From struggling student to invested entrepreneur: Rudy of Rudy’s Cigar Shop shares his story

In grade school, Rudy Mahara had a difficult time with academics. 

“I owned that detention hall," he says. "I had really struggled with grades…. I was just a spirited kid that everybody knew who he was because they didn’t know what he was gonna do next.” 

Mahara's junior year of high school, he had straight F’s on his report card—something he boasted about to friends at the time. 

These days, Mahara is far from a teenager with bad grades in a detention hall. He’s a business owner and semi-retired financial planner in Fort Wayne, where he says that local leaders in Junior Achievement changed the direction of his life and helped him apply his skills in ways traditional classwork didn’t.

Portrait of Rudy Mahara from the top deck showing neighboring homes and properties at Rudy's Cigar Shop.

On the block catty-corner to Parkview Field, mixed in with residential properties, you’ll find one of Mahara’s best-known businesses, Rudy’s Cigar Shop. It’s an old house that’s been renovated and turned into a storefront that sells premium cigars, Indiana beer and wine, and DeBrand Fine Chocolates. Out back, there's a beer garden with firepits near Parkview Field that’s open year-round. 

Rudy’s has been a hotspot in the Downtown social scene since it opened in 2013, inspiring the revival of its surrounding block, known as Brackenridge Village.

Neighboring properties next to Rudy's in Brackenridge Villiage.
So how did Mahara go from struggling student to invested entrepreneur?

In some ways, it started with that report card full of F’s, which brought his dad into school to meet the principal. His father was ready to discipline him for the low grades and pull him from his extracurricular activities. But the principal offered different advice: "Don’t pull him from the areas where he’s excelling—his extracurriculars. Let us worry about the academics."

Mahara says this advice to his father made a big difference in his life and kept him involved in Junior Achievement (JA), one of the extracurriculars where he was excelling. 

Mahara joined JA his sophomore year of high school in Lafayette, Ind., following in the footsteps of his sister. He says JA functioned differently in his time than it does now. Back then, students had companies where they designed products and coordinated the manufacturing. They were responsible for selling and distributing products. They sold stocks and paid profits back to stockholders at the end of the year. 

Portrait of Rudy Mahara in front of Rudy's Cigar Shop.
Mahara found success in JA's business program and was recognized with the local Salesman of the Year award his first year. By his second year—the same year he had straight F’s—he was President of his JA Company, and he competed at the regional and national level for Salesman of the Year.

In his third and final year with JA, Mahara was President of the Junior Achiever Association and President of his JA company. He says the program gave him self-worth, a chance to experience success, and taught him how to run and start a business. 

“I do believe the humor—now it’s humor—of being a dysfunctional child with bad grades and no direction, and the direction was found in an area of success that Junior Achievement gave me," Mahara says. "It gave me the confidence, the personality, and the skills to be able to start stuff up."

And start he did, from Rudy's to the Fort Wayne Boy & Girls Club, to his financial planning business.

"I got to have that startup mentality with education and experiences and the wherewithal to see the pieces come together,” Mahara says.

The humidor cigar room features a variety of cigars at Rudy's Cigar Shop.
While JA looks different today than it did in his time, Mahara says the lessons and skills students gain in the program remain important and much needed in Northeast Indiana. Today, students participating in Junior Achievement learn financial literacy, work and career readiness, and entrepreneurship through programs and lessons taught by local volunteers. 

Mahara himself has previously volunteered as a teacher for Junior Achievement of Northern Indiana, as a way to give back to the program that benefited him. 

As he discusses his life and his work since high school, he reflects on how those skills he learned in JA helped him find his own version of success. After completing a two-year program at Vincennes University, he used his entrepreneurship skills to work for his fraternity, Sigma Phi Epsilon, where he traveled to different college campuses to help the local chapter leaders create business plans and complete brotherhood education.

