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New Edition of a Classic Story: Made in KC Founders Lead Group Buying Rainy Day Books How they plan to expand its legacy with next chapter

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Above image credit: Entry of Rainy Day Books. (Channa Steinmetz | Startland News)
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When the owners of Rainy Day Books announced they were selling their popular bookstore in May, they looked for two qualities in its new owners: a commitment to uphold the customer experience and determination to grow the business.

“It has been a six-month process to find people who could understand and embrace my mother’s life experience and legacy. Her whole idea was to use books to bring people together to talk about things that matter,” said Geoffrey Jennings, the lead inventory buyer and event producer for Rainy Day Books and son of Vivien Jennings, who opened the bookstore in 1975 in Fairway, Kansas. 

Rainy Day Books has now been purchased by an ownership and investor group of 16 individuals. Within that group include the three owners of Made in KC — Tyler Enders, Keith Bradley and Thomas McIntyre — who will operate Rainy Day Books and strategize how to expand the business while keeping its charm, Enders shared. Made in KC already operates a rapidly expanding network of retail marketplace, neighborhood shops and café concepts across the city selling locally made goods.

“From a customer experience standpoint, nothing’s going to change,” said Enders, whose Made in KC also runs Front Range Coffeehouse & Provisions in Fairway — just steps away from the bookstore. 

“What we would like to do is add more hours so that everyone has a chance to make it to the store,” he continued, noting that the bookstore is only open from 10 a.m. to 4 p.m. Monday through Saturday. “So as part of that, we will be adding some new positions.”

Tyler Enders, Keith Bradley and Thomas McIntyre of Made in KC.
Tyler Enders, Keith Bradley and Thomas McIntyre of Made in KC. (Natalea Bonjour | Made in KC)

Rainy Day Books found a special niche through Author Events in the late 1980s, Jennings shared. A handful of the celebrity authors who Rainy Day Books hosted and interviewed included: Jimmy Carter, Malcolm Gladwell, Gloria Steinem, Martha Stewart, Hillary Clinton, Anne Rice and Ken Langone.

Enders and his team plan to lean into Author Events by reaching a larger audience who identify as readers but might not know of the local events, he said. 

“We just really think it’s a special part of what Rainy Day Books does and what it provides for the community, so we plan to hire an event coordinator,” Enders said. “In 2019, they had over 300 events, which is just amazing. … We will be looking to increase revenue, both through the existing store and through events, and that’ll be step one before we look at anything outside of the existing footprint.” 

In the future, Enders has early ideas of additional locations for Rainy Day Books, including the new terminal at the Kansas City International Airport. 

“I do think there’s a really good opportunity for us to get a strong Rainy Day presence in the airport,” Enders said. “I don’t think it’ll be immediate, and it might be a little bit of a process, but we are going to do our best to make that happen.”

Vivien Jennings and Roger Doeren of Rainy Day Books.
Vivien Jennings and Roger Doeren of Rainy Day Books. (Carlos Moreno | KCUR 89.3)


A book club composed of notable individuals passionate about Rainy Day Books and the Kansas City community considered purchasing Rainy Day Books when the initial rumors of Vivien Jennings’ retirement surfaced. But they needed the right team to operate the business successfully, said David Von Drehle, a member of the book club, award-winning author and columnist for The Washington Post. 

“My first experience of Rainy Day Books was as an author coming into town to promote my first two books,” Von Drehle recalled, noting that he later moved to Kansas City and became a regular and friend of Rainy Day Books. “Authors can tell you that when they travel on book tours, the bookstore’s skill to deliver an interested audience is extremely variable. A lot of bookstores don’t do it very well, and a few bookstores do it pretty well. Rainy Day Books does it better than anybody in the country.” 

Understanding how exceptional Rainy Day Books is to the publishing community, Von Drehle asked Vivien Jennings and Roger Doeren — her life partner and former chief operations officer — to not sell the bookstore until a perfect fit was available, he said.

“I was sure there were the right people to carry on the legacy, somewhere, but they wouldn’t necessarily have the ready cash to do it,” Von Drehle said. “They reacted well to that, and ultimately that’s exactly what happened.”

One of the advisory board members for Made in KC, civic leader and businessman Bill Gautreaux, just so happened to also be in Von Drehle’s book club — a connection that allowed for all interested parties to combine their funds with others’ retail experience to create a robust team, Enders said.

“When Bill found out that we were interested [in Rainy Day Book], he re-engaged some of those people in his book club,” Enders said. “It was fascinating to hear that their love and concern for Rainy Day Books spurred these conversations years ago, and it all culminated so beautifully.”

Other investors include: Christy Gautreaux, Kathy Donovan, Mark Donovan, David Gentile, Leigh Nottberg, Tyler Nottberg, David Von Drehle, Karen Ball, Mike Stradinger, Jennifer Stradinger, Greg Maday, Liz Maday, Curtis Krizek and Kent Barnow.

Shoppers at Rainy Day Books.
Shoppers at Rainy Day Books. (Channa Steinmetz | Startland News)

In the ‘Living Room’ 

Although Vivien Jennings decided to retire at 77, she will not be fully stepping away from the bookstore, her son said.

“She envisions her retirement as going into the store to talk to customers old and customers new about books and helps matchmake them with new ones,” Geoffrey Jennings shared, adding that since she only lives half a block away from the bookstore, it would be impossible to stay away. 

The family and team at Rainy Day Books is excited to watch it expand to new locations across Kansas City, but the storefront in Fairway will always serve as an extension of the Jennings family home, he continued. 

“When you come into Rainy Day Books, you’re coming into the family’s living room. All of the family — my sister, my nieces, my nephews — we’ve all spent more time in the bookstore than we’ve ever spent in my mom’s living room,” Jennings said. “It is because we all love to talk about books, and that’s the same experience we share with customers. Tyler and his team embrace this very much, which makes us excited because we want to preserve this experience for generations to come.”

Channa Steinmetz is a reporter for Startland News, where this story first appeared. Startland News is a member of the KC Media Collective.

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