Behind the Success: An In-Depth Interview with Matt Culloty

Behind the Success: An In-Depth Interview with Matt Culloty

In the dynamic world of marketing, few stories are as compelling as that of Matt Culloty, an entrepreneur who embarked on a journey at 26 that led to the founding of a web design and development agency.

His venture’s acquisition and subsequent roles have cemented Matt’s reputation as a master in leadership, sales, SEO, web development, and design.

Today, as the driving force behind Duckpin and 7ten Digital Marketing, Matt’s insights into business growth and digital strategies are invaluable. Let’s jump into his experiences, strategies, and innovative approaches that make him a beacon for aspiring marketers.


Can you walk us through your initial foray into marketing and what inspired you to start your own web design and development agency at such a young age?

I was working as an IT Analyst at the Department of Housing and Urban Development in DC when I realized I wanted something more for my career.

After applying for multiple jobs that I thought were more interesting, I realized these opportunities were similar to the ones I was already in. Ultimately, it would leave me unfulfilled.

I had always looked up to entrepreneurs and business owners who seemingly had the ultimate freedom to set their schedules and pursue opportunities they dreamed up. Being 25 or 26 at the time, I was more naive than anything to think that I had the skill set to be a business owner, but I figured that if these other men and women could do it, so could I.

I also knew that my life would only get more complicated as I got older, so if I was ever going to take a shot at entrepreneurship, now was the safest time to do it.

Reflecting on the journey from founding your agency to its acquisition, what pivotal moments shaped your career and business philosophy?

I started by branding myself as a freelancer, promoting a skill set I developed while getting my Master’s in Interactive Media at Elon University.

I listed on a resume-style website that I could do graphic design, web development, UX design, SEO, and social media. It took about 4 months until I ranked number 1 on Google for “Freelance Designer Baltimore” and other variations of that keyword phrase, and I started getting phone calls. My hourly rate was $30 an hour, or I was promoted.

Nonetheless, I quickly started getting to work, which helped me in two ways. 1.) I was able to build a portfolio of actual work, and 2.) I got to discover what I liked doing most and what paid the best. This led me to build a lot of websites, which I enjoyed.

But after making $7,000 in the first 9 months, I knew I needed to change some things. quickly, I rebranded it Prositely with the tagline “Professional Websites, Easy.” The other pivotal revelation was understanding I needed to develop a recurring service offering.

So, I launched a Web Hosting and Maintenance plan for a monthly fee of about three times the cost of what you would pay GoDaddy or any other self-hosted provider. It was a no-brainer for any business owner who had sat on the phone with one of these companies for 4 hours trying to get their old broken website fixed. Having these recurring customers made my business “sellable” to another agency with a similar offering.

How did the transition from owning your agency to joining Duckpin, and what motivated this significant shift in your career path?

I fell out of love with running my own business, and my life outside the business changed.

After 6 years, I started only to enjoy the consulting and sales side of the business, and I could sense my clients were feeling that, too. I also often describe this moment as if I were on a never-ending treadmill workout. I would grow and then need to hire, grow, and hire more, and I couldn’t visualize how I could ever get off the treadmill.

Humbly, this is where my lack of business experience and organizational development skills fell short, but that didn’t bother me because I was confident I had something that I could sell. So, I used my network to get introductions with other Baltimore-based agencies to see if they were interested in purchasing my business. I had probably half a dozen conversations before I met Andrew Woods, the CEO of Duckpin.

Duckpin offered almost identical services to my Web Hosting and Maintenance clients, so we knew the transition would be relatively easy. We described the deal as a win-win-win. It was a win for Duckpin, my clients, and me because they now have access to a more responsive and built-out support team and new marketing resources that we didn’t have at Prositely.

In leading growth initiatives for Duckpin and 7ten Digital Marketing, how do you balance the creative aspects with the analytical demands of digital marketing?

Simply put, we balance this by having great talent in both areas. That makes my job, growing both companies, easy for two reasons.

For one, the results that we produce through our inbound marketing campaigns at 7ten and how we will replicate them for you is essentially what I show new prospects, and it sells itself, the same thing on the Duckpin side.

Our creative assets and deliverables look so sharp that prospects see them, and I don’t have to convince them of our qualifications because they can see them with their own eyes. Additionally, both companies support each other.

Our in-house teams work under the same roof, so when a lead gen client calls for high-end creative assets, our team just goes down the hall and talks to a designer, and vice versa. Most small agencies exist in silos, so when someone signs up with a digital marketing agency, they are often qualified to run SEO/SEM campaigns.

