Community//

Mike Wills of Paint and Sip LIVE: “Quick Thinking”

Quick Thinking. Just as with an in-person event, something can go wrong during a virtual event. Whether it’s a technical glitch or otherwise. The event leader must be someone who reacts swiftly to fix a problem to reduce disruption to the event. During one such scenario we leaned on the DJ to engage more with […]

The Thrive Global Community welcomes voices from many spheres on our open platform. We publish pieces as written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Community stories are not commissioned by our editorial team and must meet our guidelines prior to being published.

Quick Thinking. Just as with an in-person event, something can go wrong during a virtual event. Whether it’s a technical glitch or otherwise. The event leader must be someone who reacts swiftly to fix a problem to reduce disruption to the event. During one such scenario we leaned on the DJ to engage more with the attendees and it worked to redirect focus from the issue and saved the event.


As a part of our series about “5 Things You Need To Know To Successfully Run a Live Virtual Event”, I had the pleasure of interviewing Mike Wills, Jr., CEO of Paint and Sip LIVE.

Mike Wills, Jr. is an entrepreneur, finding success in leveraging both evolving technologies and societal shifts. Wills is currently the CEO of Paint and Sip LIVE, the premier paint and sip company that features live DJs and theme nights. Prior to taking the helm at the arts and entertainment startup, he co-founded Maid Marines in 2012. He followed that up with the purchase of Check Maid a year and a half later and acquired Synergy Maids in 2014. The New York-based cleaning services grew to earn over 3 million dollars per year in revenue. In 2017, Wills co-founded Credit Glory, a credit repair business that saw lightning-fast growth when revenue rose 500 percent in four months.

A native New Yorker, Wills studied business and technology management at Polytechnic Institute of NYU. It was an ideal landing spot as he spent his youth flipping through the pages of Black Enterprise and Forbes. Now in his 30s, Wills’ enterprising efforts elevate his businesses to the next level. And he doesn’t keep his achievement blueprints to himself, as he often gives business advice to friends and strangers alike when called upon.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a bit about your “childhood backstory”? Can you tell us the story of what led you to this particular career path?

I grew up seeing entrepreneurism in my family. My dad ran a limousine business so the thought of running my own business was realistic. I always knew that I didn’t want to work for anyone other than myself.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I had a social network back in the day, JuniorU.com. It was like Facebook meets Blackboard for elementary to high school students, their parents and teachers. With Junior U we tried to do too much too soon and were too focused on every little feature. We’d get bogged down in trying to offer too many services and it prevented us from taking off. I learned that I should have focused on one feature and doubled down on that instead of having a million different features.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

Definitely Black Enterprise magazine. My grandmother gifted me a subscription when I was young and I remember being very engrossed in all of the stories.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Never be comfortable. I’m not sure that’s an official “life lesson quote” per se. It’s a phrase I hold close, though, because it’s been a great source of motivation for me. There is always going to be a new company in your space looking to take your spot. So never get comfortable. Always push yourself if you want your business to flourish and remain competitive.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. For the benefit of our readers, can you tell us a bit about your experience organizing events in general?

In general, my experience as an event organizer all stems from the events and parties I throw for my family. Barbeques, birthday parties, etc., that are multi-generational and involve a lot of logistics, from food, to entertainment, and more.

Can you tell us a bit about your experience organizing live virtual events? Can you share any interesting stories about them?

Our company, Paint and Sip LIVE, is a business created for the virtual platform. We host painting classes with live DJs and instructors guiding participants step-by-step. Each month we spotlight featured events open to anyone to join. We also host private parties, with clients ranging from global corporations to Mary down the street throwing a fun birthday party for her friend. They are lively, they feel as close to an in-person party as possible, and they are fun, which is the point.

In your opinion, what is an example of a company that has done a fantastic job creating live virtual events? What specifically impresses you? What can one do to replicate that?

