Born and raised in Sweden, Toby moved to the United States in 2009 and eventually settled in Fargo, North Dakota.

These days, life revolves around family, work, and two hobbies he is especially passionate about: watches and whiskey.

Like many enthusiasts, Toby’s interest in watches did not begin with luxury timepieces.

For years, he wore a smartwatch before deciding he wanted something with a little more character.

“I got tired of wearing a smartwatch,” he said.

About two years ago, he began exploring the world of mechanical watches, starting with microbrands and discovering just how much enjoyment came from wearing something thoughtfully made.

“I think a beautiful watch is the one piece of jewelry a man can wear that doesn’t stick out too much.”

That passion only grew.

For his 50th birthday, Toby’s wife surprised him with his very first luxury watch, a Rolex Datejust.

“It gives you that little extra spark.”

Since then, he has immersed himself in the hobby, following watch pages online and learning everything he could. His favorite brands quickly became Rolex, IWC, and Cartier, with Audemars Piguet and Patek Philippe sitting high on his dream list.

Then came Wolf Watch Club.

Like many first time players, Toby admits he was skeptical.

Working in financial crimes and fraud investigations, he naturally approached everything with caution. He researched multiple watch competition companies, read reviews, checked Reddit, and watched previous winners before deciding Wolf Watch Club was the one he trusted.

His first draw was the Rolex Submariner “Starbucks.”

His second was the IWC Ingenieur Winner’s Choice.

He was not able to watch the live draw because of family commitments, but later that evening he remembered to check the results.

“I still couldn’t believe it.”

After looking over all four dial options, Toby chose the blue Ingenieur.

“It came down to the blue or the aqua, but I think the blue goes with a lot more things.”

The win now means he owns watches from two of his favorite brands, Rolex and IWC.

Perhaps the most refreshing part of Toby’s story is why he plays.

“I’m not trying to win a watch so I can sell it,” he said. “I want to win something that I’ll enjoy.”

That philosophy made the Ingenieur the perfect prize.

And while he has already crossed one grail off his list, Toby is not finished just yet.

The Rolex Submariner “Starbucks” and the GMT Master II “Bruce Wayne” are still firmly on his wish list. After seeing his name called once, he is convinced anything is possible.

As for those dream APs and Pateks?

“Who knows? Maybe with Wolf Watch Club one day they’ll be mine.”

Some winners hear their name called and immediately know what’s happening.

James Potter almost missed it.

On the day of the Rolex Daytona draw, James was at his in-laws’ house enjoying a family barbecue. Between spending time with family and the excitement of the day, the live draw wasn’t exactly at the front of his mind.

“I got in at the very end, right before he did the draw.”

As he joined the livestream, Jory made a joke about Harry Potter.

For James, that wasn’t unusual.

“My name is James Potter. If you’ve ever read the Harry Potter books, James Potter is Harry Potter’s dad.”

At first, he assumed Jory was simply having a bit of fun after noticing him enter the stream.

“I thought maybe he was just welcoming me because he saw me come in.”

But that wasn’t what was happening at all.

Jory wasn’t welcoming him.

He was announcing him as the winner.

“He had actually called my name because I won.”

Even now, James still struggles to describe the feeling.

“It was so surreal.”

The victory was especially remarkable because James won one of Wolf Watch Club’s largest Rolex draws ever with just three tickets.

Three tickets.

One Rolex Daytona.

When we spoke afterward, James was still trying to process it.

“I couldn’t believe it.”

The first people he shared the news with were the people around him that day.

His wife.

His family.

His in-laws.

And then his friends.

One of them had become part of the story weeks earlier.

James had recently met a coworker who also happened to be a watch enthusiast. After discovering their shared interest, James introduced him to Wolf Watch Club.

Before the Daytona draw, the two exchanged some friendly trash talk.

“I sent him a chat and said, ‘Hey, wish me luck for the Daytona draw this weekend.’”

“He said, ‘No way. I’m winning that. I’m not wishing you luck.’”

A few days later, James got to send the message every watch enthusiast dreams of sending.

“Dude, were you on the live draw? Did you see what happened to me?”

His friend hadn’t watched.

So James delivered the news himself.