Still, if a client ever needs high-caliber sales collateral or a video project, they have to look elsewhere, and things start to look disjointed, and they end up having to spend more. With 7ten and Duckpin, we have full-service capabilities, and everything works together.

Your experience spans both the production and strategy sides of marketing. How has your hands-on experience in design, development, and marketing informed your approach to business development?

My approach to business development is first to build trust with a prospect and then ask for the business. My hands-on experience in production allows me to explain how these things work in a way that a non-marketer can understand and how it will benefit their business.

I’ll do a lot of the upfront strategy work before a prospect becomes a client because it gives them a look behind the curtain. And I am not just talking about general strategy. I’m talking about fundamental strategies and tactics for approaching a specific campaign.

I can also relate to the pain points for business owners that most salespeople can’t because I’ve been in their shoes, and I know the gaps they’re trying to fill.

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With your expertise in leadership, can you share a key piece of advice for marketers aspiring to take on leadership roles within their organizations?

Develop your training and education skills. Good leaders help others get better and lead by example. Being good at executing a marketing campaign is one thing. But being able to teach others is a different skill in itself.

The other key to taking on a leadership role is showing decision-makers that you understand the organizational strategy as a whole. In summary, being talented isn’t enough for executives to trust you can lead. Being analytical, teaching others, and demonstrating that you improve those around you will.

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Sales and SEO are crucial components of digital marketing. How do you integrate these elements to create a cohesive strategy that drives growth and increases exposure to target audiences?

Your sales team should be driving the discussion and defining your target audience, and your SEO team should be talented enough to figure out what those people are typing into Search Engines.

If you can align these two teams, then closing inbound leads should be smooth sailing. SEO is just one of about twenty different opportunities to reach potential customers. Still, I’ve seen it transform organizations to the point where I don’t understand how some businesses survive without it.

The landscape of web development and design is constantly evolving. How do you stay ahead of the curve and ensure your strategies remain innovative and influential?

Anyone who enters the web design and development business is naturally curious. Or at least it should be. However, a firm understanding of design and development fundamentals is the key to staying ahead. It sounds counterintuitive, but it’s true.

I was fortunate to have a great mentor in High School who taught his art students the fundamentals of design before teaching them how to draw and paint. I remember being 13 or 14 years old and discussing concepts like the Rule of Thirds and how to use repetition in your art.

That made me an immeasurably better artist. I took it for granted, but any new design trend is founded on basic principles that will always hold (Shout out to Jim Kuhlman). I think that’s also very true for developers.

In summary, to stay ahead of the curve, you need to have an extreme grasp of the fundamentals first, and then you can let your curiosity and innovative side take over.

In the context of tools and software, what essential tools do you rely on for your business development, marketing, and leadership work?

LinkedIn’s Sales Navigator is the single best digital tool for Business Development that I’ve encountered. I’ve also been fortunate enough to have Intero Advisory, the best LinkedIn Consulting firm on the planet, as a client and a coach, which helped me unlock it as a weapon for connecting with prospects, building my network intentionally, and closing new businesses.

I think SEMRush and Ahrefs are interchangeably pivotal tools for marketing, specifically inbound marketing. I’m shocked at some of the responses I’ve seen from some digital marketers online who critique its accuracy. After years of using those two tools and seeing the results we’ve been able to get our clients based on the research and data that they compile for us, I’m not sure we’d be able to do our jobs without them.

Not a lot comes to mind for “Leadership Software.” You’re in trouble if you rely on software or a tool to become a good leader. Good leadership is rooted in good communication, so Slack, Teams, Airtable, etc., are all important when building an increasingly remote team.

Our CEO at Duckpin built a custom platform that integrates Zendesk, Harvest, and other tools to streamline some of our most vital operations. If you can pull that off, that’s excellent leadership for me.

Looking towards the future, how do you envision the evolution of digital marketing and its impact on businesses, particularly in terms of SEO and web development?

It’ll be fascinating to see how AI affects SEO. We’re in the infancy of a new technology, and it will no doubt disrupt how people consume information and ask questions. God knows what else.

Local SEO will still be alive and well for quite some time. Still, the term “Search Engine Optimization” could someday become extinct if people rely solely on AI for recommendations or finding answers to questions.

Someone I know and trust recently said, “I haven’t used Google search in months.” I think brand and advertising will become increasingly more important because of this.

Web Development will always include an aspect of creativity and editing that AI can’t replicate … yet. However, will web development change for AR as new devices like the Apple Vision Pro are released?

It hasn’t been too long since smartphones came around. Who remembers how that changed things for web developers? The extinction of Flash? This keeps web developers and marketers busy and excited about all the obstacles that await.

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