Jeff Proctor runs the site Dollar Sprout, which helps people manage their money better. He has some interesting stories about what he did before being Successfully Unemployed.  He also shares his finance expertise and explains the site’s success.

What Jeff Proctor Does To Make Money

Jeff runs, which helps people manage their money. Jeff’s background is working with a wealth management firm that helped people invest and save their money.

He is doing similar work now, just in a website form. He writes blog content for the website, and the way the site generates income is through affiliate marketing.

One example that Jeff uses is an article they have about saving tips. They will provide the tips and then recommend specific banks that offer a good interest rate.

When and if the reader clicks the link to sign up, then Dollar Sprout makes a commission off of that conversion. Currently, the site has about 400 articles, but not every article has affiliate links on them.

Jeff says that from building up the site and increasing access to financial information, they have steadily built an income stream.

As it is today, Dollar Sprout has five full-time employees, including Jeff and co-founder Ben Huber, and a half dozen contractors. 

What Jeff Did Before Dollar Sprout

Jeff graduated from Virginia Tech in 2013 with a degree in Biochemistry. It took him five years, and he was not happy with his GPA or the fact that he couldn’t get a job with his degree.

Even though he stuck the degree out, he was always interested in finance. Approaching graduation, he applied to investment banks, and wealth management firms. He applied everywhere he could think of that would accept him.

Unfortunately, out of countless applications, no one hired him anywhere he applied. Eventually, he found a job with a wealth management firm in Blacksburg, Virginia, where he went to school.

The position was as an intern position for $8 an hour and offered no benefits. Jeff answered phones, filled out paperwork, and checked the mail. He stuck with that position for two and a half years and went from $8-$12 an hour at the one year mark.

By a year and a half, they offered him benefits and $16 per hour. By the time he left, he was offered a raise to $40,000 a year after requesting a raise to $60,000. 

Jeff thinks that it’s true what Dustin has said previously. Employers will pay you just enough to keep you there but not enough to dip into their profit margins.

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During his time in that position, Jeff worked and received his Series 7 license. Even though he took on more responsibilities, the pay was still too low. It was a great time for him to try to go out on his own.

In August of 2015, at 25 years old, Jeff finally left. Jeff says that at the time, he had no idea what he was getting into but did it anyway. 

Dustin mentions that Jeff had saved up a year’s worth of expenses during this and that most people can’t even save half of a month’s savings. Dustin thinks that it is quite impressive of Jeff to do that. 

Living Off Of Savings

At the time, Jeff was still living a college lifestyle, so his year’s expenses were not as high as what a family’s expenses would be. He was able to save about $21,000 of his salary from his current job.

Almost a year before he left his position, he had it in his mind that he wanted to leave and do his own thing. He was still applying for other jobs, but he was planning his exit from his position with what he thought was about a year’s worth of expenses.

Jeff says it was funny when he was planning his departure, he assumed he would be spending the bare minimum on things and realized that is not how life works.

He went through his savings in about nine months, but he wasn’t too disappointed because he made it pretty far.  Jeff says that even if he had made it the whole year, it was still going to be gone.

The business at the time was not making enough money to support either himself or Ben so he ended up having to go back and get a regular job for an income again. 

Jeff explains that in the world of finance, there are a lot of rules regarding conflict of interest. He didn’t want to give up on Dollar Sprout but was hesitant to work for a financial business while also working the finance blog on the side.

Ben, Dollar Sprout’s co-founder, was a registered nurse at a local hospital and got Jeff a job as an aide. The pay wasn’t much but it was something and Jeff needed the money. Jeff took a position in the in-patient psychiatric unit. 

Jeff reflects on his journey of starting out managing money for millionaires, attempting his entrepreneurial hand for nine months to then working at the hospital. He served breakfast trays, was often on suicide watch for depressed patients, and even bathed some of the patients.

Working On The Site While Still Employed

The transformation in a short amount of time for Jeff was significant. While he was employed at the hospital, he worked on Dollar Sprout before and after work.

Jeff says the amount of work he was doing at the hospital often left hours to be filled. He would end up writing articles in the downtime he had at work. 

