Everything's Coming Up Rosy Khalife - Founder of Surprise Ride


women in business, coaching, entrepreneurship, Shark Tank
Rosy is so inspiring!

We met Rosy Khalife, who founded the company Surprise Ride with her sister Donna Khalife, at the Inc. Women's Summit a few years ago. We were so inspired by her energy and the success of Surprise Ride, plus hey - the sister connection - that we went to Surprise Ride Headquarters in D.C. to play a personalized board game with the Khalife sisters. Since then, Rosy and Donna have been mentors for us so today we wanted to talk to Rosy a little bit more about her journey.



Sister Founders, Women in Business, Family business. women supporting women
Sisters unite!

Bundle Sisters: We met you at the Inc. Women's Summit and were so inspired by the work you were doing with your sister, Donna with Surprise Ride. What made you take the leap into starting a company with your sister?


Rosy: We didn’t set out to start a company together! We explored our ideas via a shared Google Doc. We lived on different time zones and every morning we’d wake up to new notes from the other. The ideas starting flowing and it came together organically. I’m all about things coming together with ease. This was one of them! And Donna and I work really well together. We love and care about each other so deeply, which keeps us rooted in what really matters. Even when things get nuts in business or life we stay grounded in our love for one another. If you’re thinking of starting a company with a sibling or a friend and it feels right, then I say go for it!



shopping, kids activities, non screen activities for kids, screen free
Surprise Ride in stores!

Bundle Sisters: What was it like being on Shark Tank? Are you intimidated by Mr. Wonderful after working with him?


Rosy: Being on Shark Tank was a crazy life-changing experience! Hundreds of hours went into prepping but it was all worth it. It’s definitely a mentally taxing experience because you don’t know if you’ll actually air until you are literally watching yourself on TV. Every step of the way you have to believe it will happen and have faith.


Kevin O’Leary has been an incredible business partner. He is accessible, extremely intelligent, and kind. He hosts a Mr. Wonderful Summit every year in Miami and all his portfolio companies come together. It’s a few days of connecting and learning together which is really powerful. And drinking his delicious O’Leary wine!



Shark Tank, success, sisters
Swimming in the Shark Tank!

Bundle Sisters: What was it like when Surprise Ride got acquired by Fat Brain Toys? (Huge congrats by the way!)


We're so grateful that the baby we created could go on to do great things! Fat Brain Toys has continued our mission of giving kids a break from electronics. Getting acquired is a moment ever entrepreneur dreams of and I’m grateful to have experienced it. The team at Fat Brain Toys is family-friendly and committed to making an impact in the lives of kids. IT was important for us to find a home for Surprise Ride where it could thrive and be loved.


Bundle Sisters: You have been a mentor of ours for years; but we have recently started coaching with you and it's been transformational - you have such a gift! What made you decide to officially start up your coaching business? What do you love most about it?


Rosy: Thank you ladies! That’s very sweet of you. I have loved watching your company grow and being part of it! I learned the value of having a coach when Donna and I started working with our business coach, Dale Larson of Startup Happiness. I also worked individually with Hayley Carr. Both are phenomenal and helped shift my mindset. I believe every entrepreneur needs a business coach in their corner. I’ve been coaching and advising entrepreneurs for over 7 years mostly as favors to folks that email me. I’ve started offering more sessions now through my website. I try to make it easy for busy entrepreneurs and offer one-time or monthly sessions. I also offer Pay What You Can sessions so that anyone can do this regardless of their financial situation.


My approach to coaching brings together my own experience of growing my company to millions in sales. I am big on advising from a place of authenticity. My favorite moments are when I have a call with an entrepreneur and hear they’ve increased their sales or landed a partnership since our last chat.



Bundle Sisters: What inspires you?


Rosy: I try to find inspiration all around me. We all have moments when it's hard to find the joy but I believe if we try, we always can. The simplest things inspire me. When the sun shines. Kids playing together. Smiling at a stranger. A good song that makes me sing. Cutting into an orange and seeing its colorful flesh.





Let's Bundle!


1.) Curiosity,

2.) Kindness

3.) Solution-oriented

4.) Open-minded





Too many come to mind! We were filming a live TV segment on a morning talk show and were standing behind a table filled with our Surprise Ride products. I'm a hand talker so as I was answering a question from the host I knocked down a little easel from the table! Luckily, with the magic of live TV there's a 3 second lag so they were able to switch to another camera! It was as though nothing happened. :)





Running a business can feel like a roller coaster at times. The highs are so exciting and the lows can feel really draining. Place your hand on your heart and take a deep breath. At the end of the day all that matters is YOU. Prioritize your mental well-being above all else. Take a day off or even an hour off. The world will not explode. It’s also so important to learn how to ask for help. Don’t get stuck alone. Call a friend. Send me a message. If you’re anything like me I have a hard time asking for help. But every time, it’s been a game-changer. You got this.



The entrepreneurial journey can be exciting, frustrating, exhausting, joyful, isolating, and community building all at the same time. It is so important to find people you can connect with and we are so grateful that we have Rosy in our corner.


To learn more about Rosy or book a coaching session with her (truly life changing!) click here. As always, if you want to Bundle with us, you can get your game here and we will learn all about you through our Bundle Blueprint. Leave a comment below of your favorite toy from when you were growing up!