Driving Disruption: Jonathan Shaw Of Hemmings On The Innovative Approaches They Are Taking To Disrupt Their Industries

An Interview With Cynthia Corsetti

Multiple Marketplaces: Hemmings is not taking a “one size fits all” approach to its marketplace offering. We have run a traditional classified marketplace since 1954, launched an online auction platform in 2019 and built a Make Offer/Buy Now marketplace in 2023. Through our 70 years of marketplace experience, we’ve learned that buyers and sellers want options. Some want to do their own deals over the phone, some want to capture peak elasticity through the competitive nature of 7-day auctions, and some want to expose their vehicles to a global audience but set their own asking price and terms. Nearly all of our competitors offer one buying and selling format, but not all three.

In an age where industries evolve at lightning speed, there exists a special breed of C-suite executives who are not just navigating the changes, but driving them. These are the pioneers who think outside the box, championing novel strategies that shatter the status quo and set new industry standards. Their approach fosters innovation, spurs growth, and leads to disruptive change that redefines their sectors. In this interview series, we are talking to disruptive C-suite executives to share their experiences, insights, and the secrets behind the innovative approaches they are taking to disrupt their industries. As part of this series, we had the pleasure of interviewing Jonathan Shaw.

Since 2020, Jonathan Shaw has been the president of Hemmings, the world’s largest collector car marketplace, founded 70 years ago this year. Jonathan has been leading the innovation and transformation of Hemmings into a dynamic digital marketplace, all while preserving its cherished print legacy. As the original collector car marketplace, Hemmings has grown and evolved their business to provide products and services that meet the needs of enthusiasts who enjoy buying and selling collector vehicles. Under Jonathan’s leadership, Hemmings is now positioned to disrupt how individuals and dealers buy and sell classic cars through a ‘frictionless’ marketplace.

Thank you so much for joining us in this interview series. Before we dive into our discussion about disruption, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

My path to becoming President of Hemmings was driven by a personal history with Hemmings and a diverse career in digital product development, marketing, and e-commerce. In 2019, as Head of Product & Development at American City Business Journals, a division of Advance, I was tasked with leading the development of a new auction platform for Hemmings, a print-media giant in the collector car market. Realizing Hemmings’ potential in the digital realm, I embraced the challenge, seeing it as an opportunity to leverage the brand’s longstanding trust in the collector car world. With leadership’s support, I expanded my role, immersing myself in the company to blend my professional skills with my love for cars and personal history with Hemmings.

My earliest exposure to Hemmings was when my grandfather, Ray, used to bring his copies of the Hemmings Motor News magazine to our house when I was a kid. We’d flip through the classified ads and point out our dream rides. My fingers would be black with ink by the time we finished going through its hundreds of pages.

After successfully launching the online auction platform in 2019, I joined Hemmings full-time as president in 2020. This marked a pivotal moment for both my career and the company’s digital evolution. My team and I have worked diligently, transforming a 70-year-old establishment into a bustling digital marketplace and media company. I’m proud of our team’s transformative efforts.

What do you think makes your company stand out? Can you share a story?

In the midst of tremendous internal transformation and broader industry disruption, we’ve remained focused on successful outcomes for our customers and partners by evolving our product offering and go-to-market strategy. For new businesses, this might seem routine, but a 70-year-old enterprise company to adapt and change in real-time is something completely different.

When I first arrived at Hemmings in 2019, the company was a print media business that ran a classified marketplace. We had virtually no marketing department — leading us to an inactive social media presence, limited internal digital development resources, and an audience that wasn’t growing. Recognizing that the marketplace was the digital future of the business, we launched online auctions, a Make Offer marketplace, and a marketplace mobile app. Recently, we launched our new, digitally enabled Frictionless Marketplace — a suite of services including valuations, inspections, our new Pay + Title offering, insurance, and shipping to make the buying and selling process for our customers … well — frictionless. In our media business, we’ve relaunched our YouTube channel and are focusing on creating resource-based original digital editorial content. We have also unveiled a complete rebranding and design of Hemmings to serve us in the digital age.

