DeAnn O’Donovan of Cypress Bay: “Define your target customer up front”

A soft launch. Being new to the card game industry, I knew that there were things I didn’t know. As a result, when I did the first edition of the game, I solicited critical feedback to identify what I might have missed. This has allowed me to refine quickly to create a game with wide appeal. […]

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A soft launch. Being new to the card game industry, I knew that there were things I didn’t know. As a result, when I did the first edition of the game, I solicited critical feedback to identify what I might have missed. This has allowed me to refine quickly to create a game with wide appeal.

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 DeAnn O’Donovan, Founder of Cypress Bay, LLC. Cypress Bay was founded during the early days of the pandemic to produce Quarantine The Card Game, a funny, family friendly game that became a break-out bestseller on an Etsy just weeks after its launch. DeAnn is also a divisional CEO for a community bank and has led several start-ups and established companies in finance, banking, and real estate before founding her game company.

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 grew up in a suburb of Minneapolis. I have great childhood memories of multi-generational card games played at my Grandparents’ cabin. We played an obscure version of rummy for hours at a time. That was an inspiration for me in developing Quarantine. My hope is that it will allow families to come together to play, have a few laughs, and make some new memories in what has been a challenging year for all of us.

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

Since we’re on the theme of childhood, I’ll go with a classic from Alice in Wonderland, “If you don’t know where you are going, any road will take you there.”

In one of my first jobs, my employer tried to track me into a traditionally female department. I took a hard look at the future growth potential in that role and found it didn’t track with my goals for myself. It was an early lesson that it’s up to each of us to choose our road and avoid the detours where possible.

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 Alchemist by Paulo Coehlo is an enduring favorite. It’s a seemingly simple quest story about following your dreams, overcoming obstacles, and returning to your path when life takes you off-track. When we start on any new endeavor — whether it’s a trip, falling in love, or starting a new business during the middle of a pandemic — our first feelings are excitement and inspiration. But the one thing we can expect is the unexpected. There are always challenges to be overcome and it is traits like tenacity, flexibility, and creative problem solving that help us manage through to a successful outcome.

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

Before the pandemic, I was working on launching a new private placement specialty finance company that invests in mortgages and related assets.

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

During the national shelter in place order in March, my husband and I started playing games and I quickly became bored with games for two people. I’ve always loved trump card games like spades and solving problems, so I set decided to create a new trump style card game that combined chance and strategy and had more variety than most games. That was the beginning of Quarantine The Card Game.

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

My husband and I were playing battleship (yes, we had a lot of time on our hands) and I sank all of his ships in about 20 minutes. In explaining how I did it (I had learned his pattern placement of ships on his board), I knew I could create a game that offered more chance, variety, and options for play.

How are things going with this new initiative?

The response to Quarantine has been terrific. To my surprise, Quarantine became an Etsy best seller within weeks of its launch. I’ve also had several independent game companies reach out to explore licensing & distribution options. It’s been great to have customers tell me how much they’re enjoying it with their family, or see people come back to buy more decks to gift to friends and family. I’ve always believed in giving back, so 5% of profits will be donated to charity to help those hardest hit by the pandemic. That is also gratifying, the opportunity to do well by doing good.

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?

A number of family members have been big supporters of the game. My husband is a serial entrepreneur & he was a big believer that it would find a market. My daughter Nieve has been giving me tips to promote it on social media. So overall, I’d say I’m grateful to my family not just for the support, but because that support comes with concrete questions, suggestions, and feedback.

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

As I mentioned earlier, until this point my career has primarily been in the finance sector. My inner critic was worried that I knew nothing about how to really manufacture or market a new game. I asked myself the usual “what if” questions — What if it bombs? What if it’s not funny? What if people are offended by it?

After I produced it, I sent an email with a link to the game to a few game distributors and independent retailers and the feedback was so positive it blew me away. One large distributor in particular struck me — he congratulated me and promptly suggested he’d like to distribute it through major channels. I haven’t gone that route yet, but it was the moment when I saw a larger future for the business.

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.

Number 1 is social media. I have always thought that social media was a time vaccum and as a result the only social media I was on was LinkedIn. For a game like Quarantine, social media is a great opportunity to promote brand awareness & drive sales. I’m learning this on the fly. In retrospect, I should have been on Facebook & Instagram to build a following over the course of my prior career so I had a platform to start from.

Number 2 is to define your target customer up front. I should have done this earlier in the process so I had a laser focused marketing plan. I did this shortly after launch and quickly pivoted to Etsy, which proved to be a great move.

Number 3 is how to find top contract talent. I had some early wins but also some misses on this one. When I’m hiring a traditional employee, I give the finalists a small project that reflects the work they are going to be doing on the job. For example, if I’m hiring a CFO, I will give them the financials and ask them to put together a sample board presentation. In cases where I invested the time and money to do this with contract workers, I made the right hire, such as with my graphic designer. In cases where interviewed and hired without doing a test project first, the results were mixed. For example, I hired someone to set up my Amazon store and it has been fraught with problems and delays.

Number 4 is to learn enough about the systems you are working with to adequately supervise your staff and be able to manage it yourself in an pinch. Sticking with the Amazon contractor, I hadn’t taken the time to really learn the basics of selling on Amazon. I wanted to out-source it and hit the ‘easy’ button. It’s cost me more time, money, and opportunity cost as a result. I contrast this with Etsy which now accounts for about 60% of my sales. I invested more time in looking at how other successful sellers set up their shop, learning their ads, personally testing promotions, and taking advantage of the support Etsy has built into their platform.

Number 5 is what I call a soft launch. Being new to the card game industry, I knew that there were things I didn’t know. As a result, when I did the first edition of the game, I solicited critical feedback to identify what I might have missed. This has allowed me to refine quickly to create a game with wide appeal.

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?

I meditate daily and have for many years. It brings me a deep stillness and calm. Even though I’m not thinking about work during that time, I am often more energized, focused, and creative after meditating. If I miss a few days, I feel the difference in all areas of my life. I also take breaks from the news when it gets too repetitive. The world will still be there tomorrow.

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?

Look for opportunities to do well by doing good in business. I’m donating 5% of net profits from Quarantine to charity to help those hardest hit by the pandemic. In my last finance CEO role, we were a socially responsible company focused on helping struggling homeowners retain the dream of homeownership. Whatever industry you are in, there are opportunities to do it in a way that benefits the business, your customers, and the broader community. Find those opportunities.

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!

Elan Lee and Matt Inman, the creators of the game “Exploding Kittens”. I like their origin story and the games they’ve created are funny and irreverent. If you can get me a lunch date with them, there are free games in your future!

How can our readers follow you online?

Readers can follow me at They can also connect with me on LinkedIn, Facebook, and Instragram.

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

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