My story

Built. Broken. Rebuilt. Still Building.

35+ years. Multiple companies. One cancer diagnosis. One complete reinvention through AI.

Two paper rounds. Three jobs. One house. One divorce. One plane ticket to New York.

One Ducati flagship. One co-founded dealership. One brutal second divorce. Fourteen years without my son.

One agency built from a garage floor. One VP role I walked away from. One cancer diagnosis.

One reinvention through AI.

I do not tell this story for sympathy. I tell it because every small business owner I work with is somewhere in the middle of their own version of it. And they deserve someone who has actually been there.

Career timeline

Where I have been

1983 - England

Paper Rounds & Packed Lunches

Started with two paper rounds and selling my bag lunch at school. Understood supply and demand before I knew what the words meant. Two paper rounds at Christmas meant double the bonus — double the return. That instinct to find the angle, stack the opportunity, and work the system has never left me.

1986 - England

Moved into the Motorcycle Trade

Left school and moved straight into the motorcycle industry. This was the beginning of a deep relationship with the trade — the machines, the culture, the business of it. Everything that followed in New York started here.

1991 - England

Three Jobs. One Goal. First House at 20.

Working three jobs simultaneously: cleaning from 5am to 7am, parts guy at the dealership through the day, then cleaning again from 9pm to 11pm. Eighteen-hour days. Not because I had to — because I had a target. Bought my first house at 20. That is what outworking everyone looks like before anyone is watching.

1993 - England

Reset. Divorced at 22.

Divorced at 22. No kids. Lessons learned. Gave the house to my ex-wife — an amicable split, no bitterness. Sometimes the right move is to close a chapter cleanly and let both people move forward. A year and a half later I left for the United States. Some decisions look like loss at the time. That one changed everything.

1990s - UK

UK Motorcycle Industry

Started my career in the UK motorcycle industry. Learned the fundamentals of retail, customer relationships, and how to sell high-consideration products. That foundation has never left me.

1994 - New York City

Ducati Manhattan - General Manager

Moved from England to New York City at 24. Became General Manager of Ducati Manhattan on 11th Avenue and 42nd Street, the world's first Ducati Solus flagship store. This was during the Ducati IPO, and I was running the social and brand side of one of the most talked-about retail experiences in the city. The store became a cultural scene. We hosted Italian-themed parties with famous chefs. We physically manhandled Ducati 916s through hotel kitchens to get them onto showroom floors for events. We had product placements in Barb Wire and Matrix Reloaded. Law and Order filmed connections to the store. Nicholas Cage, Harrison Ford, and a long list of stars came through because they were genuine motorcycle fans and the store was a genuine destination. I then moved to Ducati Atlanta before launching Casoli Moto.

Late 1990s - Atlanta, Georgia

Ducati Atlanta - General Manager

After Manhattan, moved to Ducati Atlanta. Continued building on the brand relationships and operational experience from New York. The US motorcycle market was evolving fast and I was in the middle of it.

1999 / 2000 - Florida

Casoli Moto USA - Co-Founder

Moved to Florida and co-founded Casoli Moto USA. Built on deep market knowledge and strong brand relationships from years in the Ducati network. Close to $1 million in revenue in the first year. Then came the divorce that changed everything.

2006 - The Hardest Chapter

Lost Everything. Lost My Son.

A second divorce took everything — the business, the assets, the stability. But the hardest part was losing my son. His mother fled the state and I did not see him for 14 years. I kept building because that is all I knew how to do. He came back into my life after she passed away. Some things you carry quietly. Some things you build through. I did both.

Early 2000s - The Rebuild

Starting Over From Nothing

After Casoli Moto, I found myself with nothing. No home, no business, no money. I walked out of one of the hardest periods of my life with one phone number I could remember from memory. A friend drove 65 miles to pick me up. I lived in his garage by day and slept on his sofa by night. My only asset was one HP Pavilion PC. I started teaching myself to build websites. I sold Flash banners on eBay for $20 each. That led to full websites, which led to a deep obsession with SEO. The lesson that stuck: anyone can build a site. Getting it found by people with money in their pockets is the real skill. That conviction has never left me.

2010 - Present

Construct Media - Founder

Started Construct Media as a digital agency focused on web design, SEO, and digital strategy for small and mid-size businesses. What happened next was years of deep, self-directed learning that became the foundation for everything I build today.

I baptised myself in Magento when it was still a community edition, then moved on to Magento Enterprise. I learned Volusion and a string of early e-commerce platforms — some of which I cannot even remember the names of now. I taught myself PHP, WordPress, Flash programming, HTML, CSS, and started to understand JavaScript. I went deep on server configurations, infrastructure ownership, and the full mechanics of how websites actually work under the hood.

A lot of it was just me. No team, no course, no shortcut. Pure inquisitive nature and a refusal to not understand something. I taught myself to use Google Developer Tools, learned to read the DOM, understand how pages load, diagnose performance issues. I picked up Screaming Frog, Ahrefs, SEMrush — all the deep technical SEO tooling — through real client work, not theory.

That obsession with owning the infrastructure, understanding every layer, and diagnosing anything that was broken — that is the same instinct I bring to AI systems today. Construct Media was where I became a builder. My largest client at the time convinced me to come in-house as VP, which led directly to the Premier Table Linens chapter.

Original eBay Banner Listings - $9.95 Static · $29.95 Animated

Construct Media - Static Banner eBay listingConstruct Media - Animated Banner eBay listing $29.95Construct Media - Recent banner work examples

Click any image to view full size. These were the original eBay listings that started it all.