“I just won.”

For James, the Daytona wasn’t just another watch.

Watches have been part of his life for decades.

His journey began with a Star Wars watch in elementary school.

“It had Han Solo and Princess Leia on it.”

Then came a yellow Casio G-Shock in high school.

“I wore that thing for five or six years. I wore it everywhere.”

Over time, his collection evolved through Seikos, Citizens, sports watches, Garmin models, and eventually his first luxury watch: a Rolex Explorer II.

James still remembers buying it after a career milestone.

“That was my first luxury watch.”

Years later, following a divorce, he had to sell it.

But his love for watches never left.

Today his collection includes several Seikos, independent brands, sports watches, and now one of the most sought-after watches in the world… a Rolex Daytona.

What makes James’s story even more relatable is that he never expected to own one.

“I personally was like, ‘I’ll never have this watch.’”

Not because he didn’t appreciate it.

Because, like many enthusiasts, he saw it as unattainable.

“I couldn’t afford it.”

“And I wouldn’t wait five years for it.”

That’s part of what drew him to Wolf Watch Club in the first place.

James discovered Wolf while watching watch content on YouTube.

“YouTube learns what you’re interested in.”

“If it’s not giving me pickleball videos, it’s giving me watch videos.”

One day, Wolf Watch Club appeared on his radar.

“I was like, ‘Wait a second. You can buy a ticket and be in it for a watch?’”

Before long, he was entering selectively, choosing watches that genuinely interested him.

Rolex.

Tudor.

Omega.

The pieces that told a story.

Over time, he entered 12 draws.

When asked why he kept coming back, his answer was simple.

“The hope and excitement of winning a watch.”

And for James, watches are more than objects.

They’re milestones.

Memories.

Stories.

“I love watches that tell a story.”

That perspective extends beyond watches as well.

James lives in Scottsdale, Arizona, works in IT consulting, enjoys pickleball, hiking, travel, and spending time with his church community.

He has hiked the Grand Canyon multiple times.

He and his wife spent four weeks exploring Italy during a sabbatical.

And next on the travel list are Banff, Aruba, and Jamaica.

But despite all those adventures, hearing his name called for the Daytona ranks among the most memorable moments.

As a man of faith, James views the win through a different lens.

“I’m a strong Christian.”

“I have no doubt that this is the Lord’s blessing.”

When he thinks about the odds, it still takes his breath away.

“You buy three tickets and actually win? It just takes my breath away.”

Today, James has a Rolex Daytona on the way.

The watch he never expected to own.

The watch he thought was out of reach.

The watch that turned a family barbecue into a day he’ll never forget.

And if you ask him whether Wolf Watch Club is real?

His answer is straightforward.

“For somebody who’s into watches, it’s an opportunity to try to win something for a relatively small investment.”

You can’t win if you’re not in it.

James bought three tickets.

And walked away with a Rolex Daytona.

Some wins happen on a first try.

Others come after months of showing up, staying patient, and believing your turn will eventually come.

For Guillermo Velarde, it was the second path.

Originally from Peru, Guillermo moved to Canada more than 20 years ago before eventually relocating to the United States for work.

“I was born in Peru and migrated to Canada 20 years ago, the last 10 in the US, always for work.”

Today, work keeps him moving.

“I travel a lot for work.”

When he’s not on the road, he enjoys following tennis, although he admits he doesn’t get to play as often as he’d like.

Like many Wolf Watch Club members, Guillermo didn’t discover the platform through social media or YouTube.

He found it while researching watches online.

“By Googling my last watch, Wolf and other similar sites started to show up.”

Before entering, he took the time to do his homework.

“I did my research prior to participating the first time by verifying your website, reviews, etc.”

After deciding to give Wolf Watch Club a try, Guillermo became one of those familiar names that kept appearing week after week.

Draw after draw, he kept showing up.

He kept entering.

And he kept believing his turn would come.

Then one Sunday, it finally did.

Guillermo was selected as the winner of the Omega Speedmaster Moonwatch.

His reaction?

“Extremely happy as I was trying for several months.”

For someone who had been consistently supporting Wolf Watch Club and participating draw after draw, the win felt especially rewarding.

