7 min 43 sec

Shy Expat Uses “Deep Questions” Cards to Spark Conversations

A video marketer designs playing cards he calls “Ask Deep Questions” to help spark conversations and create meaningful connections
Community Crowdfunding Design Manufacturing Product WDS

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What It's About

"It's like cards for humanity"—a shy expat creates a special card deck to spark conversation and connection.

Business Model
Skills Required
Community Building & Design
Profit Potential

Words of Wisdom

As Jan so eloquently put it, "you should start small and create a prototype first that you can use to play-test your concept. Invite as many people to share their feedback, and make small adjustments until you have a product you know people will buy."

Creating an MVP to determine the success of a venture is never a bad call!

Fun Fact

Ask Deep Questions drew inspiration from a 2017 WDS event. There was a moment when Jan signed up for the “Leap of Faith” and boarded a school bus alongside a group of strangers with an unknown destination. During the drive, one person had to stand up with a megaphone and answer a question to the whole bus. The rest of the passengers would then turn to their neighbor and answer the same question. Jan said he almost enjoyed the bus ride more than the secret event (which turned out to be ziplining) and met some amazing people this way!

Notes from Chris

Episode 804
Growing up in Germany, Jan Keck was the perennial shy kid. The mere thought of his teachers calling on him resulted in a serious case of the butterflies. As he put it, “I was the guy who sat next to you in math class who years later you completely forgot.”

But, like all of us, he still craved connections.

Fast forward a decade, and Jan was living in Canada on an internship for his studies. He met a girl, fell in love, and decided to make Toronto his home.

In his early years there, he still wasn’t fluent in the language. Despite the numerous friendly Canadians he met, he found it difficult to forge deep connections with people.

Then a couple of years ago, something changed. He organized a camping trip for some friends and wanted to find a way for them to get to know each other on the four-hour road trip that lay ahead.

He collected a bunch of questions he found online, then printed them onto cards and handed a deck to each car. Surprisingly, it turned the whole weekend trip into a collection of meaningful conversations. It allowed a group of strangers to become much closer to each other.

When the trip was over, everyone asked where they could buy a deck of cards for themselves. That’s when Jan started thinking about going deeper with his idea...

Over the following months, he did a lot of testing, researched printers, designed new cards and packaging, and three months later officially launched his creation as a product. He called it Ask Deep Questions.

He started small, ordering 180 decks. When they arrived, he hosted a small launch party, inviting friends over to celebrate with—what else—some deep conversations.

Four months later, he sold out and ordered another 200 decks, which also sold out. Realizing he was on to something, he published a Kickstarter campaign that raised over $15,000 to pay for the production of 1,000 decks in November 2018.

His decks sell for $35 each, up from the original price of $30 per deck. This hustle earns him $1,000 a month through his website with an additional $300-500/month coming through in-person sales at events.

To manufacture the cards, he first reached out to a couple of factories through Alibaba, but he found it to be too much of a hassle. Things took a turn for the better when he was introduced to a print broker through a referral. That broker was able to get sample decks made and took care of all the communication with the factory located in Hong Kong.

The broker cost Jan $250, and he said it was worth every penny. He didn’t even know that sort of person existed up to this point!

As far as shipping and receiving go, Jan is still handling it himself—for now. He’s got an assortment of card decks stacked in his office along with plenty of bubble wrap and envelopes.

He’ll soon be retiring his home shipping center and transitioning to a storefront on Amazon, which will handle fulfillment. He wants his next big order to ship directly to Amazon’s warehouse so he doesn’t have to do it anymore.

He’s also focused on creating more experiences in the shape of smaller events and workshops to help people combat their feelings of loneliness. Working on expansion decks to help facilitators create deeper connections for their communities is step one.


  • Ask Deep Questions Card Deck: Learn more about Jan's special card deck and order your own through his website
  • Campfire Conversations and LevelUp: Jan's events that he uses to help promote Ask Deep Questions
  • Kickstarter: The crowdfunding platform Jan used for his first, large deck order
  • Alibaba: The marketplace Jan initially used to try and find a manufacturer for Ask Deep Questions


Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,


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Quote of the Day
"Start small and create a prototype first that you can use to play-test your concept. Invite as many people to share their feedback and make small adjustments until you have a product you know people will buy."
—Jan Keck #SideHustleSchool

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