Dave Green of Mystery Trip: The Power of Flexibility; How I Was Able To Pivot To A New Exciting Opportunity Because Of The Pandemic

Karina Michel Feld
Authority Magazine
Published in
9 min readMay 13, 2021

Finding people that will elevate the company and team is harder and takes longer than it seems. Once you find them though, be loyal, honest, and transparent.

The COVID19 pandemic has disrupted all of our lives. But sometimes disruptions can be times of opportunity. Many people’s livelihoods have been hurt by the pandemic. But some saw this as an opportune time to take their lives in a new direction.

As a part of this series called “How I Was Able To Pivot To A New Exciting Opportunity Because Of The Pandemic”, I had the pleasure of interviewing Dave Green.

Dave Green is the founder and Chief Mysterious Officer of Mystery Trip, a team bonding event planning company that began as an annual summer party he hosted for friends. Looking for more meaning and happiness in his life, Green launched Mystery Trip as a side hustle in 2009, and was able to turn it into a full-time endeavor in 2015. Since then, the company has hosted hundreds of events for companies all over the world including Google, Comcast, YouTube, Facebook, AirBnB, Hulu, Cisco, Netflix, Chevron, Tiffany & Co., Lyft and many more. Mystery Trip can be found at mysterytrip.co.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I was always a curious and independent kid, and I’ve thankfully never outgrown that, as I feel it keeps me exploring the world around me. Throughout my life, I’ve taken several solo road trips purposefully staying off the main roads to discover off-the-beaten-path places and people I’d never meet otherwise. These are some of my favorite times, as driving has always been meditative to me, and helps me get “unstuck.”

I am also what you call a “camp person.” I grew up going to overnight summer camp my whole life, and the bonds and memories I made there have undoubtedly shaped me into who I am today, by showing me how to get along with others with different personalities and backgrounds.

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

My dad had many aphorisms — and never missed an opportunity to share one — but one that has always stood out is “rub it up and keep moving.” I remember hearing him say it often when I’d skin my knee or take a tumble, and would be on the brink of tears. Over the years, I’ve come to practice this philosophy in my life and my work. Things happen — errors in judgment, and mistakes are made…tend to it but don’t dwell on it.

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?

The Fountainhead by Ayn Rand, which taught me to have conviction and trust in only delivering what I feel is our best product possible, which will always yield the highest results for clients and personal satisfaction for me.

The book is the (sometimes incredibly frustrating) story of architect Howard Roark, and how he refuses to bend to the will of the masses, no matter the consequences. I’ve read it multiple times, and have learned a lot from Roark’s integrity to himself and his convictions, even though he suffers personally and professionally for it.

While it’s always tough to turn business away, my experience and dedication to creating the best possible event for a client have led me to do so, as I didn’t feel we could deliver a superior event. Usually, it’s a result of the budget or the amount of time allotted, and I will have a frank conversation with the client to explain. Sometimes they’ll come around and sometimes not, but they always appreciate the candor and our dedication to creating a great experience for them.

Let’s now shift to the main part of our discussion. Can you tell our readers about your career experience before the Pandemic began?

Until the pandemic, the business had been seeing significant year-over-year growth in both revenue and events executed. I had one full-time employee and — depending on the season — four to six contractors running events across the country. We had been steadily expanding into new cities across the United States and had begun discussions on hosting events in both Europe and Central America.

What did you do to pivot as a result of the Pandemic?

By mid-January 2019, I had six groups cancel or postpone events, and that’s when the reality hit me: this was going to be bad. After a few days of moping around coupled with a few sleepless nights, I had a conference call with my team, and we brainstormed ideas for changing the focus of our events to accommodate people stuck at home. While I began a deep dive into video platforms, the team began the discovery phase of ranking our ideations to determine which would work best, as well as search for games that had already been proven.

Can you tell us about the specific “Aha moment” that gave you the idea to start this new path?

I remember it distinctly! I was sitting at my desk, going through old proposals trying to see what could be translated into a virtual event, and came across one from mid-2018 for a client who was planning a hybrid event (who knew?!) and tasked us with creating a trivia game that people both in-person and at home could play. The event ended up being canceled, but I still had my notes from the tests I had done on the various platforms. I immediately got back on these sites and started playing around to see if any would work as a fully at-home experience. Within a few days, I narrowed it down to a winner and had figured out how to jerry-rig their platform to make it work. I ran several test games with my team, friends, and family to smooth it out before marketing it to past clients and my network.