One of the covered, outdoor seating spaces at Rudy's.Then, Mahara went back to school at Purdue University where he spent some time training managers for a restaurant chain before becoming a general manager in Chicago. Eventually, he moved back to his hometown, Lafayette, and started working in insurance. 

Mahara says it was intended to be a temporary gig, just until he found another job. Then he met his wife and was promoted to district manager for the insurance company Equitable in 1987. This promotion relocated him to Fort Wayne, and he’s been here ever since.

Soon after he moved, Mahara was invited to lunch with the head of the National Boys and Girls Club. At the time, Fort Wayne was the biggest city without a Boys and Girls Club. 

Unsure of what exactly a Boys and Girls Club was and unfamiliar with Fort Wayne, Mahara accepted the meeting anyway. Eventually, with the support of local leaders, he got a local Boys and Girls Club up and running here. Today, the Fort Wayne Boys and Girls Club serves more than 2,270 members.

In the early 2000s, Mahara started Mahara Wealth Partners, a fee-based financial planning business. He recently sold the business, and he’s working through the tail-end of a three-year consulting contract with them. 

View from the top deck at Rudy's.
Like his success with the Boys and Girls Club, Mahara’s opening of Rudy’s was an organic, serendipitous process. He had purchased the property at 409 West Brackenridge St., along with others in the area, unsure of what to do with them. On a whim, he applied for a liquor license and was approved within two weeks. He says in the 50 years since these liquor licenses originated, no one had ever attempted to acquire a liquor license in this area of Downtown. He bought some items from the closing cigar shop he frequented, Esquire Cigar, including humidors, wine racks, lockers, and 1800 dried-up cigars. 

“I said to my wife, ‘Well maybe that building we got a liquor license for Downtown ought to have something to do with beer, wine, and cigars,’” recalls Mahara.

As the city started to develop the section of Downtown near Parkview Field, Mahara sold some of his properties to the city. He used the profit from those sales to renovate the little blue two-story Victorian-era house that would become Rudy’s Cigar Shop.

Along with building a business of his own, Mahara uses Rudy’s to support other Indiana small businesses, too. He only sells beer and wine made in Indiana, updating the selection a few times each year. He also sells Debrand’s Fine Chocolates made locally in Fort Wayne. 

Interior at Rudy's, 409 W. Brackenridge Fort Wayne.
Even so, the main attraction at Rudy's is the namesake cigars, some of which are exclusive or only made in small quantities. Mahara says cigar connoisseurs from all over the U.S. shop at his online store, and locals who once frequented Esquire now visit Rudy’s.

As far back as high school, Mahara has had an interest in cigars himself. He credits his experience at Esquire for his taste, which has only grown more refined with time as he runs his own shop.

It’s not really about the cigars for him though. Instead, much like his interest in supporting the next generation of students and entrepreneurs, Mahara sees his shop as an opportunity to invest in people and relationships in ways that transcend numbers, grades, and titles.

He describes Rudy’s as a sort of church, where all types of people gather. If you visit, you won’t find him pouring beer, or running the cash register, but you will find him talking with guests, commiserating about their problems, and celebrating their successes and milestones. 

Rudy Mahara pours a glass of Rudy's Indiana Summer table wine made by Country Heritage at Rudy's.“I don’t care if we ever sell a cigar or a bottle of wine,” says Mahara. “If we have another vehicle where we can touch that many people that way, that’s fine…. I’m enjoying the highlights of their lives. So for me, it’s so enjoyable to be touching people's lives and trying to throw a ripple in the pond and letting that ripple grow. Rudy’s has given me that.”

After all, sometimes, a small investment in one person has the power to change a community.

This story is part of a series highlighting the faces and stories of economic development in Northeast Indiana, made possible by underwriting from NiSource Charitable Foundation and Junior Achievement of Northern Indiana.

Read more articles by Brittany Smith.

Brittany Smith is Input Fort Wayne’s Assistant Editor. She previously worked for Northeast Indiana Public Radio and participated in the College Input Program.