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Sailing the world while building startups

Sailing the world while building startups

James and his partner Danielle have an enviable working set-up - they live and work on a sailing boat! They bought it after saving up money from their startups. Together they work on their products Leave Me Alone, an email unsubscribe tool and Ellie, an AI writing tool. I spoke to James about sailing across the Atlantic Ocean, mistakes that bootstrappers make and the pros and cons of building an AI product.

What’s the best and worst thing about living on a boat while building a startup?

Even before buying a sailboat, the reason we became digital nomads was for the freedom it grants. But nothing is more freeing than being on the sea 😄 We are able to work from anywhere using Starlink, and the changing scenery keeps us inspired and creative.

The worst parts are the unpredictable nature of this lifestyle. We’re constantly at the mercy of weather conditions, which can easily disrupt both sailing plans and work schedules. At the end of the day the boat must come first, and our work schedules have to fit around whatever else is happening.

James and Danielle on their boat
James and Danielle on their boat

How was it crossing the Atlantic Ocean with just a crew of 3? 

It was an intense and rewarding experience! It required meticulous planning, a deep trust in each other, and a solid understanding and confidence in our boat Nayru. 

Our third crewmate was a very close friend whom we have known for 10+ years - someone that we already knew extremely well. We know some friends who took hitchhikers with them - complete strangers in some cases - which sounds much more risky! But there's a unique kind of camaraderie that forms when you're relying on each other in the middle of nowhere, and in stressful situations!

We had a lot of things break, requiring two trips up the mast, and had a few leaks, so that last part is quite important! We didn’t have a spiritual awakening or anything from the experience like some people say they get. My main takeaway is that it’s probably good for your mental and physical health to make big changes in your life periodically. 

In our case this meant no access to the internet, so no social media, no distractions for three weeks. We all read a lot of books! And from a health perspective we ate zero processed foods, drank no alcohol, and had no meat on board (except for two fish that we caught). 

These are both things that I’m going to try and do more regularly in my life. Although we also did nearly zero exercise (it’s a small boat), which I wouldn’t recommend - I blew out my knee on my first big walk after being back on land 😅

James catching a fish
James catching a fish

How and why did you get the boat in the first place?

We accidentally stumbled upon the world of cruisers through YouTube during the COVID lockdowns, when we couldn’t travel ourselves. Watching others live and work from their sailboats, we were captivated by the uniqueness of the lifestyle. We were initially a bit surprised by how cheap it could be (we’d assumed sailing was only for the super rich), and also that we’d never thought of it before 😂

We were already passionate divers and loved the ocean. So cruising immediately seemed like a great fit for us! After years of grinding on our startups, getting Nayru felt like both a reward and a new beginning. 

What made you create Leave Me Alone?

I usually say that it sprang from our personal frustration with cluttered inboxes full of unwanted subscriptions and newsletters, which is partially true! But also at that point in our indie-hacker careers we were throwing a lot of stuff at the wall and seeing what stuck!

Initially we just focused on creating a simple way for users to unsubscribe from emails, but we quickly branched out into other features that allowed you to keep control of your inbox by blocking emails, do-not-disturb schedules, and many more features. If you can think of a way to keep your inbox quiet, chances are that we automate it!

How long did you do contracting for before you went full time on Leave Me Alone? 

I think we contracted for about 2 to 3 years before diving full-time into Leave Me Alone (affiliate). Even after its launch, we continued with part-time contracting during the first year to maintain a steady income stream.

Since Leave Me Alone wasn't immediately profitable, the contracting jobs extended our runway, giving us the freedom to focus on growing our user base and improving the product without immediate pressure to generate revenue. So a balance of both allowed us to lay a solid foundation for Leave Me Alone until it could sustain itself and support us fully.

James on their boat

Is there any mistake you keep seeing early bootstrappers making?

A common mistake I've noticed with early bootstrappers is not getting their product to market fast enough. Everyone should be aiming for a "lean startup on steroids" approach—shipping a minimum viable product within weeks and trying to get a sale as soon as possible. The key is speed. If the product doesn't catch on, it's better to have spent only a little time and move on to the next thing without much loss.

Another issue is overthinking the initial product idea. Instead of getting hung up on finding the perfect idea, bootstrappers should get something out there rapidly. The research and development process itself often sparks better ideas. Given that bootstrapping is somewhat of a numbers game, the more attempts made, the higher the chances of hitting on a successful product. 

This velocity is where bootstrappers have an edge over larger or VC funded companies—they can iterate and pivot much faster. Take advantage of that.

What’s been your proudest moment from working on Leave Me Alone or Ellie?

Probably when we first broke our $2000 MRR barrier. This was the culmination of a few years working on different projects, and then focusing on Leave Me Alone. The amount was what we’d calculated as our “ramen profitability” number, and from then on we no longer needed to work freelance and could just focus on our products!

Why did you create your AI writing app Ellie?

Honestly because I wanted to try and build something with AI, and thought I had a good idea. I think that Ellie came about at a great time, just after the huge success of ChatGPT while everyone’s minds were on AI and how they could utilise it.

However, since the launch I really haven’t given Ellie as much time as it needed (especially in marketing), so it hasn’t really been growing, even though I believe it’s the best AI Email writing tool currently out there. 

To exacerbate this slow growth, launching Ellie corresponded with our most difficult sailing season yet, so I was really getting smashed with work while also getting smashed with waves. 

2023 was a difficult ride for us 😅

I guess the main pros are the ability to share resources between the two products. For example, we have a really amazing freelancer who does our support, and having him already working on our first product meant that it was super easy to have the same setup for Ellie as well. 

I could apply this same mentality to a lot of other aspects of the business that were already set up - Stripe, hosting, servers, emails etc etc. So there’s a lot of time saved the second time around! For the next project I start I think I’ll go a step further and purchase an all-in-one starter kit like ​shipfa.st​ or ​Gravity​ (affiliate).

Try Ellie

What are the best marketing channels for your apps? 

Marketing! There’s something we all struggle with! We’ve recently shifted most of our focus to marketing. We’ve hired a content manager who writes blog posts and manages our SEO.

In the past we’ve had a lot of success from organic TikTok and Instagram reels, so we’re currently trying to replicate that!

What are the pros and cons of making an AI app in 2024?

There are a LOT of bad or incredibly simple tools out there. In my experience it’s difficult to differentiate yourself as the quality or professional option when so many of your competitors pretend to get comparable results by just being a wrapper over ChatGPT.

That said, there are also now a huge quantity of apps that help you to build your own products with AI, so it’s never been easier to get started. Just make sure you don’t make something too generic! 

Where can people find out more about you too?

I’m active on Twitter: https://twitter.com/JamesIvings

I post about sailing on Instagram: https://www.instagram.com/squarecat.sailing

You can find Leave Me Alone here: https://leavemealone.com/?via=pete

And our AI email product Ellie here: https://tryellie.com

(Since doing this interview, James has launched StartKit to let you build your own AI SaaS)

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