Keeper Systems: Building AI infrastructure for social services at Elbow Grease

Keeper Systems is an AI infrastructure company for social services, founded by Blake Robertson and Andrew Tam. Blake started the company after a serious illness in college left him navigating a maze of government and social support systems on his own. He and Andrew, a longtime NYC-based startup CTO, bootstrapped the company for nearly two years before joining Elbow Grease, Gutter Capital's founder-led accelerator. During the 10-week program, they completed a full rebrand from Upkeep Care to Keeper Systems, rebuilt their core product, and moved into final contract negotiations with a major statewide social services referral network. We had an individual outside of Gutter conduct unbiased “graduation interviews” with each founder about their experience with the program, and this is what we learned from their answers.

Key facts

• Company: Keeper Systems, AI infrastructure for social services

• Founders: Blake Robertson (CEO), Andrew Tam (CTO)

• Background: Blake: Yale School of Public Health, driven by his own experience navigating social services after a serious illness. Andrew: former CTO at multiple venture-backed startups, based in New York City for more than a decade.

• Before Elbow Grease: Bootstrapped for close to two years; Blake split time between Yale, his hometown in Texas, and Andrew's couch in Brooklyn.

• Program: Elbow Grease accelerator: $300k investment, 10 weeks in NYC

• Mentor: JT White, Co-Founder and CEO of Forerunner

• Partner: Dan Teran, Co-founder and Managing Partner at Gutter Capital

• Key outcomes: Full rebrand from Upkeep Care to Keeper Systems, a rebuilt core product, and a contract in negotiation with a statewide social-services referral network

  
  

What Keeper Systems does

Keeper Systems builds AI infrastructure for social services. The company's public-facing AI is designed to strip away the most burdensome parts of finding and accessing government and community support, so people in crisis spend less time lost in administrative complexity and more time in real conversations with real people. Keeper isn't built to replace the human side of support. It's built to clear a path to it.

The origin story

Blake Robertson got sick in college. What followed was a diagnosis with a chronic condition that put him in a wheelchair and stripped away his independence overnight. The resources that could have helped him existed. Finding and using them didn't come easily. The systems were complex, slow, and hard to navigate, and Blake went without help he needed simply because the path to it was too burdensome while he was dealing with his illness.

After his recovery, Blake enrolled at Yale School of Public Health with a specific goal: put the best available technology into the hands of people navigating the same maze he had. He met Andrew Tam when they were guests at a wedding. Andrew, who had spent his career as CTO of multiple venture-backed startups, was between projects and looking to build something where success was measured in lives improved, not dollars raised. Blake was already building. Andrew jumped in to help, and Keeper Systems was born.

They bootstrapped for almost two years before Elbow Grease, working remotely for most of it. Andrew had been in New York for over a decade; Blake, based in Texas and finishing school in Connecticut, slept on Andrew's Brooklyn couch on and off while the two worked toward getting into the same room full-time.

Inside the program

A mentor who helped them put a dollar figure on their value

JT White, Co-Founder and CEO of Forerunner, was Keeper's mentor, and Blake and Andrew both point to him as one of the main reasons they joined the program in the first place. A single 30-minute call during the interview process before they started the program resulted in advice they could act on immediately, something neither founder had gotten from other accelerators they'd talked to. JT had years of experience working in the GovTech space and had learned how to work with the long sales cycles and complex purchasing process. Once the program start, JT met with them weekly, including when he was on part-time parental leave. One piece of guidance stood out: JT helped them calculate the actual dollar value Keeper's platform delivers to a customer, which gave them a real basis for pricing and enabled ROI conversations.

A partner who told them to slow down

As co-founder and Managing Partner at Gutter, I partnered directly with half of the Elbow Grease teams, including Andrew and Blake. Both founders told me my advice was counterintuitive to them at first. Instead of pushing them to chase revenue everywhere, which was their expectation of a venture investor, I told them to slow down and focus on going deep in one market before expanding. As part of our regular meetings, I worked with them to map out where the technology needed to go next and stayed aligned with them on milestones that reflected their business, not an arbitrary fundraising checklist.

