Episode #16

From Challenges to Triumphs

In this episode of GrowthTales, Mike Pinkus speaks with Cassy Aite, co-founder and CEO of Hoppier, who shares the raw, real, and revealing story of how his business went from $3M in ARR to zero revenue in two weeks when COVID hit and how they clawed their way back through a bold and successful pivot. Cassy takes us behind the scenes of founding Hoppier in 2016, scaling it into a nationwide B2B snack delivery and procurement service, and then having to reinvent the business completely when remote work shattered their original model. He reflects on the emotional turmoil of layoffs, the urgency of pivoting without cash, and how accelerator programs and startup communities gave him both tactical advice and emotional resilience. Cassy also shares the critical insight that helped shape their new product direction,a poker table analogy that every founder should hear, and how they re-engineered their business into a high-margin, scalable, global rewards platform with over 1200 clients.This is a story about hard decisions, capital efficiency, team dynamics, and founder endurance. A must-listen for any entrepreneur managing change or thinking about making a bold move.
Host:
Mike Pinkus
August 15, 2024

Timestamps

00:00:57 – Meet Cassy Aite: Introduction to Hoppier’s mission and story

  • Cassy’s journey began in 2016, evolving from an office snack delivery service to a rewards platform for remote teams.
  • Mike previews the major pivot during Covid and Cassy's insights from startup incubators.
View Transcript

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: If you've ever run into adversity in your business model and are contemplating a pivot, this is an episode you cannot miss. Today, we have a really exciting guest in Cassy Aite, the CEO of Hoppier. Hoppier helps people leaders create powerful incentives and reward programs to enhance the motivation of remote teams.

Cassy's a seasoned entrepreneur, having started up back in 2016. That is the reason why his lessons and insights are so valuable, as they're rooted in experience. In this episode, Cassy and I discussed how COVID crushed Hoppier’s $3 million in ARR business, forcing them to pivot, change business models, and build the technology of the current platform you see today.

We also discussed how Cassy attributes a lot of his success to the learnings of startup incubators that have helped them along the way. That includes Startup Garage at UOttawa, Carleton University's Hatch startup program, Invest Ottawa, Ryerson DMZ, and Fresh Founders.

Finally, Cassy shares an amazing analogy to table selection in a poker game to explain the current business model at Hoppier and how they arrived at it. I really enjoyed the conversation with Cassy, and I hope you do as well.

Hey Cassy, thank you so much for joining me today on GrowthTales.

Cassy Aite: Yeah, thanks for having me. Happy to be here.

Mike Pinkus: Uh, we've known each other quite a while now, and I've got to see Hoppier’s journey from the original business and the changes that have happened over the years, and I think it's a really interesting story of how you've developed the business and improved the business over the years.

So, I guess my first question is just to ask you about the origin story of Hoppier—meaning, where did the idea come from and how did you get to where you are today?

00:02:43 – The origin: A “boring” idea that grew to $3M in ARR

  • Cassy describes how he and his brother started Hoppier to solve a simple, overlooked problem: stocking office snacks.
  • Despite doubts from others, they quickly gained customers and grew to $3M in revenue before Covid hit.
View Transcript

Cassy Aite: So, I—first, the business has changed so much over the last eight years. Um, when I first started the business, that was in 2016 with my brother, and we were just looking to make, you know, beer money. Uh, we were both working at, you know, big companies, and we saw a problem that existed that was really unsexy and underserved. And that was: who is going to deliver and stock the snacks, coffee, fruit, etc., to the office kitchen?

Something that nobody wanted to do—like, the office manager, you know, they were in charge of it, but the reality was they didn't really, you know, wanna do that. And I remember when we first started the business, a lot of people, when we told them, "Hey, this is the idea and this is what we're working on," um, you know, they were like, "That's a boring, dumb idea," and, "You're never gonna succeed."

Cassy Aite: And, um, it's funny because then, when they asked us, "Well, like, how's it going? Do you have customers?"—we had customers in the first month of starting that business. And that's how we validated the idea: it was just, "Hey, can we, you know, sell to a customer?" And yeah, within a year, we basically got to something like $20–30K in monthly revenue.

