like 90% of life is just showing up. Like we all got to get out of bed. It's all imperfect. And we're like, I'm just gonna try one more thing. So, of course, I showed up.

I've always thought of myself as the same person, which is I want to build something from nothing. And I want to be a builder at my core. I want to see a problem and not complain about it, actually just go fix it. And I think that I come back to that point and like the trendy word for this is gratitude. But I come back to constantly I was born in a time in an era especially for women where you look at the options my grandmother was given. Be a school teacher or be a secretary or be a nurse. And I was born in 1985 at a moment in time where there was lots of women that had done way harder work before me. And now I could be in a world where if I saw a problem I could go solve it. And so I've just always thought of myself as a founder at my core. I now think about how I can enable the next generation of founders and how I can make more entrepreneurs. And so that's been I've learned every lesson the hard way. It has been like painful learning all those things. But now if I can help more entrepreneurs by investing in them, by giving them access to capital, like that's a great legacy for me to leave.

Yeah. Impulse, Base, Ziotics. Like there's so many. I think there's like 50 angel investments that I've done.

So many success stories. And also, you know, some failures along the way.

There are people that I meet now and I just look in the whites of their eyes and it's almost an intuition thing and I just don't want to bet against them. They're just so persistent. I mean, Mark Lafleur is like the most perfect example of this, right? Did not come from a fancy family. Had sold meat door-to-door and he's like I am going to build this company and started selling frozen farm-to-table meat from farms to people's homes. And Mark and I fought a ton in the early days, right? We fought about what the definition of local should be and if he was spending too much money on advertising. And we had this really good relationship on like the push and pull. And when he came to me and he's like okay I really want to exit like I'm getting exhausted I was like, okay, this is what the spreadsheet is going to need to look like. And in 6 months, he had done every single one of these things. We found him a buyer. He exited the business with very small investors for 17 million. He became a full circle dragon this year, which is he came back for a guest episode where he was a dragon with five others and got to invest in new companies. And I think of Mark as like a perfect example of someone I just won't bet against. Like the guy ran an ultramarathon for fun.

That's 100 miles. Like I have done a marathon and that is exhausting. And I think fitness is always a good analogy for what this is. Like being a founder is being able to put up with the embarrassment for a long enough period of time that you find something. That is really what this is. So, that's one of the patterns is an extraordinary amount of persistence. But that persistence is not I'm going to bang my head against the wall and keep trying something. It's constantly iterating, looking at your customer, seeing what they're saying, seeing what makes sense, seeing what the new technology that can help you move faster is. Then I like certain spaces. I think that right now if you are in anything health and wellness people really care and are very price insensitive. I think if you look at AI there's an incredible amount of things happening and I think if you look at defense there's a lot happening there too. I see those three areas and so you have to pick the right river at the right moment in time. You know if we're like we're going to remake the fax machine like there's eras that are over. So, those are some of the patterns that I've seen.

Yes.

I think there's this advice that's given like so generically so often that it's like do not quit. Like that's terrible advice. You actually need to know when to quit and when to start moving on your next iteration. You know, Clearco did not start as a company that did non-dilutive funding for e-commerce brands. We had an entire project we worked on. Andrew and I decided that fintech was going to be one of the big deep streams of the last 10 years. You have to remember where we were in 2014, right? We were seeing Uber in its heyday, Airbnb in its heyday. Social media had just had this 10-year explosion. And all I could think of is where is the customer expectation going where the conventional companies are not going to keep up? And it had to be finance because banks are big and old and regulated, especially here. And the consumer expectation was changing. Like now you could press a button and get an Uber. That expectation was going to be brought into banking and here we were on a 20-minute phone call to change a pin code. Like no customer was doing that. And so I was like this is going to change. In addition to that, you know, the tallest towers in every single city in the world are banks. So, this is a big enough industry to chase. And it didn't start off that easily. We started building a daily pay product for Uber drivers. We worked on that for like 18 months. Like we had deployed a lot of money. We had raised a seed round that, you know, finally we were like, oh my gosh, this is so hard to service. The customer service costs in this are really expensive. You know, this is not going to work. Had to throw the whole thing out. Then we actually built a whole financing product for founders that had Airbnb properties and portfolios. So, if you wanted to add a new property to your Airbnb portfolio, we would finance that. I mean, these were not small experiments. We put $30 million out to Airbnb hosts.

