How Serial Entrepreneurs are in a League of Their Own

Martin Gray
3 min readOct 1, 2020

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Photo by Startup Stock Photos from Pexels

Many do not understand what a serial entrepreneur is or fully appreciate what they offer. However, in short, a serial entrepreneur is someone who has started and ran multiple businesses throughout their career, even after they have achieved success. To understand what make them unique and why they are in a league of their own, we are going to take a closer look at what makes tick.

They Are Focused on Growth

When it comes to growth, serial entrepreneurs are rarely, if ever, satisfied with the status quo. They understand the market and more importantly, have an intuitive ability to gauge what needs to be done to achieve growth. Oftentimes, their intuitive nature helps them to envision what the future needs of the market is going to be.

One such serial entrepreneur is Matthew Telesca. In the late 1990’s, Telesca understood that there was a growing need in the marketplace for automated and simplified transportation. An easier way to compare providers, their costs, different lanes and more. He had firsthand experienced the difficulties of handling these issues while working in a warehouse.

This ultimately led to the creation of logisticsquote.com, one of the first online transportation marketplace websites. As the founder, Telesca was focused on not only bringing growth, for his new start-up but also wanted to change how the shipping and logistics industry operated.

They Understand the Risks

Serial entrepreneurs understand the risks involved in creating a business from scratch better than others. Additionally, they are not afraid to look for specialized help from others who strengthen their business and vision. Their people centric approach to leadership allows them to develop bonds with others which are ultimately beneficial for both parties.

This is another key aspect that you can see in serial entrepreneurs, such as Telesca. When Telesca had the idea for LogisticsQuote, he sought the help of two childhood friends that were astute programmers and could help him achieve his vision for a fully automated transportation website.

After months of development and over 300,000 lines of code, Telesca had created one of the industry’s first fully automated transportation websites. In May of 2000, logisticsquote.com launched. To the excitement of the industry, LogisticsQuote, had immediate success.

The risk involved was monumental, but Telesca understood that the website was revolutionary, and it was needed. It ultimately paved the way for digitalizing and automating many of the processes in shipping and transportation. It allowed the customers to quickly set up accounts and search for carriers, compare shipment rates, automatically create the required shipping documentation, and track the status of their shipments online.

They Always Want to Improve

One of the most notable qualities of a serial entrepreneur is that they are constantly looking to improve upon their original ideas. While LogisticsQuote was a great idea, Telesca saw how he could further improve the shipping process.

In 2004, Telesca sold logisticsquote.com to a private equity group, and Telesca started MGN Logistics, a freight management company. In 2007 MGN acquired a Boston-based transportation management company, which would be the first of many future strategic acquisitions. Each acquisition presented new and exciting opportunities to modernize the existing platform.

MGN Logistics continues to innovate and has grown to over $40 million in annual revenue. While Telesca remains an integral part of the MGN team, he is excited to have opened a new technology start-up in San Juan, Puerto Rico last year in 2019. AI Logistics will explore opportunities and focus on integrating blockchain technology, machine learning and artificial intelligence, to efficiently optimize some of the transportation industry’s continuing antiquated processes. This next-generation start-up has already started seeing substantial growth.

Yes, as is evident, serial entrepreneurs truly are in a league of their own.

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Martin Gray
Martin Gray

Written by Martin Gray

Martin Gray has BSc Degree in MediaLab Arts from the University of Plymouth. He currently lives in New York city. All links here: linktr.ee/martingray

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