Of course, that was a low-margin business. We were making 20–30% margin. But the business evolved over time. From 2016 to 2020, we grew that business to over 300 clients. We were doing about $3 million in annual revenue, 20–30% margin.

We had warehouses in Ottawa, Montreal, Toronto, Vancouver. And we eventually built a software solution that was procurement software for offices—so facilities teams could manage everything from the purchasing of snacks, coffee, fruit, office supplies, equipment.

00:04:47 – COVID-19 hits: $250K/month to $0 in 2 weeks

  • Hoppier’s business model collapsed as offices closed, forcing the team to completely rethink their strategy.
  • Recognizing shifts in labor and remote work trends, they brainstormed new ways to support distributed teams.
View Transcript

Cassy Aite: We built a Slack chatbot that employees could talk to and make requests to. And then, when COVID happened, suddenly we went from doing about $250,000 a month in revenue to zero in a matter of two weeks.

Because our business model was: you just purchased through a platform, and we make the money on the product that's sold through the platform. There's no contracts, no minimums, whatever—it's just what you purchase through the platform. We take a 20–30% cut on that, and that's fixed into the price.

And so, when that happened in 2020, we were just scrambling, and we had to figure out what we were gonna do to change the business.

We saw an opportunity with a big shift in consumer behavior, which was the shift to outsourcing labor, outsourcing talent, finding people in different places around the world, and also remote work and hybrid work.

00:05:51 – Early pivot attempt: Visa card stipends for remote workers

  • The initial post-Covid idea was a stipend card for home office setups, but the market didn’t fully embrace it.
  • With little cash and limited time, they continued iterating until they found traction with rewards and incentives.
View Transcript

Cassy Aite: And so we came up with this idea of, "Hey, it's really difficult to give budgets to your employees, so how can we make it easy to facilitate that?"

We came up with this idea of, "Hey, you could send a prepaid Visa card to your employees. They can use that prepaid Visa card to give their employees a budget."

The problem was, at the time, the positioning—I think—was wrong, because, or at least, you know, we never found product-market fit in the way that we positioned it.

We said, "Hey, this is a card for stipends—give your employees a budget to spend on home internet, their laptop, their home work setup, right, health and wellness, etc."

But, I don't know, maybe there was a business there.

00:06:50 – Final pivot to rewards & incentives: Finding product-market fit

  • After struggling with the stipend positioning, Hoppier shifted to rewards and incentives, where they finally found strong product-market fit.
  • This pivot led to rapid growth, attracting over 1,200 customers, including multiple Fortune 500 companies.
View Transcript

Cassy Aite: We just weren’t that patient because we didn’t have cash. Like, we were just—we had to make something work.

Anyway, we ended up changing the positioning. We found the right positioning around rewards and incentives after a year and a half, two years. And today, the business is in the best place it’s ever been. We have about 1,200+ customers, including, you know, dozens of Fortune 500 companies that use Hoppier.

And yeah, it’s never—it’s never been better, but definitely, like, tons of ups and downs along the way. And even today, like, we still have problems all the time and challenges all the time.

Mike Pinkus: I can imagine. But it sounds like the big shift here was you went from, as you mentioned, a low gross margin business to a high gross margin business. What was eating up your margin in the original version of Hoppier? Like, where was all this labor coming from?

Cassy Aite: So it was, number one, just product, right? So like, you know, uh, you sell—let’s say you sell notebooks, right? You sell notebooks for $10 maybe, you know, you make $5 on that. And then you factor in labor, and even costs like payment processing, things like that, that we just build into the margin—you end up with, you know, 20–30%.

Mike Pinkus: Right. So you had the product—okay, so you were controlling when people were making the purchases. Effectively, you would purchase from the supply, you had the supplier relationships, and—no different than like an e-commerce business—half of it’s gone, related to the product already, of your margin.

Cassy Aite: Exactly. It was basically, you know, just B2B e-commerce, effectively.

Mike Pinkus: Wow. And the technology side—so, building technology is obviously very expensive. So I wanted to ask you: how were you funding things at the onset, and to just build out these platform capabilities as you pivoted into a rewards platform-type technology?