And, you know, it was really hard to get access to their API. It was really hard for us to get clean data, which is impossible if you're running companies at the beginning. And it was then that I got on Dragons Den and one of the unique things about Dragons Den is the amount of companies you see in a short period of time. I see a hundred pitches in like 15 days. So, you start to really see patterns. And the pattern I kept seeing is there are so many e-commerce companies. They're here giving up 10% of their company for their first $100,000 and they're going to spend all of that money on ad spend and inventory and there had to be a cheaper more data driven way to back that. And that became the iteration that worked.

That's the other point. And again, I'm never afraid of that. There's tons of great Dragons Den companies that can build 50 or hundred million dollar businesses that are incredible outcomes for the founder. You just need to then not put too much capital and put too much dilution if you have limited upside.

It's this ability to move on and solve problems quickly and understand you are never out of problems. I think this was one of the great myths I told myself in the early days that it was going to get easier as I got bigger. You just upgrade your problems. There's just a whole new level of problems. And I think it's actually going to change because most of the problems you develop as you get big are people problems that there's a lot of people that you're now paying very well that really want to protect their job. And so they're like, oh my god, I'm this great executive. I went to this place. But really, it's very much in their own self-preservation that they want to see how valuable they are, right? And so, you get these moments where like at some points I would be like, there's like seven executives commenting on a Google doc right now. Like no one is doing anything. We're all debating something. And so to be the person that is constantly rewarding action, the leader that is constantly driving. And the other thing that gets companies out of hard problems is leadership that is constantly pushing your team. And so one of the funny stories that was always told about me at Clearco is there was this Michelle tax and I kept like being like what are people talking about the Michelle tax and they're like oh well if you say you can do 50 million Michelle will just like think the number is 70 million. But that is what all great founders do. They push their team to believe that they can do more. And when you set the goal really high, you kind of always fall in the stars. If you set the goal low, you'll just kind of run into the floor, right? There's no limit. And there's a lot of excuses for why things don't go well. And so the thing that differentiates the mediocre companies from the incredible ones are like, solve a problem, keep going. Solve a problem, keep going. Like that resilience and that constantly moving from problem to problem is what wins every time.

Yes. And everyone from a non-technical to a technical role is expected to ship code to production. So this idea of like you're a management layer that just coordinates people and teams but you're not in the work anymore to especially in AI totally dead. It's totally dead as a concept. Totally dead.

I couldn't agree more. Like first of all, let's level set. Today a 200 person company could now look like I don't know a 25 a 50 person company with a bunch of agents. Like the ability to scale without people will be completely groundbreaking into how we build companies today because that's a great attitude. Everyone has to be an individual contributor or at least like a percentage of your role. It's just like I'm just a manager is yeah. No, that has to be dead because you don't stay close to the customer. You don't stay close to how hard it is. It's very easy to tell people to do something when you're not doing the work yourself. You have to think about it as a marathon and you're the pacer. You're running alongside them. And it really really changes people's perspective. And always as a leader, this is one of my hacks. When people say that they can't do something, again, I very politely do it for them. Because number one, they have to know that the work is never below me. I'm not a person that believes that I will take out the trash if the trash needs to be taken out the day before our buyers come. Like truly, check the toilets. CEO is chief everything officer. It all rolls up to you. So, you have to show your team that you're not precious, that you will get your hands dirty and you will do it. And then the second thing is that what they're seeing as a challenge isn't really a challenge. And so, you know, you don't see an ad set you like, like I'll pull out a camera myself and I'm like, this is the shot I want. Or I'll get out a post-it and I'll sketch exactly what I want the page built that I want to see. Or the biggest one is sales. They're like, that person won't close. You'll get on the phone and I will call and I'll call them on speaker phone in front of them because I want everyone to pick up on what I'm seeing and I'm doing that they might not see. And again, you have to do this. This is not a game of ego. This is not I'm better than you. This is a game of we're a team and then everyone feels that teamwork and that competition that we're just going to make this work and then people are way more honest. I think the other thing that happens within organizations is people do a lot to sugarcoat their own numbers and within like you should always put your best foot forward externally but internally you should be ultra critical. You should be like, oh, what could be better? And like, are we really making money on a per unit basis if we include every single highlight reel? You see that coming back to your point of like people wanting to protect their roles. And the more senior people you get, the harder it is. And it's your job as the founder to be constantly turning over these rocks and being like, what are the challenges in this business and what am I seeing that you're not? And I can tell you there's many times and my biggest fuckups are when I didn't pull on a thread where I had an intuition on. I'm like something doesn't feel right with these unit economics and something doesn't feel right with this investor and if I had just asked another 20 questions I would have got it. But if you can get your team to the point that they're not protecting themselves and it's really safe for them to tell you what's going wrong you solve those problems way faster. And now I think I mean we have the help of AI. There's going to be a lot more ways to analyze and look at data without someone going at it. I mean again my favorite phrase from consulting is show me the results and I'll show you the data. Like always remember you can cut data in any way that you want to if you want to put it on a pitch deck but why are you lying to yourself? Like you're the one building this company. Your outcome is if your customers are happy. So I always take a very critical lens to that part of building.

