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?

Founder @ Block On Ventures. Investor, Accelerator, Venture Builder, Speaker . Blockchain, Crypto , Web3.0 and AI. " Do not pitch for any physical product business at all."

Founder of Block On Ventures. We specialize in accelerating startups within the blockchain and emerging tech sectors. 

Our commitment has been unwavering over a decade, fostering a dynamic ecosystem where innovation thrives. 

As an early-stage investor, i look forward to transform the landscape of Real World Assets, creating a more accessible and efficient market. Our collaborative approach with government agencies and industry leaders in the ASEAN region amplifies our impact and drives progress within the blockchain community.

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Cassandra Toroian's LinkedIn Performance

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