These Serial Entrepreneur Twins Raised $60 Million To Build The First Hybrid Workplace Experience Platform With AI Capabilities

Zach Dunn’s entrepreneurial story is unique and intertwined with his twin brother, Sam. This blog explores their journey from starting a blog, scaling an agency, pivoting to product development, raising millions, and thriving through a pandemic—all while doing it together as twins.

From their rural upbringing in Western Massachusetts to building a venture-backed product that revolutionized workplace scheduling, the Dunn brothers have navigated challenges, seized opportunities, and embraced the art of balancing vision and execution.

Listen to the full podcast episode and review the transcript here.

The Humble Beginnings

Zach and Sam Dunn were born in Connecticut but grew up in a small town in Western Massachusetts, a world away from the bustling innovation hubs of Boston. Their hometown had the occasional alpaca farm dotted the landscape, starkly contrasting the tech scene they later entered.

The brothers’ journey began when they both attended the University of Hartford, where Zach studied web design and Sam majored in marketing. This complementary skill set laid the foundation for their first venture.

From Blogging to Business

While still in university, the brothers started a blog called Built Internet, which quickly gained traction and became one of the top 10 blogs in the web design and development community. Their tutorials and insights attracted attention, and soon, they found themselves fielding client requests.

As a result, the duo started to think about monetizing it via a service-based approach. Zach explains that their timing was perfect since they started the blog right around the time social media exploded on the internet. Twitter and Facebook had begun dominating the scene.

What began as small $1,500 projects evolved into significant $30,000-$50,000 contracts. By their senior year, the brothers realized they could sustain themselves through their agency work, and thus, One Mighty Roar, their digital agency, was born.

Talking about how their skills complemented each other, Zach says he is more focused on the execution side of operations, while Sam is the big-picture guy. Although some of their endeavors have also been learning experiences, they have balanced each other perfectly.

Finding Their Niche in Digital Experiences

One Mighty Roar stood out by creating innovative digital experiences for consumer brands. Using a Twitter account for business was an alien concept at the time. The duo created a notable niche that involved designing in-person digital interactions, such as RFID wristband integrations at music festivals.

These projects allowed attendees to interact with kiosks and screens, creating personalized, memorable experiences. This ingenuity garnered interest and visibility, establishing the agency as a leader in blending technology with real-world events.

Despite their success, the brothers recognized the limitations of a service-based model. “The dream is to make money while you sleep,” Zach quipped. They began productizing their work and creating reusable tools for clients.

One such innovation—a motion-sensor-enabled conference room booking system—went viral. Presented at a major design conference, this concept became the genesis of their first venture-backed product: Robin.

Robin: Scaling Workplace Scheduling

Robin began in 2014 as a conference room scheduling tool, later expanding into a full-fledged workplace management system. Known for its iconic iPad interfaces outside meeting rooms, Robin now helps businesses optimize office space, transitioning into hot-desking and activity-based work solutions.

Zach recalls how they were invited to present at Neocon, a furniture, architecture, and design conference in Chicago. Over a decade, Robin raised $60M across four funding rounds, scaling to meet evolving workplace needs.

Zach reveals how people would approach them with the problem of organizing hundreds of conference rooms. They wanted solutions to enable them to book appropriate rooms and ensure attendees could find the right meeting venues.

Robin eventually evolved to supporting activity-based work, which optimizes and designs the workplace to support the type of work being done instead of according to the number of workers.

For instance, having a designated area for brainstorming profoundly impacts scheduling meetings and coordinating attendees.

Navigating Fundraising Challenges

Transitioning from a service business to a product company wasn’t without hurdles. Zach recalls early skepticism from VCs about their background, as many believed entrepreneurs from an agency couldn’t successfully build products.

Proving their capability required relentless effort and a clear vision. “You’re competing not just with similar products but against every other pitch for limited VC slots,” Zach noted.

