Co-Founder & CEO @ Ruley, the E-Referee | Start Up Business Expert | Entrepreneur

After 25 years building successful companies I found myself at a crossroads. I had built companies that helped people and families. I was proud of that legacy, I knew it was time for a new chapter.

In my early 50s, I sold my third company just a year behind schedule from a personal goal I set at 34. 

During COVID, I had the space to explore ideas that truly energized me. I enrolled in a six-month coding bootcamp to learn Python and deepen my understanding of the technologies shaping our future.

Now I’m the Co-Founder of Ruley, an AI powered smart sports E-Referee API  designed to help federations, sports media and consumer brands gain fans, players and spectators by being the go to venues for sports rules and insights.

My personal mission is to fuse decades of my experience and strategic thinking with modern tech to bring people together through playing sports and watching sports.  By working with these existing sports entities we can grow sports and all the good that comes with them.

At the heart of my work is this belief: we all deserve unbiased, instant information, and we all deserve to enjoy life like we did as kids. 

These ideas aren’t mutually exclusive. With the right tools, we can help provide knowledge in unique ways and inject more joy into everyday life.

Explore Ruley and our API rollout (and more) for sports:
🌐 ruley.ai

📸 Instagram: @ruley_ereferee
🎥 YouTube: @ruleythee-referee
📘 Facebook: @ruleytheereferee

🎾 Just Ruley it!

Cassandra Toroian

First time at the #PGAShow, and yes—I'm sure Tracy Thomas and I will be in the small minority of women attendees as is standard practice at most conferences we attend.

As an introverted entrepreneur, I’m embracing the challenge and bringing my best extrovert game face.

I'm excited because it will be an opportunity to interact with many other #golftech entrepreneurs and golf consumer brands and network for #ruley.

For the Volleybird Athletic Lifestyle team it will be an opportunity to meet and network with racquet sports brands and #hospitality companies that focus on #tennis and #padel who care about being eco-friendly and more #sustainable. 

So...it would really help me out if some of these folks would hit me up before we get there - because I am eager to meet up in person! Assuming you will be attending Teemu Ruuska Kira Peterson Jolyn de Boer Evan Roosevelt Tyler Trout or any other folks that are part of the #profluence community involved in the golf industry!

Please reach out via DM so we can plan a couple of minutes! 😊

Most tennis clubs underestimate how expensive “cheap” tennis balls really are.


The cost isn’t just on the invoice. 

It’s in their reputational cost by not being a leader in the tennis business.

It’s in the the cost to the air their players breathe when out on the court.

It’s the cost of the chemical waste from all those balls going into the landfills.

I’ve spent years as part of sports
organizations, and one business element is
clear. Unfortunately.

Sustainability conversations
stall the moment the cost shows up.

Everyone assumes the environmentally
responsible option must be more expensive.

After all, if all else is equal, we are trained to think sustainable products are always more expensive.

Renewaball | B Corp certified  saw this.

And the decided to make the BEST #tennis and #padel balls available.

That meant the ball had to meet a list of criteria - including wears better, lasts longer, and approved by international federations like International Tennis Federation and International Padel Federation. 

And, by the way,  that also meant making the ball a circular 100% recycled ball.

Now we’re their exclusive U.S. partner!
 
The organizations that win long-term
are the ones willing to question
what “cost” really means.

What “best” really means.

The rest keep throwing balls
away and calling it normal.

If your #tennis or #padel club
or academy, or #luxuryresort wants to be one of the first in the U.S. to be part of the next phase of tennis and padel sustainability, you need to get in touch with Volleybird Athletic Lifestyle the exclusive U.S. distributors for Renewaball.

Supplies are limited.

You’ll need to show your organization is truly concerned with sustainability.

I’ll point you to the right people.


#sports #sustainability #countryclubs #racquetsports #environment #tennis #padel #recycling

Continuing my outbound networking for the #pgashow next week.

I’m excited to be there with Todd Grasley helping us with outreach and networking- not just for #golf and #golftech but with #tennis #padel and #pickleball

We hear this is the biggest B2B event for those sports too! 

I’m excited to hopefully finally meet some folks from racquet clubs and facilities who may be there? Like Marcos Del Pilar - 𝗣𝗔𝗗𝗘𝗟 𝗨𝗦𝗔  Padel Haus PadelBizNetwork Val Goncalves Jr, MBA, RSPA, CDORS, DCA Philippe Azar Carlos Beltran Carlos R. Gonzalez just to name a few.

If any of you are going to be there please DM me I’d love to meet you in person.

And if you’re going for #racquetclub sports and looking to meet new people please DM me as well!

Want to get a different perspective on life in the 21st century and how much technology has changed society?

Inadvertently Tracy Thomas  and I stumbled upon a way to do this and it was easy and truly eye opening.

As GenX we lived before cell phones, apps, wifi, internet, and heck, even before the microwave.

But we forgot what life was like.

