William Stern on Community, Jewish Values, and Leadership at Cardiff

William Stern is a finance entrepreneur and founder and CEO of Cardiff, a B2B financing firm operating in North America, Portugal, and Israel. He launched Cardiff in 2004 after seeing many small and lower-middle-market businesses struggle to secure timely, cost-effective capital. Stern emphasizes transparency in rates and margins, relationship-based underwriting, and “ethical financing with a soul,” often using phone conversations rather than purely automated decisions. He describes leadership as a series of consistent, small actions that compound over time. Inside Cardiff, he favours frequent check-ins over annual reviews to support employees as whole people and to protect trust with customers, applicants, and stakeholders.

Scott Douglas Jacobsen interviews William Stern, founder and CEO of Cardiff, about belonging, community, and ethical leadership in finance. Stern says Cardiff began in 2004 to serve businesses “locked out” of timely, cost-effective capital, using transparent B2B pricing and human, phone-based guidance. He connects Jewish ethics to reputation and legacy: do work you would be proud to describe to your family. Stern notes calls with owners can start adversarial because financing is their lifeline, so Cardiff adopts a Switzerland-neutral, facts-first stance. Jacobsen parallels this with Evidence-Based Medicine: evidence first, then values and preferences. Stern says leadership is consistent action that compounds over time.

Scott Douglas Jacobsen: Okay, so I’ve been interviewing a few people on this concept of belonging and community, and a lot of the people who responded to this pitch were rabbis, primarily Orthodox. So getting a business person is a little more interesting as well. From a business and entrepreneurial perspective, do you incorporate the concept of belonging and community when you think about the business ecosystem?

William Stern: Yes. From the very beginning, we were trying to build a community because when we started in 2004, we felt locked out. I had come from a large company that peddled financing to middle-market companies—think of them as having hundreds of millions in revenue—and they could obtain funding from several sources above the middle market. You would go to publicly traded companies that have the best access, but what is left beneath middle-market companies are the crumbs and leftovers of the market.

They are the forgotten souls of the business community. In large part, those folks were locked out of obtaining financing in a timely and cost-effective way. So we wanted to build this community.

We did not know how. It was one of those situations where you are learning to fly the plane at 10,000 feet. But we knew that to build a company with brand awareness and staying power—because we were not looking to be fly-by-night, make some money, and then sell pistachios the next day, like so many entrepreneurs do—we had to start with an ethos. That ethos was about community.

It was about doing right by people who were locked mainly out of cost-effective, timely financing, doing right by them, and having them spread the gospel of Cardiff.

It is similar to what you would find with the airline Southwest in the United States.

They have a similar ethos around community. Interestingly, you bring it up. They have a model—and I do not know to what extent they employ it in precisely these terms today—but it is often described as a people-first chain: the company takes care of its employees, employees take care of customers, and customers generate results for shareholders.

I learned that early on in my career. There was a Texas lawyer, Herb Kelleher, who co-founded Southwest with businessman Rollin King, and he wanted to do right by people. It was about building a community centred around a low-cost airline.

For the most part, they were among the first to achieve this at scale in the United States. In the face of Delta, United, American, and Pan Am—which ceased operations in 1991—Southwest helped popularize the low-cost, high-frequency model, and that was part of its ethos: building a community.

At Cardiff, we understood that at a very young age. We knew we needed to do right by people and have them serve as the mouthpiece for our marketing because we did not have the money for marketing.

That approach was taught to our employees. Our employees made sure to do right by our customers—or, more accurately, by the applicants. They ushered applicants through the process and gave them advice about their options and what they would do, empathetically, if they were in the business owner’s place.

Just because a business owner wants to apply for financing does not necessarily mean the timing, amount, or rate are right. So it was ethical financing.

It was ethical financing with a soul, which has been challenging to maintain in the age of AI, where computers make most decisions at most companies. We still use this old-school technique: we get on the phone with small business owners who need financing.

So I hope that answers your question.

