About Tom Cheddadi
I built and exited two seven-figure companies. Now I'm scaling Setsail, and helping other founders scale theirs.
Co-founder of BuddyBoss (exited) · Co-founder of Rapyd Cloud (exited) · Co-owner of Setsail
Setsail Marketing is the performance marketing agency I co-own and lead strategy for. We're optimizing operations, scaling sales, and improving the quality of what we deliver. And we're putting AI to work two ways: sharpening how we deliver, and keeping our clients ahead of the game with it. Own Your Agency is the consultancy I founded to help other agency founders make the same transition I made: from wearing every hat to a business that runs without them, generates real profit, and gives them their time back.
I'm Tom Cheddadi, a Canadian-Moroccan entrepreneur based in Dubai, with summers in Vancouver. I co-founded BuddyBoss, the WordPress community platform that scaled to 120 people across Vancouver, Dubai, and Manila, crossed $7M in annual revenue, and powered online communities for over 50,000 customers worldwide. Impact Theory, Jay Shetty, Frank Kern, Maxwell Leadership, the Female Entrepreneur Association, and The Happy Pear all built on it, alongside thousands of universities, hospitals, and nonprofits. We exited BuddyBoss in 2024.
I co-founded Rapyd Cloud, the highest-performance managed WordPress hosting on the planet. Built for the same audience and for more complex sites that needed serious performance under load. It hit seven figures in nine months. I exited in 2025.
Today I'm a co-owner and CSO at Setsail, a performance marketing agency. I also run Own Your Agency, a strategy and delivery consultancy for agency founders.
I didn't start as a founder. I started as someone who just wanted to win.
Fresh out of university, I knew one thing clearly. I didn't want a normal life, a normal job, or a normal salary. So I went all in. I'd start my day at 1am working on freelance projects, nap before dawn, shower, and head to my full-time job as a front-end developer. Weekends I'd switch off my phone so nobody could distract me. I didn't have much of a life. I had a mission. And I was willing to sacrifice everything to see it through.
That work ethic is what brought me to BuddyBoss. The product was small at the time. A WordPress theme that pulled a steady trickle of leads from people who wanted to build their own communities, memberships, and online schools. I took over the agency side of the business, the customization work those leads turned into. Six months in, I had grown that agency from $7K to $65K a month at over 70% margins, with a team of five.
In June 2014, my co-founder and I decided to go 50/50 on BuddyBoss with a shared vision to grow it into a real software company. At the time, the agency was the main part of the business. It generated most of our revenue, and we used those profits to fund the new products we were building and the team we hired to build them. In 2019, after five years of iteration and customer feedback, we launched the BuddyBoss Platform. The BuddyBoss App followed in 2020. Those eventually became the majority of our revenue. The company shifted from being an agency to being a product company, and the agency had served its purpose: turning us into a successful multi-million-dollar product company.
But my passion for the agency was still there. Even after we shifted into being a product company, the agency was still there. Not the main focus, but still there. I still missed it.
The agency was the thing I was natural at, the thing I'd started with. The product company was the result of an untapped opportunity we had to take. But the agency was what brought us there.
Inside BuddyBoss, my role kept changing. In the early days, I wore every hat with a small team. As we grew, I started rotating through them. I'd take one role on, hire my replacement, and move to the next. Eventually I'd done every job in the company. Then I built a management team I could guide. As we kept growing, that became a real C-suite. They ran the show.
My meetings shifted from calls with every person to calls with just the executive team. One of them eventually became Managing Director. By the time we sold, I'd been out of day-to-day operations for a year and a half. I was making a seven-figure net income on autopilot.
Over the decade, we scaled BuddyBoss to 120 people at our peak across Vancouver, Dubai, and Manila, crossed $7 million in annual revenue, and powered online communities for over 50,000 customers worldwide. Impact Theory, Jay Shetty, Frank Kern, Maxwell Leadership, the Female Entrepreneur Association, and The Happy Pear all ran their platforms on it, along with thousands of universities, hospitals, and nonprofits. More than 45,000 websites have been built on BuddyBoss, and over 20,000 are still running on it today. We exited in 2024 in a multi-million-dollar private deal.
While we were still running BuddyBoss, my co-founder and I started Rapyd Cloud. It was the same observation that started the BuddyBoss agency. The people building on top of our platform needed something that didn't exist yet. Their hosting couldn't keep up. High-traffic communities, course platforms with thousands of concurrent users, ecommerce stores running on WordPress. None of the off-the-shelf hosts were built for that load.
So we built it. Managed WordPress hosting engineered for the high-traffic membership and ecommerce operators we already understood. We hit seven figures in nine months. I exited in 2025. I wanted to come back to something I really loved, which is agencies.
What I didn't expect after Rapyd Cloud was the loneliness.
For more than a decade, my family and some of my closest friends had been my co-workers. We built BuddyBoss together, then Rapyd Cloud, often in the same houses, in the same time zones, on the same problems. When the work ended, so did the daily orbit with most of them. The rhythm of being shoulder-to-shoulder with people every day, that part was gone.
The first thing that brought me back was Vancouver. I'd missed it without realizing how much. Just being there got me excited again. Made me feel like myself again. It's the closest thing I have to a place that's just mine, separate from any company I've built or am building.
“Vancouver brought me back to myself.”
In Vancouver, I started spending more time with Jason Atakhanov. We'd been friends for nine years. He'd been building Setsail Marketing, a performance marketing agency, and we got to a place where we talked seriously about me coming over to help him scale it. The case made itself. I'd built and scaled an agency from $7K to a multi-million-dollar operation. I'd taken a software company through to exit. I knew the operating systems, the people decisions, the financial architecture, the leverage points where margin actually lives. I could bring real experience to the table.
I came on as co-owner and CSO. We're turning Setsail into a systemized operation with a global workforce, productized services, and a delivery model built around what's actually happening with AI today.
Going deep into Setsail, I learned about its many strengths and its weaknesses. My job is to come in and help fix those weaknesses. Setsail isn't alone in that. The agencies I've seen up close typically wrestle with the same kinds of operating gaps. Cash flow. Lead generation. Hiring. Delivery. Retention. Billing. Every layer of the business. Gaps with a clear shape if you've solved them before. Things you can systematize, sequence, install.
That's why I also started Own Your Agency. Most agency founders don't need more coaching. They need someone who's actually built and scaled an agency business to look at their situation honestly, tell them what's broken, and then either coach them through fixing it or fix it for them. We diagnose what's actually keeping the agency stuck and prescribe the path forward. Then we deliver it. Strategy, systems, and the operating support that turns founders into owners.
My base is Dubai. The energy of the city pulls me up every day. I work hard here. I'm jumping into my next chapter head-on. Setsail, OYA, and what comes after.
I grew up in Guinea, West Africa. I went to school in the United States. I'm Canadian, and I lived in Canada for years before settling in Dubai. The US gave me language and a feel for doing business in the world's most competitive market. West Africa made me street smart. Less naive, more cautious, better at reading people and situations quickly. Over the years I've built and led teams across the US, Canada, Europe, the Philippines, Bangladesh, India, and Pakistan.
Summers we're in Vancouver. The rest of the year, Dubai.
Proud of what we built. Even more excited for what's ahead.
“The exits aren't the point. They're a head start.”
Working on the same transition? Let's talk.
Through Own Your Agency, I help agency founders make the move from wearing every hat to a business that runs without them. Strategy, systems, and the operational support to get there. Same playbook I used at BuddyBoss.
Book a strategy call