The Iteration Lab
Welcome to The Iteration Lab, a podcast from Jarvis Consulting Group where we explore how today’s leaders are shaped - by their history, their heroes, their heartbreaks, and their hopes.
Hosted by Mike Corbett, Co-Founder and CEO of Jarvis Consulting Group, the show goes beyond the titles to focus on the people.
Each episode features conversations with business and technology leaders across industries, examining the pivotal moments that shaped their careers, the people and mindsets that guide them, the setbacks that tested them, and their hopes for the future.
Through these conversations, we explore how that evolution shapes leaders and what they're building.
New episodes biweekly. Subscribe to follow The Iteration Lab.
The Iteration Lab
Andrew Curtis - Why Discipline Beats Speed
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In this episode of The Iteration Lab, Guest Host Carolina Jung sits down with Andrew Curtis, CEO of Clearco, to explore why discipline - not speed - is what ultimately determines whether hypergrowth companies survive their hardest moments.
Andrew reflects on stepping into the CEO role during a period of extreme pressure, following years of rapid expansion, market shifts, layoffs, and recapitalization. Drawing on his background in restructuring and finance, he shares what it takes to stabilize a business when momentum disappears, why transparency becomes essential in crisis, and how focus and execution replace optimism as leadership priorities.
The conversation examines the difference between growth and durability, the hidden risks of moving too fast, and why rebuilding trust with employees, investors, and customers requires patience, clarity, and disciplined decision-making.
This episode offers a candid look at leadership when speed stops being an advantage - and discipline becomes the only way forward.
About the Show
The Iteration Lab explores how leaders are shaped by their history, their heroes, their heartbreaks, and their hopes.
Hosted by Mike Corbett, each episode features candid conversations with business and technology leaders navigating complexity, change, and high-stakes decisions.
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Learn more about Jarvis Consulting Group: https://www.jrvs.ca/
Watch full episodes and short-form content on YouTube: https://www.youtube.com/@jarvisconsultinggroup
Decisions around personnel and decisions around retracting from markets that you had recently expanded to. I think those are very, very challenging things to do.
SPEAKER_02Imagine being the new CEO of a company that broke the mold, pioneered a new funding model, created a new category, redefined how e-com founders can scale more effectively. A rare Canadian unicorn valued at$2 billion. It was a rocket ship and hypergrowth. But the week you took it over felt more like Apollo 13, a mission that almost didn't make it home. Headlines of 30% layoffs, challenges that most companies don't survive. That's exactly where our guest found himself. Please welcome to the Iteration Lab, Andrew Curtis.
SPEAKER_04Thank you. Awesome to be here. Thanks for having me.
SPEAKER_02Maybe before we dive in, we could just do a quick snapshot of what is Clearco, what makes you different, and why should Founders care? Sure.
SPEAKER_04So Clearco is a working capital provider to plain English in plain English. So we serve direct to consumer e-com businesses that need financing. And typically they need financing for working capital. So when they're buying inventory or they want to pay for marketing or logistics and fulfillment, they need to find ways to fund or finance those activities. And Clerico provides capital directly to those e-comms in order to do that. So these e-coms are D2C, so they're selling directly to consumers. They have online operations, that's how they sell their products. Sometimes they may sell through stores as well. But all of our customers have some element of DTC business.
SPEAKER_02I love that. I mean, I'm a little biased because I'm a D2C e-com founder, free revenue, but the second I get a large purchase order, I'm knocking on your door, Andrew.
SPEAKER_04Please, please, that's what we're here for.
SPEAKER_02Okay, let's pick up where we left off. So before you started as CEO, you were consulting for Clearco.
SPEAKER_04Correct.
SPEAKER_02So you knew what was happening behind the scenes. I feel like most people would run away from the storm, but you just ran towards it. I'm curious. What made you lean in and what did those first days, months look like during the transition?
SPEAKER_04Yep. So just by way of background, I was introduced to Clearco by one of the company's large U.S. venture backers, um, a partner at one of those um VC firms knew my background, and I have a background in restructuring, financial restructurings, and also some structured finance. So it was a good, it was a good fit with Clearco at that time. What made me lean in was kind of the the complexity of the situation and also I like tough puzzles and I like emergencies, and so all of that was really attractive to me. I mean, when I first came to Toronto, I knew very little about the company. Um, I had met the founders just over a call. Um, I had spent a little bit of time with the with the US VC firm. So when I was coming to Toronto, I really didn't know what I was getting into. Um, but once I got here, I made sense of the situation quickly. It was like situations I'd been in before. It felt very familiar to me just based on what I've done over the course of my career.
SPEAKER_02Was it difficult being a first-time CEO as you navigated the transition and the rebound?
