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In the interests of furthering this subs move from “clickbait get rich quick” posts to more substantive reviews of failures, I am submitting this doozy as the first in a series of my ‘Crazy Ideas’, companies I have started that never went anywhere but had an interesting ride.This is a bit long but it's fun and really far off from the normal “Sell a t-shirt/clean peoples things” posts we see so I’m hoping it's worth the read. It’s also true, even if it sounds insane.Did I mention that this is really really long? Get a coffee, don't complain, you were warned.This story kicks off in 2010/2011 or so. I was working full-time in a high-pressure consulting environment where I’d just taken the rap for a really high profile project that went south. They’d basically put me on ice for about 6 months in an attempt to get me a lower profile while the corporates looked for a scapegoat.With a ton of time on my hands, a steady paycheck still arriving, absolutely no new projects to work on, nowhere really to be and knowing that the end is nigh at some point, I needed to find the next thing. I had always maintained my side-business doing basic web backends using outsourced developers and because of that had a pretty deep roster of potential projects, so I dug into that and used this time to see if I could make something of it.One of my clients was an anti-piracy firm. Not anti-piracy in the BitTorrent sense but anti-piracy in the “We put strong Ukranian ex-special forces troops with neck tattoos on boats with guns” sense, mostly in the Indian Ocean. Knowing the sorts of problems they had, I reached out with some ideas for new cool projects that would make their lives better. Maybe connecting their GPS ping devices to a single map so they could have a global view of what everyone was doing, alerting tools, integrated CRM, stuff like that.The thing about companies in this anti-piracy space is that they are extremely dodgy. It is a grey-market at best, where one year the UN condemns you and the next year they release a policy paper saying that global commerce depends on mercenaries with guns on boats. One year a bank will take your wire transfer, the next year you are funneling money to Malta via someone’s ex-girlfriends account to try to bypass new quasi-regulations. Everyone is always threatening and backstabbing and stealing. Every contract is a 3rd of 4th level sub-contract from some other dodgy entity, usually based on who had access to legal and documented weapons at any given time (a complex topic). The stakes are high, the profit huge and the players scammy at best. The nature of the business means that people that start these companies are not… stable.This client was no exception, let's call the owner ‘Sal’. Sal spent years in Iraq as a private military contractor, providing security via some 3rd or 4th level sub-contracting company. He claimed to be an ex-army ranger but no one ever really saw evidence of that so there is a high probability that he was a southern boy that knew how to shoot and leveraged that into a high-revenue gig during the go-go days of PMC’s in the Middle East. I know he was there, he has pictures to prove it.Sal was unstable, at best. Super fun guy, really engaging, ride-or-die style, and constantly on the go, classic ADHD/BiPolar. He had a loose partnership with a few other players and together they had formed a security company where they could source Russian or Ukranian ex-army/special forces (White vs Asian is a huge thing in this space as Asian’s are seen as less reliable), provide weapons, provide GPS trackers, provide transport, a villa in Sri-Lanka and another in Dubai for off-operations waiting and staff to handle centralized comms. Through this, they had a nice little business that produced a ton of cash flow and subsidized a really nice lifestyle. Eventually, however, the natural instability of these things began to break the association apart and my call happened to come at that exact time.Sal was incredibly happy to chat with me and it pretty quickly became clear, he was ready to backstab these people. He had already collected the ‘loyalty’ of the team, had access to control of all key assets and was ready to make his move and start a new company but, due to his ADHD/BiPolar nature, was really not equipped to do the blocking and tackling it would require. Turns out, I am really good at that stuff and a partnership was formed. We quickly formed the new company by buying a shelf-company out of Cyprus (complete with a bank account), building a quick new website and presenting a business that was ready to go. Sal was able to contact existing clients and providers who, already being used to the constant shifting of names and companies in the space, seemed happy to use a new bank account for their transfers. Given the loose nature of all of this none of it is exactly illegal, but neither is it friendly..Things were immediately popping for the first month or two. Profits, in this case, were about $10k per run from Sri Lanka to the Red Sea, there was about 1-run a week and Sal was living it up in Dubai. I was getting my 10% and it was clear this had potential so we started investigating scale. Could we get our own insurance instead of sub-leasing someone else's? Could we source our own weapons with USA approval? These are the sort of things that turn a $1m/year business in this space to a $50m/year business because all of these are assets that can be sub-contracted at a huge mark-up. A low-cost weapon can be leased weekly for 2-3x its actual cost. Insurance can be haloed to sub-contractors who can’t get their own, etc etc. It's all about the provenance and regulatory approval which is required by shipping companies and they accept most things at face value.But, somewhere in month 3, it became clear that this house of cards was going to come crashing down. Sal just lacked the expertise, credibility, and stability to maintain. He’d go from working out 5 days a week and eating clean to flying to Ukraine for 3-5 day vodka benders where he was probably face down in a ditch by the end. It was clear, adult supervision was needed. Luckily, Sal’s girlfriend, ‘Sofia’, a stereotypical tall, blond Ukranian bombshell, had just the person