We’ve adapted to serve distinct print and digital audiences, enhancing our brand, customer base and product offering in the digital era without compromising our focus on customer success.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Perseverance: In 2015, I was a senior digital product manager and brought to market several successful products for my employer. They were in search of a new CTO, and based on the information I was given, I would be their Head of Product. Instead of receiving the promotion, I ended up being layered by an outside hire the CTO brought with them before they even started. It was a hard pill to swallow… Instead of leaving the company, I decided to view it as a wake-up call. I felt inadequate and inexperienced and hated that. So that same year, I enrolled at the University of Wake Forest’s School of Business to get my MBA. From 2015 to 2017, I worked full-time while also attending night and weekend classes. I was determined to persevere through that experience and come out as an even better, more rounded professional on the other side. I received my master’s in business in 2017, continued performing at a high level in my role and was named Head of Product shortly after graduating. It’s important to remember that professional development and career paths aren’t linear, there will always be setbacks. Those who push forward and persevere through adversity will be rewarded in time. I now see that difficult time as one of the best things that ever happened to me professionally.

Compassion: People often talk about the need for separation and boundaries between life and business. That’s not reality — there are personal, family, and life needs that have to be dealt with during work hours and in our industry, work often bleeds outside of 9 am to 5 pm. Businesses have to be flexible and adapt to fit the lives of their employees, especially if they plan on retaining great talent. Being compassionate and understanding that your co-workers are human beings seems rudimentary, but many executives get this wrong.

In 2011, I was running Rowdy.com, a motorsport-focused social network. We had been using a contracted video producer whose wife had just given birth. As a self-employed individual pre-Obamacare, he had no health insurance, and their baby was in the Neonatal Intensive Care Unit. He came to me and began weeping uncontrollably, largely out of fear for his child’s health but also because he had no health insurance and no way to pay for the continuing care of the baby. After we talked, I went straight to our parent company’s CEO and explained the situation. I requested that we immediately hire the contractor as a full-time employee to provide him with full healthcare benefits. I was quite passionate about why we had to do this, and the CEO approved the hire. It wasn’t a hire the business had to make; in fact, we weren’t in a fiscal position to be doing so. But we did it because it was the right thing to do. Compassion is a hallmark of not only great leadership but also being a good human being. That individual is still with the parent company today, and every time I see his car in the parking lot, I think about that moment.

Strategic Vision/Change Agent: If you are a leader without a clearly defined strategic vision that you can effectively communicate, you aren’t a leader, you are an operator. You might run the machine, but you certainly aren’t driving it. The best leaders in the world have a strategic vision driving them to consistently evolve their product or model to stay current with customer’s needs. They constantly study consumer behavior, stay ahead of changing regulations, introduce new product advancements and learn from innovations in non-endemic industries. Not evolving your business, just operating, breeds stagnation, and you open the door to new entrants and competitors taking your market share.

When I got to Hemmings in 2019, the company had fallen into stagnation; it had allowed competitors to take market share and wasn’t evolving. But all was not lost, we still had a phenomenal brand reputation and massive audience scale, but the purpose of why we existed was muddied. Hemmings was founded in 1954 to connect buyers and sellers of vintage vehicles and parts — it was a marketplace. Along the way, it shifted into a media-focused company that operated a marketplace. After studying the industry landscape, listening to our customers and looking through all of our analytics data, I realized that the main attraction was still the marketplace. The marketplace was driving the audience scale, which in turn was driving the media revenue. If we didn’t refocus on the marketplace, our business wouldn’t survive. From 2019 to 2022, we played catchup, developing new digitally enabled marketplace platforms.

In 2023, we entered territory we hadn’t touched since our founding in 1954, we were on the bleeding edge of development in our industry when we launched our marketplace mobile app and a suite of services designed to take the friction out of collector car buying. In that time the media industry has undergone rapid change, and we’ve successfully lessened our reliance on media revenue through our focus on growing and evolving our marketplace business. We are bigger than ever, and that wouldn’t have happened if we didn’t focus on evolving the business based on a sound strategic vision.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader? I’m curious to understand how these challenges have shaped your leadership.

Sometimes you have to put the company’s needs above those of your partners, and that can mean sacrificing revenue. When we launched our online collector car auction in 2019, we had built a significant advertising business from live auction houses. We knew there was potential to lose revenue and some decades-long partnerships if we launched. In fact, when word got out, I received a nasty email from the CEO of one of the largest live auction companies in the world. He had even cc’d the CEOs of every major auto auction to boot, threatening that if we launched, they would all turn their backs on us. So, we had to choose between preserving the existing revenue stream or taking a chance on the auction startup. Ultimately, we couldn’t sit idle while e-commerce was disrupting and changing our business. We successfully launched the online auction in August of 2019 and have continued to expand it since then. As for all of the partners, we still serve their needs too. You have to do what is best for your business; if you don’t, you won’t be there for your partners anyway.

