5 Years In The Making, How I Make $50K/Month Through Blogging And An Agency

Published: May 22nd, 2023
Forrest Webber
Digitail - Wander...
from Austin, TX, USA
started September 2017
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Hello! Who are you and what business did you start?

Hey everyone. My name is Forrest Webber (2 R’s, 2 B’s), and I’m… well…

It’s always hard to answer this relatively simple question. I guess I can tell you what I do instead:

I own and manage a portfolio of about 20 content niche websites that generate $25-50k in revenue every month. In the last 30 days, I’ve published 275k words (mostly blog posts) – the kicker is that I didn’t write a single one myself.

Over the years, I’ve assembled an all-star team (30+ contractors and employees) of content writers, editors, designers, and copywriters that can take my ideas and turn them into income-generating assets.

My job description is closer to that of a leader than a technician; I facilitate communication between our organization's different departments and ensure the overarching vision remains at the forefront. This allows me to indulge in my creativity without sacrificing execution (ironically, for an entrepreneur, I’ve always struggled with execution…)

I was overstaffed in the early days, increasing my business risk but keeping my work hours within a tolerable range. I have two young daughters, one is seven years old, and the other is 5. I went through a divorce in 2019.

My personal life is essential to me. Many claim that much sacrifice and time are needed to build a business from scratch.

I say– it depends.

Building a team from day one and insisting on their continued growth, development, and autonomy required a different toolset, but ultimately got me where I wanted to be, and while it took a few years, it didn’t take an absentee father or workaholic.

Recently, I decided to make my team available to the public. So I built an Agency tailor-made for income-producing blogs.

Simply put, I want those interested in building and growing their online presence to have the tools I didn’t have but needed when I was starting. So, everyone reading this can rent my team and use it to launch their blogs, transform their side hustle into a viable business or create more free time.

Digitail.co, my agency, offers content, backlinks, SEO research, and even turnkey websites to blog portfolio owners like myself but also to “neophyte” bloggers who want to skip the first 6-12 months of growth and painful learning.

The same field-tested system I have used for my websites. And it works. It works so well we have one of the highest retention rates in the industry. That’s why one of our mottos is: “Digitail is the last agency you’ll ever hire.”

This is the result of a 5-year journey… that finally paid off.


What's your backstory, and how did you come up with the idea?

As I said, it’s been five years since this journey in digital land began. Five years since I bought the first blog, which eventually changed my life and brought me closer to semi-retirement.

You might’ve noticed I wrote “bought”. I came into this space with the mindset of an investor looking to acquire assets. Websites like Empire Flippers and Flippa were (and still are) marketplaces for buying and selling websites, and I spent a good chunk of 2017 lurking and hunting for deals.

See, this was a natural environment for me.

Before that, I was doing well for myself in real estate. I was well-versed in negotiations, raising capital, and managing deals effectively. Without boring you with the details, I had a big payoff after selling most of my properties. 100% of this money was funneled into websites.

You might think it was a risky, bold move.

After all, I could’ve easily stayed where I was, buying and flipping my way to a big pouch of gold. Yet, life had other plans.

My first-born daughter surprised us. She was born Christmas Eve, just over 3+ months early. We were displaced in Seattle and spent over 100 days in the NICU. After living inside a hospital for four months, I realized the value of being able to work from anywhere you are, as long as there’s wifi.

My new goal was to create a business that was entirely location independent so that I could handle 100% of my work from my laptop.

Ultimately, it worked out but not without a few bumps in the road. Where most new bloggers struggle for 1-3 years until they generate enough revenue to replace their job, I was making $5k my 1st month in business… but I didn’t know what I was doing for the most part. This was the secret to my success since I had to network and find the right individuals to help me maintain and grow my business.

Take us through the process of building the first version of your product.

Here I am (early 2018) with two websites making at least four figures without lifting a finger. Passive income. That’s the dream, right? I quickly realized that traffic, the most important metric for a blog’s longevity, would go to 0 if I didn’t publish more content. More content than I could write myself.

After all, the days when a solo writer could grow a blog are, for the most part, gone. You need a clear and efficient content strategy:

We focus on building the topical authority of our blogs.

The idea is to cover one topic from all angles, adding moats that protect your asset from the competition. Quality is more important than quantity in this case, even though today we have the luxury of publishing 1000s of words daily.

Even if I had a chance to do it all over, my strategy wouldn't change much. To be more specific:

Plan 2-4 months of content on a mind map (not 6 or 12 months; shorten your timelines and SEO changes rapidly)!

Spend time researching and defining the objective of each blog post, ensuring alignment between search intent and search results. People who search for "best pans for stir fry" don't want to read about cooking methods in the same post!

