How We Make $2.5K/Month Hosting Virtual Game Nights For Companies

Published: November 24th, 2022
Dennis Hensley
from Los Angeles, CA, USA
started June 2018
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Hello! Who are you and what business did you start?

My name is Dennis Hensley and I’m the co-creator along with Jeb Havens of the boxed party game You Don’t Know My Life! It’s been described as “if Cards Against Humanity and your diary got together and had a baby.”

My background is in entertainment journalism and the questions were developed over my years of interviewing celebrities for magazines like Movieline, Cosmopolitan, Esquire, Glamour, Marie Clair, Premier, Us Weekly, Out, and The Advocate.

When the pandemic hit in 2020, we began hosting Virtual Game Nights via Zoom mostly for friends and in the years since our clientele has become almost exclusively companies that are looking for team-building activities for employees who are working remotely.

Between the two products –boxed game sales and Virtual Game Nights– we bring in about $2,500 a month in revenue.


The idea of having something that was mine, that I controlled, was very appealing.

What's your backstory and how did you come up with the idea?

With the magazine business dying out, I pivoted to podcasting. I launched the podcast Dennis Anyone? with Dennis Hensley, a podcast about “making things up and making things happen.” I love to talk to various creative types about creativity and resilience. At the end of each episode, I have a feature called The Observation Deck where the guest picks a few cards from a deck of questions I developed over my years as a journalist, questions like ‘What kiss from your life felt like something out of a movie?’ or ‘When was a time you felt like a kid in a candy store?’

In 2017, I began to take advantage of the free career programs at The Actors Fund, which offers all kinds of help for people in the entertainment industry, from actors to writers to crew people. While taking an excellent course there called Managing Cashflow for Artists, I started to explore the idea of starting a side hustle of my own.

Writing is such a hit-and-miss business and the idea of having something that was mine, that I controlled, was very appealing. While taking a course at the Actors Fund called Becoming an Entrepreneur, I started a business called Lifecast by Dennis Hensley, where I interview people about their lives, like a podcast, as a way of getting their story down for posterity. I brought the Observation Deck questions into these interviews as well.

The Observation Deck was a big hit both with my podcast and with Lifecast and I started thinking, ‘Maybe there’s a game in these questions.’ Luckily, one of my good friends Jeb Havens happens to be a professional game designer. I pitched the idea to him and we started developing and doing play tests with it right away.

I remember waking up the morning after our first play test and having that feeling like I had fallen in love the night before. I just knew we were onto something. I’ve worked on a lot of different projects over my career as a writer, novels, TV projects, and films…but this one more than any other just felt like a winner from the start.

We continued to fine-tune the game over the next 8 months or so and then in June of 2018, we launched a crowdfunding campaign on our own to have the first batch of 1,000 games made and in our supporter's hands by Christmas 2018.



Take us through the process of designing, prototyping, and manufacturing your first product.

Jeb and I began designing the came components not long after the early playtest. We liked the idea of doodles to illustrate the various things that come up in the questions and we found an artist on Fiver to create the doodles. Jeb did the rest of the graphic design himself with my input.

We found a company out of China called Longpack games to manufacture the games and our experience with them was excellent. I’ll never forget when we got the first proof back to approve. I was expecting a halfway-there version of the game with crop marks and placeholder-type components but what we got was exactly how the finished game would look, complete with shrink-wrapping and everything. It was thrilling.

We gave them a few little notes and then we just waited for the games to arrive while getting as many pre-orders as possible through our crowd-funding campaign. We did the crowd-funding ourselves. We didn’t go with Kickstarter because we didn’t need that much money, just $12,000, and we didn’t have the time to do Kickstarter right if we wanted the games to be here for people by Christmas. So we did our own “underground Kickstarter” and it worked great for us.

Other steps we took during this time were copyrighting the game components and getting a trademark for the game title, which is important. I think our start-up costs were about $12,500, which includes the first batch of 1,000 games, starting our website, hiring the lawyer for the copyright, and various office supplies.


As for the biggest lesson from this period, I think things went pretty smoothly overall. I think one of the riskiest things we did that ended up being the best thing, was committing to getting games in people’s hands by Christmas because it lit a fire under us to make this thing happen.

Without that looming deadline, we might have dawdled.

The games ended up arriving from China about 5 days before Christmas. We had our envelopes all addressed and ready to go and we got them in the mail that day. It was very exciting and we made it by the skin of our teeth.

Another thrilling moment happened on the same day the games arrived. Originally, we had wanted to get the website but it was unavailable so we went with A few months later, I accidentally typed in the web address we originally wanted and discovered that the website URL was coming up for auction. So at the same time, we’re unloading the truck full of games, Jeb is online bidding for the URL and we got it for the whopping sum of $10.



Describe the process of launching the business.

Once we got that original batch of games in and out to all our pre-orders, our next task was to get the game up on Amazon, which Jeb took care of. Then we set about getting folks to review the game on Amazon because that helps attract customers. We ended up getting a lot of great reviews on Amazon. One fun thing we did was take all the text from the Amazon reviews and created a word cloud graphic for our website and social media.


We created our website ourselves on Weebly. Just recently, we hired a consultant for around $800 to maximize the content for SEO and also do some redesigning and streamlining on the site itself. We feel that was a good investment.

In the fall of 2019, we hired a publicist to try and get us into holiday gift guides. They charged $1,500 a month for three months and we feel like it was worth the investment. We got written up in The Star and Parade magazines and were featured in a terrific article in The New York Times about conversation starter games that netted us a bunch of sales. That was very exciting.

As far as lessons, I don’t feel like we made any major mistakes. We’ve just tried to make the most of every yes and not get too hung up on the nos and learn as we go. We still would love to get into stores like Target and Walmart but when the Virtual Game Night concept took off, the boxed game sales took a back seat. But the game is still available on Amazon, chugging away.

