Yoseph West On Raising 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.

Yoseph’s latest venture, Relay, has attracted funding from top-tier investors like Bain Capital Ventures, Better Tomorrow Ventures, Amaranthine, and Industry Ventures.

In this episode, you will learn:

• 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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About Yoseph West:

Yoseph West has a diverse work experience in the financial technology industry. Starting in 2010, they were the Co-Founder & CEO of Vuru, which was acquired by Wave Accounting.

Yoseph then joined Wave in 2012 as the Director of Product Engagement and Product Manager of Wave Personal. In 2014, they were the Principal at Growth+Data and Head of Marketing at Hubdoc.

Hubdoc was later acquired by Xero for US$70m. Yoseph then became the Owner of Kaizen Properties in 2016 and, most recently, the Co-Founder & CEO of Relay Financial in 2018.

Yoseph West received their LLB from Durham University in 2008 and their LPC from BPP Law School in 2009, both in the field of law.

Yoseph specialized in Business Law, Equity & Debt Finance, Private Acquisitions, and Civil Litigation during their time at BPP Law School.

Connect with Yoseph West:

• LinkedIn
• Crunchbase
• TheOrg
• RocketReach

Read the Full Transcription of the Interview:

Alejandro Cremades: All righty. Hello, everyone, and welcome to the Deal Maker Show. Today, we have a really amazing founder. We’re going to be talking about all the good stuff we love to hear: building, scaling, financing, and even exiting. I find this conversation quite inspiring. We’re going to touch on topics like the early days of building a business and how to navigate tough moments.

Alejandro Cremades: Perhaps we’ll also discuss rounds of financing, like in their case, their Series A, which they closed in just 10 days—kind of crazy! We’ll also cover their Series B and how that came together. There’s a lot of good stuff I think you’re all going to enjoy. So without further ado, let’s welcome our guest today, Yoseph West. Welcome to the show.

Yoseph West: Thanks, Alejandro. It’s great to be here.

Alejandro Cremades: Let’s take a walk down memory lane, Yoseph. You were born in London, UK, but eventually, you grew up in Canada. Walk us through what life was like growing up for you.

Yoseph West: Yeah, growing up in Canada, I lived in a small town outside of Toronto. In many ways, it was an idyllic and beautiful place. I grew up with English and Persian parents, and in that context—being in a smaller town in Canada 20-plus years ago—we were part of a smaller portion of immigrant families.

Yoseph West: Growing up in that environment involved a lot of learning and a sense of not quite fitting in, but also sort of fitting in. Canada was going through a lot of change at the time and continues to evolve. But what an amazing time to be in Canada! As a place to grow up, its ideals, values, and the melting pot it represents provide a unique lens on society and how to build a life.

Alejandro Cremades: That’s incredible. Being raised by immigrant parents must have influenced who you are today.

Yoseph West: Yeah, 100%. I often joke with family and friends that I was raised with a bit of a problem with authority or a tendency to question things. I was definitely that kid in school who would—perhaps annoyingly—correct the teacher without caring much about the consequences. I’m sure that was very frustrating for my teachers.

Yoseph West: But as a foundation, my parents encouraged me to question the world around me. After all, the world was built by people just like us. There’s that famous Steve Jobs quote that encapsulates this idea, and I believe it to be extremely true. When you recognize what’s possible and direct your energy toward something while questioning the status quo, it unlocks a lot of potential.

Alejandro Cremades: That’s amazing. One thing I found interesting is that you got bored with high school quickly. It seems like a pattern in your education—whether high school or law school. What’s going on with getting bored with education so fast?

Yoseph West: I don’t really know what it was. I was actually talking to someone about this just last week. If I had grown up today, I’m pretty sure I would have been diagnosed with ADHD. I would get bored in school because I didn’t find it as challenging or engaging as I wanted it to be.

Yoseph West: So, I figured out a way to complete high school in three years. I was raised by English and Persian parents, and my career options were presented to me as becoming a doctor or a lawyer—common choices in many immigrant families. Engineering wasn’t really presented as an option for me.

Yoseph West: I wanted to become a lawyer as quickly as possible because the idea of spending four years in undergrad and then three years in law school sounded mind-numbing. So, I figured out how to get through high school quickly and then realized that in the UK, you could get an LLB in three years. So, I crossed the pond, got my degree, and was done by the age of 20.

