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Brad Stewart of Fair: “Simplicity breeds results”

Simplicity breeds results. It means recognizing that you can only do a handful of things really well and that you must always have the alignment, focus and conviction to say no when something starts to drift outside of that zone. Just think of when you come home with a product from Apple. There’s no gigantic […]

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Simplicity breeds results. It means recognizing that you can only do a handful of things really well and that you must always have the alignment, focus and conviction to say no when something starts to drift outside of that zone. Just think of when you come home with a product from Apple. There’s no gigantic manual or flashy box or sales brochure. The packaging is basic and functional, the instructions are sparse and intuitive — and all of this stems from an organizational focus on simplicity. In successful companies, this kind of thinking ripples through everything — from how you communicate with customers to how your product looks to your own internal priorities. It’s a code I try to live by whenever I feel myself getting out of control or enticed by some new initiative that sounds really cool on paper. You have to constantly remind yourself that the human mind is cluttered. We’ve all got countless thoughts floating around in our heads at every moment. You have to cut out anything that doesn’t directly contribute to what you do well.


As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Brad Stewart, CEO of used car leasing platform Fair. The company lets users get a pre-owned car on the web or the company’s app and choose how long they drive it — either month-to-month or on a 2-year or 3-year lease. Stewart came to Fair after serving as CEO of XOJet, a leading on-demand private aviation services platform. Before joining XOJet as its president in 2010, Stewart was an executive with Parthenon Capital Partners, and prior to that worked at McKinsey & Company.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Sure. I found my way to Fair a bit indirectly via my previous experience at an aviation startup, XOJet, where I spent five years as CEO. Both companies are focused on finding efficient, new ways to deploy large transportation assets in a way that better suits consumers. And I joined both during interesting inflection points in their early growth when the focus shifted from iterating on the fundamental idea to scaling for the long-term in a sustainable way. But really my path is much more deeply rooted in a love for systems — in particular business systems — which I started cultivating when I was still in college. With a bit of serendipity and luck, I was recruited to be a management consultant, and that really started a long-term journey into how things fit together — from companies to entire industries. From that, I developed a real preoccupation with transformation. I love the idea of taking a good idea that has maybe lost its way, and being part of a team that catalyzes change and ultimately produces something out of it that works for both consumers and investors. After spending my 20s in consulting, I went into private equity where I fell in love with turnarounds. I’ve been part of five or six of them at this point and I find them totally exhilarating. It’s an opportunity to stand in a gap and really be accountable where what you do — your decisions and your actions — really have an outsized impact on the future.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

I think Fair is a disruptive company in that we’re out to transform not only how someone gets a car, but how they drive it. And for sure there’s no industry riper for disruption than automotive. It’s the largest consumer product category and one that’s burdened by a troubling level of inefficiency. The transaction itself is oftentimes clunky and uncomfortable, and it leaves the consumer at a real disadvantage in terms of having to negotiate and navigate with no real leverage or understanding of the processes they’re being subjected to. But, to be honest, Fair’s mission has nothing to do with focusing on being disruptive. We simply want to create a consumer automotive experience that’s beautiful and simple from beginning to end. We want to make getting a car as seamless and straightforward as any of the other services you order up on the web or your phone — where you pick what you want, you make the payments you see on the screen, and you use it for as long as you need. That concept is disruptive in the industry for sure. But to the average car shopper, that’s simply the way things should be.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Well, I think the funniest one I can think of is sending around the wrong dial-in for a conference call back in the day. Instead of the 800 number for the call-hosting service, I sent around an 877 number for, let’s just say, a pay-by-the-minute service totally unrelated to our purpose that day. And while I think the business model of the company behind that 877 number was predicated on people making this exact mistake, it didn’t make it any less embarrassing — especially since our consulting client was dialing in to the call. I don’t know if it’s the biggest business lesson I’ve ever had, but it was certainly a good reminder to be precise in my language and check the details. It’s very easy to get distracted by our texts and our emails and Slack and our newsfeeds, but you still have to pay attention to the little things. And that experience really caused me to double- and triple-check anything being sent externally — particularly if it’s going to a client.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

Well, we’re all a function of our community, right? And I’m glad to say I’ve been blessed with some truly amazing mentors. Chris Hsu is definitely one that stands out. We met early in my career at McKinsey. We were in the same office, but we focused on different sectors. He was in retailing with clients like Best Buy, and I was in financial services, and logistics. So while we didn’t overlap professionally, I just really admired him. He’s a guy who’s not afraid to be afraid to speak the truth, which has led him to take on a lot of intense challenges in his career, from being COO at Hewlett-Packard Enterprise, to being on numerous boards, and now even running his own startup (Zibo). He’s selfless, generous with his time and he really thinks about things. With mentorship, it’s easy to show up and clock the time. But to really be a great mentor, you need to listen, you need to ask probing questions, and you need to really try to understand the other person and the uniqueness of their situation. I think too many mentors basically try to project their own experiences onto other people, which is really tone deaf. I think what Chris does really well is that he’s humble and doesn’t try to apply his situation to yours. I know every time I talk to him, I feel energized and heard and I really appreciate his guidance. And I know for a fact I’m not alone, as he’s had a really profound impact on so many people’s lives.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

