Building Lasting Success

Mike Pinkus: Over the last 10 years at ConnectCPA, we've had the privilege of witnessing the incredible journeys of over a thousand businesses. We've been there for the thrilling highs and daunting lows of entrepreneurship. We've celebrated wild successes and monumental exits, and we've also stood by businesses as they've navigated the stormy seas facing roadblocks and challenges that every entrepreneur encounters in their day-to-day grind. Join us as we dive deep into the stories of these resilient individuals who dared to dream, who persevered, and who were a testament to the power of entrepreneurship. This is their journey, their lessons, and their triumphs. Welcome to GrowthTales. I'm your host, Mike Pinkus, co-founder of ConnectCPA.

Mike Pinkus: Today I am incredibly excited to be interviewing Jamie McDonald and Jamie Schulman. The Jamies are well known in the accounting tech space, and rightfully so. Over the last decade-plus, the Jamies have been involved in three startups—first co-founding Sparkroom, then scaling Hubdoc all the way to a $70 million exit to Xero in 2018, and finally acquiring A2X with the goal of applying their decade-plus of experience to take the company to the next level.

If you've met the Jamies, you know they're not just genuinely nice people, but they're also incredibly humble. With ConnectCPA being an early customer of Hubdoc, we had the privilege of getting to know the Jamies really well. A decade later, we consider them not just ecosystem partners with A2X, but friends and business minds that we look up to.

In this episode, the Jamies opened up about some of the challenges of scaling Hubdoc. They also explained how difficult it is going from zero to one and obtaining product-market fit. Finally, we discussed how the Jamies have maintained such a strong relationship, trust, and alignment on their core values throughout their journey of running their businesses.

I took away so many business lessons from this conversation, and I hope you do as well. Jamie and Jamie, thank you so much for joining me today on GrowthTales.

Jamie McDonald: Thanks for having us, Mike. Awesome to be here. Mike, we're excited to continue our long collaboration with you and ConnectCPA.

Mike Pinkus: Yeah, really appreciate you guys joining. You both are super busy. We actually met back in, I think it was 2014. Yeah. So it's been a decade that we've, uh, known each other, and, uh, I have huge admiration and respect for the two of you because I believe you're now working on— is it your third startup?

Jamie Shulman: That's right.

Mike Pinkus: Third startup. And you guys have achieved such huge success in scaling out Hubdoc. And the one I'm most familiar with of those three startups was the journey with Hubdoc, all the way up to the exit to Xero. But also, being a customer of A2X—an incredible product that is really changing the game in the e-commerce world.

But today, I want to learn a little bit about the story of Jamie and Jamie, because I think you guys have such a unique relationship, having been in business together for so many years. But before we get started on that relationship, I want to just talk about Hubdoc really quickly.

You guys built a really big company, had one of the best tech exits in Canada in a long time. What was the biggest challenge for you two in growing Hubdoc over that, I guess, five-, six-year period? Or—well, more than that, even.

Jamie Shulman: You want me to give it a shot? I'll get started. Jamie, you jump in.

Uh, um, yeah, thanks Mike. This is fun. Great challenge. I mean, I would say, thinking back now—because you've got us thinking back 10-plus years, it's even longer than that, so a dozen—I would say just figuring out at that time what to build. Not to mention, you know, how to sell it, market and sell it, and then how even just to run a business.

We'd had a previous startup, Sparkroom, before that, but this was, you know, a new area for us. We started Hubdoc in part because we were frustrated with doing the books at our previous business at Sparkroom. And so, as we came at it, we had two ideas. One was the bookkeeping for a business and solving that, but the other was on the consumer side.

We were kind of getting on with our lives—with two kids, and a household, and our wives. And we thought also there was an idea around organizing our household and the financials there. And so, figuring out what to build was a big piece. And we started on the consumer side; we thought we were going to help people organize their household financials.

And as we started to grow, as we started to build out the product and then go to the market, figuring out the exact market was probably where our biggest challenge was. We spent too much time thinking about selling to consumers and the product for consumers in the household. And it turned out that the real opportunity was with businesses and ultimately accountants and bookkeepers.