Jacobsen: You operate in North America, Portugal, and Israel. There are significant Jewish populations in Canada and the United States. Are there particular Jewish values that you see as consistent across Orthodox, secular Jewish, and humanistic Jewish communities that you see infused into the ethos of Cardiff as well, especially when you are talking about ethical financing?

Stern: Financing is among the most ethical forms of business. The reason is that it is transparent—at least the type of financing we extend. We offer B2B financing, and the rate is apparent. There is no ambiguity about the margin for the bank or the financing company.

I used to work at Nordstrom. It is a North American clothing retailer. I worked there while in college, and we sold shoes. I remember thinking—this was twenty to twenty-five years ago—who could afford a shoe that costs $300?

At the time, I wondered what Nordstrom's margin was. I later learned they bought the shoes for roughly half that price. So they had about $150 in gross margin before paying the lease, employees, utilities, and everything else. The gross revenue was essentially $150 per shoe, and I remember thinking, "Is that ethical?"

If you fast-forward to today—and I will come back to your question—I want to talk briefly about ethics. About a year to a year and a half ago, the media broke a story about luxury goods marketed as made in continental Europe. The question was whether they were actually sewn and fabricated there, or made in Asia using cheap labour and then shipped to Europe, where labels like Louis Vuitton, Gucci, or Yves Saint Laurent were added.

What emerged was that some luxury brands relied on contractors in Europe that used exploitative labour conditions, including factories staffed by undocumented workers, often paid extremely low wages. In those cases, brands contracted out the production of items like purses, and the labour conditions were not ethical.

In business, it takes a lifetime to build a reputation, and a momentary lapse in judgment to lose it.

Coming back to your question about Jewish ethics—whether we are talking about ultra-religious communities at one end of the spectrum or humanistic Judaism at the other—there is an ethos of life that carries into business. You should not do anything you would not feel proud to tell your family about.

It does not matter whether you are a shoemaker or the founder and CEO of a company that finances approximately $2.5 billion a year. The legacy we are building is on full display to our families.

If we care about our children’s legacy—not just in terms of money, but in terms of name, culture, and identity, and yes, religion as well—then that legacy has to be built on a foundation of honesty. So yes, that is the answer to your question.

Jacobsen: When you and your employees get on calls with small business owners, what have you learned about community from them?

Stern: It generally starts hostile. It begins like a terrorist negotiation—between Hamas and some interlocutor—because the U.S. does not want to negotiate directly. Hence, you get an independent third party, maybe the UAE or something like that. There is never really an independent third party. But unfortunately, it does start hostile.

That is because small business owners are consumers. They are not large, faceless corporations where a CFO or controller gets on the phone and is emotionally detached from the financing. A consumer is emotionally attached to this financing because it is their lifeline.

They need the money for a reason—to solve a problem or seize an opportunity. If the process is not designed and executed with excellence, ease, and minimal friction—and if it does not meet their needs—it becomes a problem. It is never about what the company or we want. It is about accommodating the consumer.

Jacobsen: We’re all sublimating.

Stern: Yes, we are supplicating to the consumer. It starts that way. It begins like a terrorist negotiation, where it is cold outside and, to get them talking, you put a donut and a cup of coffee on the table as a way of saying, How can we appease you?

Jacobsen: A North American peace offer.

Stern: That’s right.

Jacobsen: Donut and coffee. Dunkin’ Donuts.

Stern: That’s right.

Jacobsen: A six-dollar deal.

Stern: That’s right. A six-dollar—what is the Canadian coffee company called?

Jacobsen: Tim Hortons.

Stern: Tim Hortons.

Jacobsen: It is funny. When I was a kid, I was on a soccer team, and one of the girls on the team was named Claire Horton. She had a dad named Tim, Tim Horton. No association. His name was Tim Horton, but he was not the Tim Horton. I do not even know if there is a “the,” but there was someone in my childhood.

Stern: There has to be.

Jacobsen: I would hope so, but I do not know.

Stern: Is there a hut that makes pizza? Was there an original Domino? I am just kidding.

Jacobsen: Was there an original domino? I mean, the company is going, and one had to fall. There had to be a domino. There had to be one that fell.

