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Digital Nomad for 8+ years, bootstrapping products around the world! 🌏 🙅‍♂️ Easily unsubscribe from emails - leavemealone.com

1k following26k followers

The Entrepreneur

James Ivings is a globe-trotting digital nomad who has mastered the art of bootstrapping products across continents. With a relentless work ethic and a knack for leveraging technology, he's built a digital career marked by high engagement and innovation. His tweets reflect a savvy mix of humor, candid insights, and genuine entrepreneurial spirit.

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$1970.66
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Retweets
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Replies
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Bookmarks
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James has tweeted so much, I'm convinced his keyboard has a restraining order against him—maybe take a day off before your fingers stage a mutiny!

Achieving $10k/month, making him the wealthiest person in his family history, highlights his entrepreneurial success and persistence in building digital revenue streams.

James's life purpose revolves around creating impactful digital products that empower others while enjoying the freedom of a nomadic lifestyle. He seeks to disrupt traditional work models by proving that success can be self-made and location-independent.

He values independence, innovation, and practical problem-solving over corporate bureaucracy. James believes in direct communication, transparency, and leveraging technology to simplify complex challenges.

His biggest strengths lie in relentless productivity, strong networking skills (knowing the right people to bypass red tape), and the ability to identify and bootstrap promising digital products quickly.

James's high tweet volume could lead to noise that dilutes his message, and his candid, sometimes sarcastic humor might alienate more sensitive followers.

To grow his audience on X, James should focus on curating his content to highlight key entrepreneurial insights and success stories, engage more with followers through Q&A sessions, and leverage his nomad lifestyle as a unique selling point to attract aspiring digital entrepreneurs.

Fun fact: Despite tweeting over 20,000 times, James remains committed to authentic, no-nonsense insights rather than polished corporate speak—proving that volume and value can indeed go hand in hand.

Top tweets of James Ivings

It's ready! 🚀🚀🚀🚀🚀 Introducing Ellie - your email assistant! 💌 Ellie is powered by @OpenAI and will learn your writing style and reply to emails as if you wrote them 🔥 If you want to be an early user, please retweet and comment below and I'll send you an invite code! 🙂

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🤯 Omg @stripe just sent us these renders of our boat as a congratulations on hitting $50k ARR and they're the absolute cutest thing I've ever seen 🥲🥲🥲

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just @Starlink causally doubling the price of the subscription 🥲

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Most engaged tweets of James Ivings

It's ready! 🚀🚀🚀🚀🚀 Introducing Ellie - your email assistant! 💌 Ellie is powered by @OpenAI and will learn your writing style and reply to emails as if you wrote them 🔥 If you want to be an early user, please retweet and comment below and I'll send you an invite code! 🙂