Corporate Chapter

Premier Table Linens - Vice President

My largest Construct Media client convinced me to come in-house as Vice President. I took that role seriously. I built the team, hired the people, and spent a significant part of my time either defending them or fighting for them. We grew the company to $6 million a year. That part I am proud of.

The environment was difficult. The ownership was not built for people — not for staff, not for customers, not for partners. I watched first-hand how a business can grow in revenue while shrinking in culture. I learned more about leadership in that chapter than almost anywhere else, and most of it came from watching what I did not want to be.

I stayed as long as I could justify staying. When I could not, I walked. No drama. No burning bridges. Just a clear decision that my energy was better spent building something I believed in. Looking back, I am grateful for every lesson that place gave me — even the hard ones. Especially the hard ones.

2018 - Present

Logoclothz - Co-Founder

Co-founded Logoclothz with Paul Bucklin. A custom branding and tablecloth printing company serving businesses that need high-quality branded table linens and event print. Built on an AI-powered operations and fulfilment system — every order, every design, every customer interaction runs through an agent stack I built and maintain. Logoclothz is the live proof-of-concept that AI-run e-commerce works at the small business level. Visit logoclothz.com.

Corporate Chapter

ZenBusiness - SEO & Digital Strategy

Worked with ZenBusiness on SEO and digital strategy. Jason Dowdell has been an instrumental mentor and close friend — someone who has been there for me on many levels, both professionally and personally. I have had the fortune to work alongside him and build a genuine friendship I am grateful for every day. To the entire SEO team — Charlie, Sherrill, Katie, and everyone else who was part of that chapter — thank you for everything I learned from you all. A truly remarkable group of people. I was blessed to be part of that team.

2022 - Present

Cancer Diagnosis - Recovery - Reinvention

I was diagnosed with lung cancer. I spent close to 18 months in recovery - a lot of that time in bed. I used that time to go deep on AI. Not casually. Obsessively. I am now 3 years in remission and building harder than I ever have.

2023 - Present

Ready, Plan, Grow! - Co-Founder

Co-founded Ready, Plan, Grow! with Marcela Shine — two Gen X founders who went from typewriters to teaching AI. Both of us were part of the corporate culling of 2023/2024. We built Ready, Plan, Grow! because small business owners deserve real frameworks, not hype. You own everything we build. No vendor lock. Ever.

What we do: The Clear Business Framework — four hats every founder wears: CEO, COO, CFO, CMO. A framework for each one. Built around the Business Backpack: your complete knowledge base, brand voice, ICP, differentiators, and processes. Yours to keep, forever.

  • Marcela has directly coached 5,000+ entrepreneurs through Ureeka, ZenBusiness, Google for Startups, Comcast, and the Dallas Mavericks Entrepreneurship Program — including alongside Kevin O’Leary and Mark Cuban
  • Kasi Nayles (For The Few) went from buying inventory on gut feel to making every purchasing decision backed by real numbers — then went after grants with real confidence
  • Terrence Southern (Robotopia) doubled his traffic and booked more speaking engagements after building a centralised knowledge base through the framework
  • Sunny B. (Foodesign Associates) repositioned a 50-year-old brand, shifted profitability, and grew revenue
  • Elite Design Group went from invisible to ranking for key terms and getting inbound inquiries

Know Your Numbers

Watch how Kasi went from buying inventory on gut feel to making decisions backed by real numbers.

Vendor Lock

Marcela and Ryan at the Charlotte Latin Chamber of Commerce on the vendor lock-in trap.

May 2025 - Building

aiwithrye.com - Founder

Built aiwithrye.com as the public home for everything I have learned about AI architecture, agent systems, and practical AI for small businesses. This is where I share the real work — not the hype. Free tools, long-form breakdowns, and the honest story of what it actually takes to build AI systems that run a business. You are on it right now.

The AI evolution

My AI Learning Roadmap

That is the rub with it moving so quickly. I went from chatbot to prompting to prompt engineering to agent builds to infrastructure to skills - and now loops to tie it all together. A single instruction to our central system: "I like this article. Rebrand and distribute as Ryan on our blog and LinkedIn. Make a 30-second YouTube short." Everything I spent years building, coming to life.

01

Chatbot → Prompts

Started where everyone starts. Learned that output quality is entirely dependent on input quality. Spent hundreds of hours just talking to models.

02

Prompt Engineering

Chaining prompts. Using the output of one as the input of the next. Thinking in workflows, not single queries. Roles, constraints, negative rules.

03

Agent Builds & Skills

Reusable modules with defined inputs and outputs. Treating AI like infrastructure you design. Scarlett, Morpheus, Trinity, Ghost - each with a defined role and hard boundaries.

04

Infrastructure

Anchored everything in data. Built our own harness. Not relying on anyone else's platform. Knowledge bases, SEO pipelines, client OS - 90-day rolling content curated from real data.

05

Loops

Full orchestration. One instruction triggers research, writing, branding, publishing, and video creation across every channel. This is where I operate now - and it is wild how far it has come.

Operating here now
What I have learned

Six things I know for certain

AI does not replace judgment. It amplifies it. The human in the loop is not a bottleneck - it is the quality control.

Most businesses do not need more tools. They need better systems. The tool is the last decision, not the first.

SEO and AI are converging. If your content is not structured for LLMs, it will not be found by the next generation of search.

Recovery taught me patience. You cannot rush compounding. In business or in health.

The best AI implementations are invisible. The customer just notices things work better.

Small businesses have the advantage. They can move fast, test quickly, and adopt AI without a procurement committee.

Contact me

Got a project? Let’s talk.

ryan@readyplangrow.com