00:00:01 – Intro + From Law School to Entrepreneurship
Mike: Hi, I'm Mike Pinkus, co-founder at ConnectCPA and your host at GrowthTales. Today we have an exciting guest - Matt Himel, who's the CEO of Harvest. Harvest is an accounts receivable automation software company that tackles the pain point of collecting overdue invoices. Matt, thank you so much for joining me today.
Matt: Thanks, Mike. Pleasure to be here.
Mike: First of all, I really appreciate you taking the time. We operate in a really similar space, so it's something that's of big interest to me. But before we jump into Harvest, I wanted to ask: what made you want to become an entrepreneur?
Matt: Yeah, it's a great question. I went to business school and one day, it's funny, the admissions person for Western Law came into our business school for a lunch-and-learn. She told us that they were opening up a bunch of spots for undergraduate business students. I was like, that's interesting. Maybe I could go to law school. So I ended up applying to law school and, you know, always much more enjoyed business school.
00:01:05 – The Bar Exam Business
Matt: Law school teaches you a different way of thinking and assessing situations, and I really value my time there. When you graduate law school, unfortunately, what's really waiting for you is law. Nobody told me that, but that's really what's waiting for you.
Matt: I decided I gave it a good go at law school. I might as well kick the tires on a short law career. When we graduated law school, two buddies of mine and I went to write the bar exam. The bar exam in Ontario is these two thick books, open-book exam, multiple choice, and there's absolutely no materials built to practice for it because it's a very high pass rate.
Matt: So we got bored out of our minds studying for it and paid a teacher to draft some questions just so we would have any excuse not to read the materials anymore. Then all of our friends and everyone we knew started emailing us saying, “Could you send us the questions?” He sent us the questions, and so we were like, oh, we're onto something.
Matt: So the next year, we had already written the bar, but we put them online, gatekept them a little bit with some sort of hack, and started selling them. They sold like hotcakes. Thus started my entrepreneurial career outside of my legal practice.
Matt: One thing a lot of people who go into law aren't told is that there's this expectation that it's a great career and it's great financially, but it's very tough. You work a lot of hours, and there are a lot of people who are a little miserable doing so. But my experience was different. I worked at an amazing firm, and one of my biggest takeaways was that the people I worked with actually loved doing what they were doing.
Matt: That helped me dramatically realize that law wasn't for me because they were just so emphatically excited about the law. That reverse signal ended up being really helpful. So I took the experience we had with the bar exam, which we still operate today. It's been around for like 15 years and has been an amazing mini entrepreneurial success story.
00:03:06 – Leaving Law, Reframing, and Joining Tech
Matt: I quit my law firm after about four or five years and applied to a bunch of the satellite offices — the Ubers, the Lyfts. It was 2014 or so, and a bunch of tech companies were opening up, and none of them wanted me. Absolutely none of them. It was very disheartening. They were all like, “Why are we hiring a lawyer? It doesn't make any sense.”
Matt: I really had to reframe who I was and why I thought I could add value.
Mike: After all that time in school.
Matt: Exactly. I got taken in by a company called Tilt, which exited to Airbnb, and there's a great story there. Then once Airbnb acquired Tilt, I got lucky enough to connect with Derek at Drop, and so forth and so forth. So yes, that was my weird path toward entrepreneurship.
Mike: By the way, I think that's a common story. I know a lot of lawyers, and I think it's similar to the accounting space where the vast majority go into industry or firms. But you're right — you graduate and all these law firms are looking for you because there's a shortage of talent, obviously. So that sounds like a great foundation. The fact that you went into entrepreneurship after having that professional background, Matt.
Mike: But what led you to Harvest, and what is the origin story? Because accounts receivable for a lawyer is a different world. How did this all come about?
00:04:34 – Why Harvest Exists
Matt: Lawyers are actually horrible with their accounts receivable, but we'll park that for a different day. They're very good at — well, they're bad at getting their billings in, that's one. You have to bill every hour, and that just... someone needs to fix that holistically. I think they're working on it, but yes, billing every hour sucks. Then billing a client for those hours sucks, and collecting from someone who's continuing to be a client sucks.
