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The Rebooting founder Brian Morrisey shares what it means to be a first-time founder and how to find your footing.

Starting a company for the first time is one of the most exciting, rewarding, nerve-wracking, keep-you-up-at-night feelings. And yet, every successful entrepreneur started out as a first-time founder. They didn’t reach the peak of their careers by not starting a business. And even very successful people who have spent their lives building a corporate career may find themselves in the founder’s seat and start building a new version of success.

Host Freddie Laker, a serial entrepreneur, and Brian Morrisey, founder of The Rebooting, discuss Brian’s journey of starting a company for the first time after spending decades covering successful entrepreneurs and leaders in his Editor roles at Digiday and Adweek. We’re going to dig deep into what it means to be a first-time founder and find your footing—a must-read for anyone starting or aspiring to start a business!

Meet Brian Morrisey, Founder of the Rebooting

Having spent 20 years as a journalist, Brian Morrisey found early success in covering the business side of journalism and helping to shape its evolution. He specialized early in his career, focusing on the early stages of online advertising growth. He has grown a number of publications, including Glossy and Modern Retail. At a turning point in his career, Brian wanted to do something different within the industry, so he launched The Rebooting—a publication focused on a literal “rebooting” of the media industry. What started as a personal project has now become a real company and brand, placing Brian in his first-ever role as a founder.

Freddie: The publishing industry has been completely disrupted by digital technologies. What does it take to make a publishing business more sustainable?

The internet has eroded most of the ways that traditional publishers made money. A lot of industries have faced similar upheaval by digital technologies, but publishing has been one of the most heavily affected. But Brian shares that it hasn’t all been doom and gloom.

Technology has allowed advertisers to find audiences and precisely measure the results of that advertising. Many publishers have struggled because they were not able to adapt their business models to fit these new realities. They’ve spent time chasing the newest and shiny object, the one thing that was going to turn around their business, whether it was iPad editions or Facebook live video. Or they’ve spent their time complaining about how Google and Facebook were taking their businesses. 

“The reality is that publishers need to take control of their own future, and they need to build sustainable business models. There are still a lot of profitable publishers out there who have built better business models. 

“A lot of the problems of publishing, including the ones from a consumer’s perspective (like terrible web experiences) aren’t technology challenges. They’re business model challenges. It’s not like these publishers don’t know that the user experience is terrible. They’re operating under the idea of Don’t hate the player, hate the game. I think it’s better to invent a new game rather than see how much you can get away with.”

Freddie: What were your top considerations when starting a business for the first time?

Having left DigiDay in October 2020, Brian didn’t have a plan for what was next. He knew he wanted to stay in the industry long-term but had a myriad of challenges to overcome in getting to the next step: non-competes, staying relevant, maintaining industry connections during non-compete periods, etc. 

“Even though I didn’t have a plan, I knew I wanted to see a few things happen. One was to go back to creating content. I’d written for a long time, but the last 10 years of my career took more of a managing role. Being able to start creating things again was going to be hard but so rewarding. 

“I also wanted to build something that others would see as valuable. I wanted a product that would be essential to people building media businesses. And I had to make sure there would be a business model there. I wanted to make a product that I liked and is also unique.”

Freddie: Building your first start-up at 48 is no easy feat. What have you learned in the past year of running your own business and not just being the leader of it?

Brian transitioned from a team management role into running the day-to-day operations. He’s producing content and getting back to his craft, but he also has to handle things like financials, revenue growth, marketing, and a myriad of other moving parts.

“I look at running a business like an elimination diet. As you get older, you end up having things like heartburn and stuff. You’ve got to figure out what the trigger is. So you start removing things to figure out what you should and shouldn’t be eating. In business, I take a similar approach. I start thinking about my greatest points of leverage. What do I do best? Where do I need help? What can I do or not do?

“I’ve found that I’m pretty good at selling, even though I’d never done that before. But I’ve found that I don’t have to do design. I don’t have to do my own audience development. I don’t have to handle the monetization side. Other than creating great content, I can hook up a Stripe account and be in business, provided I’m giving people value and products they support. It’s like having the best of solo autonomy and the security of a larger organization. This is a great balance to not have to deal with the stuff you’re not good at while also focusing on the things you are good at. Even the most successful entrepreneurs don’t have to do everything themselves.”


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