This Entrepreneur Sold A Company For $450 Million And Is Now Building A Payments-As-A-Service (PaaS) Platform For Vertical Software Companies
Founders like Joshua Silver are the architects of multiple companies, each bigger, more innovative, and more strategically positioned than the last. His entrepreneurial pathway traces his early days as a tinkerer and engineer to a $450M exit in healthcare payments.
Joshua is now scaling Rainforest, his latest venture, into one of the most promising embedded payments platforms in the US, demonstrating a founder record that reads like a masterclass in timing, incentives, and grit.
In this conversation, Joshua unpacked the lessons learned from launching companies in highly regulated sectors, bootstrapping against industry norms, navigating exits, transitioning into strategic consulting, and analyzing market demand.
And then, returning to build again in a larger, faster-growing category. Joshua also talks about how he leveraged consulting as a bridge to his next business, the challenges he faced, and how AI has reshaped companies' operational structures today.
Growing Up: From Atlanta Techie to Georgia Tech Engineer
Joshua was born in Boston but grew up in Atlanta, where curiosity and tinkering weren’t hobbies; they were instincts. Robotics, K’Nex, Legos, anything he could build or rewire, he did. By the time he reached Georgia Tech, his future was already forming.
Joshua chose computer science, laying the foundation for two decades of fintech development. But upon graduation, he faced the crossroads familiar to many ambitious engineers: go corporate or take the leap?
Most parents expect their kids to “get some experience first.” Joshua’s parents were no different. He did get offers from some of the top consulting firms and major technology companies at the time. He could have taken the traditional path and worked for someone. Instead, he started his own thing.
Joshua saw the timing advantage. He had no expenses, no family commitments, and he was at a relatively low-risk time in his life. In his words, “If it didn’t work out, I could always go back to corporate America.” It did work out—and spectacularly.
Patientco: The First Big Leap
Joshua’s first venture was Patientco, a healthcare payments business he co-founded with a fellow Georgia Tech alum, Bird Blitch. They split responsibilities down the middle. Joshua took over product, engineering, and operations, while Bird handled go-to-market and sales.
Together, the duo did what great startup teams do--they searched for the right problem. But unlike the typical founder narrative of “I suffered this problem personally,” they approached it as engineers. They analyzed market trends, real pain points, and how they could generate revenue for stakeholders.
Joshua stresses that this has always been the recurring theme of his business career--how to help a company make money. In his view, it’s not about time savings or efficiency. When you help a company make money, it becomes a must-have product.
This approach led Joshua and Bird into healthcare payments, where the initial idea was simple--to digitize patient billing. This was in the mid-2000s, when hospitals and doctors’ offices didn’t offer online bill pay. The duo set about solving the problem of making payments.
Back then, all healthcare payments were made by check. Initially, the duo considered electronic payments. But once they dove deeper, they found the real problem wasn’t “electronification.” It was “collectability.” Hospitals were collecting 50 cents on the dollar for every patient bill they sent out.
Imagine a grocery store where every second customer just walked out without paying. Prices would double. That’s essentially what was happening in U.S. healthcare. That insight led them to tackle the core pain: helping hospitals increase revenue.
Early Execution in a Regulatory Nightmare
Joshua and Bird quickly realized that Patientco was at the intersection of two of the most regulated industries--financial services and healthcare IT. They also had to factor in PCI compliance and HIPAA compliance. Aligning all these concerns was highly challenging.
The duo found that you can’t hack together an MVP and see what happens. There's really no room for error when you're moving people's money and dealing with healthcare data. Convincing customers and then getting them to be the first adopters in highly regulated industries was an uphill task.
Joshua described Patientco’s early trajectory as “wedging our way in.” They moved from small physician practices to rural clinics, to regional hospitals, and eventually to systems comprising 25 to 30 major hospitals and thousands of doctors.
By the time the duo exited Patientco, they were working with some of the largest healthcare organizations in the country, including BJC Healthcare in St. Louis and Piedmont in Atlanta.
The Revenue Model: Alignment, Always
Patientco’s revenue model was simple but powerful. They only got paid when customers did. Hospitals were leaving 50% of billings on the table. Patientco helped them recover the revenue and took a share of the incremental collections.
The principle was simple. Patientco aligned incentives between the company and its clients.