So, you know, I'd say that that was probably the biggest challenge—on the early side—was just figuring out kind of the product-market fit. And I referenced, you know, building, selling, and running a business. I guess we've always thought of those as kind of the three circles of running a business. And they're different: the product, the customer, and the actual business itself. And so just figuring that out in the early days before we kind of scaled was probably where I'd say was one of the greatest challenges.

Mike Pinkus: And I guess I'd follow up with that—and maybe Jamie McDonald might have the answer to this one, I'm not sure which of you would want to answer this—but what made you decide to sell Hubdoc after building it out to the scale that it was? 'Cause you built a big brand that was really well known in cloud accounting. What made you guys decide to sell?

Jamie McDonald: I can take a crack at that one. I mean, I think Jamie might have undersold the biggest challenge. Like, there were years of darkness where we'd show up in the office and we had nothing to do. We'd have stuff on the wall—like literally "Bitcoin," "Let's disrupt therapists"—and like, we have money, let's go do something else.

Jamie Shulman: For you, Jamie.

Jamie McDonald: And then literally, the day we turned it on and started talking to accountants, it started selling itself, which was, um, which was awesome.

You know, I think the reason we decided to sell the business—we had kind of two paths. We had a term sheet from, like, the best SaaS investor in the world to keep going and put $25 million USD into the company at the time. And we had a competing offer from Xero to acquire the whole business.

And I think we loved the team, we loved the customer base, we had energy for the business. But you'll remember that one of the core value props of Hubdoc was ingesting data from banking platforms, like what Plaid or Flinks do. And we used web scraping to do that, and it was just getting harder and harder to do and more expensive.

We couldn't deliver a product reliably to our customers. Like, I couldn't go to you and say, you know, you've got 500 clients, Mike and Leo, and you want bank statements reliably delivered for all of them every month on the first of the month—or whenever they become available. You know, two-factor authentication and IP issues meant that we couldn't always go to Scotia and get those bank statements for your customers.

And so, as the cost of delivering that service was increasing and the reliability of doing it was decreasing, Jamie and I just looked at each other and we felt uncomfortable with the risk looking at five years ahead.

You know, we were also competing with Receipt Bank—Dext, at the time—in the data extraction space. And their product was better than ours in that space. We had the bank statement ingestion, and we did that first, and that won us a ton of customers in North America especially. But we just didn’t feel we could reliably do that at an effective cost and make money looking ahead to the next five years.

Jamie Shulman: You know, and Mike, I'm gonna add—I’ll add one thing to both of those kinds of questions.

On the first one, Jamie's comment on the darkness—he said it well—which was, while we were pivoting, I guess, from this consumer idea to organize your household over to the business and bookkeeping side. And this is something for entrepreneurs—we frequently mention this—it's really important to find that product-market fit, find exactly where the market wants to go. And so we got caught in that middle, where we were seeing that businesses were using it, but we didn’t have a lot of capital, and it wasn’t clear that it was going to be a business to serve accountants and bookkeepers and businesses.

And so we really had to rethink the approach. Also, it did get dark, and we had our finger on the proverbial shutdown button at times. And then, thankfully, had some people like yourselves and Chad and others believe in us. And so we got to keep going.

The second thing I’d say is, on the decision to sell—reflecting back, with hindsight—Jamie, you nailed it. It was really the product issue that was a challenge for us around the bank statement ingestion. But also, we were cognizant of the larger financing and M&A environment. And at the time—this is back in 2018—you know, the offer we got was a very large revenue multiple.

Which now seems obvious, but at the time, it was clear that multiples could contract. And you could work extremely hard for another five, seven, ten years, and ultimately, at the end of the day, your shareholders—all of us—could end up with a less optimal, less optimized outcome, even if you grow revenue in the business over those years. And so there was a little bit of that component too.

Jamie McDonald: Take liquidity when you can get it. Yeah.

Mike Pinkus: Before we jump into A2X, I do want to comment on one thing you're both talking about—because you guys are close friends, it seems, beyond business partners.

How did you guys navigate during that time where you mentioned you couldn't reliably get the bank statements? So privately, behind closed doors, you're like, "This—there's things not working here on the technology front that we need to solve."

Did you guys navigate your relationship as co-founders in a business when something wasn't working? Like, you're trying to fix problems—I guess that's what business is: solving these problems. But what was that like when you guys were going through that? Like, imagine the offer didn't come before it came.

