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The Trust Revolution: How SiteWire’s Bryan Kester Is Transforming Construction Finance Through Relationships

In an industry notorious for its resistance to technology, one founder is proving that relationships—not just innovation—hold the key to category creation.

In a recent episode of Category Visionaries, Bryan Kester, CEO of construction technology company SiteWire, revealed how his startup is tackling one of the most painful bottlenecks in residential construction: the glacial pace of construction loan disbursements. With $3.2 million in funding, SiteWire has developed a solution that turns a three-week wait for critical construction funds into a two-hour process—but their go-to-market journey offers even more valuable lessons for B2B founders.

The Construction Finance Bottleneck

The fundamental problem SiteWire addresses is deceptively simple yet profoundly impactful. As Bryan explains: “The way that construction loans work, whether you’re building a skyscraper or doing a fix and flip that you see on home and garden TV, is that you’ll get a construction loan… but the other part of the loan that is meant for the actual construction work, you don’t get that loan money until you’ve done the work or achieved certain milestones in the project.”

This creates a cash flow crisis that threatens project timelines across America. In traditional construction finance, receiving progress payments requires physical inspections followed by lengthy paperwork processes.

“What traditionally happened is the lender would send an inspector out to your job site, would take three to seven days, and you’d be waiting, you know, a week or two or three in some cases, for half a million dollars or $1 million to come your way after the work’s been proven, the reports have been filed, etc,” Bryan notes.

SiteWire’s innovation is replacing this physical inspection with a mobile app that allows builders to document work virtually, leading to near-immediate funding release. It’s a solution born from Bryan’s personal experience and family background in construction—precisely the kind of domain expertise that gave him insight into an invisible but critical pain point.

The Challenge: Disrupting Two Technology-Resistant Industries

What makes SiteWire’s GTM journey particularly instructive is the environment they’re operating in. As Bryan bluntly states: “The two least technology adopted industries in the planet, and this is behind even healthcare and sectors of defense that are antiquated, are real estate and construction. And our company basically has one leg in both.”

This resistance to technology adoption creates immediate GTM challenges that can’t be solved with conventional digital marketing approaches. The market wasn’t actively seeking a solution like SiteWire because the status quo, while painful, was simply accepted as “how things are done.”

Bryan explains: “This industry just does not really embrace disruption. Everything in real estate’s very transactional… Getting all those people to coalesce around a different way of doing things is an absolute nightmare.”

For B2B founders targeting traditional industries, this environment requires a radically different go-to-market approach—one built on relationships rather than conversion optimization.

Relationship-First GTM: Making Friends, Not Leads

In an era obsessed with digital marketing funnels and automated sales processes, SiteWire’s go-to-market strategy feels almost anachronistic—yet it’s precisely what their market requires.

“This whole industry is driven by relationships and trust,” Bryan explains. “What we’ve had to do is get on the ground, you know, boots on the ground, go to a lot of conferences, make friends. It’s literally about making friends and establishing a relationship that you’re not a shark, you’re not there to screw somebody over.”

This relationship-first approach stands in stark contrast to the traditional Silicon Valley playbook of product-led growth and digital customer acquisition. It’s a reminder that in some industries, real human relationships remain the most effective path to market adoption.

Bryan has built his go-to-market motion around this reality: “I have a couple people that are almost airborne all the time, just making friends at conferences and that’s our go-to market vector, just relationship building and trust building and then created word of mouth and network effects for us.”

The results speak for themselves. While SiteWire’s competitors have raised hundreds of millions in funding, Bryan’s scrappier, relationship-driven approach has established genuine product-market fit with significantly less capital.

The Consultative Differentiator

Beyond relationship-building, SiteWire’s GTM strategy includes a consultative approach that stands out in an industry dominated by transactional relationships. Bryan explains: “A lot of folks, particularly in our industry, have never had a salesperson come along and be consultative and really focused on problems versus trying to ram something down their throats.”

This problem-focused approach differentiates SiteWire in a market where most vendors are simply trying to close the next deal rather than solve fundamental industry challenges. It’s a lesson in how B2B founders can position themselves as trusted advisors rather than vendors, even in the most transactional industries.

Bootstrapping vs. Fundraising: A Contrarian Perspective

Bryan’s approach to fundraising reflects the same thoughtful, strategic mindset that characterizes his entire go-to-market strategy. Despite operating in Silicon Valley—where massive funding rounds are often celebrated as success metrics—Bryan has deliberately maintained a bootstrap mentality.

“Everyone calls it product market fit. Now what you’re really looking for is you’re trying not to dilute the company, dilute your future and raise too much capital until you’ve got a model, a business model in a situation where people are coming to you and asking you to do things or wanting to learn more,” he explains.

This patient, strategic approach to fundraising has allowed SiteWire to maintain optionality while competitors who raised too much, too soon have found themselves in precarious positions: “I have a couple competitors right now that have raised 270, 300 million, literally a hundred times what we’ve raised. And they’re in valuations right now where there’s no escape.”

It’s a powerful reminder that fundraising should be an enabling tool, not a goal in itself—a perspective that runs counter to much of Silicon Valley’s conventional wisdom.

Building Bridges Between Construction and Finance

At its core, SiteWire’s long-term vision isn’t just about technology—it’s about solving a fundamental trust gap between two disconnected worlds.

“Finance folks get into finance to be wealthy,” Bryan observes, “and construction people do get in to be wealthy, but they also get in to be wealthy by working outside with their hands and actually staying away from technology.”

By using technology to bring these disparate groups together, SiteWire aims to solve not just a business problem but a human one—building trust between industries that have traditionally struggled to understand and collaborate with each other.

The ultimate goal extends far beyond construction finance efficiency: “Our vision is to keep building something out that brings more trust into the industry between people who are building homes and the lenders,” with the mission of helping to address America’s ongoing housing shortage.

Lessons for B2B Founders

SiteWire’s go-to-market journey offers several valuable lessons for B2B founders, particularly those targeting traditional industries:

1. Domain expertise reveals hidden pain points: Bryan’s background in both construction and technology helped him identify a critical industry problem that wasn’t being addressed.
2. Relationship-building trumps digital marketing in traditional industries: In sectors where trust is paramount, face-to-face relationship-building may be the most effective GTM strategy.
3. Consultative selling can differentiate in transactional environments: Being problem-focused rather than product-focused can set you apart in industries accustomed to purely transactional relationships.
4. Strategic fundraising preserves optionality: Raising capital at the right time and at the right valuation keeps options open, while premature fundraising can create existential risks.
5. Look for opportunities to build bridges between disconnected stakeholders: Sometimes the greatest value creation comes from connecting groups that have struggled to collaborate effectively.

As more B2B founders look beyond purely digital markets to transform traditional industries, SiteWire’s relationship-driven approach offers a valuable blueprint for successful category creation—even in the most technology-resistant sectors.