Brett Helling owns several profitable websites, including Ridester, BloggingTips.com, and Gigworker. But his journey to success wasn't smooth. He faced many failures and challenges before building his current online business.
Brett started making websites as a hobby in college. His first attempts all failed - he created about 10 websites that didn't work out. Instead of giving up, Brett kept trying. While working as a rideshare driver, he noticed there wasn't much helpful information for other drivers. This led him to start a blog sharing his experiences, which became his first successful website.
As his online business grew, Brett mainly expanded by buying existing websites. He's purchased about 20 sites over the years. Some of these he combined with other sites he owned. Today, he manages about 13 different websites.
This article will explore Brett's journey in detail. We'll look at how he got started, his biggest wins and setbacks.
Brett Helling
How It all began
Brett Helling's journey into the world of online business started during his college years. Like many students, he was curious about the internet and how websites worked. This curiosity led him to start building websites as a hobby. He didn't have any formal training or experience, but he was eager to learn.
Brett's early attempts at creating websites weren't successful. He made about 10 different websites, and every single one of them failed. These failures might have discouraged some people, but not Brett. He enjoyed the process of building websites so much that he kept going despite the setbacks.
During this time, Brett was also working as a rideshare driver to earn money. This job turned out to be more important to his future than he initially realized. As he drove passengers around, Brett noticed something interesting. Ridesharing was a new concept at the time, and there wasn't much information available for drivers who wanted to improve their skills and earn more money.
Seeing this gap in information, Brett had an idea. He decided to start a small personal blog where he could share what he was learning as a driver. He wrote about his experiences, offered tips for other drivers, and shared insights about the rideshare industry. This blog was different from his previous attempts at websites because it came from his real-life experiences and provided valuable information to a specific group of people.
To Brett's surprise, this blog started to do well. People were finding it useful and visiting it regularly. Without realizing it at first, Brett had stumbled upon a successful formula: providing helpful, experience-based content to a niche audience. This small blog became the foundation of his future success in online business.
Brett's first big win
Brett's first major success came when he bought a website called Ridester. While browsing Flippa, a marketplace for buying and selling websites, Brett came across a listing for a web-based ridesharing platform called Ridester. What caught Brett's attention wasn't just the website itself, but the impressive backlinks it had. Ridester had links from well-known and respected websites like Forbes. In SEO (Search Engine Optimization), these kinds of high-quality backlinks are very valuable.
Seeing the potential in Ridester, Brett decided to buy the website and its associated platform from the original founder. However, Brett didn't just keep running Ridester as it was. He had a different vision for the site. Instead of continuing as a rideshare platform, Brett decided to transform Ridester into an informational blog.
This decision to change Ridester's direction was a pivotal moment. Brett took the successful formula he had discovered with his personal rideshare blog and applied it to Ridester on a larger scale. He merged the content from his previous blog with the newly acquired Ridester.com domain. This move combined the valuable content Brett had been creating with the strong domain authority and backlinks that Ridester already possessed.
The results of this strategy were impressive. Within just three years of acquiring and pivoting Ridester, the site's traffic grew enormously. At its peak, Ridester was attracting 1.5 million unique visitors every month. This level of traffic is significant for any website, but it was particularly impressive for a niche site focused on rideshare driving.
Moreover, Ridester's success went beyond just attracting visitors. The site became one of the largest sources for driver acquisition for major rideshare companies like Uber and Lyft. This means that many people who decided to become rideshare drivers were finding and using Ridester as a valuable resource in their journey.
Buying websites instead of starting new ones
After his success with Ridester, Brett Helling adopted a new strategy for growing his online business. Instead of creating new websites from scratch, he focused on buying existing ones. Over the years, Brett has purchased about 20 different websites. Some of these he kept as separate entities, while others he merged with existing sites in his portfolio. Today, Brett owns about 13 different websites, with his main focus on three: Ridester, BloggingTips.com, and Gigworker.
Brett prefers buying existing websites for several reasons. First, it allows him to avoid the difficult process of building backlinks from scratch. In SEO, backlinks (links from other websites to yours) are necessary for ranking well in search engine results. Established websites often already have a good backlink profile, giving them a head start in search rankings.
Secondly, Brett finds it easier to improve existing content than to create and rank new content from scratch. When he buys a website, he can look at what's already there and find ways to make it better. This might involve updating old information, expanding on topics that aren't covered in depth, or improving the writing quality.
When looking for websites to buy, Brett has a specific strategy. He looks for what he calls "stressed assets" or websites with "good bones." These are sites that are underperforming but have potential. Often, these are projects where the original owners have lost motivation or don't have the time to take them to the next level.
