An Interview With Matt Schwartz, CEO of Inspry
We caught up with Matt at PressConf 2026, where conversations around hosting, agency growth, and the future of AI were front and center. It was the perfect setting to hear directly from someone living these challenges every day.
Web hosts should listen directly to the people managing client sites every day to truly understand agency expectations.
Matt Schwartz, CEO of Inspry, brings years of experience building websites, managing client infrastructure, navigating hosting platforms, and solving the kinds of problems that only show up when websites are tied directly to revenue, support, and reputation. He does not speak from theory but from daily practice.
His story reflects how many agencies have evolved over the last decade. Starting as freelance work, agencies often mature into operations with documented processes, specialized tools, and higher expectations from hosting partners. Criteria for choosing a host shift: price matters less, trust, fast support, reliable backups, and flexibility matter more. Increasingly, AI is changing agency operations as well.
As agencies evolve, hosting businesses at every level, from product owners to CEOs, can learn from these changing priorities.
How Matt Schwartz Built Inspry Into an Established Agency
Like many agency founders, Matt did not begin with a fully formed company. He built websites while in college and gradually turned that experience into something larger.
“I was building websites in college on the side,” he said. “2011 was when I officially established it.”
Matt experimented in the early years. He worked with Drupal at the University of Georgia, managed Joomla websites, and moved deeper into WordPress as the platform matured into a stronger CMS. Like many founders, he balanced side work, teaching, and contract projects before he committed fully to agency ownership.
The business changed when Matt transformed it from a source of income into a true operation.
“In 2015, I made a real decision to formalize it, hire employees, and build actual processes,” he said. “That is when it became a serious business.”
That distinction matters. Once an agency reaches that stage, hosting becomes a key partnership that shapes both agency operations and outcomes. Agencies benefit from reliable, strategic host relationships that safeguard client trust and enable efficient problem-solving. Hosts, in return, gain loyal, growing agency clients who value expertise and fast, context-aware support.
Why Agency Hosting Expectations Change Over Time
Matt’s experience highlights how agency expectations evolve as a business matures, focusing priorities and sharpening needs.
Early on, agencies often overbuy, overbuild, or choose infrastructure that feels impressive. Matt remembers that phase clearly.
“I remember having these elaborate setups with load balancers and all kinds of infrastructure that, in hindsight, we probably did not need,” he said. “At one point, I realized I was paying something like $700 a month for a setup that made me feel important, but a much simpler plan would have done the job just fine.”
That is an important insight for hosts. Agencies want confidence in their hosting partners, focusing on collaboration that strengthens business outcomes. While customers benefit from simplified solutions that fit real needs, hosts benefit from building trust and understanding the daily challenges their agency clients face.
Over the years, Matt’s agency worked with a number of hosting companies, including WiredTree, Rackspace, SiteGround, Cloudways, Pressable, BigScoots, Nexcess, and Rocket.net. That kind of experience gives an agency a strong sense of what actually matters once real client work is involved.
Do Agencies Use One Web Host or Multiple?
One of the most useful takeaways from this interview is that mature agencies often do not settle on one host for everything.
“We use multiple hosting companies now, depending on the scenario,” Matt said.
This multi-host approach is a practical decision. Since different websites require different hosting, agencies recognize that forcing every client into the same environment can lead to later issues.
For simpler brochure-style websites, Matt said Pressable has been a strong fit because of its stability and reliability. “We have never had an outage there,” he said. He also pointed to hourly backups as a major advantage, especially since that level of frequency is still uncommon across all hosts.
For more demanding WooCommerce projects, the agency prefers Rocket or BigScoots. That choice comes down to performance, tunability, and support. Matt explained that while some managed environments are excellent for standard sites, more complex e-commerce builds often need a setup that can be adjusted more precisely.
That is a lesson many hosting companies should heed. Agencies benefit from hosting partners who specialize in different workloads, providing tailored solutions and building long-term trust. Hosts who deliver exceptional results for particular use cases benefit from dedicated agency partnerships and referrals in those segments.
What Matters Most in Hosting for Agencies
When asked what matters most in hosting, Matt’s answer was direct and immediate.
“One hundred percent. Support and trust.”
That answer should stand out to anyone building a hosting company. Agencies care about uptime, performance, and infrastructure from a host, they rely on these for client satisfaction. However, these have become baseline expectations. What truly benefits agencies, and differentiates providers, is the support they receive when something breaks or when a team needs real help fast.
Matt explained that by the time his agency reaches out to hosting support, they have usually already done the first round of troubleshooting. They are not opening tickets because they have forgotten how to clear the cache or restart a plugin. They are reaching out because they need a real partner on the other side.
“So by the time we are talking to support, we have usually already done the initial work,” he said. “We need to be able to get past tier one quickly.”
