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

Most people still think Ruley is “that sports rules app.”

And sure, that’s where we started.
Because the fastest way to prove accuracy is to
Put it in someone’s hand.

Let them test it.
Let them see it works.
Let them try to break it.

The app was never the endgame.
It was the demo. What we’re building now is
bigger. Much bigger.

APIs.
The quiet engine behind every great product.

That’s where Ruley belongs.
Because if you want to transform sports at scale,
you don’t build another app. You build the
system everyone else can plug into.

Sports apps.
Sports Websites,
Equipment manufacturers,
Sports Federations,
And so, so many more.

Emerging sports trying to standardize their rules.
Recreational programs that need consistency.
Even niche sports nobody’s ever heard of yet.
That’s where the impact lives.

We realized that if we wanted Ruley to actually
fix the rule-accuracy problem, we had to stop
thinking just about players first and start
thinking about the entire ecosystem.

So we pivoted. On purpose. With clarity.
Ruley IS designed and developed
to sit inside any sports related platform.

It’s an API designed to sit inside
any sports platform, anywhere.
Instant rule explanations.

Unbiased.
Consistent.
Sport-agnostic.

This solution grows fans, spectators
AND player knowledge.

This is how you cultivate the next generation of players and fans

We are becoming the rules sports engine infrastructure

We started small so we could prove we were right.
Now we’re expanding so every sport can benefit.

If your platform needs clarity, plug us in.
Fair play starts here.

We can't clean the ocean, but AI can.

Not someday.
Now.

The Ocean Cleanup uses AI-powered sensors
to spot where debris gathers..
Then directs cleanup vessels straight to it.

No wasted time.
No wasted effort.

It’s already happening off Florida’s coast,
Where every current brings back what we’ve
thrown away.

Bottles.
Bags.
Microplastics.

AI is doing what we should have done
tracking the damage,
and fixing it.

Not to make headlines.
To make progress.

Because real innovation isn’t about noise.
It’s about outcomes.

If AI can clean our oceans,
Imagine what it could clean up next
If we pointed it at the right problems.

The tech isn’t the challenge anymore.
The intention behind it is.

What ChatGPT gets wrong about sports rules.

Here’s a fun experiment.
Ask AI a niche tennis rule.
Wait for the confident wrong answer.

I tried it this week.

My question:
“I accidentally double hit in tennis. Do I lose a point?”

ChatGPT’s answer:
“No. Any double hit is an automatic point loss.”

Sounds firm.
Sounds correct.
And it’s completely wrong.

Here’s the real rule:
If the ball hits your racket twice in one
continuous motion, unintentionally,
It’s legal.

The only time it’s illegal is:
If the player intentionally hits the ball twice.

Unintentional double contact, which is what actually
happens in real rallies, is allowed.

This is straight from the ITF rules.
One tiny detail. Massive difference.
 
And this is the bigger issue with AI in sports:
It predicts common answers.
It doesn’t understand nuance.
It doesn’t know how players actually argue on court.
It doesn’t know the rules the way the sport requires.

Sports don’t run on “close enough.”
They run on precision.

And this is exactly why Ruley exists.
Not to replace humans. But to replace confusion.
Sports deserve better than “close enough.”

What would it feel like to play tennis If you were color-blind?

Would there be a struggle with depth perception? 
To follow a game where the lines
And the ball looks the same shade?

VR technology is now letting athletes experience
exactly that. Simulating visual impairments in real time.

It’s confronting.
Because once you’ve felt the limitations,
You start to question how the game is designed,
and who it truly includes.

That’s where technology can shift the conversation.
Not to replace sport, but to expose blind spots
in how we design it.

If AI or VR can help athletes, coaches, and officials
understand those perspectives,
It doesn’t just build better tech.
It builds better empathy.

And maybe that’s what the next era of sport looks like..
one built on awareness as much as performance.

Such a fun time on this podcast episode with Tracy Thomas and host Bryan Fetzer

Sports Personality - Inspire / Lead / Succeed

DO YOU LIKE PICKELBALL?
Got your attention?

Curated gear that actually makes your weekend run smoother? Yes, please. 👀
On Just A Cup, I sat down with Volleybird Athletic Lifestyle founders Cassandra Toroian and Tracy Thomas to talk building a sports-lifestyle brand (tennis, pickleball, padel, golf) and their sister venture Ruley, an AI “E-Referee” that ends the rules debates before they start.