How did you pay for all this? What was the path back then, and what was the plan once you went through the pivot? Because as you mentioned, you’re running outta cash and you had to move quickly.

00:09:16 – How a strong team enabled fast pivots

  • Cassy credits the team's long-standing collaboration and trust as key to quickly building and adapting new technology during the pivot.
  • Their ability to operate efficiently under pressure was rooted in having worked together for four years prior to Covid.
View Transcript

Cassy Aite: Yeah, so I think we were lucky that—number one—we had a really great team that had been working together for a long time. And so we were able to build technology quickly. Even when we built the procurement system, we built it on a very tight budget and were able to make the most of it because I think we had such a solid team.

And that stayed true even at the time. I realized after that a huge advantage was the fact that our team had been working together for four years before that. So to be able to quickly pivot—I don't think we would've been able to do that otherwise. Just the fact that we were working together like that.

But we did raise some money. We raised about one and a half million in debt along the way. And we've also done about $1.5 million in dilutive funding with angels.

Mike Pinkus: Mm-hmm. And you're part of some startup communities as well, correct?

00:10:19 – The role of startup incubators in survival and success

  • Cassy credits programs like UOttawa’s Startup Garage, Carleton’s Hatch, DMZ, and Fresh Founders with mentorship and community.
  • Though funding was minimal, access to advice and connections proved invaluable.
View Transcript

Cassy Aite: Yep. Oh yeah, definitely. They've been a huge help to us along the way—everything from UOttawa’s Startup Garage Program. I'm an alumni of Ottawa, and we did the Startup Garage program in the early days as alumni. That was super helpful—not just with the funding they helped with, which was only small, I think at the time it was like $5K to $10K—but it went a really long way.

At the time, $5K to $10K felt like the world to us, right?

Carleton University, their Hatch startup program—my brother went to school there—so they had some programming that they helped us with. Invest Ottawa has been super helpful. The Ryerson DMZ—we did a summer at the DMZ in their startup program there, their Scale Up program, when we were maybe like two or three years in.

Cassy Aite: Originally, the idea was, “Hey, let’s get some office space in Toronto,” because we had some people there. But it ended up being way more than office space. There was no funding, and there was no equity component—we weren’t giving away equity as part of this accelerator—but they gave us amazing access to mentors and a community that was super valuable.

And then the last one I’ll give a shout-out to is Fresh Founders. That’s been super helpful, and I’ve connected with so many entrepreneurs there that have done so many amazing things.

Mike Pinkus: And are all these mentors and accelerators, Cassy—did that help you reframe the business model? Because you made quite a pivot. I mean, going from a business that’s selling product to going to a platform or like an experience for rewards for B2B—that’s a big risk.

Meaning that it might be harder to attract revenue, you’re going to have competition, and technology obviously has other challenges that are quite unique.

Did having access to those mentors help you get to that decision? Or did you already know because of COVID that that was the path? Like, in your mind, did you know that that was the path you were going down, and you just needed clarification on how to get there?

00:12:47 – Reframing the business model with mentor guidance

  • Talking with other founders facing similar struggles helped normalize their situation and guide next steps.
  • Startup communities gave emotional and strategic support, reinforcing resilience.
View Transcript

Cassy Aite: Yeah, and I mean, when you're backed against the wall, you have no choice, right? It was either go bankrupt and, you know, the business is dead—or figure something out.

And, um, we’re lucky because through Fresh Founders and some of these other groups, I talk to peers—a lot of peers who are not just first-time founders—and I tell them, “Hey, this is what we're going through,” and they’d have their own stories.

Dozens—I heard dozens of stories where people went through very similar things, whether they were restructurings, or, you know, the business almost failing and going bankrupt, or getting killed by a competitor or by some Black Swan event.

So that really helped: to know that we’re not alone, and to be given advice on, “Here are some of the things that you can do,” or just to know that some of the things we were doing were on the right path of thinking.

Mike Pinkus: Yeah, it’s amazing. And the current Hoppier—in its current state—and first of all, congrats on making a successful pivot because, as I mentioned, it’s obviously littered with challenges.

