The Grumpiest Billionaire

Small Town Sisterhood #2

by Pippa Grant

From USA Today and #1 Amazon Bestselling Author Pippa Grant comes a witty road trip romcom about a billionaire on the run and the last woman on earth he wants in his passenger seat...

That didn't turn out the way I planned it.

All I wanted was five minutes with Oliver Cumberland to explain to him that proposing to my sister — again — is a bad idea.

Instead, I'm now trapped in his car, on a cross-country road trip I didn't anticipate, attempting to talk the grumpy billionaire out of something much, much worse than an arranged marriage for business purposes.

I don't care if Mr. Square Jaw McMoneyPants wants to give away his entire fortune and disappear to live out his life working the popcorn counter at a movie theater or whatever in Podunk, USA.

But I do care that dozens of non-profits will lose their funding without Oliver in charge of his family's empire. After all, I work for one.

I have to convince him to go home.

But by the end of the first week of our (mis)adventure, one thing is becoming obvious:

Oliver refusing to return home is the least of my problems.

The fact that I'm starting to fall in love with my sister's ex is the real issue.

The Grumpiest Billionaire is a runaway billionaire road trip romance featuring a man who's tired of taking responsibility for everyone around him, a woman who's made a lot of mistakes while on a lifelong mission to save the world, and a slew of unintended consequences that prove no good deed goes unpunished.

Genres: Romance, Road Trip, Enemies To Lovers, Audiobook, Fiction, Rom Com, Billionaire Romance

376 pages, Paperback

First published January 8, 2026

About the author

Pippa Grant wanted to write books, so she did.

Before she became a USA Today and #1 Amazon bestselling romantic comedy author, she was a young military spouse who got into writing as self-therapy. That happened around the time she discovered reading romance novels, and the two eventually merged into a career. Today, she has more than 30 knee-slapping Pippa Grant titles and nine published under the name Jamie Farrell.

When she’s not writing romantic comedies, she’s fumbling through being a mom, wife, and mountain woman, and sometimes tries to find hobbies. Her crowning achievement? Having impeccable timing for telling stories that will make people snort beverages out of their noses. Consider yourself warned.

Reviews

[Laura · Rating 4 out of 5]

a grumpy sunshine romance with a billionaire is going to do it for me every single time. especially when it’s a rom com.

devoured this book whole in less than 48 hours and I loved every single second.

[CiCi | bookameme · Rating 5 out of 5]

I love this book so much!!

Pippa never fails to make me laugh. The crazy hijinks she puts these characters through is unexpectedly expected, meaning I expected her to make it crazy but I wouldn’t have imagined the things they did. Add to that a swoon worthy steamy romance and the best cast of side characters popping in and this is easily a new favorite.

🎙️: (Duet narration & POV)The narrators were fantastic!

Romcom
Road Trip
Older Sisters Ex Boyfriend
Found Family
Sisters by Blood & Sisters by Heart
Hurt/Comfort
Riches to Rags (kinda)

🌶️🌶️🌶️: A few super steamy explicit scenes 🔥

[Patricia (Spellbound Stories Trish) · Rating 5 out of 5]

Daphne is a wild, messy genius! I love her character so much and I am so happy she got her wildest dreams to come true, even if she didn’t know she had them!!

Daphne and Oliver are OPPOSITES is every way possible like I mean what the heck these two will more than likely off each other than kiss and well Oliver came close several times hahaha!

This story was so hilarious but also full of heart! I love the blanace that Pippa infuses into her novels. Each book is such a grand adventure because you know you’re going to laugh but also prepared for the emotions when things get real. Her characters are so relatable and I have loved Daphne so much and this book only made me love her more!

Another top read and the best book to start 2026 with!

[Ally Bateman · Rating 4 out of 5]

This story was fun. A runaway Billionaire and a ex-heiress with life skills go on a road trip to give away millions of dollars and be free from their parents expectations. This was a grumpy-sunshine, forced proximity, enemies to lovers, buddy comedy. I’m glad that Daphne’s character developed away from her being a manic pixie dream girl and into a real character with substance and purpose. Also bonus points for no third act breakup.
I’m looking forward to where we go in book 3.

