Sharing Your Expertise with HelpWith CEO John Connor-EP027

One of the greatest challenges new freelancers face is that of securing those first few clients. What if there was a marketplace where you could advertise your expertise to professionals who are looking for someone with your skill set?

John Connor is the Founder and CEO of, a community where people connect and exchange skills via one-on-one learning sessions. The platform currently boasts 2,500-plus users offering 1,800 skills from advanced email marketing to craft beer brewing.

Interested in the intersections of community, philosophy, and technology, John has been involved in projects like the Portland Made makers collective and the Chicago Free Skool. His passion for the startup community coupled with his own experience as a freelancer inspired him to create a space that would provide novices with access to clients and veterans with leads for advanced assignments.

Listen in as John shares his best tips for creating a killer profile, acquiring endorsements, and avoiding disputes on the platform. Learn how to use your aptitude in the creative and/or professional skills space to add an additional revenue stream to your repertoire – by way of HelpWith!

Key Takeaways

The HelpWith onboarding process

  • Sign up with Facebook or LinkedIn
  • Add a bio
  • List your skills
  • Name of skill
  • What you can teach in an hour
  • What qualifies you as an expert

The benefits of using the HelpWith platform

  • Discoverability through SEO-optimization
  • Opportunities for collaboration
  • Simple payment process
  • Reputation management via reviews, endorsements

John’s tips for making your HelpWith profile stand out

  • Compose a descriptive, clear value proposition
  • Include variations on a singular skill (i.e.: Photoshop, flyer design, web design mockups)

How to get hired for the first time on HelpWith

  • Invite people you know to join the platform
  • Ask them to vouge for you via an endorsement
  • Endorsements translate directly into gigs

How HelpWith picks up where online courses leave off

  • Many get stuck or lose motivation to finish online courses
  • HelpWith provides one-on-one resource to get you ‘over the hump’
  • Human interaction allows you to actualize new skills

How HelpWith helps entrepreneurs adapt to new technologies

  • Freelancers who maintain their knowledge base as digital platforms change are rewarded for staying on the cutting edge
  • Business owners can tap into the power of an expert for quick answers

John’s favorite simple trick to get inspired

  • Choose three words you want to embody (i.e.: focused, present)
  • Set a daily alarm on your phone as a reminder
  • Realign yourself by asking, “Who do I want to be today?”



‘Getting Started’ Blog Post

Team Treehouse




High-Performance Academy


Connect with John Connor

My name is John Connor and I am the founder and CEO of, a marketplace for teaching and learning skills with members of your community. Primarily interested in working with the intersections of community, philosophy, and technology, I enjoy using digital design and cultural analysis to help people communicate message. I've worked on a wide range of community-driven projects over the years, from Portland Made makers collective to the Chicago Free Skool. I currently reside in the lovely city of Portland, Oregon.