He Raised Over $51 Million To Build A Digital Banking and Money Management Platform That Brings Cash Flow Clarity to SMBs

Every founder’s journey is a unique blend of ambition, resilience, and lessons learned the hard way. Yoseph West embodies this entrepreneurial spirit, having navigated the complexities of building, scaling, financing, and successfully exiting multiple startups.

From his early days growing up in a small town in Canada to leading startups through acquisitions, Yoseph’s story is one of perseverance, strategic thinking, and continuous reinvention. In this riveting discussion, he talks about raising a phenomenal series A funding round in just 10 days.

Yoseph also talks about raising a series B round and taking his previous companies through their entire lifecycles before moving on to his current venture: Relay.

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

Early Life and the Seeds of Entrepreneurship

Born in London, UK, but raised in a small town outside of Toronto, Yoseph grew up in an immigrant household with English and Persian parents. His upbringing in a fast-evolving environment and a melting pot of cultures instilled in him a questioning nature—a great foundation for the business world.

“I was definitely the kid in school who would correct the teacher, and I just didn’t care,” Yoseph recalls. His drive to challenge norms and think independently was evident from a young age.

Yoseph was always inclined to question the status quo and direct his energies to building unique things simply by diving into immense possibilities and unlocking ideas. Childhood education, however, did not fully engage or challenge him.

Like many children of immigrants, he was pushed toward a career in medicine, law, or engineering. Yoseph sped through high school in just three years and pursued a law degree in the UK by age 20. While he found law school intellectually stimulating, the thought of practicing law felt constraining.

What law school did teach Yoseph, however, was invaluable—how to analyze information, build compelling arguments, and develop perspectives and conviction—skills that would later prove crucial in entrepreneurship. Law gave him the foundation for tackling the business side of things.

Yoseph learned that building something from scratch involves a lot of uncertainty and ambiguity. Entrepreneurship is about putting the pieces together so they are compelling and convincing not only to the market, but also to the team and investors.

First Foray into Startups and a Quick Acquisition

Rather than joining a law firm and stepping into a legal career, Yoseph gravitated toward business. He and a group of friends experimented with various startup ideas before landing on Vuru, a stock research platform—an ad-supported business model.

In hindsight, Yoseph concedes that it wasn’t the most sustainable. Despite this, he and his co-founders hustled, raised CAD 25K ($17K), and built something that attracted attention. Their work eventually caught the eye of Wave, a Toronto-based financial services app for micro SMBs.

Yoseph was impressed by the company and its operations, which had raised much more funding than Vuru. He was excited about learning from them. Although Vuru was poised for a pre-seed round, Yoseph and his co-founders weren’t convinced about the potential partners at the table.

Their solution was to approach Wave again. Through relationship-building and strategic positioning, they navigated an acquisition, essentially, an acqui-hire. This was an experience that shaped Yoseph’s understanding of startup cycles and the nuances of M&A.

Yoseph recalls the aggressive Q&A sessions they went through with Wave. The company wanted to affirm their caliber and team-building skills before moving ahead with the purchase.

“We managed to get ourselves to a place where I was just 24 when it closed. You get a little bit of cash, but more importantly, you gain experience,” he reflects.

Yoseph also got first-hand visibility into the complete cycle of a startup, going from a two-person to a 100-person company. He also learned how critical back office technology is to small business owners. Eventually, they moved Vuru clients to a new multi-product platform.

Yoseph recalls navigating the culture shock, figuring out how to deliver value, and feeling the same energy and ownership of the company where he was now an employee. He spent around a year at Wave, achieving certain equity milestones and getting valuable exposure to a small startup.

Lessons in Scaling: Hubdoc and the Realities of Growth

Post-acquisition, Yoseph joined Hubdoc, a company transitioning from B2C to B2B, offering digital file storage systems and document management solutions–valuable resources for small businesses.

Early on, Yoseph and his team faced significant hurdles: “In the first nine months, we were growing 20% month-over-month—but that was like $200. You go home and cry into your pillow,” he jokes. However, they persisted, focusing on product-market fit and customer feedback.

One of the key strategic decisions was targeting accountants and bookkeepers as a distribution channel to reach small business owners. While it seemed logical, adoption was slow since many professionals still used desktop-based accounting software.

Yoseph and the team had to get creative, faking integrations and features not yet live to test and understand market needs. They used these learnings to refine their approach.

Over time, consistency in growth compounded, and the company gained traction, though it took nine months to earn some amount of revenue. The patience and strategic positioning paid off when Hubdoc was acquired by Xero, marking another successful exit in Yoseph’s journey.

Looking back, he explains that, at the time, Xero was aggressively pushing cloud accounting in the North American market. At Hubdoc, they noted the market shift.

Thanks to word-of-mouth advertising, the business started to gain immense traction, scaling from zero to 25,000 paying small companies—a market-led motion. By the time the acquisition happened, they had 50,000 customers.

Building Relay–The Next Venture

After exiting Hubdoc, Yoseph spent some time as a consultant but was soon ready to dive into entrepreneurship again. In 2018, with his co-founder, Paul Klicnik, he started to toss around ideas. The duo realized they had spent the last 10 years unbundling their bank account.

Yoseph identified a problem small business owners faced: they were managing the finances of their modern businesses using traditional bank accounts. Bank balances were ineffective at delivering real-time, detailed, and helpful information about their true financial health.

Yoseph and Paul thought about creating a smart bank account, deeply interconnected with the small business accounting back office.

The tool could increase financial visibility, help small business owners make better decisions, and ultimately build more profitable businesses. They envisioned a banking solution that could deliver cash flow clarity.

Yoseph explains that Relay’s business model is a combination of traditional financial services. They make money off float revenue, i.e. interest income, and debit and credit interchange. Relay also has some transaction fees and a paid subscription.