How do you perceive the role of ‘disruption’ within your industry, and how have you personally embraced it? Is it a necessity, a strategy, or something else entirely in your view?

I love disruption, it is both an economic necessity and a leadership strategy. Being an entrepreneur is about embracing disruption from the outside, being an intrapreneur is doing it from the inside. I’ve made a career out of disrupting established business models from within and helping companies react to being disrupted from the outside. Disruption, if embraced, can be the forest fire that enhances the very soil the forest grows in. It’s painful, but if you are quick to recognize it, weather the storm, and embrace change, your business will emerge healthier. In my view, disruption is constant in business. You either purposefully self-inflict disruption to evolve, or you receive it from a competitor. It is always better to disrupt yourself than react to someone else doing it. Stagnation is poison in business, disruption is the antidote.

What lessons have you learned from challenging conventional wisdom, and how have those lessons shaped your leadership style?

Data doesn’t lie. If you are going to challenge widely accepted beliefs or long-entrenched business practices, you need to have plenty of data to support your stance. User research, focus group, digital analytics, case studies etc… Arm yourself with supporting data and find a way to test your hypothesis before jumping in.

Disruptive ideas often meet resistance. Could you describe a time when you faced significant pushback for a disruptive idea? How did you navigate the opposition, and what advice would you give to others in a similar situation?

As the Director of Commerce Products at The Business Journals I believed we could implement a paywall on digital articles to drive subscriptions. Today paywalls are ubiquitous, but in 2015 there was still a widely held belief that the internet was “free” and the only way to monetize your audience was with advertising. So, I was up against consumer preference and internal conventional wisdom. But I was convinced we had information and niche content people would pay for. I gathered a trusted team across editorial, product and audience development and began an internal PR campaign to test a paywall in select markets we operated. We would paywall three digital articles a day in each market. The debate raged — the dissenting belief was that we were going to kill advertising on the site. It went all the way to the top, literally. We had the CEO join the final meeting, where I emphatically made my case for testing and reassured him it was a limited test in a few markets (they were in 40 cities at the time). Ultimately, we triumphed, and there has been a digital paywall on the sites ever since. What we did in that time literally rewrote the course of revenue for the company and ensured its future success in the digital age.

My advice to others in a similar situation is to find a way to test your idea with minimal disruption to the existing business. Gather a team of like-minded individuals who share your beliefs and gather data on every aspect of your test. Data doesn’t lie, but make sure your test sample is large enough or lasts long enough to give definitive proof.

What are your “Five Innovative Approaches We Are Using To Disrupt Our Industry”?

1 . Lifecycle Strategy: In 2020, we developed our lifecycle strategy for collector car enthusiasts. We wanted to support our customers at every step of their journey, from showing interest in joining the community to buying, owning and eventually collecting or selling their collector cars. Through our content and videos, we develop interest and provide research guides to buying collector cars. Through our marketplaces, we facilitate purchasing and provide fulfillment services. Through our own events and those we support; we give owners an opportunity to experience their vehicles and interact with the larger community. In the final stage of the lifecycle, owners either sell their vehicles, where we support them with valuations and our three distinct marketplace selling options, or they add to their collections and the lifecycle begins again from the start. Engage & Research, Buy, Own & Experience, Sell and/or Buy again.

2. Frictionless Marketplace: The launch of our Frictionless Marketplace in January of this year marked Hemmings’ transition from keeping up with the collector car industry’s evolution to being on the bleeding edge of innovation. Through extensive customer research that began in 2021, we set out to build a set of services to remove all barriers to entry and exit of buying or selling a collector vehicle. The premiere product of the Hemmings Frictionless Marketplace is Hemmings Pay + Title, where we provide identity verification of buyer and seller, secure title transfer for the vehicle, a fraud-proof platform to transfer funds and even a 30-day temporary registration and license plate for the buyer. Additional Frictionless products include personalized vehicle valuation, pre-purchase inspections, vehicle shipping service, an insurance marketplace, auto loan financing and even professional photography services for sellers.

