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

Luxury fashion solved resale a long time ago.

Platforms like Vinted proved that worn items can still hold value,
as long as there’s trust, authentication, and a clear marketplace.

What’s odd is how little of that exists in sport.

Sports gear is expensive. Often lightly used.
Sometimes used at elite level. And often tied to real performance history.

And yet once it’s outgrown or replaced, it usually
disappears into general resale platforms
or gets written off entirely.

There are places to sell second-hand gear,
but none that treat it as a category in its own right.

That includes high-value items. Match-worn kits.
Celebrity-used equipment. Limited runs with real demand behind them.

And it also includes everyday players too.
People upgrading clubs. Parents replacing boots.
Athletes moving on.

Fashion resale works because it’s specialised.
Sport resale hasn’t done the same.

Which is strange, given how much value is sitting
unused in garages, lockers, and kit bags.

That looks less like a behaviour problem
and more like an unbuilt market.

Does anyone out there know of a sport-gear focused resale upsale platform?

A conference company offered me the opportunity to meet with potential partners they viewed as very important to the racket sport industry.

But here's the catch:
And they wanted me to pay them a $10,000 fee.
For arranging those 20-minute meeting.

This isn't just bad form. It's bad business.

Alex Hormozi puts it best: "Give information away for free. Sell the implementation."

Business requires graciousness to be highly successful.
A willingness to help others succeed.
Because a rising tide raises all ships.

Short-sighted greed closes doors, whereas graciousness and generosity opens them.

Talking sustainability helps everyone.
How can you demand a price tag on that?
The company requesting that fee has lost my respect forever.

What do you think?

#BusinessStrategy #Leadership #Networking #Graciousness #Entrepreneurship

With the FIFA World Cup 2026™ - Canada, Mexico and the United States coming to the U.S., soccer is entering a very different phase here.

Interest is rising.
International ticket sales are strong.
The reception has been broadly positive.

But amongst many Americans there's a whisper under their breaths…

Only around 12% of Americans say they know the rules of soccer well,
despite the scale of the audience now being built around it.

Soccer is already one of the most nuanced sports to officiate and interpret.
Add a newer audience, unfamiliar terminology, and high-stakes moments,
and confusion scales quickly.

You see it reflected in viewing habits too.
Globally, women’s World Cup viewership exceeds 60%.
In the U.S., it’s closer to 16%.

That gap isn’t about accessibility. It’s about interest.
How can you be interested in something you don’t know much about?

If soccer is to grow in the U.S., rule of the sport
must become part of the infrastructure,
not an afterthought.

Ruley’s API is trained on soccer rules and edge cases with that in mind.
Not as a front-facing product, but as something leagues,
platforms, and media can rely on behind the scenes.

When interest grows faster than understanding,
That gap is where friction appears.

If you work in U.S. soccer leagues or soccer media
and want to explore how Ruley could fit into that
ecosystem, message me.

#FIFA #soccer #USSoccerLeague #USSoccerTeam

Trying a new sport usually doesn’t fail because of interest.
It fails because of uncertainty.

What equipment do you actually need?
Is it worth buying everything upfront?
Will you even use it long enough to justify the spend?

Subscription models can remove that hesitation.

They let people explore new sports without committing to full sets of gear immediately.

That’s the thinking behind Volleybird Athletic Lifestyle’s “mystery box” concept.

Not a novelty purchase, but as a structured introduction.
A way to discover equipment, apparel, and smaller essentials
without overcommitting on day one.

Alongside that, the products themselves are being designed with responsibility in mind.

Materials, fabrics, and suppliers are being chosen with longevity and
environmental impact considered from the start.

The goal is that every item included moves toward
sustainable production as the range grows.

When people can try something new without a large financial
or material commitment, participation becomes easier
and decisions become more intentional.

Discovery works best when responsibility is built into the box.

We went to the PGA Golf Shows expecting to cover a lot of turf. 
And we sure did.

But we also found a massive surprise.

There’s a new wave of golf tech.

My Co-Founder Tracy Thomas and I made incredible contacts with young companies iterating on this historic game.

The "established" sport of gold is actually the very hungry for innovation.

The entrepreneurs understand that to modernize the playing experience, you need modern infrastructure.

Players want real integration between the player, the club, and the rules of the game.

So how do you manage that? How do you merge the tradition of Golf with the speed of innovation?

You need new foundations.
And that includes the Ruley proprietary API.

Ruley is now a new layer of the golf tech stack.