Sure. Like you alluded to, disruption has a mostly positive connotation in my mind in that it represents challenging the status quo in some game-changing way. And I think you’ve heard the term “disruption” more in the past decade or so because there’s so much information and technology that enable it. If you’re an industry challenger looking to shake things up today, there’s likely a road map and no shortage of tools that can help you do that. But I think all of these capabilities could have an unattractive side if they’re used to create disruption for the sake of disruption. If you have something that’s working and the consumer likes it, then you need to nurture it. The goal of any management team should be to create enduring value. And if you’re fortunate and savvy enough to have created a real strategic advantage — what investors refer to as a moat — you’d be crazy to just start filling it in, right? After all, the really good strategic moments are forged over time. You don’t want to sacrifice a well-earned moment just because you have the tools to disrupt your own thinking. Of course, there’s always the risk that a team can get too focused on patting themselves on the back and open themselves up to somebody who is willing to be a little bit crazier. Because no matter how good you are or how deep your moat is, you can always get better. But I think it’s a real balance, and the most successful disruptors know when a process should be fortified and when it’s ripe for reinvention.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

I’ll definitely give you the one I’ve found most relevant in my career: Simplicity breeds results. It means recognizing that you can only do a handful of things really well and that you must always have the alignment, focus and conviction to say no when something starts to drift outside of that zone. Just think of when you come home with a product from Apple. There’s no gigantic manual or flashy box or sales brochure. The packaging is basic and functional, the instructions are sparse and intuitive — and all of this stems from an organizational focus on simplicity. In successful companies, this kind of thinking ripples through everything — from how you communicate with customers to how your product looks to your own internal priorities. It’s a code I try to live by whenever I feel myself getting out of control or enticed by some new initiative that sounds really cool on paper. You have to constantly remind yourself that the human mind is cluttered. We’ve all got countless thoughts floating around in our heads at every moment. You have to cut out anything that doesn’t directly contribute to what you do well. Even on an organizational level, when I see people stressed out or struggling with their jobs — or department leaders struggling with how to manage their team under stress — it’s almost always because they’re trying to do too many different things. They’ve said yes to things they can’t fulfill. And that is always a problem.

We are sure you aren’t done. How are you going to shake things up next?

As a thing, Fair is definitely the kind of big idea that has the potential to make a truly outsized impact on how people access and interact with their cars. But to achieve that, our next chapter is actually going to focus on the best way to implement and grow the disruption that we represent. Lately, this has meant adding short-term leases to our month-to-month subscription offering so that we’re able to best serve customers, no matter their flexibility needs. While most Fair users are still looking for us to give them what amounts to a pay-as-you-go mobility option, people who know where they’re going to be for two or three years can pay a little less per month by committing to a 2-year or 3-year loan. We are also focusing on balancing our direct-to-consumer business with an indirect channel strategy that involves our dealer partners offering Fair as a financing alternative to customers who may come to the car lot with no idea who we are at all. This way, they can opt to pay for their car via a Fair lease instead of taking out a loan for the full cost of the vehicle. We are also in the process of making our website our principal digital asset. We launched as an app and have made tremendous inroads with that as our sole consumer conduit. But I firmly believe that when it comes to a big decision like a car, the vast majority of people are still most comfortable navigating their options and executing the transaction on a laptop. I know I am. And, lastly, we’re going to be hyper-focused on value for the consumer. That means offering consumers cars that are in the mainstream and are at an ideal point in their depreciation curve so that our users aren’t overpaying. Taken together, these initiatives show that being disruptive sometimes means disrupting your own initial ideas of what your business is so you can best get your ideas to the consumer.

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

Well, there’s so many. Through the lens of business, it’s the book “The Breakthrough Imperative,” which I think provides a fundamental understanding of the kinds of things any successful business executive needs to focus on. And then on a personal front, “When Things Fall Apart” has been hugely influential in my life. It’s basically a Buddhist missive about how to deal with disappointment and a lack of focus when the plan you’ve laid out for yourself doesn’t happen. I first read it at a really intense reflection point in my own psychology, and I’d encourage anyone who’s faced any opposition or serious challenges in life to check it out. It’s a pretty easy read that reinforces the importance of being in the moment, not beating yourself up when things look bleak, and not allowing yourself to be taken out of the present by downside thinking. We can all lose ourselves by worrying about what’s going to happen, but you need to have the discipline of thought to avoid that road and always stay engaged with the person across the table from you. It’s tough to do sometimes, but it’s vitally important.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

For me, I think it would be “Speak the truth with love.” To me, that means being honest with yourself, your work and the people in your life. You’ve got to believe that what you’re saying is grounded in fact and logic, but be thoughtful about what you’re putting into the world. Also, you have to genuinely care for the various audiences you serve. At a startup, you’re going to have a lot of them: investors, your employees, your management team. Don’t be afraid to evaluate, ponder and reflect on your decisions, and how they will impact the people closest to you and your mission. There are definitely times you’ll have to be sensitive to what any one audience is capable of hearing in a given moment. But lying, making stuff up, manipulating, and telling people what they want to hear will always come back to bite you. Always. It’s so much better to operate from a place of truth and respect.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I’m definitely passionate that everybody should get off social media and probably stop consuming so much news. I’m not saying people should be uneducated or not be engaged in the world and what’s happening, but I think we should acknowledge that social media — and even our some of our media sources — are businesses that are often best served by manipulating us. There are obviously plenty of bad things happening in the world that deserve our attention, but if you let the negative discourse rule your day, you’re not going to be a happy person. Other than LinkedIn, I’ve never been on any social media platform. In fact, I almost view it as a professional responsibility. If I’m manipulated into being upset or frustrated by a barrage of negative conversations every day, I’m probably going to be a bad leader.

How can our readers follow you online?

Honestly, the best way to follow me is through Fair. Check out our website, watch for us in the media. You’ll definitely be hearing a lot from us — and inevitably from me. I’ll also publish articles on LinkedIn from time to time. I’ve written about how to prep a company for an exit, the XOJet turnaround story, what it takes to save a Silicon Valley unicorn. I think I even published my book list if you’re into that. Or, you know, just email me. You might be surprised how many CEOs will answer a well-posed email, and I’m certainly one of them.

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