An Interview With CSTMR’s Founders: Rory Holland and Jack Macy

An Interview With CSTMR’s Founders: Rory Holland and Jack Macy

CSTMR’s founders Rory Holland and Jack Macy

In today’s rapidly evolving financial services landscape, trust and authenticity have emerged as essential elements of building a successful brand.

Here’s a hard truth: this wasn’t always the case.

It’s not that integrity didn’t matter, it was simply taken for granted by the average financial services consumer.

As technology continues to advance at an unprecedented pace, we (the collective we) are more empowered than ever to weigh our options and consider what truly matters to us in a bank, a lender, an investment firm, or any other financial services provider. 

This complex landscape raises pivotal questions about consumer preferences and what really drives people to select one financial services organization over another. To help shed some light on the intricacies of this trend, we are joined today by CSTMR’s co-founders, Rory Holland and Jack Macy, for an extensive Q&A.

With decades of collective experience in financial services and fintech marketing, Jack and Rory are uniquely positioned to provide us with a valuable lens through which we can examine how fintech brands can build lasting (and profitable) relationships with consumers.

Let’s dive in.

The Beginnings

Q: What’s your professional background?

Rory (R): I’ve always been an entrepreneur at heart, and I enjoy helping leaders build successful companies and memorable brands. Through CSTMR, I get to leverage my 20-plus years of financial marketing experience to help build successful fintech and financial brands.  

My first agency, which I started in 1994, was a branding and licensing firm, and it propelled me into the agency world. In 1998, it was acquired and my new agency did work for General Motors Acceptance Corporation (GMAC), which was my first experience with a financial brand—and my first experience in financial services marketing.

They were very interested in how “digital” could help them expand and grow their portfolio, which opened the door to a variety of new strategies and technologies, such as paid search and email marketing.

From 1998 forward, I became more and more integrated into the financial services sector, working with the major credit card issuers, lenders, and credit bureaus.  

And that’s what brought me to, where Jack [CSTMR’s co-founder] and I met—meeting him was the greatest thing that happened to me professionally.

Q: Jack, what about you? 

Jack (J): I actually worked in education until I was into my thirties, and then went back to school for design and web development.

I had a few jobs where I was a designer or creative director, some in-house and others with agencies.

All of those jobs I had along the way were couched, in one form or another, in marketing. So, like Rory, I was exposed to a variety of strategies that emerged over that period of time. For example, when email marketing first popped up, I was figuring out how to build and send HTML emails before most people knew such a thing was possible. 

I helped companies build their first websites in rudimentary HTML, before WordPress and other content management systems appeared. So I was exposed to a lot of different aspects of “modern” marketing. I also had some excellent exposure to branding, advertising, and messaging strategy along the way that helped shape how I view marketing today.

My first experience in financial services marketing was when I was hired as a designer at in 2009. I was promoted to Product/UX Lead as I had a good UX mind and background, and spent the last couple of years there as VP of Product and Design.

When the real estate bubble burst, I saw the impact it had on everyday people. What we witnessed became one of the main motivators to start CSTMR with Rory: to provide good products that truly drive financial wellbeing and help people move forward financially.

Q: So, how did CSTMR come to life?

J: I never really had an entrepreneurial bug—maybe I was a little risk-averse when I was younger—but I’d had enough experiences where I felt like I could do things better and wanted to take the leap.

I was tired of having somebody lording over me, and I’d received enough positive feedback throughout my professional journey to finally say “You know, I can do this. I’m as much of an expert as those people over there.”

Rory left a year or two before I did, but we kept in touch. He was doing his own consulting stuff, and I was looking for new opportunities for professional growth. Without a whole lot of promise of any income at the start, I quit my job to start CSTMR with Rory.

Rory and I saw that we had very complementary skill sets: we both knew our own disciplines, but we also overlapped enough that we understood what we each one did within their digital marketing wheelhouse. 

We had Rory’s lead generation, sales, and multi-channel customer acquisition experience, and my background in design and product technology.

So, by combining forces, we created a strong foundation from which to build an integrated agency ready to meet the needs of the digital age—a combination of strategy and execution tailored to financial services organizations.

With the advent of new and innovative technologies, we began to focus more heavily on fintech.

Keep in mind that 10 years ago fintech wasn’t a thing; it was the very beginning of fintech. In fact, just this morning I was reading the Empire Startups newsletter, which was created just after we started CSTMR. 

