Andrew Playford At Kaption Has Got Something Funny For Your iDevice

Kaption is an iOS game that turns the joy of The New Yorker’s weekly caption contest into a game of wit among you and your friends. What’s the hilarious difference? You’re captioning the everyday photos you shoot and using them as the contest material. As the battle continues, other users get to vote on which caption’s best and a champion emerges. Get your caption on because if you can’t hang, you’ll achieve immortality at your expense.



The roots of Kaption were sowed in New York where Andrew Playford and Barry Kaplan worked together in the startup world. Barry made a professional connection with Paul Malelepsy while working at Groupee and today the three make up the Kaption team.


As the team was working on a language-learning app, the essence of Kaption was born. Essentially, they had a similar function in that app in which a user would snap a photo and then ask the user group for the best translation, which was voted on. This resulted in the team building although it wasn’t clear to them how to monetize the site. With this in mind, they decided to make it game from here the leap to Kaption was made.



Kaptions’s Andrew Playford took some time to speak with Killerstartups and here’s what he shared with us:


So how’d you come up with the name for your Kaption?

I just made it up and the others just said “cool!” It took 5 seconds!


What’s the very first thing you do at work?

I check my email before my feet hit the ground. Usually on my iPhone.


How many people did you start Kaption with and how many people work for you now?

I started it first and then found the Barry and Paul were itching to do something new so I brought them on as co-founders.


Remember the early days starting up? Maybe you can share one anecdote that describes the struggle you went through?

We are still going through the struggle! We are in the gaming business. We need our first game to be a hit!


How do you handle frustration?

I tend to get quiet, then I will go hit the rowing machine for 30 minutes, that usually sorts me out!


What’s your office environment like?

We all work out of our own apartments or in coffee shops. We always take our laptops wherever we go. Barry and Paul (the engineers) love working late, really late so I have gotten used to working really late too but my start in the morning is now also getting later.


How do you picture your company in 5 years?

We’d love to have a whole suite of awesome games and a studio of 20 to 30 awesomely talented game developers!



Who or what inspires you?!

I get super excited just seeing the crazy opportunities around us all the time. With the explosion of mobile and apps and the dramatic reduction in cost to create stuff is just so awesome!  My motto is Just Do It! I borrowed it from Nike. I think you just gotta be in the game to get lucky.


How’d you fund Kaption?

I funded it from money I made from my fist startup, but now I’m hurt’n!


Got any great bootstrapping tips for the lean startups out there?

Yes – Don’t do anything which does not have a revenue model from day 1. Instagram is a terrible example to all young budding entrepreneurs. That won’t happen again for a decade!


What would you be doing if you had one year off and $500,000 to spend?

I’d buy an awesome apartment and spend it all on renovations. Super modern with industrial materials.


Do you consider yourself a successful entrepreneur right now?

No – not yet – I need to hit a big one – an exit of $25 million or more would get me into the ballpark.


Name a site you couldn’t live without.

Airbnb has been keeping a roof over my head for the last 6 months!


Name a mobile App you’re in love with and why?

Tripit – awesome for travel – no more digging around for the email itinery!



Dogs or cats Mr. Playford?

Dogs – I understand them better and they stick around – loyalty is big for me!


iOS or Android?

IOS for now as that is what our app is in but we will move it to Android to. Paul is our Android lover, Barry is the Apple fanboy!


What’s the greatest thing about Kaption?

We love playing Kaption it! its not super easy but if you think about each caption and play people you know its awesome fun!


Where can our readers get ahold of you?

Twitter: @kaption-it

Facebook: and


What do you wish we had asked you?

How much does luck play in becoming an entrepreneurial success? I think luck is 50%. But you have to be playing to get lucky!


Photo Credits / Kaption