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 DollarSprout.com, 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 VTXCaptial.com. 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 CheapName.com 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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The way they do that is to balance their content between comprehensive and digestible. A lot of their posts are several thousand words which if you’re reading it, it will take about 10 minutes to go through.
Creating that type of content requires a lot of research upfront and figuring out how you want to deliver it is important.
Outlines Are Essential
Jeff doesn’t think you can just begin typing and get all of the information out without having a plan first. He says it is important to create an outline, decide topics to cover, including affiliates if needed, and where to put them in the article.
With all of that information, in the beginning, Jeff says you have a roadmap to working with and it makes it easier to create the content from there.
Dollar Sprout’s Writing Style
For the most part, Jeff says they try to limit the amount of personal involvement in the posts. Their approach is more of an educational one where they are explaining the concepts.
They have started using more stories from other people that relevant to the article. Jeff said as he reads other blogger’s content that includes anecdotes from others, he thought adding that into theirs would make it that much better.
He liked the idea and thought the writers made the content better by using the stories of others.
Pro Tip: Pick up on tricks from other blogs that make the content better and use them in your posts
Amount vs. Quality of Articles
While Jeff and Ben looked back on the last year’s worth of content, they realized some of the quality in those articles suffered. Even with 400 articles, which is small in comparison to some, they felt as though they were publishing too fast.
For them, their three to four articles a week was too much and they have since slowed that down. Now they may be doing one to three per week.
For Dollar Sprout, it is important they take their time and create comprehensive, quality posts on their topics rather than just get out as many as they can.
Initially, Jeff feels they got caught up in the success of the posts and wanted to amplify that. However, it was too much and too fast so they focused more on quality content.
Who Does the Writing For Dollar Sprout
At this point, Jeff and Ben are no longer writing content. Their full-time employees are editors and their writers are freelance. They have met a lot of writers through the FinCon community, a community of people who work in the financial and media industry.
Jeff acknowledges that he is not a fast or a great writer. They hire freelance writers because they are quick and really good at what they do. Part of Jeff and Ben’s job is to pair their writers up with the content within their strengths and making sure they can monetize with traffic to the site.
Including Jeff and Ben, they have five full-time, W-2 employees. The editors work with the freelance writers but also are working on going through old content to bring it up to the current standards.
Even though there are only a couple hundred articles, if you do it the right way, fixing the old ones and bringing them to current quality is a full-time job.
Finding and Paying Writers
Jeff recalls hiring his first freelance writer off of UpWork. He says they didn’t pay on a per word basis but rather $25 per article. He says, unfortunately, you get what you pay for.
The way they looked at freelance at the time was more that if someone sends in something, they would be able to edit it on their own. Generally, you are taking a gamble working with freelancers outside of the United States.
The rates are cheaper but you run the risk of English not being their first language or other setbacks. Jeff says it was tempting to get an article for $25 and they had to try it, but now they know.
Starting by hiring from UpWork but then moving into hiring someone from the FinCon community is what Jeff and Ben did.
Finding Better Writers
Some of the first freelancers they used from the FinCon community charged around $100-$150 per 1500-2000 word articles, which comes out to about $.10/word. These freelancers were building their resumes and portfolios so their prices reflected that.
From there, they moved on to freelance writers that have maybe worked for some bigger sites and have a more developed portfolio. Those rates reflect about $.25-$.30 a word.
Now, Jeff and Ben are wanting to move up to the writers that have fully developed portfolios and have worked for big names such as Forbes or Bank Rate.
These more skilled writers are charging about $.40-$.50 per word so it can get pretty expensive to hire but it is worth it for the quality of writing they receive. Jeff says that there is no real rush to get to the top-tier writers. As your revenue increases, you are able to hire more advanced writers.
When To Implement Ads And Affiliates
Dollar Sprout used to have ads and affiliates on the site. Based on their traffic, they were able to generate some income. They started with affiliates much sooner than ads.
