The journey began at Mercury Marine, a Fortune 500 company based in Fond du Lac, Wis. Two coworkers with big dreams and a brotherly bond built Legacy Express: a trucking family celebrating their 10th anniversary this May.

This anniversary bodes a bittersweet background as it is also the fourth annual Memorial Convoy celebrating the life of founder Brandon Gerwin.

The celebratory cavalcade is not the only event planned for the mid-summer weekend. Amy Gerwin and Jeff O’Brien shared that Brandon never wanted a funeral. To honor his wishes, a bonfire, hog roast, and live music will aide in this time of fellowship on May 22nd, 2021.

“We bought our first truck, I quit my job and started driving,” Brandon said in a 2015 interview with Focus on Fond du Lac. “One of my favorite phrases from several of our employees is, ‘If you don’t like something at Legacy, just wait until tomorrow because it’ll change.’ 

“They mean it in a positive way. We tend to adapt, grow, and change on a daily basis. We do it to benefit the people that are working with us.”

As both founders’ fathers were drivers, trucking truly ran in their blood. O’Brien reflected on his time with Brandon at their previous employer and some of the conversations that began the legacy of Legacy Express.

“There was a trucking company local to us where the owner had been looking to get out of the business,” said O’Brien. “I brought this up with Brandon and he said he’d looked at that company as well. We decided to start from scratch instead.

“That’s how the conversation really got started that we would do this thing together.”

O’Brien keeps his partner’s memory alive by incorporating his hobbies and interests present throughout the company. The driver's lounge is decked-out with a Harley Davidson theme, per Brandon’s interest.

Brandon’s mother, Amy Gerwin, left her career in education and joined the company prior to her son’s passing. She now works as the Human Resource Director at Legacy Express, a company experiencing great growth and prosperity. 

“They all call me Mama Bear because I’m always worried about everyone,” Amy said. “We have drivers that have been with us since the beginning. They stay because it is more than just a job, they are more than just a number. We are a family here.

“An OTR driver called me recently and told me that he is going to be here for the celebration this May. He is coming all the way from Alabama just to make it.”