[Sarah · Rating 4 out of 5]

This is a cute and rather serious romance at times, but the best part of it (to me) is the relationship between Daphne and her sister, Margot. I love my sister. She's my best friend, and we'd both do anything for each other, so whenever I read about sisters being so good to each other, it stabs me in the heart (in a good way).

As far as the relationship between Daphne and Oliver, it is pretty funny. Oscar has no idea how to survive in the real world (the world outside of his privileged upbringing), but Daphne is a good teacher, having escaped her own upscale life. He is kind of a prick to her in the beginning, though, and I'm not sure I'd be as forgiving. But, when it matters, he has her back and becomes such a cutie. 🥰

It's definitely a smutty, fun story, and of course, I love the animal friends (both in plushie form and real form), plus the references to food (there's a lot of fish and chips and spicy cheeto type snacks(?)). Seriously, I get so hungry reading Pippa's books. haha

Anyway (how do I end a book review, again?), I woke up at like 2am and then stayed awake for 2 hours just to finish this book, so I guess that means I liked it. ✌️

[Courtney Miller · Rating 5 out of 5]

This was so fun! I love Oliver and Daphne. We get peaks of Bea and Simon, but seeing the craziness of Daphne take over Oliver was so fun! I adore Pippa, she’s an auto read for me and this is once again, brilliant

[Emily · Rating 4 out of 5]

Oliver couldn’t be wound tighter if he tried. I don’t think Daphne could be anymore opposite of him if she tried. Naturally, a road trip is the perfect thing for these two. Oliver has no idea what he’s getting into. It’s just what he needed. He learns to laugh and love. I think we’ve all thought about running away from home before. He just decides to actually do it. Did I mention he’s an ex of Daphne’s sister?

[CzekMart · Rating 5 out of 5]

The Grumpiest Billionaire is everything I adore about Pippa Grant wrapped into one wildly charming, slow‑burn, laugh‑out‑loud, heart‑squeezing package. From the very first chapter, I knew I was in for a treat — the kind of romcom that makes you grin at your Kindle, reread your favorite lines, and fall hopelessly in love with two characters who feel both larger‑than‑life and deeply, beautifully human.
Jasper is peak grump: guarded, broody, allergic to feelings… and yet every tiny crack in his armor made me melt. And then there’s Ellie — sunshine incarnate, full of warmth, chaos, and the kind of optimism that feels like a hug. Watching these two collide, clash, and slowly unravel each other was pure joy. Their chemistry is electric, their banter sparkles, and their emotional journey feels so earned.
What I loved most is how Pippa Grant balances humor with heart. One moment I was laughing at the absurdity of their situations, and the next I was clutching my chest because the vulnerability hit so unexpectedly and so perfectly. It’s a story about trust, healing, and choosing love even when it scares you — and it’s delivered with the kind of charm only Pippa Grant can pull off.
If you love grumpy/sunshine, forced proximity, swoony billionaires with soft centers, and heroines who radiate joy, this book is an absolute must‑read. It left me smiling long after I finished, and honestly, I’m already tempted to dive back in.
A wholehearted, glowing five stars from me.

[Shelley · Rating 5 out of 5]

Thank you Pippa Grant & team for the ALC of The Grumpiest Billionaire

🎤 Narrated in duet by Mackenzie Cartwright & Jason Clarke

🗓 Release date: January 8, 2026

Review:

This book was so funny and so adventurous. It had me laughing so hard I was crying! 😂

Seriously though, Daphne and Oliver's unexpected road trip was the best thing ever. The people they helped along the way really warmed my heart.

They had some really funny moments together - Everyone checking Oliver's money to make sure it was real... Oliver almost accidentally becoming a stripper for an elderly woman's birthday party (I had to make a graphic for that - one of my favorite scenes!)

This was a slow burn romance and I loved that. All of the tropes were perfect. ❤️

The performance by Mackenzie Cartwright and Jason Clarke was also perfect! They did an amazing job with their characters and I don't think I'll forget Jason Clarke sarcastically saying "It was not on my calendar for today."

Also: This is another book with a magical laundry room. ✨️ 🫧 😉

Be sure to check out this amazing book when it releases January 8th!

