This PR Agency Went from Zero to $1 Million ARR in Its First Year By Helping Startup Founders Share Their Stories

Sharing founder success stories is one of our passions at Bootstrappers. And it’s always exciting to meet like-minded people. Michael Stern, the founder of PR agency HeadStart, is on a similar mission to us: Tell as many startup founder stories as possible.  

Our CEO, Andrew Gazdecki, has tweeted that startups don’t need PR agencies. Michael agrees to an extent: “It might be too early for a startup to hire a PR agency, but they’re never too early to tell their story. All startups should have an earned media strategy as soon as possible. And if the founder doesn’t have time to execute that strategy themselves, HeadStart can jump in.”

Earned media is the publicity a company generates organically, such as through customers, social media fans, journalists, or bloggers. Earning media in trusted outlets and news publications helps boost brand awareness and increases credibility. 

Michael says, “We tell our clients that they should only have to pay HeadStart. We don’t force them into pay-to-play PR. Typically, that form of PR doesn’t get as much exposure. We focus on pitching reporters as opposed to paying for advertorials as it’s more effective for early traction.” 

HeadStart has been profitable since day one – and the agency went from zero to $1 million in annual recurring revenue after only six months in business. In the past nine months, HeadStart has grown from one employee to a team of 15.

Burning Out in News, Thriving in Public Relations 

Michael’s background is in media. He graduated from the University of Maryland, College Park with a degree in broadcast journalism and became the morning executive producer for local TV. “I woke up at 2 AM every morning and, as you can imagine, that gets old quickly. On top of that, it was a crazy time to be in the news, especially with COVID, and I ended up burning out. So I left the industry and went into PR like many others do after leaving news,” he says.  

Michael Stern (right), the founder and CEO of HeadStart

Michael joined a large agency in DC where he worked with Fortune 500 companies. “For them, public relations is just checking a box. They have the money to spend, so why not spend it on that? We weren’t really about making a difference for those companies with PR. It was more of a formality,” he says.

Although Michael had been working a traditional job for four years, he’s always been an entrepreneur at heart. “I started my first business in fourth grade, selling little origami frogs in the school hallways. I also launched a school newspaper that year. Similarly, in college, I started several publications. I always wanted to start my own company, but I went with the safe route instead and got a regular job right out of college,” he says. 

The idea for HeadStart came to Michael while he was in an accelerator program for a different startup that he cofounded. “Someone in that accelerator asked a question about PR and I answered. My advice got their company media coverage right away. It got me thinking about PR for startups. There’s a niche of founders with great startup stories who don’t know how to tell them to the world. They often think it costs tens of thousands of dollars to share their story in the media, but it doesn’t need to.”

Michael launched Headstart in April of 2021 to help companies that can benefit from PR. He originally wanted HeadStart to be a PR consultancy. He says, “I didn’t think founders needed to hire an agency to get press. I thought that founders would just want to do it themselves after getting consulted. I would advise them on how to tell their own story. But I was quickly told that they would rather pay an agency to do it because they simply didn’t have the time. So, HeadStart went from consultancy to agency pretty early on.”

Achieving That Coveted Hockey-Stick Growth

Once Michael decided to start his own agency, things just fell into place. He says, “I launched the website for HeadStart on a Wednesday, let’s say, and that Friday I got a message from a connection asking if I could help their startup with PR. I was still at my day job at the time, and I hadn’t even promoted my new business yet.” It was as if the universe had presented Michael’s first client on a silver platter.

Michael took on that company as the first HeadStart customer. “That startup got great press early on. It didn’t take long to get it coverage on CNBC and a Business Insider profile. With that, HeadStart had its first case study,” he says.

The founder used that case study to convince other startups of the results his agency could deliver. That one client turned into three and then five. At that point, Michael knew that he could leave his full-time job and earn enough to support himself. After he resigned in August 2021, HeadStart’s client roster kept growing.

For the first four months, Michael was the only full-time employee at HeadStart. He says, “You’re wearing 15 different hats because you’re not in a financial situation to outsource some of those hats to other people. In those early stages, I was essentially a freelance PR person working crazy hours.”

But once the agency acquired eight clients, it was time to expand the team. In September of 2021, the founder hired his first three employees – two of which are now also his cofounders. First, Michael hired HeadStart’s CFO to manage the financial side of the business. Later, Michael hired the first PR-specialized employees to share his workload.

Last month alone, the agency hired five new team members. In a matter of nine months, HeadStart went from just one employee to 15. Michael says, “It’s only recently that I’ve been able to take a breath and look at how fast we’ve grown.”

Bringing Fresh Blood to the World of PR

Michael, along with his cofounders, saw HeadStart as a way to bring new blood into the industry, taking a different approach to PR than his established counterparts. He says, “In speaking to startup founders, I realized that one reason they don’t like traditional agencies is that most of them aren’t compatible with the startup world. For example, an agency would spend two months on an angle that they were convinced would work but didn’t. That’s two months on retainer that a startup can’t afford to lose.”

HeadStart knows that startups don’t have that kind of time. Some don’t even know if they have two months of runway left, let alone two months to pay an agency without results. Michael says, “Startup founders want to partner with people who understand startups, who have lived the startup life, who have had to fundraise before, or who have had to acquire their first customer.”