Before even publishing, have a system in place for on-page optimization, images & design elements, for engagement and CRO (yes, collect emails from day 1)

Focus on E-E-A-T. This IS something I'd do differently in 2023. When you can generate content with one click (i.e, LLMs and ChatGPT), the unique perspective of human writers with authority in their respective niches matters. It becomes vital if you want to generate organic backlinks (you should).

Having said that, you shouldn't shy away from these AI tools. They'll change our industry. Today, you have a unique opportunity to be one of the early birds. Remember that you must still cover basic SEO etiquette regardless of how you write or generate content.

As you can see, I couldn’t do all of that alone!

I started looking for partners, writers, and virtual assistants to help me. My initial passive investment strategy wasn’t working well, and I was in the manager role.

Eventually, I partnered with a rare individual with exceptional operations skills. Alongside him, we built a team and a system that turned these two websites into 20 and the $5k into $50k per month (in case you’re wondering, monetization is ~75%+ through ads via the Mediavine network). This was working well.

Double down on what you know, delegate what you don't know, and always assume there are unknown unknowns.

Light bulb moment. Why not offer our digital solutions to people in the same position I was in 5 years ago?

We began brainstorming the nature of our offer, listing the significant roadblocks new blogs encounter in their first 6-18 months. We focused on the two cylinders driving our operational engine – content and link-building. This is where we knew we could make a big difference and maintain a cost-controlled solution that damns near guarantees a positive ROI.

The goal was to streamline researching and writing posts and then landing backlinks. Since we work with in-house writers and SEO editors, we have an edge in cost-controlled production. That was our unique selling proposition in those early days.

We had to deal with the growing pains during the first year, shaping and fine-tuning the packages we were offering. The most important thing was aligning our brand with the businesses we wanted to work with. We were looking for long-term collaborations because we knew that content-heavy blogs - our expertise - take time to grow. To do that, we had to update our website and marketing plan.

Describe the process of launching the business.

Digitail 2.0 took shape in 2022.

We employed our creative department to redo our website, focusing on brand identity and consistency across the board.

It took us ~3 months to launch the new website. That included research, design, homepage video recording, web copywriting, and email sequences (welcome and nurturing emails).

The design is clean and fits our style (green is the color of growth and harmony, by the way), allowing the web copy to pop. Plus, the very name, Digi-TAIL, is a little cipher on its own, hinting at our core message: Team and Efficiency for Long-tail results.

Our homepage is scroll-full, with each section packed with information that moves the prospect toward a purchase. It’s optimized for conversion under specific parameters. One of the issues with Digitail 1.0 was that we tried to be everything for everyone, which caused scaling and communication issues.

In its current iteration, our agency pre-qualifies prospects by fine-tuning the message. For example, phrases like “If you aren’t generating at least $1000 per month…” or “delivered in 2-20 days'' are soft parameters we want the potential client to know!

But by far, the most significant change was changing how we set up our offers

If you visit our page, you’ll notice that we have multiple choices for content creation that span from regular articles to a full-blown content calendar. This way, we can calibrate our strategy so it fits your goals, budget, and expectations.

It was a key change that finally allowed us to simplify the onboarding process and reorganize how we approached work with each client.


We also optimized each service page for conversion, with a unique email sequence on top of it to guide subscribers through a buyer’s journey.

I decided to take a hands-off approach focusing on lead generation and networking. My first step was adding content to my personal website and slowly growing my Twitter account.

It’s a platform that suits my style. I've connected with brilliant people and learned from them.

While I joined in 2017, it's only during the last ~6 months that I could hone my message and gain over 600 followers. Twitter is about authenticity. Talking about the technical side of the business didn't help me grow or connect with the right individuals. I attracted like-minded individuals when I began tweeting (you do need to tweet a lot, by the way...) about the struggles of managing people and investing in digital assets.

My #1 priority nowadays is facilitating smooth communication between the client and my team.

As you can see, our launch was unusual. Instead of a hockey stick, 0 to 100 growth spurt, our foray into the markets took two years to mature and a lot of capital reinvestment from my blog portfolio.

(I feel that it’s an important point to highlight. A massive launch isn’t always the case. For us, it was more about reorganizing and optimizing how we delivered our services)

We continued to serve our existing client base on all fronts. Our team delivered over 500k words of human-written content and nearly 300 links every month.

With a new and improved Digitail, we were looking to expand. We finally had our production line working. After ~7 months, we saw a '300%' growth in revenue for Digitail.

Since launch, what has worked to attract and retain customers?

