biography

With more than 15 years of experience as a financial advisor, Jennifer Chesini has well-rounded expertise, which encompasses everything from hedge funds and private equity analysis to high-net-worth financial planning and portfolio management.

Though she began her career in the San Francisco Bay Area, Jenni first met both of her co-founders in 2002, while attending California Polytechnic State University in San Luis Obispo. At the time, Lyle managed a local financial advisory office and had recently hired Dan. Unable to find a local financial firm offering internships, she sent Lyle a letter, offering to work for free and promising to do a good job. A week later, she called him to follow up and he offered to give her an opportunity. While interning with Lyle and Dan, she realized she could combine her love of numbers with her desire to teach and help people.

“I find being an advisor very fulfilling because you can truly make an impact on people’s lives,” she says. “I started managing real money in 2001, ‘playing’ with a small Ameritrade account that belonged to my parents and then managing a portfolio of endowment money as my senior project. Investing can be scary, but our job is to alleviate that fear for our clients as much as we can and help them achieve their financial goals. When we accomplish that, we genuinely make a difference.”

Following graduation from Cal Poly with honors in 2003, Jenni worked first in Lockheed Martin’s finance department and then as a financial advisor, passing the CFP® exam in 2005.

After years working in the Bay Area, she met and married a farmer from her hometown in the northern Sacramento Valley and relocated to be with him and start their family. In 2017, she contacted Lyle for advice, and he invited her to join him in his practice in San Luis Obispo, bringing her career full circle to where it began. 

Jenni along with her husband Dan and their three sons live in San Luis Obispo where they enjoy outdoor activities including camping, hiking, and going to the beach.

fun facts

  • She rode horses competitively from ages eight to 20, competing in hunter/jumpers as a child and then in high school and college rodeo.
  • Won the “Poly Royal” in breakaway roping as a freshman at Cal Poly and holds numerous English and Western riding championships.
  • Jenni has been sky diving twice, once in college and the second time with her husband over Pismo Beach for their first wedding anniversary.
  • Although she never lived in the dorms while attending Cal Poly, Jenni now lives with her family on campus thanks to her husband’s job as Cal Poly farm manager.