Andy Chalofsky of SimpleTire: “Fail fast but always fail forward”

“Fail fast but always fail forward.”: I firmly believe that failure is the catalyst of growth and success. Since the beginning of the business, we’ve used failure as a purposeful part of growth at SimpleTire, rather than avoiding failure at all costs. I’m proud to empower our employees to try new things and fail in […]

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“Fail fast but always fail forward.”: I firmly believe that failure is the catalyst of growth and success. Since the beginning of the business, we’ve used failure as a purposeful part of growth at SimpleTire, rather than avoiding failure at all costs. I’m proud to empower our employees to try new things and fail in order to grow in our business. I will never fault someone for giving something a shot and coming up short as long as they learn from that experience.

As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Andy Chalofsky.

As the CEO of SimpleTire, Andy Chalofsky drives the vision for the company as it continues to evolve. Andy’s entrepreneurial spirit drove him to work hard at an early age, from starting and growing his own lawn mowing business to becoming part of a restaurant team that begged him to skip his summer camp to stay on the roster. This passion is what set him on the path to conceive and grow SimpleTire into the multi-hundred million dollar business it is today.

Andy’s first experience working with tires came as a 12-year-old warehouseman at his uncle’s tire company. He worked his way up in that business and learned that great success is the result of hard work and determination. After earning his college degree, Andy returned to his entrepreneurial passion by taking over Network Tire and expanding its operations significantly. His success at Network Tire enabled him to do a merger with competitor Traction Tire, where he took the role of CEO. Andy eventually sold these businesses to focus on the creation of SimpleTire in 2012.

Andy recognized that the tire industry was fragmented and saw an opportunity for digital innovation, which led him to partner with Josh Chalofsky and Kenny Pratt to create SimpleTire, an e-commerce business founded with the intention of revolutionizing and improving the task of tire replacement. For nearly a decade, the co-founders have prioritized their customers’ needs as they’ve refined their no inventory business model to positively disrupt the tire industry. Their dynamic partnership, speed and business acumen has helped the business grow year over year and led to a significant investment from Dealer Tire in 2018.

In addition to his leadership role at SimpleTire, Andy has a strong passion for real estate and local community business growth. He sits on the Board of Philadelphia-based Delphi Property Group; is a founding member of JAK, a venture funds investment corporation; and is the sole proprietor of Chase Strategic Management Partners (advises and invests in companies around Philadelphia). He is also a member of the Union League of Philadelphia and actively contributes to scholarship funding, the Wounded Warrior Project, and foster care initiatives. Andy also donates his time and counsel to DECA, Inc., an international non-profit student organization for emerging business leaders and entrepreneurs. He is the sponsor of a DECA scholarship for high school seniors preparing to enter college.

Andy is a graduate of Towson University in Towson, Maryland with a Bachelor of Business Administration and Management. When he’s not working, he’s likely traveling the world, enjoying outdoor activities and relaxing at his home in Bucks County, PA with his wife, Amanda and their Cocker Spaniel, Parker.

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?

Even as a kid I had the makings of a serial entrepreneur. I found joy in my entrepreneurship from a young age, from starting my own businesses babysitting and lawn mowing to working in restaurants and as a warehouse worker at my uncle’s tire company. The latter exposed me to the tire industry and eventually set me on the path to carving a niche for myself in the world of tires. After earning my college degree, I was at a career crossroads. I could choose a new career journey — Wall Street was calling — or I could use what I learned in my formative years to continue a career in the tire industry. It was my passion for building businesses that caused me to dive headfirst into a role at a traditional tire supply business. I honed my skills and took on leadership roles at various other tire companies all the while beginning to recognize a unique fragmentation in the tire industry that was ripe for innovation. I saw an opportunity to improve the customer experience by using technology to build a network that provided unrivaled access to tire inventory both for breadth in selection and depth in volume. That realization caused me to found SimpleTire with my partners, Josh Chalofsky and Kenny Pratt, which we’ve successfully built together and continue to grow alongside our exceptional team.

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

We know that more and more consumers are shopping online because of its ease and convenience, but the tire industry is a very traditional one that hasn’t harnessed technology and innovation to impact the customer experience. From the expectation of an unnecessarily high price tag to the need for reassurance that the tire they’ve selected is right for their car and driving needs, there may be negative stereotypes that consumers have about tire replacement. We aim to put the customer at the heart of our business by empowering them with transparency and objective information in addition to providing the best in class products. By giving valuable insights and information to our customers, driven by user data and technology, we’re hoping to instill the confidence in them to make the right decisions about their tire selection & car maintenance. Spending money on car upkeep is never going to be something that consumers look forward to, but we’re hoping to use technology to create a better customer experience that ultimately makes the tire replacement process a more positive one.

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?

When we started out we made the mistake of sourcing our tires from one central warehouse. Our first customer was based in California and he wanted to purchase a tire from us for 70 dollars. We thought we were turning a nice profit on the product…until we realized the shipping rate was going to be 80 dollars. We took the loss and fulfilled the order, but that single transaction is what highlighted the need for a more diverse network of suppliers to make our business model viable. That one failure was the catalyst to conceptualize the foundation on which SimpleTire was built.