What we DIDN'T do (yet):

  • Facebook / Google ads
  • Sponsored newsletters
  • Mass outreach

Nothing wrong with the above, and we'll incorporate them in the future. The real catalyst was getting out there and just talking to people. Plain and simple.

We leveraged our connections to generate more leads but didn’t do the typical mass cold email outreach. As I’ve mentioned numerous times, we want a specific kind of client, and a scattershot approach doesn’t always work.

As I've mentioned, we built Forrest Webber to help people start their first blog – another marketing channel that helped people get to know my team and me before jumping on board.

But the real growth happened organically and through my network.


I've had the pleasure of being a guest on several podcasts. I got to tell my story (the one you're reading right now) and hopefully help a few people.

One that directly impacted our sales was Niche Pursuits with my friend Jared. No sales funnel, no extreme direct response marketing. Just two colleagues are talking to each other, sharing insights.

And yet, that's all it takes if your backend systems are in place. For us, it’s three different stages when communicating with leads.

  1. Getting-to-know stage, where we utilize plain ole emails to understand their business but, more importantly, set up a meeting.
  2. Pitching. Video calls and presentations via Google Docs and Sheets.
  3. Onboarding process using the Service Provider Pro platform.

Simple, don’t you think?

Another significant change after the launch was consolidating the team in our offices in India.

During the first few months, our writers and editors were dispersed worldwide. Although a decentralized approach may be practical in many cases, we wanted to upgrade the quality of our services, manage every aspect of our operations, and control our costs.

It took hard work and capital, but with the help of my one-in-a-million business partner overseeing everything over there, we now have our headquarters.

While I love the freedom of working from anywhere in the world, there are some downsides. So, I was thrilled when we found our core members who were more than willing to work in that new environment.

Determine what you want, and comprehensively fix your (inner) eyes on the prize.

Today, our team works under the same roof. Different departments can communicate directly and in real time. We immediately noticed an uptick in consistency, faster turnovers, and even more creativity.

It was a blessing! SEO is inherently volatile, and recently Google made it even harder to have a rigid strategy. This kind of efficiency with our team has helped us create deep moats around our operations. We can course correct faster than most agencies and adapt to these changes without batting an eye.

It’s not that we don’t get hit by the algorithm. We do. We ensure honesty and ground our client’s expectations in reality. But over the months and years, we’ve showcased longevity, consistent growth, and a slight edge in the performance of our SEO campaigns due to managing a team hands-on.

Take our blog in the book niche, for example. It’s one of the first ones I bought, and we have grown from 50-70k sessions a month to around 250k+ sessions now while publishing 10-15 articles every month.


For keyword research, we mainly focus on building the website's topical authority while simultaneously maximizing our overall efforts by going after deeper, long-tail, and low-competition keywords relevant to the topic. That is giving us an early edge while we work on ranking for more competitive KWs.

Another example (dreamsandmythology.com) where we focused on easy KWs, but eventually we became competitive and practically doubled our traffic in a couple of months:


I’d argue that our magic formula is our extensive keyword research process. We use it to dazzle our clients and improve their SERP. It goes like this:

  • Do competitor research and find keywords that we can rank for.

  • Content gap analysis with our competitors to ensure our footprints are as strong or better as our primary competitors.

  • We look for GSC data and try to find and optimize keywords where we are ranking between the 10-30 range.

  • Apply advanced strategies like custom regex search in GSC to find questions and map out the website structure based on the relevant keywords (think silos and interlinking)

When doing keyword research and content planning, our editors follow a specific checklist (some items omitted, of course):

  • Does the keyword fit in our topical map?

  • Do we have enough authority compared to the competition to reasonably rank for it within a certain period?

  • Does the search intent match the type of content that we are planning on creating? For example, if a search result has mostly e-commerce pages ranking, there is very little chance we will rank despite having good content for the keyword.

  • We like to maintain a mixed ratio of affiliate/info content and try to create at least 50% minimum to an average of 60-70% informational and helpful content so that we are not considered a thin affiliate website.

  • While we do not create a lot of content on ZSV keywords, even though that has been picking up trend lately, we do not care for having a very high volume as long as the content fits our topical map.

How are you doing today, and what does the future look like?

The plan I have today is straightforward:

The blog portfolio hovers around $35k MMR (though currently, it’s at $30k MRR due to low Q1 RPMs). I aim to increase reinvestment from 30% to 40% and grow the smaller websites faster.

Regarding agency work, we’re looking at $60k MMR, with a profit of 10%-30%. It’s above the market average, but we’re trying to make our operations even more efficient by focusing on a handful of services (the BIG needle movers).

