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Radio Cherry Bombe

Substack Star Caroline Chambers Live At Jubilee

Radio Cherry Bombe

The Cherry Bombe Podcast Network

Kerry Diamond, Women In Food, Women, Chefs, Society & Culture, Cherry Bombe Magazine, Entrepreneurs, Arts, Business, Food, Food Radio, Talk Radio, Careers, Radio Cherry Bombe, Restaurants, Female Chefs, Restaurateurs, Interviews, 591312

4.6592 Ratings

🗓️ 28 July 2025

⏱️ 30 minutes

🧾️ Download transcript

Summary

Hi, listeners! Host Kerry Diamond here. Welcome to the show notes, and thank you for listening. If no one has told you lately, you clearly have great taste in podcasts. Today’s guest is Substack queen, bestselling author & boy mom Caroline Chambers recorded live at Jubilee NYC, Cherry Bombe’s annual conference. (Curious about Jubilee? Join us at the upcoming Jubilee in L.A.) My favorite thing about Caroline? She doesn’t gatekeep. I’ve interviewed her a few times now, and she is always happy to spill all the details regarding her Substack and how she wound up with the NUMBER ONE SUBSTACK IN FOOD AND DRINK. Amazing. Here’s the leaderboard if you need proof. (For Caroline’s Substack success step-by-step, check out our pod from last year.) She also talks about being rejected by all the cookbook editors when shopping the proposal for “What to Cook When You Don’t Feel Like Cooking,” which, of course, went on to be a major hit. That must have felt nice when the book made The New York Times bestseller list. (Cue the “Pretty Woman” big mistake scene.) Few more things. Thanks to Michelladonna of “Shop Cats” (happy belated birthday, M!) and Alice Ma of Mad Realities for introducing Caroline at Jubilee. Big thanks to Square for supporting our show and taking care of so many small businesses. Check out what they’re up to at square.com/big. And go visit Este Restaurant if you’re in Austin. Lastly, congrats to Caroline and her hubby on their new baby–their fourth boy! So many boys. If you have a Substack, I want to know about it. Email us at info@cherrybombe.com and put something funny in the subject line so we have no choice but to open your email. Join the waitlist for our Summer Tastemaker Tour. We have a print magazine. Subscribe here. You’re the Bombe.

Transcript

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0:00.0

Hi, everyone. You're listening to Radio Cherry Bomb, and I'm your host, Carrie Diamond. I'm the founder and editor of Cherry Bomb magazine. Today, we're airing my interview with Caroline Chambers from this year's Jubilee Conference in New York City.

0:18.8

Caroline is a best-selling author, recipe developer, and a

0:22.1

substack superstar. Her wildly popular newsletter, What to Cook When You Don't Feel Like Cooking,

0:27.6

is one of the top substacks in food and drink. Caroline shares how motherhood and life as a military

0:33.4

spouse shaped her path, the creative and strategic moves that helped her find success on social

0:38.6

media and substack, and all the rejection she faced when shopping around her cookbook.

0:44.2

Caroline, by the way, is a brand new mom and just welcomed her fourth child and fourth boy

0:48.8

into the world. Congratulations, Caroline. We're all so happy for you and your family.

0:55.6

Caroline was introduced by Michelle Adana, a New York City comedian and star of the Shopcats show on Instagram, and Alice Ma,

1:02.1

co-founder and CEO of the Social First Media Company, Mad Realities. Today's episode of Radio

1:08.6

Cherrybaum is presented by Square. Some of you might not know this, but years ago, I owned a cute little coffee shop in Brooklyn. I sold it because I couldn't do Cherrybaum and the coffee shop at the same time, but I learned so much about running a small business and having a brick-and-mortar location. One of my favorite tools was our Square POS. We did everything from there, ring in sales, keep an eye on inventory, and track the discounts we offered every time customers brought in their reusable coffee cups. I appreciated how easy it was to use for me and the team. Training was a snap because the interface was so clean and well designed. Today, Square, Square, the point-of-sale technology that

1:45.4

helps you manage everything, from payments to staff, customers, insights, and lots more,

1:50.6

has the backs of more than 7 million businesses. The team at Square knows how hard you're hustling

1:55.8

to keep your businesses alive and thriving, and that you're looking for ways to save time

2:00.5

and be more efficient.

2:02.4

Just in time for summer dining, Square has a new lightweight POS device that literally fits in

2:07.6

your pocket. Called Square handheld, it lets you take table-side orders, process payments, and manage

2:13.5

inventory. I would have loved to have had that back in the day. When your restaurant is on your mind,

2:19.0

which is probably all the time if you're like I was, think big and stress less with Square.

2:24.3

Go to square.com forward slash big to see how Square can help you. That link is in our show notes.

2:31.3

Our next Jubilee conference is taking place in Los Angeles on Sunday, September 28th.

2:36.8

If you're new to Jubilee, it's our conference that's all about connection, community, and

...

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