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?

My earliest mentor was my uncle. I saw how his success directly correlated to his incredible work ethic during my time working with him at his tire business. He was the first one in the door at 5:30 am and sometimes left well after 6 pm. His grit and hard work made him a successful business owner and respected leader, both of which I aspired to become. His saying was “you don’t have to be smarter than everyone else, you just have to work harder” and I maintain that relentless work ethic to this day.

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?

I believe that disruption is beneficial when it is powered by innovation and the spirit of making things better holistically. That said, disruptive innovation should still maintain respect for the tenets of an industry. In the tire industry, for example, you could disrupt the industry by producing a cheaper tire, which would mean using lesser materials and sacrificing workmanship. However, one structural tenet of the tire industry is safety. We’re the one connection point where your car meets the road so it’s imperative that manufacturers maintain that standard of safety rather than disrespecting quality for the sake of disruption. That type of disruption isn’t driven by innovation and doesn’t holistically benefit the consumer or the industry in the long run. What we are doing at SimpleTire is disruptive because we’re using our unique platform to connect and create a seamless experience for not only our customers but also other players in the industry, like manufacturers, suppliers and installers. I and the other co-founders have blended our expertise across verticals to innovate the tire industry by creating a platform that instills confidence and saves people’s precious time. Combining my vision and understanding of the industry, Josh’s operational and relationship building skills and Kenny’s incredible technical knowledge has allowed us to create a business model that we hope will disrupt the tire industry forever.

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

  1. “You miss 100% of the shots you don’t take.”- Wayne Gretzky: This is a quote that has guided the success of SimpleTire. Since day one we’ve been willing to take a lot of shots on things even if they didn’t seem possible to make. Some of our best client relationships and innovations have come from taking a risk on asking for something or creating new capabilities that others around us may not have been willing to.
  2. “It’s not about what. It’s about who.”: In more recent years I’ve learned that the key to building an incredible company is hiring the right people for the right positions and then allowing them the space to succeed in their areas of expertise. It no longer becomes about what our employees “should” be doing in their roles at SimpleTire, but rather how do we attract and engage with the best talent in the field who will have the tools to excel at SimpleTire. Once I started focusing on who we were hiring to build our team I saw our business growing more rapidly.
  3. “Fail fast but always fail forward.”: I firmly believe that failure is the catalyst of growth and success. Since the beginning of the business, we’ve used failure as a purposeful part of growth at SimpleTire, rather than avoiding failure at all costs. I’m proud to empower our employees to try new things and fail in order to grow in our business. I will never fault someone for giving something a shot and coming up short as long as they learn from that experience.

Lead generation is one of the most important aspects of any business. Can you share some of the strategies you use to generate good, qualified leads?

We have a unique opportunity to utilize our platform to connect all parts of our industry including installers, manufacturers, suppliers and consumers. We can allow each stakeholder group to have a voice on our site and engage with one another, which I believe creates a flywheel of lead generation. Customers can use SimpleTire to talk about their experience and needs, which results in brands in the space (manufacturers, installers and suppliers) wanting to be there to feed them relevant information. That, in turn, causes more customers to engage further. For us, it’s about figuring out how we can be a good input to all parties so we can serve as a good output to all parties.

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

We are launching an entirely new website interface with the aim of revolutionizing the way that consumers approach tire replacement. The new user experience takes the customer on a journey full of data-driven insights and helpful information to ultimately simplify the process of selecting, buying and installing new tires. We really put the customer first in developing this new experience with the intention of becoming their car maintenance allies for life. The intention is to supply the right objective information throughout the tire buying process to help our customers feel more confident in the decisions they’re making and then help them cross the finish line by connecting them with the right local installer to fit their car with the new wheels. I can’t give too much away about the next step of our industry shakeup, but I can tell you that we’re hoping we can continue to be our customers’ allies beyond just tire replacement. Watch this space…

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?

The book “Who: the A method for hiring” by Dr. Geoff Smart and Randy Street has deeply impacted me as a business leader. We’ve undergone rapid growth in the past few years. As a result, our team has also more than doubled, which means we’ve been focused on attracting, engaging and cultivating talent across all facets of our business. It’s caused me to shift my mindset to focus on the “who” of the business and not the “what” and build a team of experts who can effectively lead and grow their focus areas.

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

Crawl, walk, run” is a life lesson quote that sticks with me throughout all of my endeavors. I believe that it’s not the big that eat the small but rather the fast that outrun the slow. Unfortunately, many people get so bogged down by planning how they’re going to run fast with their big idea that they’re doomed before it even gets off the ground. I’ve learned that you need to start small and focus on the little wins in the beginning that give you the momentum you need to carry your idea forward. Once you do that (and work hard, of course) everything else will follow.

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. 🙂

We’re working hard to elevate transparency and accountability within the tire & automotive industry, but I feel our country and the world as a whole would be better if there was more of a focus on those attributes across all industries. We’re a society that talks in sound bites leads with pictures and believes the hype. A bigger movement that rewards factuality and instills accountability would cause positive change in our communities, country and the world.

How can our readers follow you online?

You can find us online at and on the social media channels across the board below.

This was very inspiring. Thank you so much for joining us!

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