Sail Loot Podcast 022: Have Wind Will Travel with Annie Dike

By on April 16, 2015

Annie had grown up, gone to college and earned her law degree at Alabama. She started practicing litigation law, but after a while she realized that she was only having fun about 10% of the time. She decided that it was time to change her lifestyle.

Annie had always loved writing, and had started writing a novel, but eventually found out that it was easier (and maybe even much more fun) to write about her own experiences. Everybody in the law practice had always told Annie that she was the most awesome and efficient biller that anyone had ever seen! Annie was always getting asked how she was able to bill so well.

Now, Annie answers them by saying, “Head on over to and read my book The Billable Hour.” Then, she hops on her sailboat, Plaintiff’s Rest, with her “hot guy”, Phillip, and goes cruising for the rest of the day.

Being a lawyer, and writing her own book, Annie decided that it would be smart to start her own business too. Legalite, LLC is the business that all of Annie’s endeavors now fall under.

Now that Annie has some sailing and cruising stories to tell, what do you think she did? You’d be right if your answer was, “Write a sailing book!” So the question is…are you salty? You should be! Get salty with Salt of a Sailor by Annie Dike.

You can also check out Annie’s blog at In fact, you should go ahead and become a Have Wind Will Travel Patron while you’re at it!

Enjoy this week’s episode of the Sail Loot Podcast with Annie Dike from Have Wind Will Travel.

P.S. – Annie, please forgive me if there are any grammatical and/or spelling errors here. In fact, please just let me know about them in a private email and I will try to fix them. Please just remember that I’m an engineer by training, and they didn’t teach us too much about run-on sentences. It was more about the Thermodynamic Process and what it meant for circuits to be wired in Series or Parallel. I’ve got the battery thing down. ;)

Annie Dike Sailing

The Billable Hour




Salt of Sailor

A Few Things You’ll Learn About Annie Dike and Have Wind Will Travel In This Episode:

  • Annie’s methods to impress a “hot guy”.
  • Her first sail with “hook mouth”. “Not a single lesson,” as Ferris Beuller would say.
  • Getting her first blog post into Cruising Outpost Magazine.
  • Annie’s time as a litigation lawyer.
  • Writing and self-publishing The Billable Hour
  • How Annie was able to put together a webinar that goes along with The Billable Hour and get it to be a continuing education credit hour for lawyers.
  • Forming and using Legalite, LLC, Annie’s internet and social media marketing service business.
  • Annie and Phillip’s relationship timeline.
  • Reducing debt and downsizing.
  • The search for their sailboat, Plaintiff’s Rest.
  • Sailing Plaintiff’s Rest home…Annie’s first real sail.
  • Sailing in Pensacola Bay.
  • Annie’s trick to finding her clients and being selective.
  • Annie’s love of writing.
  • Annie’s “Aha” moment for writing Salt of a Sailor.
  • Annie’s Top Tips!
  • And much more!

Links and Resources From This Episode:


Thank you very much for listening to the show! If you enjoyed listening, it has helped you in any way, or you know somebody else that would enjoy it, please share it using the social media buttons that you see on the page.

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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!

One Comment

  1. RobertM

    May 5, 2015 at 7:09 pm

    Hi Teddy,

    Looking forward to the next podcast. They are always entertaining.

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