Serial entrepreneur Bob Monahan takes risks, accepts failures, carries on with renewed energy

Bob Monahan

In 2014, he was cited as someone to watch, spotlighted in the Duluth News Tribune’s annual 20 Under 40 feature. At the time, Bob Monahan was 36, two-and-a-half years into his gig as proprietor/creative director of Chaperone Records and just launching the Red Herring Lounge. This spring, the Red Herring shut its doors, and Chaperone Records is just a memory. Monahan, however, is as energized as ever with his newest business venture, Hostel Du Nord, which opened last October in the former Garon Bros. Jewelers building at 217 E. First St. in Duluth.

Those who have watched Monahan’s career will have observed that he shares a number of qualities essential to leadership. He’s repeatedly demonstrated initiative, enthusiasm for his projects and a willingness to take risks. As one of his former employees recently said, “He makes life fun. The energy changes when he’s in the room.” 

He’s also surprisingly candid about his failures. When asked to share some of the lessons he’s learned through his various ventures, he openly delivered a handful of insights that may prove helpful for other regional entrepreneurs. 

The entrepreneurial bug

Monahan’s interest in going into business emerged slowly. After graduating high school in 1997, hereceived his degree from Area Learning Center in Duluth via Roseville Area High School and began attending classes at Lake Superior College. 

“The subsequent years were consumed by the search for myself and a compelling argument for why I should go to college when I had no idea what I wanted to go for,” he said.  

Taking a break from school led to a circuitous career path that included a period overseas.

“When I was living in New Zealand, I was trying to figure out the next step in my life.” Not having a college degree felt like a limitation on his options.

His first foray into business was as co-owner of Medicine Bear Design, a jewelry and T-shirt business that was open from 2003-2006. 

“One lesson I learned was that pushing products on a small scale is tough. You’re competing with mass production,” Monahan said.

His second venture involved the trending biodiesel market. Along with seven others, Monahan became a founding member of the Duluth Biodiesel Co-op (2005-2006). His awareness of the emerging alternative fuels wave led him to buy a school bus having a wheelchair lift, which was converted into a camper so they could transport biodiesel from Brainerd in 55-galllon drums.

The opportunity seemed real, but challenges of the endeavor were not immediately apparent. 

“Margins were tight. We learned that to maintain a customer base we had to stay price competitive with diesel. Some customers didn’t want to pay even three cents more per gallon.” As a result of this and other issues, they struggled to make rent. 

Out of the ashes of that experience, Monahan jumped into a parallel venture as co-owner of Greencylers Cooperative,a business devoted to waste vegetable oil collection and recycling into fuel (2007-2008). This venture, too, was enthusiastically embraced but short-lived.

“The most obvious lesson was to start with all the capital you're going to need for a year of operations. Start with capital, in general,” he said. “Businesses operating on a shoestring are bound for failure. You can have the best idea in the world, but if you can't fund the operation, you're done, son. That being said, if it's a partnership, go into it with someone who can pull their weight, financially – especially with a startup. Money is way better than sweat equity when you're just getting something off the ground.”

Many of Monahan’s businesses were run simultaneously, with overlapping time frames. Another business he initiated was Jimmy's Vintage, a vintage clothing resale business that he co-owned with his friend Jimmy Henry from 2007-2011. 

“Jimmy Henry rode a bicycle here from Portland, Ore., with only a backpack and a sign that he'd hold at the foot of hills that said ‘LAZY.’ He was a poet, philosopher and the snappiest dresser I've ever met,” Monahan explained. “The sole reason Jimmy and I made any money on vintage clothes is because our only overhead was the price of gas to the cities and back, and gas was cheap.”

In 2008, he became involved with Bohemia Arts as co-owner (2008-2009), located in the storefront now occupied by Blush. He also founded Goat Hill Honey, of which he was owner and head beekeeper, also a retail business (2008-2011)

“Bohemia Arts taught me a fair amount about retail and how I would not ever like to be in that line of work,” Monahan said. 

“These small-scale retail operations – most of my business ventures, in a nutshell – were an attempt at cracking into a market that really wasn't all that hospitable. Lots of competition and everyone looking for a bargain. I'm not sure what all I learned from those ventures besides the necessity of keeping your overhead down, but that's Business 101 stuff,” he explained.

Throughout this period, Monahan returned to taking classes, obtaining his AA degree from LSC in 2010.

Chaperone Records

Monahan’s involvement in the local music and arts circles prompted him to take advantage of a void he identified, as well as the vinyl trend in the music scene. The result was Chaperone Records (2012-2017), in which he served as president. 

“After being laid off from yet another seasonal serving gig, an intense fear of boredom and tediousness thrust me towards another hare-brained entrepreneurial adventure,” he said. “Chaperone Records proved to be a crash course in the highly competitive music industry, which is a many-headed Hydra. ‘Payola’ in a sense is still alive and well.” 

Monahan can tell many stories about his experiences in the record industry. 

“One year, we participated in South by Southwest, which proved to be a bit of a joke, especially when it comes to the big stage. Either you’re in or you’re out. It’s a microcosm of the industry.”

At a certain point, Bob hired a business coach. When asked what time he starts his day, he said around nine. 

“I found that by switching from 9 a.m. to 8 a.m. my productivity increased significantly.”

The Red Herring years

In 2014, he founded the Red Herring Lounge, which seemed to dovetail with his music scene activities. 

“Essentially, I bought myself a lifestyle,” he said. “With each business, though, I continued to up the ante. More employees meant more risk.”

A number of issues arose pertaining to hiring. 

“First, good help is hard to find. Another error I made: I essentially hired people so I could do as little as possible. Another problem also emerged. Because the Herring had a family feel, the lines between owner, employees and friends became blurred.”

Midway through the second year, the lounge business had peaked. This issue regarding hiring and management of employees began to rear its ugly head and morale started to suffer.” 

Monahan, seasoned by two decades of experience, took this to heart, realizing that his Red Herring business had been a sidetrack, that he had been “partying for a living.”

Monahan shared how he turned for advice to his mother, who had been a Unitarian minister for 25 years. She said,“Desire must find its end.” With the closing of the Herring, he’s turned the page. 

His latest business venture is Hostel Du Nord.  With his new company, he’s brought a new attitude with a desire to succeed. 

“I mismanaged myself for years,” he said.  

Experience has made him wiser, and he continues to emanate an upbeat exuberance. When asked about his biggest influences, he replied, “Richard Brautigan, my parents, rap music, Bob Dylan, everyone who genuinely cares about their fellow human beings – and life, in general – and all of my shrinks that didn't suck.” 

One of the biggest takeaways from this story has to be that Bob Monahan is clear evidence that the entrepreneurial spirit is alive and well in the Northland. A lot of folks will continue to root for adventurers like Monahan who are trying to make things happen.