Turning a CFO Nightmare into an AI Startup with Matt Himel

Matt is a lawyer-turned-tech entrepreneur who started his career in law before pivoting into the startup world around 2014. He got his break at a company called Tilt, which set him on a path in the tech industry.

With a background in law and a deep understanding of how poorly most firms manage their accounts receivable, Matt founded Harvest — an AI-powered collections and AR automation platform built for SMBs.

Harvest uses AI agents (given human names like Pat, Luca, and Ruth) to handle invoice follow-ups, payment reminders, and collections outreach in a way that feels personal rather than automated.

The core insight is that 80–85% of AR communication can be fully automated, freeing finance teams from being the "bad cop" in client relationships. Matt's longer-term vision includes partnering with lenders and insurers to use Harvest's cash flow data as a signal for better loan rates or insurance premiums — essentially turning consistent collections into a financial health score for SMBs.

Transcript

Matt

So you always want to be a painkiller because a vitamin is like a slow drip and overall, like things are better, better for you. And so people buy vitamins because they're like, "Oh,

Mike

Hi, I'm Mike Pincus, co-founder of Connect CPA and your host at Growth Tales. Today, we have an exciting guest in Matt Himmel, who's the CEO of Harvest.

Matt

Thanks, Mike. Pleasure to be here.

Mike

I-- First of all, I really appreciate you taking the time, and, and we operate in a really similar space, so it's something that's of big interest to me.

Matt

Yeah, it's a great question. I, um, I went to business school, and one day, it's funny, the, um, the admissions person for Western Law came into our business school for, like, a lunch and learn, ended up applying to law school and, um, you know, always much more enjoyed, uh, go to business school. Um, but, you know,

Mike

Yeah

Matt

that's really what's waiting for you. And, uh, decided, oh, I gave it a good go at, at law, at law school and might as well, um, you know, kick the tires on a, on a short law career. Um,

Mike

Yeah

Matt

it was twenty fourteen or so, so a bunch of tech companies were opening, and none of them wanted me. Absolutely none of them. It was very disheartening. They're all like, "Why are we hiring a lawyer? Doesn't make any sense."

Mike

All that time in school.

Matt

Um, and I really had to reframe, I really had to reframe who I was and, you know, why I thought I could add value. And luckily, um, I got taken in by a company called Tilt,

Mike

Wow. So, a- and by the way, that's, that's I think a common story. I, I know a lot of lawyers, and I think it's similar to the accounting space where the vast majority go into industry or

Matt

Lawyers are actually horrible with their accounts receivable. We'll park that- for, for a different day. But, uh, they're very good at... Well, they're bad at getting their billings in, that's one, right? So you have to bill every hour,

Mike

Yeah

Matt

holistically. And I think they're working on it. But, uh-Yes, billing every hour sucks, and then billing a client for those hours sucks,

Mike

Mm-hmm.

Matt

And so you get to 60 or 90 days, and then all of a sudden your client's not really taking your collection efforts seriously.

Mike

Mm-hmm

Matt

company and a repeatable task. Like those two things complement AI really well. Um, and so when I was looking for a business, I knew I wanted to combine those two things, and I combined

Mike

Yeah. Of course. Yeah.

Matt

You know, it's a very popular like startup thing, right? And so you always wanna be a painkiller because a vitamin is like a slow drip

Mike

Yeah.

Matt

And when, when I know I have a really great customer is they're like, "Matt, you couldn't have come at a better time. Like we're, you know, we're knee-deep in this right now.

Mike

No, that's... I, I think that's a great description. It's, uh, I follow a lot of SaaS business gurus. I think one of them is, uh, Jason Lemkin,

Matt

One thing you'll really appreciate, Mike, 'cause I'm sure you know when you chat with founders or people that are coming to you for new business and you ask them to describe their, like,

Mike

Yeah

Matt

a hard time. But what you see isPeople say, "Oh, yeah, AR is, like, an issue, and we'd love for you to help us with this, and, you know, let's connect. And, um,

Mike

That's a great point, and I wonder how much of your go-to-market with Harvest is the education piece of, like you said, you come in, you meet, you meet a founder

Matt

It's, it's huge. It's a really good point, Mike. There's a couple of things that I'll say on a sales call, and not all of them will necessarily hit,

Mike

Mm-hmm

Matt

paying an empty AR agent to be the bad cop for them. And just having another layer to their outreach allows the finance person to no longer be the

Mike

Yeah

Matt

or bad, bad person. And then also, like, there's leverage, right? Because what's happening is if finance-- if you send an automated invoice and nobody responds, and you send another one

Mike

The whole nine, yeah

Matt

vacation and like the whole nine. And you just add, you know, we have Pat, we have Luca, we have Ruth, people I come up with names. But- you add someone, and all of a sudden you have another layer. So, you can send an automated or, you know, Ruth can reach out and then, um, then finance can come on top and say, "Hey,

Mike

Mm-hmm.

