Starting The $5,000 / Month Challenge


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A Personal Challenge to Start a Recurring Revenue Business in 2015


Over the years I’ve “tried” to get a small business going, and I’ve had success on par with my effort, meaning I’ve always come up with an idea, thrown a bunch of time and effort at it, then felt gloomy when it didn’t make millions.


A Short History of Minor Success

I have some CG models for sale on TurboSquid, and have made several hundred dollars over the years; I have a site on which I sell an ebook about building a very niche tool for acoustic guitar and instrument building. I’ve sold maybe a couple thousand dollars worth of the ebooks and the gobar clamps over the past few years.

Nothing to write home about, but it’s easy income; I wrote the ebook once, and have done a few updates, but basically it was about 20 hours to write, and another 20 hours to illustrate, then maybe 20 hours of updates over the years. So, all-told under 60 hours of work for a couple thousand dollars? That’s not terrible, right?

The CG models were some that I whipped up while teaching myself Blender, an open-source modelling tool, similar to 3D Studio Max or Maya. I had fun making them, and learning to render them properly. They have sold okay, and most months my paypal account has a few bucks in it. A little fun money, but nothing to depend on, and definitely not to live off of!


The Trough of Sorrow

Just over a year ago, in November of 2013 I launched a site, that I felt was a significant improvement on the Hot Rod and Motorcycle classifieds that are out there. It was a labor of love, and I have around 1500 visitors a month, despite that the search hosting I was using stopped working, and there are very few new listings. I have several hundred people on the email list, and several hundred people have liked the page on facebook.

Paul Graham dubbed this the ‘Trough of Sorrow’ – the time after launch when there’s not much traction, and you lose momentum, and just kind of _dwell_ where you’re at. You lose interest, motivation, etc.

That’s kind of where is right now. I’m trying to decide whether to invest more time and energy in it, when it’s a marketplace site, which is pretty much the hardest type of site to build, as you have to overcome the chicken (i.e. consumer) before the egg (i.e. seller) problem.


Where Do I Go From Here?

Over the past six months or so, I’ve read a ton of stuff from Amy Hoy (30×500) who talks about how to NOT start with an idea, but rather target an audience, and find a pain point to solve. I also have greatly enjoyed reading the blog of Groove CEO Alex Turnbull.  The last straw was, over the Christmas break I stumbled across Nathan Barry’s Web App Challenge and thought “I need to get off my ass and do this”.

All that being said, I decided to challenge myself to by the end of 2015 have a side-business that makes $5,000 USD in revenue. I think that doing it here in public where anyone who cares to see can see what I’m doing, and how I’m doing would be good motivation to keep moving ahead. With inspiration from Nathan, Amy and Alex, I think I can reach my goal, and have fun doing it!


The Parameters of the Challenge

So, as with any contest or challenge, there need to be rules around it.

  • Start on January 1st, 2015, and show $5,000 in revenue in at least one 30 day period prior to January 1st, 2016.
  • Start a new business, from scratch in an area that I’m an expert, or have a substantial leg-up (in my case it will either be the programming world, or hot rods/motorcycles, or likely the area where they cross)
  • Start without a predetermined idea, but with a target customer
  • Be completely transparent about every step of the process, in the hopes that it encourages someone else to embark on their own challenge – this means financial disclosure, time investment, motivation (or lack of it), tools and services used, etc.


My intention is to focus not on a consumer product or service, but rather something that solves a problem for a business (businesses have money and are willing to spend it to save time/money, whereas consumers are notoriously tight with their money, even if it saves them time/money in the long run).


Frequenty Asked Questions

Taking a page from Nathan Barry… no one has asked these, but I would assume the answers might be of some interest to you.


Where will you get your idea?

Amy Hoy talks about her “Sales Safari” – scrounging existing websites that your target customer frequents to look for questions, requests, pain points, common issues or areas that are difficult or confusing to people. I’m going to follow this concept and dig for pain that business owners in my target market feel. I’m also going to reach out to the subscribers on my email list from and also my neglected hot rod/motorcycle blog


What technology will you use?