R: Do you remember that we went to a couple of the Empire Startup expos? We have some really stupid pictures of ourselves at that [laughs].

At this time, I had already done a lot of lead generation work in financial services. And I saw that the breakdown between leads and customers was a pretty big chasm for a lot of companies. So our name—CSTMR—was our way of saying that we are obsessively focused on the audience and customers, from customer acquisition, to retention, to full adoption.

Back then, fintech and financial services wasn’t a sexy place to be in, so that made us stand out. We had a broader view of what it meant to build a brand focused on acquiring customers at scale, in the fintech and financial services space.

In other words, our approach was and still is full funnel: customer acquisition through excellent branding, thoughtful design, and effective campaigns that’s truly holistic. CSTMR is about building a relationship between a brand and its target audience.

J: We adopted a consultative mindset that we felt that could really help people. 

Whether we are talking about a fintech or a traditional financial services organization, we have learned that our customers don’t want a production shop. What they want and need is a partner, one who’s going to tell them when they’re wrong and make recommendations that might be a bit hard to swallow.

For us, a real agency “partner” is one who’s honest and open with you, even when it’s not necessarily in their best interest. We prefer to dive into the trenches with them to brainstorm and solve their business problems. That’s how you build a foundation of trust.

The Vision

Q: Jack, you mentioned having frustrating experiences and wanting to do things better—what’s your approach to building a team?

J: To begin with, we rarely hire junior-level people

At CSTMR we hire people with at least five years of experience. We don’t want to hand-hold. We want to hire people who are self-motivated, who have their own drive to do things well and with purpose. Maybe they even have a bit of their own entrepreneurial spirit.

When we were figuring out our business model for CSTMR, we imagined it like a platform for independent contractors looking to exit the customer-acquisition rat race, who wanted a little bit of human interaction, and wanted to be part of something bigger or share success.  

We worked like that for a while and then we realized that, stability wise, it was just a better route to at least have some full-time employees. These individuals are a part of the core CSTMR family, but they are also empowered to work in a way that allows them to explore ideas, be innovative, and reach their full potential. 

R: I loved the idea of leveraging technology to build a community of folks who are all like-minded, and want to do great things—that’s where that collaborative notion of CSTMR came from. 

When we first interviewed David Moore [CSTMR’s Creative Director], we talked about that feeling of loving what you do, but feeling a little lonely sometimes, isolated—wanting to feel like a part of something.

CSTMR was born out of this philosophy. It’s the reason why we chose to be independent and have folks all over the world work with us, rather than limiting the company to just looking for talent in the San Francisco area.

J: Exactly. While we did start CSTMR in San Francisco, as we both lived there, it quickly became untenable as we were bootstrapping the agency. 

It was the very beginning of video conferencing, as far as the technology being accepted and integrated into business. Technology quickly allowed us to fully invest in the mantra of “Let’s find great people, wherever they are.” 

We focused then—and still do now—on hiring people not because of location, but because of quality. Back then, it was a novel concept. Plus, I hated the commute [both laugh].

R: When it comes to building an agency, or any business, our experience has taught us that there’s a right and a wrong way to do things.

The traditional agency model was more or less “take anything you can get, and do the best you can with it for as long as it lasts.” That’s the wrong approach, and it’s for that exact reason that we don’t work with just any company.

Since the very beginning, Jack and I have adopted a tongue-and-cheek mantra that is at the heart of how we think us humans should interact and treat each other—we don’t work with ***holes

We’re very clear about the kind of companies that we want to work with, and how we want to work. There are plenty of companies that only want to make a profit. Of course, there’s nothing wrong with profit—that’s how the world works. But we believe that we can make a positive impact on this world by helping our customers reach profitability, the right way. 

This principle has led to great business relationships as well as a happy, inspired team. 

J: Absolutely. Life’s too short to spend your time working with folks who you actually dread working with every day. That principle can be applied to your colleagues and company, but definitely for the customers you have, too.

At the end of the day, our clients are motivated by the mission to help solve a real problem. Of course, they are also interested in the profit—and that’s okay.

The Mission

Q: In your experience, why do consumers choose one financial brand over another? 

J: Go back 50 years, or less, and banks were some of the most trusted institutions, particularly the community banks, which is almost what everybody used at that time.

Now, the trust has shifted in a very different direction. The rise of mobile devices and apps in the past 15-20 years has dramatically shifted our perspective of financial services.

The generation that’s below 40 is far more skeptical of a traditional bank than of a brand new, unproven financial app. They are far more trusting of something like Venmo, as soon as it came out, than putting their money in an online savings account with a bank they’ve never heard of.