So now it’s easy to go back in time.

We chose to travel back through re-watching all 8 years of the series called Melrose Place. A drama/soap opera type show in the mid 1990s.

Here’s what watching it made me realize:
▶️ Life was less complicated without all the technology 
▶️ People interacted in more human ways face to face much more often as a result 
▶️ Clothing styles really have not changed much 
▶️ People used answer machines and called people back when convenient 
▶️ Nights and weekends were actually enjoyed and considered downtime 

Bottom line - life was simpler with less technology.  

Life was lived with more life.

We can’t go back to that, it will never happen.

Particularly now with AI.

But, watching these sorts of tv programs is a good reminder the sacrifices in society we have made by embracing technology.

My hope, and what I strive for, is to harness the good part of AI and technology into a true instrument to bring back more humanity.

More human to human interaction. 

More human joy and happiness.

Not use technology as a means to create a more sterile world. 

There are ways to do this. 

We are doing it with Ruley. That’s our small part.  

Harness sports and technology to create more meaningful human interactions again.

What are you working on that tries to do that? I’m curious.

Share below if you’re willing 💥💥

This is a good little list of “red flags” that can help make the decision to pull the trigger.

My hiring litmus test is easy. 

I ask myself one question.

▶️Does this person clearly know more than I do on the subject matter of the core function of why they are being hired.

So on the backend of that, little things may start to show that are on this list.

But the thing is before pulling the trigger on a disengagement with an employee there’s a second question to answer AFTER observing what’s on this list.

That question is also a simple one:

▶️Is it a fixable behavior? 

After all, shouldn’t they be given the opportunity to step up?

I think really then it becomes a much clearer ending conversation if there’s no improvement.

These functions of being a manager are never easy.

Never pleasant.

But extremely vital to maintain a culture of excellence, respect for the company, and of course, each other.

#SaaS #startups #management #decisionmaking

Open article: Dear SaaStr: What Are Signs It's Finally Time to Move on From An Employee? by SaaStr.ai • 2 min read

Dear SaaStr: What Are Signs It's Finally Time to Move on From An Employee?

I’m building WIN | WIN to be the definitive platform brand at the intersection of sports and social good.

My mission is defined by creating positive change through innovation. At WIN | WIN, we are pioneering NIL for Impact, creating a new blueprint for how athletes, teams, and brands can leverage Name, Image, and Likeness to drive tangible social progress.

Currently, I serve as a Sports Envoy at WorldBoston, exploring how sports can bridge international divides, and as an Entrepreneur in Residence at Tufts University, where I help the next generation of founders build with purpose. My journey is rooted in high-growth impact—from co-founding the digital agency Media Cause, which helped hundreds of nonprofits amplify their reach, to my time as the Director of Program Development for Boston College Softball, where I saw firsthand the power of sports to build character and community.

Now, we are forging a movement where "winning" isn't just about the scoreboard—it's about the legacy we leave behind.

Let's connect if you are:

 - An athlete or agent looking to build an authentic legacy through NIL for Impact.

 - A brand seeking partnerships that resonate with fans on a deeper, value-driven level.

 - A leader in sports or social impact looking to collaborate and change the game.

 - A media professional looking for powerful stories at the intersection of sports and community.

Cody Damon

Looking ahead to a historic era for Boston on the global stage.
I am incredibly proud to share that I have been appointed as the Inaugural Sports Envoy for WorldBoston.

Founded in 1949, WorldBoston is a pillar of citizen diplomacy in the United States. For the past decade, I have had the privilege of serving as a citizen diplomat myself, hosting emerging global leaders through the U.S. State Department’s International Visitor Leadership Program through Bureau of Educational and Cultural Affairs (ECA) of the U.S. Department of State.

Stepping into this Envoy role feels like a natural evolution of that mission.

I am particularly excited to launch the Sports Diplomacy initiative as I support the new co-executive leadership team of Joseph Haynes (CEO) and Sarah Sibley (President & COO). Together, we are positioning WorldBoston to be the primary bridge between Greater Boston’s sports ecosystem and the global stage.

Why Sports Diplomacy? Sports are one of the most powerful drivers of cultural and societal change. Beyond the field, they are a massive engine for economic growth and international cooperation. As our city enters a truly historic era—from the FIFA World Cup™ Boston 2026 and Sail Boston 2026 to the milestone 130th Boston Marathon (Boston Athletic Association), — there has never been a more critical time to explore the intersection of athletics and international relations. Sport provides a unique opportunity for citizens to engage as humans in a world that requires partnership more than ever.

❗ A Call to Action: We are building this program from the ground up and looking for strategic partners. I want to hear from you if:

            🌐  You are a business leader looking at global market expansion via    sports. Or maybe you haven't consider it before and want to learn more.

            🌐 You are a member of the Boston international sports community (athlete, coach, or administrator).

            🌐 You recognize the rich heritage of sports diplomacy in Boston and want to be a part of its future.