Stern: That’s awesome. I thought you were going to offer me one of those Tim Hortons cards that gives you free coffee for life.

Jacobsen: Someone offered me, when I go on my next war trip. It is all you get at the airport at a reasonable price.

Stern: Has anyone ever told you that you speak incredibly quickly?

Jacobsen: Yes.

Stern: That is a wild talent. Nurture that as best you can.

Jacobsen: I appreciate that very much.

Jacobsen: Often filtered through coffee, that is how it goes for me.

Stern: What was your question? What were we talking about?

Jacobsen: I have another question.

Stern: But if I can close the loop on this part, it starts hostile because they are consumers. They want what they want. They are business owners, often Type A personalities, and they are used to getting what they wish to or walking away—whether or not it benefits them.

That is just how they treat people sometimes. We try to paint a realistic picture. We act like independent journalists.

These are the facts. If it benefits you, you should do it. It stays very third-person. It only becomes first-person to the extent that the relationship permits.

If someone says, “I am not sure what I should do,” someone on our side might say, “Looking at your situation and your financials, if I were you, this might be interesting for these reasons—but you might not want to do it for these reasons.”

That independent, Switzerland-neutral attitude never seeks to take power away from the consumer. It gives them all the facts, all the options, even peripheral options they may not have noticed.

It gives them the information and allows them to retain their power to make the decision that benefits them—whether that is taking the financing or not. I just wanted to make sure I said that.

Jacobsen: I will add an addendum to that. There is an epidemiologist, probably one of the most cited academics in Canada, if not in the country’s history, named Gordon Guyatt at McMaster University. He co-founded Evidence-Based Medicine in 1991. One of his key collaborators has since passed away, but Guyatt is still alive. I have interviewed him many times.

A central principle of Evidence-Based Medicine is that you begin with the quality of evidence—the strength of what you are presenting to a patient, or in your case, to a client. Then you move to values and preferences. The professional says, “Here is the quality of evidence, but it is up to you to decide what you want to do based on your values and preferences, and which course of action fits those best.”

It is the wisest approach because it respects the individual's autonomy. If you try to force decisions on people, it becomes grating as an interaction anyway, and it is not wise for long-term trust or brand quality. He is a significant figure in medicine.

Stern: I will look him up. That is interesting. Thank you for sharing that.

Jacobsen: I do notice across disciplines and across people’s practices—professionally, culturally, and personally—that there are consistent threads. Sometimes it just takes a narrative to trigger the recognition.

Stern: That is great. I will look him up. I want to read more about that.

Jacobsen: Do you know the Gottmans at all? The Gottmans are the leading researchers on couples and marriage. One of their best-known findings is that the most significant predictor of divorce is the expression of contempt, primarily nonverbal contempt. That is essentially the death knell of a marriage. After that, it is usually a matter of time. If you watch interviews with John Gottman, he often pulls out a notebook and writes things down. I always think that says something about a person’s life practice.

Stern: Oh, like writing things down? Yes, that is funny.

Jacobsen: Mindful.

Stern: I am not a professor or a doctor, but there is a company in the United States called Baron Fig that makes these notebooks. I have an endless supply of them. I love them. I am always writing things down and dating the pages so I can reference them later.

It is definitely an old-school technique. My creative director, because I do a lot of marketing, tried to get me to use an app called GoodNotes on the iPad. I do not get the same feel. I am still stuck in the 1900s, as they say.

Jacobsen: It is tactile sensibility. Margaret Atwood, one of Canada’s most well-known authors, writes her books by hand and then types them out. People develop their own methodologies, and they stick with them.

Stern: That is awesome. That was a cool tangent. I appreciate that.

Jacobsen: So, about leadership: everyone is a leader in some sense, just at different scales. Some people struggle to lead themselves through their day—getting started, organizing themselves, functioning smoothly. Other people, like yourself, are leading companies that deal in billions of dollars.

When it comes to ethical leadership, what does that mean to you? How does leading others give you an added sense of responsibility and accountability—not just to the company, but to the people who depend on you? Accountability and responsibility to yourself, to the brand, and to the people who work for you.