in Odessa, Ukraine.Let's call him ‘Sergei’. Sergei was the owner of a successful shipping company and looking to diversify. He understood the market because he was hiring these firms and saw a great opportunity to not only diversify but also cut out the middle-man for his own shipping needs. Sergei and Sofia knew that Sal was the missing link in this plan and so a new company was drawn up, funded by Sergei, and we moved our ‘assets’, such as they were, over to it.Not sure if you have ever done business with mid-level Ukranian/Russian businessman in Odessa so a quick note: They are untrusting, conspiracy focused, and highly intelligent individuals that know how to leverage in equal parts money, relationships and the quiet threat of violence to achieve their goals. Lucky for us, Sergei was actually a good guy and really trying to make a go of scaling his business. One of his ships had been unknowingly caught up in some blockade running during one of the conflicts running around the Med in that time and it had hit his reputation a bit and he wanted to recover that.Pretty quickly it was clear though that Sergei and Sal were oil and water. Buttoned up Russian Businessman and insane bipolar American cowboy. In order to get this kicked off, it was critical for all of us to get together and for Sergei to understand that Sofia and I were behind Sal so it would be OK. So, like any sensible person, and against the wishes of my wife and our two young children, I took a week vacation from my day-job and hopped on a plane to Odessa for a week of meetings.Odessa is a trippy, interesting and dangerous city and my time there was no exception, lots of good stories from my week there. They put me up in a nice little apartment downtown and we had a driver. But let's be clear, this was not some UberBlack service, it was literally an old smoky Lada being driven by a guy who did not speak English, had tattoos all over his neck, and was still wearing his desert camo. This car would smoke on up to my apt and Sofia would grab me from the lobby where we would then careen through Odessa to the office, careful to not be followed. As I said, they were paranoid.The only thing that was accomplished that week was Sergei and Sal fighting endlessly. Lots of smoky meetings in restaurants filled with angry conversation. When I left, the only thing that really changed was that I was given an IT Support person to supplement my team and help manage the field teams with tech. This was important given the timezone shift everyone is operating on.Predictably, when I returned home, things went to hell within a month. Sergei realized that Sal was just unmanageable, Sal felt that Sergei was ripping him off and Sofia was just pissed, in that inimitable Russian-Woman way, that all the men couldn’t get their shit together. As the owner of the original shell company and all of our comms assets, I worked hard to keep it together but eventually, Sergei turned on everyone and had his local IT guy take control of all the assets via his administrative access to our Gmail domain. Game set and match he thought.Of course, it wasn’t. After 2 weeks of me working with Google to prove ownership and Sal pushing to move clients and assets back to the original shell company we regained control. I’ll never forget that final call from Google to move the domain back into our ownership, I was on a mountain bike ride and pulled over to take the call, approve it, and then resume my ride, knowing that the team on the water at that exact moment would now be communicating with Sal directly. At the time it felt very Neal Stephenson/Cryptonomican, and I was quite impressed with myself.Again, predictably, things just fell apart. Bills couldn’t be paid, villa’s were taken away, access to weapons was lost as Sal become increasingly unpredictable and Sofia left him which sent him into a 6+ week binge that left the entire system crippled.A year later I decommissioned that Cyprus company and put it all into my past. My final email to Sal on this :Heads up. Banks are closed and company will be dissolved with a month or two.It was an interesting ride. Good luck out there.Sergei is still doing great and the tech company idea he told me about over drinks and steak in Odessa eventually launched and is doing quite well. His shipping business continues to grow and, even though he devolved into implied threats of violence against me at the time, we are now connected on linked-in and exchange occasional pleasantries every few years via email.Sal ended up in a southern US state doing construction with some buddies until he could save up enough to move to Thailand where he bought a share in a strip club. Being unstable he quickly lost that, returned to the US, did some more construction, and then returned again to Thailand to buy a stake in a rental lodge. Recently that went belly-up as well and last I saw he is living on some beach with his Thai girlfriend. He seems happy but I imagine he will be back and contracting again to prepare for his next Thai adventure.I look back on it with fondness. It was a crazy amazing adventure that had the potential to pay-off and, while dangerous, was also invigorating, interesting and exposed me to so many things I’ve never seen. It is also a great conversation piece and I made some relationships that, while tentative, may someday be useful and/or fun. No regrets other than making my loving and supportive wife angry and worried and also the fact that I put myself into danger that they didn’t sign-up for. That was pretty stupid in hindsight, but we all get blinded by the chase sometimes.My day job? I was released about a month after I returned. Took a few months off and then started my only successful business with my now dedicated time.About me: Since I was in college, I’ve always started various businesses while working full-time and all of them except one failed (coincidentally, the one that I was committed to, go figure..). It has always been my dream to hit a home run in a strange business. My hit ratio is pretty bad but that's part of the journey, I just can’t help myself. It is fun to explore the past so I’ll probably write a few more of these for the downvotes.

#/r/entrepreneur #reddit

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