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WE'RE SELLING OUR BOAT 🥲 After 2 years sailing 10,000 nautical miles from Greece to Trinidad, we've decided to go back to being digital nomads for a while. I've learned a LOT in the last two years, so if you've ever thought of doing #boatlife as an indiehacker/nomad then strap in! I'm going to lay it all out for you. This is the shit you wont hear about on socials! Starting with... 1. Sailing vs Lifestyle ⛵ Some people that we've met LIVE AND BREATHE sailing, they've been dinghy sailing since they were 4, went on sailing trips growing up, and worked doing boat deliveries for 10 years to save up for their boat. They absolutely love it. I thought that would be me. Danielle and I love being in and around the ocean, and sailing is basically that right? But I've figured out that although I do enjoy the sailing most of the time, I'm not *passionate* about it. I think unless you are, it becomes very difficult to enjoy being on the boat when the sailing is tough or the weather is bad. However, I do love the lifestyle parts - waking up with the sunrise, going for a morning swim, exploring reefs, visiting new islands every day. It sounds cheesy but you do really feel like you're a part of a bigger world, it's humbling and inspiring. Sometimes that's enough, but when shit is going wrong all the time and you have to do the bits you don't enjoy more than the bits you do, you wonder why you're bothering with this at all. So yes to the lifestyle, but meh to sailing. 2. Everyday Nomad Life vs Boat Life 🦆 After being digital nomads for 6 years we had our life pretty well handled. Some of the best parts about being nomad is outsourcing all the annoying time-consuming life stuff that you have to do if you live a normal life. This is generally so cheap in the places we live that we do it without thinking. For example: - Paying someone to do your laundry - Getting food & groceries delivered - Having someone clean your room/condo/villa for you It sounds really basic stuff, but holy shit you notice it when you have to do it yourself again. Plus doing any chores on a boat takes about 10x longer than on land. Eg to do laundry we have to haul it out of the boat, get it all into the dinghy, take it to land without getting too salty, find the nearest launderette, etc. Doing one chore can take you the entire day. Nomad life is all about engineering productivity by removing the things that take up your time, whereas boat life is more about sacrificing your productivity in exchange for the lifestyle. So that brings us to... 3. Being productive 👨‍💻 Have to work 9-5 during weekdays? Forget it. We know a couple of people who make this work but I've no clue how. Even if you can stay anchored for somewhere a long time, being constantly productive on a boat is basically impossible. I imagine it's similar to having young kids, except your kid weighs 10 tonnes and hurts itself all the time. It's constantly demanding your attention and you have to keep it happy. And then there's the weather. When sailors told me the weather will dictate your life I though that just meant where you can go, but it's way more than that. Storms, wind changes and swell can all make the anchorage (or marina) you're in be super uncomfortable so you have to keep an eye on it and move place at little notice. So if working is your priority then you're going to be frustrated often. I'm lucky that I had a couple of businesses (leavemealone.com & tryellie.com) already on autopilot bringing home ~$10k MRR - and neither are super demanding of my time. But I tried building a new business (startkit.ai) a few months ago and that has been TOUGH. I'm constantly a bit stressed that I'm not able to spend more time on it. Work definitely doesn't dictate my life - I want to work so that I can enjoy myself. But I also really enjoy writing code and building businesses, and that aspect of my life has become a bit difficult. 4. Health and Fitness 🏋️ - Sleep I must have lost years off my life from sleeping badly on the boat. Wind or waves changing in the night will wake you up, even if you're quite a heavy sleeper like me. The boat rolling will also stop you from getting to sleep. There's nothing worse than a rolly anchorage. I'm quite good at dealing with broken sleep, but it turns Danielle into a monster. So that's more of a problem for her than for me - Food When we were nomads I really missed having my own kitchen, so we made sure to get a boat with a great space for cooking. We've eaten super lean for two years, mainly fish, tofu, veggies and rice. We've both slimmed down, and if we could stop drinking beer (and rum) then I think we'd look great! - Fitness I feel 200x stronger than I was when we bought the boat. Mostly core, back and upper body. Before nomading I was a regular at the gym (which I always hated), but after starting nomad life I never got back into the routine and although I didn't get fat or anything, I could feel my fitness + strength fading. Daily working on the boat and regular freediving has been really great, and I think I feel in better shape than when I went to the gym. I bet I couldn't do any serious isolated lift, but doing real-world stuff to build muscle generally feels better to me. 5. Social media bullshit 💩 If you're interested in boatlife at all, then there's probably a few YT channels you've watched, or a sailing Insta couple you follow. Everyone knows this but still gets tricked - any glamorous boatlife stuff they post is either