Successfully Pivoting From Surprise Event Planning To B2B Events And Corporate Gifting

Published: May 16th, 2021
Shane Kovalsky
Founder, Mystery
from Seattle, WA, USA
started February 2019
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Note: This business is no longer running. It was started in 2019 and ended in 2023. Reason for closure: acquired by Glue.

Hello! Who are you and what business did you start?

Hey! I’m Shane Kovalsky, Co-Founder of Mystery, an experiences platform that brings surprise and delight to the workplace.

WTF does that mean? Well, right now it means B2B virtual events and corporate gifting. The catch is that—outside of the organizers—users don’t know what they’re getting into until it happens. And people love it: We’ve engaged with more than 20,000 users in just over 2 years.


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

The short story is I was bored and burnt out.

I started leaving Seattle on a “first flight out” to switch things up. One weekend everything fell into place—it was like a movie. I went to Austin, it was ACL, I ran into friends. The whole weekend just worked out perfectly and I thought, what if I could do this for someone else? How do I recreate a spontaneous, surprise experience that hits every single nail on the head? And Mystery was born.

Who you partner with in general is everything. From our earliest investors, the friends who helped get things off the ground, and to the kickass team I have today, every ounce of Mystery's success lies in the people who make it happen.

It’s probably worth mentioning, I had previous startup experience working at Porch and Convoy. I’d see successful tech companies take off from early stages—that combined with the entrepreneurial itch I’ve always had made leaving my stable career behind to pursue Mystery a lot easier.

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

Scaling back my magical weekend in Austin a bit, I started planning surprise nights out on the town for friends and family. People were really into it. I knew I had customer love and a compelling business model.

The trick to Mystery's first product—then called “a Mystery,” now called a “Night Out”—was nailing the formula for the perfect outing, and there were a lot of variables: Price, interactions with other people, knowing what someone was/wasn’t into, transportation, number of stops. Seriously, the list goes on and on.

A Night Out was (is? Stay tuned) 1–4 stops. It could be anything from a fencing class to dinner and a show followed by cocktails. And pretty much everything in between. While it was for anyone (families, friends, coworkers, large groups, individuals), most of our customers were couples. We even partnered with the world-renowned Gottman Institute and created a series of date nights based on conversations they recommend couples have. We lost track of how often we heard things like, “We’ve been married for 20 years, and this felt like our first date all over again.”

Describe the process of launching the business.

I think there are two ways to build a business:

  1. Strategize, make it perfect, launch.

  2. Find something you’re passionate about that people want, and build it as you go.

If it isn’t obvious by now, I’m an Option 2 guy.

The official launch was Valentine’s Weekend 2019. I had onboarded some friends and business partners in the previous weeks (persuading them with my homemade, extremely manual date night planning), and using word of mouth, we beta launched with dozens of dates.

Fun fact (in case you’re either not in Seattle or can’t remember that far back): Seattle had a snowpocalypse on Valentine’s Weekend 2019.

Photo from KOMO News

Photo from KOMO News

Needless to say, there was a lot of “building as we went” from day one. Lessons like: Don’t put your personal savings on the line for reservations when you don’t have a snowpocalypse cancellation policy in writing. Ya know, just little things.

My biggest learning from launch (which still holds today) is that who you hire is everything. Who you partner with in general, is everything. From our earliest investors, the friends who helped get things off the ground, and to the kickass team I have today, every ounce of Mystery's success lies in the people who make it happen.

embed:vimeo Things went really well with Night Out, people really loved it. We even made a really cool commercial!

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

Because we’ve focused so much on a product to make people happier, it’s been pretty easy to recognize the product fit. When it’s working, you know. When it’s not working… oh yeah, we know that too. That customer love and the inevitable word of mouth that comes with it is what has fueled our growth.

Beyond banking on people talking about us to their friends, we’ve tried all the other marketing strategies too: From social media ads to press outreach, even posters on light poles around the city (I like to think I brought QR codes back before the pandemic made them cool again).


