Five questions with … Fair Chief Executive Brad Stewart

Fair Chief Executive Brad Stewart

Since taking the wheel at leasing app Fair in May 2020, Chief Executive Brad Stewart has set his sights on growing the company’s product offering while making Fair profitable.

As Fair’s new CEO, Stewart led the launch of two- and three-year lease options in the fall, a program designed to supplement the used-car app’s no-commitment, short-term leasing options.

This month, Fair partnered with the online lending marketplace LendingTree to reach more consumers who desire short-term leases. LendingTree allows digital platform users to instantly pre-qualify for flexible lease payments with Fair. In the first few weeks, LendingTree brought more than 1,000 pre-qualified customers to Fair.

In the driver’s seat, Stewart says he “likes everything” about his 2017 BMW X5 – the color, the rims and the look. “It’s super-fast and comfortable; the perfect combination of size, height, everything,” he told Auto Finance Excellence.

AFE asked Stewart five questions to learn about his goals for Fair, advice that has helped him achieve success in a fluctuating industry, and a surprising fact his colleagues may not know about him.

AFE: What are your company goals in about 10 words or less?

BS: That Fair becomes the global go-to destination for used-car transactions.

AFE: What is your favorite piece of leadership advice you ever received?

BS: Probably to think downrange and to understand the lasting dynamics of your actions — not just tomorrow, but over the long term. Always be aware that the decisions you make have an energy that impact everything they touch.

AFE: Who has had the biggest influence on your career?

BS: My wife, Brady. We’ve been together about 17 years now and were both at McKinsey at the same time. So, not only does she know me better than anyone on the planet, but she’s also the best human being I’ve ever met in terms of values and character. Of course, it doesn’t hurt that she happens to be a global leader in e-commerce (at Levi’s). But more broadly than her domain expertise, she’s just a very intuitive thinker who has a sixth sense for how things play out and makes really good decisions. She’s always been there for me when I’m facing an important inflection point and want an outside perspective.

AFE: What do you think is the most underrated lending trend?

BS: I think, over time, the processes that go into lending will become much more individualized to the point that everything about you will be known to whoever’s advancing you money. Some of this will be data-driven — bank account information, your credit history. But I think there will also be a layer of psychographic considerations involved: your earning potential, impulse control as shown through your spending habits, and even the kinds of activities you’re paying for.

Right now, we have a system where two people with very different approaches and attitudes about risk might, by our current imperfect understanding of their financial picture, get lumped into the same risk profile. As a result, one might get a better deal than they might have gotten otherwise, while the other gets a worse one. I could see a system that better leverages identified behavioral attributes to create a more specific picture of each loan candidate. It might sound a little creepy — and I don’t know if all of us necessarily want all that information out there — but it will no doubt be a benefit for the good actors who are essentially subsidizing more risky candidates in the current lending system.

AFE: What’s something your employees would be surprised to learn about you?

BS: Maybe that I have my pilot’s license? It’s been an on-again, off-again thing in my life. When I was 19, I was in college and sort of bombing a little bit. I was originally in an engineering program before I switched to business, and I wasn’t enjoying it. I was actually feeling pretty trapped. So, one day I just walked over to the local flight school and signed up. I did all of my qualifications, did the written test, and got all the way to my check ride — then basically ran out of money.

When I was 29 or 30 and further along in my career, I started feeling really unsettled by this piece of unfinished business behind me. I found a flight school in the Bay Area where I lived, and restarted the whole thing. Every Tuesday and Wednesday night, I would drive 45 minutes, fly, and be home by 9 or 10 o’clock. And then every Saturday or Sunday, I’d be back out there the entire day. I did that for nine months, then finally took my check ride and got qualified. It was really fun, but it’s one of those things, like golf, that goes away if you’re not doing it all the time. Plus, it’s very time-consuming. Just to go do a quick fly-around is four or five hours of your day — you get out there, you pre-flight the plane, do all the weather checks, file some stuff with the FAA. With a couple young kids and running a company, I just don’t have the time and energy to do it right now. Maybe when we get our kids off to college, I’ll jump back in.

Auto Finance Innovation Summit, the premier event for technology in auto finance, returns March 16-17, 2021, as a virtual experience. The virtual experience will offer the quality networking and education of past events, all through an online platform. To learn more about the 2021 event and register, visit 

Exit mobile version