While Guillermo doesn’t consider himself a serious watch collector, watches have always been something he’s appreciated.

“Not really a collector, but I do have some.”

His collection already included a Rolex and a Breitling before adding the Speedmaster.

But winning one of the most iconic watches ever made may have changed things.

“Maybe with this one I’m now a collector.”

The Omega Speedmaster Moonwatch is a watch with a story unlike any other, a watch worn during NASA missions and forever connected to space exploration.

For Guillermo, it also represents patience paying off.

He sees it as an opportunity for watch enthusiasts who might not otherwise have access to these kinds of timepieces.

“I think it is a good opportunity for people that want to give it a try.”

And for anyone who is considering entering Wolf Watch Club for the first time, Guillermo’s advice comes from experience.

After months of entering before finally hearing his name called, he understands better than most that patience matters.

“Give it a try, don’t despair and be patient.”

Congratulations again to Guillermo Velarde, winner of the Omega Speedmaster Moonwatch White Dial. 

After months of showing up, supporting Wolf Watch Club, and believing his turn would come, Guillermo’s patience paid off!

For Don Off, watches have never just been about watches.

They’re about memories, milestones, and one day passing something special on to his two sons.

Don has been a watch enthusiast for more than 20 years. A Rolex was the watch that started it all, and over time his appreciation for watches only grew stronger.

A few years ago, he found himself diving back into the hobby.

“I really started getting back into watches. For some reason it just clicked.”

What followed was familiar to many collectors: countless hours spent researching references, watching reviews, and learning about the watches he admired.

“I bought a couple more. Started watching watch videos quite a bit, just researching stuff.”

Eventually, that search led him to Wolf Watch Club.

After doing his research, he decided to give it a try.

What he didn’t expect was that the Sunday live draw would become part of his weekly routine.

“Every Sunday became part of what I did.”

As the weekend wound down, Don would make dinner, get ready for the upcoming work week, and tune into the live draw.

“I’d make dinner or whatever and get everything ready for the next week.”

Week after week, he kept showing up.

“Jory does a great job. It’s enjoyable to watch.”

In fact, it became something he genuinely looked forward to.

“I look forward to it every week.”

Then came the night every player dreams about.

After participating in more than 30 draws, Don was watching live when Jory called his name as the winner of the Rolex GMT-Master II “Batgirl.”

“Talk about exciting when he actually called out your name.”

Then there were his two sons.

As soon as they heard about the Rolex, Don jokingly realized he had created a new problem.

“I’ve got two boys.”

Then he laughed.

“Something to fight over.”

A few days later, something remarkable happened.

While at work, Don noticed an email arrive in his inbox.

“I saw an email pop up.”

He opened it and discovered he had won another Rolex GMT-Master II through a different watch competition company….this time a Batman.

The solution immediately became obvious.

“I called the kids up and said, ‘We have a problem solved.’”

One GMT for each son.

It’s a funny story, but it also reveals something important about why Don loves watches in the first place.

“A big part of why I partake in these competitions is the thought of enjoying the watch for a while and then giving it to my sons.”

“There would be no better feeling to me seeing the enjoyment they would get owning and wearing one as I did as a young man.”

And when it comes to the Rolex Submariner “Hulk,” he already knows exactly which son it belongs to.

“The Hulk is one I definitely could see my youngest wearing and find perfectly suited to his personality.”

That perspective says a lot about Don.

While most people enter hoping to win a watch for themselves, Don is already thinking about the next generation.

The memories.

The stories.

And one day handing those watches to his sons.

When asked whether he’d keep playing after winning the Batgirl, his answer came quickly.

“No, no. I’m going to be in the draws.”

And then he added:

“I’m going to look forward to winning again.”

Congratulations again to Don Off, winner of the Rolex GMT-Master II “Batgirl.”

For Don, the watch is more than a prize. It’s another chapter in a collection that he hopes will one day become part of his family’s story as well.

Andrew Bennett had just been talking about the “Root Beer” earlier that week. Then he opened his email.

He’s a physician by trade, someone who’s built his career on precision, patience, and long hours. Watches, for him, started as something personal. A milestone tied to hard work and progress.