Zach looks back at their initial seed funding round in which they raised $3M to supplement their savings from One Mighty Roar. Having pulled $1M from their first company, Zach and Sam realized they would need much more money to build the product.

Identifying opportunities is easy, but seizing and acting on them can be challenging because of financial constraints. Bootstrapping can take the concept only so far. That’s when the duo decided to approach investors for funding, raising $60M across four rounds.

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Looking back at the lessons they learned, Zach talks about balancing aspirations for the company’s short-term goals. From an outsider’s perspective, getting funding for a tech startup is easy, and founders only need to demonstrate the opportunity.

However, conservatively speaking, tech VCs fund just three to four companies yearly, sometimes a few early-stage startups. Entrepreneurs must meet their criteria as viable candidates within that particular year.

Scaling and Pivoting Through the Pandemic

The pandemic posed an existential challenge for Robin, a company deeply tied to office spaces. By then, Robin had already raised $30M and was poised to start ramping up and developing its second product line, the first being conference rooms.

With offices shuttered, the team pivoted to focus on hot desking solutions, which became essential for companies transitioning to hybrid work models. Hot desking or hoteling allowed users to book desks instead of just rooms, so they don’t need assigned seats in an office.

What seemed like a disaster turned into an opportunity, as demand for Robin’s products surged, leading to threefold growth in a year. Initially, Zach and Sam had estimated growth to take multiple years, which instead happened within months.

A New Chapter with Rally

After a decade with Robin, the brothers are now building Rally, https://rally.space/ a video storytelling tool for recording product presentations – demos, updates, and launches. Born from pain points experienced at Robin, Rally aims to simplify how teams present products.

Zach’s journey underscores the importance of leveraging past experiences to build solutions for the future. The Rally business model is per seat with a secondary business model of AI credits. Rally sells to front-line workers who are interacting with customers and prospects.

Essentially, Rally targets go-to-market teams and people supporting customers with product marketing and sales enablement. The model is distinct from selling workplace scheduling software, where interactions are with facilities and IT teams.

Rally aims to close the gap that companies face between building the product and communicating those changes to teammates and customers.

Zach points out that how most companies present their products to customers can be disjointed. When a product constantly changes, perception gets out of sync with reality for customers and internal teams, such as sales or customer success. The product you actually have is different from the one you end up selling.

Rally helps B2B companies easily present their latest product updates and get feedback loops quickly, enabling them to enhance their products.

Raising Funding for Rally

Talking about their fundraising journey, Zach explains that they leveraged their previous investors from Robin. They also had angel investors who supported their acumen and vision.

Looking back at their entrepreneurial journey, Zach advises aspiring founders to not only hire skills and talent that they lack. But also think about how they can scale with the company.

Another lesson Zach learned from their blogging days is that founders should explore multiple opportunities to monetize their ideas.

Conclusion

Zach Dunn’s story is a testament to the power of resilience, adaptability, and collaboration. From a rural upbringing to creating transformative workplace technologies, Zach and Sam have shown that entrepreneurial success is all about navigating challenges and seizing opportunities.

Their journey serves as an inspiration for anyone looking to turn ideas into impactful ventures.

Listen to the full podcast episode to know more, including:

• Building a company with a sibling can be challenging yet rewarding, leveraging complementary strengths like vision and execution.
• Transitioning from a service-based agency to a scalable product business requires identifying reusable solutions and pivoting strategically.
• Success often hinges on timing, as Zach and his brother capitalized on the early days of social media and tech innovations.
• Overcoming biases against service-to-product founders, they raised $60M across four funding rounds by demonstrating adaptability and vision.
• Pivoting their office software business during COVID-19 turned a crisis into an opportunity, leading to rapid growth in desk-booking solutions.
• Each venture, including their latest company, Rally, builds on lessons learned from solving pain points in previous businesses.
• Balancing short-term execution with long-term vision is crucial for convincing investors and achieving sustainable growth.

 

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