There are a few but top of mind are some of the events hosted by theatre companies, which have had to move completely to virtual performance. They’ve figured out some of the basic, but not always simple to execute, rules to a good virtual event. The sound and visual have to be of the highest quality and the event has to be well planned. It’ll be obvious to those attending or involved if the virtual event was not thoroughly planned or thought out.

What are the common mistakes you have seen people make when they try to run a live virtual event? What can be done to avoid those errors?

Not making sure that everyone is having a good time. On the other hand, doing too much to make sure everyone is having a good time. You have to understand that there are introverts and extroverts in every crowd. Making some people talk or dance when they’d rather enjoy with their camera and microphone off can ruin their experience. A good host has to read the crowd and know who to spotlight and who to leave alone.

Which virtual platform have you found to be most effective to be able to bring everyone together virtually?

We use Zoom for our Paint and Sip LIVE parties. It is easy for our clients to navigate and the video and sound quality are great.

Are there any essential tools or software that you think an event organizer needs to know about?

Zoom is the primary app that comes to mind.

Ok. Thank you for all that. Here is the main question of our discussion. An in-person event can have a certain electric energy. How do you create an engaging and memorable event when everyone is separated and in their own homes? What are the “Five Things You Need To Know To Successfully Run a Live Virtual Event” and why? (Please share a story or example for each.)

  1. Engagement. At our Paint and Sip LIVE events, people can unmute themselves at any time to talk, tell jokes and engage in general banter with the instructor, DJ and other participants. Your participants have to be able to do just that, participate, in order to stay engaged. Our instructors also encourage participants to feel more socially involved by initiating conversation and building rapport.
  2. Entertainment. Paint and Sip LIVE was created to entertain people during the pandemic. At the start, the only obstacle was convincing people that a virtual event can be just as fun as an in-person event. We’ve done a good job of that by leveraging popular acts and DJs to entertain people and create a party atmosphere.
  3. Quick Thinking. Just as with an in-person event, something can go wrong during a virtual event. Whether it’s a technical glitch or otherwise. The event leader must be someone who reacts swiftly to fix a problem to reduce disruption to the event. During one such scenario, we leaned on the DJ to engage more with the attendees and it worked to redirect focus from the issue and saved the event.
  4. Smooth Execution. Whichever virtual platform you choose to use, it must tick all your boxes for audio and visual quality and ease of troubleshooting. Repeated glitches, poor sound, etc., will only reflect poorly on the event. And it’ll be memorable but in the worst way.
  5. Action. Back to participation, which is key to evoking that air of an in-person gathering. With Paint and Sip LIVE, the action is painting, everyone does it at each event. The ones who are not shy get up and dance, and we love to see people having a great time. To create a successful live virtual event, you never want attendees to feel not involved in what’s going on. They must be invested to feel that they are receiving value from the event.

Let’s imagine that someone reading this interview has an idea for a live virtual event that they would like to develop. What are the first few steps that you would recommend that they take?

Just start! There are enough courses, forums and videos that will help you every step of the way. Every question you have has been answered time and time again. If you have a business idea and there’s a remote option for it, just launch it.

Super. We are nearly done. Here are our final questions. You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

I would definitely create a movement in which we are teaching young people the value of creating wealth. Such as actionable steps to create your own business, or how to make the money you’re earning at your 9–5 work for you. I am still learning how to do this. We weren’t taught any of this growing up.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

I’ve always admired Diddy, 50 Cent, and Jay-Z. They all grew up in New York like me, and the way I’ve seen them use one industry to propel themselves into other industries has always amazed me. It’s hard enough to succeed in one industry, but to do it time and time again is incredible.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...

woman in white long sleeve shirt sitting on chair
Community//

Remote Working: How Businesses Shift Virtual to Host Lively Office Holiday Parties

by Nicole F.
Community//

“Stay your course.” With Charlie Katz & Joe Lewis

by Charlie Katz
Community//

Chris Wickson of Integrate: “Picking the right event tech ”

by Tyler Gallagher
We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.