What is the revenue model now under the current Hoppier, where you do have the higher gross margins? How do you generate revenue now out of the rewards?

00:14:18 – Today’s model: Global digital rewards via flat-fee software

  • Hoppier now provides a simple, global solution for sending prepaid Visa and gift cards in 60+ countries.
  • The pricing model is transparent—no hidden fees, just a flat software charge.
View Transcript

Cassy Aite: Yeah. So today, what Hoppier is—we make it incredibly easy to send prepaid Visa cards and gift cards to your employees or clients in over 60 different countries.

So it’s software. The way that we make money is really simple. We charge just a software fee to use the software and to send these prepaid Visa cards and gift cards around the world.

And we make it incredibly easy to just understand the pricing, because that was one thing in our space—a lot of people were charging a percentage of the funds that you send. Or, you know, you go, you want to send a gift card and you go activate it, and there’s an activation fee, and all these other fees that you never really would think of, right?

So we make it really easy and just charge a flat software fee.

Mike Pinkus: And your UI experience—and I know you showed it on your website—is really innovative. How did you come up with the idea? Like, the minute you get onto your site and start reading the copy, you highlight a use case that I’ve seen so many times, which is: whether it’s a gift, a gift card, or a Starbucks card, you give it to someone, they use it twice, throw it in a drawer, and lose the remaining balance.

But you’ve created an interface that allows the company to control the spend. So if you give a budget to a manager and they spend $600, the remaining $400 isn’t just lost in a drawer. 

How did you come up with that as being one of the pain points? And how did you go about solving that—for companies, as well as employees and people?

Cassy Aite: Yeah, I think it was just talking to customers over time and understanding. It was really just that simple. I think it’s listening to them, hearing the same thing over and over again—what’s a pain?

And we had the problem ourselves. Like, we had a team of 28 people at our peak—26, something like that—and people all across Canada. We had contractors around the world. So, we knew the problem pretty well ourselves.

So creating features within the product that make it really easy, and understanding the unique selling points—like:

"Hey, you get all of the unused funds back that you don’t spend."

"Hey, with one simple link, you can send this to a hundred people and you don’t have to send it out individually to each person."

Or, "You can upload a list with a CSV file, and then you have your list of people within the app."

Those little things were just from experience and talking to customers.

Mike Pinkus: And you mentioned there you had 28 people—not to bounce back to the changes—but what goes right into my mind is the HR nightmare of a pivot.

As you mentioned, going through COVID, having 28 people on the team—how did you sort out just the change in headcount and the plan around that?

How did that all unfold?

00:17:55 – Cutting 70% of the team: Emotional toll vs. survival

  • Cassy shares the difficulty of laying off friends and long-time colleagues, emphasizing how emotionally challenging the decision was.
  • Despite the pain, it was a necessary move to ensure the company’s survival and refocus on roles essential to the new business model.
View Transcript

Cassy Aite: It was pretty tough. I think, you know, especially because a lot of these people became, you know, they were friends or, you know...

They became friends over time. Um, but we– we just, you know, it was like survival mode, right? It's either, hey, either we reduce the team to 10 or–

We go out of business. And– and then it was just a matter of looking at, you know, what are the– what are the critical roles in this new phase that the business that we're– we're building, right? Like, you know, a lot of people, it was just clear because we were changing the business. So all of a sudden, we didn't need a lot of the operations people that were managing the, you know, the operations of whether it was buying product or, um, you know, we– we did have warehouses too, so, you know, the warehouse staff and, um– and yeah, so some of it was– was kind of obvious, but, um, we did cut– we ended up cutting pretty deep. And, uh, and it wasn't hard to– it wasn't– it wasn't easy to make a lot of those decisions, but, um, it was just a matter of saying, hey, you know, who can take on additional work here and there? And–

You know, what's the 80/20? Like, what's the 80– you know, the 20% of things that we do that drive those 80% of results? Um, and that took, like, looking at– like, looking at the business and looking at data and making data-informed decisions too.