The first time Jeff left his job, he was not making any money from Dollar Sprout. He went all-in from day one. The second time he left a job, Dollar Sprout was making enough money to pay Jeff and Ben full-time salaries.

However, they were hesitant to quit altogether because of what happened the first time. It would have been too stressful, Jeff recalls.  

In an attempt to cut costs the first time, Jeff went without health insurance. Unfortunately, that was a time where Jeff was sick often. He was dealing with a lot of stress at the time and it kept compounding.

Being unable to go to the doctor, increased the stress in Jeff’s life which contributed to more illness. Jeff does not recommend going without health insurance. 

Jeff began cutting his hours at the hospital bit by bit and was eventually done around his 10-month mark of employment. 

The Difference Of Sites

Jeff says that he and Ben had thought about creating a course at one time. They spent time working on one but never finished it. They realized they did not like the work that it took to complete.

Jeff and Ben are more introverted and were not comfortable with the idea of their faces being out there as part of their brand. Jeff likes the idea of creating a good piece of content and finding a way to market it and get their audience to that content.

With 400 articles on the website now, each article becomes more of a mini-project. Jeff and Ben are more wired that way than for course creation. Even though course creation and email marketing are effective for most people, it is not the way that Jeff and Ben wanted to run their site. 

Domain Importance

Jeff and Ben got the domain name from a domain broker for $1600. Starting out, the site was They initially wanted to be an investment research company and offer a subscription service to their audience.

Jeff believes that it was part of the reason their first year wasn’t successful. The product creation and marketing were too much for them to handle. ((Not only that, they were competing with The Morning Stars and Kiplingers of the world.)) 

Jeff believes they were in over their heads and felt that blogging was easier to get started and a better fit for their personalities. As they shifted their focus to a blog, they realized their domain name made little sense for their new purpose.

New Domain, New Purpose

So, they found Dollar Sprout. Looking back, Jeff believes it was a great $1600 investment as it is easy to remember and people associate it more with money. 

Jeff thinks that the hard part about finding a domain name is that a lot of the good ones are already taken or are too long for anyone to remember.

He thinks they got a great deal on their domain because there are some out there that are priced at tens of thousands of dollars. 

If you are looking to start on a smaller budget, Jeff thinks just finding something and getting your content up online is important. Spending all of your time to find the perfect domain name takes from building your skills and getting your content out for your audience.

Jeff says to find something fairly reasonably priced and get started. If you get a couple of years down the road and you are realizing this is what you want to do, then buying a domain name at that time is a good idea.

Jeff says it wouldn’t be impossible to move the content over. 

Dustin thinks building your own domain can be successful too. When he was looking to start his Successfully Unemployed blog, he found that someone had already purchased the .com so he had to go with the .co.

The guy who purchased .com was not using the domain so Dustin called him to see if he would sell. He said no even after being offered thousands for it because he said he might use it someday.

Dustin moved on and used .co instead. Dustin thinks that if you can create a shorter domain, that will help people find you better and help out Google as well. 

Platform And Site Options

Between Jeff and Ben, Ben is the techy one. Jeff says that they have always used WordPress and love it. WordPress would be ideal for blogging and using something like Squarespace would be ideal for a restaurant or similar business.

Jeff thinks Squarespace is better for that business type because it is a place for posting your information about the business and making it look good. It is not necessarily aimed at content distribution but just an online presence for the business. 

Jeff says that their first hosting site was GoDaddy and it worked for them in the beginning. He says that the beginner hosting sites are all fairly similar and easy to use so pick the one you are comfortable with. 

Dustin thinks it is great that you can start your online presence fairly cheap. He used and Siteground and both are fairly inexpensive to get started.

Content Importance

Even though they are continuing to improve their content, Jeff thinks only a handful of the articles they have written are good content they are proud of.

He also thinks it is worth mentioning that they are working on the older posts to bring them to the quality level of the ones they are proud of. 

Dollar Sprout’s number one goal is to help a reader solve a problem or learn something about finance so they aren’t focused much on sharing their own personal stories.

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