When It’s Time to Go from Solopreneur to Team Leader – with Robert Farrington

As a solopreneur content creator, it feels like there is a never-ending list of responsibilities to address. Have you ever found yourself wondering how you can get everything done on your to-do list?

As your brand grows, it is vital to remember that you don’t have to do it all. In fact, feeling like you can’t do it all might actually be a sign that it’ s time to expand from solopreneur to team leader with outsourcing.

The creator of TheCollegeInvestor.com and LoanBuddy.us stopped by to share how he took his blog from a hobby to an online business by growing a team. Learn more about when and how to make the transition from solopreneur to team leader with this insight from Robert Farrington. 

How and Why He Started His Blog

Years ago, Robert Farrington started his blog as a culmination of his hobbies and interests. The College Investor came into being because Robert loved discussing personal finance and money topics, plus he was passionate about investing.

As an added bonus, he was also interested in the technology piece of blogging. Overall, Robert saw blogging as a way to share these thoughts with the world.

Click here to see more examples of content creators with breakout blogs in the personal finance space.

How He Scaled It Over 10 Years

Though he started The College Investor as a hobby, Robert realized that he could make a little money on the side from his blog. After working on the blog for about a year and a half, he started to dialogue with others about how to monetize the site.

Initially, he started with Google AdSense. Robert says it was a simple enough starting point. He added a piece of code to include display ads and made a little money when people engaged with the ads. Soon after he began to experiment with display ads, Robert also began to test out affiliate marketing.

Now, affiliate marketing provides the bulk of the site’s revenue. Affiliate marketing is a way to bring in money for promoting products and services his readers will appreciate. From Robert’s perspective, affiliate marketing offers wins for everyone involved. He promotes great products on his site that will benefit his audience.

To learn more about affiliate marketing, check out advice from experts in the personal finance community here.

Robert credits the fact that his online business stayed content-focused as the main reason that he was able to continue to grow it. Once things really started to take off, he realized it was time to change hats from solopreneur to team leader.

When He Brought On His First Freelancer

As his site grew, Robert stayed focused on content development. One of the reasons Robert says his site saw such a spike in traffic is because readers could count on The College Investor to create the best content.

To consistently bring the best content to his audience, Robert says he needs to invest time, effort, and energy. To accommodate his small business growth, Robert realized it was time to start outsourcing. Bringing on a freelancer was an essential step in scaling his online business.

Solopreneur typing on laptop

While Robert realized he had no shortage of ideas as a solopreneur, what he did have was a shortage of time. In fact, he could list dozens of ideas that would make excellent content, but he knew that he couldn’t continue to churn out content at the pace his audience wanted without burning out.

It was time to grow a team. His first outside hire was a freelance writer who could help him get these ideas out into the world. To find his first freelancer, Robert used connections in the personal finance space.

How He Scaled from Solopreneur to Team Leader

As Robert made the jump from solopreneur to team leader, he continued outsourcing. Initially, he started with one freelancer and then grew his team to 10 freelancers. As he continued outsourcing, he prioritized content creation.

One thing Robert notes is that content creators can feel apprehensive about outsourcing. As a solopreneur, you’re used to doing it all. However, Robert says that outsourcing your writing is one of the easiest low-risk ways to get used to growing a team.

While the writers are creating content to help with small business growth, they aren’t actually immediately or directly impacting your business. Bearing this perspective in mind helped Robert stay open-minded during the trial and error process of growing a team.

To grow his team, Robert pulled from existing networks, such as the FinCon community, and word-of-mouth referrals. He also used sites like UpWork and the ProBlogger job boards. Moreover, Robert says he has started to explore companies like Design Pickle that pair you with freelancers and also help you manage the freelance workload.

Solopreneur outsourcing Freelance Graphic Designer work

The Systems and Processes He Uses to Keep on Task

There are a variety of different communication and calendar tools that team leaders can use to communicate with their freelancers. Robert says that Asana is his preferred system for keeping his team on task.

He likes the management aspect that allows him to put subtasks together within the calendar, allowing him to see all the moving pieces of a project. Additionally, Asana allows for organized communication within each subtask. He also notes that other team leaders prefer tools like Slack and Trello. Ultimately, you want to find the tool that works for you and how you lay out your business.

In addition to outsourcing writing, Robert also outsources some of his social media work. He has a social media manager who knows how to take Robert’s content and infuse it with emojis and other copy styles that will yield higher engagement.

Even with all of the outsourcing, Robert also says that nothing replaces authentic engagement when it comes to your online business. Often times, people equate small business growth with scheduling and automation. However, you can’t simply push content on your audience; you also have to engage.

Robert says this is more time-intensive, but the payoff is worth it. While a lot of the content for The College Investor is scheduled, Robert is heavily involved in conversations on Twitter and in his Facebook group. This engagement is what yields both actions from his audience and results for his online business.

Learn more about boosting engagement and hooking your audience’s attention here.