When I like to hire people, I screen a lot for agency. So, I look at this is the world happening to you or are you happening to the world? And you have to be happening to the world and anything that looks like a victim mindset and I can't fix this and I can't build it and there was too many challenges, you know, you're telling me a hard story about yourself and it was all your boss's fault. Like, I just don't believe it. Even if it was, why didn't you fix it? That's your job to fix it. Your job is to like build the best possible company we can and you rarely do that by looking at a mountain of excuses or just accepting things at face value.

Oh, you have to push. You have to push and you have to encourage people to push. For sure.

Oh, and I have a follow-up depending on what your take is.

I mean, I would still like the first two are still the most important to me. If you like love something and are obsessed and moving quickly, you know, you're very hard to beat. And that applies if you're a founder or you're working at a company. I think ability to take feedback, we all have moments that we're like, I just can't hear one more piece of negativity. You know, I did most of a psych degree alongside my engineering degree. And there is like two things I'll never forget from that experience. And the first is that people have a feedback ratio that they can take. And this is especially true with their partner in life, but it's like 7 to 1. Like it's a mind-blowing number. Like I have to hear seven good things for me to really digest one negative thing. And psychologically we think it's one to one and I like hey I said you're great or the sandwich thing bad thing. Exactly. But we really need to have a lot of encouragement to feel good about ourselves. And so I do I think I do try and give a lot of positive feedback with negative feedback. I think that's really important if you're the leader. And the second thing I remember learning in psych is that when they look at all the personality traits and they survey all the people, people always gravitate the personality trait they want the most in anyone they're dealing with is the ability to be genuine and authentic. And so I just think it doesn't matter who you are, just be you. Yeah. And you know, I have been extra in lots of things in my life, but I'm like, you lean into who you are because people just know that it's real and it's very very trustworthy.

Obsession speed. No, that was a great answer.

So, and but it comes back to what you're saying about yourself and trust because I actually think that's part of the answer, but you kind of answered it. But so still speed even with AI tools completely relies on your own agency.

Like all the tools are out there. You can choose to use them or not and everyone has it. You can write a speech where you're like, give me the first AI slop answer. Or you can spend an hour and a half with it being like, make this funnier, make this wittier, think of something else. And so I think agency still very much matters there. But what people confuse is they confuse your own personal speed with now what's building competitive advantages in companies. So usually startups had a competitive advantage just being faster because the one thing big companies can't be is typically fast. They have regulation, they have compliance, they have lots of people, they have negative nancies in their company, they have brand risk, they have reputation. These all create slowness. And so typically when you were a startup, you could be like, oh, I can just go really fast and I can win by being faster. Now that's like being eroded away because you know companies can move a bit faster but that's very different than today what creates competitive advantages. So now the software moat has gone from this to this because now you can say duplicate this perfectly. I mean this PR stunt this company did where they duplicated every single YC company in a weekend is still mindblowing to me as someone who spent 20 years building software. This idea that you can be like, go build this and it again, it's not perfect and it's probably not security compliant, but it's 80% working is insane. So then you're like, okay, so the software moat is gone. What are the new moats? Well, that doesn't create customer trust any faster. So we're still going to have to live in a world where people really trust and really build a brand based on storytelling and customers and everything else. And it means there's going to be way more competitive advantages built in distribution. And so I think that's the framing we now need to use. And so I would never confuse being fast personally and obsession with something that will always win. You just don't bet against a guy that runs 100 miles. Like they're just going to obsess. They're going to wire. They care. But it will shift where we create those competitive advantages.

I mean, let's look at another example from D to C. I mean, every major beauty brand that's been created has either been in the last decade has been a major makeup artist with millions of followers or celebrity with millions of followers. I mean, this is a business where you make a dollar product and you sell it for $42. Like, your only advantage is distribution. Labs are very good. There's a reason that the entire beauty culture is obsessed with dupes because they are quite literally duping. They're saying, go create me a version of this. And you can do it because the price is really on brand and marketing. It's not on the product. There's just not expensive ingredients in cosmetics.

