Caroline’s Philly Roots and Digital Dreams: The Overplay Journey

Today’s special guest is Caroline, the COO of Overplay. Many of you may already be familiar with her from her appearance on Shark Tank. We have already covered the Overplay Shark Tank update separately, so you can check that out.

Recently, I contacted her for a short email interview. I’m happy to say that she was very responsive and answered my questions. I appreciate her for taking the time to provide such thoughtful responses. I hope this short interview will prove to be helpful for our audience. This conversation is a great chance for us to learn more about her journey and get some valuable advice from her experiences.

Introduction and Background

Sara: Please tell me about yourself, your background, education, experience, and position in the company.

Caroline: I’m very Philly! I was born and raised in Philadelphia, so I am very much a city kid. I’m also a first generation American. I went to the University of Pennsylvania for undergrad and then back to The Wharton School for my MBA. In the middle of those, I was an investment banker who worked in Equity Capital Markets and took companies public. After MBA, I went to work at Sesame Workshop, the creators behind Sesame Street and other children’s educational programming, where I ran digital media business development. That is where I met my co-founder, Dan Projansky when he was running interactive production. Together, we made great cutting-edge product together, including Sesame’s very first apps, console games, AR/VR products, and more. I also did all of the streaming deals with the likes of Netflix, YouTube, Hulu and others. Dan and I are co-founders together for Overplay and I’m also the COO.    

Pre-Shark Tank Preparation

Sara: Can you describe the journey and preparation that led up to your pitch on Shark Tank?

Caroline: We were actually approached by Shark Tank to be on the show. So we replied to the email, did the interviews and then found out that we were chosen! It was truly amazing and happened so quickly. We prepped the pitch the entire summer. Because we are a software/app company that has some pretty complicated technology behind it, we had to make the pitch for Overplay super simple yet entertaining so that the audience would “get” what we were showing. We decided to go with a simple 90 second pitch, show the app and how easy it was to make a game, and then, to really hit the pitch out of the ballpark, we invited Mark Cuban and Mr. Wonderful to compete head-to-head to play 5 mini-games made from each of the Sharks’ social media posts. We knew they would understand how powerful our technology when they played their own content in a game! And it worked!!

Valuation and Strategy

Sara: How did you decide on the valuation you presented to the sharks, and what was the strategy behind your initial ask?

Caroline: It was pretty simple for us, actually. We had recently raised a pre-seed and just priced it at the valuation of the pre-seed. Through that, we knew the exact upper-bound of what we were willing to accept.

Post-Shark Tank Impact

Sara: What happened to your company after appearing on Shark Tank in terms of investments and business growth?

Caroline: Being on Shark Tank really accelerated our product development because we had to have an early beta ready for airing with thousands and thousands of downloads of our app. We launched our Seed round of funding, including an equity crowdfunding Wefunder, at the same time as our Shark Tank airing on March 15th. Upon airing our downloads went up by 2000%! We were also able to quickly raise $500K via Wefunder. An amazing coincidence is that we were chosen as Finalists for the Innovation Awards for SXSW, so we were actually at SXSW when our Shark Tank episode aired. Mark Cuban actually came to visit us at our booth at SXSW!! (See picture attached.There has been so much excitement around what we’re building — I’ve been on morning shows and invited to speak at sold-out events. I think a lot of people are finding our story and product inspiring!

Current Valuation

Sara: What is your company’s net worth today?

Caroline: We are currently raising on a $50M post-money cap, so I guess you can look at that as our current valuation.

Additional Investments

Sara: Have you secured any investments from other investors since your appearance on Shark Tank?

Caroline: Yes! We currently have a Wefunder open https://wefunder.com/overplay/ and over 825 people have already investment in this new round of funding. We’re approaching $1M raised on the Wefunder! We are currently having advanced conversations with institutional investors and VCs.

Business Strategy Evolution

Sara: How has your business strategy or operations changed after your appearance on Shark Tank?

Caroline: Operations-wise, we’ve nearly doubled in size to about 20 people. Strategically, while we are still focused on B2C, we are also working on building out the technology so that other apps and websites can incorporate Overplay — this is our B2B SaaS model.

Challenges

Sara: What were the biggest challenges you’ve faced since your appearance on Shark Tank, and how have you addressed them?

Caroline: The fundraising environment is not the best right now, but it is improving. We are so thrilled that we are raising both institutional and retail investment at the moment, so that we can continue to raise and build.

Long-term Objectives and Influence

Sara: What are the long-term goals for your company, and how has Shark Tank influenced these goals?

Caroline: Our long term goal is for Overplay to be ubiquitous — where any video can now be interactive. Our being on Shark Tank has opened doors for partnerships with large creators and media companies, and made conversations go much more quickly. Mark Cuban and his team have also been great advisors to us on this front.  

Advice for Future Contestants

Sara: What advice would you give future entrepreneurs considering applying for Shark Tank?

Caroline: Absolutely DO IT! It’s truly one of the best experiences I’ve ever had in my life!!