SPEAKER_04Yeah, so I was an advisor from mid-July of 22 through around uh Halloween of 22, and then I went back home to the States, and then the board um contacted me around Christmas of 22 and asked me if I would consider becoming CEO. And, you know, the first time they asked me, I thought they were crazy. Um I thought it was a like a very novel idea, but it was a very exciting opportunity for me, and I will always admit and tell anyone who listened to me that I am indeed a first-time CEO, and there are lots of things that I've had to learn on the job, and there's still a ton of things I'm learning every day, but it's an extraordinarily dynamic and exciting job.
SPEAKER_02I think what's a testament is I was researching you before uh we did this podcast, and the reviews from when you joined till now has drastically improved, which I think is a testament to your team and your customers. Um, just really appreciating your leadership. So you talk about Clear Co 1.0 and 2.0. Can you walk me through that journey?
SPEAKER_04Sure.
SPEAKER_02Yeah?
SPEAKER_04Yeah. So um 1.0 we call them the go-go days. And so what the founders built in 1.0 was uh uh a brand new category, which was revenue-based finance. That's what we call our working capital product, it's revenue-based finance for DTC e-comms. So they did something which I think is really special, which is they created a category out of whole cloth, and they were trying to solve the DTC e-com founders' need for financing. And so the challenge back then, before we created a category, was if you were starting a DTC e-com and you needed funding, you really had very limited options. You couldn't go to your bank, you couldn't access traditional bank lines of credit, and so you were relying on equity. And so you were constantly diluting your ownership to raise capital to grow your business. So, what the what the founders figured out, what ClearCoast founders figured out was okay, there is this product called revenue-based finance, which exists in the offline world. And so what if we applied it to the online world? And in doing that, um, it seems so simple in retrospect, but it was revolutionary at the time. They created this extraordinary new category and they helped so many entrepreneurs, founders, operators build businesses with our capital that would have been tough to do otherwise.
SPEAKER_02So, where did it start turning upside down?
SPEAKER_04So the the the founders struck this um this cord with this great idea.
SPEAKER_03Fabulously.
SPEAKER_04And and then they grew very rapidly. Um, and the founders were very good at growing the business, and they were also very good at raising capital. Um, and back in those days, we'll call them the go-go days. Oh, VCs uh were rewarding, rewarding businesses and founders that could show or promise uh high growth, right? Rocket ship growth, whatever you want to call it. And that was a period in time. That was a specific market, and that's what VCs and other investors wanted um at that period of time. So they grew, grew, grew, and they were doing a lot of different things. Uh and so some of the like it became kind of sprawling, I think, the number of initiatives they were pursuing. And they were the founders were very creative and highly entrepreneurial. And so there were lots of different things they wanted to do, and the company grew bigger and bigger and bigger, and they were raising capital all the time. Um, but at the same time, markets began to turn. Um, and when markets turn, Clearco experienced some challenges. Um, we, when we give someone capital, we rely on our own financing uh providers. So if I give you$100 of capital for your new DTC e-com, it's really not$100 of Clearco's capital. It's some of our capital and then some capital that's being provided by a funding counterparty of ours. And so we had some, we experienced some challenges with those facilities. We call them asset-based uh financings. We had some challenges with those facilities in in summer of 22, and that was around the time when the economy was beginning to weaken a bit, uh rates were increasing. Um, so it was a different macroeconomic environment at that time, and that's when the go-go days began to recede.
SPEAKER_02So when you think about 1.0 go-go days, 2.0, I guess restructuring, stabilizing, focus. What carried through or carried over from 1.0 to 2.0? What did you improve? What did you iterate on? What was brand new?
SPEAKER_04Yep.
SPEAKER_02Did anything survive?
SPEAKER_04So I think the the thing that carried over overwhelmingly is the brand. Um the founders built something very special that they invested in. Um and that was something that's very hard to duplicate. So the brand clearly today is it remains uh one of our chief assets. The other thing that carried through was just the resilience and the talent of the workforce. They're clearco is not as big as it used to be, so we have fewer employees, but that employee core is marked by a lot of people who care very much about the mission of Clearco, which is serving these DTC e-com founders and operators. Um, and they're smart and they're talented and they're hardworking. And they also, you know, the people that are still at Clearco today that were there during the 1.0 days, they have been kind of like through the roller coaster ride, and they're extremely kind of durable and resilient. Um, so I think those are the like the two most important things. And also like a sense of like a sense of can-do and a sense of ingenuity um that you know s supports everything that Cleargo does today.
SPEAKER_02I love that. I want to touch back on the employees and the upscaling and the downscaling, but in terms of the product suite that you have, because uh there's been announcements, you have some exciting new products going on. Um, how do they differ from what was previously uh offered and what is the the benefit?