For affiliates, you don’t need the higher traffic requirements. If you have a good spot for someone in the article, then you can reach out to that advertiser and get added to their program. Jeff says it is usually fairly easy but it is possible to be rejected from time to time.
Finding Affiliates
Jeff and Ben began their search for affiliates by joining affiliate networks such as cj.com. You go to the site and set up a free profile. In the profile, you add your site traffic information and other key points about your site.
Once you do that, you are able to see the advertisers within the network. Jeff says there is also a filter option to find the best fit for your site and for specific articles.
Although there are quite a few of these types of networks, Jeff said they contain a lot of the same advertisers. However, if you do your research you might find differences in their offerings.
When you are beginning to brainstorm advertisers, Jeff says you can use your personal choices for things to promote. For example, if you use Personal Capital, you can say your use them in the article and list the affiliate link.
Make Sure Companies Align With Your Purpose
From there you can start to look into what other bloggers are using in your niche, and also the good and bad companies to work with.
Dustin and Jeff both agree that if there is a company with an affiliate program and you don’t particularly like or believe in it, you don’t have to use them on your site.
Dustin doesn’t even think you should use companies like that since you are sending your audience there. Negative experiences from your audience could reflect poorly on you since you are the one that sent them to a particular company.
Dustin uses cj.com and impact.com where his information is stored so he doesn’t have to continuously add his information, he can simply click “apply”.
Once you apply then you are either automatically accepted or rejected because they have access to what you have done before.
The Best Companies to Affiliate With
Jeff doesn’t think you should necessarily look at the companies that are the best to promote but the ones that best match the content you are writing. It is important to choose the ones that resonate the most with your audience.
For example, Jeff and Ben wrote blog content on investing initially but would experiment with writing articles on different topics. They found that their audience related more to posts like The 10 Best Ways to Make Money on the Weekends, or more comparison posts like that.
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Jeff put more of the focus on adding affiliates to those types of articles because that is what the audience wanted. He said he didn’t want to continue promoting investment companies if his audience was more interested in learning about making extra cash on the weekends.
Jeff also says it is more worth his time to go after a smaller commission but higher volume type of affiliate if it better fits his audience’s needs.
When Dollar Sprout Quit Using Ads
At the time they stopped using the ads, they were giving up about $20,000 a month in revenue. Jeff said that was painful but they were paying attention to the leaders in their space.
Not many have display ads on their sites because they are more focused on affiliates. Even though the amount of money they were giving up was big, they felt it would create a better experience on their site for their audience.
Jeff says not paying attention to the money that wasn’t coming in that they lost was the way to go.
The Pay-off Was Worth It
Although it is hard to pinpoint the actual payoff, the user experience improved which improved their brand quality. Additionally, the speed of the site increased without having to load the ads.
Jeff says that with Google having to choose between a site that takes one second to load versus a site that takes six seconds, it will always choose the faster site.
Removing the ads also helped the site rank better with Google and funnel more people to certain offers. Since the Dollar Sprout content strategy focuses more on teaching than personal stories, it made sense for Jeff and Ben to do away with the ads and use their affiliates to better cater to their audience.
Continuing to Scale
Starting out, the articles were shared through Twitter and Facebook. However, Jeff wasn’t seeing the traffic increase much. They got in on the tail-end of the Pinterest boom and were able to see some success from that.
Jeff and Ben didn’t want to have all of their focus on one platform. They started paying more attention to Google and SEO. SEO is a way to create your content in a way that makes it easy for Google and other search engines to understand what your content is about. SEO also helps Google assess the content and rank it accordingly.
Jeff mentions that there are certain strategies you can employ to increase your rank on Google but it isn’t a quick return on your time.
Now they use Pinterest, some Google ads, and some paid ads on Facebook for their articles. In addition to those, they also have an email list of readers.
Adding New Platforms
Dollar Sprout also has a YouTube channel. They use their email list to get people to the channel just as they do with Pinterest and Google. Eventually, Jeff says that you build up and use the platforms to build the others.