Brett typically looks for sites in the $10,000 to $50,000 price range. He searches for these opportunities on platforms like Flippa and Little Exits. When evaluating a potential purchase, Brett looks for specific qualities:
1. A clean, white-hat link profile. This means the site has earned its backlinks naturally and ethically, not through spammy tactics.
2. Links earned through high-quality content or some unique advantage that competitors don't have.
3. Websites that were started out of passion, not just to make money. These sites often have more depth and expertise in their content.
By focusing on these qualities, Brett can find websites that have a strong foundation but need some work to reach their full potential. This strategy has allowed him to grow his online business more quickly and efficiently than if he had tried to build each site from the ground up.
Making money from websites
Brett Helling's approach to making money from his websites has evolved over time. In the past, his main source of income was through advertising networks. These networks place ads on websites and pay the website owner based on the number of views or clicks the ads receive. This method can be effective, especially for sites with high traffic like Ridester.
However, Brett has realized the importance of diversifying his income streams. In the past year, he's been working on shifting towards other ways of making money. One of these is lead generation. This involves collecting information from website visitors who are interested in a particular service or product, and then selling this information to businesses who can provide that service or product. For example, on a rideshare-focused website, this might involve collecting information from people interested in becoming drivers and passing it on to companies like Uber or Lyft.
Another avenue Brett is exploring is offering services directly through his websites. While he doesn't go into detail about what these services might be, they could potentially include things like consulting, online courses, or premium content for subscribers.
Brett believes that advertising will always have a place in website monetization. However, he recognizes that search engines like Google are increasingly prioritizing user experience. This means that websites with too many ads or poorly placed ads might not rank as well in search results. By diversifying his income sources, Brett is not only potentially increasing his earnings but also protecting himself against changes in search engine algorithms or advertising policies.
Running many websites at once
Managing a portfolio of websites is no small task, and Brett Helling has experienced both the challenges and opportunities that come with this approach. At one point, Brett was overseeing about 13 different websites, with a primary focus on three main sites: Ridester, BloggingTips.com, and Gigworker.
To handle the workload of running multiple websites, Brett began building a team in 2019. His goal was ambitious: he wanted to have a dedicated manager for each website. These managers would be deeply involved in their respective sites, understanding the nuances of the content, audience, and performance metrics.
However, like many businesses, Brett's plans were disrupted by the COVID-19 pandemic. The uncertainty brought by the global health crisis forced him to temporarily pause his expansion plans. It wasn't until 2022, when his sites started to recover and the economy seemed more stable, that Brett felt comfortable resuming his team-building efforts.
Towards the end of 2022, Brett once again began scaling up his portfolio. He was seeing positive results from his work, and things were looking promising. But then another setback occurred: in September 2023, Google released a major algorithm update called the Helpful Content Update. This update significantly impacted many of Brett's websites, causing a drop in traffic and, consequently, revenue.
This latest challenge forced Brett to make some difficult decisions. He had to let go of most of his team and return to managing much of the work himself, with the help of a few core contractors. This experience has led Brett to reconsider his approach to running an online business.
While he once aspired to build a large portfolio of websites with a sizeable team, Brett is now considering the benefits of a smaller, more manageable operation. He's beginning to see the appeal of a "lifestyle business" – one that provides a good income and allows for a balanced life, without the stress and responsibility of managing a large team or numerous websites.
Big problems Brett faced
Throughout his journey in online business, Brett Helling has encountered several challenges. These obstacles have tested his resilience and shaped his approach to running his websites.
One of Brett's earliest setbacks occurred when he was still new to buying and selling websites. He fell victim to a scam, losing $10,000 to someone who had manipulated their website's traffic numbers and domain authority. This experience was not only financially costly but also emotionally draining. However, it taught Brett valuable lessons about due diligence and the importance of thoroughly verifying information when considering a website purchase.
But perhaps the most significant challenges Brett has faced have been sudden, dramatic drops in income. He describes the feeling as waking up to find that his income has "completely dried up overnight." This has happened to Brett twice in recent years, and both instances were due to factors largely outside of his control.
The first major income drop occurred in 2020 when governments around the world announced lockdowns in response to the COVID-19 pandemic. For Brett, whose websites were heavily focused on the rideshare industry, this was particularly devastating. With fewer people traveling and using rideshare services, traffic to his sites plummeted, taking his ad revenue with it.
The second instance happened in September 2023 when Google released its Helpful Content Update. This major algorithm change affected many websites across the internet, including several of Brett's. Once again, he saw his traffic and income drop dramatically in a very short period.
Facing these challenges required a combination of emotional strength and practical action. Brett admits that there was initially some panic, which is understandable given the sudden and severe nature of these setbacks. However, instead of giving up, he chose to "put his head down and do the work necessary to survive."