The number one metric that will never lie to you is your repeat rate. It applies to almost any industry universally. You can convince anyone to do something once. It is very difficult to keep people coming back. And some people have natural rebuild models in their cycle. I mean, when you buy shampoo and you're in love with a shampoo, your hair gets dirty every 3 days. So, you got to keep buying the product. And software companies did an extraordinary job of transitioning from buying literally Microsoft Windows 95 CDs to now you're going to pay for this per month per headcount. I mean very sophisticated models that I think got so aggressive that they're all going to go away because now people have a lot of incentive to rip out those cost structures that have previously been built. Always go back to customer return rate because people that come back and do something time and time again and love your brand and love your product and again that can be created with distribution in different ways, right? You're selling to government. There's a huge barrier to entry and getting approved and getting inside and having the relationships like those create really deep moats when you have very unsexy spaces. I mean that is generally a great moat. I mean everyone is thinking about how to create a beauty brand and a skincare brand and a consumer goods brand. No one is thinking about how to use AI to fix the title insurance industry and how to build better emergency equipment when an ambulance comes. Right. Those will be I love going into unsexy businesses.

Exactly. People were like.

Yeah. But like did you like fish and did you like coupons and did you like I'm like I like taking market share. That was really none, right? You get excited about a product, but then you get excited when you see a spreadsheet. And I would never, you know, confuse those two.

Exactly. Even if there's a long cycle a brand can still build trust so your Patagonia example is amazing people know that the stuff is built for life I think we're all living in an era of mass consumerism. All of us have basically way too much stuff and you know it's now work to be like I need less. And so they've built a brand of trust where you feel like you can come back and you know they keep creating needs for our outdoor experiences that we can go to them for.

Start asking an enormous amount of questions to everyone you meet. I think you would completely underestimate how curious I am in my day-to-day life to this day. It is like a part of my personality. I'm a learner. I don't like not knowing things. I believe that everything can be learned. And C this is really important. The best pieces of information are not available on the internet and they are not in books especially about industries. They are things people tell you. And so you just have to ask I mean call founders like some guys like I work in the garbage industry. I'll ask like a hundred questions about why this business is the way they are and why we don't recycle more and why this is happening because people will tell you all sorts of the challenges that they will never write down because there's a lot of unsavory things in life. There's a lot of reasons that make no sense and don't have a good PR spin and are not really great things that we're doing to begin with, but they're working or what's not working or where people haven't seen that. And so that starts with that curiosity. And I mean, look, I get a lot of inbounds for all sorts of advice and requests and I can't possibly take them all. But when someone messages me and they're like, I'm going to build another Snap Saves app or I'm going to build another Clearco. Will you give me advice? I literally give people my cell phone number and I'm like, call me for 10 minutes because let me save the next 10 years of your life. I made every mistake in that industry. I can tell you where the hard parts are. And you'll find actually a lot of people that are more helpful than not. And then, you know, in the worst case scenario, you can just, you know, ask a bunch of like strange questions. Some people will, most people will talk to you. Like, if you're curious enough, most people will talk to you. And go in with really intelligent questions. Like, read everything you can on the internet. But remember that the best pieces of information are never there. You have to go find them.

Yeah. You should be constantly aiming to be the dumbest person in the room, not the smartest person in the room.

Oh, yeah. Did you hear that story?

In a lot of ways. That was one of the most important childhood things. I just told that story recently. That was so interesting. I'll just share the highlight reel of that again. So I switched schools in grade six to grade seven and went to elementary school in Regina. I was one of like three girlfriends and they all... I mean one of my friends turned out to be a brain surgeon. The other one clerked for the Supreme Court. These ended up being extremely smart girls. But all I remember in grade six is I was the dumbest of the three. And that was my whole set.

It was a hard place to be, especially at that age. Formative age. One of my friends like she could play piano much better than me. And I was like very devoted and became actually a very good piano player after that. And the other one could like read a chapter book way faster than me. Like these are your metrics when you're in grade five. And I just felt like this underdog. And I remember switching schools and working so hard. And this grade seven teacher came up to me after the first semester and she's like, 'You have the highest average in school.' I was like, 'What do you mean that's impossible? I'm the dumbest of everyone.' Like I knew I was like working harder than the kids that weren't paying attention. But in my head I just never thought that. And I think that early confidence was really important to me. But yes, do not be afraid to be the dumbest person in the room.

Sure. There's an achievement trauma. The other thing that I always have in the back of my brain, this is my own like personal hack, is right now is the least stupid time to ask your question. Every moment that goes on after this, if this meeting continues, if this relationship continues, like it's worse to get worse. Because if you didn't know this two hours ago, why didn't you ask me two hours ago? And again, you can't... you have to like read the room a little bit. If there's lots of people in the room, you can't dominate the space. Use your brain. But I remember that. I'm like, I'm going to ask now. And I think that gives me a lot of confidence.

