The Story of How Not To Sail

Several years ago, after the sailing bug advanced to the terminal stage, and while I was producing The Multimedia Ninja podcast, I had an idea.

In the podcast I’d say I’m not an expert, but I can share some things NOT to do.

I thought, “Hey, I can help some folks out with buying and enjoying a sailboat, too!” And some of my stupid mistakes might just be entertaining, as well.

Work Begun

So I started writing down some chapters for a book I decided I’d call How Not To Sail.

I got the idea from, of all things, a book on video gaming. (A habit I have mostly been able to steer clear of.) In the book, the author would start each chapter with some bass-ackwards advice, like, “Try playing the game drunk, you’ll do so much better!”

So I figured I would do the same, and I could even use the beginning of each chapter to set up — and then dispel — some common misunderstanding about cruising.

But mostly what I wanted to do was just share the joy of cruising around in Jacie Sails, overcoming challenges and visiting really cool places — and to show that you can do it, too.

Of course, things happen in life, like making a living; and so “How Not To Sail” remained a to-do doodle on the whiteboard in my studio, while I took a detour.

The Detour

The detour started when I emailed Bob Bitchin.

Well, that’s not exactly right. It all started when I made the video.

I should explain.

You see, I have the weakness — er, capability — of taking on more things than can actually be accomplished by one human. So with the book in full swing, I decided, Hey, I’m a multimedia ninja…I should do a podcast on this. And while I’m at it, I should make it a video podcast too!

What could possibly go wrong? (cont’d…)

“Maybe I’ll do video…”

Well…a lot. I’m pretty quick with the multimedia stuff, but producing an audio podcast obviously adds more to your schedule. Producing a video version — especially with good production — is a recipe for insanity.

(Before this came up, I produced about forty of the seventy episodes of The Multimedia Ninja podcast in dual audio and video versions, with a super-intensive graphics intro. And I didn’t want to do that with How Not To Sail.)

But I thought maybe I could do a quick five-minute weekly “How Not To” tip on both audio and video.

So I started scripting some short video pieces on “How Not To Sail,” and shot some of the video aboard Jace Sails. I figured it would be a good support for the book.

I’ve known Bradford Rogers for a few years now, and I gotta tell ya, when it comes to sailing he is not the brightest bulb in the pack!

Sailing with Bradford keeps you feeling like a long tailed cat in a room full of rocking chairs. Even if you make it back to the dock, you are still wondering just how you made it back safe! If there is anything to be gleaned from this book it is how not to sail.

Hey, that’s the name of the book!! What a kewl discovery!

Bob Bitchin

Publisher & Janitorial Assistant, Latitudes & Attitudes

Since Latitudes & Attitudes and Bob Bitchin were largely responsible for my cruising problem, I thought it would be cool to have a column in the magazine. (Which, as we know from elsewhere, was called Cruising Outpost for a few years.)

So I sent Bob an email.

Actually, I’d kinda been dreading it. Not because Bob’s an intimidating guy (he is), but because I figured I’d just get some gatekeeper with a boilerplate response, basically telling me “Thanks, but no thanks.”

Much to my delight, though, I actually heard right back from Bob himself…telling me “Thanks, but no thanks.”

“We’ve pretty much got the column thing covered,” he told me. “But your video stuff is pretty good. And you’ve got a good voice. You should talk to Dan at Pyrate Radio.”

(You see, along with my email pitch, I’d included a sample clip of my “How Not To Anchor” video. I’ll put a link to it at the end of this story.)

Pyrate Radio

And so began a year-long sojourn at Pyrate Radio. Which was very cool and informative: I did a four-hour show most Saturdays from May 2018 to May 2019, and learned a lot about radio production and hosting.

But there was one problem. It wasn’t How Not To Sail.

My book and my audio podcast languished while I focused on the radio gig. But finally, time was up.

The A-HA Moment

The Miami Boat Show was scheduled for February 2018, and I was due to make an appearance for Pyrate Radio.

I decided it was time to go for it. I would get going with the (audio) podcast How Not To Sail…and, hey, I could sail around from St. Pete to the boat show in Miami to promote the podcast. And HEY…I could even make the trip part of the podcast.

The Spring issue of Cruising Outpost would be coming out right after the boat show, and I worked out a sponsorship with Bob and an ad in the magazine. I couldn’t wait!

And soon after the launch, I’d finally get the book out, just like I’d dreamed for the last several years.

(And in case you’re wondering, I wrote off the idea of doing a video series. But now that’s come full circle, too, and you can enjoy exclusive video fun on the How Not To Sail YouTube channel.)

The Trip

As you can hear in the podcast, I sailed from St. Pete on February 2, 2018, toward Miami. Tanya (“The Admiral”) would fly in on February 13th, in time for Valentine’s day…and if everything went well, I’d even be there to meet her.

I booked a slip at the Miamarina, smack in the middle of downtown Miami, for the three(?) days of the boat show. A little pricey, but this kinda thing didn’t happen every day. And besides, we’d be just a short walk from free transportation to the boat show. (Which, if you’ve been, can be something of a, uh…”cluster.”)

As it turns out, there was a big surprise in store for us at the boat show. You’ll have to listen to the podcast for that part.

But here’s the thing…

At Last!

I finally have a How Not To Sail podcast and book! I’ve been thinking about this for years, since shortly after I bought Jacie Sails, and it’s finally a reality.

It’s been a ton of work, but it’s been totally worth it.

And you know what? I wouldn’t be able to do it without you.

(Well, maybe you haven’t even heard the podcast or read the book yet. But if you’ve gotten this far, you might as well, eh? I know I can count on you.)

It’s been so gratifying to hear from people who’ve enjoyed the trip, and a not-small number who’ve either finally decided to take the plunge and buy a boat and go cruising…or who’ve finally got up the gumption to wander a little farther afield from the marina.

That’s what I do this for.


I’ll say this, though. Piloting this ship (metaphorically speaking) is a ton of work. Producing the audio show. Adding stuff to the website. Writing the books. (Yes, I said “books”…plural. Stay tuned.) And I don’t get paid by anybody in particular.

But you can help a fella out, #HowNotToSailer.

If you like this craziness, if you’ve been entertained a little by the podcast or the book or one of the videos, maybe you can tell a friend.

(Or if you want to go beyond that, you can check out this page with several other ways you can help spread the gospel of How Not To Sail.)

Your word of mouth is what’s grown this monster so far. You can tell a friend about the podcast. (If they don’t know about podcasts yet, just tell ‘em it’s like their own radio station, on whatever subject, whenever they want it…for free.)

And if your friend is thinking about buying a boat—or if they’ve just pissed you off lately—you can direct them to this wonderful new book: How Not To Sail.

(And just a tip: If you subscribe to the email list (free, of course, and I never share your info with anyone), you’ll get a heads up on free book giveaways, exclusive content, and members-only events and stuff.)

I really, really appreciate ya reading this, and going on this journey with me. Your feedback on the podcast and the book (and now the YouTube channel) is what keeps me going.

Talk to you soon, and thanks again,