Looking for a playful way to energize your entrepreneurship community? Guessing Game posts offer a lighthearted format that encourages members to jump in and share their thoughts. With ready-to-use templates, you can spark curiosity and drive more interaction, no matter your platform.
Connect your community and StickyHive auto-posts these templates on the best days & times for engagement.
Guessing Game content taps into the natural human curiosity to solve puzzles and be part of the action. When entrepreneurs see a fun challenge or intriguing clue, they are tempted to participate, even if just to see if they can guess correctly. This creates a feeling of involvement and friendly competition, which are both powerful motivators for community engagement.
For entrepreneurship communities in particular, Guessing Games encourage members to flex their business knowledge, share their instincts, and connect over shared interests. These games lower the barrier to participation, making it easy for even shy members to join in. The lighthearted tone keeps things enjoyable, while the clues can subtly reinforce key entrepreneurial concepts or celebrate community wins.
Guess which famous entrepreneur started their first business at age 12.
💡 Example: "Guess which famous entrepreneur started their first business at age 12. Who do you think it is?"
I am a tech company founded in a garage. Can you guess which one?
💡 Example: "I am a tech company founded in a garage. Can you guess which one? Drop your answer below!"
Which popular app was originally a side project? Take a guess.
💡 Example: "Which popular app was originally a side project? Take a guess."
Guess the year: When was crowdfunding first used online?
💡 Example: "Guess the year: When was crowdfunding first used online? Closest guess wins bragging rights."
I pitched my product on Shark Tank and became a household name. Who am I?
💡 Example: "I pitched my product on Shark Tank and became a household name. Who am I?"
Guess what percentage of small businesses survive their first five years.
💡 Example: "Guess what percentage of small businesses survive their first five years. What's your guess?"
This entrepreneur once sold newspapers as a kid. Can you name them?
💡 Example: "This entrepreneur once sold newspapers as a kid. Can you name them?"
Which famous company started with just $500? Guess the name.
💡 Example: "Which famous company started with just $500? Guess the name in the comments."
I launched my first startup from a dorm room. Who am I?
💡 Example: "I launched my first startup from a dorm room. Who am I? Take a guess!"
Guess the product: I am now everywhere, but started as a failed food experiment.
💡 Example: "Guess the product: I am now everywhere, but started as a failed food experiment. What do you think?"
Which entrepreneur wrote their first code at age 13? Guess the name.
💡 Example: "Which entrepreneur wrote their first code at age 13? Guess the name."
I am a startup valued over a billion dollars. Guess what I am called.
💡 Example: "I am a startup valued over a billion dollars. Guess what I am called."
Guess which iconic logo was sketched on a napkin.
💡 Example: "Guess which iconic logo was sketched on a napkin. Any ideas?"
Which entrepreneur famously failed twice before succeeding? Who is it?
💡 Example: "Which entrepreneur famously failed twice before succeeding? Who is it?"
Guess the startup: Our first office was a coffee shop.
💡 Example: "Guess the startup: Our first office was a coffee shop."
I raised my first funds on Kickstarter. Can you guess my product?
💡 Example: "I raised my first funds on Kickstarter. Can you guess my product?"
Which business term means 'minimum product to test the market'? Guess it.
💡 Example: "Which business term means 'minimum product to test the market'? Guess it."
I am an entrepreneur who started with a lemonade stand. Who am I?
💡 Example: "I am an entrepreneur who started with a lemonade stand. Who am I?"
Guess which company was named after a fruit.
💡 Example: "Guess which company was named after a fruit. Drop your answer!"
Which founder delivered pizzas before launching their business? Guess who.
💡 Example: "Which founder delivered pizzas before launching their business? Guess who."
I am a business book every entrepreneur should read. Can you name me?
💡 Example: "I am a business book every entrepreneur should read. Can you name me?"
Guess which social media platform started as a college-only network.
💡 Example: "Guess which social media platform started as a college-only network."
Which entrepreneur turned a failed product into a billion-dollar company? Guess who.
💡 Example: "Which entrepreneur turned a failed product into a billion-dollar company? Guess who."
I am a famous pitch event for startups. What am I called?
💡 Example: "I am a famous pitch event for startups. What am I called?"
Guess the monthly fee: How much did Netflix originally charge?
💡 Example: "Guess the monthly fee: How much did Netflix originally charge?"
Which founder started out as a teacher? Guess their name.
💡 Example: "Which founder started out as a teacher? Guess their name."
I am a company that began in a college dorm. Can you guess which one?
💡 Example: "I am a company that began in a college dorm. Can you guess which one?"
Guess which common office supply was invented by an entrepreneur.
💡 Example: "Guess which common office supply was invented by an entrepreneur."
Which business podcast has the most entrepreneur guests? Take a guess.
💡 Example: "Which business podcast has the most entrepreneur guests? Take a guess."
Guess the name: My business is known for its swoosh logo.
💡 Example: "Guess the name: My business is known for its swoosh logo."
Who am I? I failed at three startups before hitting it big.
💡 Example: "Who am I? I failed at three startups before hitting it big."
Guess which business term means 'customer leaves positive feedback publicly.'
💡 Example: "Guess which business term means 'customer leaves positive feedback publicly.'"
Which product was invented by accident in the 20th century? Guess it.
💡 Example: "Which product was invented by accident in the 20th century? Guess it."
I am the youngest self-made billionaire. Can you guess who I am?
💡 Example: "I am the youngest self-made billionaire. Can you guess who I am?"
Guess which company uses a penguin as its mascot.
💡 Example: "Guess which company uses a penguin as its mascot."
Which entrepreneur started out selling products from their car trunk? Who is it?
💡 Example: "Which entrepreneur started out selling products from their car trunk? Who is it?"
Guess the tool: I help teams collaborate online and was launched in 2013.
💡 Example: "Guess the tool: I help teams collaborate online and was launched in 2013."
Which startup was inspired by a need to split rent payments? Guess the name.
💡 Example: "Which startup was inspired by a need to split rent payments? Guess the name."
Who am I? I wrote a business plan on the back of a napkin.
💡 Example: "Who am I? I wrote a business plan on the back of a napkin."
Guess which entrepreneur dropped out of college to start their company.
💡 Example: "Guess which entrepreneur dropped out of college to start their company."
I am a business tool used by millions, but started as a hobby project. Guess me.
💡 Example: "I am a business tool used by millions, but started as a hobby project. Guess me."
To use these templates, simply copy and paste a prompt into your community platform of choice. Add a relevant clue or tweak the details to fit your audience. Encourage members to reply with their guesses and consider revealing the answer after some participation to keep the momentum going. Rotate through different types of guessing games to maintain interest and invite all member types to join.
On all platforms, use clear formatting to highlight the guessing clue. Pin or bump the post if possible to keep it visible. Consider tagging or mentioning members to encourage participation, and use emojis to add a playful touch.
Aim for 1-2 times per week to keep things fun and engaging without overwhelming members.
Reveal the answer after a while and encourage discussion around it to maintain momentum.
Absolutely. Customize clues to reference current events, popular entrepreneurs, or your own community milestones.
Use simple questions, tag members, and create a welcoming tone to lower the barrier for first-time posters.
Prizes can boost engagement, but often the fun and recognition are enough to motivate participation.
Wait for several responses to maximize engagement, then share the answer and celebrate participants.
Yes, the format is flexible and works well for any size group. Adjust the difficulty and frequency as needed.
No credit card • Setup in 2 min