#77: How to Make Money Remotely (and Keep Your Daydream)

If you feel money is your biggest roadblock to living a life of travel and adventure NOW, this video is for you.  I have shared the numerous, creative ways I have found to make money so Phillip and I can cruise (as well as the many mistakes and failures I experienced along the way) and have also collaborated with a creative and charismatic team: Marc & Tricia Leach at http://www.keepyourdaydream.com, who have put together their “3 Myths and 5 Tips” for making money while traveling.  Dig in!

I first met Tricia Leach when she interviewed me earlier this year for her Keep Your Daydream podcast (which is currently nearing it’s 100th episode!).  I found Tricia incredibly easy to talk to.  She is spirited and creative and I knew she would be a great resource for this topic because she has interviewed dozens of people who are out there, right now, living an adventurous, location-independent lifestyle and making money remotely to fund it.  In her and Marc’s video contribution, they have pulled from their extensive collection of podcast interviews to put together many real-life examples of various ways to make money to cruise and they have compiled all of those resources together for you all in an extensive “Remote Income” resource page on their website.  I have included all links below for your benefit.  Marc and Tricia are also currently vlogging their own adventure as they travel across the United States in an RV with their family.  Definitely check out some of their entertaining and educational videos on their Keep Your Daydream YouTube channel.


Marc & Tricia’s extensive “Remote Income” resource page: http://www.keepyourdaydream.com/remote-income

My interview on Tricia’s KeepYourDaydream.com podcast: http://www.keepyourdaydream.com/have-wind-will-travel/

My first interview with Teddy J at SailLoot (discussing my first attempts to market my Billable Hour guide and creation of my company Legalite, LLC): http://www.sailloot.com/sail-loot-podcast-022-have-wind-will-travel-with-annie-dike/

My second interview with Teddy J at SailLoot (discussing formation of an online company as well as some of the legal hurdles, tax benefits and logistics): http://www.sailloot.com/sail-loot-podcast-030-annie-dikes-keys-kingdom-setting-small-business/

My “Market First, Write Second” article I wrote for SavingtoSail.com (discussing some of the tips I have learned from marketing my own self-published books): http://savingtosail.com/market-first-write-second/


Thanks to my many Patrons who inspire me to keep putting these helpful cruising “How To’s” out there.  Get inspired.  Get on board.


Sail Loot Interview No. 2 – Setting Up a Small Business

Hey Kids!  So, who doesn’t know about Teddy J?  Our buddy over at SailLoot.com who explores the many different ways cruisers have found to make money to travel the world.  Last time I spoke with Teddy J, we talked a lot about my marketing efforts and self-publishing Salt of a Sailor.  One thing Teddy asked me to talk about this go-round was the small business I formed to manage my marketing clients and publishing endeavors.  While my advice must always come with a HUGE disclaimer that it is NOT legal advice, I’m always happy to share the many mistakes I have made and some of the simple business methods I have found that work for me.  I always love to hear from other aspiring or already-cruising cruisers out there, though, who have found different ways to make money online.  What are you guys doing or trying?  Let me hear from you!

I hope you enjoy the interview!





Thanks to my Patrons who help me share the journey.  Get inspired.  Get on board.


Annie’s First Interview – “Get Frugal, Get Friendly”

April 16, 2015:

This may be the shortest blog post I’ve ever written.  Why??  Because you’re about to hear me ramble on for an entire hour, that’s why.  Oh wait, I’m sorry, an hour and fifteen minutes, in my first real, live interview as a … well, an author I suppose, but I think the term “authorpreneuer” © is more appropriate.  It seems these days I’ve got a lot of plates spinning.  But, that’s essentially the message I was trying to convey–get creative with your funding, frugal with your spending and you, too, can get out and spend more time sailing and cruising.  I was humbled and honored to be interviewed recently by Teddy J, the creator of Sail Loot, an innovative and informative website, to try and help Teddy answer the question folks want to ask every person who lives on a boat and cruises around the world — How the heck do you pay for it?  I hope I gave some insight and some inspiration to other budding cruisers out there.

Here ’tis.  Next time you’ve got an hour (and fifteen minutes) to kill.  Click to play:





If you’re short on time, I’d particularly recommend the “how to impress a hot guy” tips.  It’s basically–try anything adventurous and pretend like you know what you’re doing.  Works every time.

Phillip and I have been following Teddy J’s Sail Loot interviews for quite some time.  Teddy has interviewed many cruisers, live-aboards and marine innovaters who have traveled the world and launched a diverse range of cruise-funding endeavors.  One of the first interviews I heard was of the s/v Delos crew.


Captain Brian’s bio plays out much like my own.  “After years in the IT business Brian dreamt of bigger adventures and more meaning in his life.  He read the book “3 years on a 12-foot boat” and the dream to create his own odyssey and sail around the world was born. Three boats later and endless days of hard work, Brian’s dream became a reality when he bought Delos in Seattle in 2008 and has lived on board ever since.”  You can listen to Teddy’s podcast interviews of the Delos crew here:

Sail Loot Interview of Brian and Karin (Teddy’s podcast numero uno)

Sail Loot Interview of Brady and Josje (pronounced Yaaw-jsuh – beautiful name! – although I prefer her more common alias – Josjerama)

I also found Teddy’s two-part interview of Jeff Siegel, the creator of Active Captain, fascinating.


Jeff’s mind is always buzzing with new ideas and helpful technology.  He has a very honest and realistic approach to new business endeavors and speaks openly about his own failures and the lessons he learned in developing what is now the fastest-growing, most interactive marine navigational software on the market.

Sail Loot Interview of Jeff Siegel (Part 1)

Sail Loot Interview of Jeff Siegel (Part 2)

These are just two of the dozens of others Teddy has interviewed, all of whom have provided his listeners with some great insight about transitioning to a more balanced life.


In all, I was incredibly humbled to be added to this eclectic group of creative thinkers.  Thank you, Teddy J, for the experience and the platform to share my passion for cruising and my less-is-more philosophy with others.

While I was happy to talk to Teddy about the various, creative ways I have found to make money remotely, as it always seems, when you give you seem to get more in return.  Through Sail Loot, I was able to connect with several other cruisers Teddy has interviewed and help support them in their endeavors, which encouraged them to, in turn, help to support me.  It was actually the Delos crew who initially turned me on to Patreon.


Patreon is an awesome platform that allows artists of all walks (singers, songwriters, videomakers, bloggers, underwater basket-weavers, whatever!) continue doing what they love by allowing their fans to empower them in a direct and meaningful way.  I’m happy to say I am a proud patron of Delos on Patreon and (even on my tight cruiser’s budget) happily fund each of their wicked worldly videos.  I would highly encourage others to sign up to support them too.  It will be the best two dollars you’ve spent in ages, trust me!

Also, once I heard fellow boat-bum-turned-author, Ed Robinson’s, interview on writing and self-publishing, I reached out to him as well and asked if he would like to read my Salt book to perhaps provide an endorsement for the back cover.  And, look what happened …


Just goes to show you–when you help people, help tends to find its way back.  So, to answer Sail Loot’s burning question — How do you pay your way to cruise?

You get creative.  You get bold.  You get frugal.  And, you get friendly.

As Teddy would say, it never hurts to ask.  Offer something of value and then ask for support.  Worst that can happen is they say no.

Many thanks to all–my loyal followers (believe it or not – it’s been over two years now since I started this blog!), my supporters, patrons and friends.  I wouldn’t be here without your encouragement and support.  I hope you have found the posts fun, entertaining and inspiring.  Trust me, there’s always a way to make it work.  Get out there before it’s too late!

Enjoy the interview!