Matt: So anyway, it wasn't the genesis of my legal experience that led to Harvest. Really, once I got more senior in my career and got to Drop, and I was a revenue leader, one of the things I hated the most was when finance would reach out to us and say, “Hey, can you help us with some of these overdue invoices that we need to collect?”
Matt: And you'd say, you know what? I manage a sales team. They're out there selling or upselling our existing clients. I manage our client success team. They're putting out fires with our existing clients. It's really not great to go to an account manager or client success manager, or even a salesperson, and say, “Hey, can you get involved in collecting an outstanding invoice?” They really don't want to get involved, and when they do, it derails some of the conversations they're already having that are trying to drive revenue.
Matt: Ultimately, if someone doesn't pay, obviously we have to get involved. So I would go to finance and say, “Hey, show me the breadcrumbs. What have you guys been doing in order to collect this?” There'd be an automated invoice that would go out and maybe an automated follow-up, but they really weren't actively pushing a lot of our clients to pay. Then it would get dramatically late, and so you get to 60 or 90 days and all of a sudden your client isn't really taking your collection efforts seriously.
Matt: Part of Harvest came from those frustrations for sure. Then there's a couple of other pieces. One is I really wanted to build a company in AI. When I was at Drop, we had been around for eight years. Obviously AI wasn't even in the conversation when we started the business, and while you try to weave it through some of your operational efficiencies once you've already developed a company, it wasn't AI-first.
Matt: So I knew when I wanted to start a new business, leaving Drop, that I wanted to be AI-first. And when you look at AI, to me what you really want is something that's data-rich — accounting software already houses basically all the data that you would require for an accounts receivable or invoice automation company — and a repeatable task. Those two things complement AI really well.
Matt: So when I was looking for a business, I knew I wanted to combine those two things. I combined that with my pain point of being a revenue leader, and we got there. There are a number of businesses in the U.S. that are somewhat similar that are sprouting up, and having raised money from Simple Ventures, they have a business model, which is: we want to provide services in Canada to startups, businesses, and SMBs that they just don't get access to because there are a lot of amazing companies in the U.S. that just go to market there.
Matt: So we surveyed the landscape, looked at some of the pain points that I had at Drop, looked at what we thought AI could do, and that's where Harvest was born. The last thing I'll add is when I went to Tilt for the first time, I got introduced to this concept of painkiller and vitamin. You always want to be a painkiller because the vitamin is a slow drip and overall things are better for you over time. But in order to start a business and really grow it and sell it — and I'm still running a lot of founder-led sales at Harvest — you really want to be a painkiller.
Matt: And what's more of a pain than cash flow issues and following up with clients? It's a task that nobody really wants to own, but the outcome is so important to the business that if you don't collect, you start to have to get into working capital loans. You start to have to deal with whether you're going to hit payroll. So that always stuck with me — being a painkiller. And as we started to have conversations with either heads of finance or CEOs, you could see the pain on their face.
Matt: When I know I have a really great customer, they're like, “Matt, you couldn't have come at a better time. We're knee-deep in this right now, and I would love for you to help us solve that.” So Harvest was really the combination of all of those factors into one. I'm really excited to see where the business has come in just a short while.
00:10:11 – Cash Flow, AR Reality, and the Education Gap
Mike: That's a great description. I follow a lot of SaaS business gurus, and I think one of them is Jason Lemkin. I think this was his quote, though I don't know who said it first, but it was something along the lines of: the only way a business can fail is A, the founder gives up, or B, you run out of cash. You're 100% right that cash is at the forefront of literally the minds of every single business. Not P&L, not the balance sheet in particular — just cash flow is that thing you need to survive. It's the oxygen, right?
Matt: One thing you'll really appreciate, Mike, because I'm sure when you chat with founders or people that are coming to you for new business and you ask them to describe their current financial situation, I bet you the vast majority of them are very generous to themselves. But then once you guys get in there, you see, well, they described revenue in this way, but really it's that, or whatever it is. There are always rose-colored glasses.
Matt: We see this all the time. Obviously my clients are great — I'm not giving them a hard time — but what you see is people say, “Yeah, AR is an issue and we'd love for you to help us with this and let's connect. But it's not so bad, and there aren't that many invoices, and the amount outstanding is very manageable.” The ball never lies — or in this case, the API never lies — because when we connect to their invoicing software, and we work with Xero, we work with QuickBooks, you get a very real-time view of where their AR is. It's very frequently much worse than how they stated it when we were doing the sales calls.