[Jenny · Rating 5 out of 5]

A somewhat madcap cross country run away trip, a grump of a billionaire and a surprise stowaway in the form of your ex fiancé’s little sister.

This is pure rom com fun! Daphne brings absolute quirkiness (I feel she’s an Aquarius in her soul) and Oliver just seems long suffering with Daphne’s sunshine.

Oliver has been carrying the burden of his family’s business under great duress because his father was arrested but recently released from jail. On the night he planned to disappear from his life, he starts his road trip and discovers Daphne in this back seat. What happens after is nothing short of hilarious, sweet, heartfelt. Loved their story and that they are both really good people.

5 stars!

[MissPetiteBrunetteBookBlog · Rating 4 out of 5]

Oliver Cumberland just wants to get away from it all! His father, his ex fiancée and his legacy. That is until he finds one Daphne Merriweather-Brown hidden in his SUV during his escape! Now stuck together, she has to find a way to get mr. billionaire to return home and he wants as far away from his ex’s sister as he can. Will she convince him to do the right thing or will this grump start to rub off on Daphne? This is an over the top silly romcom with an annoying little lady and one unhappy billionaire. How could they not work well together lol. Grab your favorite road trip snacks and hang on for a fun ride! Told in first person and dual POV.

[Molly Jaber (Audiobooks And Sweet Tea) · Rating 4 out of 5]

⭐️⭐️⭐️⭐️
🌶️🌶️🌶️
🎧🎧🎧🎧🎧

Pippa Grant has brought us another beautiful installment in the Small Town Sisterhood series. Oliver & Daphne absolutely stole my heart, from their banter to the absolutely slow burning, sizzling chemistry between them. Every second of their opposites attract story kept me hooked and wanting more!

Jason Clarke lent his talents to bring us Oliver. He was perfection! Mackenzie Cartwright is truly talented and did a phenomenal job voicing Daphne. Together, these two nailed every bit of tension, spicy moments, and banter within the story and I a delightful time listening!

[Diana · Rating 5 out of 5]

i love these books so much! i was so excited to get into daphne’s story after finishing the spite date because it left off on a cliff hanger! i thought this story was so adorable how daphne and oliver ended up both needed eachother more than they could’ve ever imagined. i also love the banter and laugh out loud moments that pippa sprinkles throughout her books. all her characters are also so relatable and struggle with things that everyone can relate to. i can’t wait for the next book!!!

[ReadMoreAdultLess · Rating 4 out of 5]

In true Pippa fashion this book had me giggling out loud. These two are so polar opposite that the banter back and forth is epic. I loved how much of a wild child our FMC was, just as colorful as her hair! And our MMC that poor man can’t catch a break and just disappear like he would like to at least without a new sidekick for the trip 😂 if you need a entertaining fast paced read that will make be laugh and feel, you will never go wrong picking up a Pippa delight! Thank you Pippa for the ARC for review!

[Stefanie Simeone · Rating 5 out of 5]

fun read

I almost put this book down after a few chapters as Daphne was annoying me. I decided to continue and her immature behavior still made me cringe. However, I eventually began to understand her and appreciated how she decided to help Oliver.

This book is a testament to the idea that a road trip with someone you love is the ultimate test. If you enjoy it and survive the journey, your relationship is likely to succeed.

[KatReadsRomance · Rating 5 out of 5]

Fun and sweet and oh so Pippa!

I very much enjoyed The Grumpiest Billionaire, book two of the Small Town Sisterhood series.

I don’t know how she does it, but Pippa Grant somehow makes her male main characters, even the grumpiest of billionaires, into sweet boys who are far more than they appear to be beneath their hard and crusty outer shell. There’s an innocence to them that is so refreshing and I always fall in love with them when the first sign of that sensitive side shows itself.

Oliver and Daphne are the most fun people that everyone wants to be friends with, me included!

[Linsey Toney · Rating 4 out of 5]

the grumpiest billionaire is book two in the Small Town Sisterhood series.

I really enjoyed this book! The FMC hides in her sister's ex's car. This slow burn, grumpy sunshine book was hard to put down. You can read this book as a standalone but book one was funny and fantastic so I would recommend reading them in order. If you haven't read a Pippa Grant book yet then I would recommend this series!

