The Hustle

In this episode Mike & Matt discuss the entrepreneurial hustle, focusing in on the online freelance game for web developers and designers.

Segment 1 - Freelancing Online

  • There are a lot of developers, writers, virtual assistants, and more that work freelance online
  • As a small business, we have experience getting work from freelancing websites and other site resources, however, please note that we work almost exclusively in the web development/design segment of the business so your mileage may vary if you’re freelancing in a different field
  • There are a lot of different websites and services that are set up for freelancers and their customers, most of them are basically job boards with full service solutions that contain various features such as:
    • Portfolio Page: Set up a portfolio containing things like pricing per service, project showcase, history on the site (ie took successful jobs, their rating as a service providers, etc.), list of skills, and more
    • Job Board: A list of jobs typically posted by potential customers, this job board generally has a bunch of topics ranging from app development to content writing. Customers can also post things like their budget, how much they’ve spent on the site with other freelancers - to judge how serious they are, and customers can also have a profile that proves how “legitimate” they are, or show off what other projects they’ve had done so developers have an idea of their expectations
    • Payment Systems: A lot of these sites have some sort of payment system in-place that helps customers pay freelancers, and in turn, help freelancers get paid on time.
    • Premium Services: Often times these sites are free to use, but have premium features that are for sale for customers and/or freelancers. Some of these premium features include: bidding for jobs (limited bids for free, freelancers can pay for more), premium job listing (appear at the top of search results)
  • Services we’ve used include:,, Craigslist, and Kijiji

Segment 2 - Our Experience w/ Freelancer Online Services


    • We’ve applied to a few jobs on Guru without much success, however, we have had success via our portfolio on the site
    • Once we listed our skills and experience on there, we generated a few leads from people contacting us right from our portfolio page
    • This was the first freelancing site that we tried, it seemed really popular and active so we went in head first
    • We tried starting with smaller jobs, $100 or less, and ended up scoring a low-cost small adjustment job which ended up being an entire mess of a situation - mostly because the customer had an issue with his account and because we didn’t take a look at how Freelancer charges for their services
  • Kijiji & Craigslist
    • In the very beginning we tried to get some free advertising going in the “classifieds” space
    • We took a look at what other people were posting on there in the web development space, most were quick $500 or less websites that were all-in
    • Following in their footsteps we released a few different ads at different pricepoints, listing similar packages on our website
    • This resulted in one long-term customer relationship from a person that called us from the ad, but wanted general development services - not the package that we had advertised
    • We also got a call or two from people that wanted extravagant websites for extremely cheap, being offered $100CAD for an entire restaurant website at one point
    • Craigslist did not result in any leads, only Kijiji in our experience

Segment 3 - Creating Projects

  • This was a very important step for us as it gave us skills and portfolio work that we could then show potential clients
  • We created Chrome Apps, Chrome Extensions giving us a niche area of focus
  • Web templates and snippets have us experience with basic html and css
  • Not only can projects potentially generate revenue if monetized but they refine and showcase many soft and hard skills such as project management and coding style
  • A big thing for us is looking at projects as a potential revenue generators but with a worst case outcome of being a portfolio item that presents and refines our skills
  • For us we always needed to keep the the timelines on these projects very tight otherwise we would get sidetracked and lose focus
    • For Clicks to Riches we finished it within a week of intensive work
    • For Html All The Things it was also only a couple weeks
    • A project like Content Collector which has not been finished and is fully on the backburner suffered from loose timelines
  • The chrome app projects that we did directly affected getting our biggest client
  • Another flaw that we have when it comes to this is being hesitant to create a project:
    • Based on how many similar solutions to something are out there
    • Not knowing the audience well enough

Web News - Updates vs Stability

  • What do users prefer when it comes to their applications or operating systems receiving updates.

    • Having the same version for long periods of time with no features added or optimizations made but great stability
    • Having new features and optimizations every month or so but have the chance to lose stability
  • An example of fairly stable consistent operating systems with minimal updates would be iOS and partially android.
    • They usually receive one large update a year with only minor security updates in between almost like a hybrid system
  • Windows on the other hand will receive updates almost weekly that seem to be fairly untested and large updates also come multiple times a year and have the potential to introduce massive issues like with the last large scale fall update deleting a users documents folder
  • Updates to platforms can also cause problems such as Webflow or Wordpress releasing updates which makes features and plugins behave differently.

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