3 . Multiplatform Brand Expansion and “Edu-tainment”: We have taken an omnipresent and omnichannel approach to expand the Hemmings brand via three print magazines, original digital article and video content, live events, a mobile app and a rich social media presence across all major platforms. We have refocused all of our content production around being a resource and guide first. We call this new content type edu-tainment. We want the content to be engaging while also teaching the consumer something new. Our goal is to be the ultimate guide to the collector car world, welcoming new entrants and enhancing the experience of long-time collectors.

4 . Multiple Marketplaces: Hemmings is not taking a “one size fits all” approach to its marketplace offering. We have run a traditional classified marketplace since 1954, launched an online auction platform in 2019 and built a Make Offer/Buy Now marketplace in 2023. Through our 70 years of marketplace experience, we’ve learned that buyers and sellers want options. Some want to do their own deals over the phone, some want to capture peak elasticity through the competitive nature of 7-day auctions, and some want to expose their vehicles to a global audience but set their own asking price and terms. Nearly all of our competitors offer one buying and selling format, but not all three.

5 . Real customer service: While many companies have moved towards embracing automated customer service representatives or, in the worst case, purposefully making their company un-contactable, Hemmings understands the importance of building direct relationships with our customers. We pride ourselves on offering premier customer service with live agents and believe this is a strategic differentiator. To that point, we maintain a significant dedicated customer service department of full-time Hemmings employees at our headquarters in Vermont. They answer every single customer service call, text, email or even fax. Our premiere customer service is the cornerstone of ensuring successful customer outcomes and, I believe, is why we have been in business for 70 years.

Looking back at your career, in what ways has being disruptive defined or redefined your path? What surprises have you encountered along the way?

I wasn’t particularly disruptive early in my career, but I’ve always had an entrepreneurial spirit. It wasn’t until I got into technology and digital product management that I learned of the power of disruption. Harnessing its potential impacts completely changed my career. I wouldn’t be President of The World’s Largest Collector Car Marketplace and leading Hemmings in celebrating its 70th anniversary without being disruptive.

I have been surprised at some people’s unwillingness to change in business, even in the face of being disrupted from the outside. If you are the incumbent, someone is going to try and take the crown. You have to act like a challenger brand, even if you are an established player. Another surprise is how many unfounded opinions fly around. I call them heart-thoughts, they might be what you believe in, but I want to see data or testing to back it up. Now don’t get me wrong, sometimes you have to go with your gut. I like those moments a lot more now in my career because I can trust my gut based on experience. You must earn that right, I suppose.

Beyond professional accomplishments, how has embracing disruption affected you on a personal level?

When I went back to business school in 2015, it was already a busy (chaotic might be the better term) time in our lives for my wife, Ashley, and me. We had a one-year-old son. Ashley had just left her full-time job and launched her own interior design business, and we had just sold our house and were living in an apartment while we fully renovated our next house. Ashley was pregnant with our second son, who was born in July of 2016. I was between my first and second year of business school, and I was still working full-time. Even through all that self-selected stress, we were happy because we had a shared vision for what we wanted to achieve both personally and professionally, and we had a plan for how to achieve it.

I would say embracing disruption personally is only beneficial if you have a long-term plan and goals, and disruption helps you achieve them. Otherwise, personal disruption might turn into self-destruction if it’s not directed appropriately. One positive lasting by-product of that crazy period from 2015–2017 was my learning how to effectively manage my time. When to work, when to study, when to be present with family, and, importantly, knowing when to take time for myself (though I still struggle with that last part).

In your role as a C-suite leader, driving innovation and embracing disruption, what thoughts or concerns keep you awake at night? How do these reflections guide your decisions and leadership?

Do all our employees understand our strategic vision and how they play a part in execution? Are we getting products to market fast enough to avoid disruption from a competitor? Are we scaling audience and revenue on those products? If I were a competitor, how would I attack my business?

Owning a multi-million-dollar P&L, having 100 employees and leading a pinnacle brand is a lot of responsibility. At the end of the day, if we are making our customers successful in their pursuits, and their needs are met, we will meet our responsibilities from a business perspective.

You are a person of great influence. If you could start 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 have an idea for how to disrupt charitable giving. It creates a competitive element when rounding up on credit card spending. I have a full business plan and even a name: MissionCents. I am going to build it when the time is right. But imagine the citizens of New York City taking on the residents of Los Angeles for a month-long giving competition… The winner has to take on Dallas Forth-Worth next. If you think you can help me build this, get in touch!

How can our readers further follow your work online?

Follow what we are building at Hemmings.com, download the marketplace app and connect with me on LinkedIn.

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.