Mike Pinkus: What– what's incredible about that is, um, you hear in the news of, like, Elon Musk going in, getting rid of 80% of, uh– uh, Twitter, and that's done strategically and intentionally and whatever it might be. Cassy, in– in the situation of Hoppier, you're obviously very, very different circumstances, meaning back against the wall, like literally between a rock and a hard place and not really much choice of, like– like you said, it's imminent death or– or– or structural change in the business. And– and that's like, because I'm on the other side of the fence where I see lots of businesses, it's a more common thing than people think, where you're just put in really, really, uh, complicated situations. How is it now with a smaller team, running culture and managing team? Is it easier with a lower headcount? Or is it just different challenges?

00:20:13 – Running a 5-person team: Why lean is better

  • With fewer people, they operate faster and more nimbly, making decisions and executing quickly.
  • Cassy challenges the perception that a larger team equates to success, noting people complexity as a major challenge.
View Transcript

Cassy Aite: So I would say it's like– it's a hundred– it's way easier. It's way easier. And, um, you know, I used to like– I'll go to family gatherings and– and, you know, go to like, you know, family gathering and people– people ask me, "Oh, Cassy, how's the business going?" And I'll say, "Oh, it's pretty good, you know. We had a good year last year, but we're trying to figure out this thing," you know, kind of short. I– I keep it kind of short. But then, you know, the– the next follow-up question is always, "Well, how big is the team now?" And it's like, that is– a lot of people, that is like success. And to me too, like maybe subconsciously, I used to think, hey, having a big team is sexy. It's cool. It's, you know...

Cassy Aite: But you know, this– like, having, you know, people, we're– we're like warm robots, right? We're not– we're not programmable robots that can just robot, you know, go and– and do what we're told, you know, 12 hours a day and just do the same thing over and over again. I mean, people are really challenging. Like, that's the hardest aspect of any business, I think, is people. And it's like communicating. It's working together. It's working on the right thing. It's dealing with conflict and all those things. Like, removing that, um, you can move way faster. And so today, you know, we're only– we're– we're five people, and we're able to achieve as much or– and even maybe in a, you know, faster timeframe than we could when we were like 20-something. Just because it's so much easier just to– to go and say, "Hey, we're gonna do this. Let's test it. Let's do it tomorrow." And boom, it's– it's done.

Mike Pinkus: It's– I love the way you frame that too, because I– I see it all the time. When did it become sexy to be the, "How big's your team? How much did you raise?" Like– like...

Cassy Aite: Do you get that question too? Like when you go to family gatherings, you're like, you know, you've got an– an uncle that's going, "Hey, Mike, how– how big's the team now?"

Mike Pinkus: You– you get it more from– you get it more from friends. And what's funny is when you sit on the other side of the fence, uh, Cassy, like, I share the same sentiment you do. I mean, I look at it as, um, I've always looked at capital efficiency and profitability as like the hallmarks of– of a stable business. It means you're in control. Um, it doesn't mean that there's not a place for having a big team and fundraising, and it depends on– on the type of idea and how quick you're moving and a whole host of variables. But it's bizarre how it just became a thing that those are the questions: "How big's your team? How much have you raised?" And for some reason, there's, uh, like an aura around that. However, I am now noticing, uh, a flip in that. I think the– like, because the markets have kind of changed, you see more people asking about, "Are you profitable?" or–

mm-hmm.

"Are you still burning?" Uh, and the team size question is now shifted quite a bit as well, where people are realizing unit economics matter a lot. And, uh, and so I have seen a shift from those heydays of 2000–2021. Things have changed quite a bit. At least I've seen it. I don't know if you've noticed that.

Cassy Aite: Yeah, a little bit. I'm hearing more people talk about, uh, rev. I mean, I think it's like the indie-preneur thing, right? Like, a lot of people are talking about– they see people like Peter on Twitter and they go, "Oh, how do–" uh, you know, "with a one-person business or $10 million with a one-person business," right?

Mike Pinkus: Right.

Cassy Aite: More people are talking about revenue per employee. But– but yeah, I've noticed it too, for sure. But I don't know. I feel like what are the– it teeter-totters like this, you know? People– it's– it's a hard thing to do and to stay focused on.

