Fast 15: Sam Chesshir
by May 4, 2026 8:00 am 869 views
Sam Chesshir was an intern at Little Rock-based Stephens Inc. when a mentor there suggested looking into AcreTrader.
“AcreTrader was still in the high-growth startup phase,” Chesshir said. “It was 2023. We had raised a series B at that point. Acres.com wasn’t even available to the public. It wasn’t even a separate business yet.”
Chesshir’s father provided the following guidance, leading him to join AcreTrader. “Don’t just go where the business is already built,” his father said. “But go where you can be part of the building process.”
The experience he’s received at AcreTrader over the years “at such a young age is really incredible,” he said. The opportunities he’s had there have developed in him a passion for finance.
He joined the company in 2023, and in the first five months, he secured more than $1.1 million in new investments and developed relationships with 40 new investors. Within six months, he earned three FINRA securities licenses.
The Little Rock native moved to Northwest Arkansas to attend the University of Arkansas in 2019. He earned a bachelor’s degree in finance with an emphasis on investment management in May 2023 and a master’s degree in finance in December 2025.
From late 2023 through 2024, he worked on the buildout and launch of Acres.com.
He returned full time to AcreTrader in 2025 and leads the company’s investor relations, supporting thousands of investor accounts that have collectively invested more than $400 million through the AcreTrader platform. He also leads retail investor marketing efforts.
Chesshir served as an analyst on the acquisition of AcreTrader by Minneapolis-based private equity firm Proterra Investment Partners, which completed the acquisition in 2025.
“I’ve now gotten to work on one of the largest row crop transactions in history that was, to my knowledge, top five row crop transaction ever occurred of investable-grade row crop ground in agriculture,” he said.
His career highlight has been “being the kid in the room, the young guy in the corner that’s sitting with senior leadership learning how to run one of Arkansas’ most premier fintech businesses.”
He speaks at Greek life events, mentors Phi Delta Theta members, and is a member of Central United Methodist Church and Bible Study Fellowship. He enjoys fishing, duck hunting, gravel biking and tennis.