Witty Risk-taker Gifts

Looking for a gift that matches the adventurous spirit of a witty risk-taker? Our curated collection features clever and daring designs on mugs, t-shirts, pillows, and prints, perfect for those who embrace life's challenges with humor and style. Surprise your bold friend or loved one with a gift that celebrates their fearless attitude, combining wit and courage in one playful package.

All Products Prints T-Shirts Mugs Pillows

'I'll bet you fifty dollars that you can't stop gambling.'

'I'll bet you fifty dollars that you can't stop gambling.' mockup

'I'll bet you fifty dollars that you can't stop gambling.'

from $19.00

"Forget five-year plans. Let's just figure out how to make it to lunch."

"Forget five-year plans. Let's just figure out how to make it to lunch." mockup

"Forget five-year plans. Let's just figure out how to make it to lunch."

from $19.00

'Past performance is not an indication of future results.'

'Past performance is not an indication of future results.' mockup

'Past performance is not an indication of future results.'

from $19.00

The fate of the emigrant

from $19.00

'The prevailing wisdom is that markets are always right. I think that luck is always right.'

'The prevailing wisdom is that markets are always right. I think that luck is always right.' mockup

'The prevailing wisdom is that markets are always right. I think that luck is always right.'

from $19.00

Clyde thought “Atomic Sparklers” was just an ad gimmick

Clyde thought “Atomic Sparklers” was just an ad gimmick mockup

Clyde thought “Atomic Sparklers” was just an ad gimmick

from $19.00

Due to his low center of gravity, Jake is the greatesr broncbuster ever!

Due to his low center of gravity, Jake is the greatesr broncbuster ever! mockup

Due to his low center of gravity, Jake is the greatesr broncbuster ever!

from $19.00

A slice of bread walks a tightrope between slots on the toaster.

A slice of bread walks a tightrope between slots on the toaster. mockup

A slice of bread walks a tightrope between slots on the toaster.

from $19.00

Bite out of fishing pier.

from $19.00

"Hey, you stick your neck out on a regular basis, it's gonna happen. The important thing is to just get up and keep moving forward."

"Hey, you stick your neck out on a regular basis, it's gonna happen. The important thing is to just get up and keep moving forward." mockup

"Hey, you stick your neck out on a regular basis, it's gonna happen. The important thing is to just get up and keep moving forward."

from $19.00

Dear Diary. . . why, oh why, did I choose an adventure holiday?

Dear Diary. . . why, oh why, did I choose an adventure holiday? mockup

Dear Diary. . . why, oh why, did I choose an adventure holiday?

from $19.00

'I want you to paddle against the current.'

'I want you to paddle against the current.' mockup

'I want you to paddle against the current.'

from $19.00

"But don't let my wacky tie fool you. We actually take business very seriously around here."

"But don't let my wacky tie fool you. We actually take business very seriously around here." mockup

"But don't let my wacky tie fool you. We actually take business very seriously around here."

from $19.00

Pilot with champagne.

from $19.00

Job Vacancy: Human cannonball. Applicants must of the right calibre

Job Vacancy: Human cannonball. Applicants must of the right calibre mockup

Job Vacancy: Human cannonball. Applicants must of the right calibre

from $19.00

'According to this book, the casino has a slight edge in this game.'

'According to this book, the casino has a slight edge in this game.' mockup

'According to this book, the casino has a slight edge in this game.'

from $19.00

"We have all the brochures, but we can't decide if we want to die on Mt. Everest or Mt. McKinley."

"We have all the brochures, but we can't decide if we want to die on Mt. Everest or Mt. McKinley." mockup

"We have all the brochures, but we can't decide if we want to die on Mt. Everest or Mt. McKinley."

from $19.00

"Marco ..."

from $19.00

Then get under cover before you are struck by lightning.

Then get under cover before you are struck by lightning. mockup

Then get under cover before you are struck by lightning.

from $19.00

On the brink.

from $19.00

The Tightrope Balancing Act of Home Ownership and Interest Rates.

The Tightrope Balancing Act of Home Ownership and Interest Rates. mockup

The Tightrope Balancing Act of Home Ownership and Interest Rates.

from $19.00

-Sorry about yesterday, I was ill! -You didn't look ill when I saw you at the races! -You didn't see me after the fifth leg!

-Sorry about yesterday, I was ill! -You didn't look ill when I saw you at the races! -You didn't see me after the fifth leg! mockup

-Sorry about yesterday, I was ill! -You didn't look ill when I saw you at the races! -You didn't see me after the fifth leg!

from $19.00

"Remember how I've always had a hard time asking for help?"

"Remember how I've always had a hard time asking for help?" mockup

"Remember how I've always had a hard time asking for help?"

from $19.00

"Steady. This is going to be so sweet." mockup

"Steady. This is going to be so sweet."

from $19.00

Slipping and sliding down the slope... mockup

Slipping and sliding down the slope...

from $19.00

'I don't like to take chances.'

from $19.00

Humpty Dumpty goes bungee jumping. mockup

Humpty Dumpty goes bungee jumping.

from $19.00

'You know what they say...live fast, die young and leave a great fossil.'

'You know what they say...live fast, die young and leave a great fossil.' mockup

'You know what they say...live fast, die young and leave a great fossil.'

from $19.00

Look At Me I'm Still Wearing Shorts. mockup

Look At Me I'm Still Wearing Shorts.

from $19.00

"In my old job we were encouraged to run fast and break things."

"In my old job we were encouraged to run fast and break things." mockup

"In my old job we were encouraged to run fast and break things."

from $19.00

'Mind taking off your scarf.'

from $19.00

I was trying to day trade my way through business school, but then the stock market tanked.

I was trying to day trade my way through business school, but then the stock market tanked. mockup

I was trying to day trade my way through business school, but then the stock market tanked.

from $19.00

The deadly sport of cobra staring contests.

The deadly sport of cobra staring contests. mockup

The deadly sport of cobra staring contests.

from $19.00

'The reason I like this guy's stock picks is, he's not burdened by having any experience in finance whatsoever.'

'The reason I like this guy's stock picks is, he's not burdened by having any experience in finance whatsoever.' mockup

'The reason I like this guy's stock picks is, he's not burdened by having any experience in finance whatsoever.'

from $19.00

"Life's a lottery - That's why you need balls"

"Life's a lottery - That's why you need balls" mockup

"Life's a lottery - That's why you need balls"

from $19.00

Witty Risk-taker Gifts Collection

Witty Risk-taker Mugs

Explore our collection of mugs designed for the witty risk-taker—perfect for starting conversations and mornings with a smile.

Witty Risk-taker Pillows

Find the perfect pillow that celebrates bravery and wit—ideal for adding a humorous touch to any living space.

Witty Risk-taker Prints

Browse our prints collection to discover bold, humorous designs that capture the spirit of a witty risk-taker and inspire everyday courage.

Witty Risk-taker T-Shirts

Check out our t-shirts for the risk-taker who loves bold, clever designs—great for making a humorous statement everywhere they go.