Why Entrepreneurs Need Each Other: A Lesson on Becoming a Better CEO From the Founder of a $12 Million Media Agency

Few founders are truly prepared for success. It’s such a long slog to the top, it’s easy to lose track of how important you’ve become to your teams, customers, and partners. Ross Hudgens, the founder of Siege Media, spent years building his media agency to over $12 million in annual revenue. A stratospheric climb by any standard – but, he discovered, into thin and empty air.

Living the cliche, Ross clung on to too much for too long. His story of building one of Inc Magazine’s 5,000 Fastest-Growing Companies (five years in a row) is typical of many founders who’ve struggled to fire themselves from roles they’ve always done alone. But Ross has never been afraid to ask for help, which, he argues, has helped him to become a better CEO.

Today, Siege Media employs over 100 people, has helped household names like Tripadvisor, Airbnb, and Casper boost traffic, and has established relationships with some of the biggest publications in the world, including Time, Fortune, and Entrepreneur. If those success markers haven’t convinced you, Ross also attracted a large private equity investment in April 2021. 

What does this mean for the battle-scarred founder? Breathing room. Now Ross has scaled his business, overcome towering operational challenges, and fostered a cohesive company culture, he’s learning to be a better leader. It’s not easy, Ross admits, to manage a remote team and fluctuating revenue, but he’s earned some time to reflect on his next move. 

“The CEO job is becoming more operational in mind and focus,” Ross said. “But the operations side is increasingly where I find the least joy, and there’s so much pressure there, too. I’m strongly considering hiring a COO so I can focus on where I add the most value on the marketing and strategy sides of the business.”

From Creative Writer to White Hat SEO

Ross started niche and then widened his expertise. After graduating in Business Marketing and Creative Writing from Chapman University in Orange County, he landed his first job scanning documents for a pharmaceutical company. The founder sensed there was something special about him and gave Ross a shot at flexing his marketing muscles in the real world.

“It was a contract research organization,” Ross said. “They’re that middle layer that makes sure drug studies are up to snuff. All I did was scan documents, but the founder was awesome and said ‘Ross, I know you’re a marketing major so use your marketing skills.’ I started googling, found SEO, and did a terrible job on their website, but that’s how I found my niche.”

From there, he landed a role at Sujan Patel’s SEO agency where he witnessed first-hand how the founder built businesses from nothing. It was an experience that stuck but it would be a few years before Ross launched Siege Media. The push came later, while he led SEO for a company that built lead-generation websites from scratch.

“It was my first taste of entrepreneurship,” Ross said. “The founder was great and let me run things, which meant I could experiment. But then they brought in a COO from a larger company who made me do a lot of spreadsheets and other admin that didn’t have much impact. It was  frustrating as it meant I no longer had the freedom or time to explore new SEO techniques.”

Finding the Confidence to Start a Business

While Ross treaded water under new management, the Google Penguin update reset rules for the SEO industry. Link building, or keyword stuffing as some might call it, was no longer relevant, or at least less relevant than before. What mattered was producing high-quality content. Being a skilled writer, Ross would flourish under the emerging SEO paradigm. 

“I saw things going towards content marketing versus link building,” Ross said. “I’d been blogging on the side so I already knew SEO writing. It was perfect timing. I already knew how content marketing worked because I’d built a personal brand and blogged on the side. And that gave me the confidence to quit when this overbearing COO came along.”

Sometimes all it takes is knowing your worth. Ross had taken his first risk, a crucial step of entrepreneurship that no one else can take for you. More, he’d hustled in his spare time to build a brand, community, and expertise that the Google Penguin update had made more relevant than ever. Resourceful and unafraid, Ross had the qualities of a CEO from the start. 

In the early days, Ross sometimes had to sleep at the airport (using a bag as a pillow) to catch an early morning flight to a client meeting.

“I made an announcement on my blog and got my first client,” Ross said. “I knew it wasn’t enough to feed me, but I started marketing myself more with this free time I had and eventually hit a threshold where I had enough business where I could pay someone. Then the business kept coming in so I hired a second person, and a third, and that’s how Siege started.”

How This Accidental CEO Learned What Matters

Ross confides that he never expected to start a business. He simply wanted to consult, be his own boss, earn enough to pay the bills, and enjoy the freedom to do as he wished. Simple ambitions and yet they escape so many of us. He certainly hadn’t envisioned being CEO of a multimillion-dollar business, and rising to meet the challenges of the role has taken its toll. 

Why Entrepreneurs Need Each Other: A Lesson on Becoming a Better CEO From the Founder of a $12 Million Media Agency
Siege Media’s first office could only fit two people.

“It’s stressful scaling a people business,” Ross said. “When it’s software like SaaS, for example, there’s less of a human cost, but I have a personal attachment to this company. I’ve gotten a little bit better being desensitized, but every person who leaves is like a little knife in me –  especially if it’s someone senior, and even if they leave on good terms.”

Media agencies like Siege often struggle to balance people with incoming work. It’s a fluctuating business model where contracts end and new ones must be renegotiated or new clients found to replace them. While there seemed an inexhaustible supply of clients in need of Siege’s help, Ross found it hard to keep up with demand while keeping employees happy. 