Business Plans for the Future

Now that ten years have passed, Robert says that he has big plans for his brand. Continuing to provide the best content possible for his audience remains at the forefront of his planning. He also realizes that he will always have to adapt. That means that he is going to continue trying out new things and exploring new ways to present content.

Robert hopes to continue to see his traffic grow. As a content creator, he says that it is really rewarding to watch your content be consumed. When traffic analytics reveal an uptick in readers, that is really rewarding. He knows that the way he presents and shares his content will likely continue to evolve. No matter what, though, he intends to keep content development a priority.

Click here to do a content audit to help you analyze your site and boost your traffic.

solopreneur viewing analytics on a laptop

How to Start Outsourcing as a Solopreneur

If Robert sounded really relatable when he talked about being heavy on ideas and light on time, it might be time to start outsourcing. But where do you begin?

According to Robert, make sure that you focus on creating the best content and use that to plan your outsourcing accordingly. When you create quality content, it is easy to be excited to share and promote your work. Other content creators will be equally enthusiastic about sharing your work. Plus, Google favors quality content.

Once you have committed to letting content drive your work, you are ready to work through these steps to start outsourcing.

Shift Your Mindset

It can be scary deciding to spend money and hand over a piece of your business. However, it is important to remember the role that content development has in small business growth. Hiring a writer is an opportunity to create good content that will propel your business forward.

To make the transition to outsourcing less overwhelming, Robert says it’s important to keep perspective. When you take on a freelance writer, they are not modifying any of your site. If the product that comes back to you doesn’t meet your expectations, there is no obligation to publish. In that situation, you can simply pull the piece.

You do have other options as well. You can provide feedback to the writer, requesting changes and updates. Robert also says this is time to look inside yourself. Perhaps the piece does not meet your expectations because you were not clear on what you wanted for the assignment.

Set Clear Expectations

When preparing a freelancer to work with you, the most critical task is to provide clear expectations. Communicate the priorities of your online business and clearly define what you are looking for. Robert cautions that if you are too general, you don’t actually know what kind of work you will get.

He suggests including a bulleted overview of the topics you want your writer to touch on, in addition to samples of content that represents what you’re looking for. More so, you want to consider the scope of the work that you are requesting. Does the content need expert interviews? If you are looking for a sourced piece of writing, you will likely need to adjust both the time frame of the assignment and the pricing.

Solopreneur explaining assignment to freelance writer

Communicate Pricing

Before you decide to explore outsourcing, it is important to be clear on your pricing. Solopreneurs may not have given this much thought; however, it is a necessary part of being a team leader.

Robert says that different businesses conduct their pricing in different ways. There is a lot of variety in terms of pricing by range or by word. Robert suggests using a pricing model that charges X dollars for Y range of words. His rationale is that a range allows for style without worrying about having to cut through fluff or filler.

Test and Build a Relationship

One thing to prepare for when you start outsourcing is to know that not everything will make the cut. Robert admits that giving negative feedback is hard. Still, the best way to deal with the situation is to be frank.

Additionally, if you are just starting to see small business growth, you want to make sure that you start outsourcing on a trial basis. Robert says that you will pay regular rates, but you should ask the writer to produce a trial piece. Then, if the partnership works well, you can move forward and assign more work. He likens it to dating, saying that you go on the first date before committing to future dates with that person.

Even established partnerships can benefit from open communication. Writers’ priorities can change. For instance, your writer might start out freelancing for you and then they start to build their own business. As a result, their bandwidth might change. That is why communicating clearly and openly is so beneficial, whether you are just transitioning from solopreneur to team leader or are a veteran team leader.

Final Thoughts on Switching from Solopreneur to Team Leader

You’ve built your brand from the ground up, and now you find yourself with more tasks to do than time. It might be time to scale up from solopreneur to team leader. While it can be overwhelming to commit to the transition, Robert’s work on The College Investor shows how worthwhile it can be. Begin outsourcing with clear expectations and open lines of communication, and get ready to see your brand grow.


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Andy Hill

Andy Hill is the award-winning podcaster and blogger behind Marriage, Kids and Money which is dedicated to helping young families build wealth and thrive. Andy's personal finance experience has been featured in major media outlets like CNBC, Business Insider, MarketWatch and NBC News. Trusted as a personal finance influencer by national financial brands, Andy’s message of family financial empowerment has resonated with listeners, readers and viewers across the US. When he's not "talking money", Andy enjoys wrestling with his two kids, singing karaoke with his wife and watching Marvel movies.



    • His story is definitely inspiring – and his willingness to give back to the community.

  • Thanks for sharing Robert and thanks for the article/video, Andy! I loved what you said about creating the best content. I think most marketers think the only reason to do that is so it stands out in Google. But it’s more than that. It’s like Robert said… it also makes it way easier to SHARE it because you actually believe it’s awesome and want people to have it. And people are more likely to link to it, share it, bookmark it, etc. I love this! Thanks also for the outsourcing tips.

    • So glad you liked it Chris! I definitely learned a lot too. Here’s to growing your site!