How Robert Makes a Full-Time Income from Side Hustles and Investments


Silas & Grace

Hey everyone, today I’m interviewing Robert Farrington from The College Investor. He has some amazing tips on how to invest and pay off college loans with side hustles. Definitely check it out!

1. What first interested you in investments and finding profitable side hustles? Give us some background on how you got started. 

I have always been a “side hustler”. My first side hustle was selling candy bars in middle school. My mom would take me to Costco, and I would buy the big 30 pack of king size candy bars, then I would resell them individually at break and lunch at school.
With investing, I grew up watching my dad update Quicken on his computer and I was fascinated by it. I would sit, learn, and watch. When I was old enough to invest with my own money at 16, I did! It was fun to watch my money grow, and even when I lost money, there were lessons learned.

2. I know that since you had success with creating different income streams, you also wanted to help out other college students who were struggling with loans and finances. What brought about this desire?

When I started my blog,, I was sitting in class, and I wanted to share my thoughts on investing. I honestly just wanted it to be my random advice on different stocks, market trends, and economics.
However, several of my friends said “that’s cool – but I can’t invest right now because I’m dealing with these student loans.” After that, I started writing more about student loan debt, how to get out, manage your payments, and more.

3. What did your family and/or wife think when they learned of your passion for investments and side hustles? And how did they feel when you wanted to help others?

My wife and family have always been supportive of my side hustles. One of my favorite side hustles has always been going to garage and estate sales, buying things, and reselling them on eBay. My wife has accompanied me to plenty of estate sales and she typically enjoyed it.
When it came to starting my blog, they were very skeptical that a blog could make any money. And they were right for a while – it took about 2 years before I started making any real money on my website. However, today, it’s my full time job so I guess things worked out pretty well.

4. When did you first start your journey to getting out of student loan debt and investing? And what were some of your first steps?

I started investing when I was 16. I started with $100, and used Sharebuilder (now CapitalOne Investing), because they had this cool service where you could automatically invest for just $4 – which was super cheap back then. I just continued to invest throughout high school and college – even just small amounts that I could afford.
When I graduated from college, I had $40,495 in student loan debt. It took my about 3.5 years to pay that off – and I did it through extreme focus and side hustling. I would throw pretty much all my extra income at my student loan debt, and I would be earning more through side hustling that went towards it as well.
5. How did you find side hustles and investments that interested you?
For side hustles, I just focused on what was interesting to me. I liked to sell stuff, I liked antiques and computers – so I combined all these and sold stuff on eBay.
For investing, when I started, I really wanted to pick stocks. I thought that was the way to wealth. I didn’t do bad, but it didn’t make me a millionaire. Today, I’ve shifted to investing in a diversified, low cost, ETF based setup that is designed for the long term. No more trading for me.

6. How long was it until you started to see some of your first profits?

In investing, I started seeing gains right away. I just looked back on my tax returns, and in 2004 (when I would have been 19), I earned $3,625 in dividends, and took a capital loss of $610. Clearly I didn’t always win – but the dividends were great, and I consistently reinvested them.
For my business, it took about 2 years until I started seeing profits from the blog. I really didn’t know what I was doing, but once I figured it out, it started earning about $2,000 per month in year 3.  

7. What were some of your biggest challenges when you first started? 

 When I first started the blog, I had no idea what I was doing. I was simply sharing my random thoughts about investing, and writing really basic stuff. What was really a turning point for my hobby turned business was to network with other bloggers. It started with the Yakezie Network of bloggers, then it evolved to the FinCon Community. By connecting with other people doing similar things, I was able to learn and grow.
At the same time, I started writing more for my readers, versus my own random opinions. Once I overcame these two things, I started seeing a lot of growth.

8. What was one of your biggest mistakes when getting into investments, and how can others avoid it?

My biggest mistake was trading individual stocks. I thought I could pick stocks – but statistically, that’s not viable over the long term. I’ve probably lost $10,000+ in bad investments in single stocks over the years.
Today, I focus on maintaining my properly diversified, low cost index fund portfolio. It’s not sexy, but it works for the long run.

9. What is one of your favorite thing about having multiple income streams? 

The best thing about multiple income streams is not feeling fully dependent on one or the other. My eventual goal is to have several that I could easily live off of without any switching costs. 

11. How long did it take until you were able to live off your investments and turn your side hustles into full-time income?

 I can’t fully live off investments (yet), but I now do my side hustle full time. I started my blog 8 years ago, and just left my day job to pursue it full time this year. So, it took me some time.
12. What does your daily routine look like now that you work for yourself?
My daily routine is all about family. Family first. I get up in the morning with the kids and fix breakfast. Once my wife is up and going, she’ll usually take the kids for a few hours while I work. They come home for lunch, and we have family time for the rest of the day. Then I usually get a few hours of work in at night before bed.
13. What’s your best tip for where to start? What advice do you wish someone had given you when you were new to finding a side hustle and investing?
If you want to find a side hustle, network with others doing the same thing. You’ll find community, motivation, and you’ll learn faster.
For investing, keep it simple. Low cost index fund investing for the long term.
14. Did you have any mentors or heroes that inspired you when you first started?

I follow a lot of online mentors – Gary Vaynerchuck and Pat Flynn come to mind. I also read a lot of other bloggers and saw what they were doing in my space.

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Chasing Foxes was started in 2016 as a way for Grace and her husband, Silas, to start traveling. However, they started to realize that they had a passion for improving themselves, and wanted to help others level up their lives as well. So whether it's with cooking, travel, or staying healthy, they want to help you better your life bit by bit, as they do the same.

Leveling Up Your Money Money

Silas & Grace

Chasing Foxes was started in 2016 as a way for Grace and her husband, Silas, to start traveling. However, they started to realize that they had a passion for improving themselves, and wanted to help others level up their lives as well. So whether it's with cooking, travel, or staying healthy, they want to help you better your life bit by bit, as they do the same.

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