Stern: Got it. I also have trouble waking up in the morning because I am human. Being human means waking up in a warm bed, which is terrific, and not wanting to get out of it.

I remember hearing an interview with Lex Fridman. He is often described as a podcaster, but he is also a scientist who hosts long-form interviews. He was interviewing Jeff Bezos. It was interesting to hear how Bezos starts his day.

He talked about waking up around seven, looking at his phone, having coffee, reading the news, answering some emails, and easing into the morning. It sounded very ordinary and genuine. You can contrast that with the inauthentic life you often see on social media.

Jacobsen: Inauthentic?

Stern: Yes, inauthentic. You see men in their forties or fifties who are perfectly sculpted, hairless, which none of us really are; and they wake up, wiggle their toes in the grass, jump into cold water, journal, and do all of this performative ritual.

None of it feels real. The word I was looking for is “curated.” It feels curated for social media. You were asking about ethos and what leadership looks like. Leadership looks like showing up. That is the core tenet of leadership.

Many entrepreneurs do not realize that leadership is not a philosophy. This is not like chiropractic philosophy. I once went to a chiropractor who started talking about philosophy, and I thought, “Wait, I was hoping we were going to talk about medicine.”

Leadership is not abstract. It is practical. It is about being present, showing up consistently, and taking responsibility.

Leadership is not a philosophy. Leadership is action. Generally speaking, leadership, at least good leadership, consists of small actions that compound over time and create wins for the company, the individuals who work there, and ultimately the stakeholders—the owners.

As for my mornings, since we were talking about Judaism, I start with a prayer. It is called the Shema. I say it every morning and again before I go to bed, but we are talking about mornings.

I say it, and then I thank God because I am genuinely thankful. That is not performative. It took me years to realize that I was grateful, but I am. I thank God for health, happiness, and wealth, in that order, for my loved ones, friends, and family, and lastly for myself.

Why, lastly, for myself? Because at this point in my life, I am forty-six years old, I need to be thankful for everything around me. They are my gravity. They keep me grounded, balanced, and in equilibrium, rather than spinning out of control.

I thank God for that, and then I start my day.

To answer your question about leadership: it consists of small actions. They can be good decisions or bad decisions, but they are made in a timely fashion. Those actions compound over time, creating momentum.

Physics applies here. Momentum is mass times velocity. Many business owners and leaders get this wrong.

Leadership cannot be done in silence. It is not a Buddhist monastery where you pray quietly in the hope of changing the world. I respect that tradition, and it sounds terrific, but that is theory. That is philosophy.

Leadership is not philosophy. Leadership is action.

As a leader, the best thing you can do, while keeping fiduciary responsibility in mind, is to keep taking positive actions to the best of your ability and allow them to compound over time.

I will leave you with this thought. One thing we do not practice at Cardiff is end-of-year reviews. We are not unique in that, but instead, we check in with our people.

Depending on the department, we check in constantly. “Always” is not a day of the week, not a month of the year, and not a holiday. We constantly check in with our people.

We want to understand how people are doing. How is your mother? How is your father? What is going on with your kids? What are you doing outside of work?

We do this because we are human. We are not trying to be their family. We are not trying to be their friends. We are trying to be human—humanistic in our approach—recognizing that everyone has fears, aspirations, and lives outside the company.

The company is a tool. We do not give an annual review to a screwdriver, but work is a tool. It is a tool that provides.

Jacobsen: Thank you very much for the opportunity and your time, Will.

Scott Douglas Jacobsen is the publisher of In-Sight Publishing (ISBN: 978-1-0692343) and Editor-in-Chief of In-Sight: Interviews (ISSN: 2369-6885). He writes for The Good Men Project, International Policy Digest (ISSN: 2332–9416), The Humanist (Print: ISSN 0018-7399; Online: ISSN 2163-3576), Basic Income Earth Network (UK Registered Charity 1177066), A Further Inquiry, and other media. He is a member in good standing of numerous media organizations.