Matt: Sometimes people just have a hard time being really honest with themselves about their financial situation, and that's fine. That's what you guys are there to help with. That's what we're there to help with. It's just very interesting, and it creates a challenge for founders when they're not honest with themselves and all of a sudden it comes to a point where they can't make payroll or they run out of cash.
Mike: That's a great point. And I wonder how much of your go-to-market with Harvest is the education piece. Like you said, you come in, you meet a founder or VP Finance or CFO, and they're like, “It's not that big a deal. We've got a few tire kickers. It's not that bad.” But then you display to them and say, “You know what? If you accelerated these five things, that's half a million dollars in the next six months.” And they're like, “Oh, I didn't look at it that way.” How much does education play a role in people understanding the implications to their business?
00:12:20 – Why Harvest Works: Bad Cop, Better Follow-Up, Better Timing
Matt: It's huge. It's a really good point, Mike. There are a couple of things that I'll say on a sales call, and not all of them will necessarily hit. We're still working on which benefit that someone derives from Harvest is the ultimate hitter. But when you hit it, you know you've got the sale.
Matt: I actually posted on LinkedIn yesterday about this one, but I've had a week's worth of onboardings where our clients are actually happiest just having a scapegoat. They're basically paying for an empty AR agent to be the bad cop for them. Just having another layer to their outreach allows the finance person to no longer be the bad guy.
Matt: There's also leverage, right? If finance sends an automated invoice and nobody responds, and then sends another one and nobody responds, and then finance reaches out and says, “Hey, we've sent you this,” and nobody responds, they have nowhere to go. They just keep sending notes, or they have to go to the C-suite or the account manager or whoever it is and say, “Hey, we sent this, then I jumped in. There's nowhere to go.”
Matt: So what ends up happening is you create a new layer to that outreach, which is like your accounts receivable person without actually having to hire anyone and do benefits and worry about vacation and the whole nine. We have Pat, we have Luca, we have Ruth — people-like names — but you add someone, and all of a sudden you have another layer. So automated can go out, Ruth can reach out, and then finance can come on top and say, “My colleague Ruth has sent like eight follow-ups. What's going on over there? Do you guys need a little more time? I know it's a tricky part of the year — let us know.” And now finance gets to be the good cop, the partner to the partner, without always having to reach out to the C-suite or the account manager.
Matt: This week, unanimously, that was hitting before all the other amazing aspects of Harvest, like reducing DSO — just getting paid faster — saving resources, because 80 to 85% of the emails we send can be automated. There's no reason somebody needs to get involved. The vast majority of emails are: here's your invoice, following up on your invoice, taking payment. Anything strategic or disputed can totally be handled by someone on the team, but they don't need to be handling the first 80%. They should just be focused on the last 20%.
Matt: And most importantly, it's just not a great task. Very rarely do I come across someone who's like, “You know what I love? Coming in on a Monday, pulling the AR report, and figuring out where I am as far as emailing and communicating with people who owe us money.” So there are different ways of proving to people that Harvest is effective from a financial perspective, but sometimes it's just that completely qualitative benefit of being able to sleep at night, knowing somebody's doing your outreach for you and having someone you can point to as the bad cop.
Mike: I think a point you made there is that you can almost set it and forget it — meaning let the technology be dynamic for you. People are not disciplined, so I think your point is valid. How often are people actually following up on receivables? It's one thing to say, yes, a human in the loop can go and call or email or whatever it might be, but how often is that actually happening?
Matt: Look, as a human, we make decisions based on how we feel. You don't want to send a follow-up on a Friday afternoon. It feels like not the right time. Even if the person gets it, they ignore it. Then what do you do Monday morning if you feel like they ignored you and aren't paying the invoice that you sent out? Do you send it Monday morning when you know they're probably pretty busy? Should I wait? And so you have all this human emotion put into it.
