Brennan Keough, Founding Team Member of Mystery
1. What were you doing before you quit your job?
I was working in Boeing Commercial Airplanes Strategy & Market Development (aka Corporate Strategy and M&A) group.
Prior to joining Strategy & Market Development, I held roles at Boeing in Financial Operations, International Procurement, and Boeing’s VC group, HorizonX.
2. When did you realize you wanted to quit your job?
I always had the entrepreneurial itch and after two years at Boeing, I knew it was time to venture out. While at Boeing, I spent six months trying to figure out exactly where I wanted to focus. I considered starting a company, joining a later stage startup, trying to get a job in VC, or joining an early stage company. As I was doing this soul searching and research, I was having monthly beers with a friend of mine, Shane.
Shane and I would meet to grab drinks and talk about the ideas/side projects we were working on at the time. In October of 2018, he told me about the concept behind Mystery – a multiple stop night out where the reservations, tickets, and Lyft rides were taken care of in advance for you. You also wouldn’t know where you were going until you arrived!
At this point, Shane had planned a dozen or so Mysteries for friends and there was very little technology involved. You would create a profile by answering some questions in a Google Form and instructions were communicated via text. In November, my girlfriend at the time and I went on our first Mystery. Halfway through our adventure that night, I realized that this was unlike any product I had experienced before and I wanted to be involved.
Fast forward to March 2019 and I had been working nights and weekends for two months at Mystery out of a co-working space in Capitol Hill. As we started gaining some traction with customers and investors, I decided it was the right time to quit my job at Boeing.
3. What initial hesitations did you have about quitting your job and how did you overcome them?
The two main hesitations I had about quitting my job were potentially living without a salary and if Mystery failed, that it would limit my future career opportunities.
To overcome my financial hesitations, I took a realistic look at my current savings, my monthly expenses, and how I could significantly reduce those expenses. I then created a financial plan while I was at Boeing to save 6 months of living expenses in case there was a scenario where I wasn’t making a salary. Once I was able to build up this 6 month safety net, I was able to relax and focus on aspects of the decision that weren’t related to income.
My second concern was that if Mystery failed, that failure would stunt my future career growth (i.e. future companies wouldn’t want to hire someone who was part of the founding team at a failed startup). I found this to be absolutely wrong. Over the next few months, I received countless comments and pieces of feedback that regardless of Mystery’s success or failure, I would receive the same, if not better, future job opportunities because of it.
4. Can you remember the day you put in your notice? What was it like, what was going through your mind, how did your manager take it?
I remember it vividly. I scheduled a 1:1 with my manager and I shared the news that I was leaving to help start a company. We spoke about Mystery, the concept, and traction to date. She was bummed that I would be leaving, but was completely supportive and very happy for me!
I was pretty nervous going into the conversation because I didn’t know what the feedback was going to be from my manager, my peers, or my mentors within Boeing. Leaving Boeing to help start a company was not a normal route so I was unsure what the response was going to be.
Almost everyone was extremely supportive of my decision and a few senior Boeing employees even said, “I wish I had done that earlier in my career.”
After submitting my two week’s notice, I couldn’t shake this intense feeling of excitement and motivation. It was an intoxicating feeling and confirmed that quitting was the right thing to do.
5. What are you doing now?
Today I am the Head of Supply and part of the Founding Team at Mystery. Mystery is a Seattle-based startup that creates surprise experiences highlighting the best local things to do in your city.
I manage Mystery’s Supply organization where we establish relationships and partnerships with restaurants, bars, and activity providers in Seattle, Austin, and Denver.
6. Looking back on your experience of founding a company, what do you know now that you wish you knew before? Are you happy with your decision?
Joining Mystery was absolutely the right decision and I couldn’t be happier with my choice. There are many things I wish I knew at the beginning, but three stick out as the most important:
Prioritization is key
The most important and urgent items must be prioritized every day.
Things will always be broken, but if it doesn’t fall into either of those categories (important and urgent), it can wait.
Hire an incredible team
Look for people who are action oriented, relentlessly resourceful, agile, and fill the skill gaps for yourself and other team members.
We’ve had the opportunity to hire some truly remarkable people at Mystery and I’m proud to work with them everyday.
Get comfortable making quick decisions, often with a limited set of data
Quick decisions often don’t come with a complete data set and that’s OK.
Make the best decision you can, and as you learn more, you can always pivot.
7. Any other advice you can share for others contemplating a similar path?
In my opinion, most things in life are less risky than they first seem. If you’re considering venturing out, joining an early stage company, or starting a company, I’d recommend evaluating the following:
The absolute worst case scenario if you venture out
The likelihood of that scenario occurring
The positive outcomes that would occur if things went OK
The positive outcomes that would occur if things went very well
The happiness and joy you would feel building/joining something you’re truly passionate about
When I left Boeing, I think many people looked at my choice to join Mystery as extremely risky because I was leaving a stable job. But in my mind, it was the obvious decision. At Mystery, I could wake up everyday and build something that I was deeply passionate about. Although there were some potential risks, they were minuscule in comparison to the joy of working on something that excites me and the massive potential upside associated with helping start an early stage company.
On my last day, many people told me that I was always welcome back to Boeing and to reach out if I ever wanted to work for them. So even if things don’t work, you could probably go back to your previous company or get another job. And if that’s true, what’s the big risk anyways?
Interested in learning more about Mystery? Check out our experiences in Seattle, Austin, and Denver at https://www.trymystery.com/