We’re delivering ~1.2 million monetized monthly sessions (counting only the numbers from Mediavine). Hopefully, this number will double in the next 6-18 months.

Through starting the business, have you learned anything particularly helpful or advantageous?

I'm an ideas person. Most of you would consider it an advantage for starting a business. In my opinion, it's a double-edged sword. I've made many mistakes trying to reinvent the wheel when I already had a winning strategy.

I’ll share a humbling story in a moment, but if I were to dictate a bullet-point list of lessons I would teach my younger self, it would look like this:

  • Determine what you want, and comprehensively fix your (inner) eyes on the prize.
  • “Your Faith is Your Fortune” (Nevile Goddard).
  • Systems and Processes are crucial, but stay alert to Human Capital.
  • In the end, contributing brings you the most Eudaemonia.

Now, to the story. In 2018, when ecom was booming, I decided to add an e-shop to my blog portfolio. I assumed my previous successes in picking winners would translate well into this new venture. A mistake. A $300,000+ mistake.

The business failed so spectacularly that I considered the possibility I got scammed during the acquisition process. The reality? I was blindsided by my track record, never once considering that my idea would flop.

It wasn't until I found my business partner, Mohammad Qaiser, that I witnessed the power of doing a few things right and then scaling. And, of course:


If I had to condense all of the above into a simple message:

Double down on what you know, delegate what you don't know, and always assume there are unknown unknowns. Once you have a stream of income that can cover your expenses, you're free to shoot for the stars.

What platform/tools do you use for your business?

Of course Ahrefs for SEO. Although it can be pricey for newcomers, it’s an invaluable tool for more extensive blog portfolios.

ConvertKit for emails. Visual automation is a lifesaver when you start A/B testing and segmenting multiple lists of 1k+ subscribers.

I use Hyperfury for Twitter. You’re able to schedule threads, RTs, and even replies. Plus, trigger automatic replies under tweets that do well.

Then, for internal communication, I was using Slack but eventually switched to Basecamp for the project-based organization.

Honorable mention… ChatGPT. It’s important to keep up with how these LLMs evolve since they’ll undoubtedly influence the digital landscape.

Keeping your tool stack lean is always preferable for practical and psychological reasons. You can quickly lose track of what’s essential and overanalyze what’s the best tool to use. Try all of them but stick to a handful.

What have been the most influential books, podcasts, or other resources?

  • 4-hour workweek - Tim Ferriss (I learned about VAs, and efficient systems, along with lifestyle design)
  • Virtual Freedom - Chris Ducker (Practicals about hiring and overseeing VAs)
  • E-Myth Revisited - Michael G (How to visualize and then build an Organization that can run without you)
  • HBR’s “On Managing Yourself” Book - Especially Chapter “Who’s Got the Monkey?” (How to properly lead and manage with less time)
  • Blog - DollarSprout.com - Jeff and Ben (heroes of mine in the blogging space, they showed me how much money could be made)

Most people don’t know this, but I’m interested in dreams, myths, and Jungian psychoanalysis. I even started a passion project called dreamsandmythology.com. Sometimes the most helpful guide is your unconscious mind.

Advice for other entrepreneurs who want to get started or are just starting out?

Check whether you've outgrown your original role. Michael Gerber, in his book “E-Myth Revisited” talks about three distinct personalities:

The Technician. The Manager. The Entrepreneur.

There will be a point in your career where you must jump from writing, designing, posting content, taking calls, researching, etc, to managing others. If you don't switch roles, you'll end up micromanaging or wasting your potential, which can seriously harm the health of your business long term. Get dirty early on! Get into the trenches and understand your business inside out.

Learn to separate the responsibility of tasks effectively. This is a concept borrowed from Adlerian Psychology. Everyone’s charges are their own– handling someone else’s duties is not your job. It will bring you tremendous joy to serve and assist others in their tasks– when you want to.

But learn the difference between your tasks and theirs, and don’t fall for the “mend my life” cries that can often surface– especially when you’re good at helping others. This was critical for me– and true in all life areas, not just business.

Finally, get ready to meet the real you. Most entrepreneurs will confirm that their biggest obstacle was their own self. The bad, the dark, the ugly. Psychological complexes surface only when we put ourselves under immense stress.

To think that you'll be able to come out the other side without a few war wounds is an illusion. In the end, it's all worth it. Whether you succeed or not.

More tips stemming from the above:

  • To manage others is to manage yourself.
  • The growth of your business will help you grow too.
  • Look for talent, character, and communication when hiring. In that order
  • Don't force people into roles, but do assign roles to people

Where can we go to learn more?

If you have any questions or comments, drop a comment below!