SPEAKER_04We recapitalized the company in October of 2023. When we came out of that, we were very, very, very focused, right? So we had a single product in a single geography, and and the the product that we had then was something called invoice funding. And so the way that product worked was you would come to us, we would underwrite you, we would tell you based on a financial analysis, well, we can give you X dollars of capital. And then you would consume that capital by uploading invoices, invoices for inventory, invoices to uh for Google and meta advertising, whatever the case may be. And then we would pay that invoice directly on your behalf. Today we have that product, but we also have um, as of a month ago, uh we've gone back to a cash advanced product, which is something we had in the 1.0 days, which means I underwrite you, um, I tell you what your capacity is, and then instead of you uploading an invoice, I just give you the cash and you deploy it your on your um on your own, and you you determine the best way to use that capital rather than paying an invoice. So we we think of those two products as kind of side by side. Some people want the cash and they want to deploy the capital how they best see fit, or others want us to pay invoices directly on their behalf. The biggest change that we've made over the last three months or so is we've in we've we've created a product and we've had it in in kind of testing since early part of this year. It's called rolling funding capacity. And so rolling rolling to do. Um you can think of it as a revolving credit facility. Our product is not technically a credit product, but you can think of it as a traditional revolving bank line. So rolling funding capacity. I come, you come to me, uh Clerco tells you, like, okay, you're we'll give you a million dollars of this capacity. And then what you can do is you can fund it, you can pay back, and then you can fund again. So if it's a million dollars and you pay, you draw the full million and then you pay back a hundred thousand, well, then you can redraw a hundred thousand. So the most important thing about that is it gives our founders and operators a lot of visibility and predictability into their capital. And so that is what we find that every DTC e-com founder and operator wants is they want visibility and they want to know, okay, I'm growing very rapidly. I need to know the working capital is available when I need it. So if it's August and they're looking into Black Friday, Cyber Monday, they're making a lot of inventory purchases. They may be ramping uh Google and Meta campaigns. And so they want to know that, okay, when it comes time in September, October, November, I want to know that I have that rolling funding capacity and that I can rely on it and then the Clearco is going to be a reliable and steady partner. Because I think that the biggest challenge with funding DTC e-comms is they cannot access traditional bank lines, right? So you can't go to your local bank and say, I run a DTC e comm, give me a million dollars. It's it's going to be tough unless you have a lot of operating history and the bank also understands your business. So revenue-based finance has to really meet the founder's needs for visibility and predictability. And so our rolling funding capacity product is is intentionally built to do that, right? What we hear again and again and again from customers is they want to know, where will you be in three months with us? Where will you be in six months with us? Will you be a reliable funding partner? Because sometimes I need to move very quickly, right? I I see I need to make an inventory buy very quickly. Um, we have a customer who, uh, if you can believe it, he remanufactures um transmissions. Oh. Right. And he actually sells them online and delivers them. Uh, but he contacted us recently and he said, Well, I like a large um group of transmissions came up and I want to buy them and rebuild them. And so he came to us and we funded him within 48 hours. That's amazing. And so he was flying to Detroit, and he's like, When I get there, I'm gonna look at them and then I'm gonna need to fund it quickly. And so then we step in and we help him fund it. And he knows because we have a we have this product, uh, he knows like I can rely on Clerico to be there when I need them.
SPEAKER_02See, I love that because I feel for econ businesses, growth is not like a straight line. It ebbs and flows, it's unpredictable. There's times you need a lot of money or capital. Um, so I I love that you meet founders where they need to be.
SPEAKER_04Yeah, I think I think it's like I think people who think that these businesses like are linear or they grow in a linear fashion are kidding themselves or they're just not paying attention because masks during COVID. Yeah, you see like you see massive expansion, then you might see a little bit of contraction or or a modest modest growth and then massive expansion again. And so what you need in a capital partner is someone who can constantly be there for you and be like, what do you need today? And I will provide that to you. And so we don't always get it right for sure, right? But that is our goal. And that's like when I was talking about the the employees and what carried over from 1.0 to 2.0, a lot of our employees are highly motivated by the idea of serving these founders. They play an extraordinarily important role in our economy, and so and we want to help them grow. And so the best way you can help them grow, and by the way, the best way Clearco can grow itself is figure out the products that satisfy their needs, tailor them, build them, and then provide them to them. And that's what we've been doing post-recapitalization when we really had a fairly narrow product suite. So we're we're expanding and building the product suite all in an effort not only to help Clearco grow, but more importantly, to help support our founders.
SPEAKER_02I love that. I think going back and touching on employees. So you went from about 600 employees, scaled down to 100. What did you learn from that period and how do you approach your strategy when it comes to hiring as you rebuild? Do you have any priorities?