We cover: founder lessons, product curation, community feedback, and turning rec play into a real movement.

Watch/subscribe on YouTube: https://lnkd.in/eHQE4X65
Listen on Bleav: https://lnkd.in/gPQKEy8j
Episode page: https://lnkd.in/eF7rqeHh

Learn more about Volleybird https://volleybird.shop/

#Volleybird #SportsTech #SubscriptionBox #Pickleball #Tennis #Padel #Golf #WomenFounders #JustACup #Bleav

If it hits the kitchen line it’s out… right? Or is it in?



That’s always a big controversy,
especially in college pickleball.

But Brooke and Ava from
University of Miami use
Ruley, the E-Referee
So they don’t worry!

And when Brooke’s parents play,
it stops those classic “I know best”
moments that cause family feuds.

Rules made simple with our
proprietary API, so your players
can play on and enjoy the game.

#JustRuleyIt

Thanksgiving football isn’t just a warm living-room ritual. It’s a tradition steeped in real history and it teaches us something about the power of rules, legacy, and how things become meaningful over time.

Here’s the origin story:

The first college football game on Thanksgiving was in 1876, when Yale beat Princeton, 2‑0, in Hoboken.

By the 1880s, that annual matchup had become a major social event, with thousands of fans gathering in New York City.

But the modern NFL Thanksgiving tradition really took off in 1934, when the Detroit Lions hosted the Chicago Bears in a nationally broadcast game.

That wasn’t just a game, it was a masterstroke of promotion. The Lions’ owner used his radio connections to make Thanksgiving football a national spectacle.
 

Why does this matter, especially if you care about more than just touchdowns?
 
1. Tradition is not born, it’s built. What started as a college holiday game became a cornerstone of professional football through deliberate vision, not accident.

2. Legacy amplifies value. The Lions’ Thanksgiving move wasn’t just about selling tickets, it was about building identity and a long-term franchise reputation.

3. Clarity of rules matters. Football may feel chaotic, but traditions like these survive because there is a shared understanding, and respect, for how the game works. That very principle is why technology that clarifies rules (in sport or business) can be so powerful.
 
As someone who builds in the space of sports clarity, I find this intersection, history, tradition, and precision, endlessly inspiring.

What part of Thanksgiving + football tradition is most meaningful to you?


#Thanksgiving  #NFL  #Tradition  #SportsHistory  #Leadership

My recent trip to the airport was shocking.

Apparently there is a trend where some people purposefully dress inappropriately when air travelling,

Why?

From what I surmise it’s because they want to actually cause a problem or create a scene in the hopes maybe the get kicked off a plane.  

Then they can file a lawsuit. And maybe the airline writes a check!

This seems to be another example of how society has degraded.  

It’s not ok. 

Particularly since the intent behind this choice to wear an outfit that borders on socially unacceptable is to MAKE havoc.

This has to stop. 

But how does it stop when clearly so many aren’t getting taught some basic social norms?

Fortunately we have an administration that has some cajones and recognizes that some helpful hints in civility may have to be part of their job.

They put out a statement encouraging people to dress appropriately for air travelling and not show up at the airport in night clothes.

It causes disruption. It causes delays. It causes rage inside planes and people get kicked off.

We used to be a society where people would tell their neighbor or friend they looked funny, remind them to take off their cap when they go to a restaurant.

This is just yet another example of the degradation of rules in society - rules that are mean to help keep some basic order. Tradition perhaps. But also it just works.

Sad that the government has to give this basic advice. 

If you don’t like that, then please, feel free to be a good neighbor or friend and start gently point out things that you see.

Do it in a nice way. 

Do it in a helpful way.

But do it.

We all have to be part of re-elevating civility in our society again.

Do you agree?

Here’s what I heard this morning when I listened to the snow fall.

This song went through my mind. 

Because I know in two days a company I co-founded called Volleybird Athletic Lifestyle is launching a product here in the U.S. that will be game changing.

For the sports of #tennis and #padel.

So to me it feels like a combination of Christmas Eve and this song. 

The future is so bright I gotta wear shades.

If you’re in the #sports #tennis or #padel industries and want to get our announcement DM 💬me your email address and we’ll add you to the list.🔥

Open video: Timbuk 3 - The Future's So Bright I Gotta Wear Shades Lyrics on youtu.be

Timbuk 3 - The Future's So Bright I Gotta Wear Shades Lyrics

Someone asked where I learned to be resilient.