Matt

Um, can you save resources, right? Like, eighty to eighty-five percent of the emails we send can be automated.

Mike

Mm-hmm.

Matt

There's, like, no reason why somebody needs to get involved. Vast majority of emails are, "Here's your invoice," following up on your invoice, taking payment. You know, anything strategic

Mike

Mm-hmm

Matt

it's just not a, not a great task, right? Like, nobody enjoys [chuckles] ... Very rarely do I come across someone who's like, "You know what I love

Mike

Yeah, and I, I think it, I think a point you made there, which is like you can almost set it and forget it, meaning let the technology be dynamic for you. People are not disciplined,

Matt

Yeah

Mike

technology around.

Matt

Yeah.

Mike

It's not just like, hey, automation just means like a basic like we're gonna do an email out. Uh, but-I wanted to ask you the actual function itself, what percentage of companies you think

Matt

Look, you know, like as a human, we make decisions based on kind of how we feel. You don't wanna send a follow-up on a Friday afternoon. It feels like not the right time. Even

Mike

Mm-hmm

Matt

you know, should I wait, and so forth. And so you have all this kind of like human emotion, you know, put into it. W-we have the reverse, which is we're democratizing best practices,

Mike

Mm.

Matt

It knows, you know, the best subject matter to like put in the subject headlines. It knows the best buttons to push, when it needs to be pushed. Here's a,

Mike

You mentioned, Matt, uh, being a part of Simple Ventures. Obviously the big push for not only innovation in Canada with all the things going on in the world

Matt

Yes. I can't say enough amazing things about Simple. Um, obviously with Mike's leadership, Mike Katchen's leadership, um, he's, uh, created an amazing, you know, additional organization f-

Mike

Mm-hmm.

Matt

And what you get there is not only some really great people who can help them make investment decisions, 'cause they pull them in. And when I, when I, I went to investment committee,

Mike

Mm.

Matt

But we're really the first, um, kind of AI, you know, forward.

Mike

Yeah.

Matt

And we can, we can get into like what AI means for, for Harvest, but we're really the first AI forward and so, um, we really needed to find a CTO early,

Mike

Mm-hmm.

Matt

And in the middle is like, you know, a little bit of tension about like, you can't just, you know, vibe code your way to a product, um, you know, from this side and be like, well, you don't need,

Mike

Mm-hmm

Matt

tech debt and things that are important to building a company, but also on this side, you know, embracing new technologies and, uh, being able to build really quickly

Mike

Yeah. I think that's e-especially the challenges of being a Canadian business, [clears throat] they can't be understated, and I think it's such a powerful thing

Matt

I think, like, when you're, you're non-technical and you're hiring a technical resource, you have to rely on other people to, to, like-

Mike

Mm-hmm

Matt

vet their technical skills, right? So again, leveraged a couple people through a relationship with Simple. Um, there's a couple LPs that have, "Yeah, he's awesome. Like, he's technically sound," right? So y- I think, I think people can do that and, um, you know, you don't have to rely on yourself to, like,

Mike

Mm-hmm

Matt

you know, they're amazing at building, and, you know, they solve problems and, you know, build amazing platforms," great. Okay, great. Like, that's, that's like baseline. I need that.

Mike

Yep.

Matt

So, you know, on a daily basis, it's just the two of us working back and forth. Um, and, uh, it, it like, you couldn't make a bigger mistake if you tried to hire someone that you, you know,

Mike

Mm-hmm

Matt

and I had the pleasure working with Darren Fung at, uh, Drop. He's incredible, um, CTO and just engineer, and you get to learn, you know,

Mike

Mm-hmm.