I feel like asking people the questions when you don't know something also builds the trust and authenticity that you were talking about because they feel like you're being honest and upfront with them.

Oh my gosh, we're so nuts. I still think about this story and I'm like, how on earth did we convince ourselves to do this? So, there was a couple things that were like truly at play. So, the first is I met Anatoli in undergrad and... business partner. Yeah. My business partner and my life partner is amazing. And he like found me in this library and he's like, 'Hey, what are you doing?' And I was like, 'Oh, I'm getting like ready for this business plan competition.' I started this little thing called the Tea Room in undergrad. And he was cool. I was not cool. He's like, 'Oh, I'll come tomorrow.' He's like, 'Oh, you get like prize money that's like, you know, gifts in kind.' And I was like, 'No, they give you like $25,000 to start a business.' And he's like, 'Oh, that's pretty good.' And I was like, 'Dude, it's a Saturday morning. Like there's no way he's going to show up.' Like Saturday morning he shows up. He was invested. And he was like, 'Hey, you didn't win, but like we should do this next year. Like we should do the business plan competition circuit.' And so we spent like six months just brainstorming different ideas and there was nothing we weren't afraid to touch. Like this became the game that defined my whole life is constantly talking about opportunities. I mean we'll walk through an airport, we'll get in an Uber, like everything we're looking at is like everything is an opportunity. And it's a great life hack because you're way more positive when you're looking for opportunities instead of negativities. Like you have a lens that's constantly focused on what the opportunity is, not why doesn't this make any sense. Anyway, so he convinces me to do these business plan competitions. We come up with this caviar idea. Remember what... like why worldwide supply of caviar was down by 95%. I mean that's a pretty good... we had overfished the Caspian Sea. I was like, I guess we can do this. We like randomly went to go visit fish farms like in the US. I remember buying a ticket to California return for $400 and I was like, 'Okay, we got to go.' We had no money. Anyway, we won like six of these business plan conferences. We graduated with $150,000 in prize money. Insane. And I had job offers from consulting firms and from engineering companies. And I was like, we should just try and do this. And it was scary as hell. I mean, we got in an old Toyota Camry and drove to New Brunswick. I mean, we lived in a motel room for nine weeks when we were there. And this is the best part. We were like catching fish all day and it like didn't have a window that opened. It smelled so bad. Like the whole thing... like you're just like catching fish and then you're removing the caviar yourself or like how actually going... we literally had to buy... There's a very long story. You had to like find a fisherman. We had to find the right equipment. Like we processed the fish ourselves. So yes, that means we like made the caviar. People are like... we did like some bonding retreats with our co-founding team. I was like, guys, you have not... like what a bonding experience is. Like this is like hard physical labor. This is like figuring out how to make the product. Like this is cold calling restaurants from our flip phones.

Oh my gosh. To like find our first fisherman. There was like... But that level of scrappiness is what you need forever. You cannot lose it. Like I have a great story where we wanted to close this deal with Uber and we knew lots of senior people at Uber, but I hadn't met Travis at the time. He was running the company. And so we figure out how to go to an event where he's speaking. And I remember there's like multiple dinner tables and like I'm over there. He's eating with like... this is a big conference. This is not like I'm there with a few people. I'm there with like 3,000 other people. And he's having dinner with like Eric Schmidt and like there's many very important people at this table. And I look at Andrew and I was like, well, they say do one thing a day that scares you. So here goes. And I just walked on over and I introduced myself and I just gave him my two-minute pitch and he was like, 'Oh, that's a great idea.' And he's like, 'This is my email.' And like, 'Let's go do this.' Yeah, we're closer than we think. We're closer than we think. And so that level of doing one thing a day that scares you. I think we were really lucky that we had this prize money and we have, you know, forever continued to donate to business plan competitions because we think our whole lives would have been different if we weren't given a little bit of that startup money to start. But I think after that it was really about are you willing to take the risk and are you willing to stomach all your friends being like, 'Oh my god you guys were the crazy fishing people.' Like are you willing to be embarrassed? Are you willing to have this be very hard for not one year or two years? My first exit I was 28 years old. I mean we started when I was 21. That means we were like... that's snaps. We sold as a group on my 28th birthday which is young except like we made no money from 21 to 28. So that's actually a big grind. All your friends are making money in banking and consulting and they're... Oh my god. You seem like... I screenshotted my bank account the day before we sold to Groupon. It had $10,000 in it. Like we were like in it. Yeah, it was hard.