“My first serious watch was an Omega Speedmaster… I rewarded myself with when I finished training.”

That watch stayed with him for years. And when it finally gave out, it pushed him deeper into the world of watches.

“The estimate was greater than the value of the watch… so that got me into looking at other watches.”

From there, his collection grew. A Rolex Datejust. Then an Explorer.

“At this point I really got the bug for watches.”

Andrew discovered Wolf Watch Club through a YouTube creator he followed.

“You guys sponsored him… and that’s how I found out about Wolf Watch Club.”

He didn’t jump in heavily. He played selectively.

“I may have done seven or eight raffles.”

Then came a moment that felt almost too perfectly timed.

While in Toronto for a conference, Andrew was talking watches with a colleague.

“He brought up the root beer… I thought, ‘Oh yeah, that’s a beautiful watch.’”

Later that same week, he saw it listed.

“I thought, ‘Wow, that’s pretty neat.’ So I bought 10 tickets.”

What happened next didn’t feel real.

“I opened my email to see that I won… which is pretty bananas.”

After a long flight back home, he landed, checked his phone, and saw it.

“When I land, I see that I won.”

His reaction was immediate.

“My first thought was that this is proof that we really do live in a simulation… like Donnie Darko style or something.”

“That was startling. No lie.”

He kept it close at first.

“I haven’t really told anyone… other than a couple of close friends and family.”

What made the win even more meaningful was how aligned it felt.

“I have been more interested in world timers and GMTs.”

“I was pretty excited to get a different version of a GMT… especially since it’s so difficult to get usually.”

Outside of watches, Andrew balances his profession with creativity.

“I’ve been spending my free time learning stone carving and clay modeling of figures and portraits.”

And when it comes to the experience as a whole, one thing stood out.

“It’s wonderful… otherwise a lot of these watches wouldn’t be accessible to people.”

He summed it up best.

“It feels like a private club… a secret entrance into watch collecting.”

From a conversation at a conference, to 10 tickets, to winning the very watch he had just been talking about, Andrew’s story came together fast.

And just like that, the Root Beer was his.

Allen is a 70-year-old realtor based in Tsawwassen, just outside Vancouver. He’s spent decades in real estate, and over that time, watches have quietly been part of his life and identity.

“I bought my first Rolex… 45 years ago.”

That first piece was an Oyster Perpetual. Not long after, he added more to his collection, including a Day-Date he later let go.

“And I wish I wouldn’t have sold it now.”

Over the years, his collection evolved. Some watches stayed, some moved on, and a couple even found their way to his wife.

“My wife took both of those… I haven’t been allowed to wear them for over 20 years.”

His interest never faded.

When Allen first came across Wolf Watch Club, it wasn’t random. It came through a trusted recommendation during a conversation with a local jeweler he had done business with for years.

“He said… the one I know is legitimate is Wolf Watch Club.”

That mattered.

“There’s so many scams on the internet right now… I’m very, very cautious.”

Allen had seen it all online. Ads, pop-ups, offers that didn’t feel right.

“Lots of times, my advanced security will block them.”

But this one was different.

So he gave it a shot. Nothing excessive. Just a few entries across a handful of draws.

“I haven’t been in many… I’ve been in the last four or five or six maybe.”

And then, out of nowhere, it happened.

Allen won the Rolex GMT-Master II “Bruce Wayne.”

He didn’t even see it live.

“They saw it and they phoned me.”

At first, he didn’t believe it.

“I thought… I think you’re looking at something else.”

Even his family was cautious.

“My son even emailed you back.”

In today’s world, that hesitation makes sense. Allen had recently experienced a scam himself, which only reinforced how careful he had become online.

“I’m very, very, very, very cautious.”

But this time, it was real.

When the watch arrived, the moment hit immediately.

“I love it. It’s beautiful. I’m thrilled.”

Holding it in his hands, seeing it up close, it all clicked.

“It’s an absolutely beautiful watch. I’m very thrilled. I appreciate it.”

There was just one small problem.

“I can’t get it over my hand.”

Even that didn’t take away from the moment. Standing there, holding it in the box, knowing it was his before even putting it on.

And for Allen, this wasn’t just a random win.

“Oh yeah… this is on my wish list.”