Matt

Right? And then our client comes in and says, "Yeah, this is kind of like what I asked for, but like you didn't think about these eight things, and it's just like,

Mike

For sure. And you've got the CTO now. You've got funding figured out. A mission-critical, I guess, problem you're solving in the sense that I think like right now Intuit

Matt

It's a very good question. When we, when we first started to ideate for Harvest, we reached out, or I reached out to a whole bunch of friendlies and said, "Hey, like, And then they would give me their, like, hardest collections and basically be like, "Here's ten, you know. I haven't heard from those clients in three years. Like, have at it," right? And you're like, "Oh, this is so great." Like, everyone's willing to give you, you know, work to do, and they're willing to pay you and, like, what a great idea for a business. And, uh, you go out, Like what... Like, you have to build something, and so it takes time. And then you start to learn things, right? Like to your point about QuickBooks and Xero,

Mike

Mm-hmm

Matt

some templates that can be sent out. They're probably investing in AI, you know, across the entire platform. So what does that mean? It means we need to, A,

Mike

Mm-hmm.

Matt

So like, okay, so we've got a leg up there because this is like a human. It's AI, but it feels like it's a human sending the invoice, following up with you, and that's better than,

Mike

Yeah

Matt

invoice submission to a supplier portal, right?

Mike

Yes, yes.

Matt

Like, so we're not... We don't do that.

Mike

Yeah, yeah.

Matt

So you can just turn that client off, right? But we work for your other eighty percent of clients. In this case, we were only doing like thirty percent, so I messaged them being like, "Hey, um,

Mike

That's right

Matt

hundreds of invoices a month." So I went to Poorya and I was like, "We've gotta be able to figure this out." And, um, Poorya came up with some, um, you don't know what you're gonna build until your clients, you know, tell you and if... as long as you're listening. Um, but that's a good example of like something that QuickBooks

Mike

Yeah.

Matt

It's gonna be a challenge for sure. But there's, there's lots of SMBs out there. There's lots of clients of QuickBooks and Xero that, you know, need help where they are,

Mike

I think it makes a lot of sense, and I think your vision, Matt, is like if you look at, if you look at Intuit, you look at Xero, like we were, we were speaking, uh,

Matt

Melio. Yeah.

Mike

Yep. And, and so all these, these applications, they're-- because it's an OpenAPI environment, it's such a brilliant way for tech- the best debris technology to win. And, uh,

Matt

I wanna think about how I, how I answer this. In, in the short term, you know, like, just like Airbnb, right? People, people are like,

Mike

Yeah.

Matt

Like, that's crazy. And then obviously that turned out to be- not the case. And it's like, there's no way I would get in anyone's car-

Mike

Uber

Matt

to drive me around, right? Um, and we, we heard a lot of people, and I still talk to like law firms who are more established, like, you know,

Mike

Of course.

Matt

"So what they're doing effectively is taking invoice number, amount owed, and whatever, and then dropping that into ChatGPT, spinning up an email and saying, 'This

Mike

Yeah. Yeah.

Matt

Like, "Actually, no. It's, it's Michael P." "Oh, wow. I, I don't know why I have it wrong, but I will send it to you," and, and off it goes. And you're like, how many hours and money did

Mike

Sure.

Matt

I get a text, be like, "Hey, you forgot to pay this like bill. It's outstanding. You're a deadbeat." Like-

Mike

Phone's always with you

Matt

double tap your phone and pay on A- on like Apple Pay. Like it's so much easier than me having to... I have to find the bill on my, on my desk.

Mike

Mm-hmm

Matt

you know, like accounts receivables, and there's all this stuff. And if you're an SMB startup... Like one of the biggest pain points I talk to SMBs, they're like, "You know what the worst part

Mike

Yeah

Matt

you know, egregious SMB o- like loan offers. And can we improve that? Can we say, "Hey, with Harvest there, they've improved their collections. Cash flow is much more consistent. You know,

Mike

That's amazing. And, uh, yeah, Matt, that's, that's a vision of something I wasn't even thinking about, the partnerships with,

Matt

That's, that's the plan. You think about like, um, your insurance company gives you a bit of a discount for having an alarm system, right?

Mike

Right.

Matt

Um, and so can like Harvis play the alarm system on your, you know, receivables or your overdue collections just to make sure, hey, there's something there, it's monitoring,

Mike

Yeah. It's amazing. Well, Matt, thank you so much for joining me. I'm really excited about what you're building,

Matt

Thank you. And, and I'll, I'll plug you back just because, uh, not that you've, you haven't paid me to, but I'm- really impressed with the, uh, Connect CPA team, and it's been, uh, much like Harvis, it's one of those things where like you wanna be focused on, um, you know, your core competencies,

Mike

Yeah. Really appreciate it, Matt. Thanks so much.

Matt

Thanks, Mike. [outro music]