How did you guys navigate that when you were struggling with two-factor authentication, all these technology changes? I...

Jamie McDonald: I can take the first crack on that. Mm-hmm. I mean, like—listen—the way we work together is, I’d say, just totally aligned on values. And like, Jamie’s a person I have 100% trust in, and who always has my back. It was my kind of— I had the responsibility for the product and engineering team, and so it was my problem, effectively, but it never felt like my problem.

I mean, we were trying a hundred different things, and we’d been doing—we’d been building scrapers—for seven or eight years, and we knew the problems pretty intimately. And we just didn’t have conviction that we or any other company in the world would solve them. So I don’t think—it wasn’t like there was conflict in our business relationship over that.

I mean, Jamie was responsible for all of our customer and revenue relationships. You know, the number of times I told him, “Go sell what we have, I’ll go build what I can,” and we just went and kept doing that, right?

So I don’t think—I can’t remember, like in kind of 20 years of working together, where we’ve ever had a giant disagreement that was even approaching unresolvable. Like, if we disagree, it’s just like, “Okay, we’ll try your thing, or we’ll try my thing and we’ll see what works.” And like, it’s very rarely one of these one-way-door things where we disagree. I can literally think of zero times in 20 years.

Jamie Shulman: Yeah, I mean, I echo that too, Mike. And I think you started with, you know, shared values. We don’t take it for granted—it is what it is, whether it’s luck or we’ve worked on it, or both. But, um, you know, behind that or alongside that, trust. And so we trust each other deeply—as much as one could trust anyone.

And we also follow our own values, you know, values that we literally put up on the wall, both at Hubdoc and A2X. Just the idea of transparency and being human. These are things we talk about with our colleagues all the time. But, you know, we’re open with each other, we’re honest with each other, we trust each other deeply.

And, you know, if you have shared values, then you’re just going through the hard times together. Mike, I’m sure you and Lior have had your share of hard times.

So yeah, I mean, it wasn’t the most fun at the time, but when you are in business with someone close like that—someone you love—it really makes it not just more tolerable, but—you know, I almost want to say fun, but the dark times aren’t fun.

Mike Pinkus: I appreciate you guys sharing that, 'cause hindsight's 20/20—things worked out really, really well. And Jamie, to your point, like, Lior and I are still very, very close, and similar to you guys, you have disagreements, but our values are aligned. And that's why over a decade you're still extremely close.

But the reason why I asked the question is because hindsight is 20/20. Meaning before the exit, when you're facing those real challenges, that's really where you get pushed. You could look back on it and be like, "Oh, we were aligned, it was gonna work out." But when you're in it, in that moment, it comes down to, I guess, that relationship you two have.

Jamie McDonald: Well, there was never like certainty it was gonna work out. No, there just—there isn’t. If you're doing entrepreneurship right.

Like, you know, like, we always talk, we basically worked in obscurity for 10 years. And then, you know, there's an article in the paper one day, and you're the king of the internet for 24 hours, and then you go back to obscurity. Right? It's just—there is no certainty. You just try and do the best thing to do that particular day, right?

And I mean, just on the transparency thing—and extend it to our customers, right? I mean, we'd talk to you guys like, “Hey, why aren't—I’ve got all these clients on Royal Bank and you're not fetching their statements.” And we’d just explain to you that web scraping was hard and we were doing the best we can. And, you know, you’d make a decision on whether it’s worth that 20 bucks a month per client, or whatever we were charging you, right?

And it was stressful. And that problem—like, people always ask us if we’d ever get into the scraping business again. Like, if I could reliably fetch bank statements and check images from the North American banks, I know I could build a hundred-million-dollar business selling terms.

But like, nobody’s able to do it—because the banks don’t want data off their platform.

Jamie Shulman: You know, Mike, one last thing I thought—codified values. “Always be learning” is another one we've focused on. You know, hiring and working with curious people. And so, in addition to learning from each other, we're always just broadly thinking about learning as we're going along.

And I think if you have an open mindset—with your eyes open and your head on a swivel—without any level of complacency, like, you just can be available for the opportunities as they come. Because with both Sparkroom and Hubdoc, both of them had moments where we really were considering stopping. And you just have to keep persisting.

