0-$50k/Mo in 4 Months with Jon Gillion from Roost

Jon Gillon The Top Podcast Episode 202

In Episode #202, Nathan speaks with Jon Gillon, 7x startup founder, 4x failer, general Silicon Valley Hustler, and free-style rapper. Listen in as Jon shares his story of early failure, how he remained persistent, and how his latest startup Roost came to be.

Famous 5

  • Favorite Book? – How to Win Friends and Influence People
  • What CEO do you follow?— Jack Dorsey
  • What is your favorite online tool?— Slack
  • Do you get 8 hours of sleep?— Yes
  • If you could let your 20 year old self know one thing, what would it be?—Nobody really knows what they’re doing…they’re learning as they go along. Just try it and be confident.

7 time founder, @Roost, @Dropertytax, @Doubletap, 4 fails. Hustler, advisor, freestyle rapper.

Time Stamped Show Notes:

  • 01:08 – Nathan’s introduction
  • 01:30 – Welcoming Jon to the show
  • 01:53 – The 4 failures were Jon’s most important lessons
  • 02:40 – Did the friends and family round
  • 02:53 – Hiring an engineer is the hardest part of getting a business off the ground
  • 04:05 – Just in the failed businesses Jon’s raised $35K
  • 05:20 – Jon’s biggest competitors
  • 06:00 – 15% transaction fee on all Roost transactions
  • 06:29 – AirBNB for inanimate objects
  • 08:22 – How to look for a lead investor—it’s not a willy nilly process
  • 09:45 – Zipcar and Enterprise are big partners of Roost
  • 10:16 – Finding a technical co-founder at the start of Roost
  • 12:20 – http://www.medium.com/@jongillon

3 Key Points:

  1. You’re not looking for a lead investor, you’re hiring one—this person will be a part of your company for a long time.
  2. Bringing a GREAT engineer on-board early is key to the life of your business.
  3. Nobody knows what they’re doing until they’re actually doing it—just give something a try!

Resources Mentioned:

  • Edgar – Nathan uses Edgar instead of other scheduling tools for Twitter because Edgar cycles through content over and over (buffer/others you have to re-input content over and over – time consuming). In the last several months, Edgar has driven Nathan over 3728 clicks that he didn’t have to work or pay for.
  • Host Gator – Powerful web hosting made easy and affordable.
  • Slack – The online tool Matthew can’t live without
  • How to Win Friends and Influence People – Jon’s favorite business book
  • Jack Dorsey – The CEO Jon closely follows



Show Notes provided by Mallard Creatives