Having a business that is YOURS is very empowering. Having this side hustle has taken the pressure off my writing career, which allows me to be more resilient around it. I can keep the dream alive because I don’t need it so desperately.

Since launch, what has worked to attract and retain customers?

The biggest boon to our business happened as a result of the pandemic. We started hosting Virtual Game Nights online, mostly as a way to help people stay connected and to keep ourselves from going stir-crazy.

Jeb designed a web app, which features a game board people watch on Zoom as well as a way for people to enter answers on their phones. The technology and interface are very fun and easy to use and people are impressed by them when they play.

I host the games online like a game show and I have a friend co-host and run the board for me while I emcee. During the pandemic, we were hosting games almost every night. Originally, we had a kind of pay-what-you-can plan where people would pay around $15 per person over Venmo. The first year of the pandemic we probably made $10,000 hosting games and there were virtually no expenses apart from our $15 per month Zoom membership. Plus, the games were just really fun and life-affirming to host.

In early 2021, we partnered with a company called Elevent that books all kinds of virtual events for corporate clients who are looking for team-building events. They’ve kept us pretty busy hosting multiple games a week, sometimes two a day, and because the clients are big global companies, they have budgets for these kinds of events. We can make $360 for a 90-minute game.

Clients can also book through us directly but we find having a middle company like Elevent has helped a lot more clients find us. We’ve also just partnered with a second company called Amphy, out of Tel Aviv. One of the biggest thrills of doing these games is the international aspect. I once hosted a game for Dell computers with players in Singapore, Australia, France, Portugal, Israel, and the UK, all playing at once and having a great time.


As far as advice, getting into the corporate team-building business has been a great boon to our business. For creatives like myself–writers, performers, directors–if there’s a way you can take what you do and create something useful to corporations, there’s money to be made there.

Other things we do for marketing…we have an Instagram account @YDKMLgame and I use Tailwind to plan my posts. I don’t know that it’s had a huge effect on our bottom line but I still do it.

We did Facebook ads for a while but I don’t know how effective they are. One thing I’ve done to promote the show has episodes of my Dennis Anyone? podcast where I play the game with a group of people who have something in common like they’re all in the same show. Those have been fun and we’ve also done a couple of live staged game shows to promote the game where we sold boxed games afterward.

We have an email newsletter through Constant Contact that we send out once a month to past clients. We don’t have a huge email list but people who supported us early on like to hear what’s new with the game and if even one person books a virtual game, that’s $360 in our pocket.


Last year, because of a connection we made through the newsletter, a TV production company signed a deal with us to develop the game as a TV show. We pitched several networks and no one bought but I still believe it can be a great show. That connection would not have happened were it not for the newsletter. I try to remember that when I don’t feel like putting it together.

As for Amazon, it’s the only place we’re selling the game currently and it’s easy. If you tell someone, “It’s available on Amazon,” everyone gets it. Yes, they’re taking over the entire world but for entrepreneurs like us, they’ve made the retail part of our business easy.


When something is all yours, no one can tell you you’re too old, too gay, too fat, or whatever it is…to do the thing. You created it and you call the shots. That is a great feeling I highly recommend it to everyone.

How are you doing today and what does the future look like?

Right now, since both of us have other jobs, our focus is on keeping up with and growing the Virtual Game Night part of our business because it’s much more lucrative than the boxed game sales. We’re also looking to start getting into hosting live events where we come to a company and host a game there on the premises. We did a bit of this before the pandemic and look forward to doing it more now that things are opening up a bit. And the company that we book our virtual games through, Elevent, is starting to book in-person events so we’re going to be exploring that.

And we still believe the game could make a great TV show or podcast so we’ll continue to explore those avenues as well. And I still want to see that baby on the shelves at my local Target.

Through starting the business, have you learned anything particularly helpful or advantageous?

I’ve learned that having a business that is YOURS is very empowering. My career in writing and entertainment has been a rollercoaster and there are so many things that are out of my control. Having this side hustle has taken the pressure off my writing career, which allows me to be more resilient around it. I can keep the dream alive because I don’t need it so desperately.

And when something is all yours, no one can tell you you’re too old, too gay, too fat, or whatever it is…to do the thing. You created it and you call the shots. That is a great feeling I highly recommend it to everyone.

What platform/tools do you use for your business?

I use Tailwind for social media posting. I don’t always understand what I’m doing but I don’t enjoy social media much so I like to just put in a few hours of work a month and then let it go.

I just discovered Canva in the last few months and I love that platform for creating graphics.

Constant Contact is what I use for newsletters and they’re pretty good, though I wish it was cheaper. I love the animated holiday templates they have. They’re fun.

What have been the most influential books, podcasts, or other resources?

The Actors Fund organization was where all of it started.

I also listen to the Side Hustle School podcast, especially when I was first starting to develop the idea. It’s inspiring to hear what other people have made happen.

Advice for other entrepreneurs who want to get started or are just starting out?

Another thing I think about a lot is the phrase, “Done is better than perfect.” Sometimes when we’re creating, we want to find, say, the perfect image for our website, or the best logo ever. We hem and haw because we want something to be just so. It often keeps us from moving forward. Get the stuff done and out there and then make it perfect as you evolve.

But another thing that has surprised me is the good feeling we get sharing the game with people. This game has a way of getting people to open up and connect that’s meaningful and has been such a gift to share. Every time I log off from hosting a virtual game, I’m high from the experience.

Where can we go to learn more?

If you have any questions or comments, drop a comment below!

Dennis Hensley, Founder of YOU DON'T KNOW MY LIFE
Pat Walls,  Founder of Starter Story
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