Other times weren’t as existential, but still—you just have to keep working ahead. But I think if you have an open mind, and you don’t think you know all the answers, and you're always learning, you can kind of be available when the opportunity surfaces in front of you.

Mike Pinkus: Yeah, it’s amazing. And I want to now pivot a little bit into A2X, because you’re both wearing the A2X t-shirts. We're huge fans, obviously—ConnectCPA and A2X.

But I'm going to open with asking you both—anyone can Google the Hubdoc exit, it’s pretty public. It was quite a big exit. I’m sure life-changing in terms of achievement. But you’ve been at it for a decade—running a business is extremely hard, as you guys are letting me know about.

Of all the challenges you had—you’ve already achieved the exit, multiple now—what made you guys want to, after achieving such success, get back on that treadmill and get involved with A2X?

Jamie Shulman: I mean, I’d say, Mike, that—you know—Jamie and I are similar age. We both worked in our previous careers in large organizations. And, um, after selling Hubdoc—you know, we’d had a ton of fun, ups and downs, but really a ton of fun for about 10 years.

And then the pandemic hit. We had an earn-out with Xero, where we worked there for 18 months, which was great. And then that took us right into the pandemic. And we both have—we had teenage kids, we have teenage kids now—but we had teenage kids at the time, and we took a little bit of time off. Not to mention it coincided with the COVID pandemic.

And so we didn’t really have any new ideas. We talked a lot during that period of time, isolating with our families. We’d done angel investing over the years, we were thinking of new ideas—didn’t have any.

And so we kind of identified that getting back into it through buying a business was kind of in the middle between doing some angel investing but also starting something from scratch.

We knew the community very well—the accounting software and accountant/bookkeeper community quite well. And I think, as we reflected on what maybe we had done successfully with Hubdoc, we thought—and were given the feedback—that listening to customers and building for customers was something that had worked.

And so we started to think a little bit about this environment, and ecosystem, of accounting software. And we knew A2X as a company that was beloved by customers. The products were loved, and we knew the founders of it. And that kind of got us there.

But I’ll let Jamie fill in to that. That’s where I think, broadly, though, it was just—we weren’t going to stop. If you were implying that we were going to retire or something, that never entered our mind. I don’t think we even—that never—we like...

Jamie McDonald: Yeah, my line there, Mike—'cause the only thing worse than working is not working.

We just like—we like building products and teams. We like talking to customers. You know, you can go at different levels of intensity at different times in your life. And I don’t think either Jamie or I had the desire to go back to the start-from-zero phase, seeking product-market fit and dealing with the uncertainty around that. Or, at least, we didn’t at the time we were thinking about what to do next.

It was like, you know, let’s try and find something great and take a crack at scaling. We knew Paul and Ashley a little bit—when we left Xero, we actually tried to make an investment in their business. They liked the money, but they were open to selling it.

And I just think their founding relationship is similar to ours. They think like we do about customers, and about how to treat the team and grow the business. We were just extremely fortunate that they were open to a transaction, you know?

I think—Jamie feels the same way—we feel like we’re kind of stewards of the brand and the company. And it feels different than being a founder, but I just—I'm super excited to come to work every day on this problem.

Mike Pinkus: Yeah, and it's interesting—you mentioned you guys are angel investors as well in a lot of investments. And if you look at starting from scratch, like what you did with Hubdoc, versus taking over a business like you've done at A2X, and then angel investing—which is more passive—I guess a lot of people in your shoes would’ve chosen the passive route.

Because, like, operating is operating. Whether the business is from scratch or not, the problems are still there. You've got to deal with the challenges and all the things. Operating a business is not easy—especially at the scale that A2X is at.

You guys consistently choose the path of being operators, as opposed to being behind the scenes. I wanted to ask you about the industry that you chose—being e-commerce. E-commerce has been huge, obviously, and it's still growing at a pretty good clip.

Why e-commerce?

Jamie Shulman: I mean, we bought A2X in 2021—early 2021. And as I mentioned, you know, we both have teenage kids—not everyone’s quite there yet, but you’ll see—as you see how they behave, like, our households, there’s quite a bit of e-commerce going on. Most shopping’s done—well, a lot of it’s done—online.