I don't know. I think the first thing is the framing of like I'm not THAT SUCCESSFUL. I'M LITERALLY just a person in the world that like tried to get something done and then tried to do it at scale. I think you just you have to be excited about leaving the world a little piece better. I think having a daughter completely reshaped that perspective altogether. You know, one of your questions was what are the two most exciting things in your life and I'm like, well the first thing is AI because it shows you how fast the world can change and the second is my daughter which shows me what really matters. And so you kind of combine that and I think you get a really powerful mindset.

And then you have to combine that with really good unit economics. People like... this is such a huge mistake so many people make is they're like, 'Oh well people love it.' Like you're giving it away for free of course people want $1 bills for 80 cents. They will always want that. Always want... like that makes me think of like the food prep kits whereas they give you your first one like of course I'm going to take it. Am I going to buy it ever again? No. And so you can get trial but does that trial again back to repeat rate... like it all comes back to repeat rate. In a world of AI, in a world of everything, like are people coming back to you? And so I think those two things are really important. And I never try and lie to myself on unit economics. Like that is one lie I never try.

Yes. At the cohort level it's so easy to be like, 'We'll fix this with scale.' This gets infinitely worse with scale. Yeah. It's true. And you can go and you can iterate a little bit but again there's only so much people are willing to pay. And now we have a very different problem in society. We have mass inflation across everything. We have apples and food costing more than ever. It is going to really push a lot of categories that are not necessary. So people are going to pay to feel healthy and they're going to pay to feel safe. And they're going to cut a lot of other things as like a more luxury or niche good.

Oh, I mean we... the end of that story is we didn't survive. We had the giant recession in 2008. I'm 22 years old selling the world's most superfluous luxury product and it was just time to find the next thing. And so that's okay too. That's back to your four and five don't work. You have to try a lot of products and that's okay. And I constantly like coach the entrepreneurs that I invest in that like, okay if this isn't working like move on to the next iteration. Like you just got to keep playing with it.

Oh, Clearco. Yeah. Without question, developed me the most. I mean, it was a good segue. It was perfect. Yeah. I mean, it was eight years of my life. It was getting to scale. It was growing internationally. It was doing all sorts of things that I had never done before. It was dealing with a bigger team. It was dealing with a large amount of venture capital. Like there was a lot there that developed me for sure.

Oh yeah. There was like products that were people's babies that were not the core business. There was lots of things that people work on and then sometimes you don't know either, right? I mean, we had access to the ChatGPT like 2.0 and 3. We were starting to see the first AI underwriting how powerful this was in the early days and we were trying to like build products on it and you know, you could argue that some of those could have been shut down way too soon, right? But they weren't making money and then you're scared and then you're on the quarter and it's really really hard.

Yeah. So the mission was always how do we make everyone an entrepreneur? And you do that by not only encouraging entrepreneurship, but it's really like starts and stops with access to capital. And every single founder has the same working capital problems, the same inventory problems, the same I need money for ad spend problems. I have a, you know, a purchase order problem. And we then 10 years ago looked at this and we're like, well, there's actually way better data. Customer doesn't even need to submit a lot of data. We can find that from digital platforms where they can't lie. It's very difficult to make your Shopify data match your Stripe data match your Meta account data. And so if we looked at all of those and automated that process, we could deploy a lot of capital. And I mean in many ways I never imagined Clearco and the idea would get this big and not only the scale of like deploying that many billions of dollars. You know the fact that we have a global competitor in almost every economy around the world. I mean this was an idea that we started uniquely in Canada.

Don't please don't we're not giving them any air but there's unicorns in Europe and there's lots of players that have built revenue based financing in India and South America. So I think that the impact was the amount of capital that we have deployed is incredible. The type of entrepreneurs that we have reached. The problem always with capital is that it's dependent on who you knew and it's been that way for like a long time. We look 2,000 years ago. If you knew the king and you had a good idea, your roads were going to get funded and your ideas were going to get funded. And really nothing has changed except if you went to a fancy school, then you had the fancy friends and then they could deploy a lot of capital with you. And there was a lot of trust built in the relationship system, which I have no problem with. There's just I saw the opportunity of so many overlooked founders that had great ideas that had great unit economics that couldn't get access to capital. And so, you know, Clearco still does that today and they do that for hundreds of founders every single year and they've continued to iterate their products so they just become better and easier for founders to use.