Matt: We have the reverse, which is that we're democratizing best practices. Our system is learning as it goes and knows the best time to send an email. It knows the best subject line to use in reminder emails. It knows the best buttons to push when they need to be pushed. Here's a really interesting one: sometimes it makes sense to actually send an email on Monday instead of a cadence of every three days, which some workflows use. Sometimes it makes sense to go Monday and then send another one Tuesday — just boom, boom.
Matt: Who in their right mind would do that? And even if you do that, are you really going to do it strategically across all of your accounts? But sometimes that works really well. Like: “Hey, you owe on this invoice,” and then the next day, “Hey, I'm just following up on a bunch of overdue invoices. You're still on the list.” Boom. It's tactical, and much better than asking an individual to do it, even if they have some best practices that work for them themselves. It's been really cool to see our system continue to learn and figure out the best ways of driving collections on behalf of our clients.
00:18:40 – Simple Ventures, Building in Canada, and Hiring the Right CTO
Mike: You mentioned being part of Simple Ventures. Obviously, there’s a big push for innovation in Canada with all the things going on in the world with tariffs, et cetera, but also just being part of a really big success story in Canada. How do you think that alliance is going to help on the AI development and being a technology-first company, being connected to Simple Ventures as part of that journey for Harvest?
Matt: I can't say enough amazing things about Simple. Obviously, with Mike Hachin's leadership, he's created an amazing organization. Rachel Zimmer, who's the CEO, is also amazing, and she's put together an incredible team.
Matt: What they've built is a network of LPs, which is by far the greatest network of Canadian LPs I've ever seen. What you get there is not only some really great people who can help them make investment decisions — because they pull them in. When I went to investment committee, it wasn't just Rachel and Mike. It was actually a group of 10 or 12 LPs who had subject matter expertise and were quite tricky to pitch to because all of a sudden they're just random people from the Canadian tech ecosystem who have been very successful in my space asking me questions about things, and I'm like two or three months into an idea that I feel really strongly about.
Matt: Then you get that on the back end. Once we've raised around, I pulled one of those LPs into the board. So Kirk Simpson, who started Wave Accounting and had a big exit to H&R Block, is on my board, and he's just been incredible.
Matt: There's no shortage of people that I can message Rachel about, or she brings to me, and says, “Hey, we have this network. There are people that are really excited to get involved. Who would you like to chat with? Who do you think will be valuable?” Then they wrap the business in a bunch of support systems that make my job so much easier. Because there's building a business, and then there's building a company, and those two things are completely different.
Matt: Having someone who says, “You focus on the business and we'll give you all these assets you can use for the formation of the company — legal, benefits, ConnectCPA on the accounting side” — I just wrap myself in some things that Simple Ventures has already preordained, and we're off to the races. That's why I feel so good about where we are only a couple months post-fundraise.
Matt: On the tech side, their first two portfolio companies are actually not that technically enabled. They're amazing companies, but we're really the first AI-forward company. So we really needed to find a CTO early, and we went back out to Rachel's and Simple Ventures' network.
Matt: Hiring a CTO these days is really interesting because there's obviously this “vibe coder” stream over here, and then there's this senior engineer stream over here, and in the middle there's a bit of tension. One side says you can't just vibe-code your way to a product, and the other side says you don't need to build for 20 years. We really wanted to find someone who, from the senior side, understands rate limits and tech debt and the things that are important to building a company, but also from the other side embraces new technologies and can build really quickly and ship new product features quickly. We got so lucky to find my CTO, Poria.
Mike: Coming from being a lawyer and having worked in scaled-out tech companies already, you obviously have the prerequisites to understand technology. But did your past experience allow you to make that decision of when to leverage AI to speed up development versus when you still need architecture, security, and all those things? Was your experience at Drop what allowed you to figure out that balance in a CTO, or who to hire?
Matt: I think when you're non-technical and you're hiring a technical resource, you have to rely on other people to vet their technical skills. So again, I leveraged a couple of people through my relationship with Simple. There were a couple of LPs who have technical development firms and other things who put Poria through a bit of a wringer and said, “He's awesome. He's technically sound.”
Matt: Then with Poria's blessing, I called some of his previous non-technical coworkers and just said, “Hey, what's it like to work with Poria?” Because that's what's important to me. Once you have a baseline of, yes, this person is amazing technically, then on the other side it's: how do I work with technical resources? How much handholding do they want? How much support do they need? Do they need to connect frequently or do they just go off and build? Do they like to be micromanaged?