[Ashley · Rating 4 out of 5]

What happens when Daphne accidentally crashes her sister's ex-fiance's cross country road trip where he's running away from his life? A whole lot of fun! These two are complete opposite of each other and at first Oliver is super annoyed with her. But what he comes to realize is maybe he needed Daphne in order for him to learn how to have more fun in his life. They seriously balanced each other out so perfectly. This book has the best banter and so many funny moments. Seriously the best rom com!!

🎧Audio:🎧
This was a duet narration by Jason Clarke & Mackenzie Cartwright. Jason played Oliver's broody, grumpy self to absolute perfection. Mackenzie was perfect to play Daphne's fun loving self! These two had amazing chemistry and made this story so much fun.

What to expect:
💖Sister's Ex-Fiance
☀️Grumpy/Sunshine
🚙Road Trip
💵Billionaire

[Hayley 〰 Hayley's Next Page]

- billionaire romance
- sister’s ex-fiancé
- grumpy (him) x sunshine (her)
- opposites attract
- forced proximity (road trip & one bed)
- 🌶️.5/5
- dual pov
- duet narration with Jason Clarke and Mackenzie Cartwright

This is for a paid promotion, so no rating or review, but I had a great time! I hope this isn't the end of this series because I don't want to leave this world yet.

[Michellelovesreading · Rating 5 out of 5]

This book was a 5 star read for me. I couldn’t put it down. I was laughing out loud at this book from the beginning. I was up late reading because this book was so good. I 10/10 recommend reading this book after you read the spite date which is the first book in the small town sisterhood series.

Stars:⭐️⭐️⭐️⭐️⭐️

Spice:🌶️🌶️🌶️🌶️

[Jessi · Rating 5 out of 5]

That was such a fun read. I loved it so much. I always have a good time and lots of laughs with a Pippa Grant book, and this one did not disappoint. I loved Daphne and Oliver together. They had great chemistry, even when they were arguing. I laughed so much, especially after they met up with Simon and Bea. They were fantastic.

[Livy dow · Rating 4 out of 5]

Such a fun read honestly. I feel like I need to see this on the big screen, this could be a cute Netflix romance movie. I love how interconnected it is with the first one. I love seeing the growth between the characters the teeny bit of spice was also okay. And I’m so excited to see what comes next in the series

[RLV · Rating 2 out of 5]

Found this so underwhelming. Nothing happens except for the MCs leaving thousands of dollars in tips everywhere they go. It’s so slow. I liked how the hero sort of found his path and everything but still. It could have been halved without missing anything important. Just… boring I guess.

[kreadsoften · Rating 4 out of 5]

Oliver was definitely grumpy, but he had a soft heart. He was on a road trip to escape his current life, and as a billionaire, he had more money than he knew what to do with.

Daphne was so sweet and a bit of a chaotic (good) mess! She was good for Oliver, even though she didn’t intend to go on the road trip with him.

This was such a cute and funny story. Just like other Pippa Grant novels, the characters are great and the story was entertaining.

[Calla Negra · Rating 4 out of 5]

It's a feel-good book.

[Michellelovesreading · Rating 5 out of 5]

I had the opportunity to read this book and listen to the audio at the same time and it made the book come to life for me. If you can get the audio and read the book. I suggest you do.

Stars:⭐️⭐️⭐️⭐️⭐️

Spice:🌶️🌶️🌶️🌶️

[Samantha · Rating 5 out of 5]

This book was so so funny omg !! The situations Oliver and Daphne got themselves in was hilarious, I love how Daphne helps Oliver find a side of himself that he didn’t know he still had inside of him, everyone must check out this book ,

[Magaly | Catchy Book Nook · Rating 5 out of 5]

I always know that I’m going to enjoy Pippa Grant’s books because she writes charismatic stories that just land for me. That being said, I wasn’t prepared for how much I would love this one.

Road trip books can be hit or miss for me, so while I knew I’d love the writing I wasn’t sure how much the story would grab me. Thankfully, my skepticism was not well-founded. I loved this book so much it became my top read of December. The balance of humor and emotion with the characters felt just right. Daphne and Oliver together are my favorite! A great example of opposites attract and forced proximity. Definitely recommending it!

