DollarSprout’s Turning 5 Years Old. Here’s What I’ve Learned So Far.

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DollarSprout turns 5 years old next month. Sometimes I can’t believe we’ve made it this far.

They say that over half of all new businesses don’t live long enough to see their 5th birthday. Most fail long before then.

It hit me this morning that I’ve never shared the story on how DollarSprout got started on this site. I’ve mentioned it in interviews on other blogs and podcasts, but never here with our own readers.

I guess I’ve always thought to myself, “Our readers don’t care about that. Just keep publishing the content you already know they like.

A big part of entrepreneurship, though, is the struggle. The setbacks. The grind.

And that’s what I want to talk about today.

To celebrate DollarSprout’s 5th birthday, I’m going to take a quick pause from our regularly scheduled programming and talk about how this website — and business — came to be. I also want to share some of the personal struggles I’ve faced along the way in hopes that maybe hearing my story can help others.

For anyone starting a business or thinking about diving in, I hope you can find something in here that helps.

Background: What is DollarSprout?

In the beginning, Ben and I tried to create a paid membership site for stock market tips and analysis. It ended up being a total flop.

Here’s what it looked like during my first week of being self-employed:

One of the early iterations of what would eventually become DollarSprout
“VTX Capital” was the name of our first site before we rebranded to DollarSprout. Photo taken in 2015.

As it exists today, DollarSprout is a personal finance site that helps readers maximize their earning potential, whether that’s through finding a side hustle, moving up in their career, building passive income streams, or anything else.

DollarSprout makes money through advertising. We routinely promote apps, products, and services that help our readers get a leg up on their finances.

DollarSprout mockup
Quick Stats on the Business

Date Started: August 1, 2015. I was 25.
Total Readers: 12 million +

Annual Revenue: Low 7 figures
Team Size: 5 full time + ~10 contractors

We get to create content every day to help people with their money, and everyone on the team has the opportunity to earn a decent living. You can’t ask for much more than that.

The Reality Behind Building a Startup

It’s easy to look at the end result and think, “Wow, sure must be nice.

But the “success” is only one side of the story. This is what the other side has looked like for me:

  • I had a 2.53 GPA in college. And it took me 5 years.
  • I have ADHD. It’s a blessing and a curse, but mostly a curse.
  • I’ve struggled with depression and anxiety for most of my life. 
  • My first “real” job after school started at $8/hr.
  • I stayed there for two-and-a-half years and I hated every minute of it.
  • I lost my entire life savings on our first attempt at DollarSprout.
  • I worked in a psychiatric ward for almost a year after that to make ends meet.
  • In 2017, I left that job to try full-time entrepreneurship again.
  • Even when business is good, the mental health stuff stays with me.

Everyone deals with their own unique set of circumstances and adversity in life, and these were some of mine. 

A rough timeline on how we started DollarSprout

5 Lessons I’ve Learned Since Starting DollarSprout

I know a lot of people out there that are frustrated with where they are in their career or their life. Here’s what I want them to know.

Jeff next to Wall St. bull

1. Having a miserable job can be the best thing that ever happens to you.

As a kid, and even in college, I had no desire to become an entrepreneur. I thought I wanted to either be a doctor or an engineer. Both are respectable and well-paying careers, so I thought that’s what I wanted. Starting a business was never something I thought about doing.

That all changed shortly after I got my first job after college.

I got an office job at a financial planning firm, and that experience is what set me on the path towards entrepreneurship. Since it was my first job, I had no way of knowing if it was just this job that was terrible, or if all jobs were this bad. 

Looking back, I now know my experience wasn’t all that unique. A lot of people hate their job. I think I just hated mine more than most.

I think one of the best things to ever happen to me was having that awful experience right out of school. If that job didn’t make me so jaded to the corporate world, DollarSprout would have never happened.

2. Don’t be afraid of the worst-case scenario.

Before I left my full-time job in 2015 to start the business, I did my best to weigh the pros and cons. There was a whole range of possible outcomes:

  • Outcome 1: Business booms right away, and I make more money than I know what to do with.
  • Outcome 2: It takes 3-6 months to start getting traction.
  • Outcome 3: It takes longer than 6-12 months to make any money, and I have to go back and get a job. I lose everything.

No one likes to think about Outcome 3. It’s a Doomsday Scenario. 

Outcome 3 is exactly what happened.

I had saved up about a year’s worth of expenses to give this thing a fair shot, and I ran out of money after only 9 months. At the time, our website was bringing in virtually zero revenue. By all accounts, it was a failure.

For some reason that I will still never quite understand — maybe it was pure denial — Ben and I kept grinding on the business even after I went back to working full time (he was also working full time). We were living through the worst-case scenario that every entrepreneur has nightmares about, and it still ended up being okay. 

About 10 months later, the site was making enough money that I could give it another try and leave my job. I was scared as can be, but I did it. Shortly thereafter, Ben left his job too. Neither of us have gone back since.

The literal worst case scenario happened, and it wasn’t as bad as we thought.

3. It’s hard to beat the person who never gives up.

This is the living room where Ben and I spent the first four years building DollarSprout
This is the living room where Ben and I spent the first four years building DollarSprout

Plenty of people out there are more talented writers, better designers, better managers, better salespeople, etc., than me and Ben. 

The hardest thing for people to replicate, though, is the determination to just keep grinding. Things take time to come together — usually much longer than you think. 

After burning through my life savings on our first attempt, I don’t think anyone could have blamed us for moving on. That would have been the rational thing to do, especially considering our total lack of progress. 

I’m not the most productive guy in the world (far from it, actually), and I’m honestly not the hardest worker either. But I can stick with something longer than most people, and that has made all the difference. 

Be the person that doesn’t give up.

4. Your 2.53 GPA, lack of business experience, mental health struggles, etc. don’t matter as much as you think. You only have to get it right once.

To me, that is the coolest thing ever.

Mark Cuban once wrote, “It doesn’t matter how many times you strike out. To be a success, you only have to be right once. One single time and you are set for life.”

As an entrepreneur, if you can build something people value, you’ll make it. I am a mess in so many ways, and I still found a way to escape the 9-to-5 world that was killing my soul one day at a time. Like I said, it’s hard to beat the guy that never gives up. 

Chances are you won’t get it right the first time (we sure didn’t), but the exciting thing about entrepreneurship is you only have to be right one time. That wipes away all the past failures. Once Ben and I finally found something that worked for us, we were set. 

5. Be nice to people.

The world needs more of it, especially now.

I think a lot of entrepreneurs get this idea in their head that they need to be a cut-throat competitor with ice flowing through their veins in order to be successful. In reality, the more you help people — even your competitors — the more opportunities will open up for you.

There’s plenty of room for everyone at the table. Be a good person to sit with.

Don’t Underestimate What Can Happen in 5 Years

dollarsprout management team

If you would have told me five years ago that I would be running a business with my best friend and earning a better income than I could have ever made at a normal job, I don’t know if I would have believed you.

At the start of any new endeavor, everything feels so insurmountable. There is so much to learn, so much to do, and so much time you have to put in.

But if you start now and keep at it, you may just look up in 5 years and see that you are living the life you never thought was possible. 

Take risks. Push hard. Make it happen. And most importantly, never give up!

 
Author
Jeff Proctor

Hi! I'm Jeff. A personal finance nerd and entrepreneur at heart, I'm here to bring you all the latest cool ways to make and save extra money. I've been quoted in several online publications, including Entrepreneur, NBC News, GoBankingRates, Student Loan Hero, Business.com, Credit Karma, The Simple Dollar, US News & World Report, Lifehacker, MSN Money, Moneyish, Zumper, IdeaMensch, Discover Bank, PrimeRates, Credit.com, Yahoo! Finance, Club Thrifty, Guru Focus, Rent Track, Fit Small Business, Coupon Chief, and more.

29 comments
Shaun Myers
Shaun Myers

Great work guys! I’ve enjoyed following and watching you grow the business since VTX!

Thanks so much for the support, Shaun!! Hope you are doing well.

Sam @ Financial Samurai
Sam @ Financial Samurai

Very inspiring guys! I wasn’t really focused on entrepreneurship until 2018, when I realized I was leaving so much on the table.

It’s just me doing all the writing, business dev, marketing etc.

Would you suggest I try and scale up like you guys and hire people? Or would you guys just keep things a one-man band? It feels good to own 100% of the equity and keep things simple. But I would also like to compete more effectively.

It also doesn’t seem like Google really cares whether the writers have firsthand experience or have finance backgrounds. So long as the content is well-written, that’s all that matters.

I’d love to get your perspective on the upsides and downsides of pursing entrepreneurship versus just keeping things simple and writing.

Thanks!

Sam

Thanks, Sam! Ah, the big question: stay small or try to scale? I think if you would have asked me this question a year ago, I would lean way more on the “scale like crazy” side of things, but I think I’m becoming more moderate as time goes on. Now that we have scaled DollarSprout to more than just a two-man operation, there are definitely times when I miss the simpler days.

The good news for you is I think you can still scale quite well while keeping 100% of the equity, and you can start small.

The biggest thing I would recommend is actually the opposite of what you will hear most people say: I think you should start by outsourcing the things that you are most competent in. I’ve found that when I try to outsource the stuff I’m not as skilled at, I struggle with giving appropriate guidance. Then the outsourcing basically becomes a waste of money. You want to amplify your strengths, build new strengths, then amplify those, etc.

And yes, the most important thing, by far, is how well-made your content is. Is it digestible? Easy to read? Helpful? I used to hate it when people would say “Google just wants to show the best content, so make your content better” but the longer we do this, the more I realize that that is really what it all boils down to.

Mike
Mike

Thanks for sharing this Jeff! If more people did this I genuinely think the world would be a much better place (sorry for the crappy phrase but here’s why…)

People would have more realistic expectations about business, more people would stick it out, more jobs would exist and more people would be fulfilled with what they are doing.

I think most people know deep down when they are doing something that doesn’t fulfil them and it creates a lot of internal battles.

Love your guys journey, keep doing what you’re doing! I can’t wait to see where you are in 5 years 😉

Thanks for the support, Mike! Things definitely aren’t always smooth sailing (even when it might look that way on the outside), but I wouldn’t trade our situation for the world. People are capable of so much more than they give themselves credit for!

Janeen Scuderi
Janeen Scuderi

Wow!! What an incredibly honest and amazingly admirable person you are. I’m starting an online jewelry business and your words of encouragement are priceless! Thank you so much and good luck as your success grows bigger and bigger! You deserve it!

Thank you for reading, Janeen. If we can do it, I think a lot more people can do it too. You got this 🙂

Amanda
Amanda

Love this! Thank you for your honesty, and I’m SOOOO excited for you both:). Keep rockin’!

Thank you, Amanda! You keep rockin’ too!

Kari Sayers @ MompreneurMoney
Kari Sayers @ MompreneurMoney

Boy oh boy can I appreciate this post! I always like reading about the business struggles and failures. I failed at so many different businesses before I really dug in and focused on my current one. It’s in the mistakes and failures that we find opportunities for growth. Thanks for sharing your back story. Much appreciated!

Thanks, Kari! I’ve come to learn that failure is unavoidable, so you may as well get it out of the way and carry onward 🙂

Tara
Tara

Thank you for this inspiring, helpful and encouraging article and congratulations on your success.

Thank you, Tara!

Janel Carey
Janel Carey

Thank you for sharing your story and congratulations on your five year anniversary! It’s refreshing and encouraging to see what happened behind the scenes and led to your eventual success.

Thanks, Janel!

Al
Al

Loved reading your timeline like this, I guess a lot of people who start something like this (I’m including myself here) keep that short goal in mind at first…it’s hard to keep looking ahead through all of the difficulties. Thanks for sharing this! All the best in the years to come!

Charlene T. Bestman
Charlene T. Bestman

These are great tips. The one thing that I love about your storyline is the “never give up mindset”. Thanks for all of your effort over the years.

Thank you, Charlene! Don’t ever give up.

Dean Carolle
Dean Carolle

This story should’ve been here long ago. Haha. This is absolutely amazing, Jeff. Your story is what led me to start my own blog and when things get tough, I always turn to articles like this to keep focused on the end goal. Thank you, Jeff.

Yinka
Yinka

Congratulations on your 5th year anniversary. May you celebrate many many more. Thanks for sharing your story. You both are a great inspiration.

Vicky
Vicky

This is beautiful! I love it. Great advice for everyone, but especially someone with ADHD!

Caroline @ Costa Rica FIRE
Caroline @ Costa Rica FIRE

Congrats on 5 years! Our blog is about 2.5 years old now, and while we’re seeing growth, it is a grind as you say to build up that traffic. Agree that you need to balance with other work while building a blogging business. In our case, the blog is a passion project, though we are trying to monetize it, and we have a consulting business, real estate, and a paper portfolio alongside.

Priscilla Wilkinson
Priscilla Wilkinson

I really appreciate the fact that you shared your story and that you were so transparent. That is how I strive to live my life by sharing the good, the bad and the ugly in the hopes that it will help someone else.

Your transparency encouraged this 61 year old lady to continue to work toward her dreams…and she dreams big!

Dorothy Marie Joyner
Dorothy Marie Joyner

I enjoy reading you and Ben’s story a becoming entrepreneur and owning an online business. The story that you (Jeff) and Ben share is very uplifting to my heart and soul because the both of you never gave up.

I have also learned the in this life we all will go through many up and down, but we must learn to stay strong and never give up.

Reading your story reinforces my thoughts that we never know in which directions that God may direct our lives. However, if we stay strong when we are going through very hard times, then, we can make it through anything that our journey in life leaves us.

May God bless and keep you (Jeff) and Ben in your business (DollarSprout’s) and in your personal life.

Sincerely,

Dorothy Joyner-Hayes

Thank you so much, Dorothy! I appreciate your support.

Roger Friedman
Roger Friedman

Congratulations on hitting the big milestone, Jeff and Ben. Love what you guys are doing. Keep up the great work!

Thanks Roger!:)

Lisa
Lisa

This article is exactly what I needed to read today. Thank you for your transparency and honesty. May you continue to grow and share your knowledge and experiences with others who are ready to “sprout” with their own ideas and vision.

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