Matt: For some reason, Poria and I have been extremely harmonious from day one. Most of the questions I had around working with a new CTO were really around work style and where my work style might not jive well with his. That's super important, especially because right now it's just the two of us on a daily basis.
Matt: Working at a bunch of tech companies, you start to learn how to work with different technical leads. I had the pleasure of working with Darren Fung at Drop. He's an incredible CTO and engineer. You learn what's the best way of not solutioning for them, because who am I to tell them how to build something or how to approach something?
Matt: Early days, you're like, “Hey, I have this revenue opportunity — build this.” Then your client comes in and says, “Yeah, this is kind of what I asked for, but you didn't think about these eight things.” It looks like what I asked for, but it doesn't do what I was hoping it would do. As you mature and you start working with better technical leads, you realize you're like, “Look, our client wants to do this. I leave it to you to figure out the best way to build that product, and build it so it can help more than just this one client who's asking for it.”
Matt: So Poria and I have been really great at saying, okay, our client's giving us this feedback — how do you think we should approach it? Let's ask them some questions. One thing that's really important to me is that all of our clients now have a Slack channel with us. They give us real-time updates, they make product requests. This morning I just said, “Hey, how's this feature going?” and they said, “We're loving it. It's great.” It's really important to me to get real-time feedback, and just jamming ideas at someone and saying “build this, do this” is never going to lead to a successful partnership.
00:29:09 – Product Challenges + What Harvest Builds Better
Mike: You've got the CTO now, you've got funding figured out, and you're solving a mission-critical problem. Intuit and Xero are multi-billion-dollar publicly traded companies, and they have millions and millions of users that probably suffer from this problem. So it seems like you have a lot of the right ingredients. Matt, what have been the challenge or challenges in getting Harvest going and figuring out what to build just in general for that user base?
Matt: It's a very good question. When we first started to ideate for Harvest, I reached out to a whole bunch of friendlies and said, “Hey, would you subscribe to a platform that helped you collect your overdue invoices?” And everyone was like, “Sure, why not?” Then they would give me their hardest collections and basically be like, “Here's 10. Haven't heard from those clients in three years. Have at it.”
Matt: You're like, oh, this is so great. Everyone's willing to give you work to do, and they're willing to pay you. What a great idea for a business. But before the platform, it was just me, and I can do anything. I can call, I can do research, I can text, I can do anything. I could show up to someone's business and say, “Hey, you owe one of my other clients some money. Can we get this sorted out? Do they have the wrong phone number? What's going on?” So your first proof point is: okay, people are interested in this, and there is a way to ultimately collect the money, and therefore there's a business model.
Matt: Then you fast-forward to: okay, we've raised, we have a CTO, and you go back to those clients and they're like, “Well, Matt, what do you want us to subscribe to? Are you doing collections?” You're like, you have to build something. And so it takes time.
Matt: Then you start to learn things. To your point about QuickBooks and Xero, their focus is all the bells and whistles that go into a more sophisticated accounting software. It's not like they've completely ignored invoices as a product. They do have an automated invoice function. They do have some templates that can be sent out. They're probably investing in AI across the entire platform. So what does that mean? It means we need to at least build a platform that gets us to slightly better than what they've already built.
Matt: Most of the feedback we get is that everyone ignores the automated emails from the accounting software. So we've got a leg up there because this is AI, but it feels like a human sending the invoice and following up with you. That's better than QuickBooks automatically sending you an email that says you have an overdue invoice.
Matt: But we also need to build products and functionality that can convince our clients and show our clients that they will collect more money faster if they use our product than what's being offered to them as part of those ecosystems.
Matt: I'll give you a good example. We onboarded a client and saw that they were only using us for about a third of their invoices. The rest you can pause, or you can turn off clients on Harvest, which is one of the things we built, for a whole variety of reasons. Sometimes you work with a big company and they require some sort of invoice submission to a supplier portal. We don't do that, so you would just turn that client off.