It meant something.

His family felt it too.

“My kids are thrilled for me… because of course they’ll get it in the end.”

A full-circle moment. From buying his first Rolex decades ago, to now winning one he truly wanted.

What stood out just as much as the watch was the experience itself.

“You are so well run. And so transparent… it’s wonderful.”

That trust, especially for someone as cautious as Allen, made the moment even stronger.

From a trusted recommendation, to a few entries, to holding one of the most sought-after Rolex models in the world, Allen’s story came together quickly.

And he’s already looking ahead.

“I’ll be one of your best customers from now on.”

Enrique has lived his whole life in Miami, dedicating his career to teaching middle and high school students. This year marks his final chapter in the classroom before retirement.

And somehow… everything came together at once.

His birthday landed on April 6th.
And just days later, he won the Omega Speedmaster Moonwatch (White Dial).

“Oh man… everything coming together this month. My birthday, the Speedy… it’s literally the Moonwatch.”

For Enrique, this watch is more than just a piece. It goes all the way back to childhood.

“I remember being 8 or 9 years old, watching the moon landing on a black and white TV… this is a full circle moment.”

He’s been part of the Wolf Pack since the beginning.
43 draws. Almost never missing a live.

And the one time he did?

He was working late on lesson plans for his students.

Later that night, he watched the replay… and heard his name.

“I was shocked. I called my daughter and asked if this was real… we were all in shock.”

Enrique has loved watches his entire life. His passion deepened about a decade ago when a friend introduced him to Grand Seiko.

But the Speedmaster always stood apart.

“It’s not about the cost… it’s the story behind it. The Moonwatch.”

From a Swiss Army watch… to Grand Seiko… to dreaming of a Rolex Explorer… and now, the Speedmaster.

“The Speedy is going to be a magical story to tell… an unattainable goal that came true.”

Despite 43 draws, he never stopped showing up. Sometimes with one ticket, sometimes more.

“I’ve never won anything big… maybe $50 once. This is unbelievable.”

Now, he’s counting down the days until it’s on his wrist.

“That’s when the real excitement will start again.”

And maybe the best part?

“My students are going to be excited to hear about this… they’ll probably go home and tell their parents.”

When asked about his experience:

“My experience with WWC, Jory, and Jessie has been great.”

And his dream future draw?

A 100th anniversary Rolex.

For now, though, this moment says it all:

“It’s like walking through a blizzard… and not a single drop touches you.”

Caleb Ribeiro is first and foremost a family man.

A stay at home dad to two young daughters, Caleb has chosen to dedicate his time to raising his girls and being present for every stage of their lives. It is a role he genuinely enjoys, getting to watch them grow up and being there for the moments that matter most.

He got into watches about two years ago and has been enjoying the journey ever since. He spends time watching creators like Jory Goodman on The Time Teller and Teddy Baldassarre, picking up knowledge along the way and simply enjoying the content.

When asked what drew him into watches, his answer was simple.

“For men, this is one of the few pieces of jewelry to wear.”

But for Caleb, it means more than just that.

“I can leave it for my daughters, and they can enjoy it for years to come.”

His journey started with a black Seiko Essentials watch, his first real piece. From there, he moved into more significant watches, including a Grand Seiko GMT with a black dial and red GMT hand, a piece he really appreciates for its precision and design.

Living in an area with limited access to authorized dealers, Caleb has been thoughtful about how he builds his collection. He picked up a Tudor Black Bay 58 from a local dealer, and later, to celebrate their 20th wedding anniversary, he and his wife chose two Omega watches together, an Omega Seamaster 75th Anniversary Summer Blue for himself and a Seamaster Aqua Terra Shades for her.

Caleb discovered Wolf Watch Club through The Time Teller. Both him and his wife decided to give it a try together.

Why not.

Since then, they have entered a number of draws as a couple.

For Caleb, watches are not just about owning something nice. They are about meaning, memories, and having something that can be passed down one day.

Looking ahead, he would love to see the new matte medium blue Rolex Oyster Perpetual featured on Wolf Watch Club.

For now, he continues to enjoy the journey, both as a watch enthusiast and as a dad building something meaningful for the future.