Yoseph reveals they have raised approximately $52M for the company.

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The Art of Fundraising: Raising a Series A in 10 Days

Fundraising is often a grueling, time-consuming process, but Yoseph has always had incredibly supportive investors from their earliest days. The inflection point in their fundraising journey was when the company raised its seed round after raising a pre-seed mainly from local investors.

Yoseph explains how San Francisco-based Better Tomorrow Ventures led their seed round. He gives a shout-out to Jake Gibson, one of the co-founders of NerdWallet. Later, Bain Capital Ventures also led their seed and series A and B rounds.

Yoseph has an interesting story to tell about landing their series A funding round. He reveals how they had a long-term relationship with Keri Gohman, who previously ran Capital One Small Business Bank. She had also sponsored the Hubdoc acquisition by Xero.

Keri had previous experience with SMB neobank deals and was enthusiastic about Relay. She saw it as an SMB Neobank designed for small businesses with employees in the heart of America. Yoseph and his team invited Keri to their board meetings.

When Relay was ready for its series A round, Yoseph and his team were approached by another investor. They also brought in Bain Capital and Keri Gohman and pitched a compelling partnership. That’s how they managed to close a Series A round in just 10 days—an almost unheard-of feat.

As Yoseph explains, each funding round comes with its own set of challenges. Investors need to believe in two things–the vision of the world and what the future will look like. Secondly, they should be able to connect with the founder on a personal level. That’s the recipe for success.

Yoseph believes in bringing in investors who match the company culturally from the values perspective. He does not shy away from projecting his idiosyncrasies and quirks when connecting with investors–just to gauge their reaction. It helps him screen the right people for his cap table.

The Future of Relay: Building the Financial Command Center for Businesses

When investors look at Relay, they are betting on its vision. As Yoseph sees it, the fully realized vision of Relay is what they call the “financial command center” for employee-based businesses. The future of business banking, in his view, is structured in three distinct phases.

Phase One: Collaborative Banking

The first phase focuses on natively collaborative banking. This means providing essential banking features such as checking, savings, debit, credit, and payments, but with a robust user permission layer on top.

As Yoseph explains, imagine having a Relay account where you can invite team members with customized access levels. For example, you could grant someone full access with audit trails attached or restrict them to specific tasks, like depositing checks into a separate account.

This creates immense value by enabling seamless collaboration within businesses.

Phase Two: Integrated Revenue, Spend, and Payroll Management

Once the core banking infrastructure is in place, the next step is integrating revenue, spending, and payroll management.

This phase revolves around developing software that enhances key financial processes, such as managing income, bills, expenses, and payroll for SMBs. There are three major benefits to this approach.

First, it allows Relay to offer a combined product suite that traditional banks simply cannot compete with. Unlike large or small banks that struggle with software development, fintech companies like Relay have a clear advantage in this area.

Second, combining banking with workflow automation software—such as accounts payable automation—creates strong customer retention because of the significant value provided.

Third, gaining a more comprehensive view of an SMB’s financial data improves underwriting capabilities.

Historically, underwriting small businesses has been challenging due to limited data, but with better insights and a higher quality dataset, Relay could offer more favorable lending terms and develop an underwriting edge.

Phase Three: Accounting Integration and AI-Powered Finance Automation

The third and most transformative phase involves layering in a general ledger and building accounting software directly into Relay. By integrating these functions, businesses can automate financial workflows like never before.

The possibilities become even more powerful with AI. Imagine a system that can predict cash flow needs and automatically move money accordingly. If a payroll run is approaching and the system detects a shortfall, it could seamlessly transfer funds to cover the gap.

AI-driven optimization could also maximize interest earned on available funds, ensuring businesses make the most of their cash reserves. Many have talked about “finance on autopilot,” and with the right dataset and banking tools, this vision can become a reality.

Lessons for Aspiring Entrepreneurs

In retrospect, Yoseph believes in reframing every experience as a learning opportunity. Early in his journey, he was driven by a desire to prove himself, fueled by a chip on his shoulder.

Over time, he realized that shifting his mindset toward learning—rather than just seeking success—was a game-changer. Whether facing great moments or complex challenges, viewing every situation as a lesson allows for better decision-making and resilience.

As a founder, setbacks are inevitable. However, approaching them with the lesson-learning perspective allowed Yoseph to extract valuable insights that made him more prepared for the future.

In Conclusion

The future of Relay is about empowering businesses with smarter, more intuitive financial tools. As Yoseph and his team continue building toward this vision, they remain committed to innovation, collaboration, and delivering lasting value to their customers.

From navigating early-stage startup struggles to securing multi-million-dollar exits, Yoseph West’s entrepreneurial path is a testament to strategic thinking, resilience, and the power of relationships.

His story serves as inspiration for founders looking to scale their ventures and ultimately achieve successful outcomes.

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

• Yoseph credits law school for teaching him critical thinking, argumentation, and conviction—skills that later helped him in business and fundraising.
• He raised a Series A in just 10 days by cultivating long-term investor relationships and aligning on vision and values.
• His first startup, Vuru, was acquired by Wave through strategic positioning and relationship-building rather than just revenue numbers.
• Hubdoc grew from zero to 50,000 customers by focusing on distribution channels, product-market fit, and timing their acquisition with Xero’s cloud push.
• Relay’s vision is to become a financial command center, integrating collaborative banking, cash flow management, and AI-powered automation for small businesses.
• By deeply understanding SMB financial pain points, Relay built a solution that combines traditional banking with modern automation, making it a competitive fintech player.
• Yoseph’s journey highlights that reframing challenges as lessons fosters resilience, better decision-making, and long-term entrepreneurial success.

 

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