Resilience doesn’t just happen.
It’s trained through experience.

Was it through sports? Or from
growing up as an only child?
For me it was both.

When you playing solo sports
you learn early that no one’s
coming to rescue you.

→ You problem-solve.
→ You stay resourceful.
→ You make things work.

Sports simply reinforced it.

In tennis or golf, there’s no one
to hand off the pressure to.
It’s just you, your decisions, and
how you respond to setbacks.

That mindset stayed with me for life.
Through building and selling several
companies, and now through building
something completely new.

I’ve learned resilience isn’t about
pushing harder. It’s about adapting.
Seeing patterns, solving problems,
and moving forward even when the
rulebook hasn’t been written yet.

There’s a strong link to resilience
and innovation, they’re two sides
of the same coin.

Right now, as I always have been,
I’m learning the rules and then
redefining how they’re played.

What about you?

Do you see yourself as resilient?

The future of sports tech isn’t standalone. It’s integrated.


For years, the sports technology world
has been driven by the same playbook:

→ build another app,
→ build another platform,
→ build another way for fans to “engage.”

But innovation has never meant
building something completely new.
It means taking what already exists,
and improving on it in a way that people
think “why hasn’t this always existed?”

Look at Airbnb. They didn’t invent hotels.
They invented a way for people to earn
money from renting out their own space.

Look at Uber. They didn’t invent taxis.
They invented a way for people to get a
taxi really conveniently, from anywhere.

Look at Ruley, the E-Referee. We didn’t
invent another tech product competing
for attention. We created Ruley as the
connective tissue that strengthens
the entire ecosystem of sports itself.

Our proprietary API integrates directly
into existing tech, apps and systems,
making it easy for organizations, fans,
and players to understand in real time.

Just like Uber integrating with your cell
and Airbnb integrating with your home,
the future of sports tech is integration.

When people understand the rules,
they’re connected, confident, and loyal.

→ For our partners, that means higher trust.
→ For their users, it means a better experience.
→ For the industry, it means progress that scales.

Ruley’s mission was never about
being the next big sports app.

It’s about being the trusted layer
of intelligence powering fairness
and understanding across sport.

That’s what real integration looks
like, and why the future of sports
technology will be built together.

Do you agree?

Or are we better off with 100’s
of independent systems?

WIN | WIN

At WIN | WIN, we're redefining what it means to win in sports. We're taking the passion from the field and channeling it into real-world impact. We amplify the most powerful stories of sports philanthropy, building a vibrant culture around athletes, teams, and fans creating positive change. Starting as a content hub, we're becoming the go-to brand for sports and social good – a platform that doesn't just tell the stories, it helps make them happen. Get ready to witness a new era of impact, driven by the power of sports.

Founder

Derby Entrepreneurship Center at Tufts University (DEC)

The Entrepreneur-in-Residence (EIR) program is a pilot program where we bring in practicing innovators and entrepreneurs with subject matter expertise in new venture creation to coach, mentor and create innovative co-curricular programming for students, presenting them with a practical perspective that is deeply in tune with the EIR’s own work outside an academic context. EIRs helps educate, mentor and coach Tufts students across campus on the realities of being an innovator and entrepreneur in any setting – startup, corporate, non-profit, government and more.

The EIR with Community Focus shall not only help students learn how to become entrepreneurial leaders, but will also act as a personal ambassador for innovation and entrepreneurship among a diverse set of student groups, building awareness for learning experiences and collaborating with student leaders to bring these learning experiences to student groups that are historically under-represented in entrepreneurship education at Tufts

Entrepreneur In Residence

Outfield Apiaries

Founder and Chief Buzz Officer

2nd Half Advisers

For Founders
Our Strategic Growth Planning services empower your business with a clear roadmap for scaling, identifying key milestones and growth levers. We refine your target audience and value proposition through market analysis and customer segmentation, and optimize your pricing strategies for maximum profitability. Our Operational Efficiency & Optimization services streamline processes, improve efficiency, and implement systems and tools that support scalability. We focus on building and managing high-performing teams, while providing robust financial modeling and forecasting. Finally, our Sales & Marketing Strategies help you develop and implement effective plans, build brand awareness, and acquire new customers.