Mike Pinkus: I would agree with that. And– and like I said, every situation is unique, meaning there is a time and a place where a business can't reach its full potential without– without additional capital, whether it be VC or PE. Um, and there's also situations where having a really big team does accelerate growth. However, um, it– it used to be those two things at all costs. And I think for sure that's– I've noticed a change. What are the challenges you're seeing? I'm curious about what– what are the challenges you're seeing now? Now you have a smaller team, you said it's easier, but you mentioned at the beginning of the– of the– of the conversation that there's still tons of challenges. What are those challenges today where you have the higher gross margin, you have the smaller team, Cassy, where are the problems coming from today?

00:24:54 – Current challenges: SEO, positioning, and strategic growth

  • Cassy’s focus has shifted from survival to forward-thinking: positioning, market cycle, and competitive landscape.
  • They rely heavily on SEO and are watching trends like Google updates and AI’s impact on discovery.
View Transcript

Cassy Aite: Yeah, I would say, I mean, they're like common things. Like, you see, I– I would say some of the challenges are like probably around go-to-market the most, right? Like, we get most of our customers through our blog and, um, I mean, there are tons of Google updates happening. People are saying SEO is dead. AI is gonna– AI search is replacing Google. And– but, um, and like that, we're seeing that a little bit, but, uh, but I don't know, just things like that.

Like, I think thinking of the future, I– I think the benefit that we have now is we're able to think so much further in the future of the business instead of thinking of just tomorrow, like, how do we make– make the next buck? And, uh, and so a lot of the– the challenges we're thinking of are for, like, long term, um, and– and also like very strategic. So whether it's like, is the positioning still right today? Where are we at in the cycle of the market? How– you know, what's the market like? What are the competitors like? Like, where do we need to be? How do we need to position ourselves? Um, and those are like the– yeah, those are the challenges I'm dealing with now more.

Mike Pinkus: And are– is the fire rate– and when I say fire rate, like, I mean like fires that are burning, problems that are happening– is the rate at which things are that you have to deal with, are urgent, is that gone way down from– from the old model?

00:26:23 – Operating without constant fires: Shift from chaos to clarity

  • The intensity of daily emergencies has dropped significantly since moving to a SaaS model.
  • Their previous business was capital intensive with inventory, net terms, and operational headaches.
View Transcript

Cassy Aite: Yeah, a hundred percent. A hundred percent. I think the–

Mike Pinkus: That because you were–

Cassy Aite: Yeah, go ahead.

Mike Pinkus: No, sorry, go ahead.

Cassy Aite: Oh, I was– I was just gonna say like, it's– it, yeah, the nature– I think I know where you were going with it. Like, the nature of the business, um, you know, having the physical aspect I think was definitely–

Mike Pinkus: mm-hmm.

Cassy Aite: Right? Like, um, it was a very tough business. It was very capital intensive, the business before. Cap– so capital intensive because we'd have to pay for product upfront. Um, then eventually we'd, you know, we'd– we'd get paid by– and a lot of the customers wanted to pay on net terms. So they'd pay– they'd– they'd wanna pay net 30, net 60. In some cases, we would pay for the product upfront. We'd pay on a credit card. And so, you know, it would be– we– we had– we– and it was almost impossible to achieve a negative cash cycle in that business, um, because we were a small fish not purchasing that much at the end of the day or running that much volume.

I mean, $3 million of product purchase is not a lot in the world of e-commerce. So, um– so yeah, so it was, um– and then the people aspect was really tough too, right? Like, we have all kinds of stories of, um, you know, just people challenges, right?

mm-hmm.

Like– like crazy stuff that would happen. Like, we had all kinds of stories of– of, you know, just challenges that– that would happen. Um, so– so yeah, that was a– that was a– a tough business. Now it's– it's a lot easier, um, for sure, the type of business that we're running because it's, you know, pure software there. But even still, like, you know, you have, uh, with 1,200 customers now and hundreds of thousands of people receiving prepaid Visa cards and gift cards, you get– you know, there are bugs that happen. There are edge cases, weird edge cases, all kinds of things that might happen when you have that many people using the software on a– a daily or a monthly basis.

