How Losing $130M Shaped a Playbook for Startup Founders

Colin C. Campbell is a seasoned serial entrepreneur and author with a track record of building and scaling multiple internet companies with a combined valuation of over $1 billion. He co-founded Internet Direct, one of Canada's largest Internet service providers, and Hostopia, which became the fastest-growing company in Canada before being sold to a Fortune 500 company.

What got you into entrepreneurship, and what ventures have you built along the way?

I did what every college graduate does. I went to work on the family farm. I started on a family farm, literally selling and flogging vegetables. My brother and I loved technology, and we launched a software rental business out of Toronto, Ontario, which didn't last long. Then, we launched a BBS, a bulletin board service. We decided to shut that company down and launch Internet Direct. We took Internet Direct to become the largest internet service provider in Canada, the third fastest growing company in Canada, and it was one of the big success stories in Canada until the .com bust.

There were not enough chairs to go around, and the music had stopped. The stock that traded at $19 a share, worth about a billion - I'm 29 years old here and had about 13% of the company. We agreed to sell our company to a cable company, and in March of 2000, something happened. A judge decided to break up Microsoft, and the NASDAQ fell from 5,000 to under 1200. Our company pulled its $50 million offering. 18 months later, we filed for bankruptcy protection, and the $19 a share was sold for six cents a share. You spend 10 years building the company, 10 weeks screwing it up on exit. It was the basis for the book Start Scale, X, Repeat. Your startup failures are the scars of your past that guide you through your new adventures.

Fast forward six years, and we took another company public. We sold it to a Fortune 500 company in 2008. I worked for that company for three years. In 2012, I was asked to speak to a group of successful entrepreneurs at MIT. They wanted to know how I could start, scale, and exit businesses at the right time. We sold our last company a month before the Lehman crisis. Timing is everything.

What I learned from that astronomical failure was two things: one, liquidity or control. Never sell your company unless you have liquidity or control.

When is the right time to exit, and how does the 'time to sell' index guide that decision?

Yeah, so I believe 50% of the company's value is an exit. Second, there are a lot of components to exit. I would say that who you choose to sell to is critical. You're going to sell to cashflow, which is often private equity in the United States. They might borrow at eight, nine, and 10% interest rates, but they need to make 16, 17, and 18%. And then you've got competitors. I like competitors because they can come in and eliminate expenses and give you a multiple. They won't give you a full multiple based on their total consolidated value. It's somewhere in between. But here is the nexus. It's strategic buyers. If you can sell your company to strategic buyers, they will take your technology or systems and apply them to their network and distribution, and pay you a much higher multiple. Hostopia sold for 17 times its EBITDA. We had a small business email hosting platform that we sold to Deluxe, a Fortune 500 company with millions of small businesses. They're thinking, can I take this platform and sell that to my millions of small businesses and get X amount? I worked for a Fortune 500 company for that three-year period. I bought a dozen companies. We had an army of analysts looking at how we could leverage those companies. So we want to try to sell to the strategic buyer because that will make a huge difference. Think about timing and think about who you sell to. I think those two things are critical on exit.

What led you to write the book? Was it your early exit experience, or was there something more behind it?

No, I think that was the premise of the book. That’s really where it came from. But it wasn't until 2012 that I was asked to speak at MIT that things clicked. I had to speak to 60 very successful entrepreneurs, and I thought, what will I talk about? So, I sat back and reflected on patterns in my successful companies: they were scalable, defensible, and caught a tech wave. Those were the first elements. Then I realized that at each stage, "start, scale, exit, repeat, " there's a story of people, money, and systems that shift with each phase.

As entrepreneurs, our instincts are stuck on "start." We manage everything and push forward, but things fall off when it comes to scale. The wheels come off the bus. We know how to run the business, but not how to motivate others to run it well. The secret is bringing in strong leaders to scale the company without us being the bottleneck. And most entrepreneurs are the bottleneck. That's why many companies fail to scale.

So yeah, it started with that MIT talk. I thought this was too good to leave there. I started writing Start, Scale, Exit, Repeat. The title came in 2012, and the book was published in 2023. I wrote on planes while traveling to 50 countries. Two years ago, Forbes Books got involved, and we interviewed over 200 people, some amazing ones. Geoffrey Moore, who wrote Crossing the Chasm — I read that 20 years ago, and here I was interviewing him. We also spoke with Verne Harnish, founder of EO, and Joe Foster, who founded Reebok.

What advice would you give entrepreneurs about catching the next big wave, like AI?

I have always had the fastest internet. I have the latest iPhone. I had the number 984 for the Model X for Tesla, the 984th vehicle delivered. I've always tried to figure out how to live in the future and what it means to catch the wave. Here, we have an opportunity where a paradigm shift, a technological shift like AI, is the largest shift in our entire lifetime. It's bigger than the internet. It's much bigger. It will mint more millionaires than any other technological shift in history. This is big, and I'm suggesting everyone get out there and use the technology. Sign up for as many AIs as possible. We had this big shock; the big paradigm shift was AI chat GPT 3.5. That was the time when you saw a lot of things happen. Now, if you go back in history, there was something called dial-up internet, the information superhighway. Then you had broadband takeoff. Then, you had a social media takeoff. The app revolution came in 2010, and then you've seen the rise of micro and e-commerce brands that took off from 2016 to 2022. That's the funny thing now that one individual could create a unicorn because you can do so much with the platforms that exist out there today, and with AI.

What's your advice for entrepreneurs to ride the AI wave without getting wiped out by the next big update or move from a tech giant?

Yeah, so assuming we're going to go into this tech chasm, we're going to move into a different environment. Some call it the tornado. It's this early majority, the pragmatic individuals, who buy your products and buy them like crazy. These innovators love these products, but then you go into this period where people don't know what to do with them. There are three things we need to do in a tornado, okay, to win. The first is to be a laser beam and be the best in the world at what you can be. Second, make it easy. People hate technology. Fundamentally, the vast majority of the human race hates technology. And we make it too complicated. If you make it easy and simple, they will take the path of least resistance, and number three, which comes directly from Geoffrey Moore (the author of Crossing the Chasm), is to deliver the fastest. People just want the technology. They want it now. Right? They want it now because they need it now, and you have to be able to serve it up. That's it. Those are the three things to win in a tornado. Make it easy, focus, distribute, and deliver the fastest. That's it.

Is there anything you’ve learned as an entrepreneur that’s not in your book and you’d want to share with early-stage founders?

Well, I often get that question, and I think it comes down to believing in yourself. When I was 22, 23, and 24, I didn't believe in myself enough. Then, I would definitely say get a coach. If you really want to scale your business, get a coach. I'm involved in incubators, including one in South Florida and another at NSU called the Allen LeVan Center. They do incubate programs absolutely free. They connect you. We have 20 speakers. I'm one of the first speakers to come in there and help with strategy. These are free resources. You can take advantage of free resources. You're not alone anymore. This is not the days of Wozniak and Jobs in the garage. This is the day when you have a community. It takes a village to raise a startup, and that's what you need to do. You need to get yourself involved in a community, and it's much more fun, too. That's it.

Have these handpicked highlights sparked your curiosity? You won't want to miss the full conversation with Colin C. Campbell on our YouTube channel or your favorite platform. The episode dropped on November 4th, 2024.