The Comeback Kid: How Jesse Willms Survived a Lawsuit from Microsoft and How He’ll Survive 2021


Jesse Willms: Teenage Millionaire

Jesse Willms was a 15-year-old business prodigy when he nearly lost everything. It was the early 2000’s, the glistening height of the Dot-Com era, and the young entrepreneur was reading every book about business management he could get his hands on. It was then that Willms put into practice one of the most essential principles for starting a business: identify a hole in the market and fill it. In this case, that business was software sales, and the window the young businessman found to exploit it was pricing. He spoke about the venture in an interview with Authority Magazine last February: “Often, software was priced cheaper in different regions around the world, so we could get better volume discounted pricing and then pass those savings to consumers in the United States.” The distribution company Willms created, eDirect, quickly became a multi-million-dollar enterprise, only to come under fire from the biggest software developer they sold, Microsoft.

                “We were buying software using Microsoft’s business volume discount programs to provide individuals with discounts,” Jesse Wilms admits in his interview with Jerome Knyszewski, “This was cutting into the software company’s profit margins, and we quickly became a target.” At 18, Jesse Willms had created a multi-million-dollar company and was now being sued by Microsoft. As a small business owner facing down the prospects of a powerful legal team, he had no choice but to settle the lawsuit for over a million dollars. This kind of defeat would end the career of many entrepreneurs, but Jesse Willms was just getting started. Since then, the entrepreneur has started multiple multi-million-dollar enterprises in dietary supplements, oolong tea, and even teeth whitening. Wherever the opportunity presents itself, Willms is quick to follow.

                Now, in the wake of an unprecedented global pandemic that’s left many entrepreneurs scrambling for cover, Jesse Willms is setting his sights on the future. Far from manufacturing, he’s found new opportunities and another hole in the market: information. Armed with an increasingly popular car research website on the brink of profit-making, a new mentoring-focused mindset, and even his own scholarship, Jesse Willms has his sights set on the future of entrepreneurship.  Through all of his successes, setbacks, and ventures, the Las Vegas based entrepreneur has a lot to teach those just starting out, and is learning new methods to succeed and new avenues for success all the time.

Jesse Willms made Car Shopping Easier

                A great way to identify a hole in the market is to drive right into it. Jesse Willms was inspired to create the Car History Group and by extension by his frustration with the difficulty of researching used cars. Predatory online businesses have exploited the obfuscation of vehicle incident report for years, and the Las Vegas entrepreneur had had enough. His website is the first of its kind to offer completely free vehicle reports. Now, through add revenue, the website has been able to flourish with millions of page views per month. It’s a pragmatic business strategy that potentially undercuts serious profit, existing primarily to be a useful resource in its own right rather than a purely profit-making venture.

                In an interview with Inspirey from January, Willms expresses some of his deeply-felt hopes for the Car History Group in the future: “We hope to be the leading automotive research sites over the next few years. I am most excited about the advancements that we’re seeing in our industry. Every year, cars have more safety features, and with self-driving cars on the horizon, our roads are only going to get safer, thus saving lives. Another big concern of mine is global warming, but the skyrocketing popularity of electric cars will go a long way to help solve this global problem.”

                As an early adopter of the internet and a businessman at an early age, Jesse Willms believes a customer-base armed with knowledge is the next step towards a brighter and more environmentally friendly future. With electric cars in mind, his website is not only an investment in information, but an investment in our planet’s future. To Willms, the value of the service offered to customers and the value it provides the business owner are codependent. As he says in his interview with Inspirey: “The best marketing strategy has been finding an underserved niche in the marketplace and make truly great products.”

                This isn’t to say the patch to financial viability for the Car History group was easy. On the contrary, for a time the website’s success was touch-and-go, with Willms and his partners expressing concerns for success against their competitors:  “For the first three years, we really weren’t sure if this business model would work. Everyone in our industry, including Carfax and AutoCheck, charge for this
data. We had a lot of ups and downs with Google and how much traffic we received; just when we started gaining momentum, we would see traffic drop again. We all stayed focused and kept making progress little by little, and our motto was ‘one step at a time.’ Now that we have started to receive major advertising revenue from car manufacturers, we have become confident in the
long-term vision of the company.”

Ultimately, the best content wins, and if you can provide something that doesn’t exist today, you’ll be very successful.” Willms competitors in the VIN report business had managed to succeed at the first part of that strategy: identifying an underserved niche. But by exploiting that niche, those businesses create an antagonistic relationship with their clientele. With the freedom to charge unreasonable prices to access accident reports, a certain amount of profit early on is almost inevitable. But success built on such a relationship cannot last. Now, Willms has succeeded in making the most popular used-car research website of all time by offering a service he believed should be implicitly free of charge.