Mike Pinkus: Do you ever think to yourself, what would've happened if there was no COVID? Would you have gone to 6 million, 10 million and not– not– and 'cause your back wouldn't have been against the wall?

00:28:39 – What if COVID hadn’t happened? The blessing in disguise

  • Without the crisis, Hoppier may have scaled the original model—but likely with more stress and lower valuation.
  • The pivot revealed better economics, better exit potential, and a more sustainable, scalable business.
View Transcript

Cassy Aite: Yeah. You know, like we– we were running– the problem was with that– with that business is we didn't understand. So, okay, so people talk about this concept. I've heard this concept before. It's like the poker– picking your– your business is picking– and we talked about this before, like you're a big–

Mike Pinkus: mm-hmm.

Cassy Aite: You love poker.

Mike Pinkus: mm-hmm.

Cassy Aite: Right? And– and so, um, like picking the– the business or the, you know, picking the– the right business is like picking the– the right poker table to sit at. That's the most important aspect of playing poker if you wanna win money is, "Hey, what– what's the table that you're sitting at? Who are the other players that are there? What's the," you know...

And– and maybe not in business, it's not necessarily all about the players that are there, but just what's the game that you're playing? What's the– the product you're selling, the space that you're in, the competitors in the space?

00:29:31 – The poker table analogy: Picking the right business model

  • In 2019, Hoppier received acquisition interest but realized their old model wouldn’t fetch strong offers.
  • The low-margin, operationally heavy nature of the business reduced its attractiveness to buyers.
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Cassy Aite: Um, and so like, the poker table that we were sitting at before was just really tough. And, um, you know, I think– I think like, yes, we probably would've grown a lot, but, um, you know, that business, again, it was like capital intensive at the end of the day. Like, you could– you could say $10 million in revenue in that business is– valued at the same as $1 million in–The new business. Because not only is the– the margin, you know, that margin has the impact 'cause you're only making 20% margin, it's also harder to run. You're probably working way more hours and have to deal with way more headaches in the other business, um, in the previous business, versus the new business where, you know, practically runs itself in a lot of ways. And then on top of that, from an exit opportunity perspective, like, the multiple on the new business– somebody is going to be willing to pay way more for the new business than the previous business.

Cassy Aite: And with the previous business, we had offers to buy the business, and that was around 2019, and that's when I was kind of woken up to– I was like, "Oh, shit, this business is maybe like– the exit opportunities aren't as good as I thought they were." Because I– I had this– I had two people that– two or three companies, and they were really big and they had the money to buy the business. But when I talked to them and they were like, "Yeah, we're interested in buying you guys," I was like, "Well, what– you know, it's not for sale, but what are you thinking?" And they'd go, "Well, maybe I'd give you like, multiple on your EBITDA this," or– I was like, "Oh, we're not even, you know, profitable. Like, there's no EBITDA." It wasn't even– they weren't even willing to give us a– a multiple on revenue, right? So that was, um– yeah, that was a really– it was just the– the poker table that we were sitting at. Really tough poker table.

Mike Pinkus: And so it seems like this was– this was independent of COVID, meaning like COVID forced you to take action–

But it sounds like you knew what the right thing to do was, but like, it's almost a blessing that you kind of just had a gun to your head to go do it. Like, so you do think you would've inevitably made that decision, just potentially a little bit later?

00:31:57 – Bootstrapping vs. fundraising: Two different wealth paths

  • Cassy contrasts his high-growth, VC-backed journey with that of a friend who built a slower, bootstrapped business generating steady personal income.
  • He reflects that while both paths can lead to success, each requires a different mindset, pace, and long-term vision.
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Cassy Aite: I think my life would be very different. Like, we would, um– yeah, just be very different. Um, but yeah, like, don't get me wrong, I do think it could be a great business. Like we– you know, one of the wealthiest people I know ran a– an office coffee business that was doing $30 million a year in–Quebec. And now, um, you know, they– I think they're pulling a couple million dollars a year out of that business for a very long time. But they ran it very differently than the way that we ran the business before. We were growth at all costs, whereas he ran his business slow and steady over the course of 30–40 years.