Imagine a golfer getting clarity right there on the course!
About penalty strokes or options to move their ball legally.
No searching through your golf bag for a handbook.
Just playing.

The "old" sports are moving faster than we thought.

The industry is ready.

Whether it's a tech training aid, golf course reservation app, or on course tech, there's something more you can do to help your customer shave points off their game.

DM me if your golf product is interested in learning more. 


#PGAShow2026 #SportsTech #GolfInnovation #RuleyAPI #FutureOfSport #golf

Volleybird Athletic Lifestyle was featured in the New York Post last week.
 
The piece focuses on something tennis rarely questions:
how often balls are replaced,
and how little attention is paid
to their full lifecycle.
 
Renewaball approaches that problem differently.
 
Used balls are collected, broken down, and remade into balls that meet performance standards again.
 
Same role in the game. A more responsible production loop.
 
This approach was built to work within the sport, not around it.
It fits into the sport as it already operates.
The experience stays familiar.
Performance stays consistent.
 
Progress in sport often comes from revisiting everyday equipment,
rather than launching something entirely new.
 
If you’re curious how this works in practice
and why it’s gaining attention now,
The full piece is worth a read here:
 
👉 https://lnkd.in/gT39qKX5

A broken tooth shined a light on what sports (and life) is all about.

Think about it. 

The U.S. Olympic ice hockey team showed unbelievable grit and determination….and sportsmanship.

The young player who had his tooth broken wasn’t upset.

He didn’t blame anyone. 

He was not upset.

It was part of the game. It is just a battle scar.

That’s the different between champions and everyone else.

Broken ribs, torn ligaments. It’s all part of the game. 

Scars show you are battle tested. You are fearless. You can’t be scared into submission.

The Olympians’ scars are a lesson for us all.

Get up everyday. Put on your big girl pants. And fight with no fear for your win.🥇

It's official! Ruley.ai is heading to PEAK 2026 in Las Vegas. 🎉 If you’re working in SportsTech, innovation, or sport operations, this is where the industry comes together. Let’s connect. April 20–22, 2026 | Fontainebleau Las Vegas. See you there. 🏔️

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

Indy brought the energy for the first-ever NCAA Legacy Lab! 

The week was packed with opportunities for student-athletes to explore their own blueprint for leadership. My focus with was showing these student-athletes how to build with purpose as they ready themselves for the next phase of life post-graduation.

We dove into the WIN | WIN NILi model, exploring how to use their massive platforms and NIL opportunities to advocate for the issues they care about most. It’s about creating an impact that resonates way beyond the final whistle.

Huge thanks to the Ashley Jocelyn and the NCAA Leadership Development Team for the invite and for creating a space where athlete influence is treated as a force for good. 

To the athletes: Y'all brought it and I was proud and honored to be apart of the journey. As always it was a situation where I learned just as much from you because of your creativity, courage and trust. Your legacy is officially under construction. 🏗️

Can't wait to see what you build. 

#NCAALegacyLab #WinWin #NILi #StudentAthletes #BuiltToLast #NIL

Student-Athlete Human Development, Boston Sports Envoy, EIR @ Tufts

I spent this past week in DC, and if I had to summarize the trip in one word, it would be intentionality.

I was there wearing a couple different hats:

With my WorldBoston Sports Envoy Hat: Meeting with Meridian International Center to map out a partnership for what elevating sports diplomacy looks like for two world-class sports towns. We’re focused on amplifying the global impact of sports diplomacy—using the universal language of play to build international bridges.

With my WIN | WIN beanie on: Meeting with leaders in the social impact and collegiate NIL space. Our mission is clear: helping student-athletes leverage their platforms for opportunities that will sustain them long after the final whistle blows.

But the what stood out the most wasn't a particular meeting - it was a vibe. 

Seeing the impact the Leonsis family and the Monumental Sports & Entertainment team have on DC is a revelation. From hosting the  GW Sports Philanthropy Summit at District E to ensuring every single public school student in DC had a basketball in their hands, their model is not just working, it is thriving. They're winning championships, they're building a massive business, and they're making their community better at the same time. 

It is the ultimate proof of concept for everything we are building at WIN | WIN. Purpose and profit aren't in competition—they are fuel for one another.
When we lead with intentionality and treat our teams, our athletes, and our communitiew with genuine care, everybody wins.

Grateful for the examples being set in our capital and more fired up than ever to keep building at this intersection of sports and purpose. 🏀🌍
#SportsDiplomacy #NIL #SocialImpact #SportsBusiness #WinWin #MonumentalSports #Leadership

Photo taken from a Lime Scooter. The best and only way to travel in DC.