[Valeen Robertson (Live Thru Books Blog) · Rating 5 out of 5]

Amazon / Website / Audible / Amazon Audio / Paperback



Oliver's on a journey - he's leaving his life behind and escaping to where he can give away his family's money to people who need it. Little did he know the stowaway in his car would change everything - change him, change his course. He wasn't expecting his ex fiancée's sister to happen, wasn't expecting to fall for Daphne, but somehow she's become the most important person in his new life.



Daphne only wanted to tell Oliver to leave her sister alone, but somehow she's now on his journey with him. He's showing different sides to him she never realized. The grumpy billionaire isn't seeming so grumpy now, just tired of his old life. Now he's opening up, enjoying life, smiling, even cracking ridiculous jokes. And her heart's so gone for him. She just can't give him up now, even if her beloved sister finds out and decides she can't support them being together.



I can't remember the last time I enjoyed a road trip romance more than this pair of opposites! Daphne is adorable, a mess, but an adorable mess with a beautiful heart. And Oliver? Oh Oliver...he's perfect. Went from grumpy to the sweetest, loving life billionaire who was changed, healed, by the love of someone he never saw coming. From funny, witty moments to emotional, heart-tugging intimate dialogue, Daphne and Oliver's story has everything I love in romance and I want a lot more of them.



ARC provided by the author for an honest review.

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[Bette · Rating 5 out of 5]

Brilliant & Delightful➞Story & Narration🎧

The Grumpiest Billionaire
Small Town Sisterhood, Book 2
By: Pipa Grant
Narrated by: Jason Clarke, Mackenzie Cartwright

This book was everything, a romantic comedy I did not know I needed until I started it, and wow did I need it bad, it took me away from everything else going on in life, putting a smile on my face and laughing out loud. No one does it quite like Pippa, a story with brilliant dialogue, humor and perfect timing, lots of heart, chemistry and heat. This second book in her fabulous “Small Town Sisterhood” series is Oliver Cumberland and Daphne Merriweather-Brown’s story, an enemies-to-lovers, grumpy/sunshine romance. These two quickly became two of my favorite characters, starting with Daphne, whose personality and sunny demeanor are infectious, and you can not help but fall in awe of her. Oliver, the grumpiest billionaire, has a plan and is out on a mission, and that mission, a road trip that does not include a stowaway in his car. Disowned by her wealthy Daphne, snuck into the Cumberland party in a disguise, and after overhearing something she did not like about her sister Margo, his ex-girlfriend, she went on her own mission, to set Oliver straight. Except she fell asleep in the back seat of his car, waking up at the most inopportune moment, startling Oliver, creating a hilarious scene, one of many. Oliver does not trust her, but she recognizes he could use help in learning how to fit into society and live an ordinary life. She had been in his position when her family disowned her, thrown into the wild without having a clue how the others lived without help, assistants, security and no money, well luckily he still had that and had plans for it. It was great watching these two spend time together, then seeing their relationship morph into something so much more. I loved all the layers of this story and how it all played out, with the perfect balance of drama, a touch of angst, lots of witty dialogue and humor, heartfelt emotions and steamy romance. As always, the writing, plot and world building are fantastic, as are the character growth, especially Oliver, whose transformation was brilliant. Pippa Grant, thank you for another fabulously entertaining story, the laughs and the emotional rollercoaster ride.

🎧📚🎧And for the fabulous audiobook listen, Jason Clarke and Mackenzie Cartwright did a fantastic job voicing these characters, and I loved how they owned each role, sounding believable in every one. Both were amazing as the two leads, with Clarke nailing it as Oliver, starting out with his grumpy and suspicious demeanor and transforming into a more carefree guy. Mackenzie was a natural in Daphne’s role, grasping every side of her personality, including her wit, sass and her caring side. Both were fantastic at performing the roles of the side and secondary characters too, including Clarke with Simon’s British accent. They set the ideal tone for the story, handled the back-and-forth banter and witty dialogue effortlessly, landing the humor naturally and with ease. You could hear how much heart they put into their performance as they conveyed all the characters’ emotions, making you feel them all. It was a pleasure to listen to these two perform, an entertaining performance that is captivating and keeps you glued to the story.