And with the pandemic hitting, that was another factor. Pretty impressive industry, just on the whole. But we love entrepreneurs. You know, in the last couple of years, Mike, we’ve had the opportunity to attend local events in e-commerce and with entrepreneurs. And you go to an event and there’ll be, say, a dozen entrepreneurs there—and they could be selling stickers, socks, vacuum cleaners, bubble tea, slippers—it goes on and on.

All these kind of multi-million-dollar businesses. And you just look around the room with these entrepreneurs—and it’s pretty wild. So I think the combination of it being a scaling area, an exciting area—like retail is moving more and more online—and it’s still combined with the fact that these are all entrepreneurs… it’s just kind of inspiring.

Mike Pinkus: And I guess a follow-up to that is—I don’t know where we’re at in cloud adoption—but I think part of the huge market opportunity in helping on the accounting side with e-commerce, what A2X solves, is that we still have a massive amount of migration that’s still going to happen from desktop to cloud over the next, call it, five years.

I don’t know how you don’t have everyone already in QBO and Xero already, but accounting is slow to adopt. It’s one of those industries that’s not very quick to adopt.

Do you think part of the market opportunity you guys have is the fact that we’re still, in my opinion, maybe in the early to mid-innings of just converting to the cloud? Because there’s still a huge segment of the market that’s running businesses—and SMBs—on desktop?

Jamie McDonald: I think—yeah. I mean, we have competitors that have really large QuickBooks Desktop businesses. Like, we don’t support desktop.

I think a lot of e-commerce businesses stay on desktop because their inventory module is actually good, right? Cloud inventory solutions that are native to Xero and QuickBooks still leave a lot to be desired.

I mean, we love e-commerce. We think e-commerce is going to be bigger in 10 years than it is now. There’s going to be more sellers. It’s not a market without its challenges. The fact that e-commerce accounting is hard is, I think, good for ConnectCPA—and good for A2X, right?

Doing e-commerce accounting is challenging. Shopify and Amazon’s pace of development—and how rapidly those platforms change, and the data changes—just makes it hard. And so, hard problems are good for software companies that have a specialty.

And so we think—there’s still, in our category—we always talk about category penetration. Like, two indexes: Hubdoc and A2X. How many people are using kind of automation or extraction? It’s like—70% of the market probably still isn’t converted there. And that’s in what are some of the most popular apps inside of Xero and QuickBooks, right?

And like, in e-commerce, you know, we look at our share, we look at our competitors, and the native apps inside QuickBooks and Xero. And like—I guarantee 70% of the market is still doing reconciliation manually against Shopify, Amazon, Etsy, Walmart sales.

Mike Pinkus: Yeah. And A2X solved that massive problem—because before this, it was all manual. Like, all manual. And I can attest to the fact that you have e-commerce businesses popping up every day, and then you're conducting bookkeeping where you now need to train bookkeepers to be experts at looking at reporting in Amazon, Shopify—all the e-commerce backends.

And it's a disaster. And it's definitely not scalable, right? But with inventory being such a big, complex thing, do you guys struggle with what to build next? Because there are so many directions you could take A2X.

How do you figure out what is the next thing to build?

Jamie McDonald: Talking to people like you I think is the easiest answer.

The inventory question is an interesting one specifically—because how many inventory platforms are there out there? Lots. Some people manage their inventory in spreadsheets. Some people manage it inside Shopify. It’s a very fragmented problem, and there is no one killer app for managing inventory.

It’s our view that there probably won’t be. Our approach when we look at that space is like: Huh, really hard. Lots of people doing it. Let’s try and ingest data from all those platforms so we can consolidate the data.

You know, ours is an accounting problem. And like—the first problem in inventory is an operations problem. Which is: How do I get my goods from the manufacturing facility to a warehouse? And how do I get them from that warehouse to a customer?

And the accounting problem—the COGS (Cost of Goods Sold) problem—is downstream of that.

Jamie McDonald: Mm-hmm. So the first problem is like: How do I run my business, sell things, and get them to customers?

And so with regard to inventory—never say never—but I don’t think that’s a place you’ll see A2X going. You know, we’ve talked to your team a lot about ingesting payment gateway data, both for e-commerce sellers and for people outside of that.