When a startup comes to HeadStart, it doesn’t take weeks or months of discovery to figure out where they fit into the media landscape. Instead, the agency makes a couple of calls and the startup gets its first interview request almost right away. They’re able to produce those results much faster than traditional PR firms – and at a much better price. 

How does the agency do this? HeadStart sets itself apart with a nimble and flexible team that can react to trends fast. Michael says, “As a startup, you never know what could happen from one day to the next. We have a client who’s had to pivot three times in three months – and our team needs to be prepared to flip the strategy on a dime. We’re able to do that because of how HeadStart is built. We can help startups at the drop of a hat with a remote, young, and flexible team. 

“A young team means that we haven’t spent decades in the PR world. I didn’t want to hire institutional PR people because they’re often stuck in their ways. Many of HeadStart’s team members are former journalists or producers, like me. They left the news world for one reason or another, and this is their first job in PR. Now they get to tell stories differently. And when it comes to PR practices, that means we’re open to trying new things.” 

As former journalists, they also have connections to media outlets and know what reporters are looking for. This helps HeadStart get results quickly for their clients. The founder says, “When I was pitching to the media, I realized that I could get results so fast because I knew how the business operates. I knew what journalists wanted. Bringing on like-minded people has helped me grow HeadStart into what it is today.”

To cater to startups that often don’t have a big budget, HeadStart keeps costs low by eliminating unnecessary overhead. Michael says, “We don’t have an office. We aren’t using 20 different PR software tools to do a job that just one piece of software can do. And we aren’t structured like a traditional PR agency. Instead of an entire PR team dedicated to one client, we have PR specialists who help three different startups at a time. This allows us to keep our staff leaner while helping more startups and remaining profitable.”

Growing Quickly Does Come With Its Challenges

HeadStart launched in the middle of the pandemic. However, Michael was lucky to get started after the worst of the economic downturn had passed. In 2020, agencies lost a lot of business. Companies needed to cut their expenses and marketing and PR agencies were the first to go.

But in April of 2021, companies began spending money again. Michael says, “We hit that upward swing perfectly and benefited from it. I knew that we were going to be a remote company from the start. And because of COVID, I didn’t have to convince anyone that working remotely was the way to go. On top of that, there was (and still is) a boom in new startups being founded as we came out of the pandemic and experienced the Great Resignation – so we were able to ride that wave as well.” 

It seems like it was plain sailing for HeadStart, but there was one big challenge. Michael says, “It’s going to sound like an answer to one of those interview questions where you turn a negative into a positive, but the biggest challenge to date has been keeping up with the growth we’ve experienced.” The HeadStart team was essentially building the airplane while flying it, updating their internal and external processes along the way. They didn’t expect to hire so much in the first year, but it was the only way to keep up with demand.

Michael shares that hiring a new employee was incredibly stressful as he didn’t have the safety net that external investment gives you. A funded startup might have one year of runway and can afford to make mistakes in hiring, but that doesn’t apply to bootstrapped companies. In those early stages, it’s hard to make projections and decisions. 

He says, “For us, it was more like, we have a month runway and we are about to hire this new person. Our projections say that we’re going to keep growing, but what if it suddenly stops? Then this person would lose their job almost immediately. Luckily that didn’t happen – but it takes a toll on your mental health as you’re now worrying about other people’s income alongside your own.”

Don’t Buy Into the Rise-and-Grind Mentality

It’s easy to let the stress of being a bootstrapped founder get to you. Michael warns other entrepreneurs: “Startup culture is BS. The idea that you need to work 24 hours a day, seven days a week, 365 days a year to be successful is a myth. It’s okay to shut down your computer and take time to eat lunch. It’s okay to take the weekend for yourself or binge-watch Netflix in the evening. Your company is still going to be there when you come back.

“And if you don’t take time to switch off, you’re going to burn out and then you can’t grow your startup at all. I burned out in news – and I’ve seen many people burn out starting their own companies. It’s so important to prioritize your mental and physical health when you’re a founder. Don’t buy into the rise-and-grind culture as the only way to make it work,” he says.  

One of Michael’s priorities as a founder and CEO is fostering a progressive and employee-friendly workplace. He says, “I wanted to create the type of environment that I would enjoy working in as an employee. HeadStart has instituted a four-day work week, allowing team members to have three-day weekends. We also have unlimited PTO and sick days, so people don’t need to worry about taking vacation or mental health days when they need it.”

Although it comes with a lot of stress, if Michael could give his younger self advice, he would go back to his senior year of college and tell himself not to take the safe route. “Somewhere deep down I knew that I would end up as an entrepreneur, so I should have taken that leap sooner. I kind of regret the four years that I waited to start my own business because I wasn’t happy at my day job. Now, I get to do something I love,” Michael says.

HeadStart’s mission is to tell as many founders’ stories as humanly possible. If there are a million founders who need their stories told, they want to help a million founders.

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Andrew Gazdecki
Andrew Gazdecki
Andrew is an award-winning serial entrepreneur with three exits. He’s the founder and CEO of MicroAcquire, the world’s most founder-friendly startup marketplace, and its rebellious child, Bootstrappers, which gives voice to the entrepreneurial underdog. When not building businesses, he writes for Forbes, Entrepreneur, and now, Bootstrappers.

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