Sail Loot Podcast 053: Sail Me Om, Part 1

By on August 15, 2017

Jon and Tory are currently in Puerto Rico. I talked to them about 5 months ago when they were in the middle of the Bahamas. They started in New York City. They took 3 months to outfit their sailboat for cruising, headed North and then all the way South along the US East Coast before jumping across to the Bahamas.

Oh yea, and they’ve been building and running their own businesses at the same time.

I’d say that both of their businesses are in the marketing space, but trying to get an elevator pitch out of either of them was one of the hardest things I’ve ever done, and I don’t quite think that I succeeded.

I’ve talked to a lot of sailors on the Sail Loot Podcast who have downsized, saved, built sailing blogs, written for sailing magazines, found boat maintenance jobs, started charter companies, sailed part time while working during hurricane seasons, and found captain and/or crew jobs to maintain their cruising kitty. However, Jon and Tory’s businesses really have nothing to do with sailing. They have built and run their businesses from Scallywag the way that I originally envisioned a cruiser running a remote business.

In Part 1, we get into their story of purchasing and moving Scallywag across the US, moving onto Scallywag full time, and starting their own businesses.

Jon and Tory Grinding the Winches – this is not Scallywag…they were on charter. Finding a picture of both Tory and Jon sailing is quite difficult! ;)


Scallywag Wrapped up for Winter in NY

Fyre Selfie!

A Few Things You’ll Learn about Jon and Tory and Sail Me Om in this episode:

  • Not knowing how to sail when they bought a sailboat!
  • Purchasing Scallywag, a 1974 Islander 37.
  • Moving Scallywag across the country from California to New York.
  • Having their dog, Honey, on the sailboat.
  • Moving onto Scallywag to live full time on a sailboat.
  • Rent prices in New York City vs. Winter Boat Slip prices in Jersey City.
  • Teaching multimedia journalism skills in combat zones, and conflict and post-conflict zones by running The Tiziano Project.
  • Moving on to their positions in new companies in New York City.
  • The death of the corporate ladder.
  • The thought process behind their decision to leave their jobs and start their own businesses.
  • How Jon started AVG and Tory started Finally
  • Finding their first clients.
  • What Tory and Jon and their companies do.
  • Narrowing their focus to things that they can work on remotely.
  • And much more!

Links and Resources from this episode:


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About Teddy

I am a 37 year old that just wants to find a way to make a remote income, gather some Sail Loot and cruise the world! I have been sailing for a couple of years now, but mostly on 10 day trips as vacationing crew. I just recently took sailing to the next level by completing my Basic Keelboat, Basic Cruising, and Bareboat Cruising Certifications! I am also Vice President of a Medical Consulting Company, have a Mechanical Engineering degree from Georgia Tech, and have taken several Coding, Computing, and Online Business courses. It's time to share what I have learned!


  1. Linus Wilson

    August 18, 2017 at 8:05 am

    I spend a lot of money uploading podcasts in foreign ports paying for data which is expensive and hard to set up. I also spend a lot of time editing interviews to enhance sound quality. The sound quality of that interview was too bad to air. The fact that Teddy also could not be heard was surprising. I have learned and I’m sure Teddy knows or will know that most listeners will not download a poor sound quality interview. I have scapped many interviews because of their poor connections. I still think Teddy is doing great work and I applaud him for all his hard work and money spent producing this podcast!

    • Teddy


      September 13, 2017 at 12:06 am

      As I said in the first few episodes…sometimes you have to deal with what you get when you’re on the phone with people in far off places. I admit, this is what prompted me to find a better way of recording phone calls instead of using an app that people said worked very well. This app, Tape A Call Pro, did not work very well. However, I had too much good material from them to just scrap an entire 2-hour conversation. Yes, some of it is difficult to listen to, but I keep listening to it again and I say, “I can understand everything that all are saying.” You can’t. You don’t like it. Cool. Don’t download.

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