For Startups
We empower early-stage founders through a comprehensive suite of services tailored for bootstrapped ventures. We guide you through lean startup methodologies, validating your ideas and ensuring product-market fit. Our financial planning expertise helps you optimize resources, implement effective bootstrapping strategies, and achieve sustainable growth. We equip you with growth hacking and marketing techniques to maximize your reach on a budget, and refine your sales processes for optimal customer acquisition. Additionally, we support team building, culture development, and provide the mindset coaching necessary for navigating the challenges of entrepreneurship.

Media Cause

A mission-driven marketing and creative agency that helps nonprofits grow and accelerate their impact. We take a people-first approach to developing powerful creative, scalable growth strategies, and targeted communications that connect with individuals across their entire supporter journey: from awareness and recruitment to fundraising and advocacy, and every touchpoint in-between.

Co-Founder

The American University of Paris

Lecturer

DSConsulting (acquired by Media Cause)

Damon Strategic was a boutique digital marketing agency that focused specifically on the nonprofit sector. After 8 months, 12 clients, and a great deal of sweat equity is was rolled into what is now Media Cause.

Principal

Common Sense NMS

Senior level position created to oversee agency's transition into social media. Function as point person for agency's presence across various social media channels. Cody works with some of the leading progressive causes in the world. His ideas and project management have spawned actionable change for partners such as (RED), NRDC, San Francisco Ballet, Vanity Fair, Cornell Lab of Ornithology and Human Rights First.

* Analytics benchmarking, measurement, and analysis of data from digital properties, including web analytics, social media channels, and advertising platforms.
* Senior project management: concept creation, channel & platform mechanics, metrics measurements, analysis, and reporting.
* Creation of internal agency processes and oversight to ensure highest levels of profitability and client satisfaction. 
* Train junior account executives on best practice techniques for Google Grant management, Facebook social ads, metrics monitoring and analysis, content creation and curation.  
* Maintain solid relationships with industry leaders at Facebook, Twitter, Foursquare, and Google to ensure first notification of new products or platform changes. 
* Maintain agency blog highlighting current projects and industry analysis and news.

Director of Digital Strategy

Aedi Group

To aid the portfolio of companies with communication and web 2.0 strategies. 
Duties will include:
* Research and development of potential partnerships with NGOs, businesses, and government
agencies in South Africa
* Communication and web 2.0 strategies with NGO's, businesses, and government agencies.
* Communication and web 2.0 strategies to enlist volunteers to learn about and contribute to
Village Corps to prepare for future growth.
* Development of content for the Web site and supporting materials
* Developing strategies around email campaigns (a combination of advocacy and marketing).

Marketing Manager

ATLANTIC RESEARCH AND CONSULTING

Trained, supervised and motivated a team of up to 12 employees in preparing and processing digital imaging and other files for market research purposes. 
* Compiled, proofread and distributed content seamless, error-free execution of all initiatives. Delegated responsibilities for multiple simultaneous projects.
* Expertly managed time and resources, meeting 100% of deadlines in fast-paced setting.
* Promoted to supervisory position within eight weeks of start date.

Program Supervisor

Cody Damon is the driving force behind WIN | WIN, a venture poised to redefine sports philanthropy. His journey, marked by co-founding Media Cause, a transformative agency that empowered hundreds of nonprofits to harness digital media for social impact, underscores his deep and sustained commitment to creating positive change. His tenure as Entrepreneur-in-Residence at Tufts University continues to significantly fuel his passion for cultivating innovation and guiding aspiring leaders in the realm of social enterprise. As Director of Team and Program Development for Boston College Softball, he gains invaluable insights into the profound influence of sports on community and individual growth, a vision now powerfully realized in WIN | WIN.

At WIN | WIN, Cody champions a new culture, amplifying the most compelling stories and pivotal moments where the worlds of sports and social good intersect. He is building the world's largest content resource dedicated to this vital space, ensuring these impactful narratives reach a wider audience. The vision extends beyond content curation; WIN | WIN is evolving into a dynamic media and lifestyle brand, actively facilitating tangible impact. They are forging innovative pathways for athletes, teams, and fans to unite for meaningful moments that extend far beyond the playing field.

Cody's commitment to creating a better world resonates beyond his entrepreneurial endeavors. He actively fosters global understanding and collaboration as a Citizen Diplomat and supports the development of young leaders and athletes through his youth coaching roles.