Jeff says that it is worth mentioning that these have been started over time. He says you don’t want to start on day one with starting all of these, it is too much.
Dustin notes that within four to five years, Jeff and Ben were able to build something big enough that allowed them to not work a JOB. Not only that, they are helping so many people along the way.
Dustin says that is one of his favorite things about what he does is helping people. He has his coaching business for real estate investing and when his students succeed with investing or quitting their jobs, he feels ecstatic about it.
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What Jeff Proctor Would Have on His Tombstone
At this point in his life, Jeff thinks the tombstone would say that he built a really big business so he could do good for the world. Eventually, he wants it to say that he built a really big business that did a lot of good for the world.
Not choosing to be a personal brand sometimes inhibits Jeff and Ben to be involved in their niche community the way they would like. Jeff believes they are making an impact but it is harder to see build the wall of the brand.
One Piece of Advice from Jeff
If you want to eventually leave your job, Jeff says to wait until you make sufficient income from your website. He points out how stressful that time in his life was without having the income from the site.
Jeff said it negatively impacted many areas of his life for a year. He would never want to go through it again and would like to see that no one else does either.
It is important to have some sort of security before you leave your job. Jeff thinks if he could change his naivety about that at the time, he would have.
Advice to His Younger Self
Jeff would tell himself to study what he wants to study in college if he goes to school. He had always thought about being someone who made a lot of money. Jeff wanted to be a doctor or someone revered as smart instead of the entrepreneurial route.
He says he made the mistake of going into something that he ended up hating. Jeff would even skip classes more and he didn’t do too great in class. Jeff believes that if he had just been more open-minded or found something he liked to do, he would have been better off.
Dustin likes the idea of not everyone needing to go to college. Aside from doctors and lawyers, Dustin thinks that the debt students get into is just too much and most times isn’t worth it.
Jeff said he was fortunate enough to split the cost of his college debt with his parents but still believes that half was a huge burden to him.
Dustin recently came across his wood embossed diploma from his college and has plans to blow it up. He will never have to use his degree again and loves it.
Dustin believes there are very few reasons to go to college. There are so many ways to make money and provide for your family while being successfully unemployed.
Jeff sees his diploma on the wall as a constant reminder of the degree he slaved away for but will never use and got into a lot of debt over.
How Jeff Views Humility
People have said that Jeff sometimes overdoes it. One of the weaknesses Jeff describes of himself is that he doesn’t acknowledge how far he has come and what he has accomplished.
At times he finds himself discounting the work they have done and focuses more on doing better than that. Jeff says that humility is a good thing but it can definitely be overdone.
Dustin loves the idea of humility. To him, it is not thinking less of yourself like deprecation, but thinking of yourself less. To focus on another person and how you can help them or benefit them.
The more people Dustin meets and learns about, the more he learns and is able to help. He wants people to think he is a nice guy.
Jeff wants to get better at it also. He thinks that when you get into the business mentality, you figure out how it works and you try to get better at it instead of trying to connect with people to truly help them.
Jeff says sometimes you have to focus on connecting with people or maximizing profits and they are not the same thing. This is something that Jeff wants to work on and be more aware of in the future, learning to balance the two.
One Tool Jeff Uses
Jeff uses his notebook and writing tool. He says that he has tried online tools but he needs the lists and checkboxes in front of him.
Dustin thinks there is something about using pen and paper that helps the information remain in your brain and Jeff agrees.
The Non-Fiction Book Jeff Recommends
One book that Jeff says a lot of people think is cheesy but he loves is The 10x Rule: The Only Difference Between Success and Failure by Grant Cardon. 
. Jeff likes the way that Cardon views life and the way he looks at everything through a bigger lens.
Where to Find Jeff Proctor
Jeff is excited about the new site update. He said it was a huge project for them to do but are happy with the result. You can visit them at dollarsprout.com. You can email Jeff at jeff@dollarsprout.com or follow them on social media. Lastly, you can find them on their YouTube channel here.