How Brett Helling Built a Successful Lifestyle Business Through Website Acquisitions

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How Brett built a lifestyle business through acquisitions

While everyone loves a good success story, achieving success usually involves overcoming obstacles and bouncing back from failures. Today, we have a very insightful and honest interview with Brett Helling.

Although Brett has built a portfolio of profitable websites including Ridester, BloggingTips.com , and Gigworker, he’s faced some significant challenges and setbacks along the way.

As you’ll read in the interview, Brett’s first few sites failed. His first major success came through an acquisition that involved changing the direction of the site he purchased. That move paid off, as the site reached up to 1.5 million visitors per month and became a leader in its industry.

Brett has grown mostly through acquisitions, as he’s purchased about 20 sites over the years. Some of the sites Brett purchased were merged or redirected to other sites in his portfolio. Today, he owns about 13 different sites, although he focuses primarily on the three mentioned above.

In the interview, Brett shares why and how his outlook on acquisitions has changed over the years and what he’s doing in a post-HCU (Helpful Content Update) world. You’ll see how pivots have allowed Brett to continue running a profitable business after major setbacks from the COVID pandemic and damaging Google algorithm updates.

Brett also shares his thoughts on what he would do differently if he had to do it all again.

Please tell us about your background and how you got started with online business.

I started playing around with websites as a hobby while in college. I really like building things and seeing them come to life as the result of hard work, so websites interested me.

After watching nearly every YouTube video I could find on the topic, I tried my hand at building many different websites – probably 10 or so – and every single one failed miserably. However, I kept going simply because I liked the process of building them.

I was also a rideshare driver during this time. It was a fairly new concept and I realized that there wasn’t a lot of information available to drivers who wanted to learn how to be successful while driving. So I launched a small personal blog to share what I learned behind the wheel with other drivers.

It was actually this website that began doing very well, and eventually became the main focus of my online efforts.

What was your first acquisition, and what led to it?

In my time messing around online, I bought a few small sites from Flippa that really aren’t worth mentioning because all of them failed. I also got scammed out of $10,000 by somebody who spoofed the traffic numbers and domain authority.

After emotionally working past those failures, I noticed a web-based ridesharing platform called Ridester within the classifieds section of Flippa. To my surprise, the domain had links from very powerful, well-known websites like Forbes.

Ridester website

I ended up buying the site and platform from the founder and pivoting from a rideshare platform to an informational blog. I merged the previous blog that I had been writing on with the new Ridester.com domain, and a new project was born.

Within 3 years, the site achieved a traffic high of 1.5 million unique visitors per month and served as one of the largest driver acquisition sources for Uber and Lyft.

Why do you prefer acquiring existing websites/businesses rather than starting from scratch?

Prior to the Helpful Content Update, I preferred acquiring existing websites instead of starting them from scratch. This was mainly to avoid having to build links, but also to capitalize on the fact that it’s usually easier to optimize underperforming content than to rank it from scratch.

After a few of my biggest sites got caught up in the Helpful Content Update in September of 2023, I’ve shifted my thoughts on that.

I now realize that acquiring large existing websites may not be as risk-averse as I had previously thought, as Google has made it fairly known that they have no issue with completely wiping reputable existing sites off the map – even if they have great content, decades of experience, and tons of high profile links. 

Have you used any investor money for acquisitions, or do you just reinvest from the business’s earnings?

I have never taken investor money for my websites. I usually just bootstrap my business growth using cash flow from the existing businesses. I’m sure I might be able to grow quicker with institutional money, but if I go that route, there comes an added level of responsibility, pressure, and timelines that I don’t necessarily have to deal with when I’m only accountable to myself.

What monetization methods do you focus on?

I have previously relied on ad networks, but within the past year, I’ve begun to try to pivot to other monetization methods like lead generation and services.

I think ad networks will always have a place within monetization, but as the search engines continue to increase the importance of user experience, the need to diversify monetization channels becomes increasingly more important.

Gigworker website

Where do you find the websites and businesses that you acquire?

I like to consistently look on Flippa for websites in the $10,000 – $50,000 range. I have found quite a few projects in that range that were high-quality yet the founders simply didn’t have the time, knowledge, or budgets to achieve escape velocity and take their projects to the next level.

I usually look for stressed assets that are underperforming. Granted, there’s quite a bit of work to do on these sites, but once I do, I can usually see some good results.