total bullshit or way over the top. Instagram filters are not just a thing that changes what the photos look like, there's also a LIFE FILTER. These people are selling you their lifestyle and most people don't want to watch them cleaning their toilet tank with their arms covered in shit, or sweat dripping off their chin carrying laundry to shore. You get to see the good happy parts disproportionately more than the awful parts. When you're doing boatlife, insta also hurts because it looks like everyone around you is having a great time and not bothered about the weather or whatever. But when you talk to real people you learn that everyone has the same set of problems and is going through their own tough times too. 6. Location, People & Culture 🗺️ The best part for us was sailing around Europe. We love Mediterranean culture (mainly the food & drink 🙃), and had some really unforgettable times sailing up to random towns in Greece, Spain or Croatia, hopping off the boat at the dock and walking straight into a waterside taverna for cañas and tapas. But as we're from the UK, we can only stay in Europe for 90 days in every 6 months. Which is super annoying to manage with the boat if you're trying to move around the whole Mediterranean. 🌊 So we decided to cross the Atlantic and check out what the Caribbean had to offer. Crossing an ocean was an insane experience, one of the most crazy things we've ever done, and will really be a core accomplishment of my life. However, after that experience, arriving and exploring the Caribbean has been a bit disappointing. We landed in Barbados and headed north all the way to the British Virgin Islands before turning around, visiting most of the islands en route. The further North we got, the less we liked the places. Kinda obvious but the closer we got to the USA the more US tourists there were, and the more like a theme-park everything became. There was no local culture - I guess it's consumed by tourism - and everyone seems unhappy. I don't want this to be a review of the islands, but ask me if you want to hear more about them. 7. Friends & Loneliness 🥹 We've met a lot of boaters of all different ages and backgrounds. Boat people are truly one of the kindest, most generous people I've ever met. There's always someone who will go out of their way to help you, people give things away all the time, and almost without exception they'll be happy to have a new friend to talk to. But we also miss our nomad friends! And we miss being in a vibrant city with things happening every day. We miss going out for dinner with friends and doing new stuff all the time. Boat life is very very slow, super calm, and you're isolated. I can see why people retire and buy a boat. If you want a retirement village style life, where you can go to bed early, work on your home, and never be bothered by anyone, then it's perfect. But we need a bit more life. 8. Costs 💸 There's this assumption that boatlife is super expensive - if that's holding you back then it shouldn't. Same as nomad life, you can make it as cheap or costly as you want based on your tastes. If we ignore the price of the boat ($65k, which hopefully we'll get back when we sell), then the cost has been pretty much the same as our nomad life. We did a few upgrades to the boat which cost about $30k (watermaker, self-steering, more solar, starlink, electric outboard), but these things improved our lives a lot over the two years so I don't regret them. Also the general recommendation is to set aside 10% the cost of the boat for maintenance per year, which has been accurate. So cost-of-living + maintenance has been about $3000/month on average, which is not that different to before even though we're not very careful about what we spend. 9. What's next? 🤔 We *love* traveling, it's what we do - we zoom around and find cool places to live, and if we don't like somewhere then we leave and go somewhere else. In contrast, with boatlife we were forced to stay in a lot of places that we didn't really like, often for extended periods of time - usually a boat yard (which all suck). I think that because we're more passionate about travel than sailing, the boat kind of felt like it was holding us back a bit. So we're going back to traveling more again! Starting with Japan in September (after we're done selling the boat), then back to Bangkok for a while (our previous base). Also it's been two years since we've met any other nomads, so I'm going to try harder to meet more people, I miss people! So hit me up if you want to grab a coffee! ☕ Finally, owning a boat has made us a bit more keen on having a physical place somewhere where we can store things that are important to us, and always come back to as more of a home. 🏡 So we're going to start looking at where we can buy a nice apartment/condo (probably Bangkok), any tips on this let me know! 10. Will you sail again? ⚓ Despite my complaints, the lifestyle is awesome and I will miss it 🥲 I think we'll be back sailing again someday - maybe in retirement when we're a bit older and more tired 😂. And next time we'll get a catamaran for more stable nights sleep! Or chartering boats for a few weeks with friends + family would be great fun. We're going to try this out and see! Okay I think that's everything! If you know anyone who wants a beautiful, well-maintained Oceanis 361, I'll post a link to the boat listing in the comments! 🙂 💬 And if you have any questions about boatlife vs nomadlife, AMA!

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