That’s a problem that’s in our wheelhouse. Like, we ingest all of the sales and cost data from the merchant—from the selling platforms. So, what are analogous places where you can automate revenue and cost accounting, where there’s tons of customers and the problems are repeatable and can be solved by software—but not so easy that you can just hook up an API and send it straight to QuickBooks?

So, I think the short answer of how we get product ideas is: talk to smart accountants and our customers. And then, you know, there are a hundred different ways we can take the business.

But I think—this is the world we live in—everyone is thinking about accounting automation. In our world anyway. And the big question is: How do we ingest data and accurately reconcile books so that firms like ConnectCPA can focus on advisory and the more complex work, and get out of the reconciliation business?

Mike Pinkus: What I find so interesting—just hearing you, Jamie, explain that—you can tell there's just so many years of software development and product-building experience behind it.

And I say that from the perspective of—when I think about problems in our business, it's not as clear as the way you just articulated that. You can tell that you guys can somehow, through all these years of experience, get to the answers quicker than I guess it would've taken if this were your first startup.

Jamie McDonald: You’d hope that to be true—but, like, every situation's a little bit different. And I don’t know, there’s something about the naive tail—like, all the things you don’t know when you start.

Like, Jamie and I—whatever, we were talking yesterday about a product manager at A2X who’s excited about the personal financial management space. Like, “build Betterment” or a real-time income statement, balance sheet, net worth statement. And I’m just like—“Ah…”

Mike Pinkus: You tried.

Jamie McDonald: Yeah. Terrible idea—but somebody’s gonna build something good there eventually, right? And I’d be a customer of that product.

But in the same way, people come to us with, “Oh, I’ve got a web scraping idea,” and we’re like, “Oh, that’s terrible.” But maybe it’s different now—with AI, maybe the scrapers can run autonomously and fix themselves.

And so—I don’t know. I saw in BetaKit that the Flinks founders are doing some sort of ingesting data from utilities and energy companies and delivering it via API. And I’m like, “Okay… is that a better idea than bank data?” Because bank data fetching was impossible. They gave up on that—or they sold that business to National. Why is this one going to be easier?

So I don’t know—that’s a long way of saying: there’s a lot of pattern recognition for both of us, and for the teams we’ve worked with. One of the joys of A2X is that we’re working with a bunch of Hubdoc people as well as the original A2X team—the OG team.

So there’s just a decade of experience working together, which is joyful and really meaningful. And so you hope you make good product decisions. But I don’t know—in the kind of AI-native world, I feel kind of out to lunch and behind all the time. Like, it’s changing so fast, right? So you just have to keep reading, learning, and using tools—or else you...

Jamie Shulman: And Mike, you referenced something that I thought was quite insightful. You were talking about the desktop businesses out there.

And, you know, one thing we’ve learned over the years, too, is sometimes things take longer than you might think—for example, getting over to the cloud. But sometimes things move more quickly. And you don’t necessarily know which way it’s going to go.

And so that’s one of the challenges: trying to figure out—are we serving the whole giant roster of businesses still on desktop, moving to the cloud and just in the early stages of the journey?

But then we’ve also got good connections with, and are working with, folks who are on the other end. They want us to build the most granular, AI-run, all sorts of fancy—and more detailed and complex—solutions.

So just trying to figure out who we’re serving, and with what, and where to prioritize our efforts. Because you can’t—you know, we have a laundry list of hundreds of things at A2X that customers really want us to build. But you can’t build everything. And time’s a zero-sum game.

So that’s one of the challenges, too—figuring out exactly where to go, generally, and also specifically with the product.

Mike Pinkus: Yeah. And Jamie McDonald, you mentioned familiar people. And Jamie Shulman, I know this is something that both of you probably talk about a lot, but there are a lot of familiar faces from Hubdoc.

And we've spoken a lot about product, but what I’m really interested in understanding—from that continuity of people who were at Hubdoc and are now at A2X—how important is culture? Because you guys have built really great cultures at each of these companies and really great organizations. And you’ve kept familiar faces along these journeys.

And we've been talking about values as well, so maybe it’s a long-winded way of asking:

How important is culture, and what are some of the values you look for in people?

Because you have had continuity of people that have stayed with you over all these years.

Jamie Shulman: Yeah. I mean, one thing we—we’ve been, as you alluded to, Mike—we’ve been working together for, you know, 20 years across three businesses.