Mike Pinkus: Different– different economics. And I– I– I don't wanna hold you too long, Cassy. I know we're a little bit over here, but I wanna ask you one last question I ask everyone. Any advice for other entrepreneurs that are– that are on the journey? One or two things you'd give if someone's starting out right now? You talked about the poker table. I think that's a great piece of advice to be at the right table. Um, but anything else you'd give as advice to newer entrepreneurs or people and fresh founders or other communities?

00:33:08 – Final advice: Build what you wish existed and validate it fast

  • Cassy encourages entrepreneurs to solve problems they personally care about—it creates natural alignment and drive.
  • He stresses launching quickly, validating with real customers, and not over-investing in software before traction.
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Cassy Aite: Yeah, I think the– the– the point on like, pick the– when you're picking that poker table, like, yes, I wouldn't overanalyze it too much because I think at the end of the day, you really should think about what is something that you wish existed, because that'll make it so much easier to build a great business. And, um, that's what I– I would focus on more. And then, you know, out of all of those different– those different ideas that you have, um, you know, then– then you can start to think about the poker table. But I– I would focus on, you know, when you're just getting started, I would just build something that you wish existed and then go get paying customers as soon as possible.

You don't need to build a fancy app. I mean, with, uh, Hoppier, like the previous– you know, before when we first started the business, we got to like a million dollars in revenue before we ever built any software for– on the procurement side.

Mike Pinkus: Yeah, that's a great lesson. 'Cause everybody's waiting, waiting, waiting, waiting. And then you– you could build for three years and realize that there's no market for what you just built. And that's a dangerous game to play as well. And I think people are more aware of that today, but the mistake is probably made over and over again. 'Cause you don't want to– you don't wanna ship something that isn't perfect, right? And so–

Cassy Aite: Yeah. You know how– I mean, you know how expensive it is to build software and how time consuming it can be, right?

Mike Pinkus: mm-hmm.

Cassy Aite: Yeah.

Mike Pinkus: So Cassy, uh, thank you again for joining, and– and congrats again on– on these changes you've made and– and where you've taken the business, because I think, uh, you make it seem like you just figured it out and it was just figuring out the 80/20 rule, but I'd imagine in the moment it was probably extremely stressful. And– and you guys have done a really good job of like product placement and like– like if someone who didn't know anything about you came to the Hoppier site, they'd right away know what the value, uh, proposition was. So thanks– thanks again for taking the time and– and congrats on what you've done.

Cassy Aite: Yeah, thanks. Thanks for having me on the– on the show. It's cool. Great to chat.

00:35:28 – Recap and final thoughts

  • Mike summarizes key lessons from Cassy’s journey: making hard decisions during crises, and strategically pivoting to a more sustainable business model.
  • The analogy of poker table selection reinforces the value of choosing the right business environment to maximize long-term success.
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Mike Pinkus: That was Cassy Aite, CEO of Hoppier. Cassy started Hoppier all the way back in 2016 and has seen a lot over the last eight years.

Here are the main takeaways from the conversation:

Number one: Cassy faced a critical point where the business was going to die during COVID. If he didn't change the business model, his choice was to cut the majority of his 28-person team or let the business go under. From the outside looking in, the answer would appear obvious. However, this team had built a $3 million in ARR business together as friends, colleagues, and instilled a great culture. The lesson is, the right decision is sometimes the one that feels the hardest. No one wants to let go of the people they like and care about, but if the alternative is the business dying, you may have to make the most difficult choice of your life.

Number two: Cassy makes an amazing analogy to playing poker when explaining the business model pivot. In poker, the most important determinant of your success is table selection. If you're the 10th best poker player in the world and you sit down at a table with nine players who are better than you, you might get crushed. Cassy explained how Hoppier’s pivot is analogous to the poker table seat selection. The original business model had low margins, required a large team, and was difficult to operate. By reducing the team size to only a handful of people and building technology to allow for higher margins, Cassy improved his chances for success. Whereas he would put it, he's now sitting at the poker table where he's the strongest player.

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

Meet Our Host

Mike Pinkus

Co-Founder: ConnectCPA
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Meet Our Guest(s)

Cassy Aite

CEO of Hoppier
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