Also, the existence of fintech is only realized because of the potential national and global reach that it affords. Starting a fintech company that focuses just on customers in Lincoln, Nebraska, or any community, is going to be very hard unless you can make a case for that business model. [Jack is from Lincoln, Nebraska]

The internet was obviously a watershed moment. Mobile devices was another one, then social media. These technologies built on each other and allowed financial services to not only reach a broader market, but better serve that market. 

As we continue to move deeper into the digital age, hopefully there will always be a strong balance between things financial services organizations do locally, and the efficiency and convenience of something that is technology based, which can be global.

Also, trust is a major factor. 

Here, fintechs are constantly preaching about transparency. They also need to differentiate their brand. And I think the more genuine that brand can be, the more likely they are to build trust.

But they also need to be reliable in their actions and with their technology. If you use an app and it consistently does what you need it to do and you don’t have any problems, that builds trust as well. 

And then there’s the promise they make. 

Almost all financial services organizations have a mission, but how good are they at bringing it to the forefront? People need to be able to easily understand it, see it, and then choose them because of that.

Q: You both mentioned “trust” a few times—do you think there’s a trust crisis in financial services?

R: Trust in the financial system is imperative for society to function effectively. We trust that financial institutions have our best interests in mind, not just profit, but that’s not been the case in recent years. 

The financial crisis of 2008/2009 was an example of how the system can fail consumers, and people still haven’t forgotten all the bailouts. 

J: In the financial services industry, there has been a long string of activities, actions, and legal issues by financial entities that the general public feels just go unchecked.

In 2008/2009, banks got these massive bailouts that they didn’t have to pay back. People see that a $500 billion company got a bailout of a few billion dollars, while the average person had mortgages that were unsustainable, and they were not bailed out.

A lot of people lost their homes, lost a lot of asset value for themselves personally—it was a very pivotal moment. 

I think there’s also this notion of fiduciary responsibility

Fintechs, and financial services companies in general, are responsible not only for truthful interactions, but giving the best advice to their customers regardless of how it impacts them as service providers. Many stakeholders in the financial services industry don’t take this responsibility seriously, and I think that’s still a problem.

R: As Jack mentioned, 2008/2009 was a difficult time. We lived through it while we were building and seeing the fallout from the mortgage foreclosures and the impact on consumer credit.  

That was a time where the mortgage industry lost its way and cost many people their homes.

The Great Recession bailouts are a perfect example. Vast amounts of money went to giant corporations as a bailout, while the average American lost big.  

Meanwhile, the average American continues to struggle. That’s why establishing and building trust as a financial brand is critical. 

But building that trust, as a financial brand, has to be authentic; it has to be genuine and real. 

That’s why we, CSTMR, evaluate and choose our clients and the brands we support so carefully. We could be twice as big right now but choose not to take on just any customer. We pick the best ones out because we want to support and promote our mission and theirs: to help do good things in the world.

Looking Ahead

Q: To finish, how do financial services companies rebuild the trust that has been lost?

R: Trust is a hard thing to earn, and easy to lose.

People want to work with authentic, trustworthy brands that put them first. The younger audiences are searching for new ways to save, and invest their money—cryptocurrency is a recent example. Fintech provides an opportunity for financial institutions to better serve customers, and step up, putting customers first, and offer new, unique ways to invest and engage in building financial independence. 

It’s important for companies to strive to serve customers well, whatever form that takes for their business. We love helping leaders build trustworthy, successful brands and businesses, putting customers first in their product and marketing planning.  

Life, like building a multi-million dollar brand and business, can be messy—there are lots of factors at play, but there’s a method to it. At CSTMR, we love to help leaders navigate the complexities and develop a reputable, scalable business that serves customers well and makes a positive impact on the world.

To me, that’s the key. Work with good people who seek to do good things the right way and make a positive impact.

J: We pass on many potential clients. 

We have a lot of conversations with people and we say no to way more than we say yes to, because what they do doesn’t align with what we want to put our energy and expertise toward.

And that’s how we started CSTMR: we don’t want to market random products and help businesses grow for no clear, larger benefit. We work with customers who also have the best interest of consumers in mind

The future of financial services looks bright, it’s simply a matter of being genuine and doing right by your customers. 

To learn more about CSTMR, schedule a call with Rory.

Picture of Brendan Bresnahan
Brendan Bresnahan

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