In response to the Helpful Content Update, Brett took drastic action. He essentially gutted his sites and rebuilt them from scratch, focusing on creating the kind of high-quality, helpful content that Google's new algorithm favors. This process has been intense, involving nearly a year of 60-hour work weeks.
These experiences have taught Brett lessons about the nature of online business. He now understands that such setbacks are part of the territory and advises newcomers to the industry to be mentally prepared for similar challenges. He suggests saving as much money as possible and diversifying both traffic sources and monetization methods to build resilience against future shocks.
What Brett learned along the way
Brett Helling's journey has been filled with valuable lessons. One of the most significant insights he's gained is about the importance of focus. If he could start over, Brett says he would spend most of his time on one project instead of trying to manage a large portfolio of websites.
This realization came from understanding what readers truly want. People aren't just looking for any content; they want interesting, expert-driven information that provides real value. Brett found that unless you're building a large team of experts who are actively involved in the industries you're writing about, it's challenging to provide the level of expertise readers demand across multiple websites.
Brett now believes that concentrating on just one, two, or at most three websites allows for building a stronger brand that can stand the test of time. This approach enables a deeper focus on quality and expertise, which is important for long-term success in the increasingly competitive online space.
Another key lesson Brett learned is the importance of consistency and hard work. He attributes much of his success to his strong work ethic and ability to persevere through difficult times. The online business world can be unpredictable, with algorithm changes, global events, and shifting user behaviors all potentially impacting a website's performance overnight. Brett's experiences have taught him the value of being prepared for these challenges and having the grit to work through them.
Brett also emphasizes the importance of financial preparedness. He advises new entrepreneurs to save as much money as possible and to diversify both their traffic sources and monetization methods. This approach provides a safety net and helps to weather the storms that inevitably come in the online business world.
Lastly, Brett has learned the value of passion in his work. He now tries to only work on websites that he's genuinely interested in and thinks about constantly. This level of engagement, he believes, is key to achieving the best possible outcomes for his online ventures.
Brett's plans for the future
Unlike many in the online business world, Brett Helling doesn't have a specific exit strategy for his websites. He's taken an unconventional approach by purposely not building an exit plan into his business model. Brett believes that if he plans to hold onto his websites indefinitely, he'll be more motivated to maintain high quality and continue growing them.
This doesn't mean Brett never sells websites. In the past, he has sold sites, but only when he lost passion for the projects and they no longer interested him. Now, he tries to only work on sites that he's deeply passionate about – to the point where he thinks about them constantly, almost to the point of obsession.
Brett's philosophy is that if he's that passionate about his sites, there's no limit to what he can achieve with them. He believes this level of engagement and dedication will lead to the best possible outcomes, whether that's continued growth or an eventual sale if the right opportunity comes along.
This approach reflects Brett's long-term perspective on his online business. Rather than chasing quick profits or looking for a fast exit, he's focused on building sustainable, high-quality websites that provide real value to their users. He believes that by doing so, he'll not only create more successful websites but also enjoy the process of running them more.
Looking ahead, Brett plans to continue focusing on his core websites, particularly Ridester, BloggingTips.com, and Gigworker. He's committed to rebuilding and improving these sites, especially in light of recent challenges like Google's Helpful Content Update. His goal is to create content that's not just optimized for search engines, but truly helpful and valuable for his readers.
While Brett remains open to opportunities that may arise, including potential sales if the right offer comes along, his primary focus is on continual improvement and growth of his existing properties. He's excited about the potential of his websites and looks forward to seeing how far he can take them with his passionate, dedicated approach.
Conclusion
Brett Helling's story isn't just about building websites. It's about learning from mistakes, adapting to changes, and never giving up. He started with failed attempts, faced big setbacks, but kept pushing forward.
What can we learn from Brett? First, it's okay to change direction. Brett switched from making many websites to focusing on a few he really cares about. This shows it's important to find what works for you, even if it means changing your plans.
Second, being ready for problems is crucial. The online world can change quickly. Brett faced this when COVID-19 hit and when Google changed its rules. He didn't give up but worked hard to fix things.
Lastly, Brett's approach teaches us about doing what we love. He now only works on websites he's passionate about. This keeps him motivated and helps him create better content.
For anyone thinking about starting an online business, Brett's experience is something you could learn a thing or two from. It won't always be easy, but with hard work and the right attitude, you can overcome challenges and build something successful.
Remember, there's no one-size-fits-all in online business. What worked for Brett might not work for everyone. But his story shows that with dedication and willingness to learn, you can find your own path to success in the digital industry.