Matt: In this case, we were only doing like 30%, so I messaged them saying, “Hey, results are good. You can open this up to your remaining percentage.” They said, “Actually, those clients pay us in multiple installments. So sending them a message saying, ‘Hey, you owe us money for this invoice’ wouldn't really make sense. It would actually have to say, ‘You owe us for installment one.’ And if they pay that amount, then we'd have to move them to installment two.”
Matt: I asked, “How are you doing this right now?” They said, “We have a HubSpot template where somebody goes in every day and checks what installment they're on, what date it is.” So I went to Poria and said, “We've got to figure this out.” Poria came up with an incredible build. Now you can toggle between a standard client and a client that pays on an actual payment plan. It recognizes when money gets paid, whether it's a third of it, moves you to installment two, or says you're overdue for installment one and two.
Matt: We checked in on them today and they were like, “It's working great. You guys have no idea how many hours you've saved us on this.” If you had asked me two months ago what product feature we were going to build next, and I had said we're going to build this product that helps clients collect in multiple installments, I would have been full of it. You don't know what you're going to build until your clients tell you, as long as you're listening.
Matt: That's a good example of something that QuickBooks and Xero just can't handle, aren't going to be able to, and aren't thinking about. So if we can continue to add value on both fronts — we collect faster and better, and we can be dynamic in how we support those workflows — then we're off to the races. It's going to be a challenge for sure, but there are lots of SMBs out there, lots of clients with QuickBooks and Xero that need help with AR, and we're just going to keep slowly building a really great client base.
Mike: I think it makes a lot of sense. Your vision, Matt, is like if you look at Intuit, you look at Xero, and we were speaking before we even hopped on about Float and accounting tech, you can see that a lot of the main multi-billion-dollar players are focused on the ledger, but there are so many startups that build an enhanced version of one aspect of the ledger. Intuit bought TSheets, TradeGecko, and Xero bought Melio. So because it's an open API environment, it's such a brilliant way for best-of-breed technology to win. I think what you guys are doing is tackling a problem that's been ignored a lot, especially in Canadian business.
00:36:06 – The Future of Harvest: Calls, Texts, Credit, and Partnerships
Mike: Last question I have for you, Matt, before I let you go here is: where do you see the business going in the next three to five years? I know it's early days, but if you were to take a crystal ball and think about AI and all these things changing in the world, where do you want Harvest to go over the next short run of your journey?
Matt: I want to think about how I answer this. In the short term, just like Airbnb, people were like, “There's no way I would ever let anyone stay in my house.” And then obviously that turned out not to be the case. Or, “There's no way I would get into anyone's car to drive me around.”
Matt: We still hear a lot of people, especially law firms or more established professional services firms, say, “Matt, we're just never going to let something else talk to our clients. Our clients are our most important relationships.” But when you go back to them, you basically say, “Have you asked your team where they're drafting most of their emails?” Because I can guarantee they've got ChatGPT — and you probably bought ChatGPT for your entire team.
Matt: What they're doing effectively is taking invoice number, amount owed, and other details, dropping that into ChatGPT, spinning up an email, and saying, “This is the second follow-up to this client.” That's all we're doing too — but we're doing it on an automated basis across all of your invoices, and you don't need anyone to do it for you.
Matt: So they look at you and they're like, yeah, you know what? That's not that far off from what we're actually doing. This isn't as big of a leap as they thought. People who play with ChatGPT or Gemini themselves instantly realize they rely on it for a ton of things. So there's a comfort level that people are developing with AI.
Matt: I think we're not there on calling yet, but we have a lot of small businesses that have non-recurring customers, and calling isn't great for dispute resolution, but it's really great as a reminder. Sometimes you have the wrong email address, the email is bouncing, or it's going to spam. You just call someone and say, “Hey Mike, I was at your house last week for an HVAC job and your invoice is outstanding.” And Mike says, “You know what? I never got that invoice. Could you check my email and just send it to me?”
Matt: How many hours and how much money did that interaction save you? And do you care, Mike, whether that's an AI agent or not? At least at first, it's meant to be clerical, but it has access to all the data to make it functional.
Matt: Texting is another one. If you have an amount outstanding that's non-recurring and below a certain threshold, I actually like getting a text. I have Apple Pay on my phone. I get a text saying, “Hey, you forgot to pay this bill. It's outstanding.” It's so much easier than me having to find the bill on my desk, open up my TD app, or send an e-transfer. There's no reason why we can't come to people and make it easier. Those are tools that just aren't going to be used by the companies we're signed to, so it's a huge value-add.
