Cyrus Jaffery: 2023 Entrepreneur of the Year

Cyrus Jaffery is the founder and CEO of Jaffery Insurance & Financial Services, but that’s not all. He’s also the founder & CEO of Quotamation, a new venture that provides insurance agents with a quoting tool that rapidly produces information from more than 20 carriers. Plus, he’s in joint ventures with about a dozen industry partners who work primarily with mortgage and real estate companies or banks and credit unions across the country.

“We own majority and then the partner owns a piece of it as well,” he explained. “We share revenue and we run the day-to-day.”

There’s even a book coming out about him at the end of the year, authored by local writer Leo Adam Biga and encapsulating a message of perseverance.

Jaffery is clearly a rising star in the insurance sector, but it wasn’t his intended career path. Neither was entrepreneurship. When he entered college at Nebraska Wesleyan, Jaffery’s Afghanistani family, who relocated to the U.S. as refugees in the early 2000s, expected he would eventually practice medicine or law.

“When you are from a different country, your parents want you to be either a doctor or a lawyer; I guess to them, [that means] you’ve made it in life,” he said. “I was pre-med, I went to biology class as a freshman in college, and I literally hated it. So, the next best thing was getting a political science degree so that I could go to law school.”

Law school never happened, however. Jaffery’s first glimpse into the insurance business was during a visit to his then-girlfriend’s family. Curious about their obvious prosperity, Jaffery asked his future father-in-law about his career — which turned out to be insurance — and saw a potential fit.

“I kind of just fell into it,” Jaffery said.

Cyrus Jaffery, founder & CEO, CJ Insurance Group. (Photography by Debra S. Kaplan)
Cyrus Jaffery, founder & CEO, CJ Insurance Group. (Photography by Debra S. Kaplan)

After working for an agency for six years, Jaffery became independent in 2019, driven by the idea of creating a business in which his children could join him one day and also craving more autonomy and growth potential. He also wanted to provide similar opportunities to others. 

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Three of his siblings, Ahmad, Bobby and Suman, have joined him in business, bringing various skill sets to the table.

“When you’re starting a new business, you want to find your core people that you can completely trust,” Jaffery said. “It’s been quite fun and rewarding to help family, but at the same time I’ve been able to see them grow on a daily basis and take our organization to the next level.”

Jaffery’s wife, Michelle, is also involved. The couple are raising three children, now 6, 4 and 2. Jaffery, whose LinkedIn profile leads with “Husband” and “Father,” promised his wife he’d be done with work by 4:30 p.m. daily and keep weekends free for family. 

“Twenty years from now, nobody will remember those late hours that you had at work but your kids,” he said. “One of those things to get to what’s next for me is to figure out how I can accomplish more in those seven hours of work that I get and do all the things that I want to do, but at the same time, do a really good job of being a father and being around for the kids and as a husband as well.”

Creating efficiencies was part of the inspiration for Quotamation, and Jaffery said he’s looking at other ways to streamline and automate “so I can have more time to make an impact” not only in his growing businesses, but spending time with his family, hosting his podcast, and contributing to nonprofits and community organizations. 

“That impact… can make a difference, which is the biggest thing for me,” he said.