How to Successfully Acquire a Content Website: Tips from an Entrepreneur’s First Bootstrapped Business 

John Culotta has worn many hats over the years. He’s been in and out of owning his own business, as well as dabbling in sales, the construction industry, home remodeling services and even full-time music. His lengthy resume has given him a wealth of knowledge and experience in the world of business. Through his successes and failures, he’s gathered much information to share with other aspiring entrepreneurs. 

John sat down with us to discuss his acquisition of Line25, a content website that provides tips and valuable resources to graphic designers and web designers. 

What Led Him to Become an Entrepreneur 

John considers himself a highly independent individual, at least where his work is concerned. “I’ve always had kind of this mindset of: I like to create designs and find solutions to problems, but not be micromanaged.” 

His many career moves have ultimately been to reach the desired end goal (like many other entrepreneurs) of being his own boss. As he puts it, “I thrive better in that type of environment. Instead of having somebody, you know, constantly looking over my shoulder, telling me what I needed to do and not.” 

He’s the sort of man that likes to have free reign to be as creative as he wants, to address problems in his way and in his own time. While he recognizes that his own methods don’t always work out as intended, he relishes the ability to experiment through trial and error on his own. 

“So that was what my first thought pattern or process—to try and get into owning my own businesses,” John says. “And that’s worked for me through the years.”

However, as with anything, it takes a lot of work and learning from one’s own mistakes to get where one wants to be.

Why His E-commerce Bootstrapped Business Didn’t Pan Out

Unfortunately, John’s first attempt at running his own bootstrapped business didn’t yield the success he was looking for. AutoClubHero, founded in 2013, was a subscription-based service that was intended to “help automotive owners pick up the slack basically where insurance and warranties fall short…[and] find ways of getting reimbursed for things that the insurance and warranties didn’t.”

He would later begin selling a few products to increase his overall revenue stream, but, by his own admission, “it did not go well.” Although the product development side of AutoClubHero burgeoned and John says they could have pushed to generate fleet sales, the subscription-based pricing model ultimately handicapped the business.

“We decided not to invest any more time or money into AutoClubHero for the time being,” John shares. He spent a total of $75,000 on this endeavor, none of which he was able to recoup. After selling their home, he and his wife were able to bounce back and get back on their feet.

Once AutoClubHero was placed on hold, John found that he was still left with a fair amount of inventory from the products sold through that site. So, he had an idea.

“I created a vehicle emergency survival kit,” he says, “and [it was] the biggest and most packed kit you can get on Amazon. It was the most expensive too, but in the first year we went from $25,000 in sales to over $100,000. It just took off like crazy.”

Yet even this relative success had its setback, coming in the form of changes to Amazon’s review system. According to John, “my rankings were doing really well, and I had authentic, genuine reviews, but they cut over half of them because their algorithm picked up keywords and phrases that they thought were not legitimate. So, immediately, overnight, I lost half of my sales.”

Afterward, he would make the shift to fleet sales, selling thousands of his kits to clients such as the FAA and Nevada Emergency Division. 

Lessons Learned in the E-commerce Space 

Despite the setbacks he encountered while running his bootstrapped business, John is grateful for his lessons. His primary takeaway has been that jumping in at the deep end of a market you don’t completely understand isn’t usually wise and can set you up for failure. “I dived into something, figuring I’d educate myself on all of that,” he says, “but I didn’t, unfortunately, learn the lesson of reaching out—which I do now—and get good, wise advice from people who’ve already been there.”

He found that the membership portion of his site was something he didn’t know well enough to make successful. As a result, his attempts at both traditional and social media marketing didn’t pan out. “I wasn’t reaching the right audience. And so those were some of the biggest things that I would say I could have learned better. Now, I reach out to people who knew what they were doing.”

Why He Decided to Pivot and Acquire a Content Website 

After his misadventures in subscription-based services, John began looking into other avenues. Several months prior to the acquisition of his content website Line25, he and his wife considered buying a storage facility. He says, “we had been studying self-storage for a couple of years, and that was going to be the investment platform we wanted to put money and time and effort in. But we didn’t see the ROI as we saw in digital, online assets.”

Even aside from potential ROI, John was looking for a field in which he could remain as independent as possible and avoid being dependent on other people. A content website that he could run himself from top to bottom was a perfect balance between potential revenue and professional freedom. 

What He Looked for Before Deciding to Acquire Line25

In addition to his desire to work independently, John wanted to find a business in a field that he both understood and had an interest in. “Graphic and web design have always been an interest to me,” he says, “So I’m a creative. I like designing, creating and coming up with ideas. So in that regard, that’s why we looked in the content space and, specifically, Line25 and web design development.”

He went on to say, “I was also looking for something that had a value-add element to it…basically something that needed some fixing up, [that] I needed to put some time, money and sweat into redesigning the site, cleaning it up, building backlinks, doing stuff like that.”

“What we were looking for was a site that had some authority in its space and a value-add opportunity, with the potential to increase the revenue and update the sites with better UX or user experience design; a site that had already been established, basically.”

With these criteria in mind, through working with FE International John was able to find a great fit in Line25.

His Approach to SEO and Elevating Line25 

Being new to the field, John does not consider himself a pro when it comes to SEO and running a content website. Following his own advice, he has reached out to others more experienced than himself for guidance. He says, “I’m still learning, and I’ve learned a lot. I’ve got my mind kind of wrapped around how it all works by reading and studying. And I think we’re doing a good job because we’ve been posting some content that’s getting picked up and ranked right away on page one of Google. So I’m pretty proud and excited about that. I think we’re on the right track.”

Advice for Becoming Successful at Affiliate Marketing 

John has come a long way from his first bootstrapped business to the acquisition of his first content website, and he’s learned a lot since then. When asked for what advice he would give, he emphasized the importance of forming partnerships and maintaining clear communication with business associates. 

One great success for Line25 has been its partnership with Adobe. “They reached out to me, which was really cool. I cultivated that through email, and sure enough, we got signed up with them, and that’s been a really great new affiliate relationship that we were able to establish.”

He also advises the proper cultivation of links on your content website, making sure to include affiliate links as often as possible. He says, “I think most people would realize it’s about building a good value in your content so that people trust what you’re saying and click the link to go check it out.”

Tips for Bootstrappers & Other Entrepreneurs Who Want to Succeed in the Content Space 

In addition to the previous advice he offered regarding learning from others, John also suggests that those looking to break into the content space do their best to avoid “analysis paralysis” and make a move even if it’s something on a very small scale, especially when one is just starting out.

At the same time, the lesson he would impart that he learned the hard way is not “to go in too deep and bite something you can’t really chew…Start out small, learn from others. Be willing to spend a little bit of money on some quality, reputable advice.”

John speaks from experience when he says that one should “just have courage. If you’re going to go for it, stick to it. It’s not humiliating to fail. It’s not a bad thing. That’s how we learn.”

If you are considering acquiring an online business, there is ample insight and direction to be found in John’s remarkable journey. To take the first step, have a read through our post on how to buy an online business.

Want to learn more about the Advertising & Marketing Solutions industry? Check out our 2024 Market Report.