Far from undercutting the profits of a major software company, the only companies this strategy manages to undercut, are deeply problematic and predatory. Willms has been an entrepreneur for eighteen years now, and even in the eDirect era his goal has always been to alleviate problems for customers rather than exacerbate them. Jesse Willms is entirely self-taught, his entrepreneurial experience built on a foundation of books he studied as a teenager and over a decade of trial and error. His desire to arm potential consumers with knowledge informs as much of his work as his aforementioned desire to make their lives easier with lower-priced software. If the world at large is ultimately better for customers having the information they need on a given car, why hide it behind a paywall? This same pragmatism not only informs Willms used car information business, but the entirety of the new phase of his career. With so much experience of both unprecedented success and near catastrophic failure, Jesse Willms has now set his sights on mentoring new entrepreneurs in the hope that they will not only succeed as much if not more than he has, but avoid some of the many pitfalls he ran into along the way.

Jesse Wilms Invests in the Next Generation

                Jesse Willms has put a lot of stock in the future of entrepreneurship. His confidence for the next generation is well-earned; after all, he was only fifteen when his own career began. He’s the least likely entrepreneur to underestimate his youngers, and on the contrary has given them particular focus in this stage of his career. In this new era for Willms, so much of his work is centered on mentorship. Not only is the founder of multiple highly successful business ventures offering advice to those that follow in his footsteps, but he is giving it away for free on his website or through various interviews elsewhere.

                At the moment, the world is still an incredibly uncertain place to start a small business. Our most prosperous nations are on the rise but still recovering from the COVID-19 pandemic that began in earnest in the United States last march. Many are unsure what the future holds with offices still largely remote and the hospitality industry still in shambles. Jesse Willms, fresh from the perils of this disastrous year-and-a-half is quick to advice prudence in any first time business owners: “Manage costs closely in the good times, so you have a nest egg to protect you in the tough times. Often, we only cut costs when it’s too late, but managing your budget should always be a priority.” Jesse Willms has come back from worse losses than most entrepreneurs will ever experience. But, if he can, he’ll spare prospective business owners the same fate.

                On top of the free mentorship he already provides through his website and interviews, Jesse Willms is also investing in new entrepreneurs through his own scholarship. As it says on his website: “The Jesse Willms Scholarship Program seeks to help out student in need via financial aid. The scholarship is for student in business programs or interested in running/starting their own business.” Three prizes will be given out by the scholarship in 2021 of $3,000 , $2,000 , and $1,000 respectively. To earn one of the prizes, applicants will need to answer the following question in a written essay: What is your idea for a business and how would you bring it to life?

                While much of Willms advice to new entrepreneurs is about researching viable markets, deferring to experts, and keeping unearned confidence in check, a common theme in his mentorship is encouraging the young and the uninitiated to take the plunge. Even though his very first business at fifteen lead to one of the largest defeats of his career, it remains one of his proudest moments, and by his estimation started him on the path towards entrepreneurial success:

“The most satisfying moment in my career was early on, when I saw my software business become profitable. To pursue my passion, I left high school at an early age, and many of my friends saw this as foolish. At the time, I knew that there was a high chance that it would fail, but I would forever regret not trying. I also knew that if the business became a success, I would be free to pursue a career I loved.”

The Comeback Kid

                Jesse Willms became an entrepreneur at age fifteen and could’ve retired at age eighteen. He dropped out of high school only to achieve a career unattainable by most PHD graduates. He’s faced business rivals, lawsuits, and tribulations that would lead anyone in his position to a different career path. But the Canadian entrepreneur has taken each loss as a learning experience and rather than surrender his career, he’s adapted to change. “I’ve always believed that success comes from working hard to pursue your vision while constantly learning and adapting your strategy. Our businesses are going to change over time, so it’s important to be flexible and keep evolving.”

                Jesse Willms is the first to admit that 2020 was as hard on him as every other business owner: “COVID has been very tough. When we have to do layoffs, those are always the toughest decisions. When we have to let hardworking people go, that is very tough.” Were he not the same man who’d cut his teeth learning how to run a business at fifteen during the software boom, it might have been too much for Willms to handle. But with his experience, adaptability, and drive, the future is looking very bright. “I’m looking forward to 2021,” he said to Inspirey, putting his misgivings on 2020 behind him, “and I’m confident that we will rebound from a difficult year.” Not everyone will find ways to flourish in the next year. Some will retire, some will enter new fields or take a lower-position at another company. Most aren’t built for the kind of risk it takes to run a business, or lack the finances to survive an entrepreneurial failure. But not Jesse Willms. The entrepreneur has made significant comebacks over the course of his career, and with any luck he’ll keep making them.

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