For sure. For sure. I mean that was always and again the best part of seeing an opportunity was I saw so many great companies that weren't getting funding and that frankly even on Dragon's Den didn't make sense to be equity deals, right? A lot of these consumer brands would never exit or would never have a buyer, but they were producing cash flow and they could have dividends in their business. So why not take effectively like a royalty-like structure out of their business? There are still so many founders that come to us that would have never been given a chance by other places and then there's founders that were given a chance by every single fancy investor who was like, 'This is great. I get to keep more of my company if I get funded with Clearco.' So I think we have that range. We still have, you know, half of our portfolio is women. I mean people don't understand how big the stat is like in the VC world 2% of venture capital goes to women. That stat has not changed in a decade now. I mean, it changes by like 50 basis points. It's not a meaningful change.

I think people like forget where we were at that moment in time, right? Like pandemic. No, the pandemic was great and then there was an enormous amount of venture capital deployed in 2021. So, everyone's valuations were inflated and then in, you know, in a very short period of time, interest rates went up the fastest that they've gone up in like 30 years. And we're a business that makes money on a spread. I have to get money from that and make a margin on your cost. So when that shifts so quickly, that was really hard for us to pivot. And that was really hard for us to pivot at a time where we also just expanded internationally, had also done some other moves, really not anticipating that. And so I think I mean I think I got it the best way. I got to build this incredible company. You know, the legacy in the company has still continued to do exceptionally well. I brought in a CEO that had worked with us at the company for six months when Andrew Curtis took over. He's done an amazing job. He did an incredible job recapitalizing every part of these debt facilities that needed to be restructured for us to grow. And you know, the company still deploys like a ton of money per month. So, I think I'm just really happy that I had a person that I could have so much trust in and that I had left my mark on a business and now that business continues on without me there.

Yeah. I think I mean I remember there was at one point where we you know laid off three people and it was national news. Like this is outrageous. Like how can you run a company if that's the scrutiny you're under? I mean there was media outlets chasing our employees for any piece of you know bad thing that was happening. I think that this has to stop if we're going to build companies of meaningful scale and take risks in this country.

Like there's... there is no... we have 100% tall poppy syndrome in this country.

It's like as soon as someone gets too successful, we just put all of our resources into not celebrating them, not cheering them on about trying to tear them down. Oh, you're the tallest poppy. We should snip you down. And we protect these oligopolies and monopolies in our country, which I'm like, well, why don't you go chase them? We all know what makes a really good market. It's having a lot of competition. I mean, you can... there's books written about that. I mean, this is the basis of economics, but we really go after entrepreneurs that take a risk and we disproportionately probably go after female entrepreneurs that take a risk. And that's not okay. I mean, look, it is what it is. I'm happy to operate in the market system. I'm just saying if Canada wants to be successful, we should stop.

Because you end up being so worried about what's going to happen and already like everyone knows like every good company read their Glassdoor review. Someone has something terrible to say about every single boss in the world. And I get that I need to have a really tough skin. And I do have a really tough skin, but there's a lot of mischief that happens if journalists continue to press on a company time and they press on all their employees. Like what are we doing here? And we don't have that many unicorns in this country. We don't have many people that have taken a risk. We have a lot of people that build safe businesses here. And so I think that we should be really encouraging to do that because there's a lot of innovation in this country.

You know, I really try not to take a sexist lens to things. I think it again puts me into like this victim space that I hate. But there is a rarity to it which makes it different. So again, if you're the only female in the room, which you are often, then you get more attention. You probably get more press on the way up because you're more rare. And then you probably get, you know, hit harder on the way down because you're more rare. And so I think that that knife cuts both ways. And I would just say in general, this has happened. I think I've gotten a call from every single major founder that's built a company that matters in Canada and the way that the press has chased them on things that do not... irrespective of who you are. And you know, I understand that there's journalism and I understand that there's reporting, but there's also just a point where we're just, you know, you're not even allowing companies to breathe.

I think I, you know, I look a lot about the advice I give my founders and there's like a couple things that are really important. The first is the more money you raise, the more money you spend. And building something that at its core is capital efficient where people understand that and you can feel it when you're in a company. Like there is a way to do a photo shoot for $10,000 and there's a way to do a photo shoot for a million dollars. Yeah. Tell us about it. And if you're showing up to your own company and you're like, 'This is outrageous.' It is. And it's your one canary in the coal mine where that cost creep is going everywhere. And there are times where raising money makes a lot of sense. But you have to really know what you're going to do with that capital and you have to be really really disciplined around that. And then you just have to do the math. Like too few founders actually look at the spreadsheet, right? Owning, you know, a bigger percentage of a medium outcome can be completely life-changing. Whereas, if you're owning 10% of your company, like I've always cared about this because this is actually the founder math that matters. It's why you should take on non-dilutive capital because when you own more of your company, you get a bigger payout at the end. And the other thing is you control a lot less of your destiny the more capital you raise. You have boards and you have people that just need to make three or four times their money before they're even, you know, comfortable with you exiting. So, I think those are like the critical questions you need to look at. Sometimes you get that lightning in a bottle where you know you're going to get copied and it's the right moment, but you have to be pretty certain of that.