And we realized somewhere along the line, early on, that we were focused on the North Star of delivering the best customer experience possible—an experience where customers like yourselves would tell everyone about this business and these products.

But we realized early on that there’s a second North Star, which is around delivering the best employee experience. Having people—today—be moving toward the point where they’ll look back in 25 years and say, “Gosh, Hubdoc back in 2015, that was the best work experience I’ve ever had.”

And in order to think that way, you’ve got to ask:

What would make someone feel that way, decades later?

And that’s really the lens we try to use.

Jamie Shulman: Well, you know, there are all sorts of things you need to deliver to the employee experience to make them feel that way. And ultimately, if you have employees who feel like it was the best place they've ever worked, well, they’re going to deliver the customer experience.

So it's things like growth—we’re always constantly thinking about how to provide opportunities for individuals to grow personally, in the business, and in their careers.

We’ve just found that focusing on people individually makes a big difference. Even at Hubdoc—where I think we were 120 or 130 people when we sold the business—we were still interviewing every single person. By the end, it was maybe more of a values interview at the end of the process, but we interviewed everyone who joined Hubdoc.

And that's because every single individual was critical. And if you think of it that way, you can end up putting together a team that’s going to feel the way we hoped they would—and that delivers the continuity we’re talking about.

Mike Pinkus: And I think you could feel it. When I say you could feel it—from the time we went to your Hubdoc offices back in the day—there was an energy around the office. It was always special. There was this brightness to the way people interacted.

And also, the events that you guys put on now with A2X—it is so dialed in. And I think what you just described, Jamie—you can feel that. You can feel that there are aligned values in the people that you bring into the organization and in how they operate as well. They carry those values through, and you feel it.

Jamie Shulman: Yeah. One of the values that...

Jamie McDonald: I mean, go ahead—

Jamie Shulman: I think we’re going to say the same thing. One of the values I was going to mention was “give a shit.” It's one we take pride in.

And it’s interesting, interviewing people and trying to suss out: are they going to give a shit? Some might say “take care,” but we like “give a shit,” I think.

The idea being—you want people who really care. Whether it's that they’re at a booth at an event—not scrolling on their phones but actually engaging—whether it's believing in the purpose, caring about the office being clean, caring about each other at work, or caring about the customer.

You’ve got to find people who are actually going to care.

Sorry, Jamie—I interrupted you. Go ahead.

Jamie McDonald: Oh no, no—we're good. I think we’re in the same place.

Another word for that is—we definitely screen for, like, I want to say a founder mentality. People who own the problem. The thing that makes us happiest is when people who’ve worked with us go on to start new businesses.

Like Yousuf, now at Relay—he was with us from the darkest days at Hubdoc, helped us build that business, and then went on to start Relay. Just like sending Yousuf—or Jeff, who runs marketing for us now—to a customer... those are people who can do the job as well or better than Jamie and I.

And that just gives you comfort. The fact that we’re working with, I don’t know, half a dozen of those people now who’ve been with us before—it’s a compounding advantage as a business builder, if you have high-quality people who want to work with you repeatedly. Right?

And so, that’s just part of the joy of what we’re doing now. And I think what we hope to do over the next 20 years of working together—which is: curate teams of amazing people, create opportunities for them to grow professionally, and to make money—obviously—and to have fun. And just do it over and over again.

Mike Pinkus: And you two have done it better than most that I've ever seen. And I want to be respectful of your time, so I have one last question for each of you:

If you could look back 20 years and give advice to your younger self—or to younger entrepreneurs that are in the midst of their journeys right now—you guys have seen it all through these three ventures. What advice would you give to businesses that are either in the midst of it right now or just starting up a new company?

Jamie Shulman: I can start with a couple thoughts.

One thing I'd say—which we've touched on—is: remember that people are everything. Whether it's your co-founders—like Lior or Jamie and I—whether it’s your colleagues, the people you're hiring, your customers, across the board... just keep in mind that people are very, very important.

It's a fun thing to say—especially in today’s environment with AI taking over so many conversations—but people are the differentiator. We’re real people solving real problems for real people. That would be one.

Alongside that, I’d add: integrity. You only get one reputation in life. So when you’re thinking about people—work with people of high integrity. That jumps to mind immediately.