Alejandro Cremades: Even though you got bored and didn’t want to practice law much, I’m sure earning that degree gave you valuable perspective and understanding, particularly on the business side of things.

Yoseph West: Yeah, absolutely. I’ve spoken to many other businesspeople with similar backgrounds who never went into law practice. What law school fundamentally teaches you is how to take a set of information, build an argument, and develop a perspective with conviction.

Yoseph West: That’s essentially what you do in law school every day—reading cases, analyzing perspectives, and forming your own conclusions. When you’re building something from nothing, there’s a lot of ambiguity and uncertainty. You have to piece things together in a compelling way for the market, your team, and investors. That training has been incredibly helpful.

Alejandro Cremades: That’s amazing. So once you got your law degree, how did you transition into the business world? How did you get together with a group of friends and start working on ideas?

Yoseph West: Coming out of law school, I wasn’t too excited about practicing law. I had done some summer jobs at law firms and wasn’t enthusiastic about the work.

Yoseph West: I wanted to start something. Half of my family are lawyers, and the other half are entrepreneurs. I started brainstorming with friends, exploring different ideas—offering travel experiences, making a virtual greeting card—it didn’t really matter. We were just trying to find something.

Yoseph West: Eventually, we landed on a stock research platform that was free and ad-supported. It wasn’t a great business model, but we were in our early 20s, and we just worked really hard. We raised $25,000 CAD and eventually got aqua-hired by a company called Wave, a financial services platform for micro SMBs.

Alejandro Cremades: What is the process of being aqua-hired like? Most people are familiar with acquisitions, but how does an aqua-hire work?

Yoseph West: Most acquisitions happen as a result of long-term relationships. When we were building our startup, I saw similarities between what we were doing—a free financial app with ads—and what Wave was doing. They had raised much more capital than we had and were further along.

Yoseph West: I reached out to their founders, saying, “Hey, we’re doing something similar for stocks. I’d love to learn from you.” They spent time with us, and I remember one of them jokingly said, “Maybe one day we’ll buy you.” I tucked that away in my mind.

Yoseph West: Later, when we were raising a pre-seed round, we weren’t excited about the partners at the table. We questioned whether this was how we wanted to spend our time. So, I went back to the Wave founders and asked if they were serious about an acquisition.

Yoseph West: They grilled us pretty aggressively, evaluating not just our skills but also our character—how we treated people, how we handled negotiations. Eventually, we closed the deal when I was 23, and I turned 24 right after. It was exciting, and I learned a ton. That experience was foundational for everything I’ve done since.

Yoseph West: But I would say that was a critical moment. And then I can jump into the Series A if that would be a good lead-off.

Alejandro Cremades: Go ahead, my friend.

Yoseph West: Yeah, so the backstory on the Series A—I mentioned the seed round, where we had Bain put in a little bit of capital. The person involved there was Carrie Goman, who previously ran Capital One Small Business Bank. She was actually the sponsor for the Hubdoc acquisition by Xero.

Yoseph West: She had a long-standing relationship with us and a deep understanding of our space. She had seen all the SMB Neobank deals and believed that we were building what should actually exist—an SMB Neobank designed for businesses, specifically small businesses in the heart of America with employees. When Bain wrote that lead-generation check, we invited her in as though she had written a much bigger check.

Yoseph West: We invited her to our board meetings, and as we were going through that process—since we raised the seed round in October 2020 and closed our Series A in April 2021—it was a heady time. Another investor had come out of the woodwork, wanting to preempt Relay. We were working our way up to better terms that we were more excited about and got them to a place where it felt fair based on where we were.

Yoseph West: Once we had that, I called Carrie and said, “Hey, you kind of joked about Bain doing our Series A—do you want to do that?”

Yoseph West: And within 10 days—actually, from Monday to Monday—it happened. I called her on a Monday evening, we pitched the partnership the following Monday, and we had the term sheet in hand that evening. Carrie is a powerhouse in terms of what she has accomplished, so it felt like a great place to start.

Alejandro Cremades: That’s amazing. When it comes to fundraising, what would you say has been your biggest lesson?