Bootstrapping to $1M ARR Before Raising a Dime
In an era where founders raise money on day one, Joshua and Bird did the opposite. They contributed personal working capital, were financed by customers, and requested prepayments. They focused relentlessly on positive cash cycles.
They reached $1M in ARR before raising outside capital. Only then did they raise ~$4M early on, but remained lean throughout. Eventually, they raised ~$27M in a series B round from a growth equity firm before exiting. For $450M.
As Joshua points out, coming right out of school, building the business, and $450M for the first rodeo as an entrepreneur was phenomenal. Although luck played an important part, it was also about being in the right place at the right time.
The ultimate ingredient for that company was an idea that addressed real pain points for patients and health systems. Secondly, the cofounders ran lean operations until they were ready to scale. From start to exit, the company took about 13 years to build.
Looking back, Joshua concedes that they started the company too early. The graph was initially flat because the market was not ready for their product, which was more mature than their competitors'. Further, it took Joshua and Bird time to build the product and identify the product-market fit.
They worked through sheer grit to weather those slow years until the market was ready and they had a truly stable, scalable solution. And then the last few years were just about extremely rapid growth. To sum up the entire experience in Joshua’s words,
Success is about “Making sure you're building in a good market where the trend is going in the right direction, having enough capital and enough patience to stick with it even through the slow times, and making sure that you get to the point where you can grow quickly and build a quality solution.”
When Great Companies Get Bought: The $450M Exit
Patientco sold for $450M. As the acquirer noted, unlike competing companies, Patientco's software was exceptional in build quality, a core value. As Joshua points out, when creating something in healthcare or finance, it must work 100% of the time without risking anyone’s money or healthcare data.
This core value earned the cofounders a fantastic multiple at the height of the market in 2021. Joshua firmly believes that great companies are bought, not sold. The cofounders never set out to sell the company specifically, but were considering collaborations over time.
Joshua and Bird focused on positioning the company with a strong customer base, revenue quality, organized documentation, and robust financials — all of which make a significant difference. In short, they had been poised to sell for the past 13 years.
The acquiring company, a private equity firm, later rolled Patientco into Waystar, now a NASDAQ-listed health payments platform valued at roughly $6.4B. Today, Joshua still receives healthcare bills powered by software he helped build 20 years ago. In his words: “That’s really rewarding.”
Joshua considers it the best possible outcome. The exit generated significant financial returns for employees, shareholders, and the founding team. The product continues to perform and is scaling, which is great for the acquirer as well.
Going from Exit to Consulting
Joshua didn’t plan to consult. He planned a break. That lasted one or two weeks. Private equity firms, vertical SaaS CEOs, and portfolio operators regularly sought his help with payment strategy, due diligence, risk management, and contract renegotiations.
Over 3 to 4 years, Joshua completed ~50 engagements, having spun out a full consulting firm, the LaunchPath Group. He remembers the stint as a “fast and furious time for embedded payments.” It was an intellectually rewarding experience and a great transition.
Joshua enjoyed working with different companies and solving problems for them. But he was ready to wind down the consulting firm and focus on a mission with greater longevity--embedded payments. As he explains, it's when a software company offers payment processing as part of its core services.
The Second Act: Rainforest
Joshua cites the Toast POS example. When customers visit a restaurant, they use Toast POS to make payments. Toast processes the payment, but previously, servers would ring the order and use a separate credit card terminal provided by their bank. The payments and software were different.
Embedded payments are when you integrate software and payments. And, the concept was exploding. Joshua noted that although it had a huge market, vendors were entirely dissatisfied. These vendors included legacy, scaled incumbents such as Global Payments, WorldPay, and TSYS.
Aside from these huge payment processors, new companies were emerging on the scene, like Adyen and Stripe. Joshua quickly identified the problem. The market had rapidly scaled, and payments were an integral service that enabled people to make money.
The most crucial factor? There were huge levels of dissatisfaction. Joshua saw a great business idea here. Around four and a half years ago, he had decided he was going to start an embedded payments company, and the time was right.
Joshua assembled a team of 10 from previous companies, including people he had worked with for 15 years. And, Rainforest was born. Its business model involved working with software companies.
The Rainforest Model: Shared Incentives, Again
Rainforest partners with software companies to help them generate more revenue. As Joshua points out, best-in-class software companies that, say, earn $10M in ARR, can double the size of their business to $20M in ARR.
These companies can have a 50-50 split between payments and software. Rainforest helps them generate more revenue and takes a piece of every transaction, thus aligning its success with that of its customers. If Rainforest doesn’t deliver, it doesn’t get paid.
Having gone through a successful exit, Joshua found it easier to raise funding; however, he chose a strategic pathway to execute the raise. As with Patientco, he has maintained the lean mentality. He was confident that Rainforest would be much bigger than Patientco and its impressive exit.
Storytelling is everything that Joshua Silver was able to master. The key is capturing the essence of what you are doing in 15 to 20 slides. For a winning deck, take a look at the pitch deck template created by Peter Thiel, Silicon Valley legend (see it here) where the most critical slides are highlighted.
Remember to unlock the pitch deck template that founders worldwide are using to raise millions below.
Joshua had been incubating the Rainforest concept since his consulting days. He recognized the opportunity and was monitoring the market to launch the company at the right time. Additional advantages were that investors already understood embedded payments and were bullish on them.
They had passed on competitors and had waited for the right company to invest in. Joshua did not need to educate investors about the problem or how Rainforest was solving it. The only questions were how they were going to do it better than competitors and what the edge was.
Soon, investors were approaching Joshua proactively, unlike with Patientco, when he had to educate them on the problem and revenue model. The combination of repeat founder experience, market timing, and investor awareness culminated in successful fundraising.
The Vision: Becoming the Default Payments Partner
Joshua’s vision is for Rainforest to be the default payments provider for all vertical software companies. As he explains, there are ~10,000 vertical SaaS companies in the US alone, and double that if you include global companies. Very few of them are being serviced well today.
Joshua sees them as huge opportunities. He is excited about partnering with fantastic entrepreneurs to help them grow their businesses. He envisions making them more financially solvent and improving their revenue streams. And that’s just for starters.
Joshua foresees a time when anyone starting a company knows Rainforest is the go-to for payments. That is exceptionally rewarding for him. In the four years since the company’s inception, it has made tremendous progress and is winning deals against some of the much larger competitors.
Lessons from Two Decades of Entrepreneurship
Joshua distilled 20 years of learning into one consistent truth. A company’s success depends on getting the right people on the bus at the right time. His most significant learning is how to determine whether someone will be a good fit for his company.
Joshua understands that across different time periods and growth phases, the company will have different needs, but it’s about distilling down who is well-suited for a particular role. He asks questions like:
Is this a high-growth role? · Is this someone who's coming to build out the team? · Is this a role where you can take a flier on someone who may not have done it before and hope they figure it out? · Or is this a role in a time when you need someone who's done this 10 times, who's going to come in on day one, and know what's going on?
Hiring mistakes don’t cost months; they cost compound growth over a decade. Most founders underestimate that. Joshua says, “When you miss a quarter or two, you’re not just missing those two quarters. You're losing compounding effects for years.”
Transparency, Leadership, and Mistakes
Joshua isn’t the founder who pretends everything is perfect. On LinkedIn, he shares the mistakes his team has made, hard lessons and failures, the supply chain of learnings, and what’s working for him because building great companies isn’t mythology. Its execution.
Joshua’s success began by solving revenue-risk problems in highly regulated healthcare and by aligning incentives so customers earned more. · Patientco’s $1M bootstrapped ARR and $450M exit show that lean execution, patience, and timing beat fundraising theatrics. · Great outcomes are earned over years of execution; Patientco was “bought, not sold” because its product and financials were exceptional. · Consulting became Joshua’s bridge—a deep market pattern recognition that led directly to spotting a massive embedded payments opportunity. · Rainforest mirrors Patientco’s model: shared incentives, deep domain expertise, and disciplined capital allocation in a massive, underserved market. · In fundraising, repeat credibility and market timing flip the script—investors approach you when the pain is obvious, and the thesis is proven. · Joshua’s core principle: success compounds when you get the right people at the right time, because hiring mistakes destroy years of growth.
Original Version
Alejandro Cremades: Alrighty, hello everyone and welcome to the DealMaker Show. So today we have ah another repeated founder you know joining us. you know We're going to be talking about all the good stuff that we like to hear, obviously. you know The building, the the financing, the scaling, the exiting.
Alejandro Cremades: Also, we're going to be talking about like how you know he got started with his first company. you know They ended up having a really nice transaction there, $450 million that was saying disclosed. And then also we're going to talking about how he used consulting as the transition bridge in order to get to the next business. So again, we're going be talking to about good stuff like challenges, experiencing experiencing growth today, you know the world of AI, how that is impacting you know certain certain aspects as you're thinking about the operational you know structure of your business and other really good stuff. So brace yourself for a very impactful conversation today. Very inspiring too.
Alejandro Cremades: And without further ado, let's welcome our guest today, Joshua Silver. Welcome to the show.
Alejandro Cremades: So originally born in Boston, but grew up in Atlanta. Give us a walk through memory lane. How was life growing up for you, Joshua?
Joshua Silver: You know, it was it was good. I moved from Boston down to Atlanta when I was in middle school and then stayed in middle school, stayed in Atlanta through high school and college, went to Georgia Tech, studied computer science there. So pretty technical background by training. And that has certainly come in handy over the last almost two decades now of of building fintech companies.
Alejandro Cremades: How did you get into the world of computers to begin with?
Joshua Silver: You know, as a kid, I was just always ah always a tinker, you know, loved building things, whether it was Legos or Kinects or robotics, things like that, and just really carried that through and pretty early on figured out that Technology and engineering would make a pretty good career and I enjoyed doing it. So stuck with it, you know, starting really and in middle school all the way till now.
Alejandro Cremades: And how was that moment where you decided to go at it as an entrepreneur? Because, I mean, it took no time right out of college. And I'm sure that your parents were probably like, hey, hey Joshua, why don't you do a few years at least of corporate?
Joshua Silver: You know, it was ah ah a big kind of existential debate I was having when I graduated from school, I had offers from a lot of the top consulting firms, some of the the major technology companies at the time, um and you know really had to figure out what I wanted to do with my life, whether I wanted to go more of a traditional path and go work for someone or start my own thing. And ultimately, of course, decided to go down the path of entrepreneurship.
Joshua Silver: I thought a lot about there's probably no better time in my life than after I graduated college because I had really no expenses at the time. um you know, no family you know family commitments or anything like that. And so it was a relatively low risk time actually to start. And I figured, look, if if it didn't work out, I could always go back to corporate America. But luckily, it worked out very well. And here I am almost 20 years later, still doing entrepreneurship.
Alejandro Cremades: And we'll talk about your latest baby too. Now for this one, for the first one, for PatientCo, how was that? How did you guys get the band together? You know, and how did you get going? I mean, tell us about the origins.
Joshua Silver: Yeah, so I partnered with another serial entrepreneur, actually. We really split the world almost in half. I took product and engineering and operations. He took the go to market and sales side of things.
Joshua Silver: And he had also gone to Georgia Tech, although a number of years before myself. So we had had known each other from the the Georgia Tech alumni network and
Joshua Silver: had been talking for years throughout my college experience about different ideas.
Joshua Silver: And it it kind of finally came time that I was graduating and said, all right, it's time to do this.
Joshua Silver: Let's go. and at that point, we got into you know deep idea search mode where we really spent a lot of time thinking about what would be a good idea.
Joshua Silver: And you know unlike a lot of other entrepreneurs that are really kind of mission driven or solving some personal problem, we took a much more engineering centric approach to it in terms of not the technology, but in finding the problem.
Joshua Silver: And we looked at what were the trends, what were actual problems, and most importantly, how can we make money for someone?
Joshua Silver: That's been a a recurring theme in my business career is always, how can we help a company make money?
Joshua Silver: It's not about time savings. It's not about efficiency. When you help a company make more money, I've found that it becomes a must have product.
Joshua Silver: And and all of my companies, all three of them now have have kind of shared that same theme.
Alejandro Cremades: So for example, with patient collect, what were the ingredients that made it the idea that you all ended up you know thinking like, hey this is worth pursuing?
Joshua Silver: Well, when we started, we actually thought we were going to go out and solve the problem of hospitals and doctor's offices at the time didn't have online bill pay. And this was in the mid 2000s.
Joshua Silver: But back then, almost every health care payment came through a check. And so the initial idea was, let's just electronify all these payments. As we got into it, we quickly realized that the electronification wasn't the core essence of the problem.
Joshua Silver: The core essence of the problem was that most hospitals are only collecting 50 cents on the dollar of every patient bill they send out.
Joshua Silver: So imagine a grocery store. This is the example I could give people. And in the checkout line, every other person just doesn't pay and they walk out with their groceries. What do you think would happen to the price of groceries?
Joshua Silver: Well, it would have to double because every other person wasn't paying. Well, guess what? That's exactly what happens in the healthcare realm. And so when we realized that 50% of patients weren't paying their bills,
Joshua Silver: and many of them had the financial capacity to do so, there were other reasons they weren't paying. That's when we pivoted and realized now we can go deep dive on the real problem, which is collectability in healthcare. care
Alejandro Cremades: Now, talk to us about the early days. What did they look like and how did you guys go about shaping up to the and MVP until you were like, I think i think that this is this is heading somewhere.
Joshua Silver: Yeah, you know, it's really tough because my original company, PatientCo, was at the intersection of two of the most regulated industries on the one hand.
financial services and on the other hand, healthcare IT. So you think about things like PCI and HIPAA and compliance. It's very, very challenging in both of these spaces to get something going from scratch because unlike, for example, vertical software where you can spin up an MVP and it maybe be sort of kind of works, there's really no room for error when you're moving people's money and dealing with healthcare data. And so it turns out that it's a relatively big build to even get your very first customer and then convincing a customer to be the very first one in these highly regulated industries was really, really challenging.
Joshua Silver: Luckily, we were able to kind of work our way into it by going to friends of friends of friends who owned small doctor's offices, and you know then you work your way up to rural hospitals that are more like clinics, and then you kind of work your way up to regional facilities.
Joshua Silver: And then you know by exit, we were working with some of the largest healthcare care organizations in the country, including BJC Healthcare out of St. Louis and Piedmont out of Atlanta, um you know facilities that had 25 and 30 major hospitals and and then thousands and thousands of doctors.
Joshua Silver: So it's really about just chiseling your way in, wedging your way into that very first one, and then working your way up to bigger and bigger clients until you you've kind of reached the the type of client you want to work with long term.
Joshua Silver: So we were aligning ourselves primarily with the collections. And so we took a piece of every transaction that that came through and we went and we told the hospitals, look, you're leaving 50 cents on the dollar today on the table.
Joshua Silver: And over the different time periods and different phases of growth, you have different needs. But really trying to distill down what does good look like in this role? Is this a zero-to-one role?
Joshua Silver: Is this a high-growth role? Is this someone who's coming to build out the team? Is this a role where you can take a flyer on someone who maybe hasn't done it before and hope they figure it out? Or is this a role in a time where you need someone who's done this 10 times and they're going to come in on day one and know what's going on?
Joshua Silver: And that’s probably the biggest mistake that I’ve made and the biggest mistake I see other founders make—is not getting the right people on the bus at the right time.
Joshua Silver: And it costs you not only a lot of money, but it costs you a lot of opportunity because you're forgoing that growth that you could have had.
Joshua Silver: And in most businesses like ours, it compounds over time. And so you miss a quarter or two—it’s not just that you missed a quarter or two, you missed the compounding effect of that quarter or two until you sell the company, which could be a decade later.
Joshua Silver: So it turns out it's not just one or two quarters of miss; it could be 40 quarters of miss.
Alejandro Cremades: Fully agree on that. So, Joshua, for the people that are listening, that would love to reach out and say hi, perhaps learn more about Rainforest, what is the best way for them to do so?
Joshua Silver: So you can learn about us on our website at rainforestpay.com. Also, I encourage everyone to look me up on LinkedIn. I'm a really avid writer. I put out content usually two or three times a week.
Joshua Silver: Some of it’s payment-specific, but also a lot of it’s just general advice on leadership and growing businesses. And I'm extremely transparent there. I share mistakes we made.
Joshua Silver: I share times that we've messed up. I also share things that are working. And so hit me up on LinkedIn.
Alejandro Cremades: Amazing. Well, Joshua, thank you so much for being on the DealMaker Show today. It has been an absolute honor to have you with us.
Joshua Silver: Thank you so much for having me. I really appreciate it.