I have also started finding some interesting projects on Little Exits. As I shift my focus from high-traffic content sites to smaller service-based businesses, I find myself spending a considerable amount of time there trying to find projects I can grow using strategic SEO campaigns.

What do you look for in a potential acquisition?

As I mentioned above, I like to look for websites that have “good bones” so to speak, but that are underperforming. Usually these are projects that the founders lose motivation with or don’t have the time to commit to take them to the next level.

In terms of website metrics, I like to look for sites with a clean white-hat link profile, that have been earned organically and naturally with little to no outreach. These sites usually earn these links through high-quality content or some type of edge that competitors don’t have.

I also look for assets that were started as a result of the founder’s passion, not simply to make money. These types of projects are usually packed with expertise and credibility that I can use to my advantage – as a foundation to build on top of.

What are some of the advantages you have by owning a large portfolio of sites rather than focusing on a single website?

Honestly, if I were to do it all over again, I would spend the majority of my time on one project instead of a portfolio. I previously wanted to grow a huge portfolio but as I did so, I began to understand how difficult it is.

People don’t just want content. They want interesting content that truly provides expertise. Unless you’re building a huge team that actually reviews products, engages in actions that you write about on the sites, or is physically in the industry you’re covering every day, the expertise is going to be minimal, which will result in subpar content.

However, if you spend your time and focus on just one, or even two, or three sites at most, you’ll be able to truly build a brand that will stand the test of time.

BloggingTips.com website

What is your process for managing so many different websites?

To manage so many different websites, I began to hire a large team in 2019. The end goal I was working toward was to have a Manager for each website. This would be somebody in the weeds who had a granular understanding of each website.

As I began to hire for these positions and build a team to oversee the portfolio, COVID hit. I had to temporarily pause the plans until 2022 when the sites started bouncing back and the economy seemed a bit less uncertain.

At the very end of 2022, I began scaling the portfolio once again. I was seeing really good results as a result of my work, until…. Google released the Helpful Content Update in September 2023.

Once more, I had to let the entire team go and let things shake out and figure out what was next. Since that time, I’ve been able to retain a few core contractors, but have largely been doing the work myself because my cash flow has been down.

I’d like to scale once again, but at this point, the idea of just having a small lifestyle business that does marginally well, somewhat passively once built, is becoming more appealing than running a large team.

What would you say are your strengths that have helped you succeed?

I think my biggest strength that has helped me succeed is my unrelenting work ethic and grit that it takes to persevere through hard times.

There have been multiple times that I have woken up, much to my surprise, to find that my income has completely dried up overnight. This happened when the government announced COVID-related lockdowns in 2020 and again when the Helpful Content Update was released.

Instead of panicking (there was a bit of that initially if I’m being honest) and completely giving up, I simply put my head down and did the work necessary to survive.

Just like I bounced back from the hit during COVID lockdowns, I anticipate bouncing back from the HCU. I’ve gutted my sites and pretty much rebuilt them from scratch, so hopefully my nearly year of 60 hours weeks will eventually pay off.

What are some of the biggest challenges you’ve had to overcome with the business?

As I mentioned above, it is very difficult to wake up one day and find out that your income has pretty much gone away overnight. It is hard to describe the feeling of a punch to the gut that this brings.

It’s really, really, really hard to build a brand, let alone a long-term business that is fairly recession and update-proof. If you’re in this industry, you need to understand that it comes with the territory.

I’d suggest that somebody just getting into this business, or a newer player who hasn’t been through a situation like this yet, mentally prepare for this happening to you. It’s not a guaranteed thing, but it will more likely than not eventually happen in some way or another.

I would suggest saving as much as you can now, as well as diversifying traffic and monetization channels so you’re prepared if you have to wind things down for a while. Even if you don’t, it doesn’t hurt to take this step no matter how well you’re doing.

Do you have an exit strategy for your websites or portfolio?

I have purposely not built an exit strategy into my businesses. I personally believe that if I plan to hold my websites forever, there’s really no way that I’ll skimp on quality or not do the work necessary to keep them growing.

I have sold websites before, but that was simply because I lost passion for the projects and they no longer interested me. I now try to only work on sites that I’m very passionate about and think about every day – to the point of borderline obsession.

My thought is, if I am that passionate about my sites, there’s really no limit to what I can achieve with them. And if the right buyer comes along at the right time, I’ll consider selling. But until then, I’ll continue working on the sites and love doing so every day.

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