With WIN | WIN, Cody is not just changing the game; he is redefining what it means to win in sports. This is a movement to amplify the good, celebrate the moments of positive change, and build a future where sports truly wins for everyone, creating a lasting legacy of impact.

Cody Damon

The future of sports will be built by those who are willing to collaborate across traditional silos—bridging media, purpose, brands and the game itself.

Excited to announce I'm an early member of Arena's Founding Circle, a truly curated platform connecting the most strategic leaders in sports, media, and entertainment.

This platform isn't just about networking; it’s a critical resource for fueling the growth of the WIN | WIN ecosystem. The next wave of value—the kind that moves beyond the scoreboard and into purpose—comes from making these high-level connections. I look forward to leveraging this network to discover new NILi (NIL for Impact) opportunities.

If you’re a leader focused on building, impact, and driving revenue, this is where you need to be. Highly recommend applying before spots close.

Applications are still open (limited spots): arenatalent.com

Who from the WIN | WIN network is joining me to build what’s next? #SportsBiz #NILforImpact #Innovation

Next week we'll share the latest Beyond the Scoreboard podcast we recorded on-location at The Post Clubhouse in NYC. This was the first time Amy Small and I took the show on the road!

Big thank you to Christian Ponder for letting us crash his Gatsby-themed holiday party, but also for the candid discussion. We had a chance to talk about the chaos of entrepreneurship, building structure for athletes transitioning away from competition (at least on the field), and how 'understanding your why' helps with that shift.

We'll be posting the episode next week. Stay tuned! #BeyondTheScoreboard #Entrepreneurship #AthleteTransition"

The past couple of months have been a whirlwind at WIN | WIN and I've been a little quite "building out loud". But the reality is, sometimes it's really hard to keep up with talking about doing the thing, when you're too busy doing the thing. 

Lots of great announcements on the horizon. Coach Hurley has the vibe. 


https://lnkd.in/ezGFCqVr

Open video: You better get us now on youtu.be

Michigan State University is looking to raise $1Billion for athletics. In fact, it has already raised $250Million from donors. No, details on a timeline for the largest capital campaign in school history, but it won't be the first time a school athletic department has gone after this amount of money. The The University of Texas at Austin has done it, Texas A&M University raised more than $900Million back in 2021. 

No hot take here. More just questions... (1) How long are donors going to support initiatives at this level? (2) Is there where we see private equity come in and fill gaps? (3) If so, is that good for college athletics? (4) Where do student-athletes come into this dynamic of even more money entering the fray?

Open article: Athletics Department Launches FOR SPARTA: The Capital Initiative for MSU Athletics - Michigan State University Athletics by msuspartans.com

Athletics Department Launches FOR SPARTA: The Capital Initiative for MSU Athletics - Michigan State University Athletics

Whenever I need a midday pick-me-up Harry Mack is the solution.

You won't find a more gifted and uplifting lyricist. 4-5 minutes of pure joy.

Student-athletes today are ready to engage with real issues, making their authentic voice the most valuable commodity in sports marketing.

How big is this opportunity? The first person I wanted to chat with was NIL expert Bill Carter, "A year ago, I did a study and found these issues, and the percent of student-athletes that cared about the issue, to be these: 
 - Mental Health: 87%
 - Education Affordability: 86%
 - Diversity, Equity, and Inclusion: 77%
 - Gun Violence: 69%
 - Racial Justice: 54%
 - Climate Change: 47%
 - Income Inequality: 40%
 - Healthcare Access: 33%
 - Reproductive Rights/Abortion: 30%"

Why is this data critical for your brand?
This widespread passion represents a critical shift and a massive, untapped opportunity for purpose-driven NIL partnerships. Traditional sports sponsorships are simply not an option for many emerging brands, often costing between $500k and $1M+. The NILi (NIL for Impact) model changes the equation entirely.

Instead of taking a high-risk bet on a single athlete, you can build a stable, diverse team of student-athletes. Instead of relying on short-term product endorsements, you can create year-round, authentic narratives.

By centering your sports-marketing strategy on student-athletes who are genuinely passionate about a cause, you tap into a golden advantage: their authenticity directly enhances your brand's perception and builds strong affinity.

Open article: The Untapped Power of Purpose: Why Your Brand’s Next Big Win is in NILi by thatsthewinwin.com

The Untapped Power of Purpose: Why Your Brand’s Next Big Win is in NILi

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The Battle

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Likes

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