Look out, Hollywood- there’s a new app on the scene that’s been revolutionizing the entertainment industry!  Special Guest is an app that connects talented performers with people who want to hire them, eliminating the need for an agent and essentially allowing artists to manage their own careers.  The app, co-founded by actor and comedian Damon Wayans Jr. and bestselling author and serial entrepreneur Kris Jones, features musicians, comedians, and even celebrity impersonators, and has been causing quite a stir in the industry.  Recently, I had the opportunity to speak to Kris and ask him a few questions about Special Guest, entrepreneurship and how he makes it all work.

Thanks for chatting with me, Kris!  Did you always know you wanted to be an entrepreneur?
Actually no.  As far back as I can remember I wanted to help people.  My older sister Jennifer went to school for psychology, so by the time I had decided what to study I also selected psychology.  I eventually went on to graduate school to study experimental psychology and then graduated from law school where I studied government law.  Ha! So during the time that I was a professional student, I’m not sure I decided so much that I’d wanted to be an entrepreneur, but instead realized I was becoming an entrepreneur and really liked it.  So it happened when I was in graduate school and it included my brother Rick and I launching a gourmet online food company called pepperjam.com. As they say- the rest is history, as I took that original idea to build a gourmet food company and turned it into a fairly significant digital marketing and technology company, which I later sold to eBay.

How did you end up partnering up with Damon Wayans Jr.?
Damon and I were introduced through a common friend- singer/actress Christina Milian.  At the time Damon was frustrated that many of his friends who were talented struggled to get paid gigs.  When Damon shared his idea it reminded me of another company I founded called “French Girls App” that helped artists get paid gigs (i.e. commission) from people who wanted to get drawn through a digital app.  I took a liking to the idea and after doing research on the problem (it’s incredibly hard for talented people like musicians and comedians to find new paid gigs) I realized that not only was the problem global, but there was no mobile app that was solving the problem at scale.  So we joined forces and founded Special Guest App to make it easier for anyone, anywhere to hire live entertainment.

You appeared on Apple’s Planet of the Apps alongside Damon.  Tell me about that experience.
Being on Planet of the Apps was a really fun and unique experience.  It was an “unscripted” show, which basically means we had very little idea what the experience would be like and only learned (with cameras rolling) as the show went on.  The taping took place over a 6 week period back in late 2016, early 2017. The first day of taping was arguably the most intense, as about 50% of the companies that were cast on the show were sent home.  Fortunately for me and Damon we got selected by Black Eyed Peas founder Will.i.am to his team, which meant we got to stick around and compete for $10M at the end of the show. There were about 10-12 separate tapings where we were asked to do certain things related to the development of Special Guest App.  There were twists and turns and at times we couldn’t make sense of whether or not the producers knew exactly what the “script” was supposed to be.  Working with Damon (and Will.i.am) was a great experience and i’m guessing we did well since we raised $1.5M through being on the TV show.

Special Guest is an app that gives talented performers the opportunity to get paid for doing what they love.  What’s one piece of advice you would give an up-and-coming artist?
Great question!  My recommendation is to put together high-quality materials to showcase your talent.  In my opinion, all talent should have professional headshots and “action” shots done during performances.  Talent can use Special Guest to hire a photographer to come to one of their events to grab the photography.  The other area is professional video. A polished video or two of a performance will significantly help talent buyers that use Special Guest to make a decision to hire a given performer.  Talent can also hire videographers on Special Guest. So once the talent uploads professional photos and videos to Special Guest, they should make sure they are in all of the most relevant categories.  For instance, often a talent buyer will be looking for “impersonators” or “latin dancers.” It’s important that the talent is properly tagged in our system. Talent should also write compelling biographies.  Too often talent will say something like “experienced LA comedian” or something that doesn’t tell a good story. The talent should talk about some of the highlights of their career and some of the experiences they’ve had.  They should come across as experienced and passionate about what they do for a living.

Have you encountered any obstacles while developing the app?
Building a successful app is an iterative process.  The process requires a constant feedback loop with users and also data analysis, which can be very difficult.  One of the most challenging aspects of app development for Special Guest has been serving talent and talent buyers at the same time because the industry has traditionally favored the buyer (i.e. venue) over talent.  So we hope that Special Guest balances out the interests of both sides by making talent more readily accessible and therefore discoverable, while also helping the venue make better buying decisions. We are proud of what we’ve built so far, but there’s still considerable work to do.

What would you say your biggest challenge has been in your career?
Raising capital.  While i’ve been successful in raising millions of dollars in investment capital, the process of raising capital is brutal because investors say no 99% of the time.  That means for every 100 or so “asks” you get 1 to agree to invest. That makes raising capital a lot of work. You have to talk to a lot of investors and each one requires considerable effort to keep interested.  Travel is also required. In general, whenever I raise a round of investment capital I typically allow at least 90 days after all of the preparation is complete. That means for 90 days I go “all-in” with aggressive outreach, follow-ups, travel, more follow-ups, and a push to complete the capital raise.  For Special Guest App we’ve raised about $2M as of February 2019- the entire fundraising process has been exhilarating, but also time-consuming and challenging.  

When you’re not killing it in your entrepreneurial endeavors, what do you like to do for fun?

I love fishing with my kids, spending weekends at my lakehouse, and traveling with family.  I’m incredibly grateful to have a balanced life. One of the things i’m most proud of is that many years ago I placed my family ahead of business, which has allowed me to develop special relationships and experiences with my kiddos.  

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