SPEAKER_04Um, those are all great questions. So the the contraction is always challenging. Um and and like we discussed earlier, 1.0 grew like a weed. Um, and then we got smaller. So what I've noticed since the recapitalization is like the hundred employees we have today is not the hundred employees we had around the time of the recapitalization. There are always people coming and going, and you're constantly trying to infuse the company with new talent. Um, I think the best, the best uh outcomes we've had is when we've hired seasoned leaders, people who actually have run functions that we need uh we need run well at Clerico. And you hire them, you bring them in, and you just let them do their thing, right? That's the most, and that's the that's one of the biggest learnings from me as CEO is I I tend to be high touch and I like to understand everything that's going on in the business, but you need you need leaders that you can really lean on. And so what we've been doing um post-recapitalization is always searching for really talented um function leaders uh and people who are very good at specific disciplines. You bring them in and you introduce them to the company and then you get out of their way.
SPEAKER_02Do you feel that now that you're growing? Um and I love it because I feel you got leaner, more focused. And as you think about your go-to-market, is there a higher focus on client success uh staff versus just sales staff? Or what is your approach?
SPEAKER_04Well, I think the the biggest um the biggest and most persistent challenge for us is what we call net new, uh, which are first-time customers, or re-engaging customers that maybe had once been clerical customers but no longer are. We have a very, very good retention rate. So what that tells you is when we find customers, they stay with us. And they stay with us because I presume they love the product, they love the company, they love it's because of Mr.
SPEAKER_02Curtin.
SPEAKER_04Yeah, exactly. Whatever it is, I don't care. But they stay with us. And so our retention rate is quite high. But we're always trying to find new customers to add to that customer success and retention pool. And so, like if you really drill down into, you know, we we describe it sometimes as the originations puzzle. When we put out capital, we call that an origination. So the originations puzzle is really a net new or first-time customer puzzle. And we're always focused on how do we build more top of funnel? How do we uh how do we expand our pipeline so that we can we can find customers that we haven't interacted with before, that we haven't served, and we can bring them all the way down the funnel, get them funded, and then hand them off to customer success, and they remain customers of ours. And if you think about the landscape, the DTC e-com landscape, there are always customers that you have that are getting bigger and bigger and bigger. And maybe they outbrow you at some point, right? You want to see them at some point kind of spread their wings and leave the nest. And at that point, they're accessing a traditional bank facility. Maybe, you know, they start in year one by year six, uh, they've been through revenue-based finance with Clearco, and then they're going to Wells Fargo. So you have customers who are constantly getting bigger, growing faster, and then maybe they're leaving the nest. And then you've got to find a new generation of nascent DTC e comms that are finding their footing, they're finding product market fit, then they need working capital, and then they need to grow. So we think of it as this cycle where you're you constantly have to look for and be successful in identifying the best new brands, right?
SPEAKER_02I feel it's great that you collect so much data that hopefully that'll help create the okay. I want to take it a little back because I feel that the uh and thank you so much, Andrew, that the rebuilding, the transition was complex. There was a lot of probably difficult times a week race over. So I was wondering if you would peel back the curtain a little bit and give us an example of maybe a difficult decision that you had to make that most people in the public may not be aware of.
SPEAKER_04One of the biggest challenges I faced during that time was kind of trying to keep everyone engaged and and let them know like we're on our path, like we are on our way to revitalizing the company, but I need time. And I just kept asking them for time and they were gracious enough to give it to me.
SPEAKER_02So I feel that's how you kind of kept that company morale up or the core team together.
SPEAKER_04Yeah, I think the biggest thing, the biggest lesson for me during that period of time was the value of transparency. Um, because I think in in 1.0 days, it was just a rocket ship. And so it was easy to walk around and and just be upbeat and positive, and you're like, I'm part of Clearco and this great Canadian unicorn, and we raise capital like that, and we do it at ever-increasing valuations. 2022, 2023, it was a different story. So when I became CEO, what I tried to do day in and day out was just to be incredibly transparent. And I think that like that culture of transparency is what helped us keep everyone together doing during a very choppy, uncertain time. Just like tell, be very direct and very honest with your employees.
SPEAKER_02I feel like if you're transparent, then you build trust and then they feel included and part of the team.
SPEAKER_03Yes. So I love that.
SPEAKER_02Again, back to the the reviews. They they were really positive. Um going back to Michelle Romano and Andrew D'Souza.
SPEAKER_01Yes.
SPEAKER_02Especially considering uh Michelle has a little bit of celebrity to her little dragon den fame. Um bold visionaries, uh, wrist shakers, big ambitions. How have they influenced uh or complemented the kind of the way you lead since you stepped up to EC?