Yoseph West: I think each round comes with its own set of challenges. The one thing I believe to be true is that an investor has to believe two things:

They have to believe in your vision of the world and what the future will look like.

They have to see a bit of themselves in you. They need to believe in you as a person and feel a connection.

Yoseph West: When those two things come together, a deal can happen. For us, we are in it for the long haul and want to bring on investors who match us culturally and align with our values. That’s really important.

Yoseph West: When I get on fundraising calls, I amp up some of my own idiosyncrasies and quirks just to see how people respond and engage. Generally, it’s received well, but sometimes it’s not. That, in itself, is informative because if it’s not a good fit, it might not be a great relationship. As we all know, having someone on your cap table is like a marriage—we want to build something long-term.

Alejandro Cremades: Absolutely. Now, speaking of long-term vision, let’s talk about where the investors are banking on. If you were to go to sleep tonight and wake up in a world where Relay’s vision is fully realized, what does that world look like?

Yoseph West: How many years out am I, Alejandro? One year? Ten years?

Alejandro Cremades: Let’s say five years.

Yoseph West: Okay, so let’s talk five years out. Fundamentally, what we are building is a financial command center for employee-based businesses. We see the future of business banking unfolding in three phases:

Natively Collaborative Banking – Checking, savings, debit, credit, and payments with a user-permission layer on top. If you had a Relay account, you could invite me in and grant different levels of access, from full access with audit trails to just allowing deposits in a separate checking account. It creates significant value in terms of collaboration.

Integrated Revenue, Spend, and Payroll Management – Once you have the core banking layer, you build software around key areas of the SMB wallet: income, bills, expenses, and payroll. This delivers a combined product suite that traditional banks can’t compete against. Big banks and small banks alike can’t build software in the way a fintech company like ours can. Additionally, two sticky products—workflow automation software (like accounts payable automation) and banking—create a lot of customer lock-in by delivering so much value. A more complete data set also improves underwriting for small businesses, making lending terms more favorable.

General Ledger & Accounting Integration – We integrate accounting software directly into Relay. If we can achieve all three phases and combine them with the power of AI, we can enable automated cash flow management. For example, if a payroll run is coming up and the system detects a $10,000 shortfall, it could automatically move funds accordingly. AI-powered automation could optimize savings and maximize interest earnings in ways that weren’t possible before.

Yoseph West: People often talk about “finance on autopilot.” I believe that’s achievable, but only if we build the full data set and the right tools around the core banking experience.

Alejandro Cremades: Now, let’s put you into a time machine and take you back to the moment when you got fed up with law school—maybe around 2010—when you were considering doing something new. If you could give your younger self one piece of advice before launching a business, what would it be and why?

Yoseph West: Ooh, just one piece? There’s so much advice I would give!

Yoseph West: The biggest unlock for me on this journey has been shifting my mindset. Initially, I was driven by a chip on my shoulder and a need to prove myself. Over time, I reframed everything as a learning experience.

Yoseph West: Whether it’s a great moment or a terrible one, when you reframe it as learning, it changes your perspective and helps you operate better in the moment. As a founder, bad things happen—that’s part of the journey. If you reframe those experiences as “I earned the right to learn this lesson,” then you can take it, absorb it, and be better prepared for next time.

Yoseph West: I wish I had known that when I was 20 or 25. It would have made a huge difference.

Alejandro Cremades: That’s incredible. I’m sure a lot of people listening are inspired and wondering how they can reach out and learn more. What’s the best way for them to connect with you?

Yoseph West: You can follow us on Twitter—@bankwithRelay—or on X, I guess I should say. You can also follow me on X @ycwest or send me an email at yo****@re*****.com.

Alejandro Cremades: Fantastic. Well, Yoseph, thank you so much for being on The Deal Maker Show today. It has been an absolute honor to have you with us.

Yoseph West: Thank you—it was great to be here.

*****

If you like the show, make sure that you hit that subscribe button. If you can leave a review as well, that would be fantastic. And if you got any value either from this episode or from the show itself, share it with a friend. Perhaps they will also appreciate it. Also, remember, if you need any help, whether it is with your fundraising efforts or with selling your business, you can reach me at al*******@pa**************.com“>al*******@pa**************.com

 

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