Chapter 01
Central Illinois roots
My story starts in Central Illinois. That background shaped how I think: practical, work-focused, relationship-driven, competitive, and willing to figure things out by doing the work.
About Ryan Knuppel
Most people call me Knup.
I’m an entrepreneur, husband, dad, former basketball player, builder, and systems thinker. I’ve spent my career building businesses around sports, media, technology, relationships, and family.
This page is less about a company pitch and more about the journey that led me here.
Ryan Knuppel
Entrepreneur. Builder. Family-first operator.
The short version
I think in ecosystems, not isolated businesses.
I grew up in Central Illinois and took the traditional path after college. I got a job at Caterpillar, a Fortune 100 company, and spent 15 years there while slowly building side hustles at night, on weekends, and whenever I could find the margin.
Those years taught me a lot. They taught me discipline, frustration, patience, and the difference between having a job and building something that felt like mine. I did not know exactly where the online business path would lead, but I knew I wanted to build.
Eventually, writing sports content on the side turned into something real. Sports affiliates needed content. Websites needed traffic. Operators needed people who understood sports, betting, content, SEO, and execution. I figured out that “this was a thing” before it was obvious to everyone else.
Before the business
Sports shaped almost everything.
Long before Knup became a business ecosystem, sports were the center of my life. Basketball was the first real arena where I learned competition, confidence, leadership, pressure, preparation, and how much work it takes to be good at something.
I was an All-American basketball player at Division III Elmhurst. That part of my life still shapes how I think about business. I like teams. I like systems. I like preparation. I like the pressure of the game.
Some of the stories still sound a little ridiculous when I say them out loud: playing basketball against Michael Jordan, playing flag football with Deion Sanders and Jerry Rice, and winning a FanDuel NBA contest that sent me to the Playboy Mansion for a live final. They are fun stories, but they also explain why sports has always been more than entertainment for me.
The Journey
From Central Illinois to full-time online business.
Chapter 02
The traditional path
Right out of college, I went to work at Caterpillar. On paper, it was the responsible path. In reality, I spent 15 years knowing I was not wired to stay there forever.
Chapter 03
The side hustle years
While working full time, I started writing for sports affiliates and experimenting with websites, domains, fantasy sports, betting content, and online projects. Those side hustles became my real education.
Chapter 04
Going all in
When I had the chance to take severance and leave Caterpillar, I jumped. By then, I had already spent years dabbling, testing, writing, building, and learning. I was not starting from zero. I was already a pro before I went full time.
The sports betting boom
Then the market moved, and we were ready.
After leaving Caterpillar, the work came fast. I brought my brother in to help with writing. Then we needed more writers. Then more. Then even more.
When the U.S. sports betting legalization boom hit, we were in the right place at the right time. Sports 2.0 Network and related projects exploded. At one point, we had 100+ writers producing 125+ articles per day across the network.
That period gave me a front-row seat to content operations, affiliate marketing, media growth, partnerships, SEO, team building, systems, and the pressure that comes when growth actually works.
15
Years building on the side
10+
Years full-time online
100+
Writers at peak scale
125+
Articles per day
The next shift
AI changed the content game. So I started building again.
When AI arrived, it was clear the content business was going to change. Instead of pretending it would not happen, I leaned into it. That became Coded Content.
Coded Content combines sports data, automation, AI, templates, and editorial systems to produce content at scale. It is not just about articles. It is about building repeatable content infrastructure.
That shift also helped clarify what I enjoy most: not just creating content, not just building websites, but building systems that help people and businesses execute.
Today
Knup is the headquarters for what I’m building now.
Knup connects the businesses, projects, relationships, and assets I am building across sports, education, media, real estate, technology, content, and entrepreneurship.
I still love building. I still love side hustles. I still love domains, ideas, systems, and opportunities. But now I am more focused on building things that compound: recurring revenue, useful systems, strong relationships, owned platforms, and long-term freedom.
The family layer
Business should support life, not consume it.
My family is a major part of why I build the way I build. Sarah, Drew, Bryce, and Alyssa are not separate from the story. They are a big reason the story matters.
The long-term goal is not to build one giant company that owns my life. It is to build a connected portfolio of businesses, assets, relationships, and systems that create freedom, recurring revenue, meaningful work, and more time together.
Sarah
Ideal Homeschool, operations, education, family experience, and client support.
Drew
Sports Mentorship, athlete mentorship, leadership, and the next generation of the ecosystem.
Bryce
Baseball, golf, growth, competition, and a daily reminder of why sports and family matter.
Alyssa
Track, independence, family, and another reason to keep designing life intentionally.
The 2027 vision
The next chapter is location independence.
Central Florida is home, and I am continuing to build here through Knup, real estate, business relationships, and the broader ecosystem. But the long-term vision has always been bigger than staying tied to one location.
The goal for 2027 is not retirement. The goal is a slower, more flexible, location-independent lifestyle where the businesses can travel with us, the systems are documented, and the work supports family experiences instead of blocking them.
That is why I care so much about recurring revenue, automation, simple systems, owned platforms, remote delivery, and building businesses that do not require constant in-person management.
Remote Systems
Businesses that can operate through documented processes, cloud tools, automation, and clear ownership.
Recurring Revenue
Subscriptions, retainers, memberships, hosting, and predictable income that create flexibility.
Family Experiences
More time, more travel, more flexibility, and more shared experiences without stopping the work.
Passions, stories & side quests
The fun stuff matters too.
Some of the best parts of the journey do not fit neatly into a business bio. These are the stories, interests, hobbies, and side quests that make Knup feel like Knup.
Basketball
Playing basketball against Michael Jordan
A future story about one of the more surreal basketball moments of my life.
SportsFlag football with Deion Sanders and Jerry Rice
A future story from one of those “how did I end up here?” sports experiences.
Fantasy SportsThe FanDuel NBA contest and Playboy Mansion trip
A future story about winning a FanDuel NBA contest and earning a live final trip.
LifeGolf, country music, cards, concerts, and side quests
Golf with the boys, country music pit experiences, collecting, reselling, domains, and the hobbies around the edges.
What I believe
These ideas show up in almost everything I build.
Simple systems beat complicated stacks.
Tools are useful only when they reduce friction, create leverage, or make execution easier.
Relationships compound.
The right relationships create referrals, partnerships, opportunities, trust, and long-term value.
Execution teaches more than planning.
Build the useful version, put it in the real world, and improve from there.
Ownership matters.
Own the website, audience, systems, domains, content, data, and relationships that power the business.
Recurring revenue creates freedom.
Predictable revenue gives families and businesses more room to make better long-term decisions.
Business should support life.
The goal is not more complexity. The goal is more freedom, more impact, and more time for what matters.
Contact Ryan
Want to connect?
Reach out if you want to talk business, partnerships, websites, systems, sports, content, real estate, homeschooling, media, or building life a little differently.
Share your name, email, and message through our short contact flow.
Send a Message