SPEAKER_04Yeah, so that's a that's a great question, and I think about it all the time. And if I'd love to have them here and they could tell us what they But I think like the one thing I take away from them, and I take it away from our customers every day, is they see possibility, right? They the world is full of possibility. And so what I always try to take away from them, and what I always like I always admire in our own customers, because they're really not that different, right? They're they're founders and operators. Um, what I always admire is like they are optimistic and they see the possibility in everything. And that's what you need to do to be an entrepreneur. And like sometimes you're like you're saying yes when everyone else is saying no. Sometimes you see a founder and you're like, God, are they delusional? But that's what makes incredible things possible. And that's what makes it able, what makes them able to build a new category and a company like Clearco that has extraordinary brand awareness today. So to me, that's the number one lesson from from Andrew and Michelle is they see possibility in things. And I see that as they go forward and they do different things post-Clearco.
SPEAKER_02I feel like even you stepping in as CEO, um, coming from a different background, fresh eyes, you would probably also see things a little differently. And maybe that's why it's been, I guess, so innovative and also very efficient.
SPEAKER_04So I think my like the way the way I think about my own background is it's very different from their background. And and uh, if I'm being really uh honest and candid, I don't always see the possibility in everything. I I spent the bulk of my career in leveraged credit markets, which means LBO debt, and I spent a lot of time in and around financial restructurings, which means companies that are reorganizing, sometimes they're failing. And so um what I have is like a very kind of cold, steely-eyed view of things. Um, and sometimes I have to remind myself like see the like see the possible in every situation and be optimistic and and uh don't beat up on yourself for like you know not being able to do everything exactly right, but you know, like celebrate, celebrate things that you are doing well and uh kind of inculcate the sense of optimism and possibility in your employees.
SPEAKER_02I feel like that's a beautiful yin-yang because you like to rein them in and as they as they uh expand. Uh looking back, is there a piece of advice that you'd give your past self stepping into this or any other listener that's going through uh fork in the road, tough rebuild or restructuring?
SPEAKER_04Yeah, so I I think I have a couple of ideas there. Number one is um just keep going. Uh a value that we celebrate in addition to transparency and all of our communications uh with employees is be resilient, right? Walk through walls, get get used to learning how to walk through walls because on the other side of that wall is is something great. But you have to be tough and uh in hard times, um, demand resilience. And so I like that's something we've talked about at Clearco since day one. Um the employees exhibited it, the founders when you know things were great and then they got choppy. Uh founders exhibit it. So to me, that's like top of the list.
SPEAKER_02I love that. As you kind of move from 2.0, what does the headline for 3.0 look like?
SPEAKER_04God knows. No, I'm just trying to no 3.0 is about um what I'd love to do over time is is just expand into new products and markets. Um, so we have been exclusively focused on DTC e com. It would be great to begin to penetrate the offline world. Uh revenue-based finance, um, it is a product that started in the offline world. Um it's it's not called revenue-based finance in the offline world, but countless small businesses rely on that product to fund their working capital needs. And I think if if you could aim our underwriting engine and our risk and credit and underwriting engine at the offline world, it could be really a powerful thing. Um, so I really am excited about that. And then I just think there are additional products to add. Um, we've added this rolling funding capacity, which functions somewhat like a revolving credit facility. There are term loans. I'd love to add a term loan, which is fairly different from a revenue-based finance uh product. So there's a there's an incredible world of possibility and expansion opportunities. But what we have really been focused on since day one post-recapitalization is just do what we are focused on doing today, do it right, and prove it out and prove that it actually works, and then you can you know begin to layer on these other markets.
SPEAKER_02Scale responsibly. Correct.
SPEAKER_04Scale responsibly.
SPEAKER_02I love it.
SPEAKER_04That's the the new mantra I mean.
SPEAKER_02Um let's pivot like you did, and I want to turn the spotlight on you. Okay. I feel you have a very impressive resume. 20 years, New York Finance, Wall Street, working for firms like uh Merrill Lynch, Lazard, advising major players like Annalie Capital, also incredible education pedigree.
SPEAKER_03Thanks.
SPEAKER_02Tufts, Chicago Booth, um Brown, I mean League.
SPEAKER_03Yeah, great.
SPEAKER_02So but who is the person behind that resume? Andrew, if you were to describe yourself to me without using any labels or titles, what would you say?
SPEAKER_04Um Well, I'm the son of two educators. That's how I always think of myself first. My father was a uh professor of cell biology, um, and my mom was a a school teacher. She taught English. And I I really attribute like everything that I've done and my values and and a lot of my skills to growing up in that household. I was the last of four children. I have three older sisters. Um, and uh it was uh it was a household that was filled with a lot of love and a lot of support, but a lot of expectations too. Um and so I I think what I learned growing up is kind of what carries me through day to day.