The only other thing I’d add—just reflecting back—is being intentional, Mike.

The idea of prioritizing and focusing on the right things is something I personally struggle with, and I’m still working through it. It's a marathon, not a sprint. So you're trying to be intentional about what you’re working on, and prioritize accordingly.

And that applies broadly in life too, not just business. In life, you’ve got family, work, health—so many things. So I’d say: focus and get prioritization right.

Those would be my two things:

People are everything.

Be intentional with your focus.

Jamie McDonald: Yeah. I mean, Jamie and I spend a lot of time talking to young entrepreneurs and like, you know, kids graduating uni now and like our own kids. I guess my advice, like if you're, if you've got the entrepreneurial kind of bug, is just like, I think our ethos of like two North stars—that build amazing customer experiences and build great experiences for your team—are exactly right. And then, you know, the things that we didn't know when we started is like how much energy and velocity you have to bring to get from zero to one. And like, I think our greatest, um, like in hindsight, what we did that turned out to work really well for us is we just showed up every single day and did the work, right? No matter how bad it was, no matter if there's nothing to be done, we just showed up and kept going.

Jamie McDonald: And so call that tenacity, call it just keep going. Like if you are a founder and you wanna be that, it just requires—it's your job to bring energy and velocity, and it's your job to hang on. And like I was talking to Paul yesterday, and a husband just, uh, just raised money somewhere, a startup—like he's been going for like four years and just got his first kind of seed round. And he said to me during the fundraising process, like, "My strength as an entrepreneur is I just won't die. I'm like a cockroach." And so, you know, I'd say that to all the people aspiring to be a business builder. It's like, you know, just don't die. And then, you know, read Paul Graham and have fun along the way. And you're like—I think we're both always reading and trying to use the new tools, which you just have to keep doing.

Mike Pinkus: Yeah. Yeah. And look, there's no doubt resilience is something you hear over and over again. But I want to close with just saying the two of you are some of the most genuine guys I've ever met. And the word that comes to mind to me is you're both very humble. There's just a lot of humility, and given what you two have achieved—you see sometimes in startup land you're like, "Oh, that guy..." Like, you want people to be successful and everyone's cheering people on, but it's not always genuine. You're like, there’s good people, there's people that have huge egos, and you see it. But you two are just really genuine, humble guys. And that's why I'm elated that you guys have had so much success in your careers.

And A2X as a product for us has been fundamental in helping us shape an e-commerce part to ConnectCPA. And I think it's only the beginning of the problems that you guys solve and make easier. Like I said, cloud is gonna become bigger and bigger, and e-commerce is never gonna stop growing. So I'm excited for the future of what you guys are gonna do with A2X, and I hope more other people in accounting are watching this. If you haven't stumbled on A2X yet, it's how we shape our entire e-commerce function. But guys, you've given me 40 minutes of your time, and you're both very busy entrepreneurs, so I really, really appreciate you both hopping on, and thank you for doing this.

Jamie Shulman: Yeah, thanks. We appreciate you.

Jamie McDonald: Yeah, thank you, Mike. I mean, we love our collaboration with you and Lior and the team, and yeah, excited to keep building together.

Mike Pinkus: That was Jamie McDonald and Jamie Shulman. The Jamies have had incredible success throughout their careers as founders, operators, and investors. There are many lessons shared throughout our conversation; however, a few stood out.

The first one is, after selling Hubdoc in a multi-eight-figure exit, the Jamies could have stepped back and taken some time off. They could have moved into investing only and away from playing an active role in the tech company. Instead, they acquired A2X and joined in operations roles to help continue to build the business. To quote the Jamies, Shulman said, "Retirement never entered our minds." And McDonald followed it up by saying, "The only thing worse than working is not working."

The second big lesson is, when people see big exits and multiple built businesses, they can easily assume these guys are just lucky. But after hearing about the technology challenges, constant problem-solving, and firefighting, it's clear that it was resilience that helped the Jamies get through difficult times. That was also coupled with a strong co-founder relationship built on mutual respect, trust, and alignment of core values that pushed them through really challenging times.

The point is, whether you succeed or fail, things are going to get tough. So it's important to work with people that you like and respect so you can weather the storms when they come your way.

That's it for today. As always, keep scaling up and breaking barriers.