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Inside the Mind of Serial Entrepreneur Jesse Williams

Technology has grown exponentially in the past twenty years, and the Internet has become an inextricable part of daily life. Because of this, the possibility to build a new way of life and create careers counter to the traditional 9-to-5 grind has also grown. But there were people who saw the great opportunities the digital landscape had to offer back when we were still calling the Internet “The World Wide Web”. Jesse Williams, a digital marketing expert and serial entrepreneur, was one of those self-made business visionaries who took hold of the Information Superhighway’s potential when it was still in its early years.

Growing up in Alberta, Canada, Jesse was always fascinated by the business greats who came before him, such as Bill Gates and Warren Buffet. At 15 years old, Jesse launched his very first business on the web: eDirect, a fully digital company that sold computer software. In just one year, Jesse’s business earned more than $40 million in sales. It was his first taste of success that ultimately lit the fire to grow and create more businesses, and this led to a long journey that would test the limits of his business acumen and push him to go even further beyond.

Jesse agreed to sit with us and share some of his insight about what brought him so much success and how his journey has been so far.

Thanks for being here with us today. You started off your business journey at such a young age. Were you ever put off by the overwhelming wealth of possibilities the Internet offered?

JESSE WILLIAMS: Thank you for having me. For me, changing directions is always challenging, but I was also more excited than anything to make my mark. As an entrepreneur, you always have a thousand different ideas and ways to make money. 

That’s one of the realities of digital marketing, what works today may not work tomorrow, and we have to be constantly willing to evolve how we conduct business. The key is figuring out where your passion lies and where you see the biggest opportunity to come out with something that doesn’t exist in the marketplace.

Being an entrepreneur for so long, what have been some of your favorite projects? 

JW: I’ve been in the automotive market now for over a decade with a focus on used cars. When we launched in 2016 to provide free vehicle history reports to consumers, that was my most exciting project. We were the first site to provide car buyers accident and maintenance details to car shoppers for free.  

Is there an industry that you feel most comfortable in? Is there one you would like to improve more? 

JW: For now, my passion is in the automotive industry, but someday, I would love to enter the property market. There is so much information consumers need that currently they don’t have access to.

What is your greatest accomplishment to date? 

JW: My greatest accomplishment was when Vehicle History surpassed 4 million users a month last year. There were years when we didn’t know if the project would be a success. To see so many people get value from what we created has been quite special.

What were some of your biggest challenges? What lessons have you learned?

JW: In 2010, the multi-million dollar nutritional supplement company I was running went out of business. That was the toughest point in my career. I had to start over with a completely new venture. From this experience, I learned to always be looking for new ideas and new business approaches as you never know when your current business may become no longer viable.

What’s something you would like to work on but haven’t had a chance to yet? 

JW: I would love to get involved in the fitness industry. As someone who loves to exercise and eat healthy, this has always been my passion. Unfortunately, we struggle with obesity in this country, and I know that, with proper education, we could do so much better.

Being an entrepreneur comes with its own risks and rewards, what is a piece of cautionary, practical advice you wish someone had given you when you started? 

JW: It’s important to have confidence in our vision and be willing to take chances. However, always stay open minded to contrary opinions and listen to feedback. It’s critical for entrepreneurs to always keep learning and improving their business.

How did the pandemic impact your business(es), if at all?  

JW: We at VehicleHistory have been lucky to be in an online based business, so the pandemic has a minimal impact. I will say I’m grateful most of our employees have returned to the office. From a personal standpoint, I found it difficult each day during the pandemic with human interaction.

Did it change your approach as a businessman? 

JW: The pandemic taught me that business owners have to be more flexible with our teams. We no longer have specific hours or locations our employees must work. By adding flexibility, we have found everyone is happier and it has greatly reduced turnover.

What are you most looking forward to in post-pandemic times? 

JW: My favorite hobby is traveling the world to climb mountains. I’m so excited to be able to travel once again. My next trip is to Argentina to climb the highest mountain in South America called Aconcagua.

What is your most recent project that you’re working on now? 

JW: Late last year, we launched our used car reviews. We now cover most vehicles from 2005-2018, providing reliability, problems, owner reviews and other critical information to the used car buyer. Most automotive companies are reviewing cars when they are new, we are one of the first companies to give accurate information about how the cars hold up overtime.

Is there anyone you’d like to collaborate with on a project?

JW: I would love to work with JD Power, they are doing some great work analyzing long term reliability of vehicles. For used car buyers this information is so critical especially when purchasing an older vehicle. We have seen a significant variance in how long one model of car will last vs another.

How do you feel about the future?

JW: I remain very excited about the future, I see so many great new ideas from the next generation of entrepreneurs. I believe we will always face challenges as a society, including some big ones but the future remains very bright.

Thank you to Jesse for the interview. To learn more about Jesse Williams, connect with him on Twitter at