SPEAKER_02Would you feel that in your household? Because everyone sounds pretty amazing, success was expected?
SPEAKER_04Um, I don't know if success was expected, but hard work uh and perseverance was expected. And um my parents really expected us to make the most of our God-given talents. And that's something that like I I have four children, and that's what I always tell them is you're everyone comes to this world differently. Uh God gives us all different talents and abilities, but your job um and my expectation, and my parents' expectation of me is you're gonna make the most of what you're given. And you're gonna work hard, you're gonna try to develop whatever talents you have, and you're gonna do it for you know the benefit of yourself, your family, and the people around you.
SPEAKER_02I think that's amazing. For kids, I feel you are crushing it in every aspect of your life.
SPEAKER_04Busy, that's all I can tell you.
SPEAKER_02As a parent, has that changed how you lead at work? And what do you hope that your kids take away from watching you?
SPEAKER_04Yeah, so one it's it's funny. Um, as a first-time CEO, I as time has passed, I see more parallels between the leadership that I am required to uh exhibit at work and and the some of the leadership I have to exhibit at home. And I think the number one thing I would say is I've learned the value of not always being a hammer. So I think that's so I I'm trying to lead uh at home and and I work by um you know encouraging people and and uh supporting them and empathizing with them in order to like get them to do the things they need to do and in order to like realize their own potential. So um for years, I think, especially when I was raising my kids, I was a bit of a hammer. I'm trying to do less of that now.
SPEAKER_02Well, you know what? I feel like if we're tough with them in the beginning, you don't need to as they get older. I hope so. Right.
SPEAKER_03That was my that was my plan. So we'll I'll let you know how it ends.
SPEAKER_02Um what was little Andrew like as we talk about kids? And is there any part of that kid that still lives in you today and parts of him that you had to leave behind?
SPEAKER_04Um so I would say the little Andrew was uh he was sometimes careless. He was a kid, right? Um he's less disciplined than than I am. Uh he had a lot of fun as a kid. Um, some things came easily to him. Uh, and then as he grew up, like some things came harder to him. I had a I had a very happy childhood. Um, loved the family I grew up in. I had three sisters that took good care of me, parents that took good care of me. Uh I had lots of fun in the neighborhood I grew up in. It was just a you know, that was back in the old days when you didn't have helicopter parents and you kind of got to run wild.
SPEAKER_02Just like stayed out until the something.
SPEAKER_04My parents would ring a cowbell uh at dinner time. I love it. And I would we had a bunch of woods behind my house, and we'd be in the woods doing God knows what. You'd hear the bell ring and then you'd come home. So the it was like a very, very happy time. Um, I think you know, everyone everyone leaves their childhood behind. You try to retain like that youthful spirit.
SPEAKER_03Right, right.
SPEAKER_04Um, and uh like that mischievousness, and and I think I still have that, but you know, adulthood is more serious, especially if you have four kids.
SPEAKER_02Well, what did you want to be when you grew up when you were what did I want to be?
SPEAKER_04So when I was when I was in high school in college, I was really interested in writing and literature.
SPEAKER_02Oh, that's my next question. Like segue.
SPEAKER_04Yeah, so I was um I really enjoyed writing. I studied English and American literature uh in college. Um it was something that like I felt I was good at that came naturally to me. And when I first uh when I first left university, I worked at a children's book publisher um as an intern the summer after I graduated, which is kind of crazy in retrospect. Um and then I worked for uh magazine, um, Inc. magazine, INC Period, which is based in Boston, and it's a it's a it's kind of funny when I think back to it now because it's a it's a magazine focused on small, rapidly growing businesses. And here I am decades later, uh working for a company that serves rapidly growing small businesses. So um that was where my interest was at the time. Uh but then that kind of m changed. Um, and then I ended up going to graduate school, and then I went to New York and and worked in finance for a long time.
SPEAKER_02I feel like beyond the foreshadowing of Inc. magazine, night and day, publishing to finance and then to Clearco, what did that winding path look like? And how did you how did you s graze over it?
SPEAKER_04It's a great, it's a great question. I think um there are a bunch of things uh that I think about when I think about that that transition or that shift in interest. Um one is simply I like had a view of what the world of finance would be like, and I thought it would be exacting and demanding, and I didn't find publishing to be that often. Um I also felt like that world would be very meritocratic, right? And so you would be rewarded for a lot of hard work and talent. Um, and I wasn't sure I always saw that in you know the limited publishing experiences I had. And I also think like I was probably victim to like a very romantic idea of working and yeah, exactly. I probably had like completely uninformed, uh, romantic uh views of what it would be like, and then you get there and you're working as an investment banking associate and you're working a hundred hours a week, and it feels a lot less romantic at that point. But it was a lot of hard work, and there it's an extraordinary training ground, I would say. And that's the one thing I really appreciate about those days is that it was a very exacting environment. People had very high expectations of you. You learned a lot in a very short period of time, and what you learn then serves you uh for years and serves you in over the course of your career.