I think the VC market is in a really interesting place and I talk about this in both the US and Canada because there has been way less exits because a lot of companies have stayed private for a lot longer, right? I mean, Stripe could have gone public like I don't know five years ago if they were on the same pace that Google was. And so there haven't been the same realized returns in VC funds. There is now going to be a lot of dead software companies in a lot of these companies right now. And so that space is going to shift a little bit there. I mean there still and always will be access to risk capital. I just think you're going to be able to do a lot more with a lot less. And so that's like a huge advantage. Like people are like, 'How big's AI? Is it like the iPhone?' And I'm like, 'No, this is like electricity. This is huge.' Yeah. This is like... this should blow your socks off. But I have another really good framing which is, you know, again with my like never a victim mindset. I like to think of myself as like I'm the elder millennial. I'm 40. I hit every single technology wave at the perfect time. So I was born without the internet. I got a dial-up computer when I was in grade six. So I was just like no phones, no screens as a child. Like they just truly didn't exist. There was a TV with cartoons if you really wanted to watch that. Then I did all of my embarrassing undergrad and high school years without a cell phone. I mean flip phones were just coming out. I mean I truly went to all of university without a cell phone if I could believe it. I had a landline in my dorm. I like think about this now and like... and then I'm a year out of school and the iPhone comes out. I'm like wow I'm 20. I should be running this like crazy product just came out and you know that defined the next 20 years and now I'm 40 having built every piece of knowledge on building a startup and like AI shows up. So it's like a pretty perfect timing of the world.

I'm curious to know because there's always camps... there's like the dystopian lens on AI and then the utopian because of the race to AGI and all the fearmongering around that. It could be true. I have no idea. And the utopian lens, where do you fall in that spectrum? So, I mean, and look, I could definitely be accused of wearing rosy glasses. I think we're there with you of loving it. I think, you know, 98% of the world used to work in agriculture and now it's 2%. And somehow we've all figured it out. Yeah, we did figure that out over a much longer period of time than what we're doing now. So, I think this is going to be very bumpy and I don't think anything's like truly dystopian. I think we need guardrails on technology and I think some really dark and weird things can happen. But generally, I mean, I also just take the view of like why view it as negative? You can't put the genie back in the bottle. Like the only thing that can continue to exist in the past is like the Canadian healthcare system which are somehow faxing things from place to place. Like I'm like, have you guys like heard of the email or internet? The email. Hey guys. Yeah. Just like throwing this out there for you... digital files. So, you know, I'm sure we're going to see some pretty aggressive dark examples. But I think, you know, at any point you can choose to be the optimist or you can choose to be the pessimist. And people are going to build companies that they never thought possible. They're going to be creative in ways that they never thought possible. And it's really cool to have...

Yeah. You have an appreciation for both.

Yeah. Yeah. Is this one big experiment of like natural selection in accelerated form of who will be able to adopt it and become self-resilient from it and who won't be able to adapt? And like we'll just see people gaining incredible wealth and security and then others not being able to. That will happen. And I think we just don't want that, right? The euphemism for all of this recovery is the K-shaped recovery, right? Rich keep getting richer, poor people keep getting poorer. That's not the world. One of the great hallmarks of society was that we had this big middle class in Canada and the US for so long. I think that's still a very fair aim. I don't think we generally do that through more socialism. I think that we do that through more innovation. Because when people can start and build companies, they change the shape of society in the best possible way. And so, you know, I hope that people take the agency to do that because you can do a lot of things on your cell phone. Let's just put it that way. You can choose to read the entire encyclopedia of the world's knowledge or you can choose to play a game and you can choose to endlessly scroll social media.

Exactly. A doom scroll for sure. We all doom scroll. Like we all get into these patterns. But you can also remember you're holding the world's most powerful device and you can do anything with it. And so it's all going to be about individual agency and then surrounding yourself with the people that are taking that individual agency. And I hope we are in the golden era where things are built. And again, distribution does not happen overnight. Whether you're getting an audience, whether you're getting a customer, no one is going to be able to replace that. There's still going to be trust in brands. There's still going to be relationships that people need to have. So it's not like the whole world is falling apart and people can just duplicate anything overnight.