Support across every function of the company

Elbow Grease gave Keeper Systems what Blake described as new team members without the new hires. Richard Hughes, Head of Talent, supported their recruiting process. Vince Li, Head of Design, led the company through its full rebrand, from Upkeep Care to Keeper Systems, including a redesign of the core product. Josh Lavine, a founder and executive coach, worked with the team on co-founder dynamics, helping them see that operational issues were often relationship issues underneath. Sarah Quirk, a startup marketer, helped refine their messaging for their new website. Blake credits this team with teaching him how to find his own voice describing the company.

A seat at the table on New York City policy

During the program, Gutter hosted a meeting that brought together New York City policy leaders and major tech companies to discuss how technology could serve the city's residents. We brought government officials directly into the room. For a company selling into the historically difficult-to-access world of government and nonprofit social services, those relationships opened doors that don't typically open through cold outreach.

A community built on support, not just a check

Blake and Andrew described Elbow Grease as a community from the moment they walked in, with founders trading knowledge in workshops and Slack channels. I told them early on about our approach to carry: a portion of the fund's returns is reserved for founders, aligning incentives so that founders helping each other pays off for everyone. Andrew called the structure forward-thinking.

Programming that made room for real work

Both founders point to the mix of fireside chats, lunches, and workshops as valuable without getting in the way of building. Highlights included a fireside chat with WeWork's co-founder and a lunch-and-learn where mentor JT White shared with the full cohort the same advice he'd been giving Keeper privately for months.

The results

• Completed a full rebrand, changing the company's name from Upkeep Care to Keeper Systems and rebuilding the website and core messaging with Gutter's marketing and design leads.

• Rebuilt the core product, shipping new features weekly alongside Gutter's head of design.

• Moved into final negotiations on a major new contract with a statewide social-services referral network.

• Established relationships with New York City government officials, positioning Keeper to eventually bring its technology into city services.

• Built pricing around measurable ROI, using a framework developed with mentor JT White to show customers the dollar value Keeper delivers.
  
  

Why they chose Elbow Grease

Blake and Andrew first heard about Elbow Grease at an AI demo event in Brooklyn, where Operating Partner Richard Hughes described a program built to invest in founders working on hard, meaningful problems. For two founders building in social services, that framing was the draw before they'd even applied.

But they said what sealed it was the interview itself. Instead of a 10-minute pitch built around hitting the right buzzwords, my co-founder James and I each spent an hour with them, asking about their backgrounds and why they were building what they were building. Andrew called it a different level of understanding than any other investor conversation he'd had. Blake put it simply: come in ready to work, and you get out exactly what you put in.

Frequently asked questions

What is Elbow Grease?

Elbow Grease is a small-batch, founder-led accelerator run by Gutter Capital in New York City. It takes 10 to 15 pre-seed software companies per cohort, invests $300k per company, and runs for 10 weeks at Gutter's headquarters on Canal Street in Chinatown.

What is Keeper Systems?

Keeper Systems is an AI infrastructure company for social services, founded by Blake Robertson and Andrew Tam. Its AI helps people in crisis navigate government and community support systems faster, so they spend less time on administrative complexity and more time getting real help from real people.

Who mentored Keeper Systems at Elbow Grease?

JT White, Co-Founder and CEO of Forerunner, mentored Keeper Systems. He met with the founders weekly throughout the program and helped them build an ROI-based pricing model for their product.

What results did Keeper Systems achieve during Elbow Grease

Keeper Systems completed a full rebrand from Upkeep Care to Keeper Systems, rebuilt its core product, and moved into final negotiations on a contract with a statewide social-services referral network.

How much does Elbow Grease invest in each company?

Elbow Grease invests $300k per company as a first check, with the potential for a follow-on pre-seed opportunity.

Apply to Elbow Grease

If you're doing your life's work and solving a big problem you understand, we want to know about it. Elbow Grease's second cohort is now accepting applications through July 31. Learn more at elbowgrease.cc and apply at https://forms.gutter.cc/eg0002-application