Photo courtesy of our marketing lead who thankfully has improved upon our efforts since I made this great move

Levers which have worked well for us (though at different times and not entirely reliably) have been press (not to beat a dead horse, but when people love what you do, it’s easier to get the media to talk to you); email marketing is another one we love—more lift upfront but way less to keep it going.

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

Today we’ve successfully found product-market fit for the third time—thank you 2020. Remember that kickass team I mentioned earlier? They turned a whole lot of lemons into some amazing ways to continue bringing people surprise & delight during a year no one could have ever expected.

Because we’ve focused so much on a product to make people happier, it’s been pretty easy to recognize the product fit. When it’s working, you know. When it’s not working… oh yeah, we know that too.

First, this was an at-home version of our Night Out [on the town]. In a week my team reached out to new and existing partners to create a box full of activities and treats, paired with dinner, all delivered to your door, and all supporting small local businesses. We launched Night In at the end of March, meaning we saw a problem and acted extremely quickly. And customers loved it.


Night In has helped us give $500k+ to small businesses, expand nationwide, and deliver surprise & delight during a pandemic

Like anyone else, our team went fully remote and then had to decide and re-decide and re-decide again what our flexible environment would look like long term. One of the most important factors was maintaining the culture we’d worked so hard to establish. Our small team was growing, how would we make new members feel like part of the crew and how would we keep morale high without all those after-work cocktails and in-office shenanigans. We obviously were alone here and we knew we had what it would take to bridge that hybrid work ”place” gap for not only ourselves but for others.

With that, our latest product launched in Fall 2020, Virtual Events and Corporate Gifting. Tapping into our planning expertise and network of vendors, we now bring surprise & delight to the workplace by way of virtual events and corporate gifting. The cherry on top is using technology to measure employee engagement and team morale for enterprise clients.

I don’t want to sound like a jerk and say it was easy to switch gears to B2B, but honestly, my team was excited about the challenge and we all believed the product wasn’t entirely different from what we’d been doing: We were still using technology to connect people and make them happier. The rest was just grabbing other tools from our belts. We beta tested with friends and former peers and then word of mouth did a lot of the work for us. Back to beating that dead horse, people loved it so that helped a lot.

Virtual Events and Corporate Gifting have helped us bring our mission of surprise & delight to remote work environments

In general, we’re growing aggressively: 30% month over month for the foreseeable future; we’re multiplying our team, and we’re adding more and more of the best companies in the world to our client list daily. So that‘s cool.

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

  • I’d be failing if I weren’t always learning. But, some things that come to mind…
  • Don’t go for big partnerships early—it’s a waste of time.
  • Survive to thrive is very real.
  • Capitalize on uncertainty.
  • Work backward from a customer experience.
  • “Ready, fire, aim” is one of my favorite phrases.

What platform/tools do you use for your business?

We’re a tech company so we use a lot of techs. What we’re lovin’ right now:

  • Webflow. It’s a little trickier than some platforms, but it strikes the right balance for us between usability and the ability to do cool shit.
  • Twilio.
  • Metabase. We’re a data-driven company; Metabase is the fastest and easiest way for us to keep that data organized.
  • FullStory. Just one way of identifying our sticky spots and providing a frictionless experience for our users.
  • Figma. We’ve found that Figma is the perfect intersection for all of our teams to collaborate creatively without needing to learn everyone else’s preferred tool.

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

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

I feel like the real “founder success story” often takes a while to come out. You hear a lot of these Cinderella stories and they’re inspiring until you figure out that you don’t necessarily get a Fairy Godmother. That part is you down in the dirt lifting yourself out of it (or surrounding yourself with the right people who will).

The highs and lows are real, you just have to optimize for happiness.

Are you looking to hire for certain positions right now?

YES! Our team is growing, growing, growing. We are more or less hiring for full-time positions across the company. Honestly, by the time this goes live, the exact positions will have shifted, but please check out our careers page and let us know if we need you on our team.

Where can we go to learn more?

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