Skip to page content

Surprise Ride's Rosy Khalife On Life After Shark Tank



Rosy Khalife is just one half of the dynamic duo surprising the D.C. community. Along with her older sister Donna, Rosy Khalife co-founded the D.C.-based Surprise Ride, a subscription-based service that sends a new themed box to families each month with toys and engaging activities for children. Think of it like a Birchbox for children's activities, and the goal is to get kids away from their devices and engage them in creative thought.

Chances are, you've heard of Surprise Ride. In 2013, they were on ABC's Shark Tank. They had an investment offer, but ultimately turned it down, which is why earlier this year the two sisters appeared on the follow-up show Beyond the Tank. That's where the company made history: Shark Tank's Kevin O'Leary stopped by the Surprise Ride offices and made an investment, marking the first time a shark has ever circled back and made an investment in a company after an episode.

Six months later, Rosy says the company is eager to expand. They're working on an appearance on QVC and on children's app slated to drop soon.

You two are sibling who started a business together. So I'm curious to know how that dynamic plays out in the business? 

We get that question all the time, and it's such a good one because it is hard. We're four kids in our family, and I don't think I could have started a company with any of the other two.

So me and Donna, we work really well together. We have a great relationship. It's actually nice really working with her and her being my sibling. You can really cut through the BS. We don't have to tip-toe around each other's feelings or feel like we're overstepping or any other thing you often hear from founder relationships. You know, when it's the two founders who started it together from the get-go, there can be some sort of dynamic issues. But we never have anything like that. We can be very honest with each other.

It's actually nice really working with her and her being my sibling. You can really cut through the BS.

I know that it's been about six or seven months since you all accepted an investment from Kevin O'Leary, and he is also integrated into your company in a way. How has that partnership fleshed out now that it's been a few months? 

It's been going really great. He's very responsive. If you email him or text him or anything, he will get back to you in less than an hour. And it's just every time, it's so mind boggling to me. This person who literally has a million things going on — he's invested in a bunch of companies, is on TV every other day, and still finds the time to just be so responsive. It's just really really awesome.

We are working with him on going on QVC, which we're really excited about. He does a show on QVC where he shows these wines and stuff, and so we're working with him on having Surprise Ride go on QVC, which I think will be really awesome.

We're also going to the UN in November. It's Women Entrepreneurship Month, and the UN will be hosting and event for women and he will actually be speaking at the event. He's a huge advocate of women entrepreneurs, so he's going to the UN to talk about how his women portfolio companies have outperformed his male companies.

So how has your company grown since the investment and also since going on Shark Tank a few years ago? 

I think it's helped us in a bunch of way. People watched our story on Shark Tank, and they really got to know us in a very personal way, and I think that's continued to help us move forward. We get emails from customers just addressing them to Donna and me — obviously, we've grown the team, and we have a customer service team, and what not. But people are still just wanting to talk to us and feel a real great connection, and I think we continue to try and foster that in our emails to them.

So I think it gave people the ability to know who we are, and that really helped because when you create a product for families and kids, you really want to trust the company that you're using. Companies are so big these days, and you don't really know who's behind them, and so I think people knowing who we are has really helped.

We want to be wherever kids are, and we know that they are on the screens a lot.

With that, where do you plan to take the company in the future? 

We're actually working on an app for kids. This might seem counterintuitive to what I just said about getting kids off of the gadgets, but this app is really cool. What it does is you get on the app and you're at home and it prompts you to grab things around you. So games that you have around the house, activities and things that you have around the house, and it gets kids to use tech to facilitate real-world activities.

So rather than you logging onto this app, and you get sucked into this vortex of this world, like Minecraft or all these other apps that get kids to do things on the iPad, this app is actually going to be one that gets you to do things in the real world.

We want to be wherever kids are, and we know that they are on the screens a lot, and we want to get them off the screens as possible. But for the times when they're actually on the iPad, we want to be there as well, and we want to make sure that they're doing something fruitful.

We really want to get this out. We're aiming for the next couple of months.

I feel like you all are a startup and a technology company, yet the original product — not the upcoming app — is kind of the antithesis of technology. How does that juxtaposition play out there? 

We are very much an e-commerce tech company, and everything about us is your classic kind of e-commerce, tech play. And then we have this product that is very much hands-on and off of the gadgets. For one thing, it makes what we're offering interesting to people.

And I hear you, I've thought about it a few times, but that's just how people buy things these days. We considered going into to retail and what not, but for us, it delivers the best possible experience to kids and moms and families, in general.

What makes innovation in D.C. unique? 

The community is not as big as other cities. We get the question all the time "Why are you not in New York? Why are you not in San Francisco? Or even in Boston?" and we really love being in D.C. for a number of reasons, and one of them is that the community is really willing to help and wants entrepreneurs to succeed and do well.

As it relates to innovation, I think a lot of people here have awesome ideas that they're working on, and what makes it really beautiful is that people want to help and there's definitely a sense of community. Rather than, you go to a lot of tech places — like you're San Francisco or your New York — and it's just less of a focus on helping each other and succeeding.

Is there anything you would change or ways in which you want to see the tech community grow?

The mayor of D.C. and the D.C. government is continuing to help startups, and as long as they're continuing to help startups and entrepreneurs succeed, we will continue to succeed. Their help has been really helpful — they have grant options for people, they have subsidized places for offices, and a lot of those things are things that people don't know about. So anytime I talk to entrepreneurs, I try to tell them about all of the resources that are available as a D.C. entrepreneur.

People should just go for it, really. You have nothing to lose.

So on that note, what advice do you have for entrepreneurs? 

Being an entrepreneur is really exciting and has a lot of awesome things that come along with it. You get to make your own decisions. You get to see your vision come to life. So my advice is for someone, if they have something that they want to start, they really should just take the plunge and go for it. Nothing is going to get started if you don't start. Nothing is going to succeed if you don't start.

I hear from a lot of entrepreneurs "I'm not sure what the traction will be," "I'm not sure what the response will be," "I'm not sure if a lot of people will watch the video I put out," or whatever. And I just say "You didn't even do anything yet. You didn't even start it, how do you know?" I think people should just go for it really — you have nothing to lose. You can always try something else, you can always change your idea.


Keep Digging

MG 0760Polo
Profiles
Soo Jeon Headshot (1)
Profiles
Jeff Berkowitz
Profiles
Damon Griggs Headshot July 2022 close up
Profiles
julio
Profiles

Want to stay ahead of who & what is next? Sent twice-a-week, the Beat is your definitive look at Washington, D.C.’s innovation economy, offering news, analysis & more on the people, companies & ideas driving your region forward.

Sign Up