SPEAKER_02Well, I feel like you were there in like the good old days. Like when people think of Wall Street, you've living the dream, living the dream. And so now that you've been in New York finance, pivoted to Toronto uh fintech, what is one thing that you loved about the other that you would pick and smush together?
SPEAKER_04If I could.
SPEAKER_02Yeah, if you could.
SPEAKER_04So the the the one thing I would say about working in finance in New York is that people are um they're very narrowly focused, but in a good way, right? And so sometimes um people criticize uh New York City uh or Wall Street workers as being uh overly focused on making money, but it does create a clarity of purpose. Um and the the the that world to me is very efficient, very, very efficient. And the people that work in that world, at least in the jobs I had or the sectors I was in, they're very hardworking and they're generally very bright. Um, and you don't really have to spend a lot of time encouraging them to do one thing or the other, they just show up goal-oriented, yeah. Very goal-oriented in this like clarity of purpose or clarity of vision. Um, but at the same time, it's a very narrow world. Um, if you are like if you're a bond trader, you come in every morning at 7, 7:30, you trade bonds bonds all day, you go home. And so some people love that, and they'll like they'll trade bonds or institutional term loans or equities from the time they're 22 to the time they're 55, and that's fine. Like they love it. But it's like I I never found or I found that sometimes like stolifying or very narrow to me. And so uh what I see in Clerico is just like a much broader uh field of vision, and the people are like they're different, right? There there's there's more heterogeneity in the employee core. In in New York City, you know, you work with a guy who went to Warden, and he's a smart guy and he's very motivated to make money. Uh, but there's like there's a lot of homogeneity um on the street.
SPEAKER_02I think that's a really good point. I didn't even really think of it that way. Um okay. Now that we talked about Clearco and learned a little bit more about Andrew, we have a fork in the road or a segment called Fork in the Road. Okay, so basically it's rapid fire, this or that. Okay. Um questions. Don't overthink it and just go with your gun.
SPEAKER_04It's gonna be hard. It's gonna be hard.
SPEAKER_02Depends on the day, right? Um early bird or night owl.
SPEAKER_04Night owl.
SPEAKER_02Coffee or tea?
SPEAKER_04Uh coffee.
SPEAKER_02Mountains or oceans?
SPEAKER_04Ocean.
SPEAKER_02Is it uh book or podcast?
SPEAKER_04Book. Sorry.
SPEAKER_02Fair enough. Publishing, publishing. Um children's night. I'm kidding. Uh text or phone call?
SPEAKER_04Uh that's a good one. Text.
SPEAKER_02Uh fancy restaurant or food truck.
SPEAKER_04Food truck.
SPEAKER_02Um now let's go back. Want us to touch on hopes, kind of uh looking ahead, your dreams for the future. So when you think of your role today, whether it's your job or the industry, um, what really excites you right now?
SPEAKER_04Um well, what really excites me is continuing the rebuild at Clearco. Uh, I think about you know that summer 22 period and and 23 period as extraordinarily challenging and arduous. And the recapitalization that we were successful in completing was like very tough to do. Very high degree of execution complexity and risk. And like I always say, like nine out of ten times or 19 out of 20 times, you know, that company shouldn't exist, shouldn't have made it.
SPEAKER_02You're a cat, the cat with nine lives.
SPEAKER_04So the the the challenge now is if that's true, then it has to succeed. And the idea of of having gone through that and and all the employees pulling the aura in the same direction to get through that very tough time. Now it puts pressure, I feel like it puts pressure on me and them as well to actually make something of it, right? Because part of the recapitalization depended on some of our investors, a small group, relatively small group of our investors giving us additional capital because they believed that Clearco should survive, that Clearco was something special, that the founders had built this incredible brand, and they gave us capital. And I like I feel a great sense of obligation to them to try to figure this out and to make Clearco a juggernaut and to make it uh cash flow positive and all the good things that every company should be. And so that's what I get most excited about, and that's what I most focus on. And I always joke around and I say to my, like I say to some of my colleagues, I say, if if we can do the recapitalization, which was very tough to get done, and we can't figure out first-time customers, I'm like, it'll kill me. So we will figure it out. Um, we are figuring it out, and we just want to keep growing. And and the other thing that's inseparable from all that is we have customers to serve. And these customers are scrappy, hardworking people who have dreams, who have built products and services that people want, and they're trying to get them into the hands of their own customers, and we really want to be there to support them. Of course, you know, ClearCo is its own business, has to be profitable. Um, but we have this North Star of supporting founders and operators who are doing things that are incredibly tough. So when I think about the resilience that we exhibited through those dark days in 22 and 23, um I think of it as very akin to the resilience and the hard work that all of our founders exhibit. And we I talk to customers every single day. Um, and it's the like one of the favorite parts of my job. And what I see in them is what I saw in Clearco's employees, you know, today as well as a couple of years ago, one foot in front of the other, driving forward, trying to solve complex problems in order to achieve success. And that's what really, really excites me.
