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Hiring a Team of Freelancers

Mar 22, 2016

This past month, I did something I never thought I’d do—I hired people. From the very beginning, I always saw myself building Cushion as a solo developer, riding into the sunset with a small, sustainable app. I romanticized growing Cushion to the point where I could live off its income alone. Once I reached that goal, I would retire to a cabin upstate and simply maintain it for years to come.

That all sounds lovely, but it’s far from reality. Growing an app is incredibly hard—especially when you’re also the designer, developer, and support person. Aside from the daunting task of making an app profitable, loneliness starts to creep in after years of trudging in the same direction. Whereas I once dreamed of running Cushion by myself, I now dream about collaborating with a small team.

Recently, this dream has begun to take shape. Late last year, I started brainstorming with freelance writer Carly Ayres on where to take Cushion from a content perspective. Ever since, we’ve been working toward a goal of supporting the freelancer community and providing truly useful content—not the same listicles that have overtaken every other app’s blog.

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Last week, we launched the first interview in our new series, Talking Shop, where we talk to freelancers about freelancing. Like building an app on your own, freelancing can be incredibly lonely, too. Most freelancers don’t work in a co-working space or big city where other experienced freelancers are within arm’s reach. Talking Shop is our attempt to bring the conversation to those who are eager to learn more about the freelance world from those who live in it.

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Alongside Carly, I hired freelance illustrator Ping Zhu to illustrate each person we interview. I see illustration as a primary area where Cushion can embrace the freelancer community even further. Each piece of content we publish should be paired with its own illustration that lends itself to the writing. The content is then a collaboration between several freelancers and credited as such.

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In February, I hired freelance developer Larry Fox to help with the actual app. We’ve worked really well together in the past, so I reached out immediately when he decided to go full-time with freelancing. In his first month alone, working only a few days a week, Larry and I were able to launch Overbooking, Availability, and the Availability Badge. Needless to say, Larry has been essential to taking Cushion where I want it to go.


If I didn’t hire the help I so desperately needed these past few months, I would probably be stuck on a single feature, spinning my wheels, and only imagining the things I want to do with Cushion. Instead, I’m leading a team of freelancers, building features at a lightning pace, and publishing new content on a schedule. I’m not alone anymore, and I think I prefer it this way.

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Archive

  1. Funding Cushion
    Story
  2. Hiring a Team of Freelancers
    Story
  3. Taking a Real Break From Work
    Story
  4. Slack as a Notification Center
    Dev
  5. Document Your Features
    Story
  6. 300
    Story
  7. Vacations
    Design
  8. Offering Discounts
    Design
  9. Waves of Traffic
    Story
  10. Less Blogging, More Journaling
    Story
  11. Retention Through Useful Features
    Design
  12. The Onboarding Checklist
    Design
  13. Spreading the Word
    Story
  14. From Beta to Launch - The Subdomain
    Dev
  15. From Beta to Launch - Sign up
    Design
  16. From Beta to Launch - Messaging
    Design
  17. Launch
    Story
  18. Authenticating with 3rd Party Services
    Dev
  19. Intro to Integrations
    Design
  20. Inspiration vs Imitation
    Story
  21. The Emotional Rollercoaster
    Story
  22. Designing Project Blocks
    Design
  23. Everything in Increments
    Story
  24. Deleting Your Account
    Design
  25. Designing the Subscription Page
    Design
  26. Rewriting the Timeline
    Dev
  27. Restructuring the Individual Project Page
    Design
  28. Project Blocks
    Story
  29. Redesigning the Homepage
    Design
  30. Multiple Timelines
    Design
  31. Archiving and Estimate Differences
    Design
  32. Multiple Financial Goals
    Design
  33. Zooming in on the Timeline
    Design
  34. Currency
    Dev
  35. Preferences, Accounts, and a Typeface Change
    Design
  36. Sending Out the First Email
    Story
  37. Currency Inputs, Notifications, and Invoice Nets
    Design
  38. Dots and Lines
    Design
  39. Calculating in the Database and Revealing Tendencies
    Dev
  40. Improved Form UX
    Design
  41. Cushion is Online
    Story
  42. Schedule Timeline Patterns
    Design
  43. A Slimmer Schedule Timeline
    Design
  44. The Schedule Timeline
    Design
  45. Plugging in Real Data for the First Time
    Design
  46. Transitions and Project Lists
    Design
  47. Death to Modals
    Design
  48. The Individual Project Page
    Design
  49. Estimated Incomes and Talks with Other Freelancers
    Story
  50. Statuses to Lists and the Paid Beta
    Story
  51. The Timeline
    Story
  52. Invoice Terminology
    Dev
  53. Modal Forms
    Dev
  54. Wiring the Backend to the Frontend
    Dev
  55. Balancing Design and Dev
    Story
  56. Timecop, Monocle, and Vagrant
    Dev
  57. Going with Ruby and Sinatra
    Dev
  58. Ditching local-first and trying out Node.js
    Dev
  59. Switching to AngularJS
    Dev
  60. Building the Table with Vue.js
    Dev
  61. Clients, Projects, and Invoices
    Dev
  62. Introduction
    Story

Ask a Freelancer

A podcast series where experienced freelancers answer questions about freelancing.

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Talking Shop

An interview series where we talk to freelancers about important topics in the freelance world.

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Running Costs

Take a close look at the costs that go into running a web app and why we use specific services.

View the Costs

How It’s Made

Follow along with the journal for insight into the overall experience of building an app.

Read the Journal