Please reach out to me directly or comment below to start a conversation about how we can build this together.

Would love to see a nonprofit jump in on this opportunity. There are so many that could align well between mission and institution. 

What organization would you like to see on a college football jersey next season?

Last night was a powerful reminder of why I do what I do.

I had the privilege of speaking to a group of talented athletes at RSG Hockey. These players are at an exciting, yet high-pressure turning point—navigating the leap to pro or collegiate sports.

While they focus on their game, we focused on their platform.
At WIN | WIN, we believe an athlete’s greatest potential isn’t just measured in stats, but in impact. We work to help them:

 🏒  Identify their core "why."
 🏒  Connect with brands and orgs that align with their values.
 🏒  Turn their athletic success into a vehicle for change.

Thank you to Allain Roy and Tyler Wagner from RSG Hockey for having me. The future of the sport is in good hands—and big hearts.

As we get closer to crowning a college football national champion, there’s a financial war happening that most people aren't talking about. It’s a massive squeeze that’s putting women’s sports and our Olympic pipeline right on the chopping block.

I see this as a "Three-Front War" that is changing everything:

💰 The Debt Tax: Schools are on the hook for $2.8 billion in back pay—money that's being pulled away from current teams to pay for the past.

💰 The $20M Payout: New revenue sharing means millions are going to star players, but it’s often being "found" by stripping the travel and recruiting budgets of other sports.

⏬ The Roster Squeeze: New hard roster caps are essentially "killing the walk-on". While football expands, sports like Women’s Soccer and Softball are being slashed to save on costs.

We’ve already seen schools like Stephen F. Austin try to cut programs like beach volleyball just to balance the books for football—only to be stopped by a federal judge. You can't just "cut your way" to success and ignore Title IX.
The schools that survive this won't be the ones that slash the most programs—it'll be the ones that actually innovate and treat every athlete like an asset, not a liability.

The era of the student-athlete is changing fast. Let’s talk about how we build a system that actually wins for everyone.

The College Sports Commission just rejected nearly 500 NIL deals worth approximately $15 million.

If you think the "Wild West" of NIL is over, you’re looking at the wrong map. 

We aren't seeing the end of the chaos; we’re seeing a massive bifurcation into two competing futures:
  👉  Track 1: The CSC’s audit-heavy world of "Fair Market Value" and "Valid Business Purpose"

  👉  Track 2: The Athletes.org push for a professionalized Collective Bargaining Agreement.

The biggest risk right now isn't just compliance—it’s fragmentation. When every school operates differently, student-athlete development off the field is the first thing to get cut.

We need to codify social impact into the business of sports now, or we risk graduating athletes with a bank account but no professional foundation.

👀 Watch the full video below to see how we’re turning NIL transactions into human transformations.

#NIL #CollegeSports #SportsBusiness #NILi #StudentAthlete Development

The 2026 FIFA World Cup 2026™ - Canada, Mexico and the United States  is no longer just about football; it has become a central piece of the diplomatic leverage being discussed at Davos. 

As the United States and Europe navigate increasingly candid—and tense—discussions regarding Greenland, the transatlantic relationship, and impending tariffs, even the pitch is becoming a site for political messaging.

France’s Sports Minister, Marina Ferrari, recently addressed the growing calls for a boycott from certain political factions: “As it stands now, there is no desire from the ministry for a boycott of this great competition,“ she continued, "Now, I will not anticipate what could happen, but I have also heard voices raised from certain political blocs. I am one who believes in keeping sport separate [from politics]. The World Cup is an extremely important moment for those who love sport.”

As diplomats and trade officials sharpen their rhetoric, the question remains: 

👉🏼  Can a global event of this magnitude truly remain "separate" when the hosts and the participants are at a historic crossroads?

#WorldCup2026 #Davos2026 #Geopolitics #France #Greenland #GlobalTrade #SportsDiplomacy

If you're working with athletes/coaches/admins in the sports ecosystem, at any level, give Jon Lyndon a follow. His insights into how we develop the complete person and just what happens on the court/field/ice are fantastic. 

"The most forward-thinking sports organizations are beginning to understand that player development is no longer purely physical, tactical, or technical. It is also cognitive, relational, and strategic. What is being built here is not a program. It is a philosophy of human development inside elite performance environments."

Open article: Inside an NBA Organization: Why the Toronto Raptors Are Treating Player Development as a Long-Term Human Capital Strategy by Jon Lyndon • 4 min read

Inside an NBA Organization: Why the Toronto Raptors Are Treating Player Development as a Long-Term Human Capital Strategy

It has been a long road, but we're finally here! SIGNING TONY RAYMOND is in theaters nationwide starting today! So excited to get this project out in the world. Please support us if you can, an indie project like ours doesn't have a big window to perform at theaters. If people don't show up the first weekend, there may not be a second. Thank you for getting to your AMC or Regal to check it out!

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