Matt: I also think there's no shortage of value we can provide SMBs. SMB value is very siloed right now. There's lending, there's factoring, there's accounts receivable, and all this stuff. One of the biggest pain points I hear is: “The worst part is when I do need a debt collector, because inevitably I get one or two or three of these a year. I have to call someone, engage with them, and send them all the details.” Could Harvest facilitate that? Yeah, we could be a referral network for debt collection and save our clients all the hassle because we have all the data for it.
Matt: We can also provide value upstream. We see a lot of the data they're sharing on sales and how much they're collecting, and a lot of them are getting very bad offers on working capital loan sizes and egregious SMB loan offers. Can we improve that? Can we say, “Hey, with Harvest there, they've improved their collections, cash flow is much more consistent, and the rate you've given them is the wrong rate, or the amount you've been willing to lend them is too low”?
Matt: So there are a whole bunch of things we can layer on top here. But for now, we just want to make a really great platform that people are like, “I'm really happy this exists.” It saves them pain. It ties back to the painkiller idea. It solves a really big pain in their life, which is constantly being on top of overdue invoices and having someone they can point to that's doing it for them. They'll get involved if they need to, but the vast majority of those conversations don't need to happen at the strategic level.
Mike: That's amazing. That's a vision of something I wasn't even thinking about — the partnerships with potentially even banks, tripping covenants, having Harvest there maybe as a form of leverage over the rates or over whether companies are going to hit their metrics. So there's probably huge partnership opportunities with big players as you guys scale and get product-market fit.
Matt: That's the plan. You think about how your insurance company gives you a bit of a discount for having an alarm system, right? Can Harvest play the alarm system on your receivables or overdue collections just to make sure something is there, it's monitoring, it's actively working on your behalf, and your lender should feel more comfortable that your company has something following along?
Matt: It's not that the business is doing poorly. It may just be that they've been so busy on the business that they haven't prioritized cash flow. It's not that they were focused on something wrong or that anything is going wrong in the business. It's just that they weren't focused on the most important aspect, which is making sure they're collecting the money they're actually generating. Hopefully we can figure out our role across all of those different companies, and there are a lot of amazing ones to potentially partner with.
Mike: That's amazing. Well, Matt, thank you so much for joining me. I'm really excited about what you're building, and I'm going to be following you guys as you continue to scale and grow.
Matt: Thank you. And I'll plug you back — not that you have paid me to — but I'm really impressed with the ConnectCPA team. Much like Harvest, it's one of those things where you want to be focused on your core competencies, and it's great having a team you can trust to deal with a lot of the things I don't want to be focused on day to day. I appreciate the company you've built and all the people that I've had the pleasure of meeting and getting to work with early in Harvest's timeline here. So I'm looking forward to working with you and the team more.
Mike: Yeah, really appreciate it, Matt. Thanks so much.
Matt: Thanks, Mike.


Mike is a seasoned professional with a diverse background in taxation, financial reporting, investments, and real estate. Before co-founding ConnectCPA, he served as a Senior Associate at PricewaterhouseCoopers, specializing in advising small and medium-sized businesses. Additionally, Mike gained experience as a tax and accounting manager at a mid-sized accounting practice and as an Investment Associate at a real estate private equity firm. He holds a Bachelor of Business Administration degree from Schulich School of Business and is a Chartered Accountant.


Matt Himel is the founder and CEO of Harvest, an AI-powered accounts receivable automation platform that helps businesses collect on overdue invoices faster and more efficiently. Based in Toronto, Matt began his career as a lawyer before spending eight years at Drop, a leading rewards platform that was acquired by a major tech company, where he rose to VP of Enterprise Sales and Strategic Partnerships. It was there that he experienced firsthand the frustration of chasing overdue invoices and the toll it takes on cash flow - a pain point that became the foundation for Harvest. Backed by Simple Ventures, Harvest integrates directly with QuickBooks and Xero to automate and personalize the collections process, giving SMBs a smarter, more human approach to getting paid - without the awkward conversations.