How are things going with this new initiative?

I am eternally grateful and incredibly humbled to say it’s going really well! Since launching Mystery Games in March 2020, we’ve hosted close to 500 events for companies all over the world, and have expanded our offerings to include several games beyond just trivia, including Family Feud, Scattergories, scavenger hunts, and Game of Games (a four-round game comprised of one-round mini-games).

Although we’re charging about 10% of our live events (which has been tough on the bottom line), we’ve been able to connect with and introduce our in-person event to so many more companies, who might not have ever considered us because of pricing or other factors. I’m happy to say we’ve already booked in-person events for Q4 ’21 and into 2022 for clients acquired through virtual events. I’ve seen this time as the ultimate in lead-gen.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There isn’t one person, but several: the clients who believed in us to provide them with a fun, interactive event. This was new for everyone — on both sides of the screen! — and their willingness to take a chance on a new product and experience is something I’ll always remember.

Can you share the most interesting story that happened to you since you started in this new direction?

As an offshoot of the trivia beta testing, I started a free, Thursday Night Trivia game as a thank you to those that helped me get the game up and running. After a few weeks, I started inviting my network to join as well as potential clients I had spoken to who wanted to “test-drive” the game. The game has grown steadily, now averaging about 90 people each week who compete for Amazon gift cards (and a paper crown that gets mailed from winner to winner).

It’s become quite a community — we’ve had two babies born and a wedding! — with people joining from around the world. Every now and then I’ll get an email telling me how much they look forward to the game each week, but there’s one email that I won’t forget for the rest of my life:

I have to tell you that I’m not sure how we found you, but this game has been a lifesaver for my family. It’s just me, my husband, and our son. As with everyone else, the pandemic has made connections so difficult. [Our son] has AD/HD, autism and anxiety, and we don’t have a lot of family or friends because of his behaviors. Being welcomed by your group has been amazing. Thanks to you, your family, friends, and others who play for that. It means a lot. We now measure our week by the trivia game. Like, randomly, one of us will say “Hey, you know what day it is?” and someone else will yell out “Two days until trivia!” Or, in a difficult moment, my husband will look at me and say “Trivia in three days!”

What are your “5 things I wish someone told me before I started leading my organization” and why. Please share a story or example for each.

  1. There is so much more to learn from a bad experience than a good one.
  2. It’s okay to say turn down work if it’s not in your wheelhouse. Don’t try to be everything to everyone.
  3. Starting a bootstrapped business is hard. And lonely. And sometimes scary. But totally worth it.
  4. Not every day will be productive, and that’s okay.
  5. Finding people that will elevate the company and team is harder and takes longer than it seems. Once you find them though, be loyal, honest, and transparent.

So many of us have become anxious from the dramatic jolts of the news cycle. Can you share the strategies that you have used to optimize your mental wellness during this stressful period?

My most effective strategy for maintaining my mental wellness during the last year has been to get outside and away from my computer. I’ve taken several long solo drives over the year, but on a daily basis, I take a long walk (sometimes two) to help clear my head, decompress, and get my blood flowing. I don’t listen to podcasts or music so I can be in the space I’m in. On a good day, these can be like a mini-road trip, as more than once I’ve come home having untangled an issue I had been struggling with, or with a new idea to work on.

I also practice gratitude on a daily basis. While it sounds cliché and perhaps trite, I am often reminding myself that things could be worse for me and my loved ones. And I know — while it may seem like an eternity — the COVID era will eventually end.

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?

A daily Mitzvah. Mitzvah is the Hebrew word for “good deeds, and I think if everyone committed to one act of kindness or compassion for another person each day the world would be a much better place. Something as simple as helping your elderly neighbor bring in her trash cans, or texting a friend who’s been struggling can go a long way.

Is there a person in the world whom you would love to have lunch with, and why? Maybe we can tag them and see what happens!

Chris Cuomo from CNN, as I watch him on a regular basis. I find him to be incredibly insightful about the pressing issues of the day, passionate about justice and fairness, and is always gracious to those with opposing points of view (he also doesn’t mind calling people out on their BS when needed). I’d love to discuss politics, get his views on who the politicians are that are really making a difference, what his workday is like, and hear about Anderson Cooper’s giggling fits…

How can our readers follow you online?

W: Mysterytrip.co

FB: /MysteryTripEvents

IG: /mysterytrip

LI: /mysterytripevents

T: /getmysterious

Thank you so much for sharing these important insights. We wish you continued success and good health!

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