“One of our growth challenges has always been hiring in front of demand,” Ross said. “We’ve had to turn down a lot of work in the past. We recently invested more in intern programs. That’s been great for getting people exposed to what we do. We also provide full health benefits and a profit share, which although isn’t much, it’s much better than what other agencies offer.”

Siege is a remote company that respects employee lifestyles. Ross has nurtured a culture of positivity and respect, which he believes has made it easier to manage and motivate his teams: “Positivity is in our DNA. We have a gratitude channel where people get a shout-out. We screen for culture and only hire people who align with our values so there are fewer surprises.” 

Ross’s team is now fully remote, giving his employees a flexible schedule and a better work-life balance.

Ross cares deeply about his people and has been unafraid to put their well-being above the needs of the business. He’s paused client acquisition during busy periods, for example, and adjusted operational models to reduce the workload on account managers and creatives. Not only has this has reduced burn-out and boosted morale, but also led to better work. 

“We’re willing to stop growing to reset and fix what might be broken and learn from it,” Ross said. “We’ve paused client onboarding several times and increased our minimum account size. We also recently lowered our utilization rate, which hurt our profitability, but we care more about our people producing great work than constantly chasing numbers.” 

Helping People: The Ultimate Lead Generator

Media agencies are as plentiful as the stars, which makes you wonder: How did Ross manage to attract so many customers?  What was special about Siege Media? You could point to his SEO and writing expertise, to being a strong voice in his vertical, and to his focus on company culture, but without an effective growth mechanism and USP, he might’ve risked obscurity. 

“Many service businesses focus too much on marketing and ironically their client service is not that great because they haven’t looked inward,” Ross said. “We’ve elevated client service to a whole new level, which helps set us apart. We hired a VP of learning and development and have created over 100 docs and videos which we also sell externally as a training program.” 

Unsurprisingly, content marketing continues to be a massive hit for Siege Media. As well as focusing on client service with in-house training and resources, it also has 35 designers and creatives who help enliven written content with graphics and illustrations. A quick browse of Siege’s case studies reveals tight copy and contextual graphics, giving content a premium feel. 

“Ironically, I didn’t do much SEO because it would’ve been hard to rank against bigger players. Instead, we wrote blogs that helped people do SEO and content marketing right. Today, it’s shifted from blogging to social media and video with a premium aesthetic. We don’t have thousands of subscribers but some enterprise customers who’re very qualified watchers.”

Today, Ross takes a more methodical approach to business development, and it’s here his tone shifts from quiet reflection to self-reproach. While helping customers and employees has helped the business scale and be a great place to work, he wishes he’d hired departmental heads to take the pressure off him, which might’ve led to even better growth. 

“We have didn’t have a business development person until this year,” Ross admits. “It was just me doing all of the sales. I’m sure Siege could’ve done better and I could’ve fixed our operational issues if I’d gotten out of sales faster. I’d recommend anybody who’s running an agency to make that investment, not in year nine, which I did, but in year five or something.” 

Why Entrepreneurs Need Mentors (and Therapy!)

With the benefit of hindsight, it’s easy to be self-critical. In reality, no one could dismiss Ross’s achievements, and neither could they accuse him of false modesty: Being a CEO is a difficult, lonely job. I’m sure many founders would happily delegate the role to others if it were possible, but for most, like Ross, it’s a job they had to learn with the help of their peers. 

Don’t forget: founders must learn to be a good CEO while still managing the business. You don’t go to “CEO School” and then slide into the role equipped with all the leadership skills you need to succeed. Instead, you learn how to lead while leading (and enabling growth, strategizing, fostering culture, deflecting competition, and so on). And without help, you’d drown. 

“Will Reynolds of Seer Interactive who runs a 400-person agency is someone who’s always inspired me,” Ross said. “I probably could’ve used a CEO coach or something way earlier, but he’s always been there for me to answer any questions. We probably email once a month. He’s about five or ten years in front of me but has always been super gracious and helpful.”

Ross has also learned a lot through Entrepreneurs’ Organization: “I joined Entrepreneurs’ Organization this year. They match you up with similar businesses in your city and then you meet up. You do a little forum where you talk about your top five and bottom five moments that month. It’s very helpful and a bit like entrepreneurs’ therapy in a way.”

If you’ve ridden the entrepreneurial roller coaster, you’ll empathize with Ross. Otherwise, you might snort at the notion of entrepreneurs’ therapy however earnest it might be. But let this sink in for a moment: If you had over 100 employees, as many clients, plus a roster of partners and stakeholders, could you have managed it alone without support?

Delegation is as much about letting go as it is finding the right people. Ross admits that he long shouldered responsibilities that shouldn’t have been his. You can’t blame him. When you build a $12.5 million business from scratch, doing most things on your own, you forge bonds that are very hard to break. It took nine years before Ross finally accepted the relief of investment. 

“I still love SEO and content marketing and can see myself at Siege for a long time if I’m in the areas where I’m adding the most value,” Ross said. “One thing I’ve loved about the growth journey is that you’re always challenging yourself. I could never just stop at 20 people or something like that because I love the challenge of doing things I’ve never done before.”

What do you do when you achieve success? You redefine what success means. And that’s where investment helps. When you’ve bootstrapped a startup to millions of dollars, learned what it means to be a good CEO, and embraced failure as a teacher, funding allows you to apply those hard-won entrepreneurial lessons to new challenges, and I’m excited to see what Ross does next.


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