Don't Do It Yourself

Entrepreneur Spotlight Series: Forrest Webber

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     Entrepreneur Spotlight

Forrest Webber – Founder of and a digital marketing agency, Digitail.coForrest Webber Profile Picture

  • Favorite Tools & Services: Basecamp, Service Provider Pro (SSP), Ahrefs (why?)
  • Where He Finds Talent: Personal recommendations
  • You May Not Know: In addition to his 25 content sites, Forrest created a monetized blog for his passion, dreamwork and depth psychology.


“I own a business that's broken up into two main parts…my portfolio of blogs…and the machinery or the agency that runs everything.”

Forrest Webber is the owner of and digital marketing agency,, two parts of the whole that is Forrest’s business.

“I own a business that's broken into two main parts. It's my portfolio of blogs or content sites and then the machinery or the agency that runs everything.”

He joined us from a telephone booth to share some insights on how he has grown his portfolio of sites and digital marketing services.


Entrepreneur Interview Background

“I hope I can share a little bit with you that will convince you that this is the best business in the world to be in.”

Part one of Forrest’s businesses is a profitable array of blogs and niche content sites, which you can find more info on at

“So I own about 25 content sites that earn me around $75,000 per month.”

“In short, you have a basket of websites that is passive for me.”

Forrest got into this business after a successful career in real estate, where he learned a process that he has replicated in his corner of the internet.

“When I started my career in real estate, it was the same process. I built the property management leasing company to handle our student housing developments and assets so that eventually, I could work less and less right? That's what I've done in the website space.”

The Other Half of the Business – The Machinery

The second part of Forrest’s business is the digital marketing agency,

The site portfolio is part one of his company, while is the behind-the-scenes moving parts that create content for other sites. He refers to this as “machinery.”

“You have the machinery, and this is what took me five years to build.”

Since entering the site building and digital marketing world, he believes that it’s the best business to be in.

“I hope I can share a little bit with you that will convince you that this is the best business in the world to be in. Because I really believe it is.”

Living the Dream

“It helps me understand myself and the world a lot better, whic has been a hard journey for me.”

When it comes to personal interests, it would seem that Fleetwood Mac and Forrest have something in common.

“I'm obsessed with dream work and depth psychology and so Carl Jung and Joseph Campbell are my jam.”

He even started a blog to share his interest with the world.

“One of my first passion hobby blogs that's now a monetized blog is”

Forrest has since handed the blog over to a trusted writer with an interesting story himself.

“The writer that I've recruited for the site that's a subject matter expert lives in Sparta Greece and is a native Greek. His depth of insight into mythology is profound. I have learned so much from him.”

Dreamwork has not only been a hobby but has also given Forrest perspective.

“I'm really passionate about that topic. It helps me understand myself and the world a lot better, which has been a hard journey for me.”

Finding Talent

Entrepreneur Interview Background

Favorite Place to Find Talent: Personal recommendations

“Hire yourself in every position until you're ready to outsource it.”

“You typically think I would say something like Upwork or Fiverr. But I've had a shift in my business model in the last two years that's been very profitable and very productive.”

“If you're considering how to find talent, I would start with a model of what you want your organization to look like in five years or at least two years. If you picture an organizational chart, write out every member that needs to be a part of your team in 2-5 years, and then write your own name underneath each role.”

“Create a role description for what that person needs to do, what they're accountable for, and what kind of strengths they need. Hire yourself in every position until you're ready to outsource it and run those jobs for a while with those mentalities. Put that hat on.”

Forrest's Toolkit

Entrepreneur Interview Tools and Services

Favorite Project Management Software


Basecampy Logo

“If we're developing a new digital product, working on an email sequence for a certain audience, on a blog, or segmenting that audience, we do it in ConvertKit, but we operate our plans in Basecamp. Same thing for a redesign for a website in my portfolio, we can work with everyone in one place.”

“I'm the type of person who forgets to bring the notebook with the list or the agenda for the meeting or questions that are on paper with me to the meeting. So having a digital place for that is crucial for me.”

Favorite Client Portal Software

Service Provider Pro (SSP)

Sevice Provider Pro Logo

“This is kind of the equivalent of Basecamp for us. It also includes order forms and a checkout process where we can accept Paypal and credit cards for the agency.”

“If we work with a client, whenever they order one of our services, each team member already has their assignments the moment that they pay, and that just streamlines everything, helps me automate the services I offer. It almost converts for me the services offered into products that I'm selling. It creates a machine.”

Favorite Keyword Research Tool


Ahrefs Logo

“We use it for keyword research, link profile research on potential acquisitions, as well as overviewing the SERPs for any blog or content site that we're looking at or that we own.”

Favorite Finance Tool

Personal Capital

Personal Capital Logo

“Since I've graduated from the technician in my business to a manager and then to the entrepreneur that owns and markets the business and helps grow it, is where I put my CFO hat on and look at our cash balances, our credit, and then the asset growth over time and see how the business is performing big picture.”

Where to Find Him

You can reach Forrest Webber through his personal site or his agency site, or follow Forrest through his Twitter.

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