SPEAKER_02I feel like that's amazing, especially because you're very high touch. Um, people may not know, but you live in Connecticut.
SPEAKER_04That's clear.
SPEAKER_02Fly to Toronto. I've heard stories of you living out of a suitcase for a month as I was going on.
SPEAKER_04Yeah, it was um it was it was um particularly bad in in 22. Back up. Now it's more sane. But um we we are a company that grew dramatically during COVID. So we we remain kind of a remote first company. So we try to find opportunities to spend time together. We sometimes meet in New York in groups. Um I come to Toronto, we have a lot of Canadian employees, um, a lot of our reps, our uh county executives, um live in the GTA, and then a lot of our engineers and software developers are you know around Toronto, the Waterloo area for obvious reasons. And so uh I love coming up, and it's a great city, of course.
SPEAKER_02I love that. And this podcast, I feel like this will build your SQL MQL base.
SPEAKER_04Yeah, it's awesome. It's a great opportunity. Great opportunity.
SPEAKER_02Awesome. So beyond Clearco, as you think about fintech or even funding, how do you see that evolving over the next uh few years?
SPEAKER_04So I mean it's a great question. I mean, uh I'll say the most obvious thing, which is they're gonna be greater and greater applications for artificial intelligence, um, not only in the obvious uh fields, which is underwriting and risk management, but we see really novel applications of AI in GTM. And so in our sales motion, uh, we're spending a lot of time trying to understand how best to use automation tools like clay um to help us find new customers. And they're extraordinarily powerful tools. They take time to master, um, takes time to learn how to use them and to exploit them or leverage them. But when you get it right, they're quite stunning to me. But it takes time. That's the one thing I would say. And and what we see when we in these tools that we use um in Clearco specifically, possibly the greatest value of the tools is they tell us a lot about when our customers need capital. And so we call them buying signals. Like what buying signals can we discern in all these DTC e comms that we know of? What buying signals can we discern so that we are going to them proactively to give them capital when they need it most? Um, I see that kind of application in countless ways throughout fintech. Um, I think there is um conversely, I think there's a there's this idea that they they can those tools can revolutionize, underwrite. Writing and the way you assess credit risk. And I agree that there are very like there are powerful ways that they can do that. But it may be overstated sometimes, right? Like we've been using machine learning models since the company was founded. They're important, right? But there's also some human uh diligence that goes on when we're trying to assess credit quality. And I think of course the promised land is you have no humans involved in things like financial statement analysis or underwriting, but I think that that's probably unrealistic, at least in the near term.
SPEAKER_02Well, I'm hoping that by the time I'm ready Ant will figure it out in your company. Totally. Um okay. We do something called the next iteration. Okay. This is where the last guest asks uh the next guest a question. Oh no. I know. So before you uh give me a question, this was a question.
SPEAKER_01When you started your career, what was the one piece of advice you wish someone had given you that you think is still true today?
SPEAKER_04One piece of advice. Don't rush. That's what I would say. Don't drive incessantly fast and hard all the time. Take a deep breath every once in a while.
SPEAKER_02Coming from a man that did a crazy research.
SPEAKER_04Exactly. That's the one piece of advice because there's there's a there's a lot of value in pausing, taking a deep breath, assessing, and just driving hard day in and day out, uh, is not always a winning approach.
SPEAKER_02So Andrew, what is your question for the next guest?
SPEAKER_04Okay. My question is what is the one thing above all else that brings you joy?
SPEAKER_02You know, I couldn't agree more. One last question. Iterate or disrupt uh for me, iterate. On bread, on red.
SPEAKER_04That's consistent, yeah, exactly.
SPEAKER_00I don't want I don't want to throw you.
SPEAKER_02Thanks so much for joining us today, Andrew. Really appreciate your time.
SPEAKER_00To our audience, thank you so much for joining us in the iteration lab. If you enjoyed today's conversation, don't forget to like, follow, subscribe, or share content so we can bring you more conversations just like this one. Until next time, keep moving the dialogue.
