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Document Crunch: How a Construction Attorney Transformed Contract Risk Management with AI

In a recent episode of Centaur Builders, Josh Levy, CEO and Co-Founder of Document Crunch, shared his journey of raising $38 million to revolutionize risk management in the construction industry. What makes Document Crunch’s story particularly compelling is their unwavering focus on a critical industry problem: the massive financial risk stemming from misunderstood contracts.

The $43 Million Problem in Construction

The construction industry faces a crisis hiding in plain sight. With a global value of $14 trillion, the industry operates on razor-thin margins while simultaneously carrying enormous risks tied to complex legal agreements.

“Fifty percent of construction projects are finishing overtime or over budget,” Josh explains. “Which means that 50% of the time one of those stakeholders who thought they were going to make a dollar is going to end up having to give something more than what they thought they were going to make.”

This risk translates directly into litigation. The average construction lawsuit costs $43 million and cascades through multiple stakeholders – contractors, subcontractors, architects, engineers, and owners. According to Josh, the number one cause of these lawsuits is “failure to understand and administer the contract terms by the project teams.”

From Legal Eagle to Tech Founder

Josh’s path to founding Document Crunch wasn’t part of some master plan. After completing a degree in construction management, he took a detour through sales roles before eventually attending law school. His sister questioned this decision, noting his personality didn’t seem suited for legal work.

“I said to her, I said, Jamie, I remember this conversation,” Josh recalls. “I think you may be right. But I do think that if one day I want to be in business, I can learn business. But they say that going to law school teaches you a different way to think.”

This decision proved pivotal. Josh spent over a decade as a construction attorney, eventually moving in-house with a large contractor. There, he witnessed firsthand the daily challenges project teams faced with contract administration.

“I would have a line of people outside my office every day,” Josh shares. “Hard hat in one hand, piece of paper on the other hand. ‘Hey, Josh, something happened on the job site. What do we do?'”

This experience revealed a critical insight: even sophisticated contractors with in-house counsel struggled with contract compliance at the field level. The gap between legal expertise in the back office and operational decisions in the field was costing companies millions.

Zero Pivots: Building with Industry Clarity

Unlike many startups that zigzag their way to product-market fit, Document Crunch has maintained its original vision throughout its six-year journey.

“Zero freaking pivots, man. Zero,” Josh says emphatically. “I always knew that we had a problem not just in the back office, but in the field.”

This clarity came from Josh’s deep industry knowledge. While he couldn’t design interfaces or write code, he understood exactly what problems needed solving. This expertise became Document Crunch’s competitive advantage.

“When we talk about the product roadmap, do you know what I do, man? I close my eyes and I think about interactions that I’ve had with the stakeholders that now are a user base in my former life,” Josh explains. “Like that’s what guides my telling people what we need to build now.”

Marketing Evolution: From Features to Problems

Document Crunch’s go-to-market strategy has evolved significantly over time. Initially, as a first-time founder, Josh was excited to promote the AI technology behind their solution. This approach quickly changed after receiving valuable advice.

“Pretty early on I met a marketing consultant who spent some time with me and he was like, ‘You need to be speaking to the problem more and to the features less,'” Josh recalls.

This shift aligned perfectly with Josh’s perspective as a non-technologist. “I don’t really care about technology in my personal life,” he admits. “I tell the Document Crunch, we call them the crunchers. I tell our team all the time we’re not like an AI company. We’re solving complex risks for our industry company.”

This problem-focused approach resonated deeply with their target market. By emphasizing their authentic understanding of construction challenges rather than technical capabilities, Document Crunch built significant industry credibility.

“In a vertical space like ours, brand reputation matters so much,” Josh notes. “And I think that’s not something you can fake your way to. That’s earned on the conference floor. That’s earned in the relationships.”

The AI Full Circle Moment

Interestingly, Document Crunch’s marketing has recently experienced what Josh calls a “full circle moment.” After years of downplaying their AI capabilities to focus on industry problems, the mainstream adoption of AI has created new market dynamics.

“We’re kind of the OGs for the construction AI space, though for three years weren’t talking about AI at all,” Josh explains. “But now that this mass adoption is taking place, what I’ve learned is that there’s a true market desire for trusted AI partners.”

This shift has allowed Document Crunch to leverage their early expertise in construction AI while maintaining their problem-focused approach. They’re now positioned as a trusted AI platform specifically built for construction risk management.

Building for Vertical SaaS Success

For founders looking to enter construction technology or other vertical markets, Josh emphasizes the importance of authentic industry knowledge.

“I believe that my founder market fit was a huge unlock at the onset of this venture,” he states. “My advice would be you better be like the most empathetic, open-minded person in the world because this is a unique industry and you also better go find a co-founder or someone close that has a deep, deep understanding of our industry.”

This perspective challenges the notion that outsiders can easily disrupt established industries without deep domain expertise. As Josh puts it, “You can’t go to market in our industry based on some thesis that was ginned up in B school on an industry that needs to be digitized. That’s not how this works.”

Beyond Software: Transforming an Industry

Document Crunch’s vision extends beyond software adoption to transforming the economics of the construction industry itself.

“I am 100% convinced that every single project on planet earth now needs document,” Josh shares confidently. But his ambition goes further: “In two years from today, can we start showing measurable results for a more profitable industry by virtue of what we’re doing? And I think that’s my personal holy grail, because it’s like my mission, man. I want this industry to better and I want to make it better.”

This goal of improving industry profitability represents a higher calling than mere technology adoption. As Josh concludes, “In two years from today, you’ll start to see Document Crunch be synonymous with better results and better outcomes.”

Document Crunch’s journey offers valuable lessons for B2B founders targeting vertical markets: deep industry knowledge creates unfair advantages, authentic problem-solving builds brand credibility, and meaningful transformation requires moving beyond features to focus on industry-wide outcomes. By staying true to these principles, Josh Levy has built a company poised to reshape a trillion-dollar industry from the ground up.