The last 10 days, I've been a road dog. DC, Indy, SF

It's been great to hit the road and meet with folks with my WIN | WIN founder hat on and my Sports Envoy for WorldBoston hat on.

As I packed again for a quick trip down to NYC, I started thinking about what a sports diplomat actually looks like.

Usually, the image is a suit and tie in a marble building in DC. Those who know me, know that's pretty far from my daily fit. My day-to-day might still involve those wood panel rooms of DC, but it could also be the office of a head coach or a co-working space to meet partners. My meetings don't happen in three-piece suits—they happen in a crisp pair of sneakers and a fitted hat to keep my bald head out of the elements.

👉  So what is the "uniform" of sports diplomacy? 👈 

Boston is such a massive global sports hub, and with the 130th Marathon and the World Cup coming in 2026, we’re about to be the world's host. If sports is the universal language, I think the gear we wear needs to reflect that. It’s a mix of local grit and international influence. It’s approachable, functional, and carries the DNA of the city.

I’m curious what you all think. If you’re representing your city to the world, are you reaching for a blazer or a premium hoodie? Can a pair of kicks carry as much diplomatic weight as a briefcase?

Last week I shared a $50k, entry level role for an inspiring entrepreneur looking to get some hands on experience supporting the different work that I am doing at the intersection of sports, social impact, and international relations.  

I had zero candidates. I took out an ad using Linkedin. I had zero candidate that read the requirements. 

Later this week I am headed to DC for the the GW Sports Industry Networking Conference where there will be hundreds of undergrads and grad students looking to "break into sports". 

Where are these eager professionals in Boston?

https://lnkd.in/eBn8h-CA

Executive Assistant (Founder-in-Training)(CONTRACT) Location: Greater-Boston Area (Hybrid) Focus: Sports Ecosystem & Social Impact Salary: $50,000 The

Open article: [JOB] Executive Assistant (Founder-in-Training)(CONTRACT) by Cody Damon • 3 min read

[JOB] Executive Assistant (Founder-in-Training)(CONTRACT)

Tried to find the most Irish thing I could do in Boston for St. Patrick's Day. 

It had to involve green, of course. It has to be a cathedral to Irish culture and history. It also needed to be something that made me feel hopeful for the future.

Where did I end up? Fenway Park, as the Irish Government unveiled their 5 year plan for integrating Sports Diplomacy into their wider foreign policy. 

Fun fact: Fenway Park was built by Irish immigrant Charles Logue from County Derry, Ireland. Ground was broken on September 25, 1911, and the Charles Logue Building Company completed the structure in time for the opening game on April 20, 1912. (Not who we hired for the Big Dig)

#SportsDiplomacy #Ireland #Boston

Nothing beats a conversation that validates your "why" while challenging your "how." Huge thanks to Tracy Hughes for the sharp insights today—we’re doubling down on our nonprofit outreach strategy and moving faster than ever to create meaningful and impactful NIL of Impact opportunities for student-athletes. 🙏🏼

Alexis Ohanian Sr. is spot on about the "bottom line" in women's sports being a massive, untapped business opportunity.

But as a social impact founder, I keep looking at a different set of numbers. We have hundreds of thousands of student-athletes (44% of them female) in the NCAA system who are essentially high-performance leaders in waiting, yet most graduate without a clear "exit strategy" for life after the game.

NIL has changed the cash flow, but it hasn't solved the human development piece. That’s the gap we’re obsessed with at WIN | WIN.

We’re building a way to use AI to actually scale human outcomes—not just tracking stats on the field, but mapping an athlete’s unique DNA (resilience, leadership, high-stakes decision making) to their professional life post-graduation.

It’s part of our NILi (NIL for Impact) model. We want to move the needle from just "collecting a check" to building a career foundation.

If we can use tech and NIL opportunities tied to issues student-athletes care about, then we can turn every student-athlete into a high-impact leader ready to tackle the challenges we face ahead. The ROI isn’t just in the sports world—it’s everywhere.

We’re starting to tease out some of the tech we’re building behind the scenes right now. If you're in the sports-tech or human capital space, I’d love to hear your thoughts on how we bridge this gap.

Thank you, Sports Illustrated! I feel so blessed that my second chapter (life after Reddit) would get so big, so fast, and most importantly — be so damn fulfilling. I'm very proud my daughters get to see me building this legacy in women's sports and beyond, especially in the AI revolution, sports will only get more valuable because we can't replace the humanity on the pitch, track, court, etc.

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