BUILDERS How Rainforest justifies the ROI of hosting a podcast and conference | Joshua Silver
Rainforest enables vertical software companies to embed payment processing directly into their platforms - solving the complexity that previously forced software companies to direct customers to separate banks or resellers for payment processing. Founded by Joshua Silver, who spent nearly 20 years in payments starting with PatientCo (a healthcare billing company that scaled to process billions for major healthcare organizations), Rainforest now serves as the enabling layer for thousands of vertical software companies. In this episode of BUILDERS, Joshua shares the unconventional GTM decisions that shaped Rainforest's trajectory: from making contracts a product feature to implementing a zero bugs policy, and why he measures podcast success by qualified lead conversion rather than download counts.
Topics Discussed:- The embedded payments opportunity: why software companies stopped directing customers to banks
- Building in highly regulated environments where traditional MVP approaches fail
- The extended foundation-building phase required before processing the first payment
- Transitioning from 2.5-3 years of founder-led sales to a scalable GTM motion
- Using contract terms as competitive differentiation rather than negotiation leverage
- Implementing a zero bugs policy and its impact on service costs and retention
- Building thought leadership through the Payment Strategy Show and Vertex conference
- Lead quality metrics over vanity metrics for content investments
Hire from the industry and invest disproportionately in technical onboarding: Rainforest maintains one of the highest concentrations of payments talent on a percentage basis—nearly everyone has worked in payments or payments-adjacent roles. But hiring isn't enough. Joshua obsesses over training because in complex sales, prospects ask detailed technical questions and "the moment that you give bad answers or don't know your stuff, they're going to detect that and that's going to detract a lot from the trust." When selling technical infrastructure, surface-level product knowledge kills deals. Every touchpoint—engineers, support, account execs—must understand not just how the product works, but why it works that way.
Engineer your standard contract to eliminate negotiation cycles: Joshua inverted conventional wisdom by making Rainforest's standard contract "overly favorable to the client"—no hidden terms, no punitive clauses, no exclusivity provisions. The result: "We don't have to spend a lot of legal time going back and forth. We don't have to invest a lot of time and by the way, burning a lot of goodwill too in contract negotiations." Prospects consistently report the legal process was shockingly easy compared to competitors. This isn't about being naive—it's strategic capital allocation. Joshua's philosophy: "Pick the fights that really matter and everything else is just rounding." Time spent in legal negotiations is wasted time that could be spent onboarding customers.
Embed sales capabilities into your customer success function: Rainforest trains their CS team on negotiation tactics, value selling, and objection handling—competencies rarely developed in post-sale teams. Joshua noted the primary goal is customer assistance, but growth is an underlying objective. This isn't about making CS "do sales"—it's about equipping them to have commercial conversations when customers naturally express expansion interest. The key enabler: strong product-market fit means "we don't have to sell it that much. It's really a conversation about solutioning."
Enforce a zero bugs backlog in high-stakes environments: Joshua's unofficial core value—"don't f with the money"—manifests in their zero bugs policy. It's not that they never create bugs; it's that "we don't tolerate living with them. We don't have a backlog of bugs to fix." When a bug is validated, they fix it immediately. His head of engineering recently discussed this on a podcast because people find it radical. The payoff: "When you have a higher quality product, you don't have to invest as much in service because the product just works and you have naturally happy customers." For infrastructure products where errors cascade into customer incidents, the accumulated cost of technical debt vastly exceeds the upfront investment in quality.
Qualify content success by whether it's converting your ICP: Joshua rejects vanity metrics entirely. When asked about podcast ROI, he said: "I'd rather have 100 highly qualified listeners that are great targets for us than have 100,000 listeners and not have 100 qualified ones." They track this rigorously—every inbound lead is asked how they discovered Rainforest, and an increasing percentage cite the podcast. Prospects explicitly say "we heard the podcast and nobody else is putting this content out there." The metric isn't downloads; it's whether qualified buyers are self-identifying through your content and entering sales conversations pre-educated and pre-sold.
Build ecosystem assets without demanding immediate attribution: Rainforest launched Vertex—a curated conference for vertical software founders and operators—that explicitly isn't a Rainforest sales event or user conference. Joshua doesn't track lead conversion from the conference: "That's not one of the key metrics. We actually look at NPS score as one of the key metrics. Did people find value in the conference?" They're running it twice this year because attendees report it's the highest-quality conference they attend annually. His philosophy: "Go create value, legitimate, genuine value for the ecosystem and they will come to us." They deliberately limit attendance to several hundred and choose venues that physically can't accommodate massive scale—maintaining intimacy as a forcing function against growth-for-growth's-sake.
Plan for extended pre-market build phases in regulated industries: Joshua's advice for payments founders: "Make sure you know what you're getting into. It's a big build and there's very low tolerance for misses." Before processing their first payment, Rainforest had to achieve PCI compliance, SOC2 compliance, and implement comprehensive security infrastructure. Only then could they begin customer development with close network contacts. He contrasts this with his standard founder advice: build an MVP, sell quickly, get feedback, iterate. In payments, that playbook doesn't work—"you actually have to build so much of the foundation first just to process your very first payment." Founders in regulated spaces need patient capital and realistic timelines that acknowledge compliance infrastructure isn't optional.
Institutionalize "ruthlessly simplify" as an operating principle: One of Rainforest's core values is ruthless simplification, which Joshua applies to "the legal contract, the engineering documentation, anything." He asks his team repeatedly when reviewing anything: "Can we simplify it? Can we simplify it? Can we simplify it?" The output quality dramatically improves. He references the Tim Ferriss framing: "What would this look like if it were simple?" When applied consistently, it cuts approximately 50% from plans, strategies, and deliverables—even when the creator thought they were already building simply.
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