He was especially blunt about what frustrates experienced agencies: support teams ignore the full ticket and repeat steps the customer already documented.
“If we say we already checked five things and they just repeat those same five things back to us, then they did not read the ticket,” he said.
That is a clear signal for hosting leaders. Agencies want support that understands context, not just access to support.
Why Backups Are Still a Major Differentiator in Hosting
A strong backup strategy goes beyond technical details for agencies; it acts as essential business protection.
Matt described a past experience in which a host’s backup system failed, permanently changing how his team thinks about redundancy.
Matt shared a difficult experience when a host’s backup system failed catastrophically. As he explained, “They basically told us the nearest usable backup was around 45 days old, and it was an e-commerce site.”
That kind of failure teaches a hard lesson very quickly.
“That was the moment I realized you cannot trust a single backup source, no matter who the provider is.”
As a result, his agency now employs a dual-backup strategy: relying on host-level backups but always maintaining a second, independent backup system.
How Agencies View AI in Hosting Support
When considering AI in hosting, Matt’s view was nuanced and practical, weighing both the advantages and limitations.
“It depends,” he said.
He values AI when it acts like strong, interactive documentation, especially for tools or systems used infrequently. He made it clear that AI support quickly becomes frustrating when it just rephrases public documentation without understanding the actual issue.
“If it is a plugin or a tool I do not use every day, AI can be useful,” he said. “But when it comes to hosting, especially if I know the platform well, AI support is often less useful because I have probably already tried what it is going to suggest.”
That is a critical distinction. Agencies are not against AI. In fact, many are using it aggressively inside their own businesses. What they are against is low-context AI that slows down escalation and impedes expert help.
For hosting companies, that means AI should enhance the experience and complement human interaction. Agencies benefit from time saved and context-relevant answers, while hosts benefit from higher satisfaction and operational efficiency, especially with expert human escalation.
How Agencies Are Using AI Right Now
A standout section of Matt’s interview was his clear articulation of AI’s operational role in modern agencies. AI is now integral to operations, project management, development, and internal systems, not just experimentation.
On the operations side, his team uses AI to improve estimates, scopes of work, and client communication. He described a workflow in which team members complete an estimate form, and AI reviews it for missing assumptions, exclusions, or gaps before it goes out. That helps the agency move faster while still protecting quality.
On the communication side, AI helps structure information more clearly for clients, making the human voice easier to scale.
On the development side, AI is helping with code audits, inherited site reviews, and smaller custom functionality. Matt explained that in the past, an inherited website often required paid discovery just to understand how messy it really was. Now AI can help accelerate the review process and give the agency a faster read on whether a project is stable, risky, or in need of deeper investigation.
That kind of use case matters because it benefits agencies through increased speed and productivity, and hosts by supporting more effective client service and streamlined operations built on AI-powered tools.
Why AI Workflows Are Reshaping Agency Operations
Matt also described something even more forward-looking: Inspry built an internal MCP server that connects tools such as hosting APIs, WordPress APIs, Freshdesk, and ClickUp, so team members can work across systems from within an AI environment.
That means someone can review a client issue, reference the website, make a small fix, and update internal and external systems without constantly switching between apps.
“Something that might have taken 45 minutes or an hour can now take a few minutes,” he said.
That statement points to a bigger change. Agencies are beginning to treat software interfaces differently. The interface is becoming less important than the infrastructure underneath it. AI becomes the access layer, while the real systems still do the work in the background.
Hosting companies should pay attention to this because it may change what customers want from their platforms in the near future. Strong APIs, improved system interoperability, and richer operational integrations may matter even more as agencies continue to build AI-assisted workflows.
What Web Hosts Can Learn From Agency Expectations
Taken together, Matt’s comments reveal a simple but powerful reality. Established agencies do not judge hosts the way entry-level customers do.
They care less about flashy offers and more about whether the host performs under pressure. They want support that reads the ticket. They want infrastructure that fits the workload. They want backup systems they can trust. They want flexibility without unnecessary complexity. And they increasingly want platforms that can fit into a broader, AI-assisted workflow.
There is also a strategic lesson here. Hosting companies often market reliability solely in terms of uptime, but agencies think more broadly. A site can be technically online and still be failing in ways that matter more to the client. A broken form, a damaged checkout flow, or a failed user journey can be just as serious as downtime. From the agency perspective, hosting is not only about whether the server is up. It is about whether the business is functioning.
That is why Matt’s perspective is so valuable. He is describing the lived expectations of an agency that has matured, specialized, and adapted with the market. Those expectations are only going to rise.
Jason Nickerson
With over 20 years of experience building and shaping the web, Jason Nickerson has worked across just about every corner of the industry. Jason’s career has mirrored the internet’s evolution — from the recovery after the .com crash to the open-source movement and the rise of cloud services that power the web today.