I’ll use the best tool for the job, within reason. I’m an expert Java programmer, and was previously a DBA, so I know SQL quite well. However, I also know Ruby, Python, Javascript, etc. and have dabbled with NoSQL DB’s. My intention is to get up and running ASAP once I have a direction and solution identified… I expect to use either Meteor, or Angular coupled with the Play Framework to build the site/app.


How much will it cost to build?

The solution will be completely bootstrapped, so likely a couple hundred to a couple thousand dollars. Most of this will likely be advertising, and hosting fees. The goal is to have the site profitable immediately, since I’m focusing on solving a pain-point, I expect to have at least two or three customers paying on day one, as part of the validation of the solution.


What if you fail?

I think I’ll succeed in finding a pain point that needs solving, but whether I reach my goal of $5k/month in revenue remains to be seen. You can decide for yourself if I have succeeded in building a successful business, or if it was a failure in 12 months.


The Starting Line

So that’s it! I’m off and running! What do you think I should build? Who do you think I should talk to? Leave it in the comments!



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  10 comments for “Starting The $5,000 / Month Challenge

  1. January 3, 2015 at 8:08 am

    That’s insane, because I’ve been thinking about doing the same thing. I figure if I can get a business bringing in $1,000 a month, I can figure out a way to get more per month from that business by making adjustments to my business model and/or product. I’ve never made $5,000 a month on salary, so I don’t even know what that sort of money feels like. That’s a big part of why I think $1,000 is a good goal in my case. The other largest portion of my decision is that I lack experience — I had a really small consulting hustle going where I employed others, but I never launched a product and tried to make money from it, so this’ll be my first time. Perhaps I should start even lower, at $500? Nah — it’s probably better to aim higher than my more reasonable expectations!

    Good luck! I’m curious of how this’ll turn out!

    • admin
      January 3, 2015 at 12:46 pm

      Hey Greg, I thought about targeting $1000/month, but for me $5000 seemed like more of a long shot. In reality it’s not as much about making money as it is about pushing myself, and proving that I can do it! I mean, at the end of this if I’m only making $2k/month did I really fail? I may not have reached my goal, but I would be on my way there.

      For me, it’s probably more about setting an uncomfortable goal, and having to stretch to reach it.

  2. Max
    January 3, 2015 at 8:47 am

    Good luck!

    • admin
      January 3, 2015 at 12:46 pm

      Thanks Max!

  3. January 3, 2015 at 1:35 pm

    Im certain that you can do $5k in a month; for instance, the business that i manage is planning to build out a simple website for a new product launch this year. Handling the build out is certainly within your skillset, but seems like it is probably pretty utilitarian work, not hugely interesting or challenging. And serving us with ongoing support promises to be sheer drudgery. Also, it is a front-loaded job, not a sustainable revenue stream. If you did a job like this every month to meet your financial goals, soon you’d be pulling your hair out in frustration and spending 90% of your time dealing with customer requests.

    What i hear is that you want to build something that does the work in the background, brings revenue, but doesnt demand much time. Remember that you will have to be able to respond flexibly and quickly when your solution breaks, or to adapt the solution to a specific need or client spec.

    You are exactly correct; Business occurs when a problem is recognized and then met by a solution. The biggest advice is to get going, start and do something. The first idea may not be the final idea, but always activity will bring more potential problems to your door for solution. Good luck!

  4. Brad
    January 3, 2015 at 5:20 pm

    I like it!! Does Questacular fit in here?

    • January 4, 2015 at 12:39 pm

      Brad, this challenge is separate from my day job and Questacular. If there ends up being complimentary pieces, great! But that is not the intention.

  5. Harry
    January 4, 2015 at 7:25 am

    Very inspiring Ben. Thanks much for posting and rooting for you. Best of luck for 2015.

